It’s a holiday weekend!
AKA — a rare span of days when entrepreneurs actually have time to get shit done without everyone pestering them. And oh, lordy, I need this time.
So instead of dreaming up a brand new issue of Drunk Business Advice, I thought it’d be fun to reflect back on some of my favorite issues from last 12 months because holy moly it’s October already.
(I’ve decided on my Halloween costume, btw. It’s really scary. I’m going as Elizabeth Holmes.)
So have a little scroll, and enjoy some of these stories you may have missed!
Somewhere between the invention of suburban sprawl, the rise of Amazon, and the arrival of AI girlfriends, we apparently decided that interacting with other humans was an unnecessary inconvenience.
And now we're paying the price.
For entrepreneurs, however, this increasingly antisocial world presents one hell of an interesting opportunity.
Because while everyone else is busy figuring out how to eliminate human interaction from their business models, I'm betting there's a fortune to be made by bringing it back.
“I blew it.”
Those three words, uttered by American figure skating badass Ilia Malinin after his disastrous Olympic performance, hit me like a damn freight train. Because 25 years ago, I blew it, too.
Before I was an entrepreneur, I was a competitive figure skater with Olympic dreams, a broken hip, and a childhood spent inside a freezing metal box.
And while my skating career ended in disappointment, the lessons I learned from my greatest competitors shaped everything that followed.
“You can't prepare for everything, but you can prepare for anything,” sounds like the kind of motivational hooey you’d find plastered across a stock photo of a bunch of dimwits who are way too happy to be sitting in an office.
Except this particular nugget of wisdom comes from a guy who ran the Super Bowl for a decade, produced 31 major professional sports drafts, and quite literally kept his cool when the lights went out in front of 115 million people.
And it happens to be the most important leadership lesson I've ever learned.
When was the last time you did something creative that had absolutely nothing to do with making money?
And I'm talking about actually doing something — not sitting on your ass consuming somebody else's creativity.
Because there's a fascinating body of research suggesting that the distinction between participating in the arts and merely appreciating them might be a lot more consequential than we realize.
Especially for people whose livelihoods depend on solving complicated problems.
Remember Purdue Pharma? Those sweethearts who helped unleash one of the most devastating addiction crises in American history?
Well, somebody apparently found their old marketing playbook and decided it deserved a second act. It’s Kalshi and Polymarket.
And while their products are substantially different from OxyContin, their strategies for getting consumers hooked on a shit product that is horrible for them bear some remarkably disturbing similarities.
An here are a few ICYMI’s from recent weeks that I’m also particularly proud of:
Enjoy the rest of your holiday weekend, friends!
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.








