Real Life Bootstrapping, Vol 1:  No Pay for 12 Months

This is the first installment of my new series "Real Life Bootstrapping". I plan to share valuable lessons I’ve learned from bootstrapping Firm Studio. The goal - providing practical guidance to current and should-be founders as you rise to the challenge of building something from the ground up.

I launched Firm Studio in April of 2022. 13 months later in May of 2023 I paid myself for the first time. How did I survive? My answer is laid out in two parts below.

First part: Personal Finances

Context matters and so does your personal finances when entering into a company building adventure. I spent the 15 years before launching Firm Studio bringing in relatively high income, limiting spending (living on less than 50% of take home), and benefiting from a few capital events. This has equipped me to live debt-free and worry-free about various monthly payments. I’ve skipped golf club membership, and opted out of fancy car purchases and high-end vacations. My family and I want for nothing and enjoy what we have. It's a far cry from how I grew up....I became an expert getting off the phone with creditors calling and asking for my parents and delaying the inevitable.

We’ve made a few commitments as a family when starting Firm Studio:

1. No debt ever
2. My wife doesn’t need to have an income (she homeschools now, hard work!).

Second part: Cash flow

Living without debt means I’m also very resistant to pulling cash from my own savings, so we must create some kind of cash flow for me personally on the side of Firm Studio. All Firm Studio cash went to building the team, making mistakes, and G&A.

Raising money was also off the table for me. That's another conversation/blog.

So, I needed real cash flow to live off of. What did I do?

• One real estate flip - I am not expert but I know them. I finance it, they do all the work we split the profit 50/50.
• I cycled my money via hard money loans at 2%/12% - 5 times, resulting in cash-on-cash returns in the 30% range.*
• I shorted Moderna stock because it's a terrible company and tripled my money in four months.**

That’s how I managed to run a company for a year without paying myself a dime from the company. Ideally, I’d like to never be in a position where I have to do these side hustles to make ends meet… I continue to dabble because I enjoy closing a deals and working with bit of risk.

If you’re a founder, it’s worth taking inventory of the assets that you have and how to best manage the costs of building a company. The less you need to pay yourself at the start, the more you’re able to invest in the early stage of your company.

Get strategic and get practical.

That's Vol 1. More to come!

*It's scary to do this unless you live, work, and play with the people who loan you money, and you MUST hold first position on the loan, i.e., no banks involved.

**I tried to invest more, but my trade got blocked for being un-American. It could have been a 90x. I had to teach myself how to do puts on Robinhood. I sucked at it, but I still had a good pop.

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