Startupland summary

If you’re a kid on the playground looking for money, the school bully probably wouldn’t be the best person to go to. He might give you the money, but if so, he’ll ask for it back with interest. The start-up scene isn’t all that different.

Not all investors are good investors. Unfortunately, start-ups don’t usually have a lot of options when it comes to getting their initial investments; when you first start out, you’ll be exposed to a lot of investors who are only concerned with themselves. The best thing for your start-up is to turn them down and hold out for a bit longer.

Did you play team sports in gym class as a kid? Which team member was the most fun: the person who wanted everyone to participate and have a good time, or the star player who scored all the goals but did it alone? Of course, it’s the former.

Start-ups work in a similar way. People with good team-building skills often make the best entrepreneurs; however, it’s not always easy to keep the team on track.

Outsiders are often annoyed by American aphorisms like “fake it till you make it” or “winners never quit.” American optimism might seem unrealistic at first glance, but it’s actually helped foster a great start-up environment. You can’t succeed with a start-up if you don’t have the confidence to take risks!

In fact, all major internet-related businesses (and the internet itself!) originated in the United States. Denmark, for instance, only had one internet provider and very expensive dial-up in the early ‘90s, but American cities like San Francisco embraced the internet early on and were enthusiastic about it right away.

Entrepreneurs’ lives often revolve around their work. They might work over 12 hours a day and when they’re not working, they’re thinking about work. Naturally, this can be challenging for their families for a number of reasons.

For one, it’s hard to take financial risks when you have a family. The author struggled with this when he accumulated a lot of credit card debt and used up his retirement money while building Zendesk. He also took out a $50,000 loan that he was personally liable for. At one point, he was two weeks away from going bankrupt if he didn’t get more funding.

If you’ve ever had to sort through a pile of 80 CVs, all written in the same cryptic language, you know that picking the right candidate can be difficult. And sometimes interviews just make the situation worse: the interviewees get nervous and speak too little or too much.

Now imagine if you had to go through all this in a foreign country! That’s exactly what the Zendesk founders had to do after they moved to Boston, and they learned some pretty important lessons in the process.

Launching a start-up is like jumping from a ten-meter diving board: you might land a perfect dive, or do a painful belly flop. And you’ll definitely have to take several dives before you really figure out what you’re doing.

For example, when Zendesk was starting out, the author had a few false starts while looking for funding. At one point, when the company was still based in Denmark, he flew to the United States to meet a partner in a venture capitalist firm. But his timing could hardly have been worse: the 2008 financial crisis was underway, mortgages were no longer available and big banks like Lehman Brothers and Merrill Lynch had collapsed.