What I learned after selling my startup
Retired Software Engineer
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What I learned after selling my startup<br>I always worked for myself in startup land. Then my company was acquired and I experienced what it's like to be a cog in the wheel of a large company. These are my observations from that period.<br>Retired Software Engineer<br>Apr 16, 2026
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Preamble
I sold my startup. I put a lot of time, money and emotional energy into building my company. I’m not the first to go this route and much has been written about the “Founder’s Journey”; the emotional roller coaster of self-doubt mixed with brief moments of euphoria. I don’t want to write about that. I want to instead share my observations and learnings from my time working for a large US corporation. I had previously only worked for myself or at your typical part-time jobs like grocery stores and movie theatres as a teenager, so this experience was entirely new for me. I never before had to use Workday, or file expenses with SAP Concur, which I’m convinced is the worst, largely deployed software in the world. I was never part of an Org chart and never gave any consideration to people’s job titles and why they cared so much about it1.<br>Let me set the stage. When you sell your company, typically you get some of the money up front in cash and the rest as part of an “earn out”. Typically this period is four years and for every year you complete, you get another chunk of the original sales price. For example, you get 60% of the total sale price on the day the deal closes, 20% after year one, 10% after year two and then 5% after each subsequent year.<br>I knew I couldn’t last four years working for someone else so my lawyers were able to successfully knock it down to two years, like bargaining for a shorter prison sentence. How hard could two years be?<br>I won’t mention the name of my startup, nor will I name the company who acquired my company. Not because I’m bound by some NDA, but rather I think this information would only distract from the main content. So let’s call the company Acquirer. OK? OK.<br>These are my observations and learnings from a two year earn out.<br>Feast or famine … but mostly feast
My startup was a typical SaaS startup, which relied on recurring revenue via subscriptions. I made the decision early on to target larger enterprises as customers. So typical monthly contracts ranged from $5,000 a month to $100,000 per month. Landing a new whale of a customer, say greater than a $200,000 per year contract, was a game changer. I could hire one or two more people, or increase marketing spend. But I had to weigh those options because I could also choose to not do anything and just pocket that money. You’re always weighing these options; instant gratification or long-term growth. Conversely, when you lose a large customer, your plans have to change and you take a real hit to your finances and your future, not to mention your ego. So each and every day, you, and once you’ve grown large enough, your sales team, are on the prowl filling the sales pipeline, qualifying leads and trying to close deals.<br>But once I started working for Acquirer, things completely flipped. I no longer felt like a lion hunting in the savannah; now I was a lion lazily laying in the shade as my zookeeper tossed meat at my face every two weeks. And like most US tech companies, the salaries Acquirer paid were fantastic relative to the work expected.2 I was a very well fed zoo animal who quickly lost the ability and will to hunt for themselves. For those people who have always worked salaried jobs, you can’t imagine the feeling for someone like me to suddenly, for the first time in nearly 20 years, receive money like clockwork on the 15th and 30th of each month just for not getting fired. Like a kid on Christmas morning, I would excitedly check my bank account every pay day for the first few months and giggle seeing the money get deposited. I know it sounds silly, especially because the sale of my company already made me wealthy, but still, it felt surreal.<br>Creating software in a big company vs small company
I intentionally went into my new job with a very open mindset. While my company had built and shipped software to large customers and governments in the past, I had never been part of a big team like I was now. So I adopted the default position that the way things were done in a smaller startup will not fly at a larger company. I told myself, “Check your ego, assume you don’t know anything, be open to doing things differently and learning from others”.<br>But you know what - I found the process to be largely the same because the toolchain is largely the same. Jira, Github, Docker or Kubernetes, Python, AWS etc. That said, I was a bit surprised at how lax some things were. The code reviews for example were clearly very cursory. It was obvious some folks were just handing out thumbs up on code reviews like they were going out of style. I saw code committed that I never...