Skin in the Game VC Podcast

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. 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)More about Florida Funders:WebsiteOur Investment ProcessLinkedIn Hosted on Acast. See acast.com/privacy for more information.

Show Notes

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. 


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)


More about Florida Funders:

Website

Our Investment Process

LinkedIn


Hosted on Acast. See acast.com/privacy for more information.

What is Skin in the Game VC Podcast?

Florida Funders Managing Partner and "Skin in the Game VC" podcast hosts Saxon Baum & Tom Wallace believes that entrepreneurs are game changers and that the companies they envision, create and build make the world a better place. FLF is a hybrid venture capital fund and investor network that discovers, funds, and builds early-stage technology companies. We combine a $300M+ venture platform with 2,000+ accredited investors to back breakout founders in B2B software, fintech, AI, health care, and cybersecurity. Beyond capital, our team of serial entrepreneurs and investors provides operating expertise, strategic introductions, and a nationwide support network that helps founders win. By unifying venture capital with an engaged investor community, we deliver exceptional outcomes for founders and LPs alike. This podcast was envisioned to educate, connect and activate accredited investors to get skin in the game and invest like a VC.