Interview With Will Weatherford

Former Speaker of The Florida House of Representatives turned private investor values leadership, focuses on regulated markets for innovation, aims to make a positive impact, stays focused, and emphasizes the importance of strong leadership teams.

What motivated you to get started in private investing?

‍When I left public service after serving as The Speaker of The Florida House of Representatives (in my early 30’s) I was looking for a new challenge. I always had an entrepreneurial mindset and I was looking to find a way to have impact while also building something special with my brothers.

What is the single most important thing you value in an investment opportunity?

Leadership. It starts and ends there. Great leaders figure it out and have grit to fight through the tough times and not sit on their laurels during the good times. It’s all about leadership!

What are the best innovation themes that you see in the market today? And how would this have an impact on Weatherford Capital’s long-term goals?

There are so many. We focus a lot on regulated markets where innovation is lagging. Think Government, Insurance, Finance, etc. We believe that these end markets need and are destined to innovate and be disrupted.

Beyond economic return, what kind of impact do you hope to make with your portfolio?

My partners and I are all former college football players so we are very competitive but we always seek to “win the right way.” This means we look to help others by the companies we invest in. One example of this is our Govtech focus. Pew Institute has a study that tracks people’s trust in government over the last 60 years. It has steadily declined since 1960 when trust in government was at 75%. Today, only 20% of Americans trust their government. We believe there is a role that technology can play to bring the trust back.

What’s the most pressing challenge or pain point in managing your day-to-day private investment activity?

Staying focused on the priorities. Like any endeavor, there are always distractions and things that can take your focus away from the main thing. Staying laser focused on your goals and priorities is very challenging but absolutely essential for success.

What is the hardest investment lesson you’ve learned and/or the biggest investment mistake you’ve made?

This goes back to the question earlier about what we value most. Leadership is everything. Make sure the leadership team is intact and is positioned for success. Many CEOs and founders don’t see their own weaknesses and it’s incumbent on us to be radically honest with ourselves and our partners to make sure we have the right team in place to execute the mission of that business.

What are your favorite industry information sources and/or services?

We use Salesforce a lot and really like the functionality of Pitchbook, Preqin and Tegus. The information is out there and there are great service providers who can help you chase it all down.

Please leave us a book recommendation.

GRIT by Angela Duckworth. She speaks about how important it is to push through adversity. It is the greatest indicator of how likely we are to reach our potential.

What’s your favorite non-business interest or hobby?

Watching my kids play sports and reading.

What’s your take on the private market overall?

Scored: 7

I am an optimistic person in the long term. Over time, human ingenuity wins out. But nothing is ever perfect and up and to the right forever. Therefore, I would put myself as an 7. Private markets will do well over the next 10-15 years but you can’t always foresee what bumps you most overcome along the way. This is where the GRIT comes in 🙂