DealQuest Podcast with Corey Kupfer Podcast Por Corey Kupfer arte de portada

DealQuest Podcast with Corey Kupfer

DealQuest Podcast with Corey Kupfer

De: 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!© 2026 014078 Economía Gestión y Liderazgo Liderazgo Política y Gobierno
Episodios
  • Episode 396: Do You Actually Want to Be a Deal Maker with Corey Kupfer

    Episode 396: Do You Actually Want to Be a Deal Maker with Corey Kupfer
    Mar 25 2026
    From year-end deal crunches to honest conversations about risk tolerance and self-knowledge, Corey Kupfer makes the candid case for why deal making may not be for every entrepreneur, and what it actually takes if you decide it is. In this remastered DealQuest solocast, host Corey Kupfer draws from his own experience managing multiple year-end closings while stretched thin to walk through three reasons why deals may not align with every business leader's goals or temperament, and how the flip side of each reason reveals the roadmap for those who do want to pursue deals. WHAT YOU'LL LEARN In this episode, you'll discover why even experienced deal teams face periods of all-encompassing intensity, how risk tolerance shapes whether and how you pursue deals, and why some entrepreneurs are better served by doubling down on organic growth. Corey explains how the CPR tool from his Authentic Negotiating book can help you assess whether deals belong in your growth strategy, and why the distinction between born deal makers and situational deal makers matters. THE HONEST CASE FOR SELF-ASSESSMENT Corey acknowledges the counterintuitive nature of a deal-making advocate telling listeners they might not want to be deal makers. But the premise is grounded in something he returns to throughout his work. Self-knowledge matters more than ambition. The decision to pursue deal-driven growth should come from clarity about what you want, not from external pressure or assumptions. He connects this to the CPR tool from his Authentic Negotiating book, which stands for Context, Purpose, and Results. The CPR framework applies as powerfully to the question of whether deals should be part of your growth strategy as it does to any specific negotiation. Corey also previews his dealmaker retreats, which will begin with visioning work before any deal strategy is discussed. KEY INSIGHTS Deal work is periodically all-encompassing. Corey shares his experience managing multiple year-end closings while sick, with his team stretched. He walks through disclosure schedules in asset purchase deals, where sellers must provide representations and warranties covering contracts, employees, regulatory matters, and taxes. Getting these wrong risks breach and potential indemnity obligations. Risk tolerance is a prerequisite. Every successful deal maker has deals that fail or underperform. Corey shares a live example of risk-averse buyers requesting protections that could burden his client. If deals going wrong would affect your sleep or health, the personal cost may outweigh the benefit. Your highest and best use may not include deal making. Some entrepreneurs generate exceptional results through organic growth. Adding deals could dilute their greatest strength. Corey compares growth diversification to a diversified stock portfolio but notes you can hire the right team to handle deals while you focus on your strengths. Being a deal maker is not binary. There are situational deal makers who evolve into the role because the timing aligns, an opportunity appears, or their mindset shifts. The question is whether this is the right time for you. Perfect for entrepreneurs weighing whether deal-driven growth aligns with their goals, business owners considering M&A or partnerships, and anyone interested in an honest self-assessment framework before committing to a deal strategy. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/beadealmarker FOR MORE ON COREY KUPFER:LinkedIn: https://www.linkedin.com/in/coreykupfer/ Website: https://www.coreykupfer.com/ Episode Highlights with Timestamps:[00:02:12] - Solocast opens with the counterintuitive premise of why you should not be a deal maker [00:04:53] - Why deal work can be all-encompassing and the demands of year-end closings[00:06:32] - Disclosure schedules in asset purchase deals and why they matter [00:10:25] - The reality of pushing through fatigue and intensity [00:11:57] - The inherent risk of deal making and why some deals will always fail [00:14:01] - Live deal example with risk-averse buyers requesting protections and guarantees[00:14:54] - Organic growth as an alternative path and when deals become a distraction [00:15:53] - Superpower and highest and best use [00:18:25] - Self-knowledge as the foundation and the CPR tool from Authentic Negotiating[00:19:00] - Dealmaker retreats and why they start with visioning [00:21:02] - What it takes to be a deal maker and the concept of situational deal makers 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 ...
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    24 m
  • Episode 395: Building Exit-Ready Businesses with Marty Fahncke

    Episode 395: Building Exit-Ready Businesses with Marty Fahncke
    Mar 18 2026
    From grassroots soccer parks to $600 million exits, Marty M. Fahncke reveals why every dollar of EBITDA sacrificed for tax savings costs you seven on a multiple, how the build versus buy decision needs a reality check, and why a business fully prepared to sell is the best business to own. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with Marty M. Fahncke, CMAA, who has helped hundreds of businesses scale to over $1 billion in combined revenue and executed nearly $500 million in M&A deals. He is the founder of Westbound Road, an M&A advisory firm specializing in digital businesses in the $5-50 million range, and author of Boomer Sells the Business: A Step-by-Step Guide to Cashing Out and Living Large. WHAT YOU'LL LEARN: In this episode, you'll discover why the build versus buy analysis fails when founders underestimate timelines and costs, and why opportunity cost is often the biggest expense that never appears in spreadsheets. Marty explains how combining marketing expertise with M&A strategy creates advantages most advisors lack, the costly trade-off between profit maximization and tax mitigation that saves twenty cents but costs seven dollars on a multiple, and why operational decisions like CRM selection or staffing structure can kill deals worth millions. You'll also learn how the Who Not How philosophy transforms into a powerful acquisition playbook, why SaaS founders who turned down $50 million in 2021 are accepting those valuations were an anomaly, and how authority marketing through podcasts generates clients who arrive ready to sign without sales conversations. MARTY'S JOURNEY: Marty grew up in the mountains of Utah wanting to be either a forest ranger or join the military. Neither path worked out, and he ended up on the entrepreneur path instead. Even as a teenager, he showed entrepreneurial instincts, selling water purifiers and vacuums and running a bicycle rehab business at age twelve. M&A was completely off his radar until he and some friends started a soccer training product company. They took a truly grassroots approach, setting up canopies at local parks every weekend where kids played soccer. Marty had his children demonstrate the product while he sold to parents. Those park sessions taught them exactly what messaging resonated. Marty used those insights to create a marketing campaign that got the product onto QVC in the United States and Japan. Just eighteen months in, they received an unsolicited $1.5 million offer from a private equity firm buying their proven QVC sales channel. His next deal flipped the approach. Instead of building from scratch, Marty and a partner combined two competing businesses, each doing $1.5-2 million in revenue. By eliminating competition and consolidating operations, they scaled from under $4 million to $30 million in two years. That company eventually became part of a $600 million exit through a reverse merger. After that exit, Marty built a personal portfolio of businesses. In 2019, he focused on M&A full-time. When 2020 hit, he saw opportunity in the chaos. He reached out to companies about selling, and economic uncertainty generated many yes responses. When businesses weren't right for his portfolio, sellers asked if he knew other buyers. He started triangulating deals, brought in partner Becky, and launched Westbound Road in 2020. They focus exclusively on digital businesses between $5 and $50 million, including e-commerce, SaaS, publishing, marketing agencies, and virtual professional services. The firm is intentionally small at five people but highly specialized. THE MARKETER'S EDGE: Marty brings a rare combination of world-class marketing expertise and deep M&A experience. Most advisors excel at one or the other, rarely both. He is a marketer at heart and applies marketing principles to M&A strategy. This matters because organic growth drives valuation multiples. Buyers pay premiums for demonstrated growth momentum, often adding an extra turn or two on exit multiples. Marty sees both sides of the equation, knowing how to build marketing systems that drive organic growth and how to structure deals that accelerate inorganic expansion. KEY INSIGHTS: The build versus buy decision requires brutal honesty. Marty sees unreasonable optimism every time founders analyze whether to build or acquire. His rule: double the timeline, triple the costs. Even then, most analyses miss opportunity cost. What revenue will you lose spending years building? What market share will competitors capture while you're distracted? These costs rarely appear in spreadsheets but are often the most expensive part of the build decision. The Who Not How philosophy becomes an acquisition playbook. When something needs to be done, don't ask how you can learn it yourself. Find someone already better at it and acquire them. Marty applied this when a bookkeeping firm asked for growth help. Instead of consulting fees, he negotiated equity, brought marketing ...
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    44 m
  • Episode 394: Navigating Multiple Exits Across Tech's Evolution with Raj Singh

    Episode 394: Navigating Multiple Exits Across Tech's Evolution with Raj Singh
    Mar 11 2026
    From installing network cards as a teenager to navigating four successful exits across decades of tech evolution, Raj Singh shares lessons on acquisition timing, building buyer relationships, and the emotional journey founders experience after selling. Raj Singh is VP of Product at Mozilla, leading new zero-to-one product initiatives. He joined Mozilla in 2022 via acquisition of his startup Pulse (AI meeting summarization). Previously, he co-founded Tempo AI (acquired by Salesforce 2015), All the Cooks (acquired by CookPad), and served as VP of Business Development at Skyfire (acquired by Opera). WHAT YOU'LL LEARN You'll discover why exit windows matter more than plans, how to build relationships with potential acquirers years in advance, the four emotional stages after selling, why 80-85% of acquisitions are CEO-driven, and how founder fatigue is the number two reason startups fail. RAJ'S JOURNEY Raj's entrepreneurial instincts showed up early. Before college, he installed network cards in friends' computers for students heading to dorms. Desktop computers didn't have Ethernet ports back then, so he bought cards from Fry's Electronics, installed them, set up drivers, and charged for the service. His first substantive deal came during the dot-com crash, a net-zero acquisition in the early video codec era around 2000. He's since navigated four exits across radically different market conditions: the dot-com crash, 2008 financial crisis, COVID, and today's landscape. Each taught him something different about timing, negotiation, and integration. "What worked yesterday doesn't work today." THE SERIAL EXIT OPERATOR Raj's perspective comes from exiting companies during each major market cycle, giving him pattern recognition most founders never develop. At Mozilla, he's thrived leading products like Mozilla Solo (AI website builder) and Postful (social media management), finding ways to keep learning within a larger organization. KEY INSIGHTS Exit windows exist and close. Miss one, and the next might not emerge for 3-8 years. Founder fatigue is the number two reason startups fail. The hardest question: can you push through for another five years? Build acquisition relationships years in advance. Identify your 10 most likely buyers on day one. Check in every six months with no intent to sell. Acquisitions are about timing. If your timing doesn't align with a buyer's executive off-site decision, you could be off by six months and it won't happen. The emotional journey: relief when the deal closes, regret within days, inspired to make it the best acquisition ever, then acceptance it's not your company anymore. FOR MORE ON THIS EPISODE https://www.coreykupfer.com/blog/rajsingh FOR MORE ON RAJ SINGH LinkedIn: https://www.linkedin.com/in/rajansingh/ Email: raj@rajansingh.com Twitter/X: @rajansingh Threads: @rajansingh 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:[00:06:37] - Introduction: Raj Singh's bio and background [00:08:28] - Childhood computer interest and early entrepreneurial instincts [00:08:54] - First side hustle: Installing network cards for college students [00:12:07] - First substantive deal during dot-com crash [00:13:30] - Evolution of startup ecosystem: from Chamber of Commerce books to today [00:21:24] - Journey to Mozilla via Pulse acquisition [00:24:03] - Why staying at Mozilla works: continuous learning and challenge [00:32:10] - All the Cooks exit during Y Combinator three-day decision window [00:35:53] - Tempo AI monetization struggles and Salesforce acquisition [00:39:23] - Four emotional stages after acquisition: relief, regret, inspired, acceptance [00:43:07] - Exit windows and why timing matters more than plans [00:43:32] - Founder fatigue as number two reason startups fail [00:48:19] - Building relationships with 10 potential acquirers from day one [00:50:42] - When incumbents enter your category (market acceleration) [00:51:05] - Enterprise multiple winners versus consumer winner-take-all [00:51:31] - Current work at Mozilla: Solo and Postful products [00:52:53] - What freedom means: choosing where to spend time Guest Bio: Raj Singh is VP of Product at Mozilla, leading zero-to-one product initiatives. He joined via ...
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    44 m
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