Pear Shadow turned three this year. I wrote the first invoice in 2020. Now we ship apps used by millions. Here's what happened.
2020 — The Beginning
I started Pear Shadow in 2020. As a legal entity to work with Tinybeans. Right after the COVID induced layoff. Right after 400 emails.
It wasn't a grand plan. It was survival. I had a contract, some savings, and no idea what I was doing.
First client: a US social network. Android app. Brown field of Java and Kotlin. I'm the 10th engineer on this codebase in almost that many years. Legacy, the works. I billed hourly. I undercharged. I overdelivered. Sometimes the other way around, but I learned a lot working with incredible people: engineers, product and project managers and CTOs.
Second client: a UK telco. Clean code, great work, terrible pay terms but a step forward. Something new, different and again amazing people, so much to learn from them, their product and how the tech world works.
Third client came through a connection. Then fourth. By the end of 2020, I had four clients. All remote. Two in the US, two in Europe. I was doing the work of a small agency by myself - or close to that.
2021 — The Hiring Mistake
I hired too early. That's the mistake most first-time founders make. I thought "more people = more capacity = more money." Also I trusted that everyone wants to learn hard skills. But some don't, and we had to part ways.
I hired a junior Android developer. Solid coder. No experience. No mentorship from me because I was buried in client work. The client complained. I apologized. I fixed it myself. I paid the junior anyway. And this cycle repeated. With other engineers and other clients.
Three times in 2021 before I learned: hire when you can teach, not when you're drowning. Mentor your people as if it was a classroom filled with your own children and their future depends on you. Sounds grandiose and magnificent but it's extremly hard to juggle the CEO, the mentor and the engineer so that all get equal equity and all perform at the same time.
But I was lucky to find some incredible engineers that are with me to this day. Two engineers who actually made the work better. They learnt the craft and the soft skills at lightning speed and helped me push the needle forward. And survive.
The team grew to four by end of 2021. Remote but we had an office where we loved spending time together, obviously. EU and US time zones. Slack, Notion, GitHub. Demos, invoices, Zoom calls. The usual.
2022 — The Growth
Revenue doubled. We started taking fixed-price projects and retainers. Something that looked like a real business. I was still the CEO for some, customer success to other, mentor to my team and an engineer to some of the clients.
But here's what nobody tells you about bootstrapping: you make money, but you don't make profit. Every dollar goes to payroll, tools, taxes. I paid myself last. Sometimes not at all. Hated those months. I was happy that we survived and got to see the next 1st in the month, but not getting paid stung. It always does.
We had an unpaid invoice situation in Q2. A quite large sum for a small agency like that. Pocket change for others probably. The client "forgot." Then "reviewed." Then "processing." For three months, I didn't know if we'd make payroll.
We made payroll. Barely. The client paid eventually. Never worked with them again. Thank God.
The overtime was brutal. I'm not going to sugarcoat it. 14-hour days. Weekends. Sprint deadlines that I underestimated. Clients who wanted "just one more feature" for the same price. Free work. FREE WORK. Yeah, from the bottom of my heart I wanted every client to succeed and every project to be successful. So I gave away free hours if they couldn't afford them in hopes they will one day. I made every single mistake I could and some more.
But the team stayed. That's what mattered. We shipped apps. We fixed bugs at 2 AM together eating pizza in the kitchen. Laughing at the delivery guy who asked what kinda job are we doing at this hour and I said: "IT. But the CEO is a problem". We complained, then laughed, then fixed it. And repeated the cycle many times over.
2023 — The Maturing
We're at seven people now. Juniors, seniors, designers. Still remote with an office.
The junior situation is different now. I can mentor. We have onboarding. We have code reviews. We have a culture that's not just by default by also in writing. And we teach our ways to the ones coming after.
The clients are different too. We're picky now. We negotiate terms. We have lawyers (sort of).
We had a bug once — one of those UI glitches that only appeared on certain Pixel devices. The client was furious. The user was furious. I was furious. We spent three nights debugging. Found it: a rounding error in a custom view. Two lines of code. Three nights.
But we also get praised. A CTO told us we were "the best mobile team they've worked with." A PM said our code review process was "actually useful." A CEO sent a thank you note after we shipped early.
Those moments make it worth it. They fueled us to do it again. To be the best team wherever we land, learn from them but also teach them.
The People
I wouldn't be here without my own mentors. A math teacher who taught me persistence. A teaching assitant that taught me when to turn off my pride and prejudice and just work. A CTO who taught me to be cool calm and collected in the most dire situations. A founder who showed me how to price. A lawyer who helped with contracts. An ex-colleague-turned-fellow-CEO who answered my stupid questions at 11 PM.
The team, too. The ones who stayed through the hard times. The ones who pushed back when I was wrong. The ones who made the work fun even when it was hard. The ones that grew and helped me grow.
Clients became friends. Friends became clients. The network grew organically, the only way it should.
The Take
Three years is nothing in business. We're not successful. We're not failed. We're building.
Would I do it again? Ask me in ten years.
Would I change things? Absolutely. Hire slower. Price higher. Fire faster. Trust my gut more.
But the chaos taught me more than any business course ever could. Here's to year four.