Bootstrapped startups and the shit I learn in therapy

This newsletter is a place to find transparent, thoughtful advice on building bootstrapped companies and living a fulfilling life.

Most of the content in tech makes me want to groan and roll my eyes. I have no interest in hustle culture, optimizing my morning routine, or building the next unicorn.

I build companies because I like the autonomy, the creative challenge, and the financial upside. I want to make a good living, leave the world a little better than I found it, and have as much free time as possible to pursue passions outside of work.

I think a lot about (and struggle with) what enough looks like, how much time to devote to work, how to have a healthy relationship with money and possessions, the connections between ego and entrepreneurship, and how to be mentally healthy.

If that sounds interesting and refreshing to you, you should join more than 6,000 other readers!

What to expect

I send an email once per month, here’s what you’ll find in each issue.

I’ll share what I’m reading, watching, listening to, and learning about as I bootstrap my next company. I look for content that is thoughtful, transparent, and puts value on things other than just a checking account or cap table. I try to pull from a diverse range of authors whenever possible.

1 essay from me

The only way I know how to write something interesting is by drawing from personal experience. I get super transparent about the ups and downs of building bootstrapped businesses, share stories from my personal adventures, musings on life, and lessons from my therapist.

I love to spend time on the internet reading articles, watching youtube videos, and listening to podcasts. I also think it’s important to for business and for life to be a well-rounded human. So I wrap every issue with 3 links that have nothing to do with startups.


What’s with the name?

I want this newsletter to be a refreshing break from the typical tech-bro hustle culture stuff that’s out there. Also one of my hobbies is making classic cocktails, and a gin and tonic was my go-to cocktail for a long time.

Are you anti-VC?

Not really. VC doesn’t feel right for me and my goals. And I think in general a lot of companies raise VC that shouldn’t, and then get put on a trajectory that doesn’t make sense. But if you need to do something really hard that isn’t going to make money for a long time, or you want to build a massive consumer company, VC is necessary.

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