Getting acquired after 13 years of building

Igor Debatur is the founder of Uploadcare, a company making millions in ARR. And he just sold it to a strategic partner for a lot of money.

After spending the better part of two decades in the game, he’s learned a thing or two. Here are his learnings about building healthy businesses, acquisitions, and being the head honcho of a large organization. 👇

Focus on one product

James: You’ve been building stuff on the internet for 15 years. What do you wish you had done differently?

Igor: I would’ve never tried to run three companies at the same time, as my co-founder and I tried doing in the beginning. I don’t think it’s a good fit for most people — definitely not for me.

James: Why?

Igor: Every time I succeeded in one business, the other two struggled. They weren't at the stage when I could’ve hired someone to do the work — they needed a founder to work on them every day.

I was spread too thin. And I felt like I was failing all the time, even when one was doing well. The financial results were very unstable.

James: What would you have done differently?

Igor: I would have sold our web development agency on the first day we fundraised for Uploadcare. Or at least put it on hold.

It was scary, but I wouldn’t be scared now, knowing what I’ve learned.

James: Did you eventually set your other companies aside?

Igor: When we noticed that Uploadcare was taking off, I understood that I needed to focus on one product and put everything else on hold. My co-founder agreed and we moved forward. This was hard, but it was the only option.

I still think it was the right thing to do.

James: What happened to the other businesses?

Igor: I sold Whitescape, a web development agency.

RIDERS, a mobile app for action sport participants, had more than a million users, but I put it on hold.

James: Not an easy thing to do.

Igor: No, but it was a major game changer in my life. Also for my teammates and friends. After scaling back, I had more time both for work and life.

13 years to acquisition

James: Let’s talk about Uploadcare.

Igor: It’s a developer-oriented platform for file management and content delivery. I started it in 2011. My co-founder and I were encountering problems with uploading and file management so we decided to create an all-in-one solution that worked at scale.

James: It has come a long way since then.

Igor: It grew rapidly. 13 years later, we have clients like L’Oreal, PandaDoc, Buffer, and Zapier.

James: What’s your revenue?

Igor: I can’t share specific financial details, but I will say that we were able to drive a strong valuation for the business because of our high growth.

James: You sold it recently.

Igor: Uploadcare was acquired on January 16, 2024 by Tiugo Technologies, who also own brands like CK Editor, TinyMCE, and Butter CMS.

James: How did that happen?

Igor: We fixed our traction, and became break-even (again!) in 2023, so we were looking for ways to accelerate the growth.

We were used to working with VCs: larger investments, higher pace of growth, risky experiments, hiring tens of people at once, you name it.

James: Why not do that again?

Igor: The market has changed and if we fundraised from VCs, it would’ve made our cap table significantly worse. Other options were:

• Sell 100% to private equity, cash out, and ride off into the sunset

• Sell ~80% to private equity and keep running the company

• Get venture debt financing and accelerate our growth

• Find a strategic investor. Usually, those investors have another business that can benefit from acquiring a product; i.e. an integration, a potential for cross-selling, or some other creative option.

• Continue growing by ourselves. But that was too slow to be interesting.

James: So what did you do?

Igor: We decided to find a strategic investor — one who was interested in keeping the team. We’re proud of what we’ve built and we want to see how it will continue growing and evolving.

James: How did you do that?

Igor: To begin, I just started answering non-VC-type investors who reached out. It didn’t take long and helped me to understand the demand much better.

After speaking with my co-founders and agreeing that we were interested in exploring further, I doubled down. I started reaching out to more potential partners and started looking for an M&A advisory firm.

James: Was the firm helpful?

Igor: M&A advisors weren’t absolutely necessary, but they helped us to find more potential partners and to secure a better valuation. Their moral support along the way also helped a lot, so I think it was the right decision to bring them on board.

Ultimately, Tiugo looked like the best option and now, with everything signed, I can breathe and confirm it actually was the best option.

James: Why was Tiugo the right fit?

Igor: When I was an engineer, I used CKEditor and TinyMCE myself, and Uploadcare has plugins for both of these editors. And they have a working strategy that we understand.

I instantly felt it was a good fit.

James: Are you happy that you sold it?

Igor: I’m a gamer so I’ll put it into those terms: This was a “save game” and a “level up”. We achieved something, got the results, and became a part of a larger organization with more resources and experience.

James: And you’re still working at the company.

Igor: None of us were technically required to keep working for the company, but we liked the opportunity to continue scaling Uploadcare.

James: Any cons?

Igor: Frankly, I don’t see any cons for us, considering all the parameters: the market, cap table, the valuation. But it’s still the honeymoon period, ask me in two years!

And this is not a recommendation for you to sell! All situations are different.

Acquisition tips

James: What did you learn from the process?

Igor: So much.

• Don’t sell too early. Building startups is much harder than it looks: Overnight success is similar to winning a lottery. It’s more likely that you’ll need to spend 6-8 years to achieve a real return on investment. It’s a marathon. Always is.

• Don’t set selling the company as your goal. Your goal should be building a healthy business. Buyers are interested in buying healthy businesses; not promising ideas.

• Don’t sell too late. If the market is perfect and your valuation is skyrocketing, and you can see how you can get a life-changing amount of money today – don’t wait! I’ve spoken to at least four founders who missed their chances in 2021-2022 and now are struggling to sell for a lesser valuation. It’s easy to think that you can sell for more later. But do you really want to spend 2 more years and risk it if you can get a significant amount of money today? Remember to “save your game!”is

• Agree on the strategy with all the stakeholders. If one of the founders isn’t ready to sell, they will derail the potential deal and your morale, either knowingly or unknowingly.

• Get M&A advisors. You will pay 3-6% but you can get 5-15-25% higher valuation. They’re pro sellers; you’re a first-time seller. There’s a good chance that this will be worth it.

• Start getting ready for due diligence from day one. Your accounting, legal, compliance, etc. will all matter when you eventually sell. It’s much cheaper to organize numbers and all the paperwork in the beginning than to pay tens of thousands of dollars (not to mention the gray hairs!) to do a corporate cleanup.

• Delegate! Your M&A advisors, lawyers, even the buyer – all of them should be interested in helping you. Let them do their work!

• During the last weeks of due diligence, you’ll feel in the middle of a crossfire between lawyers and investors. Remember, it is going to end! You’ll survive.

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Organic growth

James: How did you grow Uploadcare to millions in ARR and, I assume, an 8-figure exit?

Igor: Uploadcare has always relied on organic growth and word of mouth as its main channels.

In-house file infrastructures tend to break at some point, and then developers start to look for better solutions. They Google, search Stackoverflow, browse reddit and other communities. We try to be there.

And our customers tend to recommend it to their peers.

James: So that hasn’t changed since day one?

Igor: It hasn’t changed. We just invest more in creating content

Now, with extra resources and so many experienced people in the Tiugo companies, we are aiming for wider publicity. And we’ll collaborate with Tiugo’s portfolio companies for cross-selling.

Leading a big organization

James: I want to know what it’s like to be the CEO of a big company. Do you still code?

Igor: No. Well, not for Uploadcare.

James: Do you miss it?

Igor: I do miss coding! It was an unbelievable feeling being able to create anything that I imagined.

James: And do you like what you do now?

Igor: I love working on vision and strategy – both tactical and long-term.

James: So that’s what CEOs of multi-million dollar companies do?

Igor: Basically. Imagine you’ve just found yourself in the middle of the ocean. The water isn’t too cold. There’s no storm. If you know the direction to the closest island, you’ll get there in an hour. If you don’t know the direction, you’ll drown. If you’re a strong swimmer, you’ll survive longer but the result will be the same.

It’s relatively easy to become strong at your domain of expertise, but in a big company, there needs to be someone to point out (and iterate) the top-level direction. And it’s hard to do both.

James: Sounds like you’ve gained a knack for that.

Igor: Thanks to my entry-level of ADHD, it’s hard for me to focus on one thing, but I usually have a good understanding of the overall picture and can navigate through various environments with plenty of variables.

As for strategizing, top-level ideas usually pop up in my head, I write them down, and at some point, I verbalize and structure them. Then, it’s teamwork.

This doesn’t mean I’m the only person bringing the ideas and deciding on the direction, but I’m the one who is responsible for initiating the discussion and achieving the consensus.

Prioritize business health

James: You mentioned building a healthy business. Tell me more about that.

Igor: I think that companies should focus on healthy businesses; not just growth or acquisition.

James: What makes a business healthy?

Igor: A healthy business has unit economics that work. Numbers should match. CAC<LTV, etc.

When you have an extra influx of cash, it’s easy to afford non-functional economics, but make no mistake: That’s a debt that will bring you down if you fail to fundraise next time.

Work-life balance at all stages

James: Speaking of health, you’ve been through all the stages of entrepreneurship — is work-life balance really possible in the early stages?

Igor: I think that maintaining a work-life balance is possible at every step of the founder's journey.

I want to live a happy life now, this exact minute. I don’t want to postpone it “until I make a 7 figure exit”, “until I build a unicorn”, or “until I buy a house”.

The same goes for my relationships – I want them to be healthy now. They can’t wait until I do “all the work”.

James: Well said.

Igor: It’s the main thing that I figured out in my 20s. I couldn’t verbalize it at that point, it just felt right. But now, I see how self-care, healthy relationships, and vast amounts of hobbies are actually an investment in my business.

James: How so?

I spend time resting. Then, when I’m rested, I generate better ideas. And I can spread my energy and motivation to my team. It’s a win-win.

Startups are marathons. One crazy push won’t be enough to build a successful business, but it can lead you to burnout. And 2-3 burnouts can irreversibly change you for the worse.

James: When were you the busiest?

Igor: Statistically, I feel overwhelmed about twice a year.

Things can and will go wrong. As a CEO I have to jump right in and try to help when that happens.

James: What does that look like?

Igor: It depends on what happened. It could be bringing in new resources, easing communication for team members, hiring the right people, bringing in mentors, just listening, etc.

James: And what happens to your work-life balance?

Igor: I usually start noticing that I work longer hours and can’t spend as much quality time with my family. I usually tell them what’s happening and when I think it’s going to be over.

James: Was the acquisition one of those times?

Igor: The last stage of M&A was definitely this kind of period. It was like being in the middle of artillery crossfire, waving the white flag and trying to calm other people who were also stressed. Luckily, I had been told that it’s always like this, so I was prepared.

I still got 7-8 hours of sleep, took long walks, and went to my climbing gym 3 times per week, as usual. These routines helped.

James: Sounds like you value balance, but you’re okay with hustling when needed.

Igor: Yes, you need to hustle and grind until your business is generating profits — and until you and your investors (if you have them) are happy.

But you don’t need to sacrifice a good night’s sleep, your hobbies, or your family.

If you do, after a year or two, your team will see a burned-out, unhealthy CEO without a family, who hates the world.

And even then, you’ll still have a couple of years to go before you sell your company. Probably twice that.

James: Where can people find you?

Igor: I'm building Uploadcare and you can find me on X.

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