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Connor Tomkies Podcasts

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"Made It" is a podcast hosted by Connor Tomkies that delves into the journeys of successful entrepreneurs who have not only built and exited their companies, but who are writing the next chapter of their journeys. The show focuses on the unique challenges and lessons learned while moving beyond the exit, offering insights and strategies for listeners aiming to grow their own businesses. Through engaging conversations with various guests, the podcast provides a blend of motivational stories, ...
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Exit Paradox

Anastasia Koroleva

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I'm Anastasia Koroleva, a 4x exited founder exploring life after selling a business with some of the most remarkable post-exit entrepreneurs in the world. Together, we rediscover purpose, redefine success, master investing, and build fulfilling lives and families. Having survived a 9-digit exit, I dedicated a decade to researching the deepest challenges faced by entrepreneurs after a business sale. This podcast is the platform to share my and other exited founders' hard-earned wisdom with th ...
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Barak Kaufman, founder of Post‑Exit Founders (PEF), grew a 5,000+ member community in four years by word of mouth. He shares what he’s learned from their stories: what works after an exit and what does not. Barak is now partner at VC firm Vine Ventures in New York City and Tel Aviv. Connect with Barak: Linkedin: https://www.linkedin.com/in/barakk/ …
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Some exits, they just stop us in our tracks. Not because of the money or the business genius, but because of the radical personal transformation that followed. Dan Berger's story is one of those. Seven years ago, he sold social tables for around $100 million million dollars. And like so many of us, the exit cracked something open. The wealth, the t…
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https://www.pvig.com/madeit https://byldd.com/ RT Custer turned a passion for nostalgia into two thriving American watch brands: Vortic Watch Co., which transforms antique pocket watches into wristwatches, and the ambitious Colorado Watch Co., aiming to bring American watchmaking back at scale. In this episode, RT shares how he went from a $40K Kic…
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Entrepreneur and investor Nick Huber joins Connor Tomkies and Alex Lieberman to break down how he built a $100M+ empire starting with sweaty, unsexy businesses like student storage. They discuss his new book The Sweaty Startup, the trap of chasing big ideas too early, and why momentum, urgency, and simplicity often beat innovation. From self-storag…
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Today’s episode is different. My guest isn’t an exited founder but she’s someone we all need. Amy Castoro helps families have honest conversations about wealth—the kind most of us were never taught to have. She shares practical tools from her firm’s 50 years of experience advising some of the wealthiest families in America. Her work focuses on the …
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https://www.pvig.com/madeit https://byldd.com/ We sit down with Barry Stamos, a post-exit founder and investor focused on bold, world-changing companies. Barry shares his journey from corporate consultant to tech founder, detailing his early struggles, successful exits, and how he now supports other entrepreneurs through Supernova, a collective of …
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My friend Jay Radia doesn’t just build businesses—he builds momentum.He’s a three-time tech founder and a prolific angel investor.Since his last exit two years ago, he’s been building Blissgrowth—a venture studio that partners exclusively with exited founders. Why did he choose this path? What has he learnt so far? Was it the right move? For a whil…
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Linda Abraham is one of the most extraordinary women I’ve ever met. She’s in a class of her own.She’s been navigating the post-exit world for 28 years, ever since her first exit.And what an exit it was: a 5X return to investors in just two years!She went on to lead her second company, comScore, from founding to IPO—building it into a global powerho…
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https://www.pvig.com/madeit https://byldd.com/ In this episode Connor sits down with hospitality legend and Modern Elder Academy founder, Chip Conley. From building Joie de Vivre into one of the largest boutique hotel brands in the U.S., to mentoring the Airbnb founders through their explosive growth, Chip shares the behind-the-scenes stories that …
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https://www.pvig.com/madeit https://byldd.com/ In this episode guest Lewis Schiff—a seasoned entrepreneur, author, and former dot-com founder—shares his journey from early entrepreneurial days to successful exits and strategic angel investing. Lewis dives into his experiences in the dot-com era, explains how technology is transforming traditional i…
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My guest today is Adam Rossi. He sold his company, Platinum Solutions, 14 years ago and walked away with life changing wealth. But what hit him first after his exit was regret. We talk about how he came to terms with his new reality, searched for his new purpose, and dealt with losing his found identity. My favorite part of Adam's story is that he …
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Mike Brown's post-exit journey led him from chaos to clarity, but not right away. He had to go through a painful divorce, a business failure, financial losses and emotional turmoil. Today we are talking about what he's learned and why he decided to dedicate himself to coaching. 🔗 CONNECT WITH MIKE: 🎥 YouTube Channel - @mbrown_co 🐦 X (Twitter) - htt…
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https://www.pvig.com/madeit https://byldd.com/ We sit down with Mike Lloyd, a seasoned entrepreneur who built and exited Corvus, a cyber insurance company, for nine figures. Mike shares his journey from Virginia Military Institute to MIT and Harvard, diving into the lessons learned from his first failed startup and how he pivoted to massive success…
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VCs notoriously avoid investing in married couples, fearing that personal conflicts could sink the business. Yet, the Lazerows defied that norm—building not just one, but two successful companies together, culminating in an $800M exit. They didn’t just make it work; they mastered it—and then wrote a book about it. Today, we’ll dive deep into what e…
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https://www.pvig.com/madeit https://byldd.com/ Episode Description: Connor sits down with Miles Lasater, founder of Purpose Built and co-founder of multiple successful companies, including HireOne, which went public in 2010. Miles shares insights on scaling a business from college startup to IPO, hiring a CEO as a young founder, and the challenges …
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My guest today, Josh Payne, has developed fascinating insights and systems to do just that. Josh sold his company, Stack Commerce, for nearly $100 million 4 years ago. A huge milestone - but as all exited founders know, the real story starts after the deal is done.Today, he’s building again - but with a completely different approach. Josh isn’t opt…
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What would you do if you sold your company for 300 million dollars? Retire? Explore the world? Do all these other things you had no time to do while building a business? This is not what my friend Alex Macdonald did when he sold his company Velocity Black two years ago. In fact, Alex made it quite impossible for himself to have any kind of post-exi…
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In this episode of Made It with Connor Tomkies, Justin Donald, the "Warren Buffett of Lifestyle Investing," shares insights into his journey as a post-exit entrepreneur, investor, and community builder. He discusses his early business exits, the power of strategic investing, and the philosophy behind The Lifestyle Investor. Connor and Justin dive i…
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My guest today is Cory Janssen, co-founder of Investopedia. Cory sold the business 17 years ago, but what came next was far from the smooth ride he or anyone might have expected. He spent years in painful trial and error, half-heartedly starting new ventures while avoiding real work, experimenting with professional investing and retirement. None of…
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This interview is a special one for me. Michael Miller has been a friend for over 15 years and has made a huge difference in my life. He's a Vedic meditation teacher who taught me to meditate at a time when I was searching for clarity and tranquility following a life-changing exit. Since then, meditation has been my go-to tool for healing, finding …
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My dear friend Sarah Douglass sold her incredibly successful e-commerce business three years ago, achieving the financial freedom she had always dreamed of. But soon after, she found herself grappling with a new challenge: balancing her newfound success with an ever-deepening desire for contentment and a powerful drive to create impact. In today’s …
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Tim Schumacher is the exited founder and former CEO of Sedo, one of the world's largest domain marketplaces, which he led for over a decade before stepping down 13 years ago. What sets Tim apart is how he mastered the elusive work -life balance while still building his company, something most entrepreneurs only dream of. This balance helped him avo…
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Rick Eigenbrod is a deeply respected thinker in the post-exit world. A clinical psychologist and co-author of the classic Yale paper What’s Next: The Entrepreneur’s Epilogue, he’s spent years guiding founders through life after the exit as an executive coach. In this conversation, we get into why Rick believes a “death of who we used to be” and a s…
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Roy Rubin the visionary founder of Magento, built the open source e-commerce platform from the ground up, leading it to a remarkable exit to eBay in just four years. He then stayed on at eBay for two years, but felt suffocated by corporate walls. That's when it hit him. He barely knew his family anymore. So he and his wife pulled their kids out of …
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Ten years ago, Brock Weatherup sold his first company, Pet360.com, to PetSmart for $160 million. It took under five years to build. Since then, he’s had two more successful exits, but two years ago, his journey took an unexpected turn when a life-changing medical diagnosis reshaped his entire outlook. In this episode, Brock talks about the secrets …
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In this episode of Made It with Connor Tomkies, Connor sits down with Barak Kaufman, founder of Post Exit Founders, to discuss life after exiting a company and the next steps for founders. They explore the three types of post-exit founders, dive into Barak's investment in a soccer team rivaling Ryan Reynolds' Wrexham, and talk about the challenges …
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Three years ago, Scott Wolfe sold his company, Levelset, for half a billion dollars. Excited and relieved at first, he soon found himself deeply frustrated with the reality that his vision for the business would now never be realized. Scott is a natural creative who sees building a business as an artistic endeavor. It was this intrinsic need to cre…
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My friend Jonathan has chosen to remain anonymous in exchange for stepping outside his comfort zone — and that he did! Eight years ago, he began a gradual exit from his incredibly successful, bootstrapped company. This strategic approach had an unexpected benefit: it smoothed his post-exit transition, making it more manageable both emotionally and …
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In this episode of Made It with Connor Tomkies, we dive into a groundbreaking concept with Charlie Olson, CEO of Pando. Charlie explains how his company helps individuals in high-risk careers like professional athletes and entrepreneurs pool their incomes, creating a supportive and incentivized community that shares both successes and setbacks. Lea…
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In this episode of "Made It with Connor Tomkies," Nick Telson-Sillett shares his journey from founding "Design My Night" to exiting for over £35 million. Nick talks about the challenges of scaling a company in a competitive market, the importance of financial freedom, and how to navigate earn-outs. He also discusses his ventures in angel investing …
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In this episode of Made It with Connor Tomkies, entrepreneur Praveen Ghanta shares the unconventional story behind his bootstrapped exit, including a nine-figure success with Hidden Levers. Praveen dives into his philosophy on bootstrapping versus raising capital, the power of fractional work, and what he’s focusing on now with his new ventures. Tu…
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In this episode of Made It with Connor Tomkies, Gil Eyal returns to discuss the unpredictable nature of success in the world of social media and business investment. They dive deep into the challenges of investing in consumer products, the importance of identifying businesses with billion-dollar potential, and the pitfalls of the dating app industr…
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Jason Kirby. He Sold Liquid Sky software to Walmart six years ago, but became disillusioned when Walmart abruptly scrapped the company's ambitious plans. Seeking a new direction, Jason joined Generation Esports, rapidly scaled it and exited three years ago. This last exit prompted Jason to reassess his priorities, leading him to focus on family, he…
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Matthew Johnson sold his healthcare software company 11 years ago, after leading it through three rounds of fundraising in just three years. Alongside his twin brother Nathan, he then acquired and transformed TruConnect into a telecom powerhouse. Matthew also co-founded the technology investment bank Drake Star Partners, leveraging his earlier inve…
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Join Connor Tomkies in this exciting episode of the Made It Podcast as he chats with Darrell Lerner, the man behind All Paws and Snap Interactive. Discover how Darrell transitioned from revolutionizing online dating to creating a successful platform connecting dogs with their forever homes. Listen as Darrell shares the unconventional journey of fou…
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Bill Flagg spent 20 years building 5 incredibly successful tech businesses, then unexpectedly sold them all. To his own surprise, the thrill of building businesses faded, and he found himself craving a pause, a chance to become a beginner again and enjoy the simple things in life. Two years ago, Bill moved with his family from Colorado to Portugal …
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Tony Kula. He has built three businesses, exiting his first in his mid 20-s and spending two decades turning the next into a video distribution powerhouse, which he sold six years ago. His latest venture, MeetYoo, skyrocketed during the pandemic, but faced serious challenges afterward, prompting Tony to reassess his priorities. Now he's an advocate…
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Join us for a captivating conversation with Benji Markoff, a returning guest who initially appeared in Episode 3. In this episode, Benji opens up about his latest venture, Padel United Sports Club. He discusses the intricacies of launching a high-end social wellness club focused on the fast-growing sport of Padel. Discover how Benji is building a v…
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Shane Neman successfully built and exited two iconic businesses: JoonBug, a digital events powerhouse, and EZ Texting, the largest business SMS software platform in the US. Today, he manages a substantial real estate portfolio, invested in over 50 startups, and authored the book called Nightlife Lessons: How I Conquered the Business of Partying wit…
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Ben White. He's sold three businesses so far for $80M, $88M and $800M. It was the last exit 16 years ago that hit him hard. What followed was a dark decade filled with divorce, addiction and significant financial losses. However, today Ben is the happiest he's ever been. In this episode we discuss his hard-earned lessons on happiness, why he starte…
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In this episode we sit down with Alexander White, the co-founder of Next Big Sound. Alexander shares his journey from launching a music data business during his senior year at Northwestern to its acquisition by Pandora for a remarkable 10x revenue multiple. Discover how Alexander's passion for data led him to his next venture, focusing on uncoverin…
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Alex Bean has recently sold his fintech company Divvi for $2.5 billion. Today, he runs a VC firm called Tandem and has written a book titled The Factory for Good on turning your life into a force for positive impact. In this episode, we explore the emotional complexities of wealth and discuss why he envies those still in the rat race, how he earns …
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CK Kim is a serial tech entrepreneur who recently completed his second exit, exceeding $510M. To recover, CK took a year -long sabbatical. During his travels, he reflected on his experiences and distilled his insights into clear and powerful ideas. In this episode, we discussed the importance of soul search, secrets to post -exit happiness, the imp…
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In this episode of "Made It with Connor Tomkies," Connor sits down with Vadim Rogovskiy, a successful entrepreneur who sold his first company in 2014 and has since been involved in various ventures, including the innovative AR company 3DLOOK. Vadim shares his journey from early entrepreneurial efforts in Ukraine, dealing with the challenges of in-g…
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Boris shares his journey from working at Atlassian to founding his own company Atlas Authority, navigating the challenges of being a solo founder, and eventually exiting the business. Dive into their discussion about unsexy business ideas, the importance of shared context in startups, and Boris's candid insights on his entrepreneurial experiences. …
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Eric Bahn, co-founder of Hustle Fund, discusses his journey as an entrepreneur and investor. He shares insights on building genuine communities, identifying true "hustlers", and redefining wealth and success. Eric opens up about his family's story, working with his wife and sister, and the importance of vulnerability in leadership. He also discusse…
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Andrew Warner, founder of Mixergy, returns to the pod to share his insights on the post-exit journey of entrepreneurs. The two discuss the importance of finding meaning and purpose after selling a business, the value of shadowing successful entrepreneurs, and the potential of building a community for post-exit founders. With a focus on personal gro…
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Preston Rutherford. His company was sold in a 9-figure exit 5 years ago. A couple of years later, the combined company had a 10-digit IPO. But Preston wasn't there to experience it. While he regrets exiting too early, he acknowledges that the exit propelled him into an intense personal growth journey. In this episode, Preston shares how he learned …
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In this episode, serial entrepreneur Dan Reich shares his remarkable journey of building and exiting multiple companies across various industries. From his early ventures in high school to co-founding Spinback, which was acquired by Buddy Media and later Salesforce, Dan's experiences highlight valuable lessons in entrepreneurship, partnerships, and…
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Four years ago Gil Eyal sold HYPR - a software business which revolutionized the way big agencies and brands run influencer marketing. Today, Gil runs a venture capital firm which adds value to consumer tech companies by bringing celebrities onboard. In this episode, we discuss overcoming a post-exit identity crisis, building a personal brand, deal…
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