🚩 The term “red flag” is often used to describe warning signs that one should detect before investing in a relationship (be it business, or otherwise). 

But I think that term is a crock of shit.

“Red flag” suggests there’s some sort of blatantly obvious billboard we should be on the lookout for. But most of the time, the signs we should sniff out are far more subtle. And they’re often covered by big “green flags” that trick us into ignoring our guts.

So if we’re looking for “red flags”, we’ll probably miss crucial, subtle signals.

Now — this is the part of the story where I’m going to get way more honest than I ever have before…

I have huge f*cking trust issues.

👉 Just because someone extends trust doesn’t mean they’ve earned yours.

👉 Don’t mistake flattery for character.

👉 And if someone weaponizes vulnerability — be wary. That’s not trust. That’s manipulation.

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

But first…

On Thursday, I busted through my stage fright, and hosted my very first LIVE podcast with the legendary Jesus Vargas.

If you weren’t there live, you can catch the replay here.

On the pod, we dove deep into:

So go check out the replay. 👇

Jesus Vargas is the owner of LowCode Agency, a badass software development agency that builds custom apps twice as fast, and for half the cost, of traditional software developers. His sponsorship of Drunk Business Advice keeps this content free. 🙏

I was about 10 years old the first time I saw the movie JAWS. I watched it with my dad. 

Halfway through the film, as Brody, Hooper, and Quint set sail on the (needed-to-be-bigger) Orca to hunt down the shark that had been terrorizing Amity Island, he turned to me and said:

👉 Out of those three guys, only two of them are going to survive. Which one do you think is going to die?

WTF kind of question is that for a kid?

Also, um, kind of a spoiler. 🙄

It has taken me 30 years to realize why he forced his terrified 10-year-old to pontificate on the horrific fate of a beloved movie character.

And no, it wasn’t because he wanted to ruin the film for me.

He wanted to teach me a lesson that, frankly, I’m still struggling to fully grasp.

Dad is a street kid from Detroit. He didn’t go to college. In fact, he barely graduated high school.

But the guy’s got business instincts like a… shark. He knows when somebody’s bullshitting him to get what they want. He senses when priorities are screwy. And he can smell a shyster from a nautical mile away.

So by asking me “which guy is gonna get chomped in half,” he was really asking…

He was trying to teach me how to read people. He wanted me to think about the behavior these characters had exhibited up until that point, and the unique situations each of them found themselves in.

Then he wanted me to predict what was most likely to happen in the future based on that information.

I doubt that my dad even remembers asking me that question while we were watching JAWS, but that moment in my childhood has always stuck with me.

When I met Shawn back in 2019, I immediately liked him. Everybody did. He was warm, incredibly smart, and had an easy laugh. He was a great listener, and had a way of making anyone he was talking to feel like they were the only person in the room.

And as classmates together at Harvard, a certain level of trust was assumed purely as a result of the environment we met in.

That trust tightened when Shawn and I were placed together on a 7-month team project (the first assignment of our executive program). We worked closely together to deliver an incredibly complex project. We became close friends, and talked almost every day.

So when Shawn decided to launch a startup, and was seeking angel investors, many of us wrote checks. Including me.

About six months later, I received a surprising phone call from Shawn, asking if I’d consider joining his startup as COO. According to him, the product was now ready for customers.

In his words, he needed a COO who he could “trust blindly” to lead the company from development into operations. And he wanted me.

I was honored. But I wasn’t in a position to work my ass off in exchange for equity until the product gained enough traction to raise a Series A round. I needed a salary — and not a piddly one. I’d have to give up a lot to take on this role. Shawn promised to give me what I needed.

What followed was a chapter of my life that I wish I could close my eyes and forget. Because it’s one thing to get screwed by a boss or a business partner. 

But it’s heartbreaking to get screwed by a friend.

Reflecting back, there were definitely signs that Shawn wasn’t someone I should’ve jumped into business with.

But they weren’t glaring “red flags”. They were microscopic warning dots, that only when carefully connected, clearly spelled out “STAY THE F*CK AWAY”.

And do you know how I missed them?

By reciprocating trust when I shouldn’t have. When Shawn said he trusted me “blindly” my instinct was to trust him back.

This is classic human wiring. Reciprocity is baked into our DNA. It’s what makes polite society function — and what makes us susceptible to getting screwed.

It’s also a little ego-strokey:

In short — we feel obligated to reciprocate trust.

It’s the same reason we feel bad when someone gives us a gift we weren’t expecting. We crave social equilibrium. 

So when someone tells us they trust us, it’s like a gift we weren’t prepared for. We think “Shit. I owe them now.” And we give them trust in return, even when it’s utterly undeserved.

And that false sense of trust can make us completely blind to the warning dots.

It’s total manipulation.

I’m still navigating the direct fallout from this ordeal, like: 

But the psychological consequences run deeper.

I have big plans for Drunk Business Advice, and the suite of businesses I’m building around it (like Drunk Writing Advice, Rebel Scribes, and Stealth Mastermind).

And while I’m pretty damn proud of my skills in product development, editorial, and operations, I truly suck at marketing.

So for the last year, I’ve been agonizing over the decision to bring on a partner to fill that gap in my strengths. But every time I feel ready to partner with someone, I crawl back into my solitary hole, terrified of another Shawn-like scenario.

My friends are tired of hearing me whine about this decision. Well, all but one friend…

Katie Lukashow has welcomed my whining — but she’s also forced me to be productive about it. 

Last week, when we were chatting about this issue over Zoom, she shared her screen with me, and showed me this hella confusing flywheel chart. 👇

She said, “Ok, you have a very strong belief that you can’t trust a partner. That’s fine. How can you alter your behavior so you can still achieve the results you desire?”.

Holy shit. My mind blew open. 🤯

I realized that I trust pretty damn freely when stakes are low, but completely shut down when stakes are high.

It’s not binary. It’s not that I can’t trust. My trust is on a scale. 

So rather than asking the question “Do I trust a business partner,” I needed to be asking, “At what level do I feel comfortable giving trust, and how can I make that work for me?”.

Katie — you are a legend, and I can’t thank you enough for guiding me out of murky, shark-infested waters, and onto a crystal-clear beach.

It turns out that my decision doesn’t need to be as serious as selecting the right sailors to risk my life with. I might be able to achieve the same result by sharing a beer on the dock.

Cheers! 🍻

-Kristin

P.S. — You should 100% go talk to Katie. Her company is The Possibility Institute. She’s the real f*cking deal.

And don’t forget, Drunk Business Advice is FREE because of Jesus Vargas, and his team at LowCode Agency — so show ‘em some love!

Follow @lowcodeagency LinkedIn, Facebook, X, and YouTube.

Whether you need help building an MVP, creating software to run your business, or even just a badass website, I highly recommend the savvy team over at LowCode!