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I'm a millennial who relocated to Tampa, where I run my own business. I don't see myself leaving anytime soon.

Aug 6, 2023, 16:52 IST
Business Insider
Joe Steilberg with his business partner and roommate, Parker Klein. Courtesy of Joe Steilberg
  • Joe Steilberg, 27, moved to Tampa with his business partner for a job during the pandemic.
  • His startup has grown and he attributes its success to the city's supportive environment.
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This as-told-to essay is based on a conversation with Joe Steilberg, 27, co-founder of Twos, a note-taking and organization app. He moved to Tampa during the pandemic. The conversation was edited for length and clarity.

I've been a Florida boy for the majority of my life. I was born in Atlanta and my dad had different places of employment throughout my childhood. I lived in Miami from ages four to 13, and then in Jacksonville from ages 13 to 18, and that's where my family still is. I went to the University of South Carolina where I studied finance, and after, I lived in Texas. Now, I am in Tampa.

I founded Twos, a note-taking and organization app, with my co-founder Parker Klein, before we moved to Tampa. We received $1.7 million in venture capital funding from Tampa Bay Ventures this year, and plan to stay here for the foreseeable future.

I lived in a couple of cities after I graduated college in 2018, but nothing stuck

Straight out of college, I moved to Austin, mostly because I wanted to experience a big change.

The first job I took there paid $32,500, definitely on the lower tier of what is considered livable, but I actually didn't notice too much. Austin just felt like the perfect mix of it all — it was a bigger, trending city, that people thought highly of. I hadn't heard anything bad about Texas.

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Steilberg spent a year in Austin, Texas, after college. He moved to Dallas and shortly after, moved to Tampa. benedek/Getty Images

The problem that I noticed very quickly, though, was that I was having a lot of trouble finding my people, my group, because most of the time I was working. The only people I was meeting were at work. I realized that I didn't have a lot in common with the people that I was working with, and I had a lot of trouble figuring out how to break into these long-standing friend groups. Everyone seemed pretty closed off.

So I decided to move to Dallas. I went from working in residential real estate, to commercial real estate — so that felt like a leap up the ladder. I hadn't heard anything bad about Dallas, and I had a couple of friends already there. But the same thing happened, I couldn't find my group to break into. Then, COVID hit.

That gave me the chance to reset and ask myself, "Where do I really want to be?"

I moved to Tampa, and I have never looked back

I got a call about a private-equity position in Tampa, getting into the finance side of real estate, which is what I had always wanted.

As soon as I got here, it was day and night. It was such a warm and embracing environment. Everyone was like "let me introduce you to my friends. Let's go to the beach."

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Tampa, Florida. Chumbley Photography/Getty Images

I wouldn't even say that I have a strong affiliation with Florida. I actually was a little embarrassed about coming home. I didn't want to give off the impression that I was this homebody and I just needed to be on the East Coast.

But Tampa came knocking and it's the perfect combination of a big city like Miami, and a small community like Jacksonville. I love the weather and the people have been phenomenal.

The city is walkable and the weather is great

Before I moved to Tampa, my business partner and I were working on our startup on the side. During COVID, he was working remotely with Google from San Jose.

I told him I was moving to Tampa for the position in private equity. One day, he called me out of the blue and said "I love experiencing and moving to new places, can I come with you?"

That was music to my ears.

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We got a two-bedroom apartment in Tampa Heights. We pay $1,700 per month.

Clearwater Beach in Tampa. Ixefra/Getty Images

It's been phenomenal. It's next to this awesome little food hall. We are now a 15- to 20-minute walk to the water, to downtown, and a 15-minute bike to the collegiate area. We're a 10-minute walk from the University of Tampa. The walkability of a city, to me, is one of the most important, if not the most important part of quality of life.

We quickly realized that Tampa was a great place for a startup

For the first 12 months, we didn't really experience any of what the ecosystem has to offer. Until someone plugged us into this community called Embarc collective, it's a startup community with 150 startups.

Their campus is a beautifully renovated, repurposed warehouse. We were really nervous we weren't going to get in. But after three interviews, it was the perfect alignment of what we wanted and what they had to offer. We got in.

It has been an amazing community of young entrepreneurs who are just hustling to make what they believe in come true. It's a great coworking space, it gives great coaching. We realized that people in Tampa are very intentional about entrepreneurship.

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We would have been more inclined to consider alternative locations depending on investment opportunity, but Embarc and the community we found there, has kind of kept us here.

Joe Steilberg and his business partner Parker Klein in front of the startup collective, Embarc, in Tampa.Courtesy of Joe Steilberg

If you'd asked me two or three years ago if I had any idea of where I wanted to plant my roots, I would have said, "Hell no!" I would still want to live in Europe.

I still somewhat feel that way. I'm young, we're obviously taking a very unique career trajectory, we're not just climbing a ladder, we're trying to steer our way to the top.

I am trying to maintain this universe-of-opportunity mindset.

But that being said, I do absolutely love it here. If I could find a place that was within my budget, that was in a good location, I think I would buy it. Not only for myself, but as an investment, because I am really, really bullish on Tampa, and I think that it will have a similar growth to Miami.

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