DealQuest Podcast with Corey Kupfer Podcast By Corey Kupfer cover art

DealQuest Podcast with Corey Kupfer

DealQuest Podcast with Corey Kupfer

By: Corey Kupfer
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Why do some companies grow by leaps and bounds while others only inch forward? Simple. They embrace Deal-Driven Growth in addition to organic growth! DealQuest is where you learn how to strategize, prepare for, find, and complete deals to grow your company faster. Listen in as host Corey Kupfer takes you behind the scenes with some of the world’s most fascinating deal-savvy business leaders. This is the one place where they can share openly the secret to deals they have done (or failed to do) and the issues, opportunities, benefits, pitfalls and lessons learned. Here you learn first-hand all about: Powerful deals that require little capital, mergers, acquisitions, and tuck-ins, Joint ventures, partnerships, and strategic alliances, licensing, raising capital and onboarding key employees, negotiating, structuring, finding, valuing, closing and integrating deals. Don’t be the one at the table who doesn’t grasp the power of Deal-Driven Growth!© 2025 014078 Economics Leadership Management & Leadership Politics & Government
Episodes
  • 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 mins
  • 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 mins
  • 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 mins
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