Bootstrapping from ramen to $50K MRR, to acquisition, to regrets

A series of posts on my journey as a solo bootstrapped entrepreneur building a developer tool that sells to Airbnb, Apple, Dropbox.

When you build something with love, you don’t count your time and efforts, you’re not afraid to fail, and you’re becoming one with your project.

For many years, Paw was simply my second name. I was Paw. I never wanted to build my so-called “personal brand” because Paw was my brand. It didn’t even need to be that famous, but it had to look great, be high-quality, positive, and heart-warming. It made me feel proud, accomplished, and whole.

I started Paw when I was 22 years old, I’m now 33, which means this is the story of 1/3 of my lifespan. I feel that I learned pretty much everything throughout this journey. I probably 10x my programming skills, I learned to hire and lead teams, I gained business, accounting and law knowledge, I got into investing. I learned so much about who I am and who I’m not.

At one point, despite the growing traction and revenue, I fell out of love for my own startup, burned out, and became disillusioned by the world. I tried doing radically other things in my life. One thing led to another and I eventually sold Paw.

After a long period of idleness, regrets, self-questioning, I’m ready to start all over again. And one thing is clear, I’m gonna bootstrap. Indie is the way to go.

I thought that before starting anything new, I would privately write a post-mortem of this entrepreneurship journey to make sure I remember some key lessons, don’t forget what I did right, and avoid repeating some mistakes in the future. After reading (again) the inspiring stories of multiple bootstrapped entrepreneurs, I thought I should rather share mine publicly and take it as an exercise in writing and extraversion.

TL;DR

After multiple failed projects, I decided to build an app that I would surely use myself, learn in the process, make it paid from day one, and use it as an impressive line on my resume to land my dream job at Apple/Dropbox/Facebook/Google. Needless to say, looking back, I’m glad I didn’t have to work for these companies.

Paw’s first version was a simple API client where you query any API, view the response in a nicely formatted way, save, and organize your API calls. Back then, Postman, Insomnia, and the plethora of API tools we see today didn’t exist. Paw was initially sold on the Mac App Store for $9.99. And yes, I was giving away 30% to Apple.

I was too ignorant to do much marketing, but after multiple iterations, the product took off and made it to #1 on Hacker News. Going from a drop-off student ramen-eating lifestyle to getting $15K of sales in a single day felt surreal. That was the first inflection point when I realized Paw was now a profitable (little) company. I quit the side gig I had and focused full-time on Paw. That was an amazing time.

A year later, I hired my first team. I never hired anyone before, I never managed anyone, and I was timid and introverted. That was a stressful process, but the people I hired were wonderful, talented, and smart. I still miss them today. That was a wonderful episode.

That was the 2nd tipping point. As a team, we built Paw for Teams to enable collaboration around API projects and API descriptions. Paw was no longer a tool for individuals, it catered to larger teams and became a subscription-based SaaS. It took time to grow the SaaS revenue, initially individuals weren’t ready to pay monthly and we didn’t have larger companies join early enough.

I got burned out, questioned the meaning of my life, felt that working on a developer tool wasn’t enough, and I went on to volunteer for non-profit organizations. I learned a lot about myself in the process. But I thought that it was the end for Paw. I was ready to give up and move on. Yet, the user base kept growing and the MRR kept growing over the months and the years. We got subscription signups from Airbnb, Mailchimp, Slack, and others. No marketing, only organic, word-of-mouth growth.

That probably proves that I was a terrible businessman, a non-existent marketer, but a capable enough product manager and developer to build a profitable business.

I felt that I was in limbo, the company was then too good to give up, and yet I lost the motivation to keep building the product full-time. I was quite fed up with the API world and having Xcode, Objective-C and Swift filling up my monitor. I was stagnant professionally and I needed change in my life.

The folks at RapidAPI came at the right time and were interested in buying the business. The deal seemed good enough, the team was fun, and I was excited by the experience of selling, being part of a larger startup and start new chapter.

Two years went by working with the acquirers, effectively as a product & engineering manager/director focusing on building new developer tools to add to the company’s product offering.

As that wasn’t crazy enough, I co-founded in parallel a new startup, renting Teslas in Europe from a simple mobile app: scan your driver’s license and credit card, boom, unlock the doors and drive away. Beast is now a growing startup, I remain an advisor, investor, and fan, but I no longer work full-time with the company.

For about a year now, I’ve been taking a personal sabbatical, doing fun things like getting my private pilot license, and wondering what will be my next project. One thing is clear, it’s gonna be bootstrapped!

Sharing my learning points

I'm starting a series of blog posts covering my journey with Paw, each article focusing on either one page of the journey or a specific topic, among others:

• From failed projects to Paw becoming #1 on Hacker News
• Hiring my first team, applying to Y Combinator, dreaming big
• Taking my first sales calls with Airbnb, Apple, Dropbox
• My burnout and wanting to change the world, being disillusioned
• Growing to $50K MRR
• Selling the company to RapidAPI, from finding the right price, dealing with multiple top-tier law firms, drafting hundreds of pages of legal documents, dealing with taxes
• Working as (remote) Silicon Valley tech executive
• Launching an app-based Tesla rental business
• How I would do it if I were to start all over again

I love good stories. I think the big kids in us want to hear bedtime stories. However, if you’re an entrepreneur, you probably want to learn something new, so each article will end with:

• What I learned and can be useful to you
• What I think I did right and I recommend doing
• What I did wrong and what I think is the better solution

I’ll aim to publish one article per week. I normally don’t write that much, so it will be great a challenge for me. Subscribe and share the word!