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To sell or not to sell — that’s the question many entrepreneurs ask themselves when their startups manage to beat the imposing odds and achieve financial success. Sell too soon, and you may lose out on growth that’s yet to come. Wait too long, and you risk cashing out after your business has already peaked.

At one point, Andrew Gazdecki belonged to the second of these two cohorts. “I held on because I was attached,” he says of his first company, Bizness Apps, which he sold in 2017. The company, a publishing platform that helps businesses develop mobile apps, began life in 2010, riding the smartphone revolution kickstarted by Apple. When, years later, Bizness Apps began losing customers, and continued losing customers, part of Gazdecki knew it was time to sell. And yet he waited.

Although, in retrospect, Gazdecki did not pick the most opportune time to sell, the experience would inform the rest of his career. Hoping to make the process of selling — which was as bureaucratically cumbersome as it was emotionally draining —  easier and more accessible, he went on to create Acquire.com, a digital marketplace for buying and selling online businesses that has seen more than 2,000 sales worth upwards of $500 million since its founding in 2020.

Underpinning both Gazdecki’s career and Acquire.com’s philosophy is the belief that selling a company is not an end but a new beginning. Not a closure but an opening up of fresh opportunities. 

Here, Gazdecki joins Big Think for a chat about when to let go and when to hold on, the dangers of overestimating one’s own ability, and why sometimes the smartest decisions are also the most difficult to make.

Big Think: You’ve said that successful entrepreneurship is about “recognizing your limits and selling while the going is good.” How did you come to this realization?

Gazdecki: A lot of entrepreneurs hold on to their companies too long. Some build their businesses to a few million in revenue, but when scaling them further requires a different skill set, that could be a great opportunity to sell. Hindsight is 20/20, but one thing I always think about is how many entrepreneurs I know who regret not selling. They got a good offer but wanted to keep going for one reason or another. That group tends to regret not selling way more than those who did sell regret selling.

Big Think: How do you manage emotions — like fear, doubt, or attachment — that would prevent you from taking bold but ultimately beneficial action?

Gazdecki: It comes down to the person. For me, I saw it as the end of a chapter. The whole story isn’t written. It’s not your whole career or the best thing you’ll ever do. You can always start another company. It’s common for entrepreneurs to sell and then ask, “What now?” So I think it helps to think through what you’ll do next before you even sell. One common thing I see at Acquire is people selling while already working on a second company.

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When I was in the process of selling Bizness Apps, I had already started another company. I wanted to keep running a company, but I had taken my first one as far as I could. I was also burned out. I wanted to go into a different industry, so I did.

If you’re thinking about selling and wondering if you’ll regret it, start thinking about what you’ll do next. Get really clear on why you’re selling. Are you doing it for financial security? Are you still passionate about the business?

Big Think: Has the experience of selling businesses changed you as an entrepreneur or influenced the way you go about building new companies?

Gazdecki: I get a lot less attached to businesses. I view them more rationally, not emotionally. I could have sold Bizness Apps for a much higher amount if I had sold earlier, but I held on because I was attached. Now, I can recognize these patterns much earlier — I can see which of a company’s problems are fixable and which are not.

Big Think: When you are attached to a business you’ve sold, how do you move forward without dwelling on the past?

Gazdecki: When you really dive into it — and a lot of entrepreneurs go through this — it’s not the company you miss, it’s building. It’s working with amazing people and having a good time with your startup. So If you sell your business and feel that kind of regret, my best advice is: start another company.

Big Think: When you go from building a company to selling one, do you put on different hats?

Gazdecki: It definitely requires a different mindset. You have to look at a business the way a buyer would, which is very different from how an entrepreneur sees it — especially the entrepreneur who built it. You might love certain features or specific customers, but buyers are looking at how healthy the business is, how profitable, how fast it’s growing, and how well it can be handed off.

If you’re thinking about selling and wondering if you’ll regret it, start thinking about what you’ll do next.

Is the CEO spending too much time in the business? When building a startup, it’s glorified to work 100 hours a week. But when selling, you want to show you’ve delegated key responsibilities and aren’t a single point of failure. So yes, it’s a different mindset. You have to look at it rationally, not emotionally, and be honest with yourself about how the business can improve for a buyer.

Big Think: Are there any common mistakes you’ve seen people repeat when selling a business?

Gazdecki: Overvaluing the business is a big one. Not understanding what buyers are actually looking for, or what will lower your valuation. A lot of startups have no bookkeeper, CFO, or finance team. Their finances are outdated, and so hiring someone to take care of that would be a great investment for them.

Big Think: We’ve talked about the challenges of selling a company. What about building a new one after the sale is done — are there any common pitfalls to avoid?

Gazdecki: I’ve probably overestimated my ability as an entrepreneur. After you sell a company, you think you’re really talented, like you can do things other entrepreneurs can’t. That might be true to an extent, but there’s always the market. Are you riding a wave with your new company? Are there things helping you move forward? For example, Bizness Apps was part of the mobile app wave. When I started, the iPhone had just come out, and mobile apps were booming. We made it easier for small businesses to build apps. That was just the right place, right time. 

My second company was called Altcoin. It was a cryptocurrency exchange that we started about seven years ago. The timing was right, but we couldn’t successfully build the software on the blockchain. It was a super technical company, and we struggled. I’m not very technical myself, yet I went into it thinking it would be super easy. I thought, “Let’s go after the crypto market. In 10 years, it’ll be big.” That was true, but in hindsight, I had a bit of hubris. I had just successfully sold a company, and thought I could do anything. But I’m not technical, and I had no business trying to secure people’s crypto.

A lot of entrepreneurship is trial and error. Over time, you learn what you’re really good at. I’m good at sales, marketing, and brand building. So with Acquire, I built the company around that.

Big Think: You recently tweeted that startups need an “outrageously optimistic” person. What does outrageous optimism look like, and why is it so important?

Gazdecki: When you build companies, the odds are so stacked against you — you kind of have to be a crazy person to even start. Over 90% percent fail, and only 4% get to $1 million in revenue. Companies that succeed are statistical anomalies.

There’s a good stat: the best CEOs wait until they have 60–70% of the information — then they make a decision.

If every entrepreneur thought, “We have a 0.25% chance of hitting $1 million,” no one would do it. You also have to pitch customers on something new. They ask, “Does it work? How long have you been doing this?” You need to persuade those first customers — and doing that requires being outrageously optimistic. You have to really believe in what you’re building.

Big Think: Do successful entrepreneurs retain outrageous optimism, even after experiencing multiple failures?

Gazdecki: I think so. There are so many hard parts about building a company — it never ends. If you don’t bounce back from setbacks, they’ll weigh you down. Everything that can go wrong does go wrong. Being able to dust yourself off and say, “Let’s keep going,” is super important.

You have to look at failure as an opportunity to learn. It’s part of the process. If you think about how much other entrepreneurs have failed, that might help you feel better. It’s just part of building a company.

Also: don’t be a perfectionist, and don’t overthink. There’s a good stat: the best CEOs wait until they have 60–70% of the information — then they make a decision. You’re never going to have all the information to make a perfect decision. You just have to make one, move forward. Was it right? No? OK, step back, make the next decision.

A decision is better than no decision. You won’t always know the exact answer. But the way to find the answer is to try something, see if it worked, adjust. It’s a lot of trial and error. If you’re a perfectionist, or if you overthink everything, you’ll move too slowly. You’ll never make progress.

Big Think: Overthinking is natural, and some people struggle with it more than others. How do you keep yourself in check?

Gazdecki: I keep a journal. If I have big problems I’m working through, I write them down weekly or monthly. Then when I look back, I see those “big” problems often lose importance. That helps me realize what feels huge now won’t matter as much later. Just keep making decisions, solving problems, and moving quickly. Every week there’s something new to work on.

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