Exiting In Silicon Valley: Derek Collison On Cloud Wars, Kubernetes, And Synadia The Exit

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The 30% Mistake: Why Most Founders Leave Money on the Table with Linda Hamilton 31:12

2 days ago31:12

31:12

Want a quick estimate of how much your business is worth? With our free valuation calculator, answer a few questions about your business, and you’ll get an immediate estimate of the value of your business. You might be surprised by how much you can get for it: https://flippa.com/exit -- In this episode of The Exit: Linda Hamilton, a Certified Exit Planning Advisor and longtime CPA, shares practical strategies for business owners preparing for a future exit, emphasizing the importance of readiness, clean financials, and documented systems. Key Takeaways: Exit Planning is About Optionality, Not Just Selling Many business owners avoid thinking about exits too early, but Linda argues that preparing early builds resilience and optionality, not just a path to sell. The Cost of Not Preparing Citing a 30% valuation gap between male and female founders, Linda underscores how lack of preparation—especially around clean books, contracts, and succession—can significantly impact sale outcomes. Readiness vs. Attractiveness Linda encourages using assessments to evaluate both how attractive your business is to a buyer and how ready you are to exit. She shares a story of a founder nearly derailing a deal by not securing key employee agreements. Key Indicators of Exit-Readiness - Critical elements include: Clean, audited financials Signed client/vendor contracts Repeatable and documented systems Cash flow visibility and control over AR/AP Transferability & Systemology As a certified systemologist, Linda highlights the importance of mapping your customer journey and operational systems to ensure the business can run without you—critical for buyer confidence and deal value. Building a Support Team Successful exits rely on coordinated advisors: CPAs, attorneys, brokers, and wealth advisors. A SIPA-certified exit planner often acts as the “quarterback” to align everyone's efforts with the owner’s goals. Timing & Purpose Timing an exit is personal. Many owners regret selling too soon because they lack a post-exit purpose. Linda encourages planning for life after the sale as part of the overall exit strategy. Empowering Female Founders Linda advocates for financial fluency and readiness assessments to help women negotiate from a position of strength. Confidence comes from awareness—knowing your numbers, your risks, and your value. Final Advice: Linda wishes she had done her own business readiness assessments earlier in her career, highlighting how early preparation can influence smarter long-term decisions. -- Linda Hamilton is a CPA and CEPA, (Certified Exit Planning Advisor) who is passionate about helping women business owners achieve financial fluency to grow, profit & scale. Linda founded Grow Profit Scale™, a coaching and mastermind program designed to empower women entrepreneurs with financial fluency, profit amplification, and scalable business strategies. In addition to Grow Profit Scale, Linda is also the founder of Linda A. Hamilton CPA LLC, where Linda and her team provide accounting, tax, and strategic financial planning services. With over 35 years as a CPA, CGMA, CEPA, and SYSTEMologist®, she has helped countless business owners develop strong financial systems, improve profitability, and plan for successful exits. Linda on LinkedIn: https://www.linkedin.com/in/lindahamiltoncpa/ Websites: https://www.growprofitscale.com/ - https://www.lahcpas.com/ -- The Exit—Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You’ll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on flippa.com/the-exit-podcast/…

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When to Let Go: The Emotional Side of Selling Your Business – Lessons from Jonathan Bennett 28:41

9 days ago28:41

28:41

Want a quick estimate of how much your business is worth? With our free valuation calculator, answer a few questions about your business, and you’ll get an immediate estimate of the value of your business. You might be surprised by how much you can get for it: https://flippa.com/exit -- In this episode of The Exit: Host Steve McGarry sits down with Jonathan Bennett, advisor at Clearly Then and former founder of a successful B Corp consulting firm, to unpack the emotional journey of exiting a business—something rarely discussed, but profoundly impactful. Jonathan shares his own story of selling his company through a gradual management buyout, and how the decision started with a casual walk in Dublin and a question from his wife. The episode dives into the often-overlooked inner challenges that founders face—identity loss, grief, and the fear of letting go. “The easy part is the legal and financial stuff,” Jonathan says. “The hard part is emotional.” You’’ll learn: Why selling at your peak (not in burnout) is critical How to choose the right successor without hanging on too long Why empty promises during a handover can backfire What life after an exit looks like—and how to fill the void with purpose Smart negotiation tips, including how to uncover the real motivations of a buyer Whether you're planning to exit soon or just building for the long game, Jonathan’s mix of practical wisdom and emotional intelligence will give you a fresh perspective on what it really means to walk away from something you built. "Don't wait until you're depleted to sell—get off the stage while the crowd is still clapping." – Jonathan Bennett -- Jonathan Bennett is an advisor and executive coach for purpose-driven leaders who need help solving their organization’s toughest obstacles. With experience in urban, rural, remote, and First Nations communities, Jonathan’s expertise is in social purpose business strategy, governance, branding, change, and communications. His coaching draws on 25 years of creativity and leadership success as a CEO, board member, and founder, and he is known for his deep-listening and his breakthrough solutions that create insights and new strategies. Jonathan on LinkedIn: https://www.linkedin.com/in/bennettjonathan/ Link to Private Podcast: https://clearlythen.com/listen Website: https://clearlythen.com/ -- The Exit—Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You’ll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on flippa.com/the-exit-podcast/…

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From Engineering to Exits – Christy Brown’s Journey Building & Selling Businesses 36:04

16 days ago36:04

36:04

Want a quick estimate of how much your business is worth? With our free valuation calculator, answer a few questions about your business, and you’ll get an immediate estimate of the value of your business. You might be surprised by how much you can get for it: https://flippa.com/exit -- In this episode of The Exit: Steve McGarry sits down with Christy Brown, CEO of Dr. Noze Best, to unpack her remarkable journey from engineer to multi-exit entrepreneur. Raised in a family of gritty builders and innovators, Christy shares how early exposure to a family-run real estate business inspired her transition from corporate consulting to launching her first eCommerce-focused agency in the early 2000s. Key topics discussed: The Power of Accelerators: Christy breaks down how accelerators build founder confidence, drive growth, and connect entrepreneurs with critical networks. Empowering Women Entrepreneurs: She details her role in leading a women-focused accelerator that graduated 260+ founders, contributing over $2.5B in economic impact. Exit Strategy Insights: Christy shares candid lessons from her exits—including a public company earn-out—and the emotional and cultural shifts that follow a sale. Misconceptions about Exits & Venture Funding: From unrealistic timelines to overestimated payoffs, Christy demystifies what exits actually look like behind the headlines. Personal Advice: From reverse-engineering your life around your business to negotiating with clarity, Christy offers practical guidance for both aspiring and seasoned founders. Final takeaway: “Scaling is a strategy. Exiting is personal.” – a reminder that success is defined not just by valuation, but by the life you build alongside your business. -- Christy Brown is a proven leader with twenty years of leadership in entrepreneurship, customer development, and strategic innovation and solutions. Christy is a known resource for innovating traditional business models and scaling emerging businesses from inception to exit. She is a solution-oriented leader with expertise in technology, financial, and operational areas of growth stage businesses. Christy brings a heavy-duty management acumen with a focus on culture, diversity of thought, and design thinking. Her experience drives improvements and scale in organizations, fostering a culture of transformational change. Christy Brown on LinkedIn: https://www.linkedin.com/in/christy-brown-a54aa0/ Website: https://drnozebest.com/ -- The Exit—Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You’ll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on flippa.com/the-exit-podcast/…

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Scaling with Purpose: Anne Mahlum’s $100M Success Story 30:43

23 days ago30:43

30:43

Want a quick estimate of how much your business is worth? With our free valuation calculator, answer a few questions about your business, and you’ll get an immediate estimate of the value of your business. You might be surprised by how much you can get for it: https://flippa.com/exit -- In this episode of The Exit: entrepreneur Anne Mahlum shares her incredible journey from founding a nonprofit running club for homeless men to building Solidcore, one of the fastest-growing fitness studio chains in the U.S. After scaling to 100 studios and weathering the chaos of COVID, Anne exited the business on her own terms with a $100M payday—negotiating not only her valuation but her taxes and an additional $10M kicker. She reveals how she planned her exit from day one, built bench strength to replace herself, and why founders shouldn’t be afraid to ask for more. Anne also dives into the dangers of taking on preferred equity, the power of clear end goals, and the importance of sharing wealth with the team that helped build it. Her parting advice? Think big, stay bold, and trust yourself—because no one else will see your vision the way you do. -- Anne Mahlum is a founder, entrepreneur, CEO, philanthropist, motivational speaker and athlete whose mission is to help as many people as possible live their most optimized lives. Anne's entrepreneurial ventures have resulted in a personal net worth of over $100M and an impact on hundreds of thousands of lives. She is the Founder and former Executive Chairwoman of [solidcore], a fast-growing boutique fitness company with over 100 locations in the U.S. Anne sold her shares of [solidcore] in April 2023 for an undisclosed amount and shared millions with her employees who she valued for staying by her side. A lifelong visionary, Anne is also the founder of Back on My Feet, a national non-profit organization that uses running as a vehicle to help those experiencing homelessness change the way they see themselves and become empowered to change their lives. Anne Mahlum on LinkedIn: https://www.linkedin.com/in/anne-mahlum/ Website: https://www.annemahlum.com/ Instagram: https://www.instagram.com/annemahlum -- The Exit—Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You’ll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on flippa.com/the-exit-podcast/…

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The Psychology of Selling a Business with Anthony Citrolo, NYBB Group 31:14

30 days ago31:14

31:14

Want a quick estimate of how much your business is worth? With our free valuation calculator, answer a few questions about your business, and you’ll get an immediate estimate of the value of your business. You might be surprised by how much you can get for it: https://flippa.com/exit -- In this episode of The Exit: What really happens when a founder decides it’s time to sell? In this powerful and practical episode, Steve McGarry sits down with Anthony Citrolo, CPA, serial entrepreneur, and managing partner at the NYBB Group, to unpack what really goes into preparing a business for sale. But this isn’t your average M&A conversation. Anthony takes us behind the curtain to reveal the emotional, psychological, and strategic decisions founders face as they approach a life-changing exit. Here’s what you’ll learn: - Why the real exit plan starts the day you launch the business - The #1 mistake founders make when valuing their business - How to prepare your business (and yourself) before a buyer ever knocks - The danger of “key man” risk - and how to build a business that runs without you - What buyers really want: cash flow, scalability, and low concentration - Why 75% of sellers are unhappy post-exit - and how to avoid that fate - How to spot and address hidden risks that could kill your valuation “Most founders don’t realize they’re living vicariously through their business until it’s too late.” Anthony Citrolo With 20+ years in the trenches helping family-owned and founder-led businesses exit, Anthony shares war stories (like Frank, the manufacturer with 98% of revenue tied to 7 customers), practical frameworks, and wisdom earned through decades of hands-on deals. If you're a founder, even if you're years from selling, this episode will change how you think about growth, leadership, and legacy. Listen now to learn how to not just sell your business—but exit on your terms. -- Anthony J. Citrolo is a Managing Partner and Founder of The NYBB Group, LLC, the Exit Strategy Lab and NYBB Commercial Real Estate. Anthony’s clients include privately held companies and family-owned businesses. These are typically companies with revenue of $5M to $100M. Anthony represents HVAC, industrial service, finance, manufacturing, distribution, transportation, healthcare and all service companies. He helps these owners develop a clear and cohesive exit strategy, works to know and improve valuation and actively represents them in a sale or acquisition in a Merger and Acquisition transaction as their advisor and intermediary. Anthony is a CPA and a CEPA (Certified Exit Planning Advisor) and develops comprehensive strategies for owners and families. He also has completed the CEPA course and is a Certified Exit Planning Advisor. In addition, Anthony is a Certified Merger & Acquisition Advisor AND Certified Exit Map Coach. Anthony on LinkedIn: https://www.linkedin.com/in/anthonycitrolo/ Website: https://thenybbgroup.com/ -- The Exit—Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You’ll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on flippa.com/the-exit-podcast/…

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Fortune Favors the Brave: How Lisa Jones is Building a $50M Exit with Kindness, Grit & Systems 32:32

5 weeks ago32:32

32:32

Want a quick estimate of how much your business is worth? With our free valuation calculator, answer a few questions about your business and you’ll get an immediate estimate of the value of your business. You might be surprised by how much you can get for it: https://flippa.com/exit -- In this episode of The Exit: Lisa Jones, founder and CEO of Shecom, shares her raw and powerful journey from frustrated corporate employee to seasoned entrepreneur with three exits—and a $50 million goal in sight. After being fired just shy of her probation period, Lisa launched her first business and never looked back. She reveals the hard lessons from early ventures, emphasizing the need for systemization, profitability, and eliminating key-person risk. Now building her “golden ticket” company, Shecom, Lisa leads with vulnerability, kindness, and mission-driven culture, rallying her all-female team around a shared vision. She stresses the power of community, first-party data, and recurring revenue in scaling a sustainable DTC brand. With painful missteps—like nearly going broke on a Bali holiday—behind her, Lisa urges founders, especially women, to get financially literate and think bigger, sooner. Her motto? “Fortune favors the brave.” And she’s boldly proving it. -- Lisa Jones is a passionate E-commerce expert and builder of 3 x multi-million dollar e-commerce brands. Lisa is most famous for co-founding Ecoriginals, the world's greenest nappy and wipes brand, which she sold to a private equity investor in 2020, Lisa is now busy building SHE-com, a global empire for women with e-commerce brands with a community of over 40,000 with a team of 45. Lisa on LinkedIn: https://www.linkedin.com/in/lisa-jones-shecom/ Website: https://shecom.co/ -- The Exit—Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You’ll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on flippa.com/the-exit-podcast/…

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The Exit That Never Happened: Turning a Family Failure Into a Mission to Help Founders Exit Right with Ben Brickweg 34:09

6 weeks ago34:09

34:09

Want a quick estimate of how much your business is worth? With our free valuation calculator, answer a few questions about your business and you’ll get an immediate estimate of the value of your business. You might be surprised by how much you can get for it: https://flippa.com/exit -- What happens when an eight-figure exit falls apart? For Ben Brickweg, it sparked a decades-long mission to ensure no other founder has to experience the same heartbreak his family did. In the latest episode of The Exit, Ben — founder of Exitworthy, attorney, and seasoned M&A advisor — pulls back the curtain on what really goes wrong in business exits… and how to fix it. What You’ll Learn: The family deal that blew up and why it changed Ben’s life forever How Ben accidentally fell into M&A and worked on 200+ deals his first year Why most founders are unprepared to exit — and how to change that The three-part “Value Mountain” framework: Valuation, Sellability, and Transferability The biggest legal mistakes business owners make when selling Why private equity offers often shift post-LOI — and what to do about it How lifestyle inflation and poor financial planning derail more exits than you'd think What it really means to build an “exit-worthy” business Ben doesn’t just talk theory. He’s been on every side of the table — founder, lawyer, broker, buyer — and he’s seen deals thrive, collapse, and quietly destroy the dreams of unprepared sellers. His advice? Don’t wait until you’re ready to sell. Build your business like you're going to exit — from day one. This is a no-BS, deeply practical episode for anyone who owns a business and wants optionality — whether that means exiting now, or 10 years from now. -- Personal &/or Company Bio: Ben Brickweg has worked with over 2,000 business owners, helping them grow, protect, and sell their companies the right way. He runs two companies, Sagewood Business Advisors and Lodgepole Law, both built to help business owners navigate complex deals and legal challenges. Sagewood Business Advisors is a boutique M&A firm that helps owners understand their value, structure strong deals, and exit on their terms. Lodgepole Law is a provider of fractional general counsel services for acquisition entrepreneurs who need a proactive legal strategy, not last-minute chaos and hourly meters. He is also the creator of Exit Worthy, a platform that includes the podcast, training materials, and resources to help business owners get serious about preparing for a real exit; and Business Legal Fortress, bridging the gap between legal template stores and full-service firms, giving business owners affordable, effective legal protection without the unpredictability of hourly fees. Ben on LinkedIn: https://www.linkedin.com/in/benbrickweg/ Website: https://gosagewood.com/ - https://exitworthy.com/ - https://lodgepolelaw.com/ -- The Exit—Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You’ll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on flippa.com/the-exit-podcast/…

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From $100 to a $20 Million Exit to Intuit: Nellie Akalp on Building, Selling, and Starting Again 35:36

7 weeks ago35:36

35:36

Want a quick estimate of how much your business is worth? With our free valuation calculator, answer a few questions about your business and you’ll get an immediate estimate of the value of your business. You might be surprised by how much you can get for it: https://flippa.com/exit -- In this episode of The Exit: Nellie Akalp, founder and CEO of CorpNet, takes us on a no-fluff journey from launching her first business with just $100 to securing a 20x EBITDA exit to Intuit — all before turning 32. Nellie shares: How she and her husband bootstrapped MyCorporation from their apartment. What made their business irresistible to Intuit (spoiler: no debt, no investors, ultra-clean books). Why the post-acquisition “early retirement” didn’t last — and how that led to launching CorpNet in 2009 during the height of the recession. The pivotal B2B pivot that transformed CorpNet’s growth, including the launch of their Partner Program. How COVID turned into a major growth inflection point, scaling the team from 15 to 200 Why boundaries and mental wellness are non-negotiable for modern founders.. If you’re a business owner thinking about exit strategy, reinvention, or how to scale sustainably while protecting your peace — this episode is packed with golden insights from someone who’s lived it twice. -- Nellie Akalp is an entrepreneur, small business advocate, and mother of four little rockstars. As founder and CEO of CorpNet.com, she has helped more than half a million entrepreneurs start their businesses. Through CorpNet.com, Nellie has also partnered with business professionals such as attorneys, CPAs and more as their silent fulfillment partner helping them incorporate and form LLCs for their clients. Nellie has been named a Top 100 Small Business Influencer by Small Business Trends for the past four years and counting. In 2016 she was named Women Business Owner of the Year by NAWBO VC and her company, CorpNet.com, has been recognized on the Inc. 5000 list of fastest-growing privately-held companies in America in 2015 and 2016. Website: https://www.corpnet.com/ Instagram: https://www.instagram.com/corpnet/ LinkedIn: https://www.linkedin.com/company/corpnet.com/ Nellie on LinkedIn: https://www.linkedin.com/in/nellieakalp/ -- The Exit—Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You’ll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on flippa.com/the-exit-podcast/…

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Rethinking the Exit: Charlie Lass on Startups, Burnout, and Building for Freedom 33:48

8 weeks ago33:48

33:48

Want a quick estimate of how much your business is worth? With our free valuation calculator, answer a few questions about your business and you’ll get an immediate estimate of the value of your business. You might be surprised by how much you can get for it: https://flippa.com/exit -- In this episode of The Exit: Charlie Lass, founder of Humble Inc., shares the highs and lows of 20 years in entrepreneurship. From early film ventures to million-pound deals in emergency tech, Charlie reveals lessons from building startups, missteps with equity, and redefining what an “exit” truly means. Now focused on sustainable autonomy through Humble, a content platform for creators, he urges founders to prioritize well-being, honest partnerships, and building for longevity, not just valuation. -- Charlie Lass is a career entrepreneur with successful exits in the UK & US who mentors ambitious founders and consults for high-potential companies. Charlie is a mentor to 500+ ambitious and awesome founders and freelancers. He has coached, advised and supported individuals at all stages of funding and launch with a particular focus on the early stage strategy and tactics, fundraising, pricing, marketing, brand positioning and tone of voice. Charlie is the Founder of Humble Inc, a content platform for entrepreneurs, “wantrepreneurs”, and freelancers across the globe. Humble is dedicated to providing access to real experts who care, offering personalized guidance in a world overwhelmed by self-proclaimed gurus. Humble values passion, humility, and real experience over fame and follower counts. They believe that your mental health matters, and that they are there to support your journey with facts, not clickbait. Charlie on LinkedIn: https://www.linkedin.com/in/charlielass/ Website: https://www.humble.inc/ -- The Exit—Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You’ll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on flippa.com/the-exit-podcast/…

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Exit-Ready: How Women-Led Businesses Can Scale, Sell, and Own Their Worth with Aggie Chydzinski and Cristy O’Connor 35:12

9 weeks ago35:12

35:12

Want a quick estimate of how much your business is worth? With our free valuation calculator, answer a few questions about your business and you’ll get an immediate estimate of the value of your business. You might be surprised by how much you can get for it: https://flippa.com/exit -- In this episode of The Exit: Aggie Chydzinski and Cristy O’Connor, co-founders of Athena Advisory Collective and hosts of the Badass Women in Business podcast share share the real, tactical advice most founders never hear. Between them they have had multiple exits—including turning around failing fitness franchises and scaling operations in manufacturing and tech. Whether you’re just starting out or already thinking about your second act, this episode will challenge how you think about value, preparedness, and exit timing—especially for women-led businesses. What you'll learn: Why building a business that runs without you is the path to premium valuation The Five Ds that force exits—and how to be ready before one hits Why human capital, culture, and clean financials matter more than you think How underpricing services holds women founders back—and how to fix it Why founders (especially women) need to show up with unapologetic confidence—and pitch like they mean it How Cristy rebuilt toxic team cultures and why hiring aligned people from day one is crucial The role of "woo" (like astrology-based assessments) in team alignment and enterprise value Plus, they break down the gender gap in VC and offer a bold but refreshing take: stop siloing women. Fund the best businesses—no matter who’s leading them. This is a candid, insightful, and empowering conversation for any founder—but especially those ready to own their value and prepare for a life-changing exit. -- Aggie Chydzinski and Cristy O'Connor are the co-founders of Athena Advisory Collective. At Athena, they partner with women-owned businesses and partnerships navigating the real complexities of growth. Athena works alongside these businesses to implement strategies that grow enterprise value and strengthen exit readiness. Whether it is optimizing sales, improving operations, or developing leadership, they help these owners build a business that is scalable, aligned, and ready for what is next. With a focus on clarity, accountability, and measurable impact, Athena Advisory Collective supports the vision of these women-owned businesses every step of the way. Website: https://www.athenaac.com/ Instagram: https://www.instagram.com/athenaadvisorycollective Badass Women in Business Podcast: https://badasswomeninbusinesspodcast.com/ -- The Exit—Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You’ll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on flippa.com/the-exit-podcast/…

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Inside the Minds of Billionaires: Deal Structuring, Exiting Smart, and the Power of Long-Term Focus with Richard C. Wilson 36:43

10 weeks ago36:43

36:43

Want a quick estimate of how much your business is worth? With our free valuation calculator, answer a few questions about your business and you’ll get an immediate estimate of the value of your business. You might be surprised by how much you can get for it: https://flippa.com/exit -- In this episode of The Exit: Richard C. Wilson, founder of Family Office Club—the world’s largest community of family offices—joins us for a no-fluff, high-value conversation on raising capital, exiting strategically, and building relationships with ultra-wealthy investors. Richard reveals how he went from cold-calling wealth advisors to becoming the go-to expert for $100M+ families. He dives deep into what family offices really look for in founder-led businesses, why your one-liner pitch matters more than your 40-page deck, and how creative deal structures (like gross revenue royalties and capped equity warrants) can make or break a transaction. Whether you're scaling to sell or preparing to raise capital, you’ll learn: Why trust trumps returns in family office investing How to avoid the #1 mistake founders make when pitching Why timing your exit is equal parts gut feel and market signals The tools Richard built to help CEOs find the right investors and pitch smarter And the one piece of advice he’d give his younger self after 18 years in the industry If you’re an operator, founder, or investor looking to understand the real game behind exits and capital strategy, this episode is a masterclass in long-term thinking and investor psychology. -- Richard C. Wilson is a husband, adventure enthusiast, father of 3 girls, and a third generation Eagle Scout. Richard is also the CEO of the #1 ultra-wealthy investor club with 7,500+ investors called Family Office Club which hosts 16 in-person events per year. His investor club runs the most listened to podcast on family offices, the most watched YouTube channel with 1,000+ videos, and has spent $25M the last 18 years hosting 300+ live events and he has a total of 17 million social media group members and followers. Richard also runs and owns Billionaires.com where he is interviewing 100 billionaires publicly to create the #1 resource on their scaling strategies and mindset. Richard on LinkedIn: https://www.linkedin.com/in/singlefamilyoffice/ Website: https://familyoffices.com/ -- The Exit—Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You’ll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on flippa.com/the-exit-podcast/…

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From $0 to Multiple Exits: How Jeet Banerjee Turned Teenage Hustle into Million-Dollar Exits 29:40

11 weeks ago29:40

29:40

Want a quick estimate of how much your business is worth? With our free valuation calculator, answer a few questions about your business and you’ll get an immediate estimate of the value of your business. You might be surprised by how much you can get for it: https://flippa.com/exit -- In this episode of The Exit: At just 17, Jeet Banerjee knew the 9-to-5 life wasn’t for him. In this candid and inspiring episode, Jeet joins Steve McGarry to break down his journey from teenage odd jobs to becoming a serial entrepreneur with multiple successful exits. He shares how he turned a basic web design hobby into a digital marketing agency, then parlayed that into a college admissions platform that reached 500,000+ users and was ultimately acquired for its rich dataset. Jeet dives deep into: Why documentation and SOPs are essential—even if you’re not planning to sell (yet) How reaching out proactively (instead of waiting) helped him close an acquisition The untapped goldmine of customer data in eCommerce—and how he used it to scale a home décor DTC brand Why direct mail still works in the digital age His mindset on negotiation, knowing your walk-away number, and failing forward Plus, he closes with the advice he’d give his younger self—and anyone starting out: “Failure is just an event. It only defines you if you let it.” -- Jeet Banerjee is a serial entrepreneur and digital marketing expert who has led multiple acquisitions in the tech and e-commerce spaces. Jeet is a TEDx speaker, has been featured in several major publications, and is an advisor/consultant to many well renowned companies. Jeet is extremely passionate about using his digital marketing expertise to help other brands and businesses find more of their target customers! Jeet on LinkedIn: https://www.linkedin.com/in/jebanerjee/ Instagram: https://www.instagram.com/thejeetbanerjee/ -- The Exit—Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You’ll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on flippa.com/the-exit-podcast/…

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Hard Truths, Growth Stories, and Bulletproofing Your Business for Sale with Heather Schuck 29:28

12 weeks ago29:28

29:28

Want a quick estimate of how much your business is worth? With our free valuation calculator, answer a few questions about your business and you’ll get an immediate estimate of the value of your business. You might be surprised by how much you can get for it: https://flippa.com/exit -- In this episode of The Exit: Heather Schuck shares her journey from neuropsychology to baby fashion mogul to co-founding Elevated Exit, where she helps founders build sellable businesses. Drawing from her own burnout-driven exit, she reveals hard truths about SOPs, real business assets, and the power of a compelling growth story. She discusses timing, AI integration, and why many founders regret PE earn-outs. Whether you're planning years ahead or already itching to move on, Heather’s straight-talking advice offers a smart, strategic lens on what it really takes to exit well—and why you should start preparing long before you think you're ready. -- Heather Schuck is a dynamic sales and marketing strategist with over 20 years of experience helping businesses optimize their internal sales and marketing systems to increase their valuation and position them for successful exits at higher multiples. She works closely with CEOs and founders to refine their go-to-market strategies and create a robust, data-driven sales pipeline to support near-term growth projections, positively impacting investor confidence. With over $300 million in attributed revenue, Heather has a keen ability for identifying new growth opportunities, deep insight into customer behaviors, and a proven track record of aligning marketing with sales to close high-ticket deals faster. Her ability to create actionable growth plans and implement efficient, lean operations to maximize revenue without overspending on customer acquisition or retention makes her an invaluable asset for companies looking to boost their valuation before an exit. Heather on LinkedIn: https://www.linkedin.com/in/heatherlschuck/ Website: https://elevatedexitpartners.com/ -- The Exit—Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You’ll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on flippa.com/the-exit-podcast/…

1
One Patent Away: How Smart IP Strategy Can 10x Your Exit Valuation with Craige Thompson 30:27

13 weeks ago30:27

30:27

Want a quick estimate of how much your business is worth? With our free valuation calculator, answer a few questions about your business and you’ll get an immediate estimate of the value of your business. You might be surprised by how much you can get for it: https://flippa.com/exit -- In this episode of The Exit: In this tactical and deeply personal episode, patent attorney and engineer Craige Thompson shares how a devastating loss in his family sparked a lifelong mission to help entrepreneurs protect—and profit from—their innovations. From protecting EBITDA during an exit to engineering “commercially valuable choke points,” Craige reveals how patents can give you a monopoly-like edge and even solve for all five of Porter’s Five Forces. You'll learn when not to file a patent, how to evaluate whether your idea is truly novel, and why licensing your IP with “field of use” carve-outs can lead to surprising monetization wins. Whether you're startup-curious or exit-ready, this episode is packed with frameworks, red flags, and real-world examples to rethink IP as a strategic weapon, not just legal paperwork. -- Craige grew up in his father’s entrepreneurial small business in Fond du Lac, WI, where he learned the importance of protecting small businesses and helping them thrive. At Thompson Patent Law, Craige built a firm that focuses on creating Litigation Quality Patents® services—intellectual property assets designed to drive measurable business value. Their team ensures clients avoid unnecessary costs by focusing only on patents with real strategic potential. Through his Amazon #1 best-seller Patent Offense and the Litigation Quality Patent Podcast, Craige shares strategies to maximize IP value. Craige on LinkedIn: https://www.linkedin.com/in/craigeothompson/ Website: https://thompsonpatentlaw.com/ -- The Exit—Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You’ll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on flippa.com/the-exit-podcast/…

1
Exiting in Silicon Valley: Derek Collison on Cloud Wars, Kubernetes, and Synadia 37:11

14 weeks ago37:11

37:11

Want a quick estimate of how much your business is worth? With our free valuation calculator, answer a few questions about your business and you’ll get an immediate estimate of the value of your business. You might be surprised by how much you can get for it: https://flippa.com/exit -- In this episode of The Exit: Derek Collison, founder and CEO of Synadia and previously Apcera and creator of Cloud Foundry, explores his storied career in tech, entrepreneurship, and building platforms that shaped modern cloud computing. From starting with a Commodore 64 at age 12 to working at Google, VMware, and founding Apcera—Derek shares how he turned distributed systems challenges into billion-dollar ideas. He unpacks the high-speed growth, fundraising challenges, and exit to Ericsson, before launching his latest venture, Synadia, built on the NATS open-source tech now downloaded over 300 million times. Derek opens up about: Getting into tech as a teenager in the 1980s Building Cloud Foundry at VMware after a call from Paul Maritz Starting Apcera and scaling to 150 employees in 12 months Navigating an acquisition by Ericsson amidst Kubernetes disruption How to survive the VC game: from seed to Series B His playbook for product-led platform companies and why most fail The emotional toll, decision-making pressure, and rewards of being a founder Why introverts need to lean in and chase serendipity How Synadia is powering AI at the edge, connected cars, and Industry 4.0 "Be humble, lean in, and don’t delay hard decisions" — Derek’s advice rings true for every founder navigating the speed and pressure of today’s tech ecosystem -- Derek Collison is a 30 year industry veteran, entrepreneur, and pioneer in secure and large-scale distributed systems and cloud computing. He helped change the way financial, transportation, and logistics systems fundamentally worked while spending over a decade at TIBCO, designing systems that still power much of those industries today. During his time at VMWare, Derek designed and architected CloudFoundry, the first open-source enterprise PaaS. He then founded Apcera, a company designed to drive security and policy into easy to use platform technologies. After the successful sale of Apcera to Ericsson, Derek took the messaging technology he designed to power the CloudFoundry and Apcera systems, NATS.io, and created Synadia. Synadia is pioneering secure and global messaging as a digital utility to help drive security and powerful communication and collaboration into IoT, edge, and cloud computing systems. Derek on LinkedIn: https://www.linkedin.com/in/derekcollison/ Website: https://www.synadia.com/ -- The Exit—Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You’ll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on flippa.com/the-exit-podcast/…

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The Exit - Presented By Flippa « »
Exiting in Silicon Valley: Derek Collison on Cloud Wars, Kubernetes, and Synadia