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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 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
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/
[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/
Creators and Guests
What is Made It with Connor Tomkies?
"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.