Jake Olson

It is really important to know your own network and how they can provide value to you.


Jake Olson is the co-founder and president of Engage. Jake has a truly incredible story that has been well chronicled and featured in just about every outlet from ESPN to CNN to the New York Times to the Wall Street Journal to the Washington Post. At 8 months old, he was diagnosed with a rare form of eye cancer, retinoblastoma. The disease claimed his left eye before the tender age of one and in November 2009 Jake lost his right eye after battling the cancer for 12 years.

Jake has not let blindness stop from achieving any of his goals. He attends the University of Southern California where he is a senior majoring in business. He also played on the school’s football team as a long snapper, and during USC’s game against Western Michigan on September 2nd, 2017, Jake made history as the first completely blind player to ever play in a Division I football game. Jake has used his fame to inspire others and travels around the country as a motivational speaker. He is also a member of the President’s Council on Sports Fitness and Nutrition, has written two books, started his own charity, and golfs in the mid 70s.

Where did the idea for your company come from?

The idea for Engage came from my experience as a speaker. After I played in my first game, I got absolutely flooded with speaking requests. My manager started looking for a way to do it all online, and we found that there was not a way to do the process digitally. On top of that, there was no way to book me for more than just a speech. I called several of my athlete friends, and found that they experienced the same problem. That led to us founding Engage, a platform that completely digitizes the process of booking talent for an experience.

What does your typical day look like and how do you make it productive?

My typical day would have me waking up at 7am, eating a healthy breakfast, and catching up on emails. 8am-4pm is generally filled with meetings, calls, and interviews. I try and take a half hour for lunch every day away from my computer or phone. In order to maximize my productivity, I make sure to eat three meals a day, sleep at least 8 hours, and I exercise every single day after work. Feeling physically healthy is really important for productivity.

How do you bring ideas to life?

All of my ideas come from a problem I face. After I identify a problem, I come up with a proposed solution. From there, I talk to friends and colleagues in a similar position to see if the problem is real to them and if they like my solution. After that I do thorough market research to see what solutions are already out there and what the competition looks like. If I find that the problem is real, my solution would be effective, and that there is not much competition, I then seek the right partners and investors to bring it to life.

What’s one trend that excites you?

I am very excited by the experiences trend. More and more millennials would prefer to spend their money on a unique experience, as opposed to a high-end product.

What is one habit of yours that makes you more productive as an entrepreneur?

I am willing to work at any hour of the day. If something needs to get done, I will do it even if it is a weekend or holiday. Every second counts, and I rarely (if ever) take days off.

What advice would you give your younger self?

I would tell my younger self to work hard to maintain a big picture view of your company’s progress. It is easy to get bogged down in the day to day details and feel like you are not making the progress you want. If at least once a week you focus on stepping back and looking at where you were a month ago, six months ago, it will put in perspective how far you’ve come and that has a very calming effect.

Tell us something that’s true that almost nobody agrees with you on.

Soccer is a stepping stool sport.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

As an entrepreneur, you are constantly dealing with requests, issues, and different opportunities that come up. In order to not get overwhelmed, I make sure to prioritize everything that comes in. My general rule is this, if I am dealing with an investor, client, or key stakeholder, I work on their time. If I am dealing with someone who needs a favor or my help with something, I work on my time. Everything gets done, but that way I maintain some control of my schedule.

What is one strategy that has helped you grow your business?

It is really important to know your own network and how they can provide value to you. Being able to ask for the right thing from the right people has been key to growing Engage.

What is one failure you had as an entrepreneur, and how did you overcome it?

Engage is really my first start up so I don’t have any significant business failures, but there are plenty of day to day things that do not go our way that I learn from. I never view a failure as permanent and try to understand what went wrong and how we can use it to grow.

What is one business idea that you’re willing to give away to our readers?

Anyone who can figure out how to translate the thoughts of a dog into coherent human language will be a billionaire.

What is the best $100 you recently spent? What and why?

The best $100 I recently spent was a steak dinner with my girlfriend. It’s always nice to treat the people important to you to a nice meal.

What is one piece of software or a web service that helps you be productive?

This is probably very specific to the blind community, but I use voiceover software on my iPhone. It allows my phone to read me all my texts, and constantly lets me know what I am clicking on. Without it, I probably would not be able to use my phone.

What is the one book that you recommend our community should read and why?

I would recommend The Lean Startup, by Eric Ries. It is filled with incredibly practical lessons about entrepreneurship and is a fun read as well. Even though it was originally written in 2011, many of its lessons and insights are still valuable.

What is your favorite quote?

“Don’t take life too seriously, you’ll get out alive” – Elbert Hubbard

Key Learnings:

  • Find the right partners. Growing a company should not be done alone.
  • Do not shy away from adversity or setbacks. Use them as setups for something greater.
  • Be responsive to emails, texts, and calls. Every second counts.
  • If you have to invent the problem your business solves, you are probably doing something wrong. Identify the problem first, then come up with a solution.