DealQuest Podcast with Corey Kupfer

What if the job you almost didn't get became the foundation for building two public companies? That's exactly what happened to Babu Sivadasan, who was rejected by nine firms before landing his first job out of college, a job he still calls the best deal he ever made. Babu is a serial entrepreneur and engineer who co-founded stamps.com and later co-founded Envestnet, two category-defining platforms in commerce and wealth management technology. He's now the founder of Jiffy AI, applying artificial intelligence to how software gets created and deployed. In this episode, Babu traces a 1990s patent that became stamps.com, a demo computer damaged in his suitcase before a make-or-break Postal Service pitch, and an accidental pivot into wealth management that led to Envestnet. He also shares why he believes natural language will replace traditional programming, and how that belief now drives Jiffy AI. Whether you're weighing whether to raise capital or curious how AI is reshaping wealth management technology, this conversation offers a rare, three-decade view of how founders build through very different technology eras. FOR MORE ON BABU SIVADASAN: https://www.jiffy.ai FOR MORE ON COREY KUPFER: https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today! Episode Highlights with Timestamps [02:20] - Rejected by nine firms before landing his first job [05:17] - The 1990s patent that became stamps.com [13:19] - A damaged demo computer and a make-or-break Postal Service pitch [25:15] - The accidental pivot into wealth management [32:41] - Unifying a fragmented advisor tech stack at Envestnet [54:06] - Jiffy AI today: Series B funded, $61 million raised Guest Bio Babu Sivadasan is a serial entrepreneur with deep experience building and scaling public companies backed by a strong engineering foundation. He co-founded stamps.com and later co-founded Envestnet, helping shape category-defining platforms in commerce and financial services. He is now the founder of Jiffy AI, applying natural language AI technology to how software is created and deployed for the wealth management industry. Babu is also an active angel investor and mentor, supporting startups across Silicon Valley and India. Related Episodes Episode 328 - Richard Manders: a fellow engineer-turned-founder whose curiosity about how things work led him from an early career in automation to building and scaling multiple companies with private equity backing. Episode 370 - Gerry Hays: explores how collapsing startup costs and artificial intelligence are reshaping who can raise capital and become a founder, a theme that runs through Babu's own move from the cloud era into the AI era. Episode 350 - Tom Dillon: examines when founders should look beyond venture capital for funding, a question Babu faced directly in the cash-strapped early days of stamps.com.

"Give me a price, I'll give you a structure. Give me a structure, I'll give you a price." In this solocast, Corey Kupfer takes that favorite saying of his and uses it to unpack a handful of the deal world's most repeated cliches, testing which ones hold up and which ones only apply in certain situations. Corey has spent more than 35 years structuring and negotiating deals, and in this episode he draws on that experience to walk through what's really behind a purchase price, a valuation multiple, and a few tax and entity assumptions sellers often take as gospel. WHAT YOU'LL LEARN: Corey breaks down what actually makes up a deal structure, from escrow and promissory notes to earnouts and rollover equity, and why "give me a price, I'll give you a structure" is the question that should come before you get excited about a top line number. He also digs into why comparing multiples without knowing what they're calculated on is misleading, when the advice to take cash up front actually applies, and why he pushes back on the idea that most businesses can't be scaled or sold. KEY INSIGHTS: A purchase price is never just one number. Escrow holdbacks, contingent payments tied to retention, earnouts tied to growth targets, and rollover equity can all sit inside a single deal, and each one carries different risk and different timing. Multiples are almost never apples to apples. Most quoted multiples are calculated on adjusted EBITDA, and buyers can adjust that number differently, which means a higher multiple doesn't always mean a higher price. Take cash up front is better advice for Main Street, owner operator deals than it is for the middle market and up, where professional buyers and PE backed firms have more reputational reasons to pay what they owe. The S Corp regret Corey heard at an industry event traced back to a missed QSBS election, not to S Corps being universally worse. Entity structure decisions depend on industry, timing, and ownership goals, not blanket rules. Corey doesn't believe in unscalable businesses, only businesses that haven't found their systems yet. The same logic applies to sellability, most businesses that can't sell today can become sellable with the right changes. Perfect for entrepreneurs preparing for a sale, raising capital, or negotiating a licensing or royalty deal who want to ask sharper questions before they get anchored on a number. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/dealcliches FOR MORE ON COREY KUPFER https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Episode Highlights with Timestamps: 01:01 - The famous deal world saying, give me a price, I'll give you a structure, and why it matters 03:45 - What's actually inside a deal structure, escrow, promissory notes, and contingent payments 06:24 - Why comparing multiples without knowing what they're calculated on is misleading 09:08 - When take cash up front is real advice, and when it isn't 13:41 - The S Corp story from an industry event and the QSBS election behind it 16:45 - Why Corey believes every business is potentially scalable and sellable Related Episodes: Episode 328 with Richard Manders, for a deeper look at multiple arbitrage and how buyers think about valuation multiples. Episode 339 for more on purchase price structures, contingencies, and how retention and earnouts affect what a seller actually collects. Episode 325 with Kelly Finnell, for a related conversation on tax advantaged entity and ownership structures. Keywords/Tags: deal structure, purchase price negotiation, EBITDA multiple, adjusted EBITDA, earnouts, rollover equity, escrow, QSBS, S Corp versus C Corp, business sellability, business scalability, licensing royalties, M&A negotiation, DealQuest solocast

From a two-for-one lawn-mowing deal he negotiated with his neighbor as a kid to founding a holding company that keeps established Virginia businesses in Virginia, Andrew Dunlap shares his data-driven origin story, a fund built to avoid short-term pressure, and why he believes trust is the only currency that always matters. Andrew is the founder and CEO of Harbor, a long-term, buy-and-hold company that acquires established Virginia businesses and keeps their teams, leadership, and jobs rooted in the state. In roughly two years he has completed three deals, including a CNC machine shop and a FINRA-registered broker dealer, with an industrial services company moving toward close. He describes himself as someone who stumbled backward into this work by digging into merger and acquisition data. WHAT YOU'LL LEARN: You will learn why keeping a company's headquarters local changes how much of its revenue recirculates in the community, how an untimed fund with no AUM fees removes the pressure to make what Andrew calls caffeinated decisions, how Harbor structures flexible deals to become the buyer owners actually prefer, the earnout test that separates a real growth forecast from a wishful one, and why Andrew treats trust as the most durable asset in any market. ANDREW'S JOURNEY: Andrew grew up in Baltimore and moved to Roanoke, in Virginia's southwest, ten years ago. Coming out of a venture-backed startup in Richmond in January of 2024, he noticed how few senior roles existed in his region, then pulled the merger and acquisition databases to find out why. He discovered that 87 percent of external buyers in Roanoke, and 82 percent across Virginia, were from out of state, which meant companies and their leadership kept leaving. The research he found showed that a locally headquartered company recirculates roughly 52 to 53 cents of every revenue dollar in its community, a figure that falls to about 14 cents once the headquarters moves to a larger city. That gap became the foundation for Harbor. TRUST AS THE ONLY CURRENCY: Andrew closed the conversation on a theme he keeps returning to. Trust, he argued, is the one thing that holds when assets turn and revenue streams dry up, and he sees it as underdeveloped in a digital, globalized world where people invest too little in relationships. KEY INSIGHTS: Andrew's foundational insight is that owners care deeply about who becomes the next steward of what they built. He lays out three options for a seller, a strategic buyer, a private equity firm, or a buyer like Harbor that keeps the team in the town where it grew up, and owners consistently choose the path that protects the legacy. Harbor backs that up with flexible structures, using earnouts, seller financing, and varying equity so the deal fits the owner. His most timely insight is that trust outlasts any single asset or revenue stream. When tungsten prices spiked because of China and hit his machine shop, Harbor could call a congressman who came to walk the shop floor. Andrew credits relationships, built in part through writing openly on LinkedIn, for access that does not show up on a balance sheet. Perfect for owners weighing succession, investors interested in longer-hold alternatives to private equity, and anyone curious about how local ownership shapes a regional economy. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/andrewdunlap FOR MORE ON ANDREW DUNLAP: https://harbor.capital https://www.linkedin.com/in/dunlapandrew/ FOR MORE ON COREY KUPFER https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today! Episode Highlights with Timestamps [00:00:00] - Introduction and overview of Harbor [00:01:48] - Andrew's first deal, a two-for-one lawn-mowing bulk rate [00:02:42] - How he stumbled backward into building Harbor [00:05:05] - The recirculation research, 52 to 53 cents local versus 14 cents once a headquarters leaves [00:13:25] - The untimed fund and avoiding caffeinated decisions [00:21:00] - The Clark Precision Machine acquisition and the owner's five-year contract [00:34:54] - The red flags that kill a deal and the earnout bluff test [00:45:32] - Why trust is the only currency that always matters [00:49:40] - The freedom question Guest Bio Andrew Dunlap is the founder and CEO of Harbor, a holding company that buys established Virginia businesses to keep them in the state. He grew up in Baltimore, moved to Roanoke a decade ago, and came into acquisitions after coming out of a venture-backed startup in Richmond in early 2024, where he had helped build a software company with users in 60 countries. Harbor's leadership also includes M&A and securities attorney Tad Fisher and operations leader Krista Glassburn, who previously ran a manufacturing company in Tazewell, Virginia and grew it from 15 to 190 million dollars while acquiring seven companies. In its first two years, Harbor has acquired a CNC machine shop, a FINRA-registered broker dealer, and moved toward closing on an industrial services company. Show Description Do you want your business to grow faster? The DealQuest Podcast with Corey Kupfer reveals how successful entrepreneurs and business leaders use strategic deals to accelerate growth. From large mergers and acquisitions to capital raising, joint ventures, strategic alliances, real estate deals, and more, this show discusses the full spectrum of deal-driven growth strategies. Get the confidence to pursue deals that will help your company scale faster. Related Episodes Episode 328 - Richard Manders: How private equity roll-ups create value versus simply aggregating for a multiple arbitrage exit Episode 325 - Kelly Finnell: Using an ESOP as an exit that can preserve a company's independence and reward its people Episode 332 - John Martinka: Buying a business and transitioning from a corporate career into acquisition entrepreneurship Keywords/Tags Andrew Dunlap, Harbor, buy and hold holding company, keeping businesses local, Virginia acquisitions, mergers and acquisitions, business succession planning, alternative to private equity, earnouts, seller financing, deal structure, CNC machine shop, FINRA broker dealer, metal fabrication, economic recirculation, DealQuest Podcast, Corey Kupfer

From learning Mandarin with nothing but a notebook and a pen on the streets of Wuhan to losing $650,000 of his own money before ever raising outside capital, Sean Weisbrot shares hard-won lessons on cross-cultural dealmaking, bootstrapping versus fundraising, and why LinkedIn visibility now matters for founders and their teams. Sean is the founder of SparkVox, a tool that turns content executive teams are already creating into LinkedIn posts in their own voice, and the host of We Live to Build, a podcast with roughly 235,000 subscribers and more than 320 interviews with seven and eight figure brand owners. He has helped create over $100 million in value across his network and generated more than $15 million in revenue for his own businesses, all while living in China, Vietnam, and now Portugal. WHAT YOU'LL LEARN: You'll discover how a single misstep with a business card or a signing pen can cost a deal before it starts, why 320 founder interviews convinced Sean that bootstrapped founders tend to be happier than funded ones, and how a $400,000 gap between what one investor promised and delivered helped sink his last company. Sean also explains how he now runs a business on roughly $50 a month using AI, and why he believes every founder and executive needs a visible presence on LinkedIn. SEAN'S JOURNEY: Sean had no entrepreneurial role model growing up. What moved him was a pull to leave the US, and after missing a deadline for a teaching program in Japan, he landed in China instead and stayed for ten years, learning Mandarin street vendor by street vendor with a notebook and a pen. His first real deal came in 2016, connecting an American founder with a Chinese investor for a $150,000 raise and earning a $7,500 commission. From there he built a $15 million consulting business helping Chinese and Western companies raise money from each other in the blockchain space. His next venture, a tech company built to compete with Slack, taught him a harder lesson. He put in $650,000 of his own money before raising a $1 million seed round, and a $400,000 shortfall from one investor became a major factor in the company's failure. COVID and a divorce followed, which is part of what led him to Portugal for a fresh start. KEY INSIGHTS: Deal culture varies sharply across countries, down to details like how a business card is received. Corey shared a parallel story about a 1980s deal that nearly stalled at signing over missing ceremonial pens. Founder happiness tracks closely with how a company was funded. Across 320-plus interviews, Sean found bootstrapped founders were generally happier than those who raised capital. A funding gap can sink a company as fast as a bad decision can, as Sean's own $400,000 shortfall proved. AI has collapsed the cost of running a business. Sean's infrastructure now costs about $50 a month, down from roughly $1,000 a month at his last company. Visibility has become a gatekeeper for access, with investors now expecting founders to be active on LinkedIn before they'll even take a call. Perfect for founders weighing whether to bootstrap or raise capital, business leaders working across cultures on deals, and anyone trying to build an authentic presence on LinkedIn. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/seanweisbrot FOR MORE ON SEAN WEISBROT: https://www.welivetobuild.com/ https://www.linkedin.com/in/seanweisbrot/ FOR MORE ON COREY KUPFER https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today! Episode Highlights with Timestamps: [00:00:00] - Introduction and Sean's background [00:04:20] - Sean's first professional deal in China [00:09:13] - Cultural differences in dealmaking between the US and China [00:26:22] - The capital raising journey behind his last tech company [00:41:03] - What SparkVox does and who it serves [00:53:23] - What freedom means to Sean Guest Bio: Sean Weisbrot is the founder of SparkVox, which turns content executive teams are already creating, sales calls, internal trainings, podcast appearances, into LinkedIn posts in their own voice. He is also the host of We Live to Build, a podcast with roughly 235,000 subscribers and more than 320 interviews with seven and eight figure brand owners. Sean has helped create over $100 million in value across his network, generated more than $15 million in revenue for his own businesses, and raised over $8 million for his businesses and clients. He has angel invested in nine companies with two exits. Fluent in Mandarin, he lived in China for ten years and Vietnam for five before settling in Portugal, where he now lives with his family. Related Episodes: Episode 337 - Jonathan Gardner: Cultural due diligence and what gets lost in translation across German, Japanese, and Chinese deals Episode 370 - Gerry Hays: Democratizing venture capital and when founders should raise versus bootstrap Episode 350 - Tom Dillon: When NOT to take venture capital money and alternative funding sources Keywords/Tags: Cross-cultural dealmaking, bootstrapping versus venture capital, LinkedIn content strategy, AI-powered content creation, blockchain fundraising, founder visibility, personal branding, remote entrepreneurship, cultural due diligence, capital raising

From buying the casting agency that represented her as a teenage actor at age twenty to being involved in more than forty M&A transactions, Victoria Pelletier shares why joint ventures run their course, what six acquisitions in eighteen months taught her about integration, and why 70 percent of deal value comes down to people and process. Victoria is a keynote speaker, published author, board director, and transformational executive with more than twenty years of leadership experience at major companies such as IBM and American Express. Her self-described nickname is the turtle, tough on the outside, a marshmallow on the inside. WHAT YOU'LL LEARN: You'll discover why joint ventures can end without anything going wrong, how patient trust-building saved a 250 million dollar client portfolio during an acquisition streak, why only 10 percent of AI value comes from the algorithms while 70 percent comes from people and process, and why no company Victoria has seen has truly moved past proof of concept to enterprise-level AI. VICTORIA'S JOURNEY: Victoria bought her first company at age twenty, paying around ten thousand dollars for the casting agency that represented her and selling it about eighteen months later. She went on to a publicly traded corporate travel company that ended a joint venture, went public, and acquired six companies in eighteen months, with Victoria involved from due diligence through integration. She has since built and sold a natural bath and body company, published four books with a fifth arriving later this year, and now focuses on speaking, AI advisory work, and executive coaching. KEY INSIGHTS: People drive most of the value in any deal. Victoria cites a BCG finding that only 10 percent of AI value comes from the algorithms, 20 percent from data and technology, and 70 percent from people and process, a ratio she sees play out in deals everywhere. During her acquisition streak, she spent almost a year winning the trust of a woman thirty years her senior who ran a 250 million dollar client portfolio rather than restructuring her out, and that woman became one of her biggest cheerleaders. Due diligence is where deals most often go wrong, a lesson Victoria learned firsthand when a seller misrepresented a business and she had to sue. And someone must own the value after closing, which is why she built a value realization office at her last company. Her philosophy through it all comes down to choice. "I do not do things personally or professionally that don't bring me joy or value." Perfect for business owners considering their first acquisition, leaders navigating post-deal integration, and anyone interested in the people side of deal-driven growth. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/victoriapelletier FOR MORE ON VICTORIA PELLETIER: www.victoria-pelletier.com https://youtu.be/xFpknOCFMOg FOR MORE ON COREY KUPFER https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today! Episode Highlights with Timestamps [00:00:00] - Introduction and overview [00:02:26] - Buying the casting agency that represented her at age twenty [00:12:07] - The 250 million dollar client portfolio she almost restructured [00:21:29] - The acquisition that went poorly and ended in a lawsuit [00:39:50] - Why no one is doing AI at enterprise scale yet [00:43:08] - What freedom means to Victoria Guest Bio Victoria Pelletier is a keynote speaker, published author, board director, and transformational executive with more than twenty years of leadership experience, including roles at major companies such as IBM and American Express. She has been involved in more than forty M&A transactions along with joint ventures and her own acquisitions and exits. Known for her no excuses philosophy, she helps organizations and professionals develop stronger leadership skills, build personal brands, embrace diversity and inclusion, and create lasting professional success. Her fourth book came out earlier this year and her fifth arrives later this year, covering personal branding, leadership, culture, and career transitions. Related Episodes Episode 293 - Sunny Vanderbeck: Long horizon value creation and building businesses that deserve to last Episode 330 - Pete Mohr: Building an exit-ready business and understanding what your company is actually worth Episode 366 - Jodi Hume: Founder decision-making and the emotional journey behind major business decisions Keywords/Tags M&A integration, joint ventures, due diligence, post-merger integration, people and process, value realization office, corporate travel company acquisitions, personal branding, leadership, no excuses philosophy, women in leadership, executive coaching, AI adoption, enterprise AI, transformational executive, deal-driven growth

After more than 400 episodes across eight years, Corey Kupfer launches a new quarterly roundtable with his law firm partners Brian Meegan and Sara Mostafa (together representing roughly 90 years of combined deal experience) to unpack why the projected 2026 M&A boom has not fully arrived, revisit the negotiation tactics behind the 1951 Korean War armistice, and share parting wisdom for business owners in a slower market. In this episode of the DealQuest Podcast, host Corey Kupfer launches a new quarterly roundtable format with his law firm partners, Brian Meegan and Sara Mostafa. Brian has been a partner for several years. Sara joined this year as the newest partner. Together the three represent about 90 years of combined deal experience across M&A, capital raises, cross-border transactions, and wealth management. WHAT YOU'LL LEARN You'll discover why the pent-up M&A demand projected for 2026 has not materialized as expected, how a Virginia-focused fund is challenging the assumption that acquisitions drain leadership talent out of state, and why wealth management continues to run counter to the broader slowdown. Brian and Sara explain what a $60 billion all-stock transaction involving AnySphere signals about AI M&A, what the 1951 Korean War armistice negotiations still teach modern dealmakers, and how a post-Soviet Russian deal turned on cultural understanding rather than a legal provision. THE FIRM'S JOURNEY TO A QUARTERLY ROUNDTABLE The DealQuest Podcast has run for eight years and passed 400 episodes with a rhythm of three guest interviews followed by a solocast. Brian Meegan joined the firm a few years ago as a partner and has appeared on the show as a guest a couple of times. Sara Mostafa joined this year as the newest partner and has also appeared as a guest since coming on board. With three partners now representing roughly 90 years of combined deal experience, Corey launched this quarterly roundtable to talk deals openly, share what each partner is seeing across their practice areas, and introduce a new Deals in History segment. DEALS IN HISTORY Brian opened the first installment of Deals in History with the 1951 Korean War armistice negotiations, which contained nearly every classic tactic anyone has ever written about. The North Koreans picked up the UN delegation in cars carrying white flags, used higher chairs to gain physical advantage, and pushed multi-meeting standoffs over table shape and flag size. At one point both sides sat in complete silence for over two hours, refusing to move on a single boundary point. The full negotiation spanned roughly 160 meetings across two and a half years, and the document that resulted is not a peace treaty. It is a ceasefire that has held since the end of the war. KEY INSIGHTS The pent-up 2026 M&A demand has not arrived. Energy price disruption, interest rate uncertainty, and other macro conditions have kept the big bump from showing up. Deal flow remains active, but both Brian and Sara noted a less frenetic pace toward closing. Wealth management remains a meaningful exception, with private equity capital and succession pressure keeping RIA deal flow robust. Outside wealth management, Sara is seeing active smaller and mid-market activity, especially for targets that have successfully integrated AI into operations. Andrew Dunlap's Virginia-focused fund is a useful counterweight to the standard acquisition narrative. He shared with Corey that 82 percent of Virginia acquisition buyers were from out of state, and top leadership talent tends to relocate with the new HQ. His commitment is to keep businesses local, in a mini Berkshire Hathaway style approach. Cultural understanding often matters more than a specific legal provision. Corey shared a story from the early 1990s, just after the Soviet Union fell, when a Russian counterparty refused to sign a standard non-circumvention agreement as a matter of deeply held belief. Corey structured around it by locking up non-circumvention agreements with the US suppliers directly, and closed the deal. There is a deal for almost any business frustration, challenge, or opportunity. Corey's parting wisdom points to acquihires, joint ventures, strategic alliances, and white labeling as underused options. Brian added Jim Collins' 2009 line to never waste a good recession. Sara closed with practical guidance for women-owned and minority-owned business owners to seek community and specialized funds beyond the SBA. Perfect for entrepreneurs weighing M&A moves right now, wealth management and RIA professionals tracking deal flow, and anyone interested in how experienced deal lawyers read the market quarter to quarter. FOR MORE ON THIS EPISODE https://www.coreykupfer.com/blog/quarterly-roundtable-brian-meegan-sara-mostafa FOR MORE ON KUPFER. https://www.kupferlaw.com FOR MORE ON COREY KUPFER https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today! Episode Highlights with Timestamps [00:00:00] - Launching the new quarterly roundtable format with Brian Meegan and Sara Mostafa [00:05:13] - Sara on smaller and mid-market deal activity, especially where AI is integrated [00:09:18] - Andrew Dunlap's Virginia fund and the 82 percent out-of-state buyer statistic [00:11:24] - Space industry multiples running hot alongside AI [00:14:09] - The $60 billion all-stock transaction involving AnySphere and Cursor [00:15:04] - Deals in History debut, the 1951 Korean War armistice negotiations [00:20:26] - Walking the Abraham Path with William Ury in 2017 [00:23:32] - Corey's post-Soviet Russian deal and the non-circumvention agreement story [00:28:17] - Cross-border capital flow from the Middle East, India, and China [00:36:22] - Parting Shots from Sara, Brian, and Corey Guest Bios: Brian Meegan has represented US and multinational clients on corporate matters for more than 25 years, primarily on M&A, business formation, contract negotiation, and real estate. Before joining Kupfer, he founded Evergent Law, listed in Best Law Firms in America (Colorado) for Corporate Law and the exclusive Colorado M&A firm in the IR Global network, and he separately founded Watson Ltd., a back-office support company serving law firms nationwide. Brian earned his B.S. and J.D. from the University of Colorado, is listed in Best Lawyers in America (Colorado), and is a self-described history nerd who powers the new Deals in History segment on the show. Sara Mostafa is a corporate attorney with nearly two decades of experience representing private companies and individuals across M&A, private equity, financing, corporate governance, employment, real estate, and outside general counsel work, with clients spanning technology, wealth management, retail, entertainment, construction, restaurants, medical practices, and fitness and nutrition. She began her practice at Cooley LLP in San Diego and later served as a Partner at Lobb & Plewe LLP before joining Kupfer. Sara earned her J.D. from UCLA School of Law and her B.A. magna cum laude from the University of Pennsylvania, completed Harvard Law School's Executive Education program in M&A in 2023, and is licensed in California and Hawaii. She speaks English, Spanish, Arabic, and French Host Bio: Corey Kupfer is an expert strategist, negotiator, and dealmaker with more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker deeply passionate about deal-driven growth. He is the creator and host of the DealQuest Podcast. Show Description: Do you want your business to grow faster? The DealQuest Podcast with Corey Kupfer reveals how successful entrepreneurs and business leaders use strategic deals to accelerate growth. From large mergers and acquisitions to capital raising, joint ventures, strategic alliances, real estate deals, and more, this show discusses the full spectrum of deal-driven growth strategies. Get the confidence to pursue deals that will help your company scale faster. Related Episodes: Episode 351 - There's a Deal for That Episode 331 - M&A Market Outlook and Deal Predictions Episode 293 - Sunny Vanderbeck, Selling Without Selling Out Keywords/Tags: DealQuest quarterly roundtable, Brian Meegan, Sara Mostafa, Corey Kupfer, 2026 M&A market, wealth management M&A, RIA deal flow, AI acquisitions, AnySphere Cursor, mid-market deals, cross-border transactions, Korean War armistice negotiation, William Ury, post-Soviet dealmaking, Andrew Dunlap Virginia fund, mini Berkshire Hathaway, non-circumvention agreement, deal-driven growth, Kupfer Associates, private equity M&A

From co-managing the Odwalla IPO at Van Kasper & Company to raising $100 million with Lehman Brothers for a Pacific Northwest workers comp captive when insurance was unavailable at any price, David Horwich shares why thinking like a buyer, understanding the three ways to grow a business, and building optionality matter more than chasing any specific exit. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with David Horwich, the founder of Horwich Strategic Advisors (HSA) in Los Angeles. David spent 13 years at Van Kasper & Company before its 1999 sale, retired from banking in 2010, and spent nearly nine years at GHJ before spinning out his own firm about a year ago. Across his four decade career he has been exposed to somewhere between 5,000 and 5,500 companies. WHAT YOU'LL LEARN: Why running a market check with five investment banking firms and five private equity groups produces a real world valuation, how the three ways to grow apply to almost any company, and why selling new stuff to existing customers is by far the easiest path. David also shares how the workers comp captive he raised $100 million for is still operating today. DAVID'S JOURNEY: After economics at UC San Diego and an MBA at Berkeley, David spent five years at a transportation equipment leasing business in San Francisco. He then joined Bruce Emeluth as the first hire at Van Kasper & Company, where he stayed 13 years and chaired the firm's fairness opinion committee. Van Kasper was sold in 1999 to a bank out of Salt Lake City that Wells Fargo later acquired, making the group the first incarnation of Wells Fargo Securities in the fall of 2000. David left in 2003, retired from banking in 2010, spent nearly nine years at GHJ, and spun out Horwich Strategic Advisors about a year ago. KEY INSIGHTS: Not all revenue is created equal. Repeatable revenue beats one-off revenue. Higher margin beats lower margin. Revenue that requires no working capital beats revenue that ties it up. Most owners street fight for the next million dollars of revenue without asking whether it is good revenue or bad. There are three ways to grow a business and the second is easiest by far. Sell what you have to more customers. Sell new stuff to existing customers. Sell new stuff to new customers. David is emphatic that you should almost never attempt the third. Existing customers have already crossed the Rubicon with you, so every cost is lower. Build optionality before you build an exit plan. Before running any analysis for owners unsure what to do, David sends them to their investment advisor to get their financial goals clear first. Then he outlines every alternative. Keep it. Sell it. Recapitalize it. Gift some but not all. The toolkit is small, but choosing well requires clarity first. Perfect for privately held business owners who want to know what their company is actually worth, entrepreneurs weighing whether to buy or build, and leaders in a transition moment who need optionality before an exit. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/davidhorwich FOR MORE ON DAVID HORWICH: Website: https://horwichadvisors.com LinkedIn: https://www.linkedin.com/in/david-horwich-9317b56/ FOR MORE ON COREY KUPFER https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today! Episode Highlights with Timestamps [00:00:00] - Introduction and overview [00:02:42] - Chairman's bag carrier and the waste coal project in Hardin, Montana [00:06:22] - Joining Bruce Emeluth as first hire at Van Kasper & Company [00:11:52] - The Odwalla IPO at $8 a share and the E. coli tragedy [00:24:11] - Exposure to somewhere between 5,000 and 5,500 companies [00:35:26] - The market check and the four questions [00:48:00] - The $100 million workers comp captive with Lehman Brothers [00:50:41] - What freedom means to David Guest Bio David Horwich is the founder of Horwich Strategic Advisors (HSA), a Los Angeles based firm focused on maximizing the value of privately held businesses. He runs market checks that produce real world valuations, builds strategic growth plans, and helps owners think like buyers before any transaction. He has been exposed to somewhere between 5,000 and 5,500 companies across his four decade career. After economics at UC San Diego and an MBA at Berkeley, David spent five years at a transportation equipment leasing business in San Francisco before joining Bruce Emeluth as the first hire at Van Kasper & Company, where he stayed 13 years. Van Kasper was sold in 1999 and became the first incarnation of Wells Fargo Securities in the fall of 2000. David retired from banking in 2010, spent nearly nine years at GHJ, and spun out his own practice about a year ago. Host Bio Corey Kupfer is an expert strategist, negotiator, and dealmaker with more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker deeply passionate about deal-driven growth. He is the creator and host of the DealQuest Podcast. Show Description Do you want your business to grow faster? The DealQuest Podcast with Corey Kupfer reveals how successful entrepreneurs and business leaders use strategic deals to accelerate growth. From large mergers and acquisitions to capital raising, joint ventures, strategic alliances, real estate deals, and more, this show discusses the full spectrum of deal-driven growth strategies. Get the confidence to pursue deals that will help your company scale faster. Related Episodes Episode 330 - Pete Mohr: Building an exit-ready business and understanding what your company is actually worth Episode 332 - John Martinka: Exit with style, grace, and more money Episode 293 - Sunny Vanderbeck: Long horizon value creation and building businesses that deserve to last Episode 350 - Tom Dillon: Capital strategy, alternative funding sources, and when not to take venture money Social Media Follow DealQuest Podcast: LinkedIn: https://www.linkedin.com/in/coreykupfer/ Website: https://www.coreykupfer.com/ Follow David Horwich: Website: https://horwichadvisors.com LinkedIn: https://www.linkedin.com/in/david-horwich-9317b56/ Keywords/Tags investment banking, growth consulting, exit planning, market check, three ways to grow a business, think like a buyer, enterprise value, middle market M&A, Van Kasper & Company, Odwalla IPO, private equity, capital raising, business valuation, optionality, strategic growth planning, buy versus build, workers comp captive, privately held businesses, Los Angeles M&A advisor, deal-driven growth

From buying his first fourplex in Albuquerque for $117,000 to helping build a portfolio of more than 2,700 apartment units and 100,000 square feet of industrial real estate, Jens Nielsen shares why hiring property management on day one, picking the right investors, and getting visionary owners out of their own way matter more than chasing the next deal. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with Jens Nielsen, a commercial real estate investor, operator, and business coach based in Santa Fe, New Mexico. Jens spent 27 years in IT and telecom before transitioning to full-time real estate investing, raising over $10 million in private capital across more than thirty deals. He now works with entrepreneurs across industries to improve execution, leadership, and scalability. WHAT YOU'LL LEARN: Why hiring property management before closing your first deal can save your sanity, how to spot the wrong investor before money changes hands, and why the visionary owner refusing to let go is the biggest blocker to growth in most companies. Jens also explains his pivot from multifamily to light industrial when rates climbed in 2022 and 2023. JENS' JOURNEY: After 27 years in corporate IT and telecom, his mother's passing at age 52 became the catalyst for Jens to seek freedom and disconnect his time from his income. In 2016 he bought his first commercial deal, a fourplex in Albuquerque, New Mexico for $117,000, and hired property management on day one because he lived four hours away in Colorado. His first syndication followed in 2018 with a 38-unit property and five partners. He and his partners have since built a portfolio of more than 2,700 apartment units and over 100,000 square feet of industrial real estate across multiple states. KEY INSIGHTS: Pay attention to investor temperament before money hits the account. One of Jens's first syndication partners wanted more control than he had and freaked out at every financial report. After six months, Jens bought him out so they could both sleep at night. His lesson is direct. If you have to convince someone to invest, that is not a yes. Do enough deals to let the law of large numbers work for you. One of his properties returned 350 percent. Another lost money entirely. If you put everything into one deal, you are gambling, not investing. The visionary owner not letting go is the biggest growth blocker in most companies. Jens has applied the same operational fix across gyms, property management firms, bakeries, a law firm, and an auto shop. The industries change. The bottleneck does not. Perfect for first-time real estate investors trying to avoid the second-job trap, experienced syndicators thinking through investor selection, and entrepreneurs who have hit a growth ceiling because they cannot get out of their own way. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/jensnielsen FOR MORE ON JENS NIELSEN: https://www.jensnielsen.us https://www.facebook.com/coachjens https://www.linkedin.com/in/jenswnielsen/ FOR MORE ON COREY KUPFER https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today! Episode Highlights with Timestamps [00:00:00] - Introduction and overview [00:03:06] - First fourplex in Albuquerque for $117,000 [00:04:10] - Mother's passing at 52 as the catalyst [00:08:03] - Hiring property management on day one [00:10:37] - The first 38-unit syndication in 2018 [00:15:02] - Buying out a nervous investor partner [00:26:31] - The visionary owner not letting go [00:40:36] - Pivoting into light industrial and flex space [00:44:24] - What freedom means to Jens Guest Bio Jens Nielsen is a commercial real estate investor, operator, and business coach based in Santa Fe, New Mexico. After a 27-year career in IT and telecom, he transitioned to full-time real estate investing and helped build a portfolio of more than 2,700 apartment units and over 100,000 square feet of industrial real estate. He has raised over $10 million in private capital and has firsthand experience navigating acquisitions, operational scaling, investor communications, and market downturns. His focus is on what happens after the deal closes. Originally from rural Denmark, Jens moved to the United States thirty years ago. He bought his first commercial property, a fourplex in Albuquerque, New Mexico, in 2016 and built his portfolio through more than thirty per-deal syndications across multiple states. Today he works with entrepreneurs and operators across industries, including gyms, property management companies, bakeries, a law firm, and an auto shop, helping them improve execution, leadership, and scalability so growth creates freedom instead of chaos. Host Bio Corey Kupfer is an expert strategist, negotiator, and dealmaker with more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker deeply passionate about deal-driven growth. He is the creator and host of the DealQuest Podcast. Show Description Do you want your business to grow faster? The DealQuest Podcast with Corey Kupfer reveals how successful entrepreneurs and business leaders use strategic deals to accelerate growth. From large mergers and acquisitions to capital raising, joint ventures, strategic alliances, real estate deals, and more, this show discusses the full spectrum of deal-driven growth strategies. Get the confidence to pursue deals that will help your company scale faster. Related Episodes Episode 338 - Joel Miller: Real estate investing, rental property wealth, and hard money lending Episode 328 - Richard Manders: Free Scale Coaching and helping founders build businesses that scale beyond them Episode 336 - Devan Gonzalez: The visionary and integrator dynamic in growing entrepreneurial companies Episode 350 - Tom Dillon: Capital strategy, alternative funding sources, and when not to take venture money Keywords/Tags: commercial real estate, real estate syndication, multifamily investing, light industrial real estate, flex space, property management, raising private capital, accredited investor strategy, IT career transition, working on the business, visionary bottleneck, EOS implementation, E-Myth, business coaching, scaling small businesses, Albuquerque real estate, Pennsylvania real estate, owner-operator real estate, real estate fundamentals, entrepreneurial freedom

From a childhood dream of becoming an inventor like Louis Pasteur to leading commercial due diligence for private equity funds like KKR and HIG, Josh Emington shares how his team sizes markets, calls real customers, and spots the growth opportunities other investors miss. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with Josh Emington, a partner at The Martec Group, a boutique strategic consulting and market research firm. Josh leads Martec's value creation team, working with lower middle market and middle market private equity funds including KKR, HIG, Granite, Rotunda Capital, and Everglades Equity. WHAT YOU'LL LEARN How commercial due diligence tests whether a deal's growth story actually holds up, why customer concentration can erase a company overnight, and what a free pre-diligence memo can flag before a client spends real money. Josh also explains why his team still picks up the phone to call a target's real customers, and how AI has compressed Martec's research timelines from seven days to two. JOSH'S JOURNEY Josh's path into research started at a scholastic book sale, where his parents picked up a chemistry kit and a book about Louis Pasteur. He decided he wanted to be an inventor who saved lives the way Pasteur had. His first real deal came as an Eagle Scout, selling popcorn door to door to earn a trip. The professional turning point came on a customer journey project for a top manufacturer of toilet seats. When his team learned that customers had no idea who to call when a seat broke, they recommended putting the brand name on the back. Two years later Josh saw the brand on a hotel toilet seat and, as he told Corey, "just making an impact in a business like that doesn't get any better." Over the past decade Josh has executed hundreds of global research and consulting engagements at Martec, focused on commercial due diligence, M&A funnel support, target identification, and customer due diligence anchored in primary research. KEY INSIGHTS Commercial due diligence looks at both the risks that could blow up a deal and the opportunities a buyer might be paying for without realizing it. Josh shared a southern Florida example where his team helped a client acquire a lawn care installation business alongside a separate maintenance company, turning one time jobs into recurring revenue. Skipping pre-diligence is a common mistake. At least three times a year, Josh's team will deliver a short, free memo that sometimes recommends an investor not proceed at all because a technology is about to obsolesce or a competitor is far more advanced than the marketing suggests. Customer concentration is the biggest single risk Josh's team flags. As he put it, if 10 customers or even one customer accounts for 70 percent of revenue and that relationship ends, you do not have a company anymore. Corey pushed back from his seller side perspective, arguing buyers should consider structural protections tied to retention rather than discounting valuation outright. About 10 percent of Josh's M&A work happens on the sell side through exit planning. In one engagement, his team interviewed 2,000 rug buyers for an upper middle market online rug company to give a skeptical buyer the confidence that the brand really commanded its prices. AI has also compressed Martec's research timelines from seven days to two, and Josh's team now applies a triple AI lens to every deal, assessing how AI will affect the target's market, its workforce, and its own customers. Perfect for private equity investors, business owners preparing for sale, and dealmakers who want to understand what really gets tested before a deal closes. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/joshemington FOR MORE ON JOSH EMINGTON: Website: https://martecgroup.com/ LinkedIn: https://www.linkedin.com/in/joshemington/ FOR MORE ON COREY KUPFER https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Episode Highlights with Timestamps [00:00:02] - Introduction and Josh's background at The Martec Group [00:03:21] - The toilet seat project that made Josh fall in love with research [00:09:01] - The southern Florida lawn care deal that turned one time jobs into recurring revenue [00:13:39] - The free pre-diligence memo that can stop a bad deal before it starts [00:16:04] - The last bastion of human value and how customer due diligence really works [00:23:13] - Sizing the prize and spotting customer concentration risk [00:38:46] - How AI has compressed research timelines from seven days to two [00:46:56] - What freedom means to Josh Guest Bio Josh Emington is a partner at The Martec Group, a boutique strategic consulting and market research firm serving private equity funds and Fortune 1000 leaders. Over the past decade he has led hundreds of global research and consulting engagements focused on commercial due diligence, M&A funnel support, target identification, and customer due diligence anchored in primary research. He leads Martec's value creation team, supporting clients from thesis validation through pre-LOI and into post close growth strategy. Publicly known clients include KKR, HIG, Granite, Rotunda Capital, and Everglades Equity. Host Bio Corey Kupfer is an expert strategist, negotiator, and dealmaker with more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker deeply passionate about deal-driven growth. He is the creator and host of the DealQuest Podcast. Show Description Do you want your business to grow faster? The DealQuest Podcast with Corey Kupfer reveals how successful entrepreneurs and business leaders use strategic deals to accelerate growth. From large mergers and acquisitions to capital raising, joint ventures, strategic alliances, real estate deals, and more, this show discusses the full spectrum of deal-driven growth strategies. Get the confidence to pursue deals that will help your company scale faster. Related Episodes Episode 332 - John Martinka. Financial due diligence and why messy financial statements can kill a deal or cost a seller real money on valuation. Episode 324 - Sejal Lakhani-Bhatt. Technical and cybersecurity due diligence, and how a company's IT history follows it into a sale. Episode 351 - Corey Kupfer Solocast. A breakdown of the different types of due diligence that apply across every kind of deal. Keywords/Tags commercial due diligence, private equity due diligence, customer due diligence, voice of customer research, market sizing, TAM and SAM analysis, customer concentration risk, exit planning, M&A due diligence, value creation, buy side due diligence, sell side due diligence, AI in market research, deal thesis validation, competitive market mapping, business combination strategy, recurring revenue acquisition, pre-LOI diligence, lower middle market private equity, Martec Group

From speaking at three major wealth management conferences in a single quarter to mapping out a pattern that's already reshaped accounting and is now creeping into law and the trades, Corey Kupfer breaks down the barbell effect and what business owners should be doing now to avoid getting caught in the middle. WHAT YOU'LL LEARN: In this episode, you'll discover what the barbell effect is and why it shows up across industries once consolidation and outside capital enter the picture, how accounting's shift from the Big Eight to the Big Four foreshadows what may be coming in wealth management, and why most deals positioned as mergers are actually acquisitions in disguise. Corey explains why firms stuck in the middle face higher overhead than small competitors and fewer resources than large ones, and how the same dynamic is showing up in the trades, from roofing to electrical. KEY INSIGHTS: The barbell effect describes what happens as an industry consolidates: large, well funded firms on one end, small boutique firms on the other, and the middle becoming the hardest place to operate, with higher overhead than small competitors and fewer resources than large ones. The accounting industry offers a preview of where wealth management may be headed. Corey points to the shift from the Big Eight to the Big Four, and to firms like Eisner and Amper merging to compete at a higher level, along with Apria's growth through acquisition. In legal, only attorneys can own law firms in most states, but Corey describes private equity entering through a managed services model similar to healthcare, where a non-legal company runs the back office while attorneys retain ownership of the practice. Corey shares a comment from his Entrepreneurs Organization lawyers group, that it is much easier to run a law firm under two million dollars or over ten million dollars in revenue than to be stuck in the middle, connecting this to the crossing the chasm dynamic of investing ahead of payoff. Drawing on NAPFA in Minneapolis, Corey notes many members are choosing not to sell to PE backed aggregators, even leaving value on the table, out of concern for fiduciary alignment, while noting he is relaying their perspective rather than judging it. He also points out most "mergers" are actually acquisitions, cites the 2026 Advisor Growth Strategies Report and DeVoe's data showing fewer buyers chasing more sellers and average seller AUM crossing a billion dollars, and closes by noting the same barbell dynamic in the trades, where consolidators and mom and pop firms both persist while the middle gets squeezed. Perfect for RIA owners weighing independence, succession, or sale, leaders of growing companies assessing their industry's consolidation cycle, and anyone navigating competition in the middle market. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/barbelleffect FOR MORE ON COREY KUPFER https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today! Episode Highlights with Timestamps [00:00:04] - Introduction: the barbell effect and why Corey is talking about it now [00:04:23] - The NAPFA community conversation on succession and exit options aligned with values [00:08:37] - What the barbell effect is and why the middle becomes the hardest place to compete [00:12:21] - Why it's easier to run a law firm under two million or over ten million in revenue than to be stuck in the middle [00:16:14] - NAPFA advisors and the choice to stay independent from PE backed aggregators [00:19:55] - The barbell effect in the trades: roofing, gutters, and electrical consolidation [00:21:55] - Planning for industry evolution instead of being surprised by it Host Bio Corey Kupfer is an expert strategist, negotiator, and dealmaker with more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker deeply passionate about deal-driven growth. He is the creator and host of the DealQuest Podcast. Show Description Do you want your business to grow faster? The DealQuest Podcast with Corey Kupfer reveals how successful entrepreneurs and business leaders use strategic deals to accelerate growth. From large mergers and acquisitions to capital raising, joint ventures, strategic alliances, real estate deals, and more, this show discusses the full spectrum of deal-driven growth strategies. Get the confidence to pursue deals that will help your company scale faster. Related Episodes Episode 350 - Tom Dillon: Building a firm positioned for acquisition and succession Episode 339 - Solocast 74: Building your G2 and creating optionality for internal succession Episode 331 - Solocast 72: Reading macro and industry trends without letting personal views distort business decisions Episode 327 - Solocast 71: Using authority marketing to build relationships and deal flow Keywords/Tags barbell effect, industry consolidation, RIA independence, private equity wealth management, mergers and acquisitions, internal succession planning, mergers of equals, middle market squeeze, fiduciary advisors, NAPFA, accounting industry consolidation, legal industry private equity, managed services organization, crossing the chasm, RIA exit planning, trades industry consolidation, deal driven growth, 2026 advisor growth strategies, business positioning strategy, exit strategy planning

From selling candy in school as a kid in Medellin and getting robbed by his business partner, to riding the South Florida real estate boom and losing everything in the crash before he was twenty, Alex Lopez, CPA built his understanding of deals through lived experience long before he picked up an accounting textbook. Alex runs a CPA firm specializing in CFO services and tax minimization strategy, with over 12 years of experience at global accounting and consulting firms and in corporate America. He works with entrepreneurs in professional services, tech, and real estate, focused on helping them scale from six to seven to eight figures while keeping more of their profits out of the IRS's hands. His years as a financial auditor trained him to assess a business quickly, corroborate what owners claim, and identify which direction a company is actually trending. In this episode he walks through two contrasting deals: one where understanding why a buyer was willing to stretch above market multiples revealed hidden strategic value that let his client hold firm on price, and another where a single off-ratio insurance figure that nobody fully investigated masked a multi-million dollar misrepresentation that killed the deal entirely. He also shares the story of a seller whose insistence on cash over a higher leveraged offer turned out to have nothing to do with preference and everything to do with a pending white collar conviction. On tax planning, Alex is direct: by the time a deal is under letter of intent, several of the most powerful strategies are already gone. He walks through qualified small business stock, which can allow eligible founders to exit with little to zero federal tax on the capital gain from a business sale, but only if the company was structured as a C corporation and the stock held for at least five years. He described a young tech founder who called his firm last year with the deal locked and loaded to close, and paid a seven-figure tax bill because nobody had ever told him this option existed. The conversation also covers how S corporation elections that make sense for self-employment tax purposes can create complications in deals that include rollover equity, why founders who avoided C corp status to preserve early pass-through losses often give up far more in QSBS savings than they ever gained, and how structuring payouts over time can both spread the tax bill across lower-bracket years and give sellers leverage to negotiate a higher total price. For anyone building a business with any intention of eventually selling, this episode makes one thing clear: the time to think about these questions is years before you have a buyer at the table. FOR MORE ON ALEX LOPEZ, CPA: Website: AlexLopezCPA.com FOR MORE ON COREY KUPFER: https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today! Episode Highlights with Timestamps [00:00] - Introduction: Alex Lopez's background in CFO services and tax minimization [02:54] - First deal: selling candy in school and the partner who stole everything [13:48] - Using ratios and anecdotes to spot market exuberance before it corrects [21:31] - Finding hidden value and why a buyer's motivation is negotiating leverage [28:45] - Why tax planning needs to start before there is a deal on the table [32:13] - Structuring payouts over time to spread the tax bill and negotiate better terms [44:13] - The seller whose insistence on cash pointed to a white collar conviction [49:37] - What freedom means: being oneself and at peace with one's surroundings Guest Bio: Alex Lopez, CPA is passionate about helping business owners scale, increase profits, and minimize taxes. With over 12 years of experience working at global accounting and consulting firms and in corporate America, Alex runs a CPA firm specializing in CFO services and tax minimization strategy. He works primarily with entrepreneurs in professional services, tech, and real estate. Alex grew up in Medellin, Colombia and came to the United States in 1999, getting his real estate license straight out of high school before the 2008 financial crisis redirected him toward accounting. That combination of early deal experience and deep technical expertise informs how he advises clients on both the financial and structural dimensions of their transactions. Related Episodes: Episode 350 - Tom Dillon: Business Valuation and Exit Planning Realities: Understand how valuation works in practice and what drives the gap between what owners expect and what the market will pay. Episode 330 - Pete Mohr: Building Enterprise Value and Exit Readiness: Learn how operational decisions made years before a sale determine what a business is actually worth when it goes to market. Episode 339 - Solocast 74: Equitizing Key Employees and Succession Planning Strategies: Explore how entity structure and equity decisions made early shape your options when it is time to exit.

When Jack Clark talks about building 180 Water Franchising, he focuses on one core idea: creating a replicable model in an industry that has never had one. The water well business has always been built around owner-operators — small crews, no national presence, and a retiring workforce with no clear succession path. Jack saw that gap and built the first franchise in the industry to fill it. In this episode of the DealQuest Podcast, Corey Kupfer sits down with Jack Clark, founder and owner of 180 Water Franchising, to discuss what it actually takes to franchise a skilled trades business from the ground up — and why this particular market is uniquely positioned for franchise growth. Jack breaks down the full investment and fee structure for franchisees, from the approximately $250,000 startup cost covering a fully stocked service truck to the 6% gross sales royalty, 2% brand fund, and $45,000 franchise fee. He explains why the first franchisee in each new state gets that fee waived, and why suppliers are set up with 90-day terms to ease early operations. The conversation also covers the internal dynamics of running a franchise network, including Jack's weekly Thursday calls with all franchisees, why the direction of learning inside the network has shifted from franchisor to franchisees, and what he calls the "stupid rule policy" — the principle that if a rule has to exist, the underlying system needs to change. Corey and Jack also discuss the emotional and financial reality of investing ahead of growth, including the bittersweet experience of outgrowing your original banker and building an entirely new team to support the next level of the business. This episode is packed with practical insights for entrepreneurs considering franchising as a growth vehicle, skilled trades business owners wondering whether their operation has a replicable system inside it, and anyone evaluating franchise investment opportunities in industries outside the traditional food and service categories. WHAT YOU'LL LEARN Why the water well industry is structurally positioned for franchise growth right now How Jack identified the moment his business became genuinely franchisable The full investment, fee structure, and territory model for 180 Water franchisees Why most franchisees stop worrying about having enough work within their first thirty days What the "stupid rule policy" means in practice and why it matters for franchisee satisfaction How investing ahead of growth temporarily dips profits — and why that's unavoidable Why being first in an untapped industry is a competitive moat, not a warning sign THE FIRST FRANCHISE IN THE WATER WELL INDUSTRY Jack confirmed it directly in this conversation: "No one's ever franchised the water well industry. I think a lot of guys have talked about it, but it's one of those things that until you really start to unfold it, you don't really realize how many layers there are to it." 180 Water now operates in five states with ten franchisees and is expanding nationally. When demand outpaced their Texas truck supplier, Jack didn't accept the bottleneck — he started manufacturing his own service trucks under the PumpEx Voice brand, turning a supply constraint into an entirely new business line. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/jackclark FOR MORE ON JACK CLARK Company: https://180waterfranchise.com FOR MORE ON COREY KUPFER https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker with more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where entrepreneurs and business leaders share insights, challenges, and success stories around deal-driven growth strategies. The show covers mergers and acquisitions, capital raising, strategic alliances, joint ventures, franchising, and more. Episode Highlights with Timestamps [00:00:00] - Introduction: Jack Clark and 180 Water Franchising [00:04:08] - Buying a drill rig sophomore year of college and never looking back [00:09:24] - Running four drill rigs and thirty-five employees — and being miserable [00:19:45] - Finding the first franchisee through Ranch World Ads [00:21:25] - Ten franchisees across five states and manufacturing their own trucks [00:27:37] - Why concerns about getting enough work disappear within the first thirty days [00:29:57] - Staffing ahead of growth and building a whole new team [00:46:45] - The "stupid rule policy" and why Jack would have been a terrible franchisee Guest Bio Jack Clark is the founder and owner of 180 Water Franchising, the first and only water well franchise company in the United States. After scaling the business to four drill rigs and thirty-five employees, he recognized that the pump service side of his operation had a genuinely replicable system — and launched 180 Water Franchising to bring it to the industry. 180 Water Franchising now operates in five states with ten franchisees and is expanding nationally. Jack also founded PumpEx Voice, a manufacturing company producing service trucks for the franchise network. Host Bio Corey Kupfer is an expert strategist, negotiator, and dealmaker with more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker deeply passionate about deal-driven growth. He is the creator and host of the DealQuest Podcast. Related Episodes: Episode 333 - Greg Mohr: Franchising as a Path to Financial Freedom and Wealth Building Episode 329 - Cliff Nonnenmacher: How Franchise Brokers Evaluate Systems and Match Buyers Episode 330 - Pete Mohr: Building Enterprise Value and Exit Readiness in a Service Business Keywords/Tags: water well franchise, 180 Water Franchising, Jack Clark, how to franchise a skilled trades business, franchising a service business, blue collar franchise opportunity, skilled trades franchise, franchise investment, franchise fee structure, water well industry, franchise model for entrepreneurs, franchisee success, service business scaling, first franchise in an industry, PumpEx Voice, franchise system design, franchise territory, home services franchise, trades business growth

When Omar Morillo talks about wealth management for entrepreneurs, he focuses on one core idea: reducing lifetime tax drag across income, investments, business operations, and eventual liquidity events. The earlier owners start planning, the more options they have. In this episode of the DealQuest Podcast, Corey Kupfer sits down with Omar Morillo, founder of Imperio Wealth Advisors, to discuss what sophisticated pre-exit planning actually looks like for business owners preparing for major liquidity events. Omar breaks down the three levels of tax-aware investing, from simple ETF investing to direct indexing and long-short strategies designed to generate capital loss carryforwards for future gains. He explains why many of the best planning opportunities disappear once an LOI is on the table and why advanced preparation matters. The conversation also explores estate planning, donor advised funds, PPLI structures, and the risks of “flavor-of-the-month” tax strategies that are often oversold to entrepreneurs. Corey and Omar also discuss the emotional side of exits, including why many founders struggle with identity and anxiety after selling the business that defined their lives for years. This episode is packed with practical insights for entrepreneurs thinking about exits, recapitalizations, succession planning, or long-term wealth strategy. WHAT YOU'LL LEARN Why reducing lifetime tax drag requires planning years before an exit The differences between ETF investing, direct indexing, and long-short strategies How carry-forward capital losses may help offset future gains Why estate planning and liquidity planning matter before a sale The risks and realities of structures like PPLI and QSBS Why founders often struggle emotionally after successful exits OMAR'S JOURNEY Omar Morillo originally planned to become an airline pilot before eventually finding his way into wealth management. Today, he is the founder of Imperio Wealth Advisors, where he advises entrepreneurs and families on tax strategy, liquidity planning, investments, and long-term wealth management. He approaches advisory work through what he calls an “agnostic lens,” focusing on the right strategy for the client rather than attachment to any single product or structure. FOR MORE ON THIS EPISODE https://www.coreykupfer.com/blog/omarmorillo FOR MORE ON OMAR MORILLO LinkedIn: https://www.linkedin.com/in/omarmorillo/ Company: https://www.imperiowealthadvisors.com FOR MORE ON COREY KUPFER https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker with more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where entrepreneurs and business leaders share insights, challenges, and success stories around deal-driven growth strategies. The show covers mergers and acquisitions, capital raising, strategic alliances, joint ventures, succession planning, and more. Episode Highlights with Timestamps [00:03:00] - Omar's background and accidental entry into wealth management [00:09:15] - The four layers of lifetime tax drag [00:16:40] - Why pre-exit planning must begin years before an LOI [00:22:10] - The three levels of tax-aware investing [00:30:45] - Direct indexing versus long-short strategies [00:38:20] - PPLI structures and investor control concerns [00:45:50] - The Miami Dolphins estate planning example [00:50:15] - Donor advised funds and charitable planning [01:02:00] - Omar's definition of freedom and legacy Guest Bio Omar Morillo is the founder of Imperio Wealth Advisors, a boutique wealth management firm serving entrepreneurs, business owners, and families navigating liquidity events, tax strategy, investment management, and long-term financial planning. He is a Certified Financial Planner (CFP), Accredited Investment Fiduciary (AIF), and Chartered Financial Consultant (ChFC). Omar specializes in helping clients reduce lifetime tax drag through coordinated strategies involving portfolio management, estate planning, charitable planning, and pre-exit structuring. His clients are typically entrepreneurs and business owners with substantial wealth concentration and upcoming liquidity events. Host Bio Corey Kupfer is an expert strategist, negotiator, and dealmaker with more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker deeply passionate about deal-driven growth. He is the creator and host of the DealQuest Podcast. Related Episodes Dave Hersh: Founder Identity and the Emotional Impact of Exits DealQuest Wealth Management Series with RIA Industry Acquirers Tom Dillon: Understanding Business Valuation and Exit Planning Realities Keywords/Tags pre-exit tax planning, wealth management for entrepreneurs, direct indexing, long-short investing, PPLI, private placement life insurance, donor advised funds, estate planning, liquidity event planning, tax-aware investing, founder psychology, business exits, capital gains planning, ILIT, QSBS, entrepreneur wealth strategy

From sketching fashion designs as a kid to leading complex M&A and private equity deals, Sara Mostafa shares what separates true dealmaking attorneys from ordinary transactional lawyers, why minority investment deals are like marriages with prenups, and what founders should understand before bringing in growth capital. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with Sara Mostafa , the newest partner at Kupfer. Sara has spent more than two decades representing private companies and entrepreneurs across M&A, financing, private equity, governance, employment, real estate, and outside general counsel matters. Like Corey, she came out of big law and built a relationship-first practice that supports clients from inception through exit. WHAT YOU'LL LEARN: In this episode, Sara explains what separates a true dealmaking attorney from an ordinary transactional lawyer, why minority investment deals require “eyes wide open,” and how experienced attorneys balance legal risk against business upside without over-lawyering. She also discusses why AI-related transactions are dominating parts of the California M&A market, why dental and medical practices are commanding strong multiples, what the 2008 recession taught her about resilience and pivoting, and how long-term client relationships often evolve into serving the next generation of entrepreneurs. GUEST'S JOURNEY: Sara originally wanted to be a fashion designer, inspired by her aunt and her childhood love of sketching clothes. While studying at the University of Pennsylvania, she unexpectedly completed her degree requirements early and took a paralegal role at Drinker Biddle & Reath in Philadelphia, which inspired her to pursue law school. She began her legal career at Cooley in San Diego, working on biotech M&A deals before deciding big law was not the long-term fit she wanted. During the 2008 Great Recession, she pivoted to immigration law and nonprofit work in Hawaii before returning full-time to business transactions. She remains licensed in both California and Hawaii. THE DESIGNER DEALMAKER: Outside of law, Sara continues to pursue creative work. Last year she bought a sewing machine and now spends much of her free time designing and making clothes, including garments she is exhibiting at the San Diego County Fair. Like others at Kupfer, she believes building a successful legal career does not require abandoning personal passions or entrepreneurial pursuits. KEY INSIGHTS: A true dealmaking attorney focuses on helping both sides move forward rather than over-lawyering every issue. Business-mindedness, perspective, and the ability to negotiate practical middle ground matter as much as technical legal skill. Minority investment deals can dramatically change how founders operate. Investors often require approval rights over major decisions and expect a future exit, which means founders need to fully understand both the growth opportunity and the downside risk. Sara believes lawyers must balance risk against opportunity. Businesses cannot grow without taking risks, and experienced attorneys help clients evaluate likelihood and impact rather than simply redlining every possible issue. She also explains that curiosity and adaptability matter more than narrow industry specialization in most transactional work. Over her career, she has represented clients across industries ranging from restaurants and fitness centers to technology, healthcare, entertainment, and construction. Perfect for founders considering outside capital, business owners planning an exit, and entrepreneurs evaluating whether their attorney is truly helping get deals done or simply executing documents. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/saramostafa FOR MORE ON SARA MOSTAFA: https://www.kupferlaw.com/ https://www.linkedin.com/in/sara-mostafa-02404211/ FOR MORE ON COREY KUPFER: https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today! Episode Highlights with Timestamps: [00:00:03] Introduction: Sara Mostafa's two decades of transactional experience and her arrival as the newest partner at Kupfer [00:03:28] The sewing machine bought last September and exhibiting garments at the San Diego County Fair [00:08:12] Why transactional work appealed and the value of staying with clients through the full business life cycle [00:17:45] The 2008 Great Recession as the only real slowdown and pivoting to Hawaii [00:23:46] Minority investment deals as marriages with prenups [00:29:41] What separates a real dealmaker from a transactional attorney [00:38:43] What client trust really means to Sara [00:43:11] The children of exited clients calling her for their own ventures [00:45:28] What freedom means: peace of mind Guest Bio: Sara Mostafa is a partner at Kupfer with over two decades of experience representing private companies and individuals across a wide range of transactional matters. Her practice encompasses contract negotiation, entity formation, corporate governance, mergers and acquisitions, private equity transactions, financing transactions, employment matters, real estate transactions, and outside general counsel services. She has represented companies in technology, wealth management, retail, entertainment, wholesale, construction, restaurants, medical practices, marketing, fitness, and nutrition, among others. Host Bio: Corey Kupfer is an expert strategist, negotiator, and dealmaker with more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker deeply passionate about deal-driven growth. He is the creator and host of the DealQuest Podcast. Related Episodes: Episode 293 - Sunny Vanderbeck: Building Relationships and Selling With Purpose Episode 350 - Tom Dillon: Understanding Business Valuation and Exit Planning Realities Episode 366 - Jodi Hume: Founder Exits and the Emotional Journey Behind Major Decisions Keywords/Tags: M&A counsel, transactional attorney, dealmaking attorney, minority investment deals, private equity transactions, outside general counsel, California M&A market, AI valuations, dental practice multiples, medical practice multiples, Kupfer Law partner, big law transition, exit preparation, business life cycle counsel, relationship-driven dealmaking, risk versus upside, over-lawyering, corporate governance, entity formation, capital raising, next generation clients, peace of mind freedom

From experiencing an acquisition early in his career when the AT&T division he worked for was sold to a UK private equity firm, to time at $4 billion Scotts Miracle-Gro where the company created what it called the Integration Factory, Mark Sims shares 25 years of insights on why post-deal integration often determines whether M&A deals succeed or fall short, and why integration planning has to start during due diligence. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with Mark Sims, managing principal of technology solutions at Consult MSG. Mark applies 25 years of experience in strategy, M&A, and information technology across consumer products, retail, manufacturing, and private equity. He has held roles as CEO, Head of Strategy, and CIO, and now leads the technology solutions practice at a firm built around helping middle market PE-backed companies transact, transition, and transform. WHAT YOU'LL LEARN: You'll discover why post-deal integration often determines whether M&A deals succeed or fall short, why integration planning needs to start during due diligence, and what founders selling to private equity should expect when they suddenly have a boss after decades of being the boss. Mark also explains why companies trying to implement AI keep wanting to start at step five before doing the foundational data work. MARK'S JOURNEY: Mark wanted to be an architect as a kid but pursued engineering instead, earning his bachelor's and master's in Industrial Engineering. He started his career in consulting working with Fortune 500 clients, then spent about 15 years at Scotts Miracle-Gro working in corporate M&A at the $4 billion company. About three years ago he moved into the PE advisory space full time. Mark also completed the Advanced Management Program at The Wharton School. THE INTEGRATION ARCHITECT: Mark has lived all three sides of the typical PE deal. Early in his career, he watched a UK private equity firm take over the small AT&T division he worked for, eventually moving headquarters from Cleveland to Houston where the new CEO lived. At Scotts Miracle-Gro, he worked on corporate M&A and was part of the team that created what it called the Integration Factory to snap acquired businesses into the mothership. Today he advises PE-backed middle market companies on building the integration capacity their acquisition pace demands. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/marksims FOR MORE ON MARK SIMS: Website: https://consultmsg.com/ LinkedIn: https://www.linkedin.com/in/markjsims/ FOR MORE ON COREY KUPFER: https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today! Episode Highlights with Timestamps [00:01:00] - Introduction to Mark Sims and his background [00:05:25] - Mark's career arc across public companies, Scotts Miracle-Gro, and PE advisory [00:08:54] - The founder who gets a giant check and discovers they now have a boss [00:17:32] - Why decisive integration protects the people you actually want to keep [00:22:37] - The Integration Factory at Scotts Miracle-Gro [00:29:21] - From PE to public market readiness and the standardization push [00:33:35] - Why companies want to start AI at step five before doing steps one through four [00:40:08] - What freedom means and the ability to pursue interests Guest Bio: Mark Sims is managing principal of technology solutions at Consult MSG. He applies 25 years of experience in strategy, M&A, and information technology across consumer products, retail, manufacturing, and private equity. He has held roles as CEO, Head of Strategy, and CIO, and spent about 15 years at Scotts Miracle-Gro before moving into PE advisory three years ago. Mark holds a bachelor's and master's in Industrial Engineering and completed the Advanced Management Program at The Wharton School. Host Bio: Corey Kupfer is an expert strategist, negotiator, and dealmaker with more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker deeply passionate about deal-driven growth. He is the creator and host of the DealQuest Podcast. Show Description: Do you want your business to grow faster? The DealQuest Podcast with Corey Kupfer reveals how successful entrepreneurs and business leaders use strategic deals to accelerate growth. From large mergers and acquisitions to capital raising, joint ventures, strategic alliances, real estate deals, and more, this show discusses the full spectrum of deal-driven growth strategies. Get the confidence to pursue deals that will help your company scale faster. Related Episodes: Episode 337 - Jonathan Gardner on why M&A deals fail because of culture and IT systems Episode 324 - Sejal Lakhani-Bhatt on why tech due diligence determines what you're actually buying Episode 350 - Tom Dillon on understanding business valuation and exit planning realities Episode 366 - Jodi Hume on founder exits and the emotional journey behind major business decisions Keywords/Tags: post-deal integration, M&A integration strategy, private equity portfolio companies, Scotts Miracle-Gro integration factory, founder selling to PE, middle market M&A advisory, technology integration after acquisition, ERP implementation, integration during due diligence, culture integration M&A, PE to public market readiness, AI implementation for businesses, AI policy for companies, Consult MSG, transact transition transform, corporate development integration, people money systems, PE-backed middle market, post-acquisition integration, deal-driven growth

From buying into a mismanaged family business on his mother's advice to selling at an incredibly high multiple to a PE-backed acquirer, Nate Collins shares how he built a transferable licensing company, what the post-exit "liminal period" really looks like, and why personal well-being is a greater predictor of company success than the reverse. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with Nate Collins, a former CEO who managed a successful exit of his international theatrical licensing company to a large PE-backed music licensing company. Nate now works as a financial advisor and certified exit planning advisor at Raymond James, helping business owners, CEOs, and their families navigate exits both financially and emotionally. WHAT YOU'LL LEARN In this episode, you'll discover why switching from cash to accrual-based GAAP accounting early creates enormous buyer confidence, how cloud-based systems reduced licensing time from four weeks to four hours, and what makes a business truly transferable. Nate explains the "liminal period" that researchers have identified in post-exit CEOs, why feelings of worthlessness can persist for years even with significant wealth, and why a Dutch study found that personal well-being is a greater predictor of company success than the reverse. NATE'S JOURNEY Nate's path to business ownership started with a phone call from his mother. A privately held theatrical licensing company owned by about 16 different families had shares available. His mother owned some from her mother, and she told Nate he needed to buy in. By any professional investment standard, it made no sense. No dividends. An overpaid CEO. No reinvestment in the business. But he trusted his mother, the price was low, and he bought in. About eight years later, the existing CEO had to be fired, and Nate stepped into leadership. He had been working in private equity and investment banking on the capital markets side and held an MBA, but none of that fully prepared him for the CEO role. He describes himself as a CEO operator, not a CEO salesperson, someone who looked at the org chart upside down and focused on supporting the rest of the team rather than being the public face. Over eight to nine years, Nate transformed the company. He oversaw roughly a 97% attrition rate while rebuilding the team, switched to accrual-based GAAP accounting on his CFO's advice, and invested in a cloud-based tech stack that made the company fully remote in 2012, two weeks before Superstorm Sandy knocked out power in lower Manhattan. The company reduced licensing time from over four weeks to under four hours. When it came time to sell, the buyer, a music licensing company roughly ten times larger, adopted the entire tech stack for its own future growth. The company sold at what Nate describes as an incredibly high multiple. Then the real challenge began. THE LIMINAL PERIOD Nate references research by South African researchers who identified the "liminal period," the time between leaving one chapter and finding the next, marked by feelings of worthlessness, confusion, and depression. Nate experienced it for three to four years, with stretches where he would sleep only three or four hours a night, flooded with anxiety. He had significant money in the bank, was an expert in financial planning, and was still convinced he would be living out of the back of his car with his family in ten years. He talks about purpose, community, and identity as the elements that collapsed overnight. A business coach later helped him add a fourth dimension, health. Together, these capture what disappears when you sell. The purpose of supporting a team every day. The community of colleagues. The identity of being CEO. And the health foundation that gets undermined when income shifts from a regular paycheck to capital you don't know how to relate to. KEY INSIGHTS Exit readiness and operational excellence are the same pursuit. Nate didn't build cloud systems or switch to GAAP accounting to sell. He did it because he hated putting out fires. Every improvement that made the business better to run also made it dramatically more transferable and valuable. Purpose comes from relevance, not soul-searching. The advice to "go find a purpose" is too abstract. What works is finding where you are relevant to others, where your presence is improving someone's life. Personal well-being predicts company success. A Dutch study found that personal well-being was a greater predictor of company success than the reverse. Business owners who wait until after the exit to invest in their own health are leaving both fulfillment and business performance on the table. Wealth management has three legs, not one. Tax strategy and asset protection are as critical as investment management, especially for business owners whose wealth is concentrated in a single illiquid asset. Build community and purpose outside your business while you still have it. The people in your business will forget you existed the day after you sell. Relationships and meaning outside the company are how you avoid the worst of the liminal period. Perfect for business owners planning exits, entrepreneurs thinking about transferability, and founders who worry about what comes after the sale. FOR MORE ON THIS EPISODE https://www.coreykupfer.com/blog/natecollins FOR MORE ON NATE COLLINS LinkedIn: https://www.linkedin.com/in/nate-collins/ Company: https://www.raymondjames.com/founderwealthstrategies/events FOR MORE ON COREY KUPFER https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today! Episode Highlights with Timestamps [00:03:23] - Introduction and bio [00:07:05] - First deal, buying into a family-owned licensing company on his mother's recommendation [00:09:19] - Transforming the company with 97% attrition and building a dynamic team [00:14:03] - How theatrical licensing works, from school plays to international tours [00:18:52] - Switching to accrual-based GAAP accounting and the impact on buyer confidence [00:20:25] - Cloud systems, surviving Superstorm Sandy, and reducing licensing time from four weeks to four hours [00:25:30] - Written processes and procedures as a transferability driver [00:30:04] - Being a CEO operator versus a CEO salesperson [00:32:12] - The liminal period, post-exit depression, and the smallest violin problem [00:36:08] - Losing purpose, community, and identity overnight after the sale [00:41:04] - Finding purpose through relevance to others [00:45:51] - Dutch study linking personal well-being to company success Guest Bio Nate Collins is a former CEO who managed a successful exit of his international theatrical licensing company to a large PE-backed music licensing company in 2019. The company was a mid-market business with roughly 100 employees and mid-eight figures in revenue. Before becoming CEO, Nate worked in private equity and investment banking. He now works as a financial advisor and certified exit planning advisor at Raymond James, helping business owners, CEOs, and their families with tax mitigation, estate planning, financial planning, and preparation for life after exit. He runs a quarterly business exit planning workshop and is completing a workbook to guide business owners through the exit process. Host Bio Corey Kupfer is an expert strategist, negotiator, and dealmaker with more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker deeply passionate about deal-driven growth. He is the creator and host of the DealQuest Podcast. Show Description Do you want your business to grow faster? The DealQuest Podcast with Corey Kupfer reveals how successful entrepreneurs and business leaders use strategic deals to accelerate growth. From large mergers and acquisitions to capital raising, joint ventures, strategic alliances, real estate deals, and more, this show discusses the full spectrum of deal-driven growth strategies. Get the confidence to pursue deals that will help your company scale faster. Related Episodes Dave Hersh: The Psychology Behind Successful Exits (referenced in this episode for the "smallest violin" concept around post-exit struggles) Episode 366 - Jodi Hume: Founder Exits and the Emotional Journey Behind Major Business Decisions Episode 328 - Richard Manders: Post-Exit Transitions and Finding Purpose After Selling Your Company Episode 302 - Laurie Barkman: Preparing for a Successful Exit with Business Transition Insights Episode 330 - Pete Mohr: Building Enterprise Value and Exit Readiness Keywords/Tags post-exit depression, liminal period, exit planning, business transferability, CEO identity crisis, company valuation drivers, personal well-being business success, accrual-based accounting, exit readiness, licensing business model, sell your business preparation, post-sale anxiety, purpose after exit, mid-market exit, roll-up acquisition, business systems documentation, cloud-based operations, wealth management entrepreneurs, tax strategy business owners, certified exit planning advisor

From the Bronx to 17 years of boots-on-the-ground relationships across Latin America, Stephanie Pimentel shares the workforce governance, cultural alignment, and regulatory pitfalls that quietly cost U.S. companies millions in cross-border deals, and the proprietary audit system she built to catch them before capital is deployed. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with Stephanie Pimentel, founder and CEO of Lumena Global Advisory, a boutique firm specializing in Latin American market entry, cross-border workforce strategy, and expansion risk management. With an executive background in multinational operations and human capital leadership, she has advised U.S. companies, private equity groups, and growth-stage founders on structuring compliant, scalable operations across Mexico, Colombia, Brazil, and beyond. WHAT YOU'LL LEARN: Why treating Latin America as a single market is one of the most expensive assumptions a company can make. How workforce governance and cultural misalignment destroy deal value after close. Why standard due diligence falls short for cross-border transactions. How a single misclassified hire in Brazil can trigger a $250,000 government charge per employee. Why an employer of record is a testing tool, not a long-term strategy. And how to assess whether your leadership team is actually ready to execute across borders. STEPHANIE'S JOURNEY: Stephanie grew up in the Bronx and started her career as an HR coordinator at $11.75 an hour in New York. She moved into telecommunications, then logistics, where work with ports pulled her into cross-border trade. Over the next 17 years she built direct relationships across Latin America at every level, sitting down with CEOs and spending time with people running daily operations on the ground. That range of experience, combined with degrees in human resource management and forensic psychology, shaped a perspective most advisors in the space do not have. KEY INSIGHTS: Latin America is not one market. Legal structures for hiring differ dramatically between Mexico, Brazil, Chile, and Argentina, and applying a uniform approach creates compliance gaps before operations even begin. Culture is an operational variable. As Stephanie puts it, "Culture is how decisions get made when no one's watching." Cultural friction begins while the ink is still wet, drives up turnover, and burns capital before it shows on any spreadsheet. Brazil's hiring penalties are severe. A misclassified hire triggers government fees of $250,000 per employee, including mandatory benefits like a lunch stipend that do not exist in the U.S. framework. Standard due diligence is not enough. Latin America requires what Stephanie calls "due diligence on the due diligence." Domestic processes do not surface what matters in each specific country, and that gap closes only after the deal is signed. Expansion readiness has four components: financial strength, operating system robustness, compliance maturity, and leadership team readiness. Strong financials without a prepared leadership team are not enough. Smaller companies can and should expand internationally. Stabilize domestic revenue first, document your operating model, and expand in layers rather than leaps. Perfect for business owners considering Latin American expansion, operators managing post-acquisition integration across borders, and advisors working on international transactions. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/stephaniepimentel FOR MORE ON STEPHANIE PIMENTEL: Website: https://lumenaglobal.com LinkedIn: https://www.linkedin.com/company/lumena-global-advisory/ FOR MORE ON COREY KUPFER https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today! Episode Highlights with Timestamps: [00:02:28] - Introduction: Stephanie Pimentel's credentials and Lumena Global Advisory [00:09:04] - Case study: post-close, the operation is bleeding cash and the workforce is misaligned [00:10:59] - The five-pillar, 40-question proprietary audit system that grades expansion readiness [00:15:51] - Culture as an operational variable: why it burns capital before it shows on any spreadsheet [00:27:30] - Due diligence on the due diligence, vetting intermediaries, and building a compliant foundation [00:36:55] - The four components of expansion readiness and what makes a leadership team actually ready [00:44:14] - Freedom: earning the real seat at the table Guest Bio: Stephanie Pimentel is the founder and CEO of Lumena Global Advisory, advising U.S. companies, private equity groups, and growth-stage founders on compliant, scalable expansion across Latin America. A Dominican-American executive with degrees in human resource management and forensic psychology, she brings 17 years of on-the-ground relationships and compliance expertise to cross-border transactions across Mexico, Colombia, Brazil, and beyond. Related Episodes: Episode 324 - Sejal Lakhani-Bhatt: Cybersecurity and Technology Due Diligence in M&A: Learn how overlooked technical and compliance gaps can create major liability in transactions, and what buyers and sellers need to assess before close. Episode 350 - Tom Dillon: Business Valuation and the Realities of Exit Planning: Explore how operational health and structural preparation directly shape what a company is worth when it goes to market. Episode 329 - Cliff Nonnenmacher: Structuring Deals and Managing Complexity in Transactions: Understand how experienced deal practitioners approach structural challenges that arise when moving deals across complex environments. Keywords/Tags: Latin America expansion, cross-border deals, workforce governance, international M&A, expansion due diligence, market entry Latin America, cross-border workforce strategy, cultural alignment international business, employer of record, post-acquisition integration, compliance Latin America, deal due diligence international, Brazil hiring compliance, Mexico Colombia Brazil expansion, Latin America operational risk, expansion readiness, cross-border transactions, international deal strategy, workforce compliance, Lumena Global Advisory

Nearly 8 years, 400 episodes, and close to 30,000 monthly listens: Corey Kupfer shares how the DealQuest Podcast started as a solution to a real business problem, what the guest relationship strategy actually produces for a professional services firm, and why most podcasters quit before the compounding effect kicks in. In this milestone episode of the DealQuest Podcast, host Corey Kupfer hands the mic to his law firm partner Brian Meegan for a candid look inside nearly eight years of podcasting. Corey is an expert strategist, negotiator, and dealmaker with more than 35 years of professional deal-making experience, and the creator of the DealQuest Podcast. Brian Meegan is Corey's partner at Kupfer Law and a longtime member of Entrepreneurs' Organization, where the two originally met. WHAT YOU'LL LEARN: How a frustration with staying connected at scale led to a podcast now generating close to 30,000 listens per month, why the guest relationship is more valuable than the listener base for a professional services business, what "pod fade" is and why more than 85% of podcasts never reach 15 episodes, and the distinction between born dealmakers and situational dealmakers and why it matters for entrepreneurs who think deals aren't for them. ORIGIN STORY: The podcast started as a business problem. As the law firm grew, staying genuinely connected with clients, referral sources, and industry partners at scale became impossible. Authority marketing offered a path. An Entrepreneurs' Organization event in New York, where Gimlet Media founder Alex Bloomberg spoke candidly about starting a podcast company, made the medium click. The show launched in 2018 as Fueling Deals, rebranded to DealQuest about a year and a quarter in, and settled into the format it holds today: a defined open, a defined close, and everything in between is open conversation with no pre-prepared questions. KEY INSIGHTS: The three-part value model for a professional services podcast covers staying top of mind with your existing network, credibility and searchability when a prospect googles you, and actual search-driven client acquisition. All three have produced meaningful results for the DealQuest practice. The guest relationship is the most underestimated asset. Of approximately 300 guest interview episodes, the direct business and referrals from those guest relationships have outweighed what came from the broader listener base. The relationship starts from a place of value creation because the first thing Corey does is give guests access to a meaningful audience. Pod fade is real. More than 85% of podcasts don't reach 15 episodes. Corey's posture from the start was either commit to hundreds of episodes or don't start. Pick a medium you're genuinely energized by, because the energy in the conversation is not replicable with a format you find grinding. Born dealmakers and situational dealmakers are both real. People who treat dealmaking as an exclusive talent tend to opt out before they try. Deals can be learned, and there are structures where risk is easily managed. That's the premise behind Corey's talk called There's a Deal for That: any business challenge or opportunity has a potential deal solution worth at least considering. Perfect for entrepreneurs and business owners considering whether a podcast makes sense for their business, professionals thinking about authority marketing strategy, and dealmakers curious about what nearly 400 conversations about deals has taught someone with 35 years of deal-making experience. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/episode400 FOR MORE ON COREY KUPFER https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today! Episode Highlights with Timestamps [00:03:35] - The origin: Authority marketing, the scale problem, and why a podcast [00:06:45] - The Gimlet Media moment: How Alex Bloomberg's story made podcasting click [00:11:51] - Fueling Deals becomes DealQuest: The rebrand and format evolution [00:14:50] - Growth from 60-80 listens to close to 30,000 per month [00:18:26] - The lurker phenomenon: Why public engagement undercounts your real reach [00:20:28] - The three-part value model for a professional services podcast [00:23:06] - The guest strategy: Why guest relationships outperform listener reach [00:28:50] - Memorable guests and the deal stories that stuck [00:38:31] - Born dealmakers vs. situational dealmakers [00:44:05] - Final advice: Pick your medium, go deep, and commit for the long term Related Episodes Episode 327 - Solocast 71: Authority Marketing and How a Podcast Drives Deal-Driven Growth Episode 331 - Solocast 72: Deal-Driven Growth Strategy for Business Owners Episode 339 - Solocast 74: Equitizing Key Employees and Succession Planning Strategies Episode 351 - Solocast 77: Deal Structures and Strategic Growth Planning Keywords/Tags: DealQuest Podcast 400 episodes, authority marketing podcast, podcast for business development, deal-driven growth, professional services podcast strategy, B2B podcast strategy, staying top of mind at scale, guest relationship strategy, pod fade, Corey Kupfer, dealmaker mindset, born dealmakers situational dealmakers, business podcast milestone, there's a deal for that, Fueling Deals DealQuest rebrand, entrepreneur podcast strategy, M&A podcast, business growth through deals

From dot-com survivor to fractional CFO, Salvatore Tirabassi shares how his venture capital and private equity background enables him to deliver PE-grade financial strategy to founder-owned businesses, why the AI bubble looks fundamentally different from 2000, and how unit economics analysis should drive every growth-stage debt decision. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with Salvatore Tirabassi, a seasoned CFO who also brings a 15-year background as a partner in growth equity and venture capital funds. Sal is the founder of CFO Pro Analytics, where he delivers comprehensive financial strategy, modeling, analytics, and capital raising services to founder and family-owned businesses in the $3 million to $100 million revenue range. WHAT YOU'LL LEARN In this episode, you'll discover how the venture capital and private equity landscape evolved from a barbell structure into today's multi-tiered capital ecosystem, why the AI bubble debate is fundamentally different from the dot-com era based on where risk sits in the markets today, and the unit economics framework Sal uses before any client takes on debt to fuel growth. You'll also learn why most founder-owned businesses need practical capital like receivables financing and SBA loans rather than venture funding, and what the private credit market and AI-driven hiring shifts could mean for Main Street businesses. SAL'S JOURNEY Sal grew up playing basketball in competitive New York City high school leagues before moving through consulting and business school into venture capital in August of 1999. Seven months later, the dot-com bubble burst. While most investors fled, his fund doubled down on the companies they believed in. His first deal was a company called Gomez, a SaaS business before anyone used the term, with clients like Amazon paying subscription fees to measure customer web experience. Gomez ultimately sold for approximately $350 million around 2008. Sal continued doing growth equity deals in tech-enabled services before moving to the operating side as a CFO, merging his investor experience with operational expertise into a fractional CFO practice built specifically for founders and family-owned business owners. KEY INSIGHTS Having sat on the investor side as a partner in growth equity and VC funds, Sal builds his clients' financial infrastructure to the standard that institutional capital partners expect. His firm serves three segments on a nationwide basis. Long-term fractional CFO partnerships with founder-owned businesses priced on a fixed basis, investment banks prepping companies for sale on three-to-six-month engagements, and private equity funds needing to upgrade post-acquisition finance operations. On the AI bubble, Sal argues that in 2000, investment banks took small companies with no revenue public, giving individual investors venture capital-level risk exposure. Today that speculative risk sits in private markets. If a correction comes, it will likely show up in private assets rather than devastating public markets. Of the top 20 S&P 500 companies from 2000, only Microsoft remains in the top 20 today. Sal is also watching how AI will reshape hiring for knowledge-based organizations that need to balance automation with talent development, and whether the private credit market could create downstream pressure on Main Street businesses. Perfect for founders weighing different types of capital, business owners who know their financial infrastructure needs an upgrade, and anyone who wants a grounded AI bubble perspective from someone who survived the dot-com crash. Episode Highlights with Timestamps: [00:03:37] - Introduction and Sal's credentials [00:04:55] - Childhood basketball dreams in NYC [00:07:18] - Starting in VC in August 1999 and the dot-com crash [00:12:45] - Evolution of the VC and PE landscape over two decades [00:20:34] - From investor side to operator side as a CFO [00:26:28] - Practical forms of capital for founder-owned businesses [00:31:22] - Unit economics analysis and modeling the J-curve [00:36:16] - AI bubble versus dot-com bubble [00:42:06] - AI's impact on hiring and the private credit question [00:46:46] - Nine fundamental business models across every industry [00:52:00] - Freedom as time with family and opportunity for the next generation Related Episodes: Episode 350 with Tom Dillon explores fractional CFO work from a complementary angle, including when companies should avoid venture capital and what alternative funding sources might serve them better. Episode 326 with Herman Dolce covers raising capital in shifting markets and how technology cycles create winners and losers, connecting directly to Sal's observations about the private credit market. Episode 370 with Gerry Hays examines VC access and launching companies during the dot-com era, offering a founder's perspective that complements Sal's investor-side view. Guest Bio: Salvatore Tirabassi is the founder of CFO Pro Analytics, a fractional CFO firm serving founder and family-owned businesses in the $3 million to $100 million revenue range. He brings a 15-year background as a partner in growth equity and venture capital funds, with 20 years of expertise in strategic forecasting and capital management. His team operates primarily from the New York City area with remote capabilities nationwide. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/salvatoretirabassi FOR MORE ON SALVATORE TIRABASSI: Website: https://cfoproanalytics.com/ LinkedIn: https://www.linkedin.com/in/stirabassi/ FOR MORE ON COREY KUPFER: https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Keywords: fractional CFO, venture capital, private equity, dot-com bubble, AI bubble, capital raising, founder-owned business, growth equity, debt financing, unit economics, SBA loans, private credit, business models, exit planning

From printing a pitch deck in 8th grade to accidentally raising their first angel investment, building a 100,000-person wellness app with no salary for five years, and pivoting into a web design business that has launched over 100 sites, Leah and Becca Wiser share what it takes to build a business partnership that holds up under real pressure. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with Leah and Becca Wiser, twin sisters and co-founders of A Wiser Website, a concierge web design and brand strategy firm for service-based businesses. Having founded three companies together in the digital space, they bring a hard-earned perspective on co-founder dynamics, capital raising without a formal process, and knowing when a chapter has run its course. WHAT YOU'LL LEARN: In this episode, you will discover why the most effective first pitch is often a conversation, how twins with completely different working styles built a co-founder structure around those differences, and why defined boundaries between personal and professional time are operational infrastructure, not just personal preference. Leah and Becca explain the brownie split trap that quietly erodes partnerships, how five years of building a free app with no salary led to a stronger second business, and why asking for advice instead of money produced their first investment. LEAH AND BECCA'S JOURNEY: Leah and Becca Wiser grew up in South Florida surrounded by women who built businesses from scratch. Their mother, grandmother, and aunt Jennifer, who started a jewelry company in her child's playroom, all modeled entrepreneurship as a natural path. At 12, Leah and Becca were joining their aunt at trunk shows, watching hands-on client relationships drive sales. They have never held standard jobs. Their first real deal came in 8th grade, when they printed a full pitch deck to convince their parents they were responsible enough for cell phones. The idea came from watching TED Talks, which their parents required before any screen time. Watching others present and persuade translated, without them recognizing it yet, into a natural instinct to negotiate with preparation. THE CO-FOUNDER DEAL: Being identical twins did not insulate Leah and Becca from co-founder friction. About four years into their first major company, they questioned whether continuing made sense. Their solution was what they call business therapy, working with coaches who gave them language for their different working styles and a structure for honest communication. Leah tends toward detail, design, and execution. Becca handles client relationships, operations, and the outward-facing work. Once named and understood, those differences became their competitive advantage rather than their friction point. KEY INSIGHTS: The brownie split traps business partnerships. When co-founders begin tracking contributions the way children measure whether a brownie was cut perfectly in half, the focus shifts from outcomes to optics. Value comes in waves. A partnership built on flexibility and mutual trust outlasts one where each side keeps score. Asking for advice produces investment faster than asking for investment. When Leah, Becca, and their younger sister Hannah began developing Wumaze in 2017, they went to two people they knew for guidance on a rough early idea, not for funding. Those people saw their passion and invested. As Corey noted in this episode: when you ask for money, you get advice, and when you ask for advice, you get money. Defined containers for personal and professional time protect both. Leah and Becca live and work together in Washington, D.C. Without explicit structure around when it is business time and when it is sister time, both suffer. These are not personal accommodations. They are the structural boundaries that make the partnership sustainable. Pivoting is not failure when the evidence supports it. After five years building Wumaze with no salary and growing its community to over 100,000 users, Leah and Becca recognized it was time to move on. The skills they built during that period transferred directly into A Wiser Website. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/leahandbeccawiser FOR MORE ON LEAH AND BECCA WISER: Website: https://www.awiserwebsite.com/ Instagram: @AWiserWebsite FOR MORE ON COREY KUPFER https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today! Episode Highlights with Timestamps [00:11:17] - Introduction: Leah and Becca's background and the twin entrepreneur story [00:12:57] - First deal: The 8th-grade pitch deck for cell phones [00:19:20] - Why business partnerships are deals, and why they are not easy [00:23:08] - The brownie split analogy and the trap of tracking equal effort [00:30:19] - Wumaze: the mental health app started from college dorm rooms [00:41:34] - Five years, no salary, and the monetization challenge of a free app [00:45:40] - Recognizing when a chapter has completed its course [00:51:59] - Visionary and integrator: how their differences became their advantage [00:56:59] - What freedom means: Leah on giving freely, Becca on being present Guest Bio: Leah and Becca Wiser are identical twin sisters and creative partners who help service-based businesses take their brands and websites to the next level. With over 100 websites launched, they are strategic partners for companies looking to attract high-end clientele, generate quality leads, and turn their websites into powerful sales tools. They are also co-founders of Wumaze, a free emotional well-being app for women featured on Forbes, NBC, and CBS that grew to over 100,000 users. They operate A Wiser Website together. Host Bio: Corey Kupfer is an expert strategist, negotiator, and dealmaker with more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker deeply passionate about deal-driven growth. He is the creator and host of the DealQuest Podcast. Show Description: Do you want your business to grow faster? The DealQuest Podcast with Corey Kupfer reveals how successful entrepreneurs and business leaders use strategic deals to accelerate growth. From large mergers and acquisitions to capital raising, joint ventures, strategic alliances, real estate deals, and more, this show discusses the full spectrum of deal-driven growth strategies. Get the confidence to pursue deals that will help your company scale faster. Related Episodes: Episode 366 - Jodi Hume: Founder Exits and the Emotional Journey Behind Major Business Decisions: Explore the psychological dimensions of stepping away from a company you built and what founders need to prepare for beyond the transaction. Episode 350 - Tom Dillon: When NOT to Take Venture Capital Money: Discover alternative funding sources and how to evaluate whether outside capital is the right fit for your business model. Episode 330 - Pete Mohr: Building Enterprise Value and Exit Readiness: Learn the foundational steps for building a business positioned to grow and, when the time comes, exit on your own terms. Social Media Follow DealQuest Podcast: LinkedIn: https://www.linkedin.com/in/coreykupfer/ Website: https://www.coreykupfer.com/ Keywords/Tags: business partnership, co-founder dynamics, twin entrepreneurs, angel investment, capital raising, business pivot, web design strategy, service-based business, brand strategy, entrepreneurial journey, women entrepreneurs, co-founder relationship, visionary integrator, bootstrapping, mental health app, website as sales tool, entrepreneurship