Kasey Kaplan

An individual who has had a huge impact on my life is my high school swim coach Rob Rooney. When I joined the team, I could barely swim. I was in horrible shape, and I knew nothing about the sport — it was humiliating. He pushed me past the point I thought I could go. We would practice twice a day during the season even when there was a foot of snow outside and it was below zero. He taught me what it meant to be dedicated to something and not quit regardless of how bad it seemed at the time. Because of him, I developed mental toughness and understand what perseverance means.

I had an amazing boss named Wes Weiler at the first startup I ever worked at. To this day, I have not met someone who could motivate a group of people like Wes. He had this philosophy called “Left Foot, Right Foot.” The idea was that if you woke up in the middle of the woods and had no idea where you were, the only way to get out is if you “left foot, right foot” until you make it to the road. He applied this to both business and life. He believed in three fundamentals to success: Everyone needed to be accountable for their own actions, perseverance is key, and don’t expect others to do something you’re not capable of.

Not staying focused. There are always new and interesting opportunities. It’s so easy to get distracted and pulled off course from your company’s core focus. It’s good to be aware of potential opportunities, but it’s essential to execute on what will keep the business running or else you just wind up spinning your wheels and going nowhere.

I’m normally on the phone before I get in the office, but once I get in, I like to spend time talking to my team about how their nights were. I think little things like this create a good rapport and help them feel open to talking to me about issues, as well as build a fun and inclusive culture.

The deal is not done until the money is in the bank. In other words, regardless of verbal commitments or even signed contracts, it doesn’t count until you get the cash.

On a business level, have a solid understanding of your business and how it fits into the industry you serve.

Success means completing something from start to finish. In startups, just like a race, the two hardest parts are starting the race and crossing the finish line. Everyone is motivated by different things and I am a very competitive person, but I find that I compete against myself more than anything else. If I can achieve the expectations I’ve set out for myself, I consider that a success.