BlogLeon Zucchini10 min read

Why We Left Corporate Jobs to Bootstrap a Startup

Why We Left Corporate Jobs to Bootstrap a Startup

In 2018 Rafael and I quit our corporate jobs to found Curiosity. This is why we did it and what we learned — for others facing the same decision.

In summer 2016, Rafael (@theolivenbaum) and I (@leonzucchini) were working in comfortable corporate jobs in Munich when someone decided to put us in a shared office.

Fast-forward two years and we’d quit our jobs to found Curiosity. It was an exciting but scary move, and people often ask us about it. How did we make the decision? Do we ever regret it? And so on.

In this post we’ll look back at common questions and things we wish we’d known back then:

  • Why we decided to leave: Finding a co-founder, coming up with an idea, deciding to leave

  • How we prepared to leave: Preparing to leave, making the final decision, gathering money

  • What happened then: Getting first clients, early struggles, achieving profitability

  • Looking back: Regrets, surprises, difference to corporate jobs, and what we wish we’d knew back then

Obviously, everyone’s journey is different. We offer ours in the hope it helps others considering a similar step.

Why We Decided to Leave (2016-2017)

How did you find the right co-founder?

We got lucky — for us it was the other way around. We were colleagues first, then friends, then co-founders. Nevertheless, there were some strong signs it was a good fit:

  • We had complementary skillsets (Rafael tech, me business)

  • We’d worked together already

  • As friends, we had a strong basis of trust

It’s hard to overstate the importance of trust for co-founders. You’re literally putting your financial future into their hands. There will be difficult times when you disagree. Trusting that your co-founder has your back is absolutely essential.

Rafael (right) and me(left) in early 2017

How did you come up with the idea?

We’d joked about founding a startup for a while, and one day I said to Rafael: “Don’t leave the company without talking to me first.” A few weeks later he went away on vacation and came back with an idea… and some website domains he’d bought just in case.

The original idea was broadly related to things we’d worked on in our corporate jobs. We’d seen projects struggle and fail because they were lacking the kind of tool we wanted to build.

That gave us some confidence that (a) there was a real problem, and (b) we knew how to solve it. What we underestimated back then was (c) can we sell it in a repeatable way?

What made you decide to leave your corporate jobs?

When we told our respective families about Curiosity, they looked at us like we were crazy. Leave well-paid, interesting corporate jobs for a risky startup — what on earth were we thinking!?

For me it was mainly about taking advantage of the opportunity: “How often do you have a business idea AND the necessary skills AND it’s with a friend?” I thought about it as regret minimization: I didn’t want to spend the rest of my life wondering, “what if?”

For Rafael, it was mainly about being his own master. Fewer meetings, no more project reporting, no more office hours. Just freedom to build things at his own breakneck pace.

Intermission: Curiosity

If you’ve got this far, you might be wondering what do we actually do at Curiosity. It’s changed over the years… so here’s the pitch.

Curiosity is a productivity app that gives busy people one place to search all their files and apps. That saves time and lets them avoid frustrating searches.

Curiosity connects with the tools people already use, including desktop folders and cloud apps like Google Drive or Slack. Unlike other search tools, it helps them get more done while always keeping their data safe on their computer.

Curiosity — the app we built

Curiosity is available as a desktop app for individuals (Windows / Mac) and also for small and large teams. You can get a free version from our website, and also a free two-week Pro trial (unlimited sources / search file contents).

If you struggle with too many files in too many places, give Curiosity a try. 🚀

How We Prepared to Leave (2017–2018)

How did you prepare to leave?

We spent most of 2017 working on Curiosity on nights and weekends. It was tough: Every evening we’d come home tired after a day in the office and open our laptops again. Every day for months.

The main activities (I remember) during that time were:

  • Building the first version of the product

  • Mapping out potential use-cases

  • Talking to our network to gauge interest

  • Figuring out how to found a company

  • Getting in touch with the local startup ecosystem

For a long time it wasn’t initially clear we’d actually go through it — and there were a few times we almost called it off. We were building and exploring, trying to decide if there was enough potential to justify the risk.

Evening work session in my kitchen (mid-2017)

How did you make the final decision?

As we got deeper and deeper into preparations, we were still excited about the idea. At the same time we were increasingly worn out from having two jobs and frustrated at the slow progress.

To avoid ending up in preparation-purgatory, we set ourselves a deadline to make a decision after the summer break in 2017. Our point-of-no-return was telling our respective managers we were planning to leave.

I honestly don’t remember the conversation where we finally made the decision. However, I do remember saying with a mix of excitement and trepidation: “OK, we’re actually doing this!”

First look at our shiny new knowledge graph technology (late-2017)

How did you know you had enough money?

We didn’t. We saved and prepared, and then hoped for the best.

We bootstrapped Curiosity, which means we didn’t raise VC money. That meant we had to focus on earning money from day one.

When we started, we each had enough savings for about six months. We were also reasonably confident about a first project that would keep us afloat for a few more. After that… we reckoned we’d figure it out.

It was a big risk. There was one month in summer 2018 when the company bank account and my private account hit zero. In the end our invoice was paid on time and it all worked out… but it was pretty scary. 😅

What happened then (2018-present)

How did you get your first clients?

We got our first project with our former employer. Of course it helped that they knew us, but we still had to win a competitive bid against large competitors.

Our second (small) PoC came from a friend whose team was looking for tech like ours. Then we met someone at an event… and so on, PoC by PoC, client by client.

We also benefited from the startup ecosystem and from people’s interest in AI technology: Events, networks, and accelerators were an important source of leads in the early days.

How long until you were profitable?

We were profitable from day one… because we didn’t have a choice. We had to figure out how to pay ourselves salaries.

When you’re bootstrapping, the question of profitability becomes one of how much you’re spending — on yourself and on investments in employees and technology.

We initially started with a lot of project business: Big-ticket build projects that would buy us a couple of months each. Then we gradually transferred those into recurring licensing revenues. It took us a couple of years to get to truly recurring “Ramen profitability” with the corporate accounts.

Our first office — in my living room

What were your initial struggles (PMF, marketing, …)?

It feels like we struggled with… everything. 😄

One big question was defining what the company was really about: We fell into the classical trap of wanting to build something for everybody (a generic NLP tool). On the product side that meant we were getting pulled in different directions — whatever the latest client wanted. On the marketing side it made our copy abstract and hard to understand.

We also struggled to find a scalable model to consistently generate leads: Networking worked well but didn’t scale, cold-calling was borderline unprofitable and we hated it, word of mouth was great but took forever.

In retrospect we were struggling with startup basics: Value model and growth model. Actually, I think it’s pretty normal: In my experience founding a startup means moving from one struggle to the next as you gradually figure things out.

Another unexpected challenge was Covid. Initially, we didn’t think it would affect us much, but then the innovation budgets dried up and IT departments turned inwards to deal with remote work. In 2021 we lost 20% of revenues and wrote a big loss. It wasn’t fun, but luckily we’d been cautious in the previous years so we had enough cash to survive.

Looking back (from 2022)

Did you ever regret it?

Many times. Especially in the early days, lying awake on Sunday nights when money was running low or projects were going badly. I think that’s normal.

But in the larger picture we’re very happy with the decision. We’re our own masters and we get to pick whom we work with (more or less).

In fact, nowadays neither of us can imagine ourselves on any other path. I don’t think we’d be happy for very long if we went back to corporate jobs with all the accompanying constraints and politics.

Curiosity in 2021 (photo by Max Ostermeier, courtesy of Wayra)

What surprised you?

I’ve been surprised at the emotional toll it’s taken on me at times.

As a founder, the buck stops with you. Being responsible for finding customers to finance salaries is not always fun, especially when you have no idea what you’re doing. It’s cost me many sleepless nights and I’ve not always been the best version of myself.

My best solution so far is to separate Curiosity from my own sense of self-worth. Realizing life will continue even if Curiosity fails, lightens the burden and allows me to view it as an interesting problem… even as I work hard to make it succeed.

What was the biggest difference to working in a corporate?

There are two big differences.

First, we can make decisions and start executing instantly. For example, we once interviewed someone on a Thursday and they started the following Tuesday. No committees, no presentations, we ordered a laptop on Amazon and that was that.

On the flip side, you have to do everything yourself. Want business cards? Design them. Want website analytics? Figure out how that works. We enjoy it because we’re constantly learning new things, but you have to accept there’s no job beneath your pay grade.

What do you wish you knew before you left?

It’s taken waaaay longer than we thought it would. I mean honestly, we started out dreaming we’d be millionaires in two years. 😅

Four years later we’re finally** back to the level of our corporate salaries… and that’s not even counting the opportunity costs. Very, very few people actually earn big bucks quickly, and 90% of startups fail in the first years.

Looking back, I’d recommend founding a startup for the adventure, for the flexibility, for other personal reasons. If you’re in it for the money, chances are you’ll end up disappointed.

Wrapping up

One day it hit me: “I’m strolling down a sunny street in the middle of the day and that’s totally fine. I decide how I spend my time now.”

Four years in, Curiosity is going great. We earn money from our customers, ❤️ we’re our own masters and we do whatever we want, wherever and whenever we want. That’s a pretty liberating feeling.

Rafael and I with his wife at a VivaTech event (2022)

We’re so grateful to all the friends and family who continue to support us. We’re also grateful to our customers and supporters, especially the early ones who believed in us when all we had were vague ideas and buggy software. You know who you are — you’re the best.

Curiosity continues to be a journey, there are ups and downs. But we’re happy that we made the leap from our corporate jobs — it’s who we are now.

— Munich, August 2022

Thanks to @ikoichi and Steffi for their input.

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