A Street Corner Moment

Jason Lesh

Jason Lesh

Those of you that know me well have heard me say, probably more than once, that during the life of a business there are less than a handful of times where there exists an opportunity to significantly step on the gas pedal. I am proud to say that for our account, Pilot is experiencing one of those moments. I am excited to announce that we have acquired Activate Leadership, a leadership and organizational development consultancy, and it's founder Rick Thomas has joined our firm as Principal and Director of Human Capital. To fully explain the why behind the acquisition, a bit of backstory helps. Three and a half years ago I was standing on the street corner having just sold an amazing company. In my pocket was a cashiers check for more money than I ever had before and yet I was full of self-doubt and a whole lot of questions. What did I just do? How will this affect my family? What will I do next?

It was in the answers to these questions that I learned what a great teacher hindsight is. I eventually connected with Nick Fisher and we founded Pilot Wealth Management to not just help invest client's money, but help them with some of the most important decisions of their lives. To not only help them when they have their street corner moment, but also be standing with them in the years leading up to it, and far into the future.

The overriding goal for Pilot is to create lasting impact for our clients. We do this. But when we started Pilot, I thought we were different because we actually focused on investing. We are phenomenal investors (in my humble opinion), but I realized this was only one of the reasons why our clients decided to work with us.

What hindsight has taught us is our clients choose to work with us because they trust us. And because we empathize with them. We truly do have (and require) an intimate relationship with our clients. My experience with startups and financial strategies only goes so far. And Nick's immense experience investing in the markets was still not enough. I concluded that whether our clients knew it or not, they were hiring us to help them achieve their dreams.

Again, hindsight speaks loudly here, and we have learned that simply managing and speaking to the needs of financial capital isn't enough for our clients to achieve their dreams. It's necessary that we acknowledge and invest in the human capital of our clients as well: the relationships, the shared goals and sense of purpose. In helping define the values and strategy, husbands, wives, business owners and professionals know that they are on the right path. In this we truly begin to achieve significance in the work.

Enter Rick Thomas and Activate Leadership. This is what he does. And under the umbrella of wealth management, this is what we do. The power of our combined services and backgrounds is incredible. We have collaborated and worked together with a handful of clients over the past year, and after many months of discussions, retreats and strategy sessions, we can finally share our excitement with you.

My goal for this firm is to create lasting impact and to have deep and meaningful relationships with our clients. We do that already which is why I love my job. And adding Rick to the team only strengthens what we have to offer.

Thank you for your continued support and I look forward to introducing you to Rick in the near future.

All the best,


Jason Lesh, President & Managing Principal