The Hardest Part of My Startup Was Learning to Let Go

With our scalability problem finally behind us, I could turn my attention to the rest of the business. The truth is, I’d been running Bizness Apps pretty much by myself since we launched, and I was completely overwhelmed. My days were a blur of answering support tickets, making sales calls, and troubleshooting with developers. I was pulling 100-hour weeks, chained to my phone and answering emails at one or two in the morning. I can’t imagine doing that now, but sometimes that’s what it takes to get an edge.

It was hard to disconnect and give my friends and family the attention they deserved. Thankfully, they understood what this business meant to me. While other kids dream of being astronauts, I just wanted to be a CEO, so it never felt like work. Still, I couldn’t have survived those early years without Christian, my investor. Most investors check in quarterly; I was talking to him several times a day. At one point, I was emailing him more than his own wife did. You’d think it would have annoyed him, but we were good friends and it never felt like a formal investor relationship.

Eventually, though, the constant calls and emails became a crutch. I realized I had to start acting like a CEO, not just playing the part. It was time to stand on my own two feet. But what does a CEO actually do? I had no clue. That’s where my coach, Tim Porthouse, came in. Tim taught me that a CEO’s job is to fire themselves from every role—sales, marketing, product development—and delegate those tasks. I had to step back and focus on the big picture: strategy, leadership, and culture. To do that, I needed to find the right people.

Finding Your People Is Everything

I initially hoped to build my team in Chico. It was a college town, the perfect launchpad for a . It had a steady stream of young people and local businesses that had become our first customers. We hit $1 million in annual recurring revenue in our first year and $3 million in our second. Our timing was perfect; we were helping small businesses navigate a new marketing channel, and Chico was the ideal testing ground.

You’d think the town would be overflowing with bright graduates eager to join a growing . But the best and brightest almost always left for bigger cities and bigger names. I ended up with a small sales team of six, mostly friends. Everyone else was outsourced—developers in China, Russia, and Brazil. The growth was thrilling but exhausting. I was juggling customer acquisition, brand strategy, and market research while trying to manage technical issues across different time zones.

This setup was holding us back. A thrives on collaboration, with everyone rallying around a common goal. We were in a high-growth phase and needed to be agile, but most of my team was remote. My hiring process was just as haphazard. I’d give candidates a small project and see what happened, without any code reviews or technical questions. I was lucky to find one good coder out of five. In the early days, our product worked, but it wasn't great. I knew if I wanted to build a world-class team, I had to look beyond Chico.

A New Home and a Frugal Mindset

The obvious answer was San Francisco, the heart of Silicon Valley. But we couldn't afford it. The rent in 2012 was astronomical. Instead, we moved to Millbrae, a city about a 30-minute drive away. It wasn’t the epicenter of tech, but it put us close enough to the talent pool.

Our office was a major upgrade from our tiny room in Chico, but it was incredibly plain. It looked like it hadn’t been updated since the 1960s, complete with ashtrays in the hallways. But it was cheap, and they offered a month-to-month lease, which was perfect for managing our . I’ve always been frugal, and the last thing I wanted was to get weighed down by fixed expenses. We didn’t have a receptionist or a game room. I told the team, “We invest money where it matters—in the business.” We were focused on one thing: how to acquire, delight, and retain customers. That was our secret sauce.

We arrived in Millbrae with ten people and grew to thirty within a year. Soon we outgrew that office and moved to a brand-new space on California Street in San Francisco. The business was at a crucial point, gearing up for explosive growth, and I knew my hiring decisions would define our future. To hire the best, you need to understand each role inside and out. Having done them all myself, I had a good idea of what to look for.

My approach was simple. I looked for three things in a candidate:

1. This was the most important factor.
2. This was about attitude and energy.
3. This was actually the easiest to pass.

I’ve always believed that a smart, positive person can learn the necessary skills. Attitude trumps experience. Neither my VP of Product nor my COO had prior experience in those roles, but they were eager to learn and became world-class leaders. To this day, that approach has never failed me.

Building a Culture That Lasts

I wanted to hire people who would genuinely enjoy being part of our team, which meant building the right company culture. We hired people who were like me: positive, persistent, and passionate about our mission. We never judged candidates by their resumes, and we gave people a chance to grow into the roles they wanted. This philosophy was key to turning a with a dedicated team.

The core of our culture was positivity. When things go wrong, I try to zoom out and remember how much worse they could be. If you have your health, a roof over your head, and food on the table, you’re doing better than millions. Negativity is a drain on energy and blinds you to solutions. Positivity, on the other hand, is contagious. It lifts the whole team. Companies with engaged employees outperform those without by 202 percent, and it shows. This positive culture is why people stuck around. In the Bay Area, employees typically stay at a company for one or two years. Our people stayed for five to six. It’s about playing the long game.

Our mission—to help small businesses succeed—was our North Star. It guided every decision we made and kept us on track. When you build a great culture, you create a team that can weather any storm.

The CEO’s Real Job

Some people think being a CEO is about cracking the whip. I see it differently. My job was to hire a great team, create a great environment, and then get out of their way. I was the navigator, setting the direction while the team propelled us forward. My meetings weren’t about asking, “Why haven’t you done this?” They were about asking, “How can I help you do your best work? What do you need from me?”

If you micromanage people, you strip them of their autonomy and motivation. You have to trust your team. Relinquishing control is hard, but holding on too tightly is one of the costliest mistakes you can make. I learned this the hard way twice.

First, I started a $100,000-per-month Google Ads campaign without anyone analyzing its performance. The signups were coming in, so I figured everything was fine. It wasn't until we hired someone to dig into the data that we realized the campaign was a complete waste of money. I was basically blowing up a Ferrari every month.

Second, our server infrastructure couldn't keep up with our growth. In the early days, we rented servers from firms in Texas and Chicago. As millions of people started using our apps, the servers crashed constantly. It was a nightmare. Our remote engineers were always putting out fires instead of building the product. The only solution was to hire an in-house VP of Engineering and a dedicated team to rewrite our entire architecture. It was a tough transition, but it made our platform one of the truly that could handle massive growth.

How to Handle Copycats

As we grew, our success attracted competitors. Some were pretty shameless about it, signing up as resellers just to deconstruct our software and copy it line for line. I used to find our code in their products. Another CEO might have sued, but I knew that would be a distraction. Running a requires psychological toughness.

I told my team, “If they’re spending money to educate the market, we benefit because we have the best product.” We were five years ahead of everyone. Instead of getting flustered, I was flattered. If no one is copying you, you’re not trying hard enough. We focused on what made us different: the best customer support, the best product, and the best reseller program.

The four years we spent in that San Francisco office were the honeymoon period. We were signing up hundreds of customers a day and enjoying the ride. I had finally learned what it meant to be a CEO, thanks to great mentors and an incredible team. We had created a culture and a story people cared about, setting the stage for everything that came next.