Posted by: Jenn Deering Davis | December 6, 2010

8 (startup) things I’m better at now that I’m 30

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.



  1. I was thinking about this: “4. Standing my ground when it’s important.”

    Have you learned to admit that you’re wrong?

    That’s one thing I’ve learned. Probably the hardest lesson of all

    Me –

  2. Curious: What at 30 makes you better at selling than at 21. Just the fact that you have not done it before? Or that at 21 you’d prefer to work with computers and software, which I suspect you dealt with during school / college?

  3. […] View full post on Hacker News […]

  4. Great post. I am embarking on 30 next year and I am running into similar epiphanies.
    I realize you can’t be Allen Iverson forever. You have to adapt or they send you to Turkey.

    I would love to know your ‘small-talk-generating-algorithm’. These small discussions are usually the most crucial and I am just starting to find my way in these situations. Maybe you can drop a synopsis in your next post?

  5. @Troy Great question! I’m still working on that one. I have to keep something for the “Things I’m better at now that I’m 40” post.

    @Mukund I think one of the reasons I’m better at selling now because I’ve had so much more experience with it than when I was 21. I’m not a developer – my background is in communication – but I still started with zero sales training or skills. Plus, it helps that I’m really excited about the product/company I’m selling now. Makes a big difference.

    @Michael Thank you! I would love to share my algorithm. Blog post coming up soon. 🙂

  6. Interesting…specially the “taking one side” and not being “wishy-washy.” This is even more important when you are leading a team. People look up to you for a “definite” decision and being wishy-washy (even if you know that both view points are fine) can prove very demoralizing for your team.

    At the same time, I think you are wrongly attributing yourself to be an extrovert if you hate phone calls and hate to meet people in conferences.

  7. Wow, I have same problem with telephone, I feel like it has killed my parents, I hate it so much and I ignore people who I want to talk to.

  8. I would love to know your small talk trick – I’m an introvert who always hates conferences unless I’m with an extrovert who breaks the ice for me – then I love meeting people, but only one on one.

  9. very nice post!
    I’d love to know about the small-talk generating algorithm!

  10. I’m 37 now, and better at lots of those things than when I was 30! Now, what was it we were talking about?!

  11. Great post! I couldn’t agree more.

    I think with age some of these things come but I’ve been fortunate to have a few years in a sales job. The sales job did a lot to build confidence, the ability to talk people up and not be afraid of the phone. While it’s not for everyone if you’re going to be on the biz side of things you shouldn’t be afraid to jump into this role, it’s not that scary once you do it.

    • @Matthew That’s exactly right! I think the hardest part of selling is getting started. There’s some stigma around sales, but once you get some experience it becomes a lot less daunting.

  12. Great list! The thing I’d add, and this might go under “Selling”, is charging what I’m worth. It took me way too long to realize that just because something was easy for me that it still had a lot of value to the rest of the world, and I ought to be paid well for it.

  13. BTW, I’ll definitely post something about small talk next week. It’s something I initially developed in communication skills courses I taught at NC State University 7 or 8 years ago and have refined since. It won’t change your life, but it might help you navigate new conversations and come up with topics for those early interactions. It’s doctor-recommended. 🙂

  14. […] 8 (startup) things I’m better at now that I’m 30 When you’re 21 years old and working on your first startup, you’re convinced that you’re so much smarter than everyone […] […]

  15. Wow. Exactly like me from 1 to 8! Like … the same! Only that i’m 36. But then again, I’m a guy…:-)


  16. […] few months ago, I wrote a post about some of the startup things I’m better at now that I’m (a little) older and wiser. Lately it’s occurred to me how much more I […]

  17. […] few months ago, I wrote a post about some of the startup things I’m better at now that I’m (a little) older and wiser. Lately it’s occurred to me how much more I […]


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