When you’re 21 years old and working on your first startup, you’re convinced that you’re so much smarter than everyone who tried this before you. You don’t need advice or help – you just need to bust your ass, build a cool product, and then you’ll have millions of customers and can retire by age 25. This naive confidence is incredibly important to young entrepreneurs. Amazing things have been accomplished by young people with no fear.
Of course it turns out that very few of us hit a home run that first time. But the bravado (arrogance?) we had when we were 21 is eventually replaced by something even more useful. Dare I call it wisdom? I probably shouldn’t, as it would be presumptuous to assume that I’ve figured it all out at age 30. But I certainly am better at some things now compared to when I was when I was 21, and my current startup is better for it. Here are a few of those things.
1. Selling. I always hated the selling part of startups. I can’t count the number of times I’ve wailed, “But I’m not a salesperson!” to my co-founders in a wave of frustration and anxiety when it was my turn to do something remotely related to marketing or sales. As it turns out – yes, I am a salesperson. If you’re a founder, you have to sell. You might not be going door-to-door, but you will be selling in some capacity. I’m still not great at it – I often feel too pushy or like I’m talking too much – but I’m getting better every day. It helps to have a product you’re passionate about. But I now understand that selling is core to a successful startup. And I actually enjoy it.
2. Meeting new people. I’m an extrovert (if you’ve ever met me, you know this is true). But meeting new people in professional settings is terrifying. I remember the first tech event I attended years ago in Austin; I drank two beers before I had the courage to leave my cozy, supportive corner to talk to someone. These events are much easier for me now, even here in San Francisco. It helps to know that most other people there are just as nervous; focusing on that is the tech mixer version of visualizing everyone in their underwear. Plus, I now have a foolproof small-talk-generating-algorithm (patent pending) I can rely on if I need it. Ask me about it next time we’re at a happy hour together. And I realize how much I enjoy meeting new people and learning about what cool projects other people are working on.
3. Asking questions. To ask a good question, you have to listen closely. This applies to customers, co-workers, other entrepreneurs, and everyone else. I’ve definitely become a more focused listener, which allows me to ask useful questions. I’ve found this particularly useful when we’re working on new features – our customers are more than happy to provide us with more feedback than we can ever incorporate. I just have to ask them for it.
4. Standing my ground when it’s important. It’s hard for me to commit to a side. I’m typically one of those wishy-washy (I prefer to call it “open-minded”) individuals who sees the merit to multiple arguments, so it’s hard to side with one over the other. But I’ve learned that sometimes in a startup, there’s no room for wishy-washy. You have to make a decision and commit to it. There is plenty of room for debate and reevaluation, but there always comes a point when you just need to pick a side and move on. This is particularly important when talking to potential investors and reporters. These people ask hard questions, so it’s useful to be able to state a clear opinion and back it up with evidence. This was also useful during my dissertation defense. Doctoral committees – much like a company’s board – can sense indecision and they will pounce on it.
5. Answering the phone. I hate the phone. Despise it. I don’t know why; it’s not like a telephone killed my parents. But I hate it and I never used to answer it, even if I liked the person on the caller ID. However, now that I’m responsible for making sure our customers are happy and things are working like they expect them to, I have to answer the phone. When the phone rings, I answer it. I do this a lot. And you know what I’ve realized? It’s not all that bad. I’m still working on this, but at least I don’t get the sweats when the phone rings anymore.
6. Being concise. One big thing I’ve learned from explaining our startup at loud tech events with shoulder-surfing conversation companions is the value of brevity. I’m a lot more likely to hold someone’s attention if I can speak concisely about what we’re working on. If I’m bored when someone talks on and on and on about her project, then people will certainly be bored when I do it. I have 15-second, 30-second, and 60-second versions of our pitch, plus a variety of other short ways of talking about what we do.
7. Listening to advice. The brash and overconfident 21-year-old has matured into a slightly less foolhardy near-adult. I definitely realize the value of external advice now. I remember once hearing that the wisdom that comes with age has more to do with knowing what you don’t know than knowing what you do know. I think this is important – other people might have more insight into something than I do and it would behoove me to listen to them. This leads me to my final point.
8. Discerning. I’ve gotten much better at recognizing what’s interesting and important. Whether this is in a conversation with a stranger at a conference, determining which email to answer first, or knowing when I need to close the MacBook Pro and take a break, I have learned something important about evaluation. Life in a startup is all about choices. There’s never enough time to do everything, so every day I make countless decisions about how to spend my time. I am always weighing two options and choosing the one that seems better. Experience leads to better decision-making.
So it turns out that getting older isn’t all that bad. Sure, people say that 30 is the new 25 (or is it the new 18? I can’t keep up). But I’m pretty happy with how a little maturity helps me make this startup better than my first one. I’ll check back in when I’m 40 with an update.