Trust your gut

Hello founders,

Book Update - I just spent two days locked in a recording studio narrating the audiobook! It went well, but holy hell was it exhausting - turns out reading your own book aloud for 9 hours straight is harder than writing it. Pre-orders are live, and I'm putting together a workbook that walks you through the entire playbook step-by-step. This guide is exclusive to pre-order folks and you'll get it before the book releases. Grab your copy, send me the receipt, and I'll add you to the VIP list.

An experiment - I tried something different this week, instead of sitting down and writing, I wrote an outline on a post-it, recorded it, and then used the transcript as my initial first draft of the newsletter. You can check out the video here. Let me know if you like this style.

Thirteen years into this entrepreneurial roller coaster, I've learned something crucial: the very instinct that made you crazy enough to start a company is probably the same one you've been systematically trained to ignore.

Think about it. You had the conviction to quit a six-figure job and go to zero income. You believed something so deeply that you were willing to bet everything on changing how people use CRM, or prospect, or whatever big problem you're tackling. That takes a special kind of insanity - the good kind.

But here's what happened to me, and I suspect it's happening to you too.

The Slow Erosion of Founder Conviction

As I built out our team and hired smart executives, I started doing what all the mentors told me to do: "mature," "grow up," "become a professional CEO." I began deferring to other people's expertise and trusting myself less.

Every time we had a strategic decision, I'd weigh my gut instinct equally with everyone else's opinion. I believed in flat organizational structures and collaborative decision-making. Sounds smart, right?

Wrong.

What actually happened was my reliance on intuition - the thing that made me successful in the first place - dropped precipitously. I went from founder mode to professional manager mode, and it killed my company's momentum.

The result? More than a couple of years where I genuinely didn't love running Predictable Revenue. We had good people and good customers, but I wasn't happy. I didn't have high enough conviction to break through the inertia of "this is how we've always done it."

The Confidence Roller Coaster

Every founder experiences this. Even Sam Altman (see rule 36, “the days are long but decades are short”) has days where he feels like the king of the world and days where everything seems ready to explode. You're not alone in having these swings between supreme confidence and riding the struggle bus all the way home.

The problem isn't the ups and downs - those are inevitable. The problem is when low confidence leads you to stop trusting the very instincts that got you here.

Two Books That Changed Everything

When I was struggling to find my strategic footing, two books completely transformed how I think about decision-making:

Good Strategy, Bad Strategy by Richard Rumelt showed me I'd never actually done anything strategic. All our quarterly planning and annual goal-setting were just "pick a number and make up math to get there." We had fancy names and big hairy audacious goals, but zero strategic thinking.

Rumelt's framework is deceptively simple:

• Situation: What's actually happening? What position are you in?

• Diagnosis: Why are you in this situation? What's the real crux?

• Guiding Policy: How will you get out of this situation?

• Coherent Action: What are the specific next steps?

This isn't something you can rush through. The last time I ran this with my exec team, we spent nearly an entire day just on situation and diagnosis. But that deep thinking revealed strategic blind spots I'd been missing for years.

How to Decide by Annie Duke (yes, the poker player) taught me about decision quality versus outcomes. You can make great decisions and still have bad outcomes - that doesn't make you a bad founder.

Duke's insight hit me like a ton of bricks: she didn't want to be an "outcomes collector." She wanted to follow a good decision process. When she played a poker hand correctly but lost, she was still a good poker player.

The same applies to you. Your last sale, your last customer interaction, your last product launch - none of these individual outcomes define whether you're a good entrepreneur.

From Beliefs to Bets

Here's the game-changer from Duke's approach: when you write down your assumptions, biases, and probabilities, they transform from beliefs into bets. Beliefs are internal and hard to challenge. Bets are measurable and testable.

Her six-step process centers on building a living decision tree using what she calls the 3 Ps - Preferences, Payoffs & Probabilities:

1. List possible outcomes - Sketch a "decision multiverse" showing every branch that could unfold

2. State your preferences - Attach what you value (money, time, reputation, happiness) to each branch so trade-offs are explicit

3. Estimate probabilities - Make your best guess for how likely each outcome is, using both inside knowledge and outside base-rates

4. Compare upside vs. downside - Ask whether the reward justifies the risk; get precise where it matters, stay loose where it doesn't

5. Iterate & expand - Loop back through steps 1-4 for unexplored options or when new information arrives

6. Commit, then check - If no single piece of additional data would change your decision, decide, document why, and move on

When you combine this with Rumelt's strategic thinking, you get something powerful: a framework for trusting your gut while making high-quality decisions.

Why This Matters Now

I'm not telling you to ignore your team or make unilateral decisions. I'm telling you to remember that you're the expert on your customers and your market. You've done the work. You understand the gap you're trying to fill.

Where I failed was communicating my instincts to the team in a way they could understand and get behind. I let imposter syndrome convince me that everyone else's opinion was as valuable as mine on core strategic questions.

That's not true. As the founder, you have context and conviction that others simply don't have. Your job isn't to be democratic about vision - it's to be right about where you're going and compelling about why others should follow.

The Turnaround

Six months ago, I made the scary decision to shut down our outsourcing business and pivot to coaching founders. It was terrifying, but following this strategic framework gave me the conviction to push through the inertia.

The result? I'm 10x happier running my company today than I was a year ago. The team pulled through, and we're building something I genuinely love again.

Your Next Move

Here's what I want you to do:

1. Buy these books. Seriously. Good Strategy, Bad Strategy and How to Decide will change how you think about running your company.

2. Document your biases. Write down what you believe about your market, your customers, your competition. Transform those beliefs into testable bets.

3. Run the strategy framework. Spend serious time on situation and diagnosis. Don't rush to solutions.

4. Trust your gut, but verify it. Your instincts got you here. Don't let them be drowned out by committee thinking.

You started this company because you saw something others didn't. That vision, that conviction, that willingness to make big bets - those are features, not bugs.

The market needs founders who trust themselves enough to make bold moves. Your customers need you to have conviction about where you're taking them.

So trust your gut. But make it strategic.

You've got this.

What's your experience with balancing gut instinct and strategic thinking? Hit reply and let me know - I read every response.

Collin 

PS - I’d love your feedback on what else I can create for you all as a reward for pre-ordering the book. Here are a few ideas: exclusive pre-order book club, video course to accompany the workbook, a physical copy of the workbook (madlibs style), and access to a GPT with the full content of the book. Hit reply and let me know.

PPS - if you love audiobooks and can commit to a quick turnaround, I’m looking for a few people to listen and help me find any issues. Hit reply if you’re interested.