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Yesterday, a young entrepreneur I mentor asked me a simple question during our regular meeting.

“Kasey, what’s one mistake you’ll never repeat in business?”

I’ve been an entrepreneur for 10+ years now. And since I send this newsletter to ~23,000+ people every week, you would think the answer would be something I write about often! But it’s not.

It’s something deeper. Something truer. Something I should absolutely talk about more.

I haven’t talked to you about this mistake in a while, and I’ve never explained the deeper lesson I learned from it. At least not like this.

And as I was narrating the story of how I learned the mistake, what impact it had on me, and how it has shaped my decision-making process, I knew I had to write a newsletter about it.

So today’s newsletter is a more refined version of the conversation I had with my mentee.

I’ll tell you 2 stories from my life, the painful lesson I’ve learned over and over again, and we’ll cap off with some actionable advice I’d give to my younger self.

Ready?

Startups and SaaS founders outsourced their Go-to-market strategy and other marketing verticals to me.

I had hired one person, and we were a team of 2. And we were doing great (we were at $20-30k/month) with clients and repeat business.

Then came the twist.

And their pitch got me VERY excited.

We’d already referred business back and forth multiple times. We were bringing in equal revenue at the time. They wanted me to become the CEO and the face.

And we were good friends, so it all felt like a natural fit. Everything felt perfect to say YES.

There was just one slight detail which concerned me: They wanted us to join as equal partners. A 33-33-33 split. Logically, it should’ve been 50-25-25, because I was bringing half the revenue to the table.

I remember thinking, "I should push back on this. This doesn't feel right."

But then I was like, “Nah, we're friends. It'll all work out. It'll be fine.”

Within about 3 months, because of my network, I brought in several new deals to get us to about 90k in MRR, and we were scaling FAST.

We then decided to bring on a fourth partner, at the recommendation of our mutual mentor, who was building a customer success agency. Now, we were at $120k MRR. We were cooking.

But then the bubble burst.

I knew things were a little tense, but thought we were working it out. And then one of the brothers didn’t show up on a sales call with a prospect and a client called letting me know his email to me had bounce back.

They deleted my email.

And then all hell broke loose. They called my clients trying to convince them to jump ship (they didn’t) and I called my lawyer.

It was one of the most stressful times I’ve ever gone through. Even worse than my divorce.

And getting out of this jam took a big piece of me! (not the mention the scars I had to heal because of this).

All because…

No, before I tell you the mistake, we need another story.

We had a great cohort offer. People found it valuable. And we were growing quickly!

What started as a fun project was about to turn into a full business. So I flew out to New York to spend a few days with my business partner and their family. We'd never met in person before.

On my last day there, we were talking about something deeply personal: a serious health condition I'd been dealing with. We were laughing at first, you know, the way you do when you're telling a story.

You know that feeling when you're laughing WITH someone, and then suddenly it feels like they're laughing AT you?

I got that feeling.

The laughter kept going, but it didn't feel right anymore. I wasn’t the one making the jokes. They were.

And even when I reminded them of the severity of this health issue, the jokes continued. I remember getting in my car to drive to the airport to fly home. I cried the whole way there.

This time I didn’t ignore it, but I also didn’t fully act on it.

Within 6 months, the inevitable happened once again. I started feeling a lack of respect and a lack of care. One thing leading to another, we had to end the business and part ways (more hurtfully than happily).

I caught the bug faster this time. But it still cost me a LOT.

Which finally brings us to the KEY lesson I’ve learned and the mistake I’ll try never to make again.

Not paying attention to my intuition (especially with long-term decisions) always hurts me. Maybe not right away, but eventually.

Steve Jobs was renowned for being an a**hole (just read his daughter’s memoir), but this one quote of his absolutely hits the nail on the head.

In both of these stories, my intuition was giving me hints.

They were subtle, but I was getting glimpses of the seeds of destruction that lay in the path I was on. And while I’m proud of the work I did in both these phases, I would’ve saved myself a LOT of trouble and sleepless nights (and money), had I not IGNORED my intuition.

Especially if the decisions involve people, and if you have similar people-pleasing traits, this skill becomes crucial.

Intuition is your internal guiding compass.

But that inner wisdom, she doesn’t shout. She whispers. So you have to develop the practices to quiet the noise and hear what she’s trying to tell you.

And when you learn to listen, you will have an advantage in building a business that fuels your life.

But how do you actually put this into action and start listening to the voices for your intuitions more?

Take time. Sleep on it.

Notice when you're talking yourself into something. Your excitement to step into something new is awesome. That energy will serve you well. But long-term decisions also require your slow, thoughtful energy to tell you that this is right.

So ride the excitement and let it stay with you. But don't say YES yet.

Take some time to cool down first. No instant decisions.

Ask yourself these questions:

Learn how to tap into your emotions and feel your feelings so you can better hear your intuition. Don’t do this in a surface or touchy-feely way. Treat this seriously. This is CEO-level decision making.

Get honest with yourself. If something feels off in your body, in your bones—it won't work in the long run.

You HAVE to have a conversation about what happens if it doesn't work.

I learned this lesson with those brothers. But I didn't do it with my next partner. It wound up being fine, but it could have been a real mess.

Have the hard conversation before you start. It'll save you so much pain later.

And it’s the perfect excuse to slow the process down and test the relationship by having deeper, tougher conversations that will show you more about who they are and their values.

Make this a go-to-strategy for all your important decisions.

If you're not feeling a clear "Hell YES", it's a NO.

No maybes. No "let's see how it goes." No "it'll probably work out."

This essentialist philosophy will help you filter out most distractions that seem great but will eventually hurt you.

We live in a world of infinite choices. Which means there needs to be an extra special reason to say YES to anything. We need a “Hell YES”, not just a “YES”.

Trust feelings and emotions that come up for you.

If you feel a hint of “mmmmmm”, talk it out or resort to the default no.

That's it!

The biggest mistake I keep learning not to make:

Ignoring my intuition when someone doesn't fully respect me—or when something just doesn't feel aligned.

I've gotten better at catching it faster. And when I do catch it now, I actually listen.

(this is how I was able to confidently exit Wizly and choose a different path without burning bridges or hurting myself too much).

Your intuition is your competitive advantage.

Learn to listen to it.

With love and growth,
Kasey

PS– Do you have any decisions or questions you’re struggling with right now? I personally go through all the emails. Share some details by hitting Reply and get’s discuss some mental models.

As always, I’m obsessed with helping you win with/without me!

Let’s keep going ✨