Operator Philosophy

How I Choose Which Founders to Work With

It's not about the idea. It's about the person and whether you can actually help them.

Most advice about selecting clients focuses on fit and value. Find clients where you can create the most value. Work with founders whose problems align with your expertise. It's logical. But it's incomplete. The real question is not just whether you can help them. It's whether they'll actually implement the help. And that's determined almost entirely by the person, not by the problem.

I've worked with founders with bad ideas and great ideas. The outcome was rarely determined by the idea. It was determined by whether the founder was willing to do the work. A founder with a mediocre idea who's willing to implement feedback can build something meaningful. A founder with a great idea who's defensive about their approach will fail regardless of how smart the advice is.

Over time, I've developed some clear filters for the types of founders I want to work with. They're not about IQ or pedigree. They're about the qualities that determine whether someone will actually take advice and execute on it. If a founder doesn't have these qualities, I don't take the engagement, even if the problem is interesting and I could probably help.

Intellectual Humility

The first filter is intellectual humility. Does this founder actually want to learn, or do they want validation? A founder with intellectual humility knows they don't have all the answers. They're willing to be wrong. They're willing to hear that their core assumption is flawed and adjust. A founder without intellectual humility is looking for someone to confirm what they already believe.

This shows up quickly. In a consultation, I'll often point out something that contradicts what a founder believed. A founder with intellectual humility will say "huh, I hadn't thought about it that way, that's interesting." A founder without it will defend their position. They'll explain why I'm wrong. They'll rationalize why their assumption is actually correct. That's when I know the engagement won't work.

Intellectual humility doesn't mean the founder has to agree with me. It means they're willing to consider the feedback seriously. They might disagree with my interpretation, but they'll actually engage with the argument. They won't just dismiss it because it conflicts with what they already believe. This is rare. Most people are defensive about their ideas. That defensiveness is a blocker.

Accountability Orientation

The second filter is accountability orientation. Does this founder take responsibility for outcomes, or do they blame external factors? A founder with accountability orientation will say "we didn't hit our targets because I made the wrong hire and didn't course-correct fast enough." A founder without it will say "we didn't hit our targets because the market shifted and our investors were unsupportive."

Accountability orientation determines whether someone will actually implement feedback. If a founder believes their problems are external, feedback won't help. They'll thank you, say they'll think about it, and then do nothing because they don't believe they can affect the outcome. If a founder believes they control their outcomes, they'll implement because they understand that the outcome depends on their choices.

This shows up in how they talk about past failures. Do they analyze their own role? Or do they focus on what was done to them? I want to work with founders who will say "we failed because I made this specific mistake, and here's what I'm doing differently next time." That founder is coachable. The other one isn't.

Speed Of Feedback Loop

The third filter is speed of feedback loop. How quickly does a founder implement feedback and get back to you with results? A founder who immediately starts implementing and sends you results in a week is someone worth working with. A founder who says "thanks, I'll think about that" and you never hear from them again is not.

This matters because work is iterative. You give feedback. The founder implements. They get results. You analyze the results and give more feedback. The faster that loop moves, the better the outcomes. Some founders move at incredible speed. They get feedback at 3 PM and you hear results the next morning. Others move slowly. You give feedback and hear nothing for months.

Speed isn't about IQ. It's about urgency and follow-through. A founder who moves fast has a sense of urgency about fixing their problems. A founder who moves slowly either isn't urgent about the problem or isn't committed to the solution. Either way, the engagement won't produce results. I'd rather work with a founder of average intelligence who moves fast than a founder of exceptional intelligence who moves slowly.

Clarity About The Problem

The fourth filter is clarity about the problem. Does this founder understand what's actually broken? Or are they guessing? A founder who has done the diagnosis will send you materials that clearly lay out the problem. A founder who hasn't will send you vague descriptions and expect you to figure it out.

Some of the diagnosis is my job. I'm supposed to analyze their situation and identify what's wrong. But I need the founder to have done some thinking first. They need to have looked at their numbers. They need to have asked their customers hard questions. They need to have at least a hypothesis about what's not working. If they haven't done any of this, the engagement will be all diagnosis and no solution.

A founder with clarity will send materials and say "I think the problem is X. I've looked at our customer interviews and here's what I see. I don't know if this is right, but here's my thinking." That founder is coachable. They've done the work of thinking about the problem. I can build on that. A founder who just says "we're not growing as fast as we should and we don't know why" is asking me to do the entire thinking process. That's a much longer engagement and often not productive.

Willingness To Invest

The fifth filter is willingness to invest. Not in hiring me, but in fixing the problem. Does this founder have skin in the game? Are they willing to commit time and resources to implement the solution? Or are they hoping for a quick fix that won't require much work?

This shows up in how they talk about the engagement. A founder who's willing to invest will say "here's my timeline, here's what I'm committing to, here's how much time I can dedicate to this." A founder who's not willing will ask how much time it will take and seems hoping you'll say "just a few hours." They're looking for a magic solution that doesn't require much work. It doesn't exist.

I'd rather work with a founder who's willing to commit real resources to a modest problem than a founder who wants me to solve their entire business with minimal effort. The first founder will get results. The second won't, and they'll blame me for it.

Red Flags In Founder Selection

There are clear red flags that tell me not to take an engagement. The first is if a founder is shopping for opinions. They want me to validate what they already decided to do. They're not actually looking to learn. This shows up when they explain their strategy and seem annoyed when I ask questions. They want a cheerleader, not a consultant.

The second red flag is if a founder is defensive about their team or their approach. If they immediately explain why your feedback doesn't apply to them, or why their situation is different, they're not going to implement. Defense mechanisms are blockers to learning. I avoid founders with strong defense mechanisms.

The third red flag is if a founder is working on something they don't actually care about. Maybe they're building something because they think it will be fundable, not because they believe in it. That shows up as low energy around the work. That founder won't have the resilience to execute through the hard parts. I avoid them.

The Test Engagement

Sometimes I'm not sure whether I should take an engagement. In those cases, I do a small test. I give some feedback. I make a recommendation. I ask them to implement it and report back. Then I see if they do it and what happens. A founder who does the test and reports back honestly is someone I want to work with. A founder who doesn't follow up or gets defensive about results is not.

This test period is valuable for both sides. I get to see if they're actually coachable. They get to see if my thinking is actually useful. Sometimes I learn that I'm not the right person for this founder. Sometimes they learn that they're not actually open to feedback. Either way, it's better to figure that out in a small test than to commit to a full engagement.

The founders I most want to work with are the ones who pass all these filters. They're intellectually humble. They take accountability. They move fast. They've done the thinking. They're willing to invest. And they'll let me know immediately if my advice isn't working or isn't applicable. That founder will get better results, and we'll both enjoy the engagement. Those are the ones worth working with.

— Sam

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