4 Entrepreneurship Lessons

Today, I went to the “Rise of the Rest Road Trip” fireside chat with Steve Case, the co-founder of AOL, and Jim McKelvey, the co-founder of square. The talk was incredible. I’ll sort this article into three sections: the introduction, four takeaways I gained from the talk, and my conclusion on the importance of entrepreneurship.


The Rise of the Rest Road Trip is a tour across the country where Steve Case goes to towns that are underrepresented in entrepreneurship (essentially almost everywhere except Silicon Valley and NYC) and seeks to strengthen the local startup communities. This usually includes a presentation, a pitch competition, and an afternoon networking event.

I came into the room today to find myself completely underdressed and star-struck. Everyone was either in a suit or a blazer. I’m inclined to believe that some of these people took off work to come see this presentation. A few undergrads and graduate students were there too. I sat next to a postdoc from the medical school. My jeans and red Henley shirt were a bit out of place, but I’d rather be out of place at a great event than not be there at all.

My "I'm so underdressed but this is awesome" face.

My “I’m so underdressed but this is awesome” face.

Looking around, I saw the Chancellor, the Provost, and the Dean of the business school in the audience; and those were just the people I recognized. During the question and answer period, a young man stood up behind me, explaining that he is sixteen years old and is the founder of a startup that employs over 150 people. In front of me, a woman prefaced her question with an introduction: she is the founder of Build-a-Bear. I am awestruck by the lives of these people, to see how much they’ve changed the world. One day I hope I’ll make as much of an impact as they have.

The peak of my fandom happened after the presentation when I had a chance to talk to Steve Case about his career. He had some great things to share, but what meant the most was just the fact that I got to talk to him at all. Here I was, a 21 year old college senior, asking the co-founder of AOL what went through his head when he was my age. Suddenly, it seems possible that one day, I too could do something of his caliber. Meeting him in the flesh brought this idea from a distant dream to a concrete reality in front of me.


  1. Focus on fixing problems. As Jim explained, a lot of his businesses were founded from being annoyed. Square, for instance, came from his annoyance at not being able to sell a piece of art to a woman with a credit card. Steve reinforced this point, saying: “entrepreneurs fundamentally see the world and see how it could be better. It requires paying attention and understanding what is happening, and thinking outside the box.”
  2. Persevere. Steve told us a story about AOL that made me realize how much of an uphill battle it was. In 1985, 3% of Americans were online, and most of them only for an hour per week. Access was expensive. Most people didn’t have modems. Even if you did get online, there was hardly anyone else to talk to. Slowly, AOL worked to remedy these issues. It took AOL a decade before getting traction. Square, on a similar note, had to practice patience. The Square software took about 3 weeks to build; yet it took 18 months to get the financial regulation to launch the company. Overnight successes are months and years in the making.
  3. Be humble. You won’t always be the smartest person in the room. Your ability to work with others that are smarter than you will be the difference between a good company and an incredible company.
  4. Delegate to and empower your team. Entrepreneurship is a team sport. As Steve mentioned, an ideal leader will wake up many days and find that he has no work to do, because he has empowered, inspired, and set the agenda for his team. You can’t do everything on your own. You need to trust those you work with. Partnerships and communities are what build startups. As one of Steve’s favorite proverbs mentions, “If you want to go quickly, go alone—but if you want to go far, go together.”

What Entrepreneurship is Really About

One thing that I can’t get out of my head is how strongly both Jim and Steve emphasized that entrepreneurship is vital to our economic growth and a better society. Steve mentioned “there will never be stability and peace if there aren’t jobs, especially for young people.” This could be the reason behind crime and civil unrest; people just want to pursue the American dream, working hard and building a life for themselves. Entrepreneurs that create jobs make that dream possible. The Rise of the Rest focuses on this, with a bias towards backing companies that create jobs.

What nobody mentioned today, but is even more important in my eyes, is the role entrepreneurship will play as automation continues to improve. As robotics technologies continue to become cheaper and more sophisticated, machines will replace more and more jobs. Entrepreneurs need to step up and find ways to create new jobs, bringing more value to society and empowering people who, at the end of the day, want to put in an honest day’s work. If entrepreneurs completely stopped creating companies and jobs for the next 20 years, I’d imagine we’d tear our world apart with anger and unrest. It’s that important.

So, if you take away one thing from this, it is to be curious. Look at the world a little differently. Imagine how things could be, and make that a reality.