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 ...
    Más Menos
    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, ...
    Más Menos
    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 ...
    Más Menos
    47 m
  • 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 ...
    Más Menos
    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 ...
    Más Menos
    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 ...
    Más Menos
    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, ...
    Más Menos
    48 m
  • Episode 392: How to Actually Get Your Deals Across the Finish Line with Corey Kupfer

    Episode 392: How to Actually Get Your Deals Across the Finish Line with Corey Kupfer
    Feb 25 2026
    After 35+ years of closing deals across industries, Corey Kupfer shares the practical strategies that separate deals that close from deals that die in the final stretch. This remastered solocast from the early days of DealQuest delivers timeless advice on getting deals across the finish line. In this solocast episode of the DealQuest Podcast, host Corey Kupfer breaks down the critical factors that determine whether your deal actually closes or falls apart at the last minute. Drawing from decades of experience as an M&A attorney, entrepreneur, and dealmaker, Corey addresses the mental traps, preparation gaps, and emotional triggers that derail otherwise successful transactions. WHAT YOU'LL LEARN: In this episode, you'll discover why mentally closing a deal before it actually closes is the biggest mistake dealmakers make, and how "spending the money in your mind" sabotages your focus and negotiating position. Corey explains the concept of pre-due diligence and why preparation before the LOI stage prevents deals from falling apart during buyer scrutiny. You'll learn how to identify your true bottom line and get total clarity on what's acceptable and what's not. The episode covers how ego and emotional attachment blow deals that would otherwise succeed, the strategic balance of bringing in key stakeholders while maintaining confidentiality, and how to keep deal momentum alive through consistent engagement with your professional team. WHY DEALS DIE: Most deals don't fall apart because of bad terms or major due diligence discoveries. They fall apart because someone mentally checked out too early. The moment you sign the LOI and start treating the deal as done, you stop focusing on the critical work still required. You stop keeping your due diligence clean. You stop maintaining pace. You stop staying hungry for the close. The other side senses this shift, issues arise that could have been managed, and momentum dies. PRE-DUE DILIGENCE PREPARATION: One of the best ways to ensure deals close is preparation that happens before negotiations even heat up. If you're selling your company, experienced advisors know what buyers will examine. If you're raising capital, they know what investors will scrutinize. The goal is to be fully prepared and looking great before their team starts asking questions. Many deals fall apart during due diligence because sellers haven't done this preparation work. When there's smoke, buyers think there's fire. One issue makes them worry about ten others they haven't found yet. TRUE BOTTOM LINE CLARITY: This connects to a fundamental negotiating principle from Corey's Authentic Negotiating book. You need total clarity on exactly what's acceptable and what's not acceptable to you. When things shift unexpectedly, whether the economy changes, due diligence reveals issues, a key employee leaves, or you lose a major client, that foundation of clarity determines whether you navigate the disruption or let it derail everything. If you don't know your true bottom line, these disruptions can easily prevent you from ever reaching closing. MANAGING EGO AND ATTACHMENT: As deals progress, watch for ego and emotional attachment on both sides. When the other party raises issues close to closing, you need clarity to analyze whether those issues actually matter versus reacting because you feel triggered. Sometimes people blow deals not because the terms became unacceptable, but because they got tired, frustrated, or insulted. Don't let triggering emotions destroy a deal that could be very good or lucrative for you. STAKEHOLDER ALIGNMENT: Deals can fail at the last minute because the principals assume alignment that doesn't exist. They go to key employees, minority owners, or investors expecting buy-in and discover it isn't there. The balance between confidentiality and getting necessary stakeholder alignment requires strategic thinking. Especially if you're selling your company, you have to weigh not being seen as "in play" on the marketplace and not having employees get spooked against the risk of bringing key folks in too late. MAINTAINING MOMENTUM: Work closely with your team and professionals to keep the pace of the deal moving forward. Deals die when people lose interest or momentum simply fades. Consistent engagement, timely responses to information requests, and staying available to work through inevitable issues keeps deals on track. Perfect for business owners preparing to sell, executives pursuing acquisitions, entrepreneurs raising capital, and anyone involved in transactions who wants to understand why deals succeed or fail in the final stretch. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/how-to-close-deals 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, ...
    Más Menos
    10 m