^{Instagram Live}

That was fun!

Hosted another Instagram live last week. This one was more about personal finance and content related questions. But nonetheless, thanks to those of you who joined!

I’m aiming to do another one next month!

^{Top Content From Last Week}

The “Micro” Generation

There is a group of us who graduated high school between 2008 - 2015 (and I imagine that includes at least a few thousand readers of this blog) and don’t like to admit that we’re the lucky ones.

You can also watch it on TikTok.

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Nobody Knows What They’re Doing (and That’s the Point)

The longer I do this, the more convinced I am that nobody knows what they’re doing, and that’s not an insult. It’s actually the great equalizer.

Every day I meet families trying to make sense of their finances, advisors trying to grow their business, executives running billion-dollar divisions, and founders raising capital. Everyone’s just guessing, iterating, reacting. We like to pretend there’s a master plan, but the truth is we’re all building in real time and hoping the next move makes sense when we look back on it.

Nobody Knows Anything and Nothing Matters

When I moved to Chicago to join the J.P. Morgan Private Bank, my job was simple: bring in business. I was partnered with a managing director, and my day-to-day was chasing Fortune 500 execs, billionaires-in-the-making, and people whose net worths were so high they needed a team just to keep up with their own lives.

I was 25, sitting in boardrooms with people who were supposed to have all the answers…CMOs, CFOs, founders, lawyers. One day, after a marathon meeting about a spin-off deal, one of those execs tapped me on the shoulder in the elevator. He pulled me aside and said, “Let me tell you something, nobody knows anything, and nothing matters.”

At first it sounded bleak, but he said it with this calm confidence, like he’d finally made peace with it. What he meant was that everyone’s winging it. Every “expert” is educated-guessing. Every “strategy” is just a test run.

Since then, I’ve met the founders of NerdWallet, Brex, Morning Brew, DraftKings, WHOOP, LemonPerfect, and people who’ve actually made it. And after the shiny headlines fade, most of them admit the same thing: they were just figuring it out as they went.

The higher up you go, the more you realize everyone’s guessing, the best just guess faster, guess more, and adjust quicker.

Finding Clarity in Chaos

Earlier this week, we found out by accident that our Facebook page had over 250,000 visits last week. Why? Because every video I’d been posting on my personal TikTok had been auto-uploaded to a dormant Habits page with zero context, zero links, and zero product info. It was performing like crazy, but nobody even knew what Habits was.

That’s the irony of building in public. You can spend months perfecting strategy, and then one small fluke blows it all up. Sometimes it’s a glitch. Sometimes it’s luck. Sometimes it’s just timing.

And as for perception, I’ve met founders worth millions who still work off mattresses on the floor, and others who had $10M in ARR evaporate in six months because Meta rolled out a feature that crushed their model overnight. Nobody has it fully figured out.

So these days, I don’t obsess over perfection. I block one day a week for no meetings, just space to think. Because growth comes less from grinding harder, and more from knowing where not to waste your energy.

Progress isn’t about doing more it’s about making peace with the fact that half of it won’t work.

What Investors Don’t Tell You

I’ve spent a lot of time with investors this year, probably fifteen in the last six weeks alone. Some over Zoom. Some in coffee shops. A few over drinks. You can tell within five minutes whether someone’s really listening or just checking a box.

One investor I met in person told me, “I love your conviction and traction, but you’re early.” I laughed and said, “Yeah, I’ve been early for two years.” We both smiled because we knew what that really meant: come back when it’s safer.

I don’t take it personally anymore. Fundraising is mostly timing and storytelling. You’re catching people in between meetings, moods, and fund cycles. Half the game is just getting them to care long enough to see what you see.

That said, I’ve also met a few who do get it. Who’ve been founders. Who’ve had the sleepless nights and the false starts. And when those people lean in, it’s different. You feel it. Because you can’t fake empathy for the chaos of building something from nothing.

The best investors aren’t betting on your deck, they’re betting that you’ll survive the chaos long enough to make it mean something.

Final Thought

Every founder, creator, and operator I know is making it up as they go, myself included. The ones who win aren’t the ones who figure it all out, but the ones who stay calm when it all falls apart.

So yeah, nobody knows what they’re doing. That’s not the problem, that’s the point.

Certainty is overrated. Curiosity is what keeps you moving.

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