Frederick Hutson On How He Secured Investment For Pigeonly With All The Strikes Against Him

Kwame Som-Pimpong
Written by Kwame Som-Pimpong
Frederick Hutson

In Part 2 of his conversation with GHOGH podcast show host Jamarlin Martin, Frederick Hutson shares some foundational keys to keep in mind when securing investment for your venture, building a team, making faster decisions and working with people you don’t like. 

Hutson is CEO of Pigeonly, a technology platform that enables people to remain in touch with their loved ones who are incarcerated. A former Air Force aircraft electrician, Hutson was charged with marijuana distribution and incarcerated for five years. He used his personal experience in prison to solve a problem for millions of people — how to better communicate with loved ones who are behind bars.

While in prison, Hutson sought out mentors in the prison population for advice on how to do things like build financial models and vet his ideas within a framework.

Securing investment for your venture

Hutson shares the story of securing his initial investments for Pigeonly. He was able to secure those early checks because he showed that he was solving a real problem and the market agreed with the problem he was trying to solve. In Part 1 of his conversation with Jamarlin, Hutson talked about how he was the only startup in the NewMe Accelerator who had paying customers — validation from the market on the problem he was looking to solve.

Listen to GHOGH with Jamarlin Martin | Episode 54: Frederick Hutson

Part 2: Jamarlin talks to justice-tech pioneer Frederick Hutson, who founded Pigeonly to create communications products for inmates and their families. They discuss how he raised capital, the importance of focus, and spending too much time perfecting the product before launch. They also discuss Jay-Z’s blueprint for parting ways with team members via his break-up with Damon Dash.

Have you had trouble finding customers to validate the venture you’re looking to build? Here are some resources:

Secondly, Hutson pointed out that his second investment didn’t happen until several weeks after first meeting Brian Dixon, partner at Kapor Capital. Hutson was able to secure that investment after showing progress over time which helped Dixon connect the dots and see that Pigeonly was worth cutting a check.

Trying to figure out how to show consistent progress for potential investors? “Measure What Matters,” a book by Silicon Valley legend John Doerr, offers the framework of objectives and key results to map out your path and methodically execute along the way.

Eliminate what prevents you from learning quickly

In discussing mistakes he made building Pigeonly, Hutson talks about how he spent too much time trying to build the perfect product before releasing it to the market. He highlighted how getting a product to market as quickly as possible aids the learning process.

Further, Hutson stressed the importance of discipline — ensuring you’re focusing on your core product or customer rather than trying to build a bunch of different products that meet multiple needs.

Both of these mistakes slowed down the business. To avoid slowing down your business, the lean startup methodology has proved helpful, ensuring startups remain disciplined in focusing on the customer and getting the feedback they need to continue building their venture.

Build a team as soon as possible

Hutson shared the importance of building a team around you sooner rather than later as another key to building a successful venture. He often found himself as the bottleneck because he wasn’t willing to let go. As he let go, he was able to focus more of his energy on his strengths and put the business to run as efficiently as possible.

Looking to build a team? Here are some resources to get you started:

Frederick Hutson on how to work with people you don’t like or agree with

Finally, Hutson points out the strength in being able to work with people you don’t necessarily agree with. From his point of view, it is going to be difficult for you to build something at scale if you’re not able to work with people you don’t necessarily like. 

Looking to build your ability to work with others? Here are some ideas for how to develop that muscle:

Building a new venture is hard work, but there are boxes you can check to put yourself in as good a position as possible to win. Hutson stresses that if he could do it with all the strikes he has against him, then you can too. Let’s GHOGH!

Kwame Som-Pimpong leverages relentless research, a knack for connecting dots, human-centered design approach, and effective communications strategy to help organizations realize their strategic objectives. Over a 10-year career, Kwame has supercharged grassroots political organizing efforts, assessed the effectiveness of U.S. federal agencies, managed an international program, founded a digital media startup, and advised government agencies on delighting their end-users. He earned a BA in Political Science from Davidson College and Master of Public Administration from the University of Georgia. He can be reached at kwame.som.pimpong@gmail.com.