The most expensive person in your company

"I know it sounds expensive, but I think we should spend $10k for a sales coach," I told my cofounder back in 2023.

Not long before this, we'd shut down Playhouse, the consumer real estate app we got into YC with, and pivoted into building an AI product for businesses with Sentiyen. After getting beat up in B2C for two years, we decided to try the "safer" B2B route and started selling a custom chatbot maker to course creators, coaches, bloggers and companies. These were "ye olden days" of AI and gpt-3.5, but we had enough initial traction that I felt we were ready to move from discovery to scaling up sales. But how?

Neither of us had done B2B software sales before. I went back and rewatched some of the sessions on B2B from our batch (that I completely ignored because our sexy app would surely sell itself), but I wanted more. I saw on Bookface a recommendation for a sales coach and booked a call (Darren at Rampd is great btw). The ask felt really high. Already feeling down from our two years of failing learning and in runway preservation mode, it was hard to justify a big sum like that on something that a part of me said I should be able to figure out myself. A simple model could show me some ROI scenarios, but that gave no additional confidence.

Instead, I thought back to other times I've invested in myself when the return was unclear. And how it's ultimately a bet on myself - not on the sales coach, but on me - to make the most of it no matter what happens. The financial commitment would simply increase the pressure for me to really perform at my best and everything else is a bonus. That's how I ended up seeing it and signed both of us up.

In the end, the product didn't succeed, but we learned that much faster, and the skills and confidence gained were something we would keep and continue to build on.

If I zoom out, the startup itself was investment in me. Every hard conversation, every hire, every pivot, every fire drill - I was learning and growing whether I realized it or not. The question was whether I was being intentional about it or just white-knuckling the whole ride hoping wisdom would show up on its own. How I handle conflict, how I manage pressure, how I make decisions under uncertainty - that's the part I get to keep regardless of what happens to the company.

The most valuable asset

I heard something similar from the founders I interviewed last fall (data breakdown at the end). I learned about their initial skepticism and what got them over the line, but I also heard how they spoke about the value they got out of it. It was rarely in dollar terms. (Although I think one could apply PG's Equity Equation here too)

Tristan¹ was building his first startup and assembling "a killer team under the gun." He'd never managed anyone before. His early hires had far more impressive resumes than his. The imposter syndrome was going through the roof (I've been there too).

He found a coach through a workshop, someone that matched what he was looking for: a sensei, a guide to leadership, rather than a boss with no context. They ended up working together for over four years, through cofounder conflict and breakup, and eventually into his next company.

The way he sees it: doing a startup brings a ton of pressure, and if you do well, there's only more. You're the highest leverage person in the business. Coaching is a catalyst for learning under that pressure. "A good coach can 10x what you learn from the same amount of stress." The stress is the tuition you're already paying. And the lessons that came out of it, he said, changed how he relates to life itself.

Calvin raised a Series B and his investors offered to pay for a coach. He went in wanting tactical CEO help. He was surprised by how psychological it actually was. (Even his sales coach, he later discovered, was 50% psychological.)

The first 360 alone was worth it. As it turned out, different parts of his organization saw a completely different CEO depending on the context. His coach helped him navigate the cultural issues, his conflict avoidance, and the transition from fixer to company-builder. "At the startup, you're the most expensive person," he told me, "not just the dollar cost, but the impact. If a coach can make you 20% more effective, it's a really good ROI."

Michael's company had just raised their Series C and one of his investors introduced him to a coach. He had a strong network already, but saw value in having someone with full context who showed up consistently. Soon he had a good test: an exec who wasn't working out. He already knew the answer. But the situation was messy and the conversation felt impossible (sound familiar?). His coach helped him be at peace with what he already knew, and he had the conversation without the emotional rollercoaster.

When I asked him about ROI, he didn't even try to separate it. "Lots of valuable things I'll carry out of this experience irrespective of what happens to the company." Relationships, setting expectations, navigating change. The growth and the role are not separate.

Rather than milestones and achievements, most founders kept coming back to the value of coaching being about who they became along the way². Which made me reflect on the frame of the ROI question to begin with.

Player of infinite games

There's an idea I like from philosopher James Carse that I keep coming back to: "A finite game is played for the purpose of winning, an infinite game for the purpose of continuing the play." An infinite game has no defined endpoint, no permanent winner and the rules can change at any time.

Simon Sinek extends this idea to business, pointing out that there isn't actually an endpoint where you win. But in startups, we tend to subtly reinforce this by celebrating startup "exits." I'm all for celebration, but it's also important to remember we're playing in an infinite context. Your startup can be a means towards some finite end, or it can be the board on which you play the infinite game. The most important variable in that game is you.

The prank of consciousness is that we usually don't notice the player. It's like being inside a blind spot. There's no game without you and yet, thanks to the blind spot, we overlook ourselves as the most important asset in our own company.

Sinek suggests having a "Just Cause" - a powerful vision of a future that's not yet here that pulls you and your team forward. I see investing in your own growth as the multiplier. Because the depth of cause you can hold is a function of who you are.

So if you're already paying to play this game with your time, money and attention, then what, or perhaps who, are you building that you get to keep beyond the current horizon? And what does victory look like in your lifetime?

If you've read this far and are curious about what's next, I'll use the next post to talk about what I've learned so far about choosing a coach, the common traps and most of all, how to be a good client.

1. All names have been changed to protect privacy.
2. Not all the engagements were a success (see below). About a quarter of the founders I spoke with had at least one coach that didn't work out, and 10% never found a good one. More on that in the next piece.
3. If you're hitting a ceiling in your leadership and would like to have a chat, shoot me a DM.

By the Numbers

29 YC founders interviewed

Outcomes

* Negative initially and positive after finding a new coach.

What triggered coaching
(multiple triggers allowed)

Initial skepticism about coaching

How coaches were found

What founders prioritized in coach selection
(multiple criteria allowed)

How founders framed ROI
(multiple framings allowed)

Worked with more than one coach: 14 of 29 (48%)