My First Year as a Bootstrapped Founder

On May 1st, 2023, my Co-founder and I launched our app on the Shopify app store. Its now one year later, so its time I reflect on how that decision affected my lifestyle, happiness, and finances.

Choosing not to raise money

Before we decided to start a business, my Co-founder and I shared why we wanted to do this together, when we might want to exit, and why we might want to exit. We took those personally motivating things and wrapped a business plan around them.

Two problems quickly arose as it relates to taking funding:

1. Venture capital doesnt tend to invest in startups that dont want to grow to $100M+ valuations.
2. We wanted control over who we worked with, the ambitions of the business, and flexibility in how we would tackle this hard thing.

In a startup, theres much less patience post-funding. Once you start the treadmill of taking venture capital, it can turn into a count of how many rounds are left before they give up on you or a positive exit event happens.

We felt that the best structure is one that you dont have to take money.

How I made money

One way of looking at the chart is that we are growing quite nicely. An alternate interpretation is that it took us 6 months to make $1 of revenue!

While numbers are starting to look more sexy, there wasn't much to celebrate in the early days. This also meant that it took some time before I was in a position to quit my job.

And on the 14th of November I did exactly that - with $25k in personal savings and less than $2k in MRR. We had plenty of runway.

Things that surprised me

Looking back, I completely underestimated the time and emotional commitment it takes to get a startup off the ground, and you can see that in the numbers.

The change in growth rate once I went all in is hard to ignore.

This also meant that the task of very, very long hours started. Constantly working 16, 18-hour days wasn't something I anticipated. The hardest part has been trying to stop my personal life from bleeding dry as the business becomes all-consuming.

I've surprised myself countless times by being better at things than I thought. It turns out that I'm good at marketing, writing business strategy, and thinking about trade-offs and all of these things that you can't know if you'll lend well to without trying.

Turning points

My favourite turning point has to be winning our first paying customer, The Oodie.

As soon as I got off the call I jumped out of my chair and screamed. My housemates joined me in saying "Insane" over and over and over again.

Crossing $8k of MRR was another turning point. For the first time, it felt like some of the pressure and anxiety had been lifted. We were going to be OK.

Also, I'll never forget when my favourite clothing brand asked for a demo.

The best piece of work we ever did

On October 29th, I wrote a business plan. It's a document that describes the challenge that we are trying to address and the end-user scenarios that we are trying to solve. This attempts to explain to anyone who joins our start-up what we're trying to accomplish and what the strategy is or how we would achieve these goals.

I learned this from a founder I was fortunate to work under, Steve Pell , who describes the importance of it best:

"It not only gives context to the strategy today but also where it comes from and the impetus to the current thinking. It also holds us accountable for strategic drift. We do iterate on the strategy, but this document allows us to see if we have drifted too far away from the core objectives or problems we were looking to solve."

Why not build a $100M company?

I started with a lot of motives and values and thinking about who I was going to be in life. This thinking started very early - I remember being in high school and deciding I wanted to be a University lecturer when I was older.

Some of these things I want so badly in life that, when the door opens, I will make sure I get there.

I love what I do

People have asked me if I’m happy with my decision to quit and start my own company. The answer is definitely yes.

As someone who has always valued independence, I love being a founder. Financial outcome or not, this type of work is how I want to live the rest of my life.

Lessons learned

1. Save enough motivation for activity in your personal and social life.
2. Regularly reflect and get retrospective.
3. Appreciate how far you've come.
4. Love thy co-founder.
5. Have fun.

Goals for year two

What I hope to accomplish in my second year as a founder:

• Achieve $125k MRR.
• Guest lecture at a University.
• Hire and be able to take at least a 2 week holiday.