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  • Episode 388: Navigate International Deals Successfully with Corey Kupfer

    Episode 388: Navigate International Deals Successfully with Corey Kupfer
    Jan 28 2026

    In this remastered DealQuest solocast, Corey Kupfer shares insights from over 35 years of cross-border deal-making experience. Originally recorded when the podcast was still called Fueling Deals, this episode remains highly relevant for entrepreneurs considering international expansion or partnerships with foreign companies.

    WHAT YOU'LL LEARN

    Why international deals offer significant growth opportunities in less saturated markets

    The critical importance of finding trusted local partners who understand culture, laws, and how business actually gets done in foreign jurisdictions

    How employment laws, IP protections, and disclosure requirements vary dramatically across countries and why this matters for your deals

    Cultural considerations that can make or break international transactions, including business card etiquette, relationship building timelines, and signing ceremony customs

    Why due diligence processes must be adapted for each jurisdiction's available information and verification methods

    How foreign companies entering your market could become partners, joint venture collaborators, or even buyers rather than competitors

    CROSS-REFERENCED EPISODES

    Episode 173 with Wendy Pease covers international deal lessons in depth

    Episode 337 with Jonathan Gardner discusses cultural integration in M&A transactions

    Episode 175 with Natasha Miller explores strategic partnerships with competitors

    ABOUT THIS EPISODE

    This remastered episode was selected from the DealQuest archives because the advice and frameworks remain timeless. Corey discusses why globalization will continue despite disruptions, how to approach market entry in foreign jurisdictions, and the opportunity to turn potential foreign competitors into strategic partners.

    CONNECT WITH COREY

    LinkedIn: linkedin.com/in/coreykupfer

    Website: coreykupfer.com

    ABOUT COREY KUPFER

    Corey Kupfer is an expert strategist, negotiator, and dealmaker with more than 35 years of professional deal-making and negotiating experience. He is a successful entrepreneur, attorney, consultant, author, and professional speaker who is deeply passionate about deal-driven growth. Corey is the creator and host of the DealQuest Podcast.
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    22 Min.
  • Episode 387: Mastering Debt Decisions and Alternative Investments with Stas Sukhinin

    Episode 387: Mastering Debt Decisions and Alternative Investments with Stas Sukhinin
    Jan 21 2026
    From investment banker to crypto fund strategist, Stas Sukhinin shares insider perspectives on how credit committees really make decisions, why over-leveraged companies fail fast during downturns, and where stablecoins are creating trillion-dollar transaction opportunities. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with Stas Sukhinin, a finance veteran with over 19 years of experience spanning investment banking, corporate lending, and alternative asset management. Stas began his career at internationally recognized institutions including UniCredit and Societe General, where he helped pioneer mezzanine loan products in Eastern Europe. By age 29, he had become a senior partner at one of the region's largest mezzanine lenders, managing a team of 20 finance professionals and overseeing a $450 million loan portfolio. WHAT YOU'LL LEARN: In this episode, you'll discover what really happens inside credit committees when your loan application gets reviewed and why factors unrelated to your business can determine outcomes. Stas explains how strong companies can go from healthy to restructuring in just three to four months when leverage catches up with them, and the critical difference between how first-time owners and experienced operators approach debt decisions. You'll learn the two key factors that determine how much debt your business can handle, why working capital provisions in purchase agreements deserve more attention than most buyers give them, and how sellers legally present financials in the most favorable light. The conversation also covers Stas's experience investing in the 2017 ICO boom where 90% of projects went to zero but winners returned 50x to 100x, why venture capital investors sometimes block deals that would be life-changing for founders, and where stablecoin transaction volume is already reaching trillions while most people remain unaware. STAS'S JOURNEY: Stas's path into finance started at age 14 when a classmate brought a business magazine to school. Reading about business owners selling companies for millions crystallized his direction. He knew he wanted to be in corporate lending where he could see businesses, analyze financials, and speak directly with owners while working with numbers at a bank. His first role as a junior credit analyst gave him exactly that. He progressed from working with small businesses that had no financials to mid-sized companies to large corporations. Each step taught him more about how deals really get done from inside the institutions making funding decisions. CREDIT COMMITTEE INSIGHTS: Stas pulls back the curtain on what actually happens when loan applications reach credit committees. The reality differs dramatically from what most business owners imagine. Factors affecting approval can seem completely unrelated to the specific deal. Maybe the bank already has a competitor in their portfolio. Maybe the receivable financing department has a different relationship with someone in your industry. One offhand comment from a committee member who hasn't read the full memo can change the entire trajectory of a conversation or result in higher interest rates. DEBT MANAGEMENT LESSONS: The pattern Stas has seen destroy companies in months follows predictable steps. Revenue drops or stagnates. Margins deteriorate because of increased competition and client uncertainty. Debt ratios that looked comfortable suddenly reach concerning levels. Refinancing options disappear just when needed most. Interest rates climb. Everything compounds simultaneously. The difference between experienced and first-time business owners comes down to scenario planning. Experienced operators build safety margins and stress-test assumptions. First-time owners assume conditions will continue as they are. That assumption determines survival. ALTERNATIVE INVESTMENTS: Stas joined a crypto investment fund at its inception in 2017 during the ICO boom. Out of many investments, approximately 90% went to zero. The winners returned 50x or 100x. His observation about liquidity cycles was particularly interesting. Traditional venture now averages seven-year holding periods while crypto projects can reach liquidity events in three or four years through token distributions. On stablecoins, Stas sees enormous opportunity in programmable money. Transaction volume is already in the trillions though most people in developed countries don't realize the scale. Goldman Sachs reportedly reduced bond settlement time from three days to minutes using blockchain technology. Perfect for business owners considering debt financing, entrepreneurs navigating capital raising, and anyone interested in how credit decisions really get made and where alternative investments are creating new opportunities. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/stassukhinin FOR MORE ON STAS SUKHININ: https://www.thesourcer.so https://www.linkedin.com/in/stassukhinin/ FOR MORE ON COREY KUPFER https://...
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    41 Min.
  • Episode 386: The $12 Million Lesson Hiding in Your Head with Adi Klevit

    Episode 386: The $12 Million Lesson Hiding in Your Head with Adi Klevit
    Jan 14 2026
    From process consultant to helping businesses increase their enterprise value through systematization, Adi Klevit shares proven strategies for documenting operations, preparing companies for successful exits, and ensuring post-merger integrations don't fall apart. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with Adi Klevit, founder of Business Success Consulting Group, who has spent over 30 years helping entrepreneurs bring order to their operations. Adi hosts the Systems Simplified podcast and contributes articles to Inc.com. WHAT YOU'LL LEARN: In this episode, you'll discover how documented processes dramatically increase enterprise value when selling a business, why buyers light up when they realize they're purchasing a system rather than just a company, and the concept of "unconscious competence" that keeps valuable knowledge trapped in entrepreneurs' heads. Adi shares how to extract hidden systems behind your natural talents, why entrepreneurs resist systematization even though it creates freedom, and how to get teams to actually follow documented processes. You'll also learn how process documentation complements entrepreneurial operating systems like EOS and Scaling Up, what breaks down in post-merger integration when documentation doesn't exist, and why AI is a powerful tool but cannot replace human judgment. ADI'S JOURNEY: Adi started a tutoring business in 9th grade that grew entirely through referrals, teaching her early lessons about balancing promotion with delivery. After working as VP of Marketing at an international consulting company, she launched her own firm when partnership wasn't available. As a general business consultant, she kept telling clients they needed documented processes, and nothing would happen. Finally, she offered to do it for them, and a niche was born. KEY INSIGHTS: A painting company owner documented all their processes with Adi's help. When he went to sell, the buyer's eyes lit up because he realized he wasn't just buying a painting company. He was buying a complete system and operation. On the flip side, Adi recently got a call from someone who bought a company with 60 employees and nothing documented. If everyone quit tomorrow, he would have no idea how to run what he just purchased. EOS implementers are Adi's biggest referral source because operating systems tell you that you need documented processes but don't create them for you. Adi's firm serves as a fractional process team that does the implementation work entrepreneurs keep pushing off. Too many people think deals are done when documents are signed. Adi works with companies that grow through acquisition, helping them bring new employees up to speed on unified systems. Even when both companies have good systems independently, those systems differ. Integration work determines whether the combined entity functions as one or remains two disconnected operations. For Adi, freedom means the ability to create. The systems she builds generate the freedom she values. Perfect for business owners preparing for exits, entrepreneurs struggling to extract knowledge from their heads, and acquirers concerned about post-merger integration. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/adiklevit FOR MORE ON ADI KLEVIT: https://www.bizsuccesscg.com https://www.linkedin.com/in/adiklevit/ https://www.successreplicator.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: Adi Klevit's journey from childhood entrepreneur to process consultant [09:13] - Starting a tutoring business in 9th grade and learning about business cycles [15:22] - How passion for systematization developed through frustration with clients [18:31] - The painting company story: Buyers purchasing systems, not just businesses [22:04] - Corey's business development system he didn't know he had [26:37] - Getting teams to actually follow documented processes [34:05] - How process documentation complements EOS and other operating systems [38:56] - Post-merger integration: Where good deals go to die [46:26] - Which business areas prove most problematic in integration [51:03] - Why AI cannot replace human judgment in process work [52:...
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    42 Min.
  • Episode 385: 2026 Deal Outlook and Market Trends with Brian Meegan

    Episode 385: 2026 Deal Outlook and Market Trends with Brian Meegan
    Jan 7 2026
    From a lumpy 2025 market to building pent-up demand, M&A attorneys Corey Kupfer and Brian Meegan share their frontline perspective on deal trends and what business owners need to know heading into 2026. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with his partner Brian Meegan of Kupfer. to kick off the new year with a candid conversation about the deal market. Together, they've handled dozens of deals totaling hundreds of millions of dollars in purchase price and enterprise value across wealth management, tech, and trade industries nationwide. WHAT YOU'LL LEARN: In this episode, you'll discover why the 2025 M&A market has been "lumpy" with strong activity in certain sectors while others slowed, and how markets normalize uncertainty when clarity takes too long. Corey and Brian discuss tax legislation certainty versus tariff uncertainty pending Supreme Court review, why pent-up demand builds pressure that eventually releases, and how massive PE dry powder creates deployment urgency. You'll learn why equitizing Generation 2 leadership years before an exit improves options and valuation, how trade industries remain attractive due to AI resistance, and what regional differences mean for deal opportunities. DEAL MARKET REALITY: The end of 2024 was intense, and momentum carried into 2025. Yet conversations with colleagues revealed uneven activity nationwide. Wealth management stayed robust while other sectors slowed. Weaker earnings combined with elevated prices created buyer-seller disconnects. CERTAINTY AND UNCERTAINTY: Markets crave predictability. Recent tax legislation provided clarity around R&D credits and SALT deductions. Tariff policy remains uncertain with potential Supreme Court review, creating productivity costs as companies refigure supply chains. PENT-UP DEMAND: When natural deal flow gets suppressed, it builds pressure rather than disappearing. PE firms sit on enormous capital with fund timeline pressures. Money isn't the constraint. Finding opportunities and having clarity to proceed are the real bottlenecks. THE GEN 2 IMPERATIVE: Equitizing key executives years before a potential exit creates tax-efficient structures, makes companies more attractive to buyers, and gives acquirers confidence. Waiting until deal time limits options and hurts valuation. REGIONAL DIFFERENCES: Brian's Denver practice serves different markets than Corey's coastal work. Colorado features strong tech sectors and alternative energy with California migration. Heavy manufacturing concentrates in Arizona and Nevada. TRADE CONSOLIDATION: Professionalization of trades including plumbing, electrical, and HVAC continues after more than a decade. These industries resist AI disruption, making them attractive for stable revenue and consistent fundamentals. Perfect for business owners considering exits, entrepreneurs evaluating opportunities, and anyone wanting frontline perspective on current M&A conditions. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/brianmeegan2026 FOR MORE ON BRIAN MEEGAN: https://www.kupferlaw.com/ https://www.linkedin.com/in/brian-meegan/ 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: Kicking off 2026 with partner Brian Meegan [02:00] - Why the M&A market has been "lumpy" across sectors [04:00] - Tax policy certainty after major legislation passed [08:00] - 2026 outlook and pent-up demand building pressure [13:00] - Appreciation for DealQuest listeners and clients [16:00] - The importance of equitizing Generation 2 leadership [18:00] - Tax efficiency and planning equity participation early [22:00] - Heavy manufacturing trends in Arizona and Nevada[28:00] - Optimism for 2026 and where opportunities exist Guest Bio:Brian Meegan is a partner at Kupfer., bringing extensive transactional experience from his Denver-based practice. Brian specializes in M&A transactions and complex deal structures across tech, natural resources, and professional services. His Colorado practice provides unique perspective on regional market dynamics outside traditional coastal centers. Host Bio:Corey Kupfer is an expert strategist, negotiator, and dealmaker with more than 35 years of professional ...
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    33 Min.
  • Episode 384: Happy Holidays DealQuest Family

    Episode 384: Happy Holidays DealQuest Family
    Dec 31 2025
    About fifteen years ago, I gave up the conversation around balance entirely. The word I use instead is integration, and in this holiday episode I share why that shift transforms how entrepreneurs experience everything from year-end deal closings to family obligations. In this holiday episode of the DealQuest Podcast, I share reflections on 2025, point to must-listen episodes, preview what's coming in 2026, and break down the integration mindset that has shaped my approach to business and life. WHAT YOU'LL LEARN: In this episode, you'll discover why the balance conversation creates unnecessary stress, the four episodes from 2025 worth revisiting, what's coming in January with my partner Brian Meegan, how designing where you live and which clients you take on become integration decisions, why great mergers have integration at their core while failed ones have integration problems, and how clarity creates filters for better decisions. MY INTEGRATION JOURNEY: Balance frames everything as separate competing demands pulling in different directions. Integration creates a lens where choices support multiple priorities simultaneously. Living in Marina del Rey serves integration. Fifteen minutes from LAX. Secure building. Walking my dog along the promenade during breaks. Cold brew moments on the patio before M&A negotiations. Every choice reduces friction. EPISODES WORTH REVISITING: Dave Hersh on Episode 381 delivered one of my favorite interviews ever, sharing hard truths about post-exit challenges through his inner board meeting framework. Bob Bush on Episode 377 told his remarkable journey from East St. Louis to founding Mutombo Coffee with the late Dikembe Mutombo. Jodi Hume on Episode 366 helps founders avoid the regrets that plague up to 85% of entrepreneurs after exits. Hikari Senju on Episode 354 offered a different lens on building AI companies through strategic bootstrapping. WHAT'S COMING IN 2026: January kicks off with my partner Brian Meegan joining to discuss what we're seeing in the deal landscape. Special series are planned diving deep into specific industries similar to our RIA aggregator coverage. KEY INSIGHTS: The great mergers and acquisitions have integration at their core. The ones that fail typically have integration problems. Choosing podcasting over a weekly column reflects integration thinking. This format feels like an extension of who I am rather than an obligation. When you have clarity about what integrates in your life, it creates a filter for decisions, just like whiteboarding sessions create filters for M&A clients. Perfect for entrepreneurs feeling pulled in too many directions, business owners heading into year-end closings, and dealmakers who want to understand how integration principles apply to M&A success. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/holiday2025 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: Holiday wishes to the DealQuest community [02:00] - Episode recommendations: Four must-listen conversations from 2025 [04:00] - Dave Hersh Episode 381: Psychology behind successful exits "[05:00] - Bob Bush Episode 377: Global dealmaking and Mutombo Coffee [06:00] - Jodi Hume Episode 366: Avoiding post-exit regret [06:30] - Hikari Senju Episode 354: Strategic bootstrapping for AI companies [07:00] - What's coming in 2026 with Brian Meegan [09:00] - The integration versus balance conversation [11:00] - Designing life for integration: Marina del Rey example [14:00] - Integration in deals: Why great M&A has integration at its core [15:00] - Clarity as a filter for decisions [15:30] - Closing thoughts and gratitude Host Bio:Corey Kupfer is an expert strategist, negotiator, and dealmaker with more than 35 years of professional deal-making and negotiating experience. He is the creator and host of the DealQuest Podcast and managing partner of Kupfer PLLC. Show Description: Do you want your business to grow faster? The DealQuest Podcast reveals how successful entrepreneurs use strategic deals to accelerate growth. From mergers and acquisitions to capital raising, joint ventures, and strategic alliances, this show covers the full spectrum of deal-driven growth strategies. ...
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    17 Min.
  • Episode 383: Sell Your Business for a Premium with Channing Hamlet

    Episode 383: Sell Your Business for a Premium with Channing Hamlet
    Dec 24 2025
    From closing dinner conversations that changed his career trajectory to advising on transactions up to half a billion dollars, Channing Hamlet shares proven strategies for selling businesses at premium valuations through proper preparation, understanding sector-specific value drivers, and creative deal structures. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with Channing Hamlet, Managing Director at Objective Investment Banking and Valuation, who has over 30 years of experience advising business owners on management issues, transaction execution, and business valuation. Channing's firm specializes in lower middle market transactions, typically ranging from $10-25 million up to $100-150 million in value. WHAT YOU'LL LEARN: In this episode, you'll discover how buyer expectations have dramatically shifted over 25 years and why preparation requirements for premium valuations have intensified. Channing explains why clean accounting is no longer optional, how financial projections can make or break your valuation, and the three key value drivers beyond revenue and EBITDA. You'll also learn creative deal structures that can save transactions when traditional financing becomes challenging. CHANNING'S JOURNEY: Channing's path into dealmaking started at the family dinner table, where his father frequently hosted business visitors for dinner conversations about deals and transactions. His pivotal moment came while working at Legg Mason doing M&A, when a patriarch from a third-generation family business pulled him aside at a closing dinner and shared how much the work had changed his family's life. That moment hooked him on helping entrepreneurs and family businesses navigate successful exits. KEY INSIGHTS: In the mid-1990s, private equity firms paid four to six times EBITDA. Today, good companies sell for 10 to 14 times EBITDA, but buyers expect sellers to show up polished and prepared. Channing identifies three major value drivers beyond EBITDA. First, understanding what drives value in your specific sector. Second, building predictability through recurring revenue and systematized operations. Third, clearly articulating your differentiation and unique value proposition. Financial projections matter because selling takes approximately nine months, meaning buyers pay based on projected results, not historical performance. A last-minute budget won't stand up to scrutiny. Channing also shares a creative deal structure where seller financing at 10% interest saved a transaction when traditional bank financing fell through. Perfect for business owners considering an exit in the next 3-5 years, M&A advisors working with lower middle market companies, and anyone wanting to understand what truly drives premium valuations. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/channinghamlet FOR MORE ON CHANNING HAMLET: https://objectivecp.com https://www.linkedin.com/in/channing-hamlet/ 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: Channing Hamlet's journey from family dinner table conversations to investment banking [02:17] - Growing up around business deal discussions and choosing the outdoor life [03:45] - The closing dinner moment that changed everything at Legg Mason [08:19] - How the M&A landscape has transformed over 25 years [10:26] - Why buyer expectations and preparation requirements have increased [18:52] - Understanding sector-specific value drivers through the printing industry example [23:39] - Market outlook for 2023 and beyond [31:43] - The three legs of Objective's valuation practice[40:03] - Finding Objective Capital Partners and getting in touch Guest Bio Channing Hamlet is a Managing Director at Objective Investment Banking and Valuation, focused on leading the firm's valuation advisory service practice and transaction execution for its investment banking services practice. He is a results-driven executive with 30+ years of experience advising owners on management issues, transaction execution, and business valuation. Channing draws on a diverse background that includes direct management experience, strategy consulting, private equity investing, investment banking, and business ...
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    44 Min.
  • Episode 382: Building Enterprise Value Through Fee-Based Transitions with David Lau

    Episode 382: Building Enterprise Value Through Fee-Based Transitions with David Lau
    Dec 17 2025
    From chief marketing officer at the first internet bank to building the leading annuity platform for RIAs, David Lau shares proven strategies for raising capital, navigating public company challenges, and why converting commission-based revenue to fee-based can multiply your exit value by five times. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with David Lau, founder and CEO of DPL Financial Partners, who has raised over $500 million across multiple ventures and built DPL into a platform serving more than 10,000 advisors at over 3,500 RIA firms. WHAT YOU'LL LEARN: In this episode, you'll discover why organic growth matters far more than market growth when acquirers evaluate your business, how converting commission-based annuity business to fee-based can multiply both your revenue and your exit multiple, the real tradeoffs of taking institutional capital and signing up for aggressive growth, the critical difference between venture capitalist optimism and private equity scrutiny, and how recognizing when your business has "run its course" can open the door to building something bigger. DAVID'S JOURNEY: David's career began as chief marketing officer of Telebank, the first internet bank, where he helped raise over $500 million. When preparing to go public, the stock jumped from $17 to $150 in weeks before Goldman Sachs stabilized pricing at $105. He later built Jefferson National, an insurance carrier he sold to Nationwide. That experience taught him the valuable part was distribution, not the capital-intensive balance sheet, leading directly to founding DPL in 2018. KEY INSIGHTS: A billionaire David met admitted he "mistook a bull market for brilliance." Acquirers only pay premium multiples for organic growth. If you did nothing different over the last decade as an RIA, you're making twice as much just from market performance. Buyers know this. Converting from commission to fee-based transforms exit potential with three times the revenue and five times the multiple, while expanding your buyer pool. DPL's technology reviews 2,500 policies per hour, and a significant portion of DPL's $4 billion in annuity sales were M&A related. When launching DPL, David planned to bootstrap until meeting Todd Boehly. Taking institutional capital means signing up for aggressive growth where some team members won't make it to the next stage. Venture capitalists are optimists who see your vision. Private equity investors see everything that can go wrong. Perfect for RIA owners considering M&A, hybrid advisors evaluating fee-based transitions, and entrepreneurs weighing capital raising decisions. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/davidlau FOR MORE ON DAVID LAU: https://www.dplfp.com https://www.linkedin.com/in/david-lau-b6449b7/ https://x.com/dpl_fp 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: David Lau's journey to building DPL Financial Partners [04:00] - Capital raising at Telebank: $500 million raised, stock jumping from $17 to $150 [08:00] - The tradeoffs of taking institutional capital and signing up for aggressive growth [12:00] - Venture capitalists as optimists versus private equity investors who see downside [16:00] - Why choosing the right capital partners matters more than just getting funded [20:00] - How DPL solved the RIA insurance problem with commission-free products [24:00] - Converting to fee-based: Three times the revenue and five times the multiple [28:00] - Why organic growth matters more than market growth in valuations [33:00] - The future of RIA consolidation and when to sell a business [40:00] - Freedom: Working with Russian defectors and gaining perspective Guest Bio David Lau is founder and CEO of DPL Financial Partners, the leading annuity platform for RIAs. Since 2018, DPL has worked with 20 insurance carriers and built an advisor base of more than 10,000 advisors from over 3,500 RIA firms. Before founding DPL, David was COO of Jefferson National, which he helped build and sell to Nationwide. Earlier, he served as chief marketing officer at Telebank, the first internet bank, where he helped raise over $500 million. His work has been covered in The Wall ...
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    42 Min.
  • Episode 381: The Psychology Behind Successful Exits with Dave Hersh

    Episode 381: The Psychology Behind Successful Exits with Dave Hersh
    Dec 10 2025
    What if losing your life savings on your first investment at age 27 became the catalyst for understanding why 90% of startups get stuck for the same psychological reasons? That's exactly what happened to Dave Hersh, founding CEO of Jive, board partner at Andreessen Horowitz, and author of Reignition. Dave grew Jive from an open-source project to a NASDAQ IPO, bootstrapping to $12 million over five years before raising venture capital. But when he watched Atlassian, a comparison company that started at the same time, stay on their original trajectory and become worth over $20 billion while Jive eventually died on the public markets, he realized fear and insecurity had driven his capital decision rather than genuine strategy. That painful lesson shaped everything Dave now teaches as an executive coach and General Partner at Metamorph Partners. After working with hundreds of stuck companies, he discovered that 90% of failures trace back to the same psychological patterns. Not cash. Not product market fit. Not competition. Subconscious patterns driving decisions without founders knowing. The statistics are sobering. Between 80 to 95% of founders suffer mental health issues while running their companies. Even successful founders have an 85% chance of experiencing depression or struggles for up to 10 years post-exit. Only 15% are truly thriving after they sell. Dave introduces his inner board meeting framework, which helps founders identify the internal parts driving major decisions. The child wanting safety. The hero wanting to save everyone. The warrior that cannot let go. When you understand these patterns, you can work toward compromises that break through stalemates. The conversation covers when and why to raise capital versus bootstrap, the transition process between identities that most founders skip, and the human-first competitive moats that will define success in the AI era. For founders navigating capital decisions, stuck companies, or the complex terrain after exit, this episode offers a different lens on what actually determines outcomes. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/davehersh FOR MORE ON DAVE HERSH:https://www.linkedin.com/in/davehersh/https://one-in-ten-thousand.beehiiv.com/ FOR MORE ON COREY KUPFERhttps://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: Dave Hersh's journey from dot-com era to executive coaching [02:30] - Growing up in Newport, Rhode Island with no entrepreneurial modeling [05:15] - First entrepreneurial experience: selling ninja weapons to neighborhood kids [07:45] - Arriving in New York on September 10th, 2001 and founding Jive [12:00] - Bootstrapping to $12 million over five years without outside capital [16:30] - The Facebook moment and decision to raise venture capital in 2006 [21:00] - Why founders equate raising money with success and the 10% reality [25:45] - The Atlassian comparison and what could have been a $20 billion outcome [30:15] - Mental health statistics: 80-95% of founders suffer while running companies [34:00] - Post-exit malaise: 85% of successful founders struggle for up to 10 years [43:00] - Identifying internal parts: the child, hero, warrior, and insecure parts [51:30] - Human-first moats in the AI era Guest Bio Dave Hersh is an executive coach, speaker, and investor based in San Francisco with over 30 years of experience in strategy, startups, and conscious leadership. He was the founding CEO of Jive, which he grew from an open-source project to a NASDAQ IPO. He also spent two years as a Board Partner (investor) at the venture capital firm Andreessen Horowitz. He is the author of Reignition, a playbook for helping startups get unstuck and find their breakthrough, and is working on a new book about enlightened leadership in the era of AI. Dave currently serves as General Partner at Metamorph Partners. 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 ...
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    43 Min.