Made It with Connor Tomkies

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 through Horseplay Ventures and his efforts to support the LGBTQ+ founder community. Tune in for insights on business growth, exit strategies, and the evolving startup landscape.Join Our CommunityChapters:[00:00:00] Introduction and Competitors Wise Up[00:00:14] Naming Companies: Trumpet and Design My Night[00:01:21] Nick’s Post-Exit Life and Identity[00:02:06] Transitioning After a Big Exit[00:02:52] Growing Design My Night to £35M[00:04:10] Creating the Market for Bar Reservations[00:05:26] Selling the Vision: Bar to Bar[00:06:34] Selling to The Access Group[00:08:00] Why It Was Time to Sell[00:09:33] Navigating the Earn-Out Period[00:12:19] Structuring the Earn-Out Deal[00:14:24] Managing Post-Acquisition Relationships[00:18:39] Horseplay Ventures: Angel Investing[00:21:14] Supporting LGBTQ+ Founders with Proud Ventures[00:25:36] Launching the Pitch Deck Podcast[00:28:31] VC vs. Bootstrapping Startups[00:31:39] Honest Mobile: Revolutionizing Mobile Contracts[00:33:54] Fanbase: iOS for Sports TeamsNick's Stuff:Proud Ventures: https://www.proud-ventures.com/Trumpet: https://www.sendtrumpet.com/?ref=nicklinkedinHorseplay Ventures: https://horseplay.ventures/LinkedIn: https://www.linkedin.com/in/nicktelson/My Stuff:Podcast: https://www.madeitpod.com/Website: https://www.connortomkies.com/X: https://twitter.com/ConnorTomkiesLinkedIn: https://www.linkedin.com/in/connortomkies/

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. Tune in for an insightful conversation on growing a company with limited resources and timing your exit for maximum gain.Join Our Community: https://incendium.circle.so/join?invitation_token=8f30b22424ad79e1af33a9258ee335ba7af292ba-a92ebcf2-2d4e-404d-a5a3-42d48dde11efChapters:[00:00:00] Bootstrapping and Billion-Dollar Exits[00:00:45] Microsoft: The World’s Largest Bootstrap[00:02:00] Cashflow and Growth Capital Choices[00:03:30] Raising Growth Equity and Use of Proceeds[00:06:00] Hidden Levers: ARR Growth Challenges[00:09:00] Scaling with Enterprise Sales Teams[00:10:45] 16x Revenue and Selling the Business[00:12:45] Successful Exit with a Strong Multiple[00:14:30] Angel Investing: Betting on Founders[00:17:00] Building with Fractional Work[00:21:00] Focusing on U.S. Talent for Tacit Knowledge[00:23:00] Startups Using Fractional Work[00:24:30] Schools Over: Empowering Non-College Pathways[00:27:00] Future of Work: Flexibility and Fractional Roles[00:31:00] Praveen’s Success with Fractional TalentPraveen's Stuff:Fraction Website: https://www.hirefraction.com/School's Over: https://schoolsover.org/LinkedIn: https://www.linkedin.com/in/pghanta/X: https://x.com/truecostMy Stuff:Podcast: https://www.madeitpod.com/Website: https://www.connortomkies.com/X: https://twitter.com/ConnorTomkiesLinkedIn: https://www.linkedin.com/in/connortomkies/

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 industry. With a mix of humor and insight, Gil and Connor explore the highs and lows of entrepreneurial ventures, leaving listeners with valuable lessons and plenty of inspiration.Check Out Our Sponsors:Join Our Community!https://wealthwithrush.com/ChaptersApologies for the confusion. Here are the updated timecode-based chapter titles:[00:00:00] Introduction: Gil Eyal Returns[00:00:29] The Power of Social Media and Influence[00:02:00] Lessons Learned as an Investor[00:03:45] Consumer Goods vs. SaaS Investments[00:06:08] Focusing on Consumer Goods and Tech[00:08:34] The Challenges of Raising a Fund[00:09:40] Dream Product: A Hair Growth Solution[00:11:00] Rethinking the Dating App Model[00:17:15] Considering a Venture Studio[00:19:14] The Problem with “Fake it Till You Make It”[00:22:00] Excitement Around GLP-1 Drugs and the Future[00:23:40] Civilization as a Business Game[00:25:45] Wrapping Up: Where to Find Gil EyalGil's Stuff:Website: https://stardustventures.us/Email: gil@stardustventures.us LinkedIn: https://www.linkedin.com/in/gileyal/ X: https://x.com/gileyal Instagram: https://www.instagram.com/gileyal My Stuff:Podcast: https://www.madeitpod.com/Website: https://www.connortomkies.com/X: https://twitter.com/ConnorTomkiesLinkedIn: https://www.linkedin.com/in/connortomkies/

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 founding Snap Interactive, leveraging Facebook's app platform, and the unexpected challenges of taking a company public. Learn how his passion for pets led to the inception of All Paws and his unique approach to matchmaking for dogs. Darrell also delves into the thrilling rollercoaster of scaling a startup, raising millions, and the intense due diligence of selling a company. This episode is packed with insights on entrepreneurship, the pet industry, and the evolving world of social media influencers. Don't miss out on Darrell's fascinating stories and valuable lessons!Check Out Our Sponsors:Join Our Community!Chapters:[00:00:00] Welcome and Introduction  [00:00:27] Focus on Dogs  [00:00:45] Connecting with Dog Genetics  [00:01:05] Starting All Paws  [00:01:34] Creating a Pet Matchmaking Service  [00:02:22] From Snap Interactive to All Paws  [00:03:00] The Concept of Tinder for Pets  [00:04:02] Leaning into Online Dating Experience  [00:04:45] Filtering for the Perfect Pet  [00:05:24] Early Success of Snap Interactive  [00:06:00] The Premise of Snap Interactive  [00:07:55] Viral Growth on Facebook  [00:09:15] Unexpected Publicity Boost  [00:10:55] Stock Market Surge  [00:12:30] Raising Capital and Scaling  [00:13:57] Challenges of Being Public  [00:15:00] Insider Trading Restrictions  [00:16:00] Navigating Public Perception  [00:17:00] Leaving Snap Interactive  [00:18:17] Due Diligence Challenges  [00:20:33] Transitioning After the Sale  [00:22:11] Taking Time Off  [00:25:15] Adjusting to Life Post-Sale  [00:26:15] Exploring the Influencer Economy  [00:28:15] Monetizing Influence  [00:30:15] Building Brands with Influencers  [00:31:45] Lessons Learned and Next Steps  [00:34:45] Where to Find Darrell Lerner  Darrell's Stuff:Website: https://www.darrelllerner.com/LinkedIn: https://www.linkedin.com/in/darrelllerner/X: https://x.com/DarrellLerner/Instagram: https://www.instagram.com/dlerner2112/My Stuff:Podcast: https://www.madeitpod.com/Website: https://www.connortomkies.com/X: https://twitter.com/ConnorTomkiesLinkedIn: https://www.linkedin.com/in/connortomkies/

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 vibrant community, the strategic decisions behind membership offerings, and his vision for combining sports with wellness modalities like cryotherapy, sauna, and more.Connor and Benji also explore the creator economy, the importance of genuine human interaction in business, and the value of documenting the entrepreneurial journey authentically. Check Out Our Sponsors:https://wealthwithrush.com/Join Our Community!Chapters:[00:00:00] Intro and Banter[00:00:09] Reflecting on Last Episode[00:00:34] Podcast Schvitz Idea[00:00:55] Sauna Experiences[00:01:21] Live vs. Business Content[00:02:07] Unscripted Conversations[00:02:30] Learning from Discussions[00:02:55] Sauna’s Unique Environment[00:02:45] Paddle vs. Padel[00:03:29] Social Media Influence[00:04:47] Padel United Vision[00:05:15] Creating a Wellness Club[00:05:30] Russian Sauna Traditions[00:06:00] Multipurpose Sauna Hats[00:06:45] Business Content Overload[00:07:00] Entrepreneurial Motivation[00:08:01] Beyond Startup Stories[00:08:30] Late-night Entrepreneur Thoughts[00:09:00] Family and Business Balance[00:09:15] Entrepreneurship as a Career Cycle[00:09:30] Building Multiple Companies[00:09:45] Passion vs. Profit[00:10:00] Business Challenges[00:10:26] Personal Business Journey[00:11:00] Real-life Business Insights[00:12:00] High-level Business Decisions[00:12:30] Value of Spontaneous Ideas[00:13:38] Entrepreneurial Resilience[00:13:45] Padel Community Building[00:14:47] Early Membership Offers[00:15:30] Personalized Sales Pitch[00:16:47] Immediate Feedback[00:16:57] Membership Commitment[00:18:47] Friend’s Support[00:19:00] Sales Strategy[00:19:45] Direct Communication[00:20:26] Immediate Action[00:21:00] Engaging Network[00:21:30] Marketing Authenticity[00:22:47] Personal Branding[00:23:30] Real-life NetworkingBenji's Stuff:Padel United Sports Club: https://www.padelunitedsportsclub.com/Padel Mecca on Substack: https://substack.com/@padelmeccaInstagram: @PadelUnitedSCMy Stuff:Podcast: https://www.madeitpod.com/Website: https://www.connortomkies.com/X: https://twitter.com/ConnorTomkiesLinkedIn: https://www.linkedin.com/in/connortomkies/Tune in to "Made It" with Connor Tomkies and be inspired by stories of entrepreneurial success and innovation. Subscribe now and never miss an episode!

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 uncovering and optimizing tax incentives and credits for businesses. Tune in for insights on entrepreneurship, the music industry's data revolution, and the untapped potential of government incentives.Check Out Our Sponsors: https://wealthwithrush.com/Join Our Community!Chapters[00:00:00] Introduction[00:00:16] Starting Next Big Sound in College[00:00:59] Early Investments[00:01:44] Initial Business Model[00:02:16] Understanding Trends and Early Adopters[00:02:30] Tour Managing a Band[00:04:00] Gathering Data and Selling to Music Industry[00:04:53] Scaling the Business[00:06:00] Series A Funding and Music Industry Dynamics[00:06:56] Pandora Acquisition[00:09:00] Integrating with Pandora[00:12:16] Post Exit Identity Crisis[00:14:13] Team Dynamics at Pandora[00:16:00] Leveraging Youth[00:17:30] Post Exit Life[00:18:30] Professor Role at NYU[00:23:15] Investor & Author Roles[00:27:30] Working at Pandora[00:32:00] Taking a Break[00:36:56] Tax Credits and Incentives Implementation[00:39:30] Working with CPA Networks[00:46:00] Engaging with Large Tax Firms[00:50:00] Leveraging Tax Credits[00:56:00] ConclusionAlexander's Stuff:Website: https://alexanderswhite.com/X: https://x.com/mralexwhiteLinkedIn: https://www.linkedin.com/in/alexanderswhite/My Stuff:Podcast: https://www.madeitpod.com/Website: https://www.connortomkies.com/X: https://twitter.com/ConnorTomkiesLinkedIn: https://www.linkedin.com/in/connortomkies/

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-game advertising, to his pivot into augmented reality and computer vision technology. Learn about his insights into the startup ecosystem, the importance of agility and perseverance, and his vision for the future.Check Out Our Sponsors: wealthwithrush.comChapters: 00:00:00 - Introduction00:01:15 - Social Media Advertising in Eastern Europe00:03:45 - Bootstrapping an Ad Network00:10:00 - Challenges in the Eastern European Ad Market00:15:00 - Selling the Company and Moving On00:17:27 - Investing in Startups00:24:15 - Pivot to Augmented Reality00:30:00 - Building 3DLook00:34:45 - Looking to the Future00:37:30 - Closing ThoughtsVadim's StuffWebsite: https://geek.vc/ Vadim's X: https://x.com/vadim_rogovskiyVadim's LinkedIn: https://www.linkedin.com/in/vadim-rogovskiy/My StuffPodcast: www.mysecondmillionpodcast.comWebsite: https://www.connortomkies.com/X: https://twitter.com/ConnorTomkiesLinkedIn: https://www.linkedin.com/in/connortomkies/

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. Whether you're an aspiring entrepreneur or a seasoned business owner, this episode is packed with valuable lessons and unique perspectives.Chapters[00:00:00] Introduction[00:00:30] The Unsexy Business[00:00:45] From Atlassian to Solo Founder[00:02:15] Starting the Company[00:03:28] Business Model and Services[00:04:30] Platform Risk and Emotional Fatigue[00:04:51] Remote Work and Team Structure[00:05:44] In-Person vs. Remote Work[00:06:15] The Importance of Communication[00:08:45] Accountability as a Solo Founder[00:09:00] Birthday Sale Ritual[00:10:04] Learning from the Sale Process[00:11:03] Valuation and Exit[00:12:15] Post-Exit Reflections[00:13:15] Unsexy Business Ideas[00:15:30] Spam Scoring for Outbound Emails[00:18:45] Sexy Goat Bath Product[00:21:00] Meatbags: A Unique Snack Idea[00:23:15] Property Tax Appeal Service[00:25:45] Weird Sports Network[00:28:30] RC Plane Venues[00:31:15] Public Library Publisher[00:36:00] Advocating for Libraries[00:36:38] Closing Thoughts[00:37:00] OutroBoris' StuffWebsite: https://www.nothingeasyaboutthis.comBoris' X: https://x.com/borisberenbergBoris' LinkedIn: https://www.linkedin.com/in/borisberenberg/My StuffPodcast: www.mysecondmillionpodcast.comWebsite: https://www.connortomkies.com/X: https://twitter.com/ConnorTomkiesLinkedIn: https://www.linkedin.com/in/connortomkies/

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 discusses Hustle Fund's unique investment approach and their flagship event Camp Hustle which aims to build meaningful connections. This candid conversation touches on finding joy after an exit, building inclusive entrepreneurial ecosystems, and growing together in the long-term.Chapters: 00:00 - Intro01:35 - Building Genuine Communities03:13 - Eric's Vulnerable Journey04:44 - Eric's Family's Sacrifices08:15 - Pivotal Life Moments10:43 - Minivan Enthusiasm & Branding13:13 - Beat the GMAT16:00 - 3 Pillars of an Excellent Community19:32 - Choosing the Right Acquirer21:58 - Post-Exit World Travel24:43 - Working with Your Sister26:47 - Genesis of Hustle Fund29:25 - Hustle Fund's Secret Weapon30:29 - Hustle Fund's Investment Approach32:30 - Hustle Fund's Inclusive Mission34:44 - The Loneliness of Success37:07 - Navigating Life After an Exit39:56 - Camp Hustle42:05 - Power of Shared Experiences44:17 - Hustle Fund Community45:46 - Eric's Ideal CollaboratorsEric's StuffHustle Fund: https://www.hustlefund.vc/Eric's X: https://x.com/ericbahnEric's LinkedIn: https://www.linkedin.com/in/ericbahn/My StuffPodcast: www.mysecondmillionpodcast.comWebsite: https://www.connortomkies.com/X: https://twitter.com/ConnorTomkiesLinkedIn: https://www.linkedin.com/in/connortomkies/

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 growth and the unique challenges faced by entrepreneurs after an exit, this podcast offers valuable lessons for anyone looking to navigate the next chapter of their entrepreneurial journey. Discover the key to staying motivated, connected, and inspired in this thought-provoking conversation.Chapters:00:00:00 - Intro00:03:11 - Finding the Right Podcast Format00:06:48 - The Impact of the "My Second Million" Podcast Launch00:10:57 - Andrew's Outdoor "Anti-Office" Setup00:14:07 - The Potential of Video-First Podcast Content00:19:13 - Engaging Post-Exit Founders00:22:20 - The Anticlimactic Moment of Selling a Business00:24:28 - Building a Community for Post-Exit Entrepreneurs00:27:15 - Finding Motivation Beyond Fear After an Exit00:29:34 - Andrew's Search for Clarity00:32:17 - The Lost Art of Apprenticeship00:37:30 - Experience as an EOS Implementer00:39:39 - Building Relationships00:41:46 - ConclusionAndrew's StuffAndrew's Site: https://mixergy.com/Andrew's X: https://x.com/AndrewWarner?s=20Andrew's Book: https://www.amazon.com/Stop-Asking-Questions-High-Impact-Interviews/dp/1737676540My StuffPodcast: www.mysecondmillionpodcast.comWebsite: https://www.connortomkies.com/X: https://twitter.com/ConnorTomkiesLinkedIn: https://www.linkedin.com/in/connortomkies/