221: 8-Figure Founder Shares Secret to Making More & Working Less with Jonathan Goodman

Most entrepreneurs believe growth requires sacrificing everything else. Jonathan Goodman proves you can scale a business without giving up your freedom. He’s built multiple companies, written 12 books (including The Obvious Choice), and scaled coaching businesses to 7-figures—all while spending half the year living abroad with his family. How? By mastering the art of incentives, knowing when to not scale, and investing in cash-flowing assets that work harder than he does. In today’s episode, we break down the wealth-building strategies Jonathan used to scale a business to $35M+ in revenue. We explore why most investments fail to beat the returns generated by a well-run business, a leveraged personal brand, or an asymmetric bet like Bitcoin. Jonathan also shares how he structures his businesses to maximize freedom and avoid the common pitfalls of scaling. If you’re looking for a playbook on building wealth, designing a business that doesn’t take over your life, and making sure your money works for you—not the other way around—this episode has the answers. In this episode, you’ll learn: ✅ Jonathan’s “whales and minnows” framework for eliminating 80% of your workload—why most entrepreneurs waste time on tasks that don’t move the needle, and how Jonathan ensures every hour works for him. ✅ The “eight-four rule” of seasonal living—how Jonathan avoids burnout and stays at peak performance by alternating between intense work sprints and extended time off. ✅ How to design scalable compensation systems that turn employees into partners—the secret to building a team that’s as invested in success as you are, without micromanaging. Show Notes: LifestyleInvestor.com/221 Tax Strategy Masterclass If you're interested in learning more about Tax Strategy and how YOU can apply 28 of the best, most effective strategies right away, check out our BRAND NEW Tax Strategy Masterclass: www.lifestyleinvestor.com/tax Strategy Session  For a limited time, my team is hosting free, personalized consultation calls to learn more about your goals and determine which of our courses or masterminds will get you to the next level. To book your free session, visit LifestyleInvestor.com/consultation The Lifestyle Investor Insider Join The Lifestyle Investor Insider, our brand new AI - curated newsletter - FREE for all podcast listeners for a limited time: www.lifestyleinvestor.com/insider Rate & Review If you enjoyed today’s episode of The Lifestyle Investor, hit the subscribe button on Apple Podcasts, Spotify, or wherever you listen, so future episodes are automatically downloaded directly to your device. You can also help by providing an honest rating & review. Connect with Justin DonaldFacebookYouTubeInstagramLinkedInTwitter See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.