Age: 23
Job: CEO, Engage, LLC Location: Los Angeles, California
Earlier this year, I watched ESPN's E:60 inspirational story of Jake Olson, former blind long snapper for the USC Trojans and current president of Engage, LLC. I thought he would be a great interview, but when I reached out, I was actually connected to his manager instead, Daniel, who is the CEO of the same company that he started before the age of 23. Daniel's interview is filled with honesty about starting a company at such a young age, how luck played a role in his success, and how he has shifted his perspective to achieve his goals.
What's your story?
I graduated from the University of Southern California, USC, in May of 2019. My freshmen-year roommate was a kid named Jake Olson who is completely blind and played long snapper for the football team, and I became his manager in January of our freshman year. He always had a decent flow of speaking appearance requests, but it was pretty manageable at the beginning. After snapping in a game for the first time, we just got absolutely flooded with appearance and speech requests and around the same time, I picked up another client that used to play in the NFL. I started to find that the people who were booking the guys I worked with were asking the same questions. Questions like “where does he travel from”, “what does he charge”, and “what does he talk about”? It was starting to overwhelm me as my list of clients grew. I started looking for ways to do the whole booking process online, mostly to make my life easier, and I found that there really wasn't one. Jake and I called a lot of athletes and agents we knew and found that the problem we were experiencing was very common. That led us to create Engage, which we tell people is like the "Airbnb for booking talent". The platform allows someone to do everything from finding the talent online and the experiences they offer to signing the contract. The processing payment is all done all online, so it has sort of digitized and streamlined the whole process.
Are you still managing Jake? Yes, I am. Engage works with almost 300 athletes at this point. A handful of them are guys I manage personally but we also work with a lot of other agents and athletes.
Looking back at your freshman year, are you surprised at what you're doing now?
Yes and no. I got incredibly lucky because essentially everything good that has happened is a result of me having the right freshman roommate. I remember as a third-grader, my parents asked me what I wanted to be when I grew up and I told them I wanted to be a professional baseball player. My dad said something along the lines of “I have seen you play baseball and you're not going to be a professional baseball player, but that doesn't mean you can't be involved with athletes or that you can’t be a part of the game. You just need to think about other ways to be involved.” It was the best advice I ever got. I’m pretty sure I was the only third grader that was reading books on different agents and understanding statistics of sports. I wish that my dad told me that in first grade because I lost two years of my life not doing that.
Did I ever think I'd be starting my own company? Absolutely not. I didn't really become interested in it until later in high school, but since a good opportunity presented itself, I took it. I'm only 23, so this is a time in my life where I can maximize my upsides and have no family to support. This is the time in your life when you can take on as much risk as possible. It was highly possible that the business would fail or that we would lose investor money, but the upsides of the business succeeding were way too enormous for me to pass up.
Can you talk more about the experience of starting your company?
It’s hard. This has been really, really hard. The first thing you need to do is get a lawyer, get advisors, and get an LLC filed. From that point, when it came to actually building the platform and building the business, I leaned on these advisors. The best advice I ever got was to possess extreme confidence in the merits of your ideas and extreme humility in your ability to predict the future. Basically, believe in what you're doing but also understand that you really have no idea what you're doing and you should seek out other people who do. Before we did everything, we called agents and made sure we understood what they wanted, so that shaped a lot of what we did. We dealt with a lot of fraudulent people at the beginning, so right away we knew we needed to focus on being transparent and ethical. A lot of what we did was based on listening to what the people around us wanted. Believe in what you're doing and seek other people who have done what you want to do.
What has been the hardest day on the job for you and how did you learn from that? The hardest single day is a tough question to answer. I would say the most important thing to have in business is perspective. I think I let little things get me down at the beginning when they shouldn’t have. I think the worst day was when we had a massive meeting with a talent agency, which actually went super well. However, there were a lot of things going on at the time, it was stressful, and we weren't where I wanted to be. I remember I broke down in front of our COO in the car and he helped me frame what I was going through in a different lens. He recognized that I was stressed, but told me to think of this whole thing like a ladder; if I wanted to get to the top of the ladder, I was realistically only on rung six or seven now, which was pretty good for how long we had been doing this. I realized that I needed to calm down a bit and think of all of the progress we had made.
From that point, I have tried not to let small things get me too down or good things get me too high, and it's the best thing I learned from that day. I have come out of it with a better perspective, but I still have things that are a struggle of course.
What would you tell someone looking to start their own company?
I think one of the hardest things to do is to start a company without partners because it's very isolating. Having partners at the beginning is why I started this company; I don’t know if I would have done it without them. I know they always have my back so I would never ever recommend trying to start alone. You have to find partners who are smart, who you have a deep level of trust with, and who will push you and compliment your skillset.
Can you tell us what it means to be a young professional to you? I think a lot of times, especially in startup culture, there's this idea that you have to work 100 hours a day to be successful, which isn’t true. I know a lot of startup founders think this too. The problem with a lot of young professionals, myself included, is we have the type of personality that will allow us to be consumed entirely by one thing. What's unique for me is that a lot of what I get to do for work is fun. I get to go to the Super Bowl and the ESPY’s, so I can’t complain, but balance is something I think about a lot in my life and is something I want more of.
You work with motivational figures. What is a lesson that you've learned from some of your athletes?
I think the thing that sticks with me the most is something Jake taught me. He has a pretty crazy life story about finding the setup in the setback. I think that’s actually a pretty unique insight that you don't hear other places. He talks about how it’s unhealthy to ignore your frustrations and that it’s okay to let those emotions in. Be frustrated, be sad, and see the bigger picture and the perspective. Look at Jake’s life; going blind was obviously his setback but that has also set him up to achieve things he never thought he would achieve.
What would you tell college students looking to join the workforce soon? A few things. I think our generation completely ignores mental health and they don't do enough to care for themselves. I work out every day, so why am I not doing the same for my mental health? I can’t stress that enough. On a lighter note, for people who don't know what they want to do, don’t think that it’s a bad thing not knowing what you want to do yet. It’s not a bad thing at all. You're 22 years old and if you don't know what you want to do, it's because you're interested in many different things and that's a really good thing. If you don't know what you want to do, figure out five or six fields that are interesting to you and go out and find people that do what you want to do and just have coffee with them. You don't need anything from them, but you want to learn from them, and you’ll start to build relationships so it all spirals from there. I did this all throughout college and it certainly paid off. Some of those people even became clients of mine.
The YoPro Know's Takeaways:
– When you're young, maximize your upsides; there is a chance things will fail, but now's the time
– Having partners at the beginning of a startup is key
– Find partners who will push you and compliment your skillset
– Be frustrated, be sad, but see the bigger picture and the perspective
– Possess extreme confidence in the merits of your ideas and extreme humility in your ability to predict the future
Check it out: Engage, LLC, University of Southern California, Jake Olson
