Just finished reading Paul Graham’s essay titled What Startups Are Really Like that he wrote after soliciting feedback from YC cofounders on what surprised them most in starting a startup. It’s a great read and if you are thinking about starting a company, have started a company, or are interested in startups go check it out.

I’ve picked out a few points that really hit home with me (not all of them did, especially the points regarding investors since we haven’t take on any funding and don’t plan to at this point):

Be Careful With Cofounders This is critical. You need to trust the person (or people) that you’re running the company with and have confidence in them that they’ll want to head in the same direction. Sure you’ll disagree, but you need to be able to work things out together. Communication is key to a strong relationship. The comment is PG’s article is 100% true - it’s like marriage without the fucking.

Startups Take Over Your Life + It’s an Emotional Roller-coaster I am always thinking about our business. I stay up late working on things, I get up early to work on things, I work on the weekends and I wish I had more time every day. I go to bed thinking about problems and wake up thinking through solutions. I love it, I hate it, I’m excited and I’m beat down. I get super fired up for the wins and crushed for the losses. It’s definitely all consuming.

With that said - it changes. You’re business grows and you with it. You start hiring the right people and stop doing everything. You role continually changes and allows you to focus on doing the next best thing for the business. It’s fantastic.

Persistence Is the Key Things add up over time. Every iteration of your product/service/business is forward progress. The key is to keep at it. If you can get 2-5 things done every day to impact the business, just think of what that adds up to over time.

Think Long-Term You’re a very short term thinker when you first start your business. It hasn’t been until recently that we’ve started to really think about the long term direction of our business and define where it’s heading.

Lots of Little Things Starting and operating a successful business is no small task. There are thousands of little things that need to be done at any one time. You have to trust that not only your team is going to get things done, but that they’re also always thinking about how to do things better.

Don’t Worry about Competitors The number one biggest thing that I’ve been surprised at is the notion of “Well there is already X doing Y”. About a year after starting the company, a person I met networking at a local technology meetup recommended that I talk to the Chicagoland Entrepreneurial Center to see how they could help us out. I got ahold of them, completed some paperwork and spoke with one of their advisors over the phone. He suggested that I come into present an overview of our business to a few members of their team. I remember the day well - I sat across the table and walked through 10 slides about the fundamentals of our business, followed by a demo of our TextMe product. At the conclusion, I asked for their feedback to which they told me that they thought the product was great but that we were in a tough market with a lot of competitors, an assumption they based on knowing one local company that had gained credibility in the Chicago business community for doing the sames things that I was talking about with them. They also wanted me to join the Chicago chamber of commerce (which seemed odd to me since the membership was expensive and they were here to help me as a small business owner). I walked out of the office thinking about what a complete waste of time the meeting was and how the CEC wouldn’t help a company unless the company already had connections or the pitch was blatantly obvious. I also thought about how much work it would take to get funding and dreaded the idea. Fast forward two years later and we’ve built a successful business that is profitable and growing. Revenue wise, we’ve seen over 100% growth every year in the last three years and expect to continue do so in 2010. In fact, we’re just now getting to the point where we’re investing in the “business” side of our business by hiring people to focus on sales and marketing. Bottom line, there is plenty of competition out there but we’ve carved out our own niche and are doing great. Had I listened to all of the people who thought we couldn’t or shouldn’t do it…well I’d probably be getting ready to conduct year end reviews right now and having my direct reports put together goals for their team, which would need to map to goals that I put together for my team, which map to goals that my boss put together for his team, etc. I definitely do not miss working for a big company.

There are a few other things that I want to add to Paul’s list:

It’s all about the people Everyone we hire brings dramatically impacts our organization. With each team members comes not only a new skill set, but also new energy and new perspective. As a business owner, you need to have a solid mental map of the culture that you want to build and incorporate this into the foundation of your hiring. The 80/20 rule doesn’t apply to growing a team - always hire the best.

I care a lot more about my team than I did when working for a company That might sound presumptuous, but I’m always thinking about the people on my team and doing my best to make sure they’re 100% happy. I’m very aware of what people are working on and always performing a mental litmus test to understand how satisfied they are with their job. I am extremely proud that we’ve created a business entity that supports seven full time employees (eight as of 11/2/2009) and their families. Things like health insurance and time off are a big deal and important to get right. When I was at Orbitz, I left managing a team of 20+ that I cared about, but definitely not in the same way that I care about our team. It’s just totally different.

I’ll continue to update this post as think more about it.