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Justin Donald
Interview with Kip Sowden & Doug McKnight How Vertical Integration Scaled This Real Estate Firm to $5 Billion AUM with Kip Sowden & Doug McKnight Achieving success in real estate isn’t about predicting the future. While many investors have spent the last few years waiting for certainty, some of the best operators in the…
I gave a talk a few months back to a room of about forty founders. Pure entrepreneurs. Not a single non-operator in the group. I opened with something that landed harder than I expected. “Entrepreneurs are the worst investors I know.” A few laughs. A few looks of “wait, what.” And then I explained why,…
Interview with Jeff Zaugg The Invisible Riptide That Pulls Entrepreneurial Dads Away From Their Family with Jeff Zaugg Running a successful business doesn’t automatically translate into success at home. In fact, many ambitious entrepreneurs and high performers slowly drift away from the people they care about most without even realizing it. And by the…
Some entrepreneurs build big businesses. They scale fast, break things, and eventually find themselves exhausted at the top of a mountain they didn’t really want to climb. Then there are the rare leaders who build businesses that work, not just for the bottom line, but for their teams, customers, and themselves. The gold standard for…
A friend forwarded me an email last week that I haven’t been able to stop thinking about. The subject line was three words… “Never trust a skinny chef.” It’s an old expression. If the chef won’t eat their own cooking, you probably shouldn’t either. He was applying it to something most investors never even think…
Interview with Jesse Flocken The Firefighter Who Walked Away From Early Retirement And Chose Entrepreneurship with Jesse Flocken “I can’t do this for one more day.” Jesse Flocken had what most people would consider a dream life: a stable career, a guaranteed pension, a great family, and retirement within reach before his 40th birthday.…
If you’ve been following my journey at The Lifestyle Investor, you know I have one core mantra: It’s not about what you make; it’s about what you keep. That’s why, in my opinion, a world-class tax strategy is the most important skill you can have. Why? Often, a sophisticated tax move can save you more…
A few weeks ago I wrapped up what I’d been calling the foundational series… the three shifts, the Textbook vs. Lifestyle Investor framing, the Freedom Number, the five filters, all of it. From here on out, I want to share what’s actually happening week to week. The conversations. The deals. The questions members are asking.…
Interview with Talor Zamir The Power of Scheduling Think Time to Unlock Peak Performance with Talor Zamir If your business is growing but your energy, focus, or quality of life is declining, something is out of alignment. And that disconnect is exactly what today’s episode is all about. I’m excited to introduce you to…
I’ve always believed that life is about more than numbers on a balance sheet. Wealth matters — but only as a tool to support meaningful work, compelling stories, purpose, experiencing the arts, and memorable experiences. As Lifestyle Investors, we spend plenty of time mastering the how of wealth: cash flow, tax strategy, asset allocation. Every…