Made It with Connor Tomkies

Connor Tomkies
  • 4.8 (24)
  • ENTREPRENEURSHIP
  • UPDATED WEEKLY

"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, practical advice, and insider tips on entrepreneurship, business growth, and personal development.

  1. MAY 26

    American-Made Watchmaker takes on Billion-Dollar Goliath with RT Custer & Vortic Watches

    https://www.pvig.com/madeithttps://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 Kickstarter to a federal courtroom battle with the Swatch Group, what it took to buy out his co-founder after 10 years, and why scaling American manufacturing might just be the next moonshot. A deep, candid look at craft, conflict, and creating legacy through time. Check Out Our SponsorsPine View Insurance Group - https://www.pvig.com/madeitByldd - https://byldd.com/ Chapters [00:00:00] Starting in the Memory Business [00:01:00] Why Vortic Turns Pocket Watches [00:02:00] Kickstarter Launch and Early Proof [00:03:30] The Watch-a-Day Marketing Model [00:04:30] Pivoting During the Pandemic [00:06:00] The Story in Every Watch [00:06:45] Buying Out His Co-Founder [00:09:00] Running the Company Solo [00:11:00] Where the Business Stands Now [00:12:45] Colorado Watch Co. Vision [00:14:30] Growth vs Lifestyle Business [00:15:30] Manufacturing Challenges at Scale [00:17:00] Distribution Strategy and Retail Plans [00:18:00] Raising Capital for Expansion [00:19:00] Sued by Swatch Group [00:21:00] Fighting a Trademark Lawsuit [00:23:45] Nearly Going Bankrupt [00:25:00] Winning in Federal Court [00:27:00] Legal Precedent and Impact [00:29:00] Making Watches 85% American [00:30:30] The Real Challenge: Skilled Labor [00:32:45] Is 100% Made in USA Possible? [00:34:00] Lessons from Watchmaking History [00:35:45] The Opportunity in Trades [00:37:00] The Moat Around Watchmaking [00:38:15] Watches as Heirlooms and Art [00:39:15] The Future of American Watchmaking [00:40:00] Where to Find RT and His Brands RT's Stuff: Website: https://vorticwatches.com/Colorado Watch Co: https://coloradowatchcompany.com/X: https://x.com/RT_CusterLinkedIn: https://www.linkedin.com/in/alex-lieberman/ My Stuff: Podcast: https://www.madeitpod.com/Website: https://www.connortomkies.com/X: https://twitter.com/ConnorTomkiesLinkedIn: https://www.linkedin.com/in/connortomkies/

    42 min

  2. MAY 12

    How “Boring” Businesses Make Big Money with Nick Huber (& Alex Lieberman)

    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-storage to buying a $50M company, Nick shares tactical advice, brutal honesty, and hilarious truths about what it really takes to make it. Plus: how Alex is building his own HoldCo, and why AI isn’t eating their businesses just yet. Check Out Our SponsorsPine View Insurance Group - https://www.pvig.com/madeitByldd - https://byldd.com/ Nick's Book!  Chapter Markers: [00:00:00] Introducing Nick Huber & Alex Lieberman [00:01:00] The Sweaty Startup Philosophy [00:02:30] Building Skills Before Innovation [00:03:30] Sales as a Foundational Skill [00:05:00] Knowing When to Quit [00:06:30] Urgency and Speed in Business [00:08:00] The Power of Momentum [00:09:00] Redefining Success and Leverage [00:10:30] Life After $20K a Month [00:12:00] Embracing the Hedonic Treadmill [00:13:00] Huber's Business Timeline [00:15:00] Raising Capital and Scaling Up [00:16:30] Lessons From Starting Ten Companies [00:17:30] Avoiding Bottlenecks as a Founder [00:18:30] Holding Companies vs. Private Equity [00:20:00] Ownership Philosophy and Exit Strategy [00:21:00] Optimizing for Joy or Growth [00:22:30] Buying Businesses and Taking Swings [00:24:00] Challenges and Wins With Somewhere.com [00:25:30] Offshoring Strategy and Market Dynamics [00:27:00] Global Hiring Trends and Niches [00:29:00] AI, Automation, and Agency Moats [00:31:00] The Value of Cold Emails [00:32:00] Leveraging AI for Lead Gen [00:34:00] Building Distro as a Product Funnel [00:35:30] Why AI Tools Are Just Getting Started [00:37:00] Hunting for Business Ideas [00:39:00] Filtering Good vs. Bad Ideas [00:41:00] Dangerous and Unsustainable Businesses [00:42:00] Nick’s Next Chapter in Entrepreneurship [00:43:30] Final Thoughts From the Group Nick's Stuff: Website: https://sweatystartup.com/X: https://x.com/sweatystartupPodcasts: https://sweatystartup.com/podcast/Youtube: https://www.youtube.com/channel/UCBYwRdRw6x9bH4PsyCLnmOw Alex's Stuff: Website: https://foundersjournalpod.morningbrew.com/X: https://x.com/businessbaristaLinkedIn: https://www.linkedin.com/in/alex-lieberman/ My Stuff: Podcast: https://www.madeitpod.com/Website: https://www.connortomkies.com/X: https://twitter.com/ConnorTomkiesLinkedIn: https://www.linkedin.com/in/connortomkies/

    48 min

  3. APR 28

    Scaling Startups to Zebras, Unicorns & Decacorns with Barry Stamos

    https://www.pvig.com/madeithttps://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 exited founders backing groundbreaking startups. We explore his investments in companies like Colossal Biosciences, Apollo Neuro, and Brain Ritual, discuss the role of purpose-driven businesses, and dive into the unexpected impact of Ayahuasca on his personal and professional life. Plus, a surprise moment during the interview makes this episode one for the books. Check Out Our SponsorsPine View Insurance GroupByldd Chapters: [00:00:00] Welcome Barry Stamos[00:00:30] Leaving Corporate to Build Startups[00:02:00] The Matrix and a Life Pivot[00:04:00] Early Startup Struggles[00:05:30] Building a Billion-Dollar Exit[00:06:45] Burnout and the Founder Mindset[00:08:30] Investing Instead of Operating[00:10:15] Supernova’s Founder-Led Investments[00:12:45] What Makes Startups Thrive?[00:14:15] Founders Helping Founders[00:15:45] Tuff & Needle vs. Casper[00:17:30] Colossal’s Mission to End Extinction[00:19:15] The Power of Moonshot Ideas[00:22:00] The Future of Biotechnology[00:24:00] Apollo Neuro and the Science of Vibration[00:27:00] Using Tech to Solve Human Problems[00:28:45] Brain Ritual: Tackling Migraines[00:30:00] Balancing Freedom and Purpose[00:32:30] The Infinite Search for Fulfillment[00:35:00] First Ayahuasca Experience[00:37:00] A Life-Changing Surprise Announcement[00:39:45] The Power of Collaboration[00:41:00] Where to Find Barry Stamos Barry's Stuff: Barry's Speaker Website: https://barrystamos.com/Supernova: https://1supernova.com/LinkedIn: https://www.linkedin.com/in/bstamos/ My Stuff: Podcast: https://www.madeitpod.com/Website: https://www.connortomkies.com/X: https://twitter.com/ConnorTomkiesLinkedIn: https://www.linkedin.com/in/connortomkies/

    44 min

  4. APR 14

    He Built 52 Hotels and Advised AirBnb with Chip Conley

    https://www.pvig.com/madeithttps://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 shaped his career and personal transformation. He opens up about near-death experiences, midlife awakenings, and the powerful wisdom that comes from reinvention. Whether you're a post-exit founder or just contemplating your next chapter, this conversation is packed with insight, honesty, and heart. Check Out Our SponsorsPine View Insurance GroupByldd Chapters:[00:00:00] Who is Chip Conley? [00:01:45] Building Boutique Hotel Empire [00:03:29] Near-Death Experience Changes Everything [00:06:31] Struggles After Selling the Business [00:08:19] Joining Airbnb as Modern Elder [00:10:56] Wisdom Beats Knowledge Today [00:11:51] Founding Modern Elder Academy [00:13:32] Creating Space for Serendipity [00:15:02] Simplifying Airbnb’s Strategy [00:16:57] Regulation as Competitive Advantage [00:18:28] Thinking in Decades, Not Months [00:19:54] Rebuilding Identity After Exit [00:21:11] Exercising Curiosity at Work [00:23:37] Managing Visionary Co-Leaders [00:24:55] Buying First Hotel at 26 [00:28:00] Attracting Rock Bands with Massages [00:30:43] Why Peripheral Players Matter [00:31:45] Leading with Emotional Intelligence [00:33:00] Learning to Love Midlife [00:34:30] Men and Loneliness in Midlife [00:36:54] Building Real Wisdom Practices [00:39:00] Team-Wide Wisdom Reflections [00:40:30] Aging as a Growth Opportunity [00:43:00] What is MEA Really Like? [00:44:45] MEA’s Growing Global Community [00:46:29] Reframing Aging and Transition [00:47:45] Becoming a Dad at 64 [00:48:38] Where to Find Chip Online Chip's Stuff: Chip's Website: https://chipconley.com/MEA: https://www.meawisdom.com/LinkedIn: https://www.linkedin.com/in/chipconleysf/ My Stuff: Podcast: https://www.madeitpod.com/Website: https://www.connortomkies.com/X: https://twitter.com/ConnorTomkiesLinkedIn: https://www.linkedin.com/in/connortomkies/

    50 min

  5. MAR 31

    From Dot-Com to Giant Exits with Author and Entrepreneur Lewis Schiff

    https://www.pvig.com/madeithttps://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 industries, and reveals insights on building wealth through founder-friendly capital and innovative business models. He also discusses his Birthing Giants Fellowship and highlights unique opportunities like Aegis Response, offering practical advice and inspiration for entrepreneurs at every stage. Check Out Our SponsorsPine View Insurance GroupByldd Chapters [00:00:00] Intro: Lewis Schiff Background[00:01:00] Entrepreneurial Origin Story[00:02:00] Dot Com Wealth Creation[00:03:00] Early Exit and Real Estate[00:05:00] Angel Investing & Scale Strategy[00:07:00] Tech Drives Business Change[00:09:00] Writing for Wealth Creation[00:14:00] Dry Powder & Capital Trends[00:20:00] Founder Friendly Capital Terms[00:26:00] Birthing Giants Fellowship Insights[00:31:00] Aegis Response Origin Story[00:37:00] Wrap Up & Connect Lewis' Stuff: Birthing of Giants: https://birthingofgiants.com/LinkedIn: https://www.linkedin.com/in/lewisschiff/ My Stuff: Podcast: https://www.madeitpod.com/Website: https://www.connortomkies.com/X: https://twitter.com/ConnorTomkiesLinkedIn: https://www.linkedin.com/in/connortomkies/

    39 min

  6. MAR 17

    Failing Fast, Winning Big, and Giant Fire Blankets with Mike Lloyd

    https://www.pvig.com/madeithttps://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. He also discusses his latest ventures, including a high-net-worth insurance agency and an innovative wildfire protection company. If you're interested in startups, insurance, or what it takes to scale and sell a company, this episode is packed with valuable insights. Check Out Our SponsorsPine View Insurance GroupByldd Chapters: [00:00:00] Welcome to Made It with Connor[00:00:15] Mike Lloyd’s entrepreneurial journey begins[00:01:30] From MIT to startups and HBS[00:02:45] What business school really teaches[00:05:00] Learning entrepreneurship on the job[00:06:45] The art of networking and relationships[00:09:00] First startup failure and key lessons[00:12:30] The challenge of selling insurance[00:15:00] Founding Corvus: A better approach[00:18:30] Why cyber insurance was the right bet[00:22:00] How AI is changing the insurance game[00:25:00] Scaling Corvus and early traction[00:29:00] The business of insurance underwriting[00:31:00] Selling Corvus to Travelers[00:34:00] What comes after a big exit?[00:36:00] Why smart people get insurance wrong[00:39:00] High-touch insurance for high-net-worth clients[00:42:00] Buying a wildfire protection company[00:45:00] The future of insurance and innovation[00:46:45] Building a network through business[00:47:00] Wrap-up and where to connect Mike's Stuff: Pine View Insurance: https://www.pvig.com/madeitLinkedIn: https://www.linkedin.com/in/mikelloyddotme/ My Stuff: Podcast: https://www.madeitpod.com/Website: https://www.connortomkies.com/X: https://twitter.com/ConnorTomkiesLinkedIn: https://www.linkedin.com/in/connortomkies/

    48 min

  7. MAR 3

    From College Dorm to Wall Street IPO with Purpose Built's Miles Lasater

    https://www.pvig.com/madeithttps://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 of breaking into difficult markets like higher education and government. He also discusses his venture studio, Purpose Built, and the innovative startups he's helping to launch. Check Out Our SponsorsPine View Insurance GroupByldd Chapters: [00:00:00] Welcome Miles Lasater [00:00:30] Founding Higher One in College [00:01:15] The Advantage of Naivete [00:02:00] Painting Through Uncertainty [00:02:30] Scaling to 1,000 Campuses [00:03:00] Hiring a CEO as Founders [00:04:00] Picking the Right Leader [00:05:00] Role Evolution and Growth [00:06:30] IPO and Scaling Challenges [00:07:15] Revenue Model and Growth [00:08:30] Navigating Financial Regulations [00:09:45] Learning Banking from Scratch [00:10:30] Thinking Beyond Industry Norms [00:12:00] Founder-Friendly Stock Options [00:12:45] Transitioning Out of HireOne [00:14:15] The Itch to Start Again [00:15:00] Seeclickfix and Civic Tech [00:16:30] Selling to Universities and Cities [00:18:30] Building Trust in Government [00:19:15] Launching Purpose Built [00:20:30] Coral Care and Healthcare Startups [00:22:00] Twill: Referral-Based Hiring [00:24:15] Dunbar and Relationship Mapping [00:25:45] AI’s Impact on Networking [00:26:45] Banning Cell Phones in Schools [00:28:30] Supply-Side Liberalism Explained [00:30:00] What Excites Miles in 2025 [00:30:30] Where to Find Miles Miles' Stuff: Purpose Built: https://www.purposebuilt.vc/LinkedIn: https://www.linkedin.com/in/mileslasater/ My Stuff: Podcast: https://www.madeitpod.com/Website: https://www.connortomkies.com/X: https://twitter.com/ConnorTomkiesLinkedIn: https://www.linkedin.com/in/connortomkies/

    32 min

  8. FEB 17

    The Warren Buffett of Lifestyle Investing with Justin Donald

    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 into identifying emerging trends, the importance of tax strategies, and the evolution of investment opportunities—from private credit to blockchain and AI-enabled tech. Whether you're an aspiring entrepreneur, an investor, or someone planning a business exit, this conversation is packed with valuable takeaways. LifestyleInvestor.com/consultation Episode Chapters: [00:00:00] Welcome to Made It [00:00:30] Moving to a new entrepreneur hub [00:01:15] Doing business with people you like [00:01:45] First taste of an exit [00:02:15] Investing in a dog training business [00:03:30] Scaling and selling the company [00:04:15] Building The Lifestyle Investor [00:05:00] Exclusive mastermind community [00:06:15] Investing principles for young entrepreneurs [00:07:15] Buying businesses vs. investing [00:08:30] Private credit and deal flow [00:09:15] Preparing for a successful business exit [00:10:00] Trends shaping 2025 investing [00:11:30] Spotting opportunities before they go mainstream [00:13:00] Industrial, port cities, and reshoring [00:14:45] AI-enabled tech and Web3 gaming [00:16:00] Investing in pro sports teams [00:17:45] GP stakes and distressed assets [00:19:00] Robotics, SaaS, and AI growth [00:21:00] Operating in an AI-driven world [00:22:30] The philosophy behind The Lifestyle Investor [00:24:00] How the mastermind community started [00:26:30] Pricing a high-value community [00:28:15] The true value of tax strategies [00:30:15] Advice for post-exit founders [00:32:00] Why most entrepreneurs aren't great investors [00:33:30] IRS incentives and tax planning [00:34:45] Where to find Justin Donald Justin's Stuff: The Lifestyle Investor: https://lifestyleinvestor.com/LinkedIn: https://www.linkedin.com/in/justinwdonald/X: https://x.com/jwdonald1 My Stuff: Podcast: https://www.madeitpod.com/Website: https://www.connortomkies.com/X: https://twitter.com/ConnorTomkiesLinkedIn: https://www.linkedin.com/in/connortomkies/

    36 min
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4.8
out of 5
24 Ratings

About

"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, practical advice, and insider tips on entrepreneurship, business growth, and personal development.

Information

  • Creator
    Connor Tomkies
  • Years Active
    2024 - 2025
  • Episodes
    33
  • Rating
    Explicit
  • Copyright
    © 2025 Connor Tomkies
  • Show Website
    Made It with Connor Tomkies