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Inside the mind of a tech investor

Jordan Fliegel — an entrepreneur, angel investor and former pro basketball player — spoke at SBJ’s Sports Media & Technology conference about the value of an idea and the headaches for CEOs.

Behind every successful business should be one very simple idea. With CoachUp, it came from a personal experience for me as the founder of the company where I had a coach who helped me improve from being a bad high school player to being an OK college player and even worse pro player.   

 

With (CoachUp), it was creating a market. Airbnb, I wish I’d founded it. It’s an incredible company, of course. Everyone knows what it means, you need a place to sleep, you need a roof over your head. They just created a different way of doing it. With us, we really had to create a category. We had to explain what is private coaching — this is the best way to improve in sports. 

The idea has to make sense, but the ideas will change. 

Techstars Managing Director Jordan Fliegel said the investment “misses” on a good company hurt the most.Tony Florez

Fundraising sucks, and it’s something that you always do. As soon as you raise a round, you’re already starting to think about the next round.  

We didn’t have an accelerator for sports, and so I felt like we should. … We never had a dedicated accelerator (like Techstars Sports Accelerator). … Finally, this group in Indianapolis came together and really wanted to do it, put up all the money to do it, so the Pacers, the Colts, NCAA, Indianapolis Motor Speedway. 

We had 10 companies (in 2019) from eight
different cities around the world doing 10 totally different things, from athleisure, to fan engagement, to ticketing. They come, they spend three months with us. Not just with me, with all of our partners … and they hopefully form some partnerships with those partners. They hopefully develop their products, they raise money.  

It’s cool. Each company is such a reflection of the founder and their DNA because at the stage we’re investing, it’s a couple founders, an idea, a little bit of traction hopefully, but at the really early stage of businesses. 

Indy has got all the ingredients: pretty unique, amazing airport, great hospitals, schools, IU, Purdue, Butler. Notre Dame is in Indiana, right? Sports DNA, it’s the home of basketball. There’s a cluster, all of our partners, the NCAA being there, Indianapolis Motor Speedway, the Pacers and Colts. It’s a rare combination of talent coming out of the universities, probably the most business-friendly government from a state perspective in the country. No. 1, I would say.  

I’m friends with Wyc Grousbeck, who owns the Celtics. I couldn’t see the Celtics and the Patriots and the Red Sox getting together and doing something together. 

I don’t know why anyone would start a company in Silicon Valley right now. It’s so ridiculously expensive to hire an engineer. It’s so competitive, why would you be there?  

I want hustle and you have to have a technical co-founder who’s actually going to build the product, hopefully have someone who can do the marketing or the product or design side. An ideal founding team would [also have] a business-y, sales, charismatic person who’s essentially going to raise money and hire people. 

If you’re a non-technical founder, and you want to start a company, the hardest thing to do is not raising money. The hardest thing to do is to get a technical person to join your company.  

There’s a lot of eyeballs [in esports]. That’s cool. People talk about users and downloads or visits. … The valuations are very high relative to the revenue, and maybe that will change at some point in some way, but I’m a little bit more old-fashioned. I want to understand who’s going to pay, and how much are they going to pay, and how long will they pay, why are they paying, things like that. 

The misses are the worst. People think if you invest in a company and it fails, that’s bad. But it pales in comparison to the good ones that really work that you miss on.

Try to put the investor’s hat on. … 

As an investor, you’re automatically thinking about risks. There’s the team risk, that it’s not the right team or that they’re going to break up, or they’re not going to be able to scale the business and you’re going to have to replace them. … There’s a product risk. There’s an execution risk. I think the best things you can do is, basically like a snowball, you’re pushing down a hill. You try to do just one thing, and then another, then another.

If I go meet someone, I would never ask for money right away in that interaction. I try and explain what I am, what I’m doing.    

You raise a little bit of money. Just enough to hire the people you need to execute on a certain thing to de-risk the business. That enables you hopefully to raise at a higher valuation, hire more people, build more product.

A good CEO is really responsible for hiring a great team, protecting the vision and the mission, and not running out of money. If you’re doing your job well, it should almost feel a bit easy, with the exception of when you have to go after more money, which is always hard.

You really get a great team, and you’re able to delegate.  

You have to be really conscious of what you say when you’re leading a company because people think that whatever you talk about the most, that’s what the most important thing is for the company.  


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