Playing a Different Game [SaaS Founder/CEO]

Lessons learned as a 2nd-time founder working with an exec coach

Published by [Client Name] on November 17, 2025

I did YC in [date] and started another company last year. I had rebuilt my life after [personal event] a couple years ago and felt like a new me on a new journey.

But as soon as some of the company pressure hit, a lot of my old doubts and insecurities would come up. I'd look at other founders and think, "Their company must be going great. Why can't I figure it out?"

That's why I got a founder coach. It was the end of 2024 and I had a lot of anxiety around making a decision to pivot. It really helps me to talk through things, to hear other people's experiences, and understand whether what I'm feeling is normal.

I needed a thought partner who had been in the trenches and understood the game.

I needed a thought partner who had been in the trenches and understood the game. Coaching has been great and the business has grown to 4 FTEs and 10xed MRR in just 6 months, but the most significant growth has been internal. Here are 7 lessons I've learned.

1. I'm not just building a new company, I'm writing a new story

For a long time, I didn't realize who I was building this company for. It wasn't for my girlfriend/fiancee or my current friends or the people I used to work with at [Post-IPO startup] or whatever. I was doing it for the high school kid in [Bay Area town] who saw everyone else go into the science and math olympiads and felt like he couldn't compete.

This company felt like my way of proving I could still win at the same game.

This company felt like my way of proving I could still win at the same game. The goal became getting that 1% wealth bracket, to validate that past self. Understanding where this motivation came from didn't make it go away, but it loosened its grip on my decisions. Now I can better see the difference between what the business needs and what I need to feel good about myself.

2. Your job isn't to be the player, but the coach and ref

When things get stressful, my instinct is to go into hand-to-hand combat mode and grind harder, send more emails, take more calls. But it's unsustainable. I realized my job wasn't to play the game, but to design the field where the game is played.

I had to stop and ask, "What is the highest-leverage activity?" It wasn't taking another random sales call. It was blocking off "creative time" on my calendar to work on the business, not in it. That meant building out our customer stories, refining our go-to-market plan, and investing in a strategy focused on advisor referrals.

3. Reframe losing as learning (especially in sales)

I used to get emotionally taxed by sales losses. A "no" felt like a personal rejection. Now, I see most of them as "not nows." I'm planting seeds. My job isn't to close a deal today—it's to be helpful and stay top-of-mind so that when their internal solution breaks, they think of me.

My job isn't to close a deal today—it's to be helpful and stay top-of-mind so that when their internal solution breaks, they think of me.

This mindset shift has been huge. It allows me to sell freely without being attached to the outcome of every call. I'm experimenting with pricing, messaging, and my approach, and conversations feel like data points rather than a reflection of my self-worth. It feels really good when someone who turned us down 4 months ago comes back wanting to get started right away.

4. You can't grind your way out of a capacity problem

For a while, my co-founder and I had different views on our biggest bottleneck. She thought it was top-of-funnel leads; I could feel that our delivery was starting to break. Our CS rep was behind, and we couldn't onboard new customers effectively. The truth was, we couldn't handle more growth. I hate spending less time on sales but recruiting another engineer and an ops contractor became the P1. It pushed our profitability timeline, but it was the right call. Better to grow slower than to let down the customers we already had.

5. On the other side of a hard conversation is clarity and alignment

I had to have a tough conversation with our first CS hire early on about performance expectations. My instinct was to avoid it because I want to be liked, and I worried she might quit (which would be a huge headache to work through). But people can't change what they aren't aware of. We laid out a 30-60-90 day plan, and it completely changed our dynamic. She's doing way better and now manages the ops contractor.

My instinct was to avoid it because I want to be liked, and I worried she might quit

Same with my co-founder. Instead of letting resentment build when she went MIA unexpectedly, I said, "I felt abandoned." It led to a deeper understanding and a stronger partnership. Running from these conversations kills companies.

6. I'll never win trying to play someone else's game.

We raised a small round for the company with mostly angels and small funds. For a while, I kept kicking myself for not getting a top tier investor like Greylock or Andreessen on our cap table. I thought that was the only way to get social proof, to be seen as "a hot company." I was jealous of the cool kids at the AI conferences. I was comparing our insides to everyone else's outsides.

The truth is, I was chasing the wrong game. It's not about getting into someone else's club; it's building your own. I realized that in selling to heads of finance, it's a boy's club. But instead of trying to break into theirs, I made my own. That's what our strategic advisor round is about—creating our own circle of trust with heads of finance who get what we do. It's social proof that's authentic to us.

7. Finding the right coach makes a huge difference

As a second-time founder, I knew I needed a different kind of support. My previous coach was great for life stuff, but I wanted someone who had been through the rollercoaster of building a company. Who understood the pressure of a pivot, the fundraising grind, and the unique insanity of the startup world. I needed a coach who could call me on my BS.

Working with Jason Shen has been that. He did YC back in the day, wrote a book about startup pivots, and understands how messy this all gets. When I come to him with worries and fires, he comes back with real talk and frameworks that ground me in reality. He helps me turn my stream-of-consciousness anxiety into clarity and next steps. We've got a long road ahead, but it's good knowing I have someone to turn to when shit gets real.

When I come to him with worries and fires, he comes back with real talk and frameworks that ground me in reality.

I first got to know Jason from reading his book on pivots. It was really specific in a way that made me think, "This guy gets it." But it was only after the first call that I asked myself: could I be fully honest with him? Could I show him all my embarrassing shit without worrying about my self-image? I felt like I could, and that mattered more than anything.

When we started, I had a lot of anxiety about this pivot we were making, about stopping sales to build product, about comparing myself to other founders. Logically, I knew competition wouldn't kill us, and big splashy rounds of funding don't guarantee anything, but emotionally, I wasn't there.

Ultimately the sales pause worked. We've gone from two people to four. MRR has 10xed in 6 months. Sales is breaking engineering, which is painful but a good problem to have, so now we're hiring again.

We've gone from two people to four. MRR has 10xed in 6 months.

But honestly, the numbers aren't even the main thing. It's the internal shifts. I'm learning to play a different game - building systems instead of just hand-to-hand combat in sales, creating an advisory board as a long term sales strategy. My relationship with my co-founder is stronger because I'm learning to own up to my feelings when I feel abandoned. I'm managing my team better, leading with empathy even when things are on fire.

Jason helped me reframe my thinking. We talk a lot about my actual goal of building a high margin business with lots of happy customers instead of just playing the never ending “bigger round” VC game. I just proposed to my fiancée and I don't want to be one of those founders who doesn’t work out or see friends or can't get excited about his own wedding.

I just proposed to my fiancée and I don't want to be one of those founders who doesn’t work out or see friends or can't get excited about his own wedding.

Jason calls my bluff and challenges my assumptions. He turns my stream of consciousness into actionable items. This whole startup thing is a game of prioritization, and he's been a crucial thought partner in figuring out what actually matters. It's not just about growing the business - it's also about making sure we're building something sustainable from the inside out.

Look, hiring a coach is a big call, and you should do what's right for you. But I figured it might help to share what it's been like for me.