I remember how it felt when I left the job I feared the most. It felt like the day Elwood Blues picked up his brother Jake from Joliet. Sweet freedom.During my tenure there, I remember my co-workers describing how it used to be before my time. It started as a tight-knit group of eight, in a cozy townhouse nestled in a happening part of the city. They had an open floor plan because they had no choice, not because it was hip. Everyone would pitch together, travel together, work as a single team on projects, and hang out outside of work. And it didn’t matter who owned the company and who didn’t—it was just a work family thriving in a hierarchy-free utopia where everyone had equal say.As the company grew, they jettisoned the cozy office for a bigger, staler environment. Fluorescent lights. Cubicles. People were often hired in fire drill fashion to fill "look-what-we-found" project slots. When employees didn’t work out because they weren’t properly vetted, they were shown the door.As headcount further increased, the owners become more distant and impatient. They’d fail to set proper expectations, and when employees would inevitably fall short of their mystery benchmarks, all hell would break loose. It became a toxic environment propelled by threats and intimidation. Current and former employees got together outside of work and gossiped regularly about the company, myself included. I remember thinking, “If I own my own company some day, I’ll never let things get like this.” I’d create the company I always wanted to work for.In 2006, I finally got the chance. And interestingly, the growth pattern was strikingly similar. We started in an old brewery in a hip neighborhood, and had a handful of really great people. We’d work, eat, and hang out together. Then, as we got bigger, we moved to larger offices, instituted more complex rules, and had to work harder to keep everyone on the same page.When people asked me how big I wanted the company to be, I’d always say, “I can’t see growing beyond ten people. I want to know everyone.” Then, over time, I’d find myself ratcheting up that number when I was asked the question again. The work was coming in, and it seemed silly to turn it down. More work, more people.Almost weekly, I kept reminding myself not to end up like my former bosses. “Greg, always remember to be fair, be supportive, have fun, and don’t to take work too seriously,” I’d say in my head.A funny thing happens along the way though, and I didn’t understand this when I’d sit at those happy hours and bash my old bosses. When you bootstrap something, you quite literally pour your blood, sweat, and tears into it, not to mention every penny you have. It’s your baby, and you’ll do anything to protect it. You have a vision of how it will turn out, all the way down to the color of the office chairs you’ll have in 20 years. It’s easy to be the freewheeling fun guy when you’re eight people. When you quadruple that, you have to delegate responsibilities if you are to stand a chance. And if you’re a control freak, that’s really tough. The care you take in that process will either make your life easier, or give you a heart murmur.Which way that goes is entirely on you.If you take the time to work with people, clearly establish expectations, and show confidence in them, you have a much greater chance of being on the right trajectory. Move too fast, become distracted, or be a chronic blamer, and you’ll be cursed over vodka tonics. That’s about it.I think a lot about those bitch-a-thons we used to have. I’ve had nightmares about being the subject of those too, I must admit. At the end of the day, I feel the path I’ve chosen and the decisions I’ve made have been the right ones, even if at times I executed them with high school sophistication. And I’m okay with that.