Josh Swerdlow
AboutPostsEntrepreneurshipRelationshipsClimateHobbies

Author: josh_swerdlow Date: December 19, 2025 19:11:56

EntrepreneurshipRelationshipsSelf

Founding-Founder Alignment

One of the constants in life is that you will always make mistakes, so here I reflect on both the good/bad easy/hard fun/scary lessons I learn. I do NOT try to find a solution, but rather a different path forward with my new knowledge. When I try to find solutions, I tend to believe that I cannot make the same mistake again. This space allows mistakes to exist so long as I continue to try different paths rather than claim solution over them.

What Happened

I've been trying to start a company for a year and somewhere in the middle I got disillusioned with doing what I thought I needed to do to start a company with what I felt was helpful to the company. This disillusionment came from chasing investors/investment.

It was until I read through Rob's work did I snap back into place and only a few weeks after that did I realize, that most of Rob's tactics were how I started!

What I Noticed About Myself

I'm not going to write about all the ways chasing investors negatively impacted what I valued my mental model. Instead I want to note a negative feedback loop caused by it. Chasing investors was stagnating my company, but this negative feedback loop was draining my ability to want to try anymore.

I found that while larping as a co-founder, I felt hard pressed to 'show up' at founder events or with friends because I felt I wasn't making progress. I felt that way because even if I was doing what I thought I had to do, deep down I felt mis-aligned.

I thought this was the way to found a company and I was simply uncomfortable with it so I was what was wrong -- not the system. With that firmly locked, I pulled back from events that would give me community for fear of feeling like I was 'just for show' (ironic huh?). I dropped contacts with founders I would otherwise have talked to and this led to isolation. Obviously that just makes dealing with starting a company even harder because you don't have founder friends to commiserate with.

What I’m Sitting With

I've found out through this process that I am a big 'fix a problem for a customer' type of founder and not a 'pitch an idea to change the world' type of founder. I foresee myself being very hard pressed to fundraise, but that's a problem I'll be proud to earn.

I've found that there are ways that you as a founder have to align with 'how you want to found'. My instincts initially led me down the path of focusing on the customer and not giving a crap about investors, but I got lost in the sauce and didn't keep my nose to the ground. That spiralled into my downfall. I think I only would have figured this out because I had to sit with the 'other way' for a while and now I'm confident that I don't want to do it that way.

How I’ll Hold This

If you don't ever stop trying to reach out and talk to customer because you truly love them and want to see their problems solved, then you'll never not be proud of your work -- even when you are going the wrong direction and just don't know it yet.