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To sell or not to sell \u2014 that\u2019s 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\u2019s yet to come. Wait too long, and you risk cashing out after your business has already peaked.<\/p>\n
At one point, Andrew Gazdecki belonged to the second of these two cohorts. \u201cI held on because I was attached,\u201d 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.<\/p>\n
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 \u2014 which was as bureaucratically cumbersome as it was emotionally draining \u2014\u00a0 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.<\/p>\n
Underpinning both Gazdecki\u2019s career and Acquire.com\u2019s 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.\u00a0<\/p>\n
Here, Gazdecki joins Big Think for a chat about when to let go and when to hold on, the dangers of overestimating one\u2019s own ability, and why sometimes the smartest decisions are also the most difficult to make.<\/p>\n
Big Think: You\u2019ve said that successful entrepreneurship is about \u201crecognizing your limits and selling while the going is good.\u201d How did you come to this realization?<\/p>\n
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.<\/p>\n
Big Think: How do you manage emotions \u2014 like fear, doubt, or attachment \u2014 that would prevent you from taking bold but ultimately beneficial action?<\/p>\n
Gazdecki: It comes down to the person. For me, I saw it as the end of a chapter. The whole story isn\u2019t written. It\u2019s not your whole career or the best thing you\u2019ll ever do. You can always start another company. It\u2019s common for entrepreneurs to sell and then ask, \u201cWhat now?\u201d So I think it helps to think through what you\u2019ll do next before you even sell. One common thing I see at Acquire is people selling while already working on a second company.<\/p>\n
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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.<\/p>\n
If you\u2019re thinking about selling and wondering if you\u2019ll regret it, start thinking about what you\u2019ll do next. Get really clear on why you\u2019re selling. Are you doing it for financial security? Are you still passionate about the business?<\/p>\n
Big Think: Has the experience of selling businesses changed you as an entrepreneur or influenced the way you go about building new companies?<\/p>\n
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 \u2014 I can see which of a company\u2019s problems are fixable and which are not.<\/p>\n
Big Think: When you are attached to a business you\u2019ve sold, how do you move forward without dwelling on the past?<\/p>\n
Gazdecki: When you really dive into it \u2014 and a lot of entrepreneurs go through this \u2014 it\u2019s not the company you miss, it\u2019s building. It\u2019s 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.<\/p>\n
Big Think: When you go from building a company to selling one, do you put on different hats?<\/p>\n
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 \u2014 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\u2019s growing, and how well it can be handed off.<\/p>\n
If you\u2019re thinking about selling and wondering if you\u2019ll regret it, start thinking about what you\u2019ll do next.<\/p>\n
Is the CEO spending too much time in the business? When building a startup, it\u2019s glorified to work 100 hours a week. But when selling, you want to show you\u2019ve delegated key responsibilities and aren\u2019t a single point of failure. So yes, it\u2019s 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.<\/p>\n
Big Think: Are there any common mistakes you\u2019ve seen people repeat when selling a business?<\/p>\n
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.<\/p>\n
Big Think: We\u2019ve talked about the challenges of selling a company. What about building a new one after the sale is done \u2014 are there any common pitfalls to avoid?<\/p>\n
Gazdecki: I\u2019ve probably overestimated my ability as an entrepreneur. After you sell a company, you think you\u2019re really talented, like you can do things other entrepreneurs can\u2019t. That might be true to an extent, but there\u2019s 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.\u00a0<\/p>\n
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\u2019t successfully build the software on the blockchain. It was a super technical company, and we struggled. I\u2019m not very technical myself, yet I went into it thinking it would be super easy. I thought, \u201cLet\u2019s go after the crypto market. In 10 years, it\u2019ll be big.\u201d 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\u2019m not technical, and I had no business trying to secure people\u2019s crypto.<\/p>\n
A lot of entrepreneurship is trial and error. Over time, you learn what you\u2019re really good at. I\u2019m good at sales, marketing, and brand building. So with Acquire, I built the company around that.<\/p>\n
Big Think: You recently tweeted that startups need an \u201coutrageously optimistic\u201d person. What does outrageous optimism look like, and why is it so important?<\/p>\n
Gazdecki: When you build companies, the odds are so stacked against you \u2014 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.<\/p>\n
There\u2019s a good stat: the best CEOs wait until they have 60\u201370% of the information \u2014 then they make a decision.<\/p>\n
If every entrepreneur thought, \u201cWe have a 0.25% chance of hitting $1 million,\u201d no one would do it. You also have to pitch customers on something new. They ask, \u201cDoes it work? How long have you been doing this?\u201d You need to persuade those first customers \u2014 and doing that requires being outrageously optimistic. You have to really believe in what you\u2019re building.<\/p>\n
Big Think: Do successful entrepreneurs retain outrageous optimism, even after experiencing multiple failures?<\/p>\n
Gazdecki: I think so. There are so many hard parts about building a company \u2014 it never ends. If you don\u2019t bounce back from setbacks, they\u2019ll weigh you down. Everything that can go wrong does go wrong. Being able to dust yourself off and say, \u201cLet\u2019s keep going,\u201d is super important.<\/p>\n
You have to look at failure as an opportunity to learn. It\u2019s part of the process. If you think about how much other entrepreneurs have failed, that might help you feel better. It\u2019s just part of building a company.<\/p>\n
Also: don\u2019t be a perfectionist, and don\u2019t overthink. There\u2019s a good stat: the best CEOs wait until they have 60\u201370% of the information \u2014 then they make a decision. You\u2019re 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.<\/p>\n
A decision is better than no decision. You won\u2019t always know the exact answer. But the way to find the answer is to try something, see if it worked, adjust. It\u2019s a lot of trial and error. If you\u2019re a perfectionist, or if you overthink everything, you\u2019ll move too slowly. You\u2019ll never make progress.<\/p>\n
Big Think: Overthinking is natural, and some people struggle with it more than others. How do you keep yourself in check?<\/p>\n
Gazdecki: I keep a journal. If I have big problems I\u2019m working through, I write them down weekly or monthly. Then when I look back, I see those \u201cbig\u201d problems often lose importance. That helps me realize what feels huge now won\u2019t matter as much later. Just keep making decisions, solving problems, and moving quickly. Every week there\u2019s something new to work on.<\/p>\n
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