Episodes

  • Episode 404: What Makes a True Dealmaker with Sara Mostafa

    Episode 404: What Makes a True Dealmaker with Sara Mostafa
    May 20 2026
    From sketching fashion designs as a kid to leading complex M&A and private equity deals, Sara Mostafa shares what separates true dealmaking attorneys from ordinary transactional lawyers, why minority investment deals are like marriages with prenups, and what founders should understand before bringing in growth capital. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with Sara Mostafa, the newest partner at Kupfer. Sara has spent more than two decades representing private companies and entrepreneurs across M&A, financing, private equity, governance, employment, real estate, and outside general counsel matters. Like Corey, she came out of big law and built a relationship-first practice that supports clients from inception through exit. WHAT YOU'LL LEARN: In this episode, Sara explains what separates a true dealmaking attorney from an ordinary transactional lawyer, why minority investment deals require “eyes wide open,” and how experienced attorneys balance legal risk against business upside without over-lawyering. She also discusses why AI-related transactions are dominating parts of the California M&A market, why dental and medical practices are commanding strong multiples, what the 2008 recession taught her about resilience and pivoting, and how long-term client relationships often evolve into serving the next generation of entrepreneurs. GUEST'S JOURNEY: Sara originally wanted to be a fashion designer, inspired by her aunt and her childhood love of sketching clothes. While studying at the University of Pennsylvania, she unexpectedly completed her degree requirements early and took a paralegal role at Drinker Biddle & Reath in Philadelphia, which inspired her to pursue law school. She began her legal career at Cooley in San Diego, working on biotech M&A deals before deciding big law was not the long-term fit she wanted. During the 2008 Great Recession, she pivoted to immigration law and nonprofit work in Hawaii before returning full-time to business transactions. She remains licensed in both California and Hawaii. THE DESIGNER DEALMAKER: Outside of law, Sara continues to pursue creative work. Last year she bought a sewing machine and now spends much of her free time designing and making clothes, including garments she is exhibiting at the San Diego County Fair. Like others at Kupfer, she believes building a successful legal career does not require abandoning personal passions or entrepreneurial pursuits. KEY INSIGHTS: A true dealmaking attorney focuses on helping both sides move forward rather than over-lawyering every issue. Business-mindedness, perspective, and the ability to negotiate practical middle ground matter as much as technical legal skill. Minority investment deals can dramatically change how founders operate. Investors often require approval rights over major decisions and expect a future exit, which means founders need to fully understand both the growth opportunity and the downside risk. Sara believes lawyers must balance risk against opportunity. Businesses cannot grow without taking risks, and experienced attorneys help clients evaluate likelihood and impact rather than simply redlining every possible issue. She also explains that curiosity and adaptability matter more than narrow industry specialization in most transactional work. Over her career, she has represented clients across industries ranging from restaurants and fitness centers to technology, healthcare, entertainment, and construction. Perfect for founders considering outside capital, business owners planning an exit, and entrepreneurs evaluating whether their attorney is truly helping get deals done or simply executing documents. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/saramostafa FOR MORE ON SARA MOSTAFA:https://www.kupferlaw.com/ https://www.linkedin.com/in/sara-mostafa-02404211/ FOR MORE ON COREY KUPFER: https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today! Episode Highlights with Timestamps:[00:00:03] Introduction: Sara Mostafa's two decades of transactional experience and her arrival as the newest partner at Kupfer [00:03:28] The sewing machine bought last September and exhibiting garments at the San Diego County Fair [00:08:12] Why transactional work appealed and the value ...
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    42 mins
  • Episode 403: Mastering Post-Deal Integration with Mark Sims

    Episode 403: Mastering Post-Deal Integration with Mark Sims
    May 13 2026
    From experiencing an acquisition early in his career when the AT&T division he worked for was sold to a UK private equity firm, to time at $4 billion Scotts Miracle-Gro where the company created what it called the Integration Factory, Mark Sims shares 25 years of insights on why post-deal integration often determines whether M&A deals succeed or fall short, and why integration planning has to start during due diligence. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with Mark Sims, managing principal of technology solutions at Consult MSG. Mark applies 25 years of experience in strategy, M&A, and information technology across consumer products, retail, manufacturing, and private equity. He has held roles as CEO, Head of Strategy, and CIO, and now leads the technology solutions practice at a firm built around helping middle market PE-backed companies transact, transition, and transform. WHAT YOU'LL LEARN: You'll discover why post-deal integration often determines whether M&A deals succeed or fall short, why integration planning needs to start during due diligence, and what founders selling to private equity should expect when they suddenly have a boss after decades of being the boss. Mark also explains why companies trying to implement AI keep wanting to start at step five before doing the foundational data work. MARK'S JOURNEY: Mark wanted to be an architect as a kid but pursued engineering instead, earning his bachelor's and master's in Industrial Engineering. He started his career in consulting working with Fortune 500 clients, then spent about 15 years at Scotts Miracle-Gro working in corporate M&A at the $4 billion company. About three years ago he moved into the PE advisory space full time. Mark also completed the Advanced Management Program at The Wharton School. THE INTEGRATION ARCHITECT: Mark has lived all three sides of the typical PE deal. Early in his career, he watched a UK private equity firm take over the small AT&T division he worked for, eventually moving headquarters from Cleveland to Houston where the new CEO lived. At Scotts Miracle-Gro, he worked on corporate M&A and was part of the team that created what it called the Integration Factory to snap acquired businesses into the mothership. Today he advises PE-backed middle market companies on building the integration capacity their acquisition pace demands. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/marksims FOR MORE ON MARK SIMS: Website: https://consultmsg.com/ LinkedIn: https://www.linkedin.com/in/markjsims/ 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 [00:01:00] - Introduction to Mark Sims and his background [00:05:25] - Mark's career arc across public companies, Scotts Miracle-Gro, and PE advisory [00:08:54] - The founder who gets a giant check and discovers they now have a boss [00:17:32] - Why decisive integration protects the people you actually want to keep [00:22:37] - The Integration Factory at Scotts Miracle-Gro [00:29:21] - From PE to public market readiness and the standardization push [00:33:35] - Why companies want to start AI at step five before doing steps one through four [00:40:08] - What freedom means and the ability to pursue interests Guest Bio: Mark Sims is managing principal of technology solutions at Consult MSG. He applies 25 years of experience in strategy, M&A, and information technology across consumer products, retail, manufacturing, and private equity. He has held roles as CEO, Head of Strategy, and CIO, and spent about 15 years at Scotts Miracle-Gro before moving into PE advisory three years ago. Mark holds a bachelor's and master's in Industrial Engineering and completed the Advanced Management Program at The Wharton School. 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 ...
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    40 mins
  • Episode 402: Building a Transferable Business and Surviving the Exit with Nate Collins

    Episode 402: Building a Transferable Business and Surviving the Exit with Nate Collins
    May 6 2026
    From buying into a mismanaged family business on his mother's advice to selling at an incredibly high multiple to a PE-backed acquirer, Nate Collins shares how he built a transferable licensing company, what the post-exit "liminal period" really looks like, and why personal well-being is a greater predictor of company success than the reverse. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with Nate Collins, a former CEO who managed a successful exit of his international theatrical licensing company to a large PE-backed music licensing company. Nate now works as a financial advisor and certified exit planning advisor at Raymond James, helping business owners, CEOs, and their families navigate exits both financially and emotionally. WHAT YOU'LL LEARN In this episode, you'll discover why switching from cash to accrual-based GAAP accounting early creates enormous buyer confidence, how cloud-based systems reduced licensing time from four weeks to four hours, and what makes a business truly transferable. Nate explains the "liminal period" that researchers have identified in post-exit CEOs, why feelings of worthlessness can persist for years even with significant wealth, and why a Dutch study found that personal well-being is a greater predictor of company success than the reverse. NATE'S JOURNEY Nate's path to business ownership started with a phone call from his mother. A privately held theatrical licensing company owned by about 16 different families had shares available. His mother owned some from her mother, and she told Nate he needed to buy in. By any professional investment standard, it made no sense. No dividends. An overpaid CEO. No reinvestment in the business. But he trusted his mother, the price was low, and he bought in. About eight years later, the existing CEO had to be fired, and Nate stepped into leadership. He had been working in private equity and investment banking on the capital markets side and held an MBA, but none of that fully prepared him for the CEO role. He describes himself as a CEO operator, not a CEO salesperson, someone who looked at the org chart upside down and focused on supporting the rest of the team rather than being the public face. Over eight to nine years, Nate transformed the company. He oversaw roughly a 97% attrition rate while rebuilding the team, switched to accrual-based GAAP accounting on his CFO's advice, and invested in a cloud-based tech stack that made the company fully remote in 2012, two weeks before Superstorm Sandy knocked out power in lower Manhattan. The company reduced licensing time from over four weeks to under four hours. When it came time to sell, the buyer, a music licensing company roughly ten times larger, adopted the entire tech stack for its own future growth. The company sold at what Nate describes as an incredibly high multiple. Then the real challenge began. THE LIMINAL PERIOD Nate references research by South African researchers who identified the "liminal period," the time between leaving one chapter and finding the next, marked by feelings of worthlessness, confusion, and depression. Nate experienced it for three to four years, with stretches where he would sleep only three or four hours a night, flooded with anxiety. He had significant money in the bank, was an expert in financial planning, and was still convinced he would be living out of the back of his car with his family in ten years. He talks about purpose, community, and identity as the elements that collapsed overnight. A business coach later helped him add a fourth dimension, health. Together, these capture what disappears when you sell. The purpose of supporting a team every day. The community of colleagues. The identity of being CEO. And the health foundation that gets undermined when income shifts from a regular paycheck to capital you don't know how to relate to. KEY INSIGHTS Exit readiness and operational excellence are the same pursuit. Nate didn't build cloud systems or switch to GAAP accounting to sell. He did it because he hated putting out fires. Every improvement that made the business better to run also made it dramatically more transferable and valuable. Purpose comes from relevance, not soul-searching. The advice to "go find a purpose" is too abstract. What works is finding where you are relevant to others, where your presence is improving someone's life. Personal well-being predicts company success. A Dutch study found that personal well-being was a greater predictor of company success than the reverse. Business owners who wait until after the exit to invest in their own health are leaving both fulfillment and business performance on the table. Wealth management has three legs, not one. Tax strategy and asset protection are as critical as investment management, especially for business owners whose wealth is concentrated in a single illiquid asset. Build community and purpose outside your business while you still have it. The people in ...
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    48 mins
  • Episode 401: Protecting Cross-Border Deals from the Inside Out with Stephanie Pimentel

    Episode 401: Protecting Cross-Border Deals from the Inside Out with Stephanie Pimentel
    Apr 29 2026
    From the Bronx to 17 years of boots-on-the-ground relationships across Latin America, Stephanie Pimentel shares the workforce governance, cultural alignment, and regulatory pitfalls that quietly cost U.S. companies millions in cross-border deals, and the proprietary audit system she built to catch them before capital is deployed. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with Stephanie Pimentel, founder and CEO of Lumena Global Advisory, a boutique firm specializing in Latin American market entry, cross-border workforce strategy, and expansion risk management. With an executive background in multinational operations and human capital leadership, she has advised U.S. companies, private equity groups, and growth-stage founders on structuring compliant, scalable operations across Mexico, Colombia, Brazil, and beyond. WHAT YOU'LL LEARN: Why treating Latin America as a single market is one of the most expensive assumptions a company can make. How workforce governance and cultural misalignment destroy deal value after close. Why standard due diligence falls short for cross-border transactions. How a single misclassified hire in Brazil can trigger a $250,000 government charge per employee. Why an employer of record is a testing tool, not a long-term strategy. And how to assess whether your leadership team is actually ready to execute across borders. STEPHANIE'S JOURNEY: Stephanie grew up in the Bronx and started her career as an HR coordinator at $11.75 an hour in New York. She moved into telecommunications, then logistics, where work with ports pulled her into cross-border trade. Over the next 17 years she built direct relationships across Latin America at every level, sitting down with CEOs and spending time with people running daily operations on the ground. That range of experience, combined with degrees in human resource management and forensic psychology, shaped a perspective most advisors in the space do not have. KEY INSIGHTS: Latin America is not one market. Legal structures for hiring differ dramatically between Mexico, Brazil, Chile, and Argentina, and applying a uniform approach creates compliance gaps before operations even begin. Culture is an operational variable. As Stephanie puts it, "Culture is how decisions get made when no one's watching." Cultural friction begins while the ink is still wet, drives up turnover, and burns capital before it shows on any spreadsheet. Brazil's hiring penalties are severe. A misclassified hire triggers government fees of $250,000 per employee, including mandatory benefits like a lunch stipend that do not exist in the U.S. framework. Standard due diligence is not enough. Latin America requires what Stephanie calls "due diligence on the due diligence." Domestic processes do not surface what matters in each specific country, and that gap closes only after the deal is signed. Expansion readiness has four components: financial strength, operating system robustness, compliance maturity, and leadership team readiness. Strong financials without a prepared leadership team are not enough. Smaller companies can and should expand internationally. Stabilize domestic revenue first, document your operating model, and expand in layers rather than leaps. Perfect for business owners considering Latin American expansion, operators managing post-acquisition integration across borders, and advisors working on international transactions. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/stephaniepimentel FOR MORE ON STEPHANIE PIMENTEL: Website: https://lumenaglobal.com LinkedIn: https://www.linkedin.com/company/lumena-global-advisory/ 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: [00:02:28] - Introduction: Stephanie Pimentel's credentials and Lumena Global Advisory [00:09:04] - Case study: post-close, the operation is bleeding cash and the workforce is misaligned[00:10:59] - The five-pillar, 40-question proprietary audit system that grades expansion readiness [00:15:51] - Culture as an operational variable: why it burns capital before it shows on any spreadsheet[00:27:30] - Due diligence on the due diligence, vetting intermediaries, and building a compliant foundation[00:36:55] - ...
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    42 mins
  • 400 Episodes, One Mission: The Story Behind DealQuest with Corey Kupfer

    400 Episodes, One Mission: The Story Behind DealQuest with Corey Kupfer
    Apr 22 2026
    Nearly 8 years, 400 episodes, and close to 30,000 monthly listens: Corey Kupfer shares how the DealQuest Podcast started as a solution to a real business problem, what the guest relationship strategy actually produces for a professional services firm, and why most podcasters quit before the compounding effect kicks in. In this milestone episode of the DealQuest Podcast, host Corey Kupfer hands the mic to his law firm partner Brian Meegan for a candid look inside nearly eight years of podcasting. Corey is an expert strategist, negotiator, and dealmaker with more than 35 years of professional deal-making experience, and the creator of the DealQuest Podcast. Brian Meegan is Corey's partner at Kupfer Law and a longtime member of Entrepreneurs' Organization, where the two originally met. WHAT YOU'LL LEARN: How a frustration with staying connected at scale led to a podcast now generating close to 30,000 listens per month, why the guest relationship is more valuable than the listener base for a professional services business, what "pod fade" is and why more than 85% of podcasts never reach 15 episodes, and the distinction between born dealmakers and situational dealmakers and why it matters for entrepreneurs who think deals aren't for them. ORIGIN STORY: The podcast started as a business problem. As the law firm grew, staying genuinely connected with clients, referral sources, and industry partners at scale became impossible. Authority marketing offered a path. An Entrepreneurs' Organization event in New York, where Gimlet Media founder Alex Bloomberg spoke candidly about starting a podcast company, made the medium click. The show launched in 2018 as Fueling Deals, rebranded to DealQuest about a year and a quarter in, and settled into the format it holds today: a defined open, a defined close, and everything in between is open conversation with no pre-prepared questions. KEY INSIGHTS: The three-part value model for a professional services podcast covers staying top of mind with your existing network, credibility and searchability when a prospect googles you, and actual search-driven client acquisition. All three have produced meaningful results for the DealQuest practice. The guest relationship is the most underestimated asset. Of approximately 300 guest interview episodes, the direct business and referrals from those guest relationships have outweighed what came from the broader listener base. The relationship starts from a place of value creation because the first thing Corey does is give guests access to a meaningful audience. Pod fade is real. More than 85% of podcasts don't reach 15 episodes. Corey's posture from the start was either commit to hundreds of episodes or don't start. Pick a medium you're genuinely energized by, because the energy in the conversation is not replicable with a format you find grinding. Born dealmakers and situational dealmakers are both real. People who treat dealmaking as an exclusive talent tend to opt out before they try. Deals can be learned, and there are structures where risk is easily managed. That's the premise behind Corey's talk called There's a Deal for That: any business challenge or opportunity has a potential deal solution worth at least considering. Perfect for entrepreneurs and business owners considering whether a podcast makes sense for their business, professionals thinking about authority marketing strategy, and dealmakers curious about what nearly 400 conversations about deals has taught someone with 35 years of deal-making experience. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/episode400 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 [00:03:35] - The origin: Authority marketing, the scale problem, and why a podcast [00:06:45] - The Gimlet Media moment: How Alex Bloomberg's story made podcasting click [00:11:51] - Fueling Deals becomes DealQuest: The rebrand and format evolution [00:14:50] - Growth from 60-80 listens to close to 30,000 per month [00:18:26] - The lurker phenomenon: Why public engagement undercounts your real reach [00:20:28] - The three-part value model for a professional services podcast [00:23:06] - The guest strategy: Why guest relationships outperform ...
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    41 mins
  • 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 mins
  • 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 mins
  • 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 mins