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 399: From Dot-Com Survivor to Fractional CFO with Salvatore Tirabassi

    Episode 399: From Dot-Com Survivor to Fractional CFO with Salvatore Tirabassi
    Apr 15 2026
    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 ...
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    42 m
  • Episode 398: Building a Business Partnership That Lasts with Leah and Becca Wiser

    Episode 398: Building a Business Partnership That Lasts with Leah and Becca Wiser
    Apr 8 2026
    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, ...
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    47 m
  • Episode 397: Achieving 97% Client Retention in Practice Transitions with Jerry Blakely

    Episode 397: Achieving 97% Client Retention in Practice Transitions with Jerry Blakely
    Apr 1 2026
    From buying his first practice from a trusted friend to achieving 97% client retention when selling his own 700-client firm, Jerry Blakely shares the emotional strategies that make RIA practice transitions succeed when so many others fail. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with Jerry Blakely, a CFP and financial advisor with over 40 years of experience in the wealth management industry. Jerry has been on both sides of practice transitions and now consults RIA firms on helping selling advisors pass client relationships to buying advisors with maximum retention. WHAT YOU'LL LEARN In this episode, you'll discover why buying a practice means buying client relationships and what happens when those relationships fail to transfer. Jerry explains why selling advisors without clear exit timelines struggle to complete transitions, how a one-year in-office handoff with joint client meetings dramatically increases retention, and what he discovered when consulting practices that had never told their clients about the sale. You'll also learn why keeping key staff provides crucial continuity and how authentic storytelling creates the emotional anchors that keep clients from leaving. JERRY'S JOURNEY Jerry's first deal came through a close friend he met at Life Underwriters Association meetings. Gordon was older and ready to retire. They compared notes, realized they had extremely similar practices, and decided to use the same appraisal firm and even the same attorney. Everyone says not to do that, but the trust between two friends made the deal work. Gordon physically moved into Jerry's office for one year. They met personally with every single client together in what Jerry calls a "great big handoff routine." Most of those original clients were still with the practice when Jerry sold it himself ten years later. KEY INSIGHTS When you do a buy-sell agreement in wealth management, you're buying client relationships. If those relationships don't stick, you've bought a distressed asset and the buyer won't have money to pay the seller. Both parties have skin in the game to make the emotional transfer work. Having a targeted exit date changes everything. Jerry wanted to be out by age 70. He told clients directly, "Don't get mad at me, but I'm getting old." They understood because they were living similar life stages. Jerry's practice manager had been with him for 20 years and remained six more years after he sold. Clients who went through five different advisor changes stayed because they could still call the familiar person at the front desk. One advisor Jerry consulted couldn't tell clients she was retiring because she felt guilty about her success. Once she realized clients would celebrate her dream of building a cabin on a lake, she developed a script and moved forward within three weeks. Perfect for financial advisors planning succession, RIA firm owners acquiring practices, and any business leader where client retention drives enterprise value. FOR MORE ON THIS EPISODE:https://www.coreykupfer.com/blog/jerryblakely FOR MORE ON JERRY BLAKELY:https://www.cffp.edu/who-we-are/jerry-blakely 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. Episode Highlights with Timestamps:[00:12:28] - Introduction and Jerry Blakely's background as a CFP with 40+ years of experience [00:13:45] - What Jerry wanted to be as a kid and surrogate father figures in marching band[00:14:28] - First deal with Gordon and the trust-based approach to practice acquisition[00:17:04] - The one-year in-office transition with joint client meetings [00:18:12] - Getting hired as a consultant and discovering why other acquisitions struggled[00:27:44] - Why Jerry sold his practice and having a targeted exit date of age 70 [00:30:48] - Visiting offices where sellers had never told clients about the transition [00:35:05] - "Don't get mad at me, but I'm getting old" and authentic communication[00:37:24] - The 97% retention rate reveal [00:41:09] - The practice manager as anchor and why continuity matters [00:49:36] - The advisor who felt guilty about retiring [00:53:49] - The $5 million client whose father owned ski resorts [00:59:23] - What freedom means to Jerry Guest Bio:Jerry Blakely was a successful CFP and financial advisor for over 40 years. He bought practices and sold practices during that time, achieving approximately 97% client retention when he sold his own 700-client firm. He now consults RIA firms on helping selling advisors pass client relationships to buying advisors with maximum retention. Host Bio:Corey Kupfer is an expert ...
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    47 m
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