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 Donald
See Privacy Policy at https://art19.com/priv
Popular Podcasts
Stuff You Should Know
If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.
Ruthie's Table 4
For more than 30 years The River Cafe in London, has been the home-from-home of artists, architects, designers, actors, collectors, writers, activists, and politicians. Michael Caine, Glenn Close, JJ Abrams, Steve McQueen, Victoria and David Beckham, and Lily Allen, are just some of the people who love to call The River Cafe home. On River Cafe Table 4, Rogers sits down with her customers—who have become friends—to talk about food memories. Table 4 explores how food impacts every aspect of our lives. “Foods is politics, food is cultural, food is how you express love, food is about your heritage, it defines who you and who you want to be,” says Rogers. Each week, Rogers invites her guest to reminisce about family suppers and first dates, what they cook, how they eat when performing, the restaurants they choose, and what food they seek when they need comfort. And to punctuate each episode of Table 4, guests such as Ralph Fiennes, Emily Blunt, and Alfonso Cuarón, read their favourite recipe from one of the best-selling River Cafe cookbooks. Table 4 itself, is situated near The River Cafe’s open kitchen, close to the bright pink wood-fired oven and next to the glossy yellow pass, where Ruthie oversees the restaurant. You are invited to take a seat at this intimate table and join the conversation. For more information, recipes, and ingredients, go to https://shoptherivercafe.co.uk/ Web: https://rivercafe.co.uk/ Instagram: www.instagram.com/therivercafelondon/ Facebook: https://en-gb.facebook.com/therivercafelondon/ For more podcasts from iHeartRadio, visit the iheartradio app, apple podcasts, or wherever you listen to your favorite shows. Learn more about your ad-choices at https://www.iheartpodcastnetwork.com
Dateline NBC
Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com