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 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
  • Episode 393: From Failed Investments to 70+ Startups with Andrew Ackerman

    Episode 393: From Failed Investments to 70+ Startups with Andrew Ackerman
    Mar 4 2026
    From losing his entire $25,000 life savings on his first investment to backing over 70 startups, Andrew Ackerman shares proven strategies for evaluating founders, testing assumptions cheaply, and why the best entrepreneurs see deals where others see nothing. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with Andrew Ackerman, a serial entrepreneur turned early-stage investor and innovation expert. Andrew is currently a strategic advisor and head of Reach Labs at Second Century Ventures, consults on corporate innovation strategies and venture studios, and serves as an adjunct professor of entrepreneurship. He previously served as managing director at DreamIt Adventures, one of the top five accelerator programs in the world. He has invested in over 70 startups and written over 60 published articles for Forbes, Fortune, and other major publications. WHAT YOU'LL LEARN: In this episode, you'll discover why Andrew looks for the instinct to hustle for deals rather than focusing on the idea itself, how accelerators fill the gap between friends and family money and proper VC rounds, and why testing assumptions with a five-dollar pack of index cards can save months of development time. Andrew explains the real difference between SAFE notes and convertible notes, what makes lawyers often terrible startup advisors, and the SeatGeek origin story that proves early testing can turn a failing startup into a billion-dollar company. ANDREW'S JOURNEY: Andrew's path started with both grandfathers as entrepreneurs, one running candy shops and the other creating insurance products. Coming out of University of Chicago in the 90s when startups weren't a thing, he chose consulting before realizing the startup world had caught up. His first venture Bunk One provided internet services for summer camps and exited successfully. His second startup taught harder lessons through founder drama and failure. Angel investing came accidentally through a pharma deal he admits he had no business making, but getting lucky early hooked him. Eventually he joined DreamIt Adventures, running their New York office. KEY INSIGHTS: When evaluating founders, Andrew looks for the instinct to hustle. He shared an example of a founder who rented pencils in fifth grade for a nickel a day. Not sold. Rented. That entrepreneurial DNA shows up early and separates successful founders from everyone else. The SeatGeek story proves early testing works. A startup in his accelerator tested conversion rates early instead of waiting, discovered they were completely off, pivoted in seven weeks, and built a billion-dollar company. Lawyers often make terrible startup advisors because their incentive structure is backwards. Billing by the hour doesn't reward speed, and careers focused on avoiding mistakes rather than making deals happen. Perfect for founders thinking about raising capital, anyone curious about how accelerators work, aspiring angel investors wondering how to evaluate founders, and entrepreneurs who want practical frameworks for testing assumptions. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/andrewackerman FOR MORE ON ANDREW ACKERMAN:https://www.andrewbackerman.comhttps://www.amazon.com/Entrepreneurs-Odyssey-Approach-Startup-Success/dp/1032883545/ref=tmm_pap_swatch_0http://www.linkedin.com/in/andrewbackermanhttps://x.com/andrewackermanhttps://www.instagram.com/andrewbackerman/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! Guest Bio Andrew Ackerman is a serial entrepreneur turned early-stage investor who has invested in over 70 startups. He heads Reach Labs at Second Century Ventures, previously ran DreamIt Adventures' New York office, and teaches entrepreneurship. He has written over 60 articles for Forbes and Fortune and authored The Entrepreneur's Odyssey, written as a novel because stories stick better than frameworks. Related Episodes Episode 370 - Gerry Hays: Democratizing Venture Capital Through VentureStaking Episode 350 - Tom Dillon: Understanding Business Valuation and Exit Planning Realities Episode 89 - Sherisse Hawkins: Capital Raising Journey and Funding Realities Keywords/Tags angel investing, accelerator programs, startup evaluation, founder assessment, SAFE notes, ...
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    48 m
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