The investments industry is wrought with decisions—and they’re never easy to make.

Stuart is a native of Tampa, Florida. He moved around, went to school at UVA, but eventually made his way back home to Tampa. Ever since then, he’s been an active investor in technology companies. Some of his investments were incredibly successful and some were not. Each investment he made, however, provided him with new, valuable experience to learn from for the future.

On today’s episode, Stuart shares both these successes and failures. He shares his personal journey as an investor along with some of the nitty-gritty details of how he makes those big decisions and his own journey along the way.

So get ready to learn some new strategies regarding making investments and what to watch out for.

Listen on Apple Podcast

Some Questions I Ask: 

• When and how did you start angel investing? (4:27)
• What do you look for in an investment? (5:50)
• What deal size do you look for? (8:00)
• What red flags do you look for when considering an investment? (11:12)
• How do you interpret the market when making investments? (12:57)
• What’s the most important part of due diligence? (20:31)

In This Episode, You Will Learn: 

• How Stuart made his first investment. (2:27)
• Why focusing on the entrepreneur when choosing an investment is crucial. (5:55)
• Why it’s important to be as real and authentic as possible in investment conversations. (11:24)
• How the market determines the potential for the business you invest in. (13:05)
• When to put more money into a company, and when to shut it down. (15:26)
• Why some of Stuart’s investments failed. (16:01)
• About the roles of communication and coachability in the investment industry. (19:52)