How I Got Here (And An Invitation)

Two weeks ago, I introduced the three forces reshaping the investment world that I see playing out right now, as we speak:

The shift from public markets to private markets.

The shift from investment advisor to family office paradigm.

The shift from net worth to cash flow.

Last week, we talked about the contrarian fix: the choice between being a Textbook Investor and being a Lifestyle Investor.

This week, I want to take a step back and share something a little different.

You might be wondering: Where did all of this come from? Did these ideas just emerge out of thin air? 

Well, this is something I’ve been thinking about, implementing, and refining for a very long time… years before I built the Lifestyle Investor Mastermind, years before I wrote The Lifestyle Investor book, and years before I even started the podcast.

And I thought I’d share a few parts of my story that, honestly, most people don’t know about, but which I think will be useful context for you as we dive deeper together.

The One Habit That Changed Everything

I’m not where I am because there’s something uniquely special about me.

I didn’t have a big exit. I didn’t inherit money, and I didn’t win the lottery.

But I will tell you one of my secrets… 

One habit that compounded over time and transformed everything about how I invest, how I think, and who I’ve become:

Every single week for the last 20 years, I’ve had lunch with a new person.

It’s kinda wild if you really think about that. 

Fifty-two weeks a year. Times 20 years. That’s over a thousand different people I’ve sat across a table from, asked questions, listened to, and learned from.

Picture that: A thousand incredible people, laid shoulder to shoulder. Business owners. Investors. Experts in tax strategy and real estate and private equity. People who had figured out things I hadn’t.

I don’t take any of the credit. I give all the credit to the people I’ve had the opportunity to learn from.

But it did come from having a curious mind, and a desire to do things a little differently.

The Transformation

Early in my career, I graduated from the University of Illinois with a finance degree. And not the generic kind, I had professors who were actual practitioners. We studied real arbitrage strategy, M&A, investment banking, real estate. I was one of 20 students selected out of the entire business school to manage $1 million of an alumnus’s capital for a year. We did well.

So I wasn’t starting from scratch. I had real training. But after graduating, I found myself building a business at Cutco, doing well by most measures, and still watching people around me who were doing all the ‘right things’ and never actually getting ahead. They were doing all the “right” things: saving, investing in the market, following conventional wisdom, and yet financial freedom always felt just out of reach.

I didn’t want that to be my story.

So I became intentional about learning. I started having those lunches, and asking different questions. I started studying how the ultra-wealthy actually build and protect their wealth, not what the textbooks say.

And something started to shift.

I realized that the knowledge I was gathering… from those thousand lunches, from networking with family offices, from studying data from Goldman Sachs, Morgan Stanley, JP Morgan and UBS, wasn’t knowledge that most people had access to.

Wall Street controls the education. They want your money in the stock market because that’s how they get paid.

But the ultra-wealthy? They play by a completely different set of rules.

And I wanted to bring those rules to people who weren’t billionaires, but who wanted to think and invest like them.

Why I Do What I Do

I’ll be honest with you, this was never really about investing.

It was always about family first.

I have a good friend, Jon, who built something extraordinary with Front Row Dads (FRD). What always struck me about him wasn’t the business, it was how he built it. He’s a family man with a business. Not a businessman with a family. That distinction sounds small. It isn’t.

So many high achievers I know got it backwards. They told themselves the business came first, just for now, just until they hit the next milestone, and then they’d slow down. But the milestones kept moving. And the family kept waiting.

I didn’t want that to be my story.

Here’s what I believe: when you’re financially free, you make better decisions for your business and for your family. You stop weighing every choice against “can I afford this?” and start asking “is this the right thing to do?”

I’ve watched entrepreneurs make poor hiring decisions because it would mean less money in their own pocket. I’ve watched business owners avoid investing in their people, their marketing, their R&D, not because it wasn’t the right call, but because fear made the decision for them.

But when your lifestyle is already covered by passive income, everything changes.

You can take smarter risks. You can invest in your people. You can say no to bad deals. And you can be present with your family without that constant low-grade anxiety – am I doing enough, earning enough, saving enough?

That’s why I built the Lifestyle Investor community.

And not to be a guru at the top. I want to be clear about that. The genius here isn’t me, it’s the collective wisdom of the group. It’s the deal flow that emerges when you surround yourself with other people playing the same game. It’s the network of specialists – tax strategists, estate planners, seasoned operators – that you get access to when you’re in the right room.

Here’s something I don’t talk about enough: when COVID hit and my weekly lunches stopped, I started something called the Investment Happy Hour, just a Zoom call to keep the conversations going.

What I thought would be a temporary fix turned into something I genuinely loved. Instead of learning from one brilliant person over lunch each week, I was suddenly in a room with dozens of incredible investors, operators, and thinkers every single month. The compounding of that wisdom was unlike anything I’d experienced before. And it showed me something important – the community itself was the asset.

I bring the best of what I learn from groups like Tiger 21 and YPO and other ultra-high-net-worth communities, and I share it with our Lifestyle Investor members. I curate the best learnings from the thousand-plus lunches I’ve had, from the family office data I study, from the experts we bring in.

And then the real magic happens: the conversations that spark between members. The connections. The wisdom that flows between people who are on the same path.

That’s what this is really about.

An Invitation

These first three issues of the Lifestyle Investor Lens have been foundational. The forces reshaping wealth. The choice between Textbook and Lifestyle. And now, my story.

From here on out, I’ll be sharing what’s happening inside our community – the conversations, the deals, the strategies, the lessons on a weekly basis. I’m excited about what’s ahead.

But before we continue, I want to extend an invitation.

If what I’ve shared over these three weeks has resonated with you… if you’re ready to stop being a Textbook Investor and start becoming a Lifestyle Investor, I’d love to tell you more about how our community works.

No pressure. No hard sell. Just a conversation to see if it might be a fit.

Send me an email if you’d like to learn more.

Either way, I’ll see you next week, and I’m grateful you’re here.

Justin

P.S. I’m building out the topics for upcoming issues, and I’d love your input. 

Send me an email and let me know: What’s a question you’d love for me to tackle in a future edition of the Lifestyle Investor Lens? I’m making a list as we speak.