But in this case, I’m 99% sure it’s the right decision.

Don’t worry. I’m not talking about Drunk Business Advice. You’ll continue to be subjected to my email hijinks for as long as you’ll tolerate me. (Please continue to tolerate me.)

👉 Stop making a virtue out of your coping mechanisms.

👉 You can outsource almost everything — except belonging.

And now — the story behind why this advice matters. 👇

I’m an extrovert who spent my entire life pretending to be an introvert to excuse the fact that I didn’t really have any meaningful friendships.

I told myself I was far better off not belonging to a group… a team… a tribe. Because people would always hurt me. They would always let me down. I could achieve more by flying solo.

This is what I had to believe.

Because if it wasn’t true, then I was just a sad sack of bones with no friends. I was just a loser sitting by herself at the lunch table — not a brave warrior woman, operating at such a high level of self-actualization that the judgement of others rolled off me like droplets of rain on a Teflon coat.

But of course, I did care deeply about what others thought of me. We all do.

Looking back, I cringe at my younger self. What a pessimistic, self-preserving, colorless world I built. 

But I can’t completely regret it, because if I hadn’t swung so far into loneliness and distrust, there’s really no way of knowing whether I’d be standing here today with such a novel point-of-view on this topic. There’s no way to know if I would have assembled the community that now surrounds me. There’s no way to know if I would have acquired the perspective that accompanies the scariest sentence in the English language:

“I was wrong.”

My transformation began in 2019, when (against every prediction anyone could have ever made about my future) I went to executive school. And not just any executive school — Harvard.

Trust me. I was as shocked as you are. I still am.

As a hot-shot 32-year-old, I was the youngest person in a class of 44 real estate executives from around the world. 

There were also more people named John, James, or George in my class than there were women — a ratio which was consistent with my real-world experience in real estate development. 

So while I wasn’t surprised to be a younger female in an older male-dominated executive program, I immediately wrote off the possibility of building friendships with these guys. I thought the “networking” would be fire — and I’d learn a shit-ton from my classmates — but… friends? Nah.

That assumption was blown to bits the first day I arrived on campus. 

As it turned out, my new classmates were the warmest, smartest, most disarming people I had ever met. There was a seismic explosion of community, like we were all siblings separated at birth, wandering through the world on our own lonely journeys, knowing something was missing from our lives, but unable to put our finger on it.

Or at least, that’s how I felt.

Finally, I understood what I had been missing. And I was angry with myself for avoiding real friendship for the sake of preserving my own self-importance for so many years.

To be clear — not all of these friendships worked out in the end. Some of these people did hurt me. Some of them broke my trust. Some of them probably didn’t deserve my trust to begin with.

And of course, some settled into warm acquaintances rather than ride-or-die besties. And that’s all ok.

Because adopting this tribe was the biggest net-positive decision of my life.

The entire experience left me wondering — “Could I create a community like this without the Harvard brand to hold it together?”

About a year after graduating, a unique opportunity came knocking. One of my favorite business newsletters, The Hustle, was looking for someone to take over their premium entrepreneurship publication, which included a (pretty darn massive) online community of ~16k business builders.

It was called Trends.

I had been a member of Trends for a few years at that point, and with my heart opened by my experience at Harvard, already made some badass new friends from the group. So taking over the leadership of this super cool club full of super cool people was a no-brainer for me.

Unfortunately, once I got inside, I discovered the organization was rife with misalignment. 

The Hustle, a massive free newsletter with millions of subscribers, had just been acquired by HubSpot, a cringy post-IPO tech behemoth, who bought it for the distribution. Trends just sort of… came with it as a package deal.

So the scrappy entrepreneurship community I was in charge of was now just a puny $5 million dollar drop in an enormous $1.5 BILLION DOLLAR HubSpot bucket. And it was HubSpot’s only non-software product. 

Trends sure as hell wasn’t going to last in that environment. And neither was I.

I noped out of there pretty quickly, but not before connecting with some standout folks, and getting a hunch I couldn’t shake…

Out of Trends’s 16k members, only a few hundred were really engaged, and a few dozen were truly exceptional. 

So I wondered — what would happen if the best entrepreneurs from Trends started developing real relationships? Not in the “I always comment on your posts” sort of way. Not even in the “Let’s team up and launch a new business together” sort of way. 

What would happen if they connected in a “I’ll bail you out of jail, be the godparent to your kid, and share a summer house for 20 years” sort of way? My experience at Harvard told me that putting people in a room together who are…

…could spark absolute f*cking magic. 

I knew HubSpot was going to be shutting down Trends in a matter of months, so I got to work on my hypothesis, rounding up the most interesting entrepreneurs I had met through that community. And since it wasn’t yet public knowledge that Trends was getting murdered by its corporate overlord, I gave my little “stealth mode” project a temporary title:

The name stuck.

For the last few years, Stealth Mastermind has been my happy little corner of the world. My secret weapon. My team of talented people who care about my goals as much as I do — and I theirs.

(This is something I wish for all of you. Go assemble a group like this right now. I’ll wait.)

Without the comradery, accountability, and inspiration of the Stealth Mastermind community, Drunk Business Advice would not exist (hat tip to the famous Rob Capili on that one).

During my nearly 3 years running Stealth Mastermind, I’ve proudly produced:

If that sounds like a lot — you’re damn right.

Leading a community is a colossal commitment. But it’s also a transformative one. I got as much as I gave. And I’m overwhelmed with gratitude for the rockstars who said, “F*ck it, I trust you” — and leapt into my little experiment with zero hesitation.

But toward the end of last year, something started to shift.

Don’t get me wrong — shit was going gangbusters in Stealth Mastermind. We had just welcomed a new cohort of highly energized members. Our programs were on fire. And people flew across oceans just to attend our Christmas party. 

What was shifting was… me. 

I had built Stealth Mastermind for a particular season of my life. And the nature of seasons is that they eventually change. I fought the feeling for a while, but I knew that I no longer possessed the energy or focus that was required to run the group — and it was time to dissolve it.

So I assembled a handful of members who had been with me since the very beginning, and broke the news. I had already made the decision to close the group, but I wanted their counsel on the best way to maneuver it with our members.

Their response?

“Absolutely f*cking not.”

And in that moment, three of them put up their hands to take it over. They didn’t even have to think about it. They were ready. They wanted to lead Stealth Mastermind into a new season. 

This thing was bigger than me. And it no longer needed me.

Here I was, desperately trying to hold the community together while being pulled in a million new directions, not realizing that Stealth Mastermind had built-in glue.

So now, on July 1st, I’m officially “handing over the keys” to Jason De Los Santos, Rob Capili, and Michael Jacobs — three of the most generous, creative, and freakishly smart people I’ve ever had the pleasure of knowing.

And better yet — this proves my hypothesis.

In the case of my Harvard community, the Harvard “brand” assembled us, but our relationships weren’t held together by Harvard — they were held together by us, long after we left Cambridge. 

It’s the same thing with Stealth Mastermind. My personal “brand” assembled this group, but the group doesn’t need me to thrive. In fact, fresh leadership is the best thing for it.

So what’s next for me?

Stay tuned. 😉

Cheers! 🍻

-Kristin :-)

P.S. — I don’t just write Drunk Business Advice — I bring it to life on stage. And I’d love to speak at your next event. Hit reply or click here to learn more.