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 your business will forget you existed the day after you sell. Relationships and meaning outside the company are how you avoid the worst of the liminal period. Perfect for business owners planning exits, entrepreneurs thinking about transferability, and founders who worry about what comes after the sale. FOR MORE ON THIS EPISODE https://www.coreykupfer.com/blog/natecollins FOR MORE ON NATE COLLINS LinkedIn: https://www.linkedin.com/in/nate-collins/ Company: https://www.raymondjames.com/founderwealthstrategies/events 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 [00:03:23] - Introduction and bio [00:07:05] - First deal, buying into a family-owned licensing company on his mother's recommendation[00:09:19] - Transforming the company with 97% attrition and building a dynamic team[00:14:03] - How theatrical licensing works, from school plays to international tours [00:18:52] - Switching to accrual-based GAAP accounting and the impact on buyer confidence [00:20:25] - Cloud systems, surviving Superstorm Sandy, and reducing licensing time from four weeks to four hours [00:25:30] - Written processes and procedures as a transferability driver [00:30:04] - Being a CEO operator versus a CEO salesperson [00:32:12] - The liminal period, post-exit depression, and the smallest violin problem [00:36:08] - Losing purpose, community, and identity overnight after the sale [00:41:04] - Finding purpose through relevance to others [00:45:51] - Dutch study linking personal well-being to company success Guest Bio Nate Collins is a former CEO who managed a successful exit of his international theatrical licensing company to a large PE-backed music licensing company in 2019. The company was a mid-market business with roughly 100 employees and mid-eight figures in revenue. Before becoming CEO, Nate worked in private equity and investment banking. He now works as a financial advisor and certified exit planning advisor at Raymond James, helping business owners, CEOs, and their families with tax mitigation, estate planning, financial planning, and preparation for life after exit. He runs a quarterly business exit planning workshop and is completing a workbook to guide business owners through the exit process. 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 strategic deals to accelerate growth. From large mergers and acquisitions to capital raising, joint ventures, strategic alliances, real estate deals, and more, this show discusses the full spectrum of deal-driven growth strategies. Get the confidence to pursue deals that will help your company scale faster. Related Episodes Dave Hersh: The Psychology Behind Successful Exits (referenced in this episode for the "smallest violin" concept around post-exit struggles) Episode 366 - Jodi Hume: Founder Exits and the Emotional Journey Behind Major Business Decisions Episode 328 - Richard Manders: Post-Exit Transitions and Finding Purpose After Selling Your Company Episode 302 - Laurie Barkman: Preparing for a Successful Exit with Business Transition Insights Episode 330 - Pete Mohr: Building Enterprise Value and Exit Readiness Keywords/Tags post-exit depression, liminal period, exit planning, business transferability, CEO identity crisis, company valuation drivers, personal well-being business success, accrual-based accounting, exit readiness, licensing business model, sell your business preparation, post-sale anxiety, purpose after exit, mid-market exit, roll-up acquisition, business systems documentation, cloud-based operations, wealth management entrepreneurs, tax strategy business owners, certified exit planning advisor
