Steve MacDonald: The Art & Science of Angel Investing


Angel investing is part art, part science.

Oftentimes you trust your gut when deciding to put your finances, effort, and time into a company. In the early stages, you partner up with friends and family, and you choose your investments based on whether you like those people or not. But, as you move further down the spectrum, it becomes more science.

In today’s episode, Steve and I discuss how to choose the companies you want to financially support, and also, some of the red flags for angel investing.

Steven MacDonald is a serial entrepreneur who founded, among others, TechHealth and myMatrixx – the first web-enabled pharmacy benefits manager. The successful experiences in the entrepreneurial world led Steve into angel investing and now he is a Partner and a Board Member at Florida Funders and he helps find, fund, and build the next generation of technology companies in Florida.

So, listen to Episode 06, to learn, from an expert in the field, what are the rewards of angel investing and how you can actively be involved in the companies you want to support.

Listen on Apple Podcast

Questions I ask:

  • While you were building myMatrixx, what were some of the things that you learned, lessons learned as an entrepreneur, that maybe even help you as an angel investor today? (04:00)
  • When and how did you start angel investing? (05:31)
  • What do you look for in a founder? What is it that excites you? And why you want to invest in this founder and not that founder? And is the founder the most important thing? (11:38)
  • What are some of the things that you, as a board member and investor, can help a company with? (17:05)
  • What differences do you see between the startup community and investing in Silicon Valley, San Francisco versus Florida? (20:45)

In this episode, you will learn:

  • Steve’s background in the business world. (01:54)
  • The reasons angel investing is viewed as part art, part science. (06:03)
  • What to look for, when considering to invest in a company. (10:27)
  • Our processing power and Moore’s law – the two essential components that spin the wheel of technology advancement. (14:46)
  • Steve’s favorite companies that he has invested in. (20:00)

Related Stories

  • Brad Feld: Investing in Startups

    Brad Feld: Investing in Startups

    Brad Feld, an avid ecosystem-builder, tech entrepreneur, and early-stage investor for over 35 years shares his insights on the venture capital, startup, and tech community...

  • Joey Levy of Betr talks about micro-bettting

    Joey Levy: Building A Betr Company

    Florida-based entrepreneur Joey Levy adheres to the philosophy that providing an optimal customer experience is paramount to any company's success. Levy has used this belief...

  • Lakshmi Shenoy at Embarc collective

    Lakshmi Shenoy: Building A Tech Community

    Lakshmi Shenoy's road to success in building thriving tech communities began by learning and applying principles taught by her parents. Today, she continues to incorporate...


Subscribe to the Florida Funders Newsletter to stay close to what we're building.