What It’s Really Like to Sell Your First Startup

After emerging from a major crisis with Apple, I found myself taking a hard look at the business I had spent eight years of my life building. I started Bizness Apps in my college dorm, working 100-hour weeks to grow it into a tech startup with $10 million in annual recurring revenue. It was my first real company, and I dove into leadership with zero experience. I stumbled a lot, but that willingness to learn on the fly was what made the whole thing possible.

But in the startup world, eight years is an eternity. It was clear to everyone involved that Bizness Apps wasn't heading for an IPO. We could have kept chasing profitability, but those returns eventually shrink. When your focus shifts entirely to cutting costs, you risk degrading your product and losing ground to competitors. Selling was on everyone’s mind—mine, my investors’, and my senior leadership’s. We had just pulled the business back from the brink, and it felt like the right time to say goodbye.

The Long Road to Letting Go

Every founder dreams of selling. You pour your life into a business startup, and the sale is the moment that investment pays off in a life-changing way. I knew from day one that I wanted to eventually sell Bizness Apps; it was just a question of when.

Back in 2016, I’d hired an investment bank to test the waters. I had relationships with numerous private equity firms and strategic acquirers like GoDaddy and Web.com. I got a couple of offers, but they weren't right. One required the entire team to relocate to Florida, and I couldn't put my staff through that. They also wanted a large earnout, tying the final price to the company's performance after I was gone—a deal I wasn’t comfortable with since I’d no longer be in control. Another offer, a 70% buyout from a PE firm, also fell through because the terms just didn't feel fair.

Since the company was still growing, I decided to hold on. Then the Apple crisis hit, and I spent months kicking myself for not selling when I had the chance. Luckily, two years later, I was able to sell the business for the same valuation. I got very fortunate.

One day, I got a call out of the blue from an associate at ESW Capital, an acquisition firm specializing in software businesses. I was exhausted from the fight with Apple and desperate for a break. They asked if I wanted to sell. My response was simple: “Sure. Who are you guys? I’m always up for entertaining an offer.”

When their offer came in, I was floored. They proposed a full stock purchase, which minimized our tax liabilities. Even better, they were willing to buy the $2 million in cash we had in our bank account—something buyers rarely do because it just increases the purchase price. This structure made it an incredibly founder-friendly deal. It meant I could walk away quickly with enough money to never worry about finances again. It felt almost too good to be true, but ESW had a 98% close rate on their letters of intent (LOIs), so I knew they were serious. How could I refuse? I probably would have sold for half as much.

The Thirty-Day Gauntlet

Even though I was thrilled, I tried to play it cool. Before this, I assumed acquisitions were based on a buyer falling in love with your company. The reality is that it’s all math. Valuations aren't round numbers; they're calculated down to the decimal point based on financial metrics.

For the next thirty days, I barely ate or slept. I knew the buyer could walk away at any moment, so my team and I responded to every due diligence request at lightning speed. If you’ve never been through it, imagine the most intense audit of your life. They scrutinized everything: our financials, technology, operations, and business model. It was non-stop work for me, my CFO, and my VPs of Product and Engineering.

To keep our “secret project” under wraps, I told employees we were being audited by the IRS. It was close enough to the truth. We essentially wrote a manual on how to run our entire tech startup, detailing everything from our server architecture to our marketing strategy. ESW’s team even reviewed our open-source libraries, forcing us to rebuild certain features for legal compliance.

Breaking the News and Taking Care of the Team

I knew the sale would likely lead to layoffs, as reducing staff to boost profitability is a common post-acquisition move. I couldn't offer any guarantees about job security, but I was determined to ensure my employees benefited from the sale. Until the money is wired, a deal is never 100% done, and I didn’t want to cause a panic.

I planned to announce the sale on a Friday, the expected closing day. But then, ESW requested one last document, leaving everyone in limbo. The atmosphere was tense. Employees started looking up ESW’s acquisition history, and people were torn between fearing they’d be fired and hoping they’d become millionaires. The deal finally closed the following Thursday.

I formally announced the acquisition and my ninety-day transition plan. My first priority was my team. Since I had no control over what the new owners would do, I did what I could. I gave everyone the option to leave with a generous severance package and personally helped them find new jobs. ESW had also given me a $500,000 check to seed a new business. Instead, I decided to share it equally among my team members as an extra thank-you.

After the Wire Transfer

Seeing that wire transfer hit your account is a moment you never forget. At first, I was in shock, worried the buyer would find something wrong and sue me. Of course, they didn’t. When you’re twenty-nine and suddenly have millions of dollars from something you started in a dorm room, your mind plays tricks on you.

So, what did I do with the money? I bought a house for my wife and me in San Mateo—a place to raise a family. I splurged on a C63 AMG Mercedes, my first real treat in years. The rest went into the stock market and seeding new business ideas. For me, wealth isn't about lavish spending; it's about the freedom to pursue your passions and provide for your family. This is the reality behind the fantasy of finding ; true freedom is the real prize.

The Next Chapter: What True Entrepreneurship Means

True entrepreneurs rarely stop at one success. After selling Bizness Apps, my journey continued. I launched Altcoin, a crypto trading platform, consulted for a company called Spiff and helped them grow 1,000% in ten months, and eventually founded MicroAcquire to solve the very problems I faced when selling my own .

My experience taught me that entrepreneurship isn't about having a completely original idea. It’s about solving a problem well. If you’re scared to fail, you’re scared to succeed. Each venture is a learning experience. You don’t need millions in to get going; you just need the right idea, a resilient attitude, and a focus on your customers. Making money is simply a byproduct of doing that well.

My journey from a college project that turned from a employment for a whole team was a whirlwind. Now, I want to help others learn from my experiences so they can build their own businesses and create their own solutions. And that, to me, is what it’s all about.