Lifestyle Investor Lens

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,…

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…

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.…

Whenever I give a keynote, there’s one question I ask that seems to stop people in their tracks: What would you say your network is worth? Think about it. As an asset. On your balance sheet. What’s the value? Most people have never thought about it this way. They think of their network as… people…

Over the last several weeks, I’ve been sharing a framework for thinking about wealth differently: the three shifts, how to find and evaluate deals, and the importance of tax strategy. This week, I want to zoom out and talk about something bigger. Something that I believe represents the single greatest wealth-building opportunity in a generation.…

Last week, I shared the five filters I use to evaluate any deal. This week, I want to talk about an investment that doesn’t fit neatly into any of those categories, but that I believe outperforms everything else over the long run. When people ask me, “Justin, what’s the best tangible investment you’ve ever made?”…

Over the last few weeks, I’ve been laying out the three major shifts happening in how wealth is built: the move from public to private markets, from investment advisor to family office paradigm, and from net worth to cash flow. If you’ve been following along, you might be thinking: Okay Justin, I get it. Private…

Over the last few weeks, I’ve gone deep on the first two shifts reshaping how wealth is built: The shift from public markets to private markets. The shift from investment advisor to family office paradigm. Today, I want to tackle the third shift, and honestly, this is the one that changed my life. The shift…

Last week, I went deep on the first major shift happening in wealth building – the move from public markets to private markets. This week, I want to tackle the second shift: From Investment Advisor to Family Office Paradigm. This one might be the most misunderstood of the three. The term ‘family office’ is everywhere…

A few weeks ago, I introduced the first of three major shifts happening in how wealth is built: The shift from public markets to private markets. I got a lot of replies asking me to go deeper on this one. So today, I want to unpack it, because once you understand why the ultra-wealthy invest…