Made It with Connor Tomkies

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/ConnorTomkies
LinkedIn: https://www.linkedin.com/in/connortomkies/

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 and rewards of building "missionary" companies. Barak also shares insights on navigating the "idea maze" and the importance of aligning passion with business after a big exit.

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Chapters:

[00:00:00] Introduction and Barak's Background 
[00:01:00] Founding and Selling Intello 
[00:02:00] Building the Post Exit Founders Community 
[00:03:00] Post Exit Founders and New Ventures 
[00:04:00] Understanding Missionary Companies 
[00:05:45] Challenges After a Major Exit 
[00:07:15] The Idea Maze Concept 
[00:09:00] Examples of Missionary Companies 
[00:11:00] Frameworks for Ideation 
[00:13:00] Post Exit Founder Categories 
[00:16:30] The Messy Middle and New Directions 
[00:19:00] Sabbaticals and Self-Reflection 
[00:22:00] Scaling the Post Exit Community 
[00:25:00] The Importance of Offline Connections 
[00:27:00] Chapter Structure and Subgroups 
[00:29:00] Investing in Crawley Town FC 
[00:34:00] A Missionary Company Success Story 
[00:36:45] Facilitating More Post-Exit Founders 
[00:38:45] Closing Thoughts and How to Connect with Barak 

Barak's Stuff:

Bono: https://www.bono.so/
GiveButter: https://givebutter.com/
Wagmi: https://wagmiunited.com/
LinkedIn: https://www.linkedin.com/in/barakk/
X: https://x.com/barak_kaufman

My Stuff:

Podcast: https://www.madeitpod.com/
Website: https://www.connortomkies.com/
X: https://twitter.com/ConnorTomkies
LinkedIn: https://www.linkedin.com/in/connortomkies/

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. Learn how Pando has transformed the landscape of career risk management and what the future holds for this innovative business model.

Join Our Community!

Chapter Titles:

[00:00:00] Introducing Charlie Olson from Pando
[00:00:45] The Origin of Pando’s Name
[00:01:30] Income Pooling for Risky Careers
[00:02:45] Incentives and Career Risk Management
[00:03:30] Entrepreneurship in a Winner-Take-All Economy
[00:04:45] Pando's Start in Professional Baseball
[00:06:00] Entrepreneurs Pooling and Collaborating
[00:07:00] Contributions and Success Rates at Pando
[00:08:00] Entrepreneurial Pooling in Series B Stage
[00:09:00] Recruiting High-Caliber Entrepreneurs
[00:10:30] Community, Incentives, and Success
[00:11:30] Pando’s Potential for Industry Disruption
[00:12:45] Reimagining the Financial Institution
[00:14:00] Pooling as Upside Insurance
[00:16:30] Network Benefits and Negotiations
[00:19:00] Crowdsourcing Knowledge and Warm Intros
[00:21:30] Charlie’s Entrepreneurial Journey
[00:23:00] The Unique Vertical of Income Pooling
[00:24:00] Pando's Supportive Entrepreneurial Ecosystem
[00:27:00] Physical Therapy and Incentives
[00:29:00] Exciting Pando Companies in AI Revolution
[00:29:45] Long-Term Vision for Pando

Charlie's Stuff:

Pando: https://www.pandopooling.com/
LinkedIn: https://www.linkedin.com/in/charlie-olson/

My Stuff:

Podcast: https://www.madeitpod.com/
Website: https://www.connortomkies.com/
X: https://twitter.com/ConnorTomkies
LinkedIn: https://www.linkedin.com/in/connortomkies/

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.

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Chapters:

[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 Teams

Nick's Stuff:

Proud Ventures: https://www.proud-ventures.com/
Trumpet: https://www.sendtrumpet.com/?ref=nicklinkedin
Horseplay 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/ConnorTomkies
LinkedIn: 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-a5a3-42d48dde11ef

Chapters:

[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 Talent

Praveen'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/truecost

My Stuff:

Podcast: https://www.madeitpod.com/
Website: https://www.connortomkies.com/
X: https://twitter.com/ConnorTomkies
LinkedIn: 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.

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Join Our Community!
https://wealthwithrush.com/

Chapters

Apologies 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 Eyal

Gil's Stuff:

Website: https://stardustventures.us/
Email: [email protected]
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/ConnorTomkies
LinkedIn: 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/ConnorTomkies
LinkedIn: 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 Networking

Benji's Stuff:
Padel United Sports Club: https://www.padelunitedsportsclub.com/
Padel Mecca on Substack: https://substack.com/@padelmecca
Instagram: @PadelUnitedSC

My Stuff:

Podcast: https://www.madeitpod.com/
Website: https://www.connortomkies.com/
X: https://twitter.com/ConnorTomkies
LinkedIn: 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] Conclusion

Alexander's Stuff:

Website: https://alexanderswhite.com/
X: https://x.com/mralexwhite
LinkedIn: https://www.linkedin.com/in/alexanderswhite/

My Stuff:

Podcast: https://www.madeitpod.com/
Website: https://www.connortomkies.com/
X: https://twitter.com/ConnorTomkies
LinkedIn: 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.com

Chapters:

00:00:00 - Introduction

00:01:15 - Social Media Advertising in Eastern Europe

00:03:45 - Bootstrapping an Ad Network

00:10:00 - Challenges in the Eastern European Ad Market

00:15:00 - Selling the Company and Moving On

00:17:27 - Investing in Startups

00:24:15 - Pivot to Augmented Reality

00:30:00 - Building 3DLook

00:34:45 - Looking to the Future

00:37:30 - Closing Thoughts

Vadim's Stuff

Website: https://geek.vc/
Vadim's X: https://x.com/vadim_rogovskiy
Vadim's LinkedIn: https://www.linkedin.com/in/vadim-rogovskiy/

My Stuff

Podcast: www.mysecondmillionpodcast.com
Website: https://www.connortomkies.com/
X: https://twitter.com/ConnorTomkies
LinkedIn: https://www.linkedin.com/in/connortomkies/