I grew up believing that I could have success, or friends — but not both.

What a shitty way to think. 🤦 

Especially since these days, my friends are profoundly crucial to my success.

In 2024, the badass business builders of Stealth Mastermind transformed how I approach my career. Hell, Drunk Business Advice wouldn’t exist without them.

And in 2025, I’m launching Rebel Scribes — an intimate cohort of business leaders who want to get better at telling stories that stick. Join us.

P.S. — Haven’t finished your Christmas shopping? Check out this gift guide for golf lovers. Three of the businesses are Stealth Mastermind members!

A bold and stupid plan

It was 2001, and the population in my little central Florida town was booming.

We needed a new high school.

Instead of building one, the school board decided to convert my spacious and relatively new middle school into a junior / senior high school.

👉 One. Grade. At. A. Time.

So what did this mean, exactly?

👉 When I was in 8th grade, my school serviced grades 6-8. 

👉 When my class advanced to 9th grade, my school serviced grades 7-9. 

👉 Then when we advanced to 10th grade, it was 7-10.

You get the picture.

It makes sense on paper. The school sat on a large enough parcel of land to expand, and the district was able to slowly add extra classrooms and amenities over the course of four years.

The plan seems perfectly reasonable.

Except for one little snag…

Kids need to get punched 👊

Ok, maybe not physically punched (although I have quite a few classmates for whom that would have done a world of good).

But they do need to get emotionally punched by experiencing life at the bottom of the totem pole.

It’s the only way to grow.

If you’re the smartest, most experienced, or most talented person in the room, get yourself to a different room — STAT!

In the case of my class, from 8th grade onward, we were never around people who were a step or two ahead of us in the journey to adulthood.

There was no incentive to grow up and behave more maturely so we could be accepted by upperclassmen — because there were no upperclassmen.

It was just us, and everyone who was behind us.

We were Kings of the Castle. Rulers of the Roost. Top Dogs.

For. Five. Years. 🤯

We could behave as poorly as we wanted, with zero social repercussions.

Wonderful. 🙄

Wait, I thought we were friends?

As you learned last week, I was a competitive figure skater back in those days.

This meant I was:

• Waking up at 4am every morning

• Training 4-8 hours every day

• Surrounded by skaters who were both older and better than me

The discipline that figure skating taught me extended to all areas of my life. I was an honor roll student, and excelled at the extracurriculars I participated in, like speech, music, and theatre.

This isn’t because I was smarter or more talented than other people.

It’s because I worked f*cking hard, and benefitted from an entire “second life” at the rink, where I was able to move through the milestones of adolescence with strong role models.

Early in my freshman year, I attended a district-wide high school speech competition with a group of my 9th grade besties. It was a super fun event, and we all enjoyed being at our first high school-level competition.

At the end of the day, everyone filed into the auditorium for the awards ceremony. One of my friends won third place in her category, and some others didn’t place, but received “excellent” and “superior” ratings. 

Well done! 🎉

When it came time to announce the category I competed in, I grew concerned when I didn’t hear my name announced for any of the superior ratings.

Then they announced third place…

Then second place…

And finally — my name! First place! OMG!

I was thrilled to win first place as a freshman. I couldn’t wipe the smile off my face if I tried.

My friends were not so thrilled. 😒

They un-invited me to the dinner we had planned for that night “because there wasn’t enough room in the car”.  My mom offered to drive me, but I read between the lines.

The following Monday, the “Brittanies” (two of my so-called friends — both named Brittany) were hosting our school’s morning announcements. 

They announced all of the results from the weekend’s speech competition — except that I had won first place.

If it hadn’t been clear before, it certainly was now.

I didn’t have friends at school. 😞

Holy shit, I have to do this for how long?

For the next four years, the Brittanies and their followers ruled the halls, petulantly tormenting me, with no social consequences.

I went through ebbs and flows of friendship with them, but every time I worked hard and achieved something, I was cast out once again.

My skating friends were dramatically kinder, more supportive, and more mature. 

But figure skating isn’t a team sport.

We were all —literally— competing against each other.

It’s such a bizarre experience as a kid to be watching my friend perform, simultaneously thinking:

1. I want her to do great, because I love her.

2. I hope she falls on her ass, because I’m competing against her.

My toxic school friendships, paired with the bonkers circumstances of my skating friendships, really f*cked me up.

I truly believed that I could either have success, or friends — but not both.

I chose success, and guarded myself against building authentic and vulnerable friendships — for 20 years.

What a waste

Fast forward to 2021. 

I was graduating from Harvard University’s executive AMDP program — quite possibly my greatest achievement ever.

And I had the honor of addressing my classmates during the commencement ceremony. 

That speech, in part, included these words:

For the first time in my life, I was surrounded by people who built me up instead of tearing me down.

They cared deeply about my happiness. And I could trust them with my insecurities. 

Sure, I got a stellar education at Harvard.

But more importantly, I had finally found my tribe.

I thought about my guarded approach to relationships, and felt a pang of regret. 

It had taken me far too long to realize that the key to both success and happiness is to surround myself with people who care about my goals as much as I do.

And I needed to do this with intention.

2024 absolutely rocked

At the beginning of this year, I set out to replicate the relationship experience of my Harvard program by creating Stealth Mastermind.

Here are the qualities I looked for in members—

• Great sense of humor

• Gains self-fulfillment from helping others

• Seeking a transformative entrepreneurial experience

And over the last year, we’ve welcomed 80+ truly badass business builders into our community.

This is hands-down my proudest achievement of 2024. 🥰

👉 Side note — are you an entrepreneur who belongs with us? Hit reply to ask for an invitation to apply.

But 2025 is going to slay

In addition to the continuation of Stealth Mastermind, I’m stoked to be launching Rebel Scribes — an intimate writing & storytelling cohort.

Many of you have reached out to ask me how the heck I craft stories for Drunk Business Advice.

So I’ve compiled all of my principals & practices into a six-week program.

What better way to kick off 2025 than to:

👉 Craft your killer origin story.

👉 Hone reflective practices to ensure you never run out of content.

👉 Master storytelling techniques that get people to care about what you have to say.

👉 Meet 12 new people (including me) who care about your goals as much as you do.

Join me. I’d love to work with you. ❤️

Cheers! 🍻

-Kristin :-)

P.S. — Happy Holidays! I’m going to take Boxing Day off, so Drunk Business Advice will be back in your inbox in the new year!

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