Feeling Old(er) at Big Omaha

For many years I was often the youngest person in the room. I started my first company at 19 and had already had several bizarre “too young” experiences by the time I was 21. I vividly remember almost losing our largest client at the time because they had taken my partner Dave out for drinks (he is three years older than me) and they somehow pried out of him that I was only 21. That generated a lot of anxiety for a week or so.

I’m at the Big Omaha Conference today for the first time. I’m a big fan of Jeff Slobotski and have been semi-gracefully dodging his invites for years. This year I thought I’d come hang out for a day. So here I am.

Last night I went to the VIP pre-opening party. I hung out and talked to some folks and then realized I was hungry. They only food at the party was meaty stuff (other than some creamy artichoke dip) so I went for a walk around the part of downtown Omaha we were at (11th Street-ish) looking for dinner. I found a Mexican place and sat down for a nice quiet meal before the event started. About half way through I was joined by two others – both locals – who are at the conference and recognized me. Both are younger VCs so we had a nice conversation that was hopefully helpful and interesting to them. I learned a little about the scene in Omaha, so that was useful to me. And I enjoy small dinners a lot, so three people was perfect. And the cheese enchilada was exactly what I wanted.

We wandered over to the opening party around 8:30. I was already tired but I figured I’d give it a try. The entryway was subdued and pleasant as people were checking in and getting name badges. They were all a lot younger than me.

We then walked down a long hall and up some stairs into a huge room throbbing with music. Over the next 30 minutes, I said hello to a few folks I recognized, had a few others introduce themselves to me, and noticed that the room had filled up a lot. The music must have gotten louder because I could no longer hear anything anyone was saying to me without leaning over and putting my ear next to their mouth.

At one point I looked around and noticed that I was one of the oldest people in the room. It was 9:30 and I was tired. So I went home, did email for a little while, and went to sleep.

I’m heading out to the conference now and I’m looking forward to it. But I’m very aware of the age shift today for some reason. Interesting …

  • Fiona Schlachter

    I know exactly what you mean Brad. As an entrepreneur in Boulder, I was a little older than most but after moving to Dallas in 2011, I see a bigger age gap more often. But we gotta stick together, right? 🙂

    • Every generation needs a mentor. Now it’s your turn. That’s the way I look at age.

  • I can’t hear anymore either. 25 yrs in trading pits will do that. Omaha is a nice town. Tell Jeff to drop the Silicon from Silicon prairie!

    • I thought it was just called ” Prarie”. We need to search and replace with a blank.

  • StevenHB

    You’re facing one of those milestone birthdays this year

    • Yup. In seven months.

  • Ha ha ha! Welcome to the club

  • In my first company at one point we had around 100 people with an average age of 24. We were in a building right by what is now (and wan’t then) the trendy area of Silicon Roundabout in London. The other companies were much more traditional and couldn’t get their heads around this company that was just a bunch of kids 🙂

  • I feel like this all the time, lol. Its great to see the “next” class of folks stroll in and build anew. I always think have the same energy they have, applied differently, still working on the end goal, enable people, enable ideas, foster the scene, play that part you play.

  • Ha! Conferences do make you feel like that. I started my first company at 23. I remember going to a big meeting that I was holding at our law firm and being told: “Deliveries are on the floor below” Had many experiences like that.

    I never have liked loud music even in my fraternity days, but I have grown to not be able to stand it.

  • I had this happen to me a few years ago with a very big client. We did business prior, but only through email and phone, and it wasn’t until he met me, when the business stopped. I could tell immediately he was displeased with my youth, and that I didn’t live up to his ‘standards’. He wore every emotion on his sleeve, so it was quite easy to pick up.

    A shame. It was one of our largest accounts, and up to that point were doing great together. Maybe he was ashamed he dealt with someone much younger, or maybe he was jealous that he was working for someone else at his age, while I was running the show at mine.

    I definitely see a shift, but it’s not happening everywhere as quickly as in the established startup communities.

  • Ben

    Brad, looking back, what did you feel was the best way to build credibility at such a young age? (Apart from pure performance) I’m the youngest employee at my startup (18 people), and trying to establish myself as a leader in the company. Thanks.

    • I just did stuff. I listened a lot and learned from that. When I was wrong, I spoke up and owned it. And I worked very, very hard.

      • Ben

        Thank you for the reply and the advice.

  • Classic line: “I hung out and talked to some folks and then realized I was hungry.” Jeff’s a good guy, we reconnected last week.

  • Dillon Nicholson

    Brad, we met at the VIP party this past week and I only knew you as the guy with the shirt I wanted to hear more about. I had no clue you’d be the keynote speaker the following day. Your work ethic and success is impressive, but your natural humility will always be my favorite. Our chat and subsequently watching your talk at the conference has had a profound impact on me. Thank you for being you. 🙂

  • josh

    Hopefully a bartender saw this story and carded you… 🙂 I stopped wearing glasses in hs/college to hedge nerdiness. then our startup got acquired and i had to sell to gray hair fort100-types so I went back to the glasses for a while. Anything in particular you found easier as a twenty something or tweener, vs now and vice verca?

  • The Original Rick

    Yep, you’re pretty old… But no one would know it because you don’t ever call to say Hi!

  • I’ve found that I was always too young or too old.

  • Jeremy Riley

    Interesting post Brad. I have never been a part of the startup community and until recently wasn’t even very aware of it. I am 33 myself and now looking at starting my first significant company. In my experience genius comes in flashes and those flashes occur most often at younger ages. With youth comes the ability to view the world in a futuristic context. The older you get the more you view the world in the present. After a certain threshold is passed you begin to view the world in a historical context. Each of these views are restrictive in their own way. True visionaries see all three contexts at the same time. You can’t judge a trend by a single data point.

  • williamhertling

    When I moved to Portland, I was 25, and immediately got into the local music scene. I remember going to shows, mostly punk bands, where 90% of the audience would be between 15 and 25. I’d see some people in their 30s, and thinking: well, that’s neat, even though they’re older, they’re still cool enough to come out to see music. I hope I’m like that when I’m their age.

    And then there’d be just a handful of people who had…gray hair, and possibly lines on their faces and they dressed strangely. And I’d think: That’s weird. Why are these OLD people coming here?

    I’m pretty sure now that those people were my current age. Sigh.