The Game Plan

Stewart Bradley — NFL Linebacker turned B2B-Investor Shares Alternatives to Venture Capital

The Game Plan

Show Notes

SaaS investor and former NFL linebacker Stewart Bradley joins The Game Plan to share his life journey and evolution from football player to sophisticated tech investor.

Shortly after his seven-year career with the Philadelphia Eagles, Arizona Cardinals, and Denver Broncos came to an end, our guest chose a different path; joining Goldman Sachs as an investment banking analyst in their esteemed technology media and telecom (TMT) group. Stew shares with us his decision process in choosing this path, and why he ultimately opted to go into banking versus pursuing an MBA.

Today, our guest is General Partner and Co-Founder of El Cap holdings where he is carving a unique path in the crowed software investment landscape. Stew shares with us the currency, beyond capital, with which he is building the fund. We also explore his investment thesis and the types of companies he looks to back.

Seasoned investors familiar with enterprise software and the SaaS landscape will especially appreciate what Stewart has to say about investing in "opinionated software products".

We also discuss the power of effort and focus and how these two attributes over the long term have helped lead our guest to success both on and off the football field.

Learn more about Stewart Bradley's investment approach by visiting El Cap Holding's website at https://www.elcapholdings.com/ or emailing [email protected].

Follow The Game Plan on Twitter (@thegameplanshow) and Instagram (@gameplanshow) for show news and updates, to recommend guests, and for bonus content!

You can also follow co-hosts Jay Kapoor (@JayKapoorNYC) and Tim Katt (@Tim_Katt) for all things sports, media, tech, and venture capital.

More from The Game Plan

May 3, 2022

Human beings have been collecting non-utilitarian items for millennia. It just so happens that with the advent of the digital age, we're now able to collect items from around the world and display them digitally for fellow collectors all over the world to admire as well. Add to this Digital Collectibles, like NFTs, and you've got a space ripe for tech innovation.

Mar 15, 2022

If you listen to this show regularly, you know that the shifting interest of athletes from endorsement to ownership is something we talk about a lot. Well, it turns out that in the last few years, athletes aren’t the only ones that are thinking about how to get ownership in the brands, companies and financial institutions they help build as early adopters, micro-influencers, or simply as customers.

Mar 2, 2022

In many ways, Bennie Fowler's story is the epitome of resilience and exactly the kind of journey we love sharing onThe Game Plan every week. Bennie had tremendous success in college at Michigan State and like many of his fellow players, expected to hear his name called during the NFL Draft. Unfortunately, that announcement never came.

Feb 15, 2022

Podcasting and social audio as a viable business has seen explosive growth in the past decade, the last few years especially. With Spotify having spent over $1Bn to acquire both tech and talent, apps like Clubhouse raising at multi-billion valuations, and even platforms like Twitter launching their own social audio Spaces, we felt this topic deserved a deeper dive.

Feb 1, 2022

In this week's episode of The Game Plan, we venture into the wild, wild west of the internet: Digital collectibles, NFTs and Web3. What does it mean for athletes, how is it changing how athletes think about their personal brands and ability to monetize their work on and off the field, and who the key stakeholders in this new tokenized world are and will be.

See all episodes →