It had been 365 Days since meeting Mr. Neal Dempsey in person at Neal’s Running Start in San Francisco. And in 365 days, your life can be completely transformed. On day 1, one year ago, I was nervously arriving in San Francisco, having taken the biggest leap of my company’s life. I had committed to spend a month in San Francisco under Neal Dempsey’s mentorship to see if I could take my company to new heights. On that 365th day, I was standing with Neal in front of MBA students at the University of Washington Foster School of Business sharing my story on how I went from entrepreneur to a CEO of a fast-growing company with investors, Fortune 500 customers and offices in two locations. In 365 days, I went from mentee to mentor.
These students were smart, engaged, and impressively enough, some already had startups underway. We had taken different paths to entrepreneurship. The UW pushes its students to be founders of companies, and brings in mentors like Neal and the vast successful organizations in the Seattle area such as Amazon, Boeing, Microsoft and Starbucks. Saskatoon is a different story. There aren’t many mentors from big tech companies waiting to offer guidance to Saskatoon entrepreneurs and start-up companies.
But whether you come from Seattle’s wealth of success or Saskatoon’s hard work, get-it-done work ethic, everyone has the same questions – what does it take to be a CEO and run a successful company? That’s why I came to help.
Below are a few questions I wanted to highlight from our almost 2 hour conversation:
What do you look for in a CEO?
- Neal: “I look for three things in CEO. Do they have personality, passion, and perseverance? It’s always a combination of these things, never just one.”
What makes a great company?
- Neal: “I can tell you all of my best investments have never had a clear straight path to success. In fact, some of my best investments almost didn’t make it. We asked ourselves do we invest more? Do we shut it down? See, it’s more like a rollercoaster with ups and downs.”
How would you suggest building up your leadership team?
- Katherine: “I have always hired for our biggest pain point at the time in order to improve the team and take that next step. I have a Sales and Marketing background, my first hire was our CTO, Romeo. Genius developer.”
What do you look for in an investor?
- Katherine: “I look for a few things, but mostly how do they treat people, and what experience do they have in our space. Money is important but both the investor and entrepreneur should walk if it’s not the right fit on other levels.”
Is it lonely being a CEO?
- Katherine: “What a great question. Yes. Yes. It totally is. However, since the Neal’s Running Start program the four of us have been able to create honest relationships where we can go to each other and say , “Woah, I have no idea how to solve this. Do you guys?” Mentorship happens at all levels — with all people.”
What percentage of CEOs can take it all the way?
- Neal: “You have to understand that running a business is a long and difficult marathon that can go 10 – 12 years. Some of our CEO’s just get tired, or what I call “founders fatigue” and don’t want to do it anymore. It’s hard. I would say only a small percentage of founders can take their startup to an initial liquidity event and that is if they decide they even want too.”
Do you have a number?
- Katherine: “A phone number? Sure, I haven’t been asked for that in a while. Just kidding, I don’t have a magic number for selling. The sky’s the limit, and I will worry about it when we get there. Setting a goal can also be setting a limitation.”
Overall, my time at UW was welcoming, refreshing, and inspiring. It was so fascinating watching the students come alive on how they were turning their ideas into a reality. This is what makes the business world go round.
I mentor at the University of Washington and in Saskatoon with our burgeoning start-up community because people like Neal were kind enough to help me along the way. I’ve come to learn the value of community, like the strong one here at the University of Washington. Just 365 days ago, I didn’t know the names of the tech start-up founders down the hall from me in Saskatoon. Now, we’re a thriving community, helping each other learn and grow.
Neal embodies that sense of giving back and community. As I walked the campus, I couldn’t help but see Dempsey Hall and Dempsey Indoor. Neal is extremely modest and humble about his success, but his presence, like his name on the campus buildings, is felt and appreciated.
I’m looking forward to visiting the UW students again, and following up on their journey. Who knows how far they’ll come over the next year. 365 days can change your world.