Coaching might just be one of the most effective ways to level-up as a founder.

I first got interested in coaching hearing my roommates Kishan and Anand talking about it. I was skeptical at first. I've always been a "I can figure it out" type of guy.

In 2023, we joined a founder's community called Climate Collective. One of the benefits for members is free coaching sessions. I ended up doing 4 sessions across 2 months with a coach called Jimmy. It wasn't anything life-changing, but I was starting to get it.

Earlier this year, things were starting to heat up at Streamline and I proposed getting coaches for both me & Helena. The way I framed it was:

It's one the few things that has a fixed cost but unlimited upside. If we want to be better leaders, this is something we should take seriously.

We continued to talk about it, until one particularly stressful week where 2 major customer pilots made the entire world feel crashing down. It was then that we decided we would explore this.

One of our angels introduced us to Lindsay, and the steep price initially gave us pause. But the first session was so amazing that I knew that I would become, in her words, "unrecognizable".

We ultimately decided this was an investment in us becoming better leaders and committed to her minimum term of 6 months.

Survival patterns

The first few sessions were very eventful. We spoke at length about my earliest childhood traumas. I cried tears that I didn't even know I had about what had happened then. I learned how to "re-parent" myself.

After breaking me down and understanding my core beliefs & motivations, we started to move into some more tactical stuff.

Something I used to do quite frequently back then was getting really worked up during internal meetings. Speaking faster. Taking control of the meeting agenda. Sucking out all of the oxygen in the room. Whenever this happened, I can always feel my heart racing.

When we broke it down, I realized that I was "overefforting" because I was scared to lose control of the meeting. And I took over meetings other people ran whenever I felt like meetings weren't going in the right direction.

A lot of this sounds mico-managey, but what's interesting was that this wasn't my style at all outside of meetings. I think it was knowing that the meeting ended at a certain time that created artificial urgency.

And this was the first survival pattern we identified - overefforting.

It was that whenever I would become stressed, I would seize control of the situation and take over like a commander in war. Urgency is important, but behavior like that doesn't build a lasting company culture and ultimately drives away smart people with good ideas.

Once she pointed this out, it was clear something had to change.

Slowing down to move faster

What we tried a new mantra - slow down to move faster. At first I didn't get how this could work, but I was intrigued.

The first thing she recommended me trying was to sit in a meeting and not say a word until the very end. "This would drive me crazy" I remember telling her.

But I tried it and things ended up being pretty ok. Some middle parts of the meeting were messy, but the group got to the same conclusion that I had formed 10 minutes into the meeting. But it was even more powerful because everyone came up with that conclusion themselves.

Then I tried to apply this to other things.

We used to just ship things directly in response to customer feedback, and there wasn't really a system for documenting how we were going to approach bigger features. This worked for a 3-person company with 1 founding engineer, but it didn't work for 2 more engineers and a designer.

One day, one of our engineers wrote a spec for a project. He circulated it internally, collected feedback, and broke ground on the project. When asked about it, I was initially reluctant about baking this into our process. But after seeing how successful this project was end-to-end, we decided to try it.

What ended up happening was exactly like the mantra said. Projects felt a little slower to get off the ground initially, but once we got better at writing & reading specs things just sort of took off.

We were able to ship much more quickly and confidently. PR reviews were easier because we had context on the overall direction. Product features that were delivered mapped 1-1 to customer outcomes. There was no doubt - we were moving faster.

After these experiences, I started to apply this to almost everything. I found that being able to slow down brought me to the present moment more and lent itself to listening - truly listening.

And being able to listen like that allowed me to see beyond surface level concerns to core problems. Slowing down gave me the clarity, and once I was ready I would execute swiftly.

Other things I learned

It's hard to write about this because I know a short post like this cannot the year I spent with my coach any justice. Instead of feeling the need to explain the backstory behind everything, I will instead just give brief summaries so you get a sense of just truly how transformative the experience was and how wide-ranging the topics were:

• I learned that my core fear is being alone. More specifically, the fear was that people would leave me if they thought I wasn't good enough. It explains the impostor syndrome and a bunch of other things that I get nervous about.
• I learned that my role growing up in the family was the fixer and that I started the company to fix the same problems I couldn't fix in my family. I was central to the family dynamic yet powerless so I put myself in a position of power in the company so I can fulfill this role.
• I learned that asking with curiosity is very different from demanding answers. Related to this, learning how to approach situations with genuine curiosity.
• I learned that getting involved does not mean getting in the way
• I learned how to take radical responsibility of everything in the company
• I learned how to redefine intensity and not be an asshole
• I learned how to love myself

Closing thoughts

Ultimately coaching was one of the most transformative experiences from starting the company. If you are hesitant about it because of the price, I get it. But trust me, it was worth every penny.

Ultimately you raise a lot of money to recruit the best team, and that includes yourself.

Your growth means that a better version of you shows up to work. It is your job to make sure that this can happen or you won't scale with the company.

And in some ways, founders set the ceiling for the rest of the company. If you aren't growing as much as you think you can be as a person, it's limiting the rest of the company. Or put more positively - there will be ripple effects for everyone in your life - company, family, friends - if you can work on yourself. It can feel indulgent and selfish, but it's not.

One more closing thought

Winning in startups requires a high performance mindset. If business were a sport, then startups are the olympics.

You are an elite athelete. Starting treating yourself like one.