The Truth About Early-Stage Investing w/ Kelly Iannone

Summary

In this episode, Brandon Reed sits down with Kelly Iannone—former Disney executive turned full-time investor—to explore her evolving journey into early-stage startup investing. With a foundation built on disciplined stock market investments and real estate syndications, Kelly shares how her perspective broadened to include tech startups, thanks to a well-timed opportunity that emerged through her real estate network.

Kelly discusses the myths she’s had to unlearn about trust, risk, and diversification. She breaks down her investment strategy, from protecting her downside to filtering startup opportunities based on founder experience and long-term market trends. With refreshing humility, she opens up about how early she is in her startup investing journey, while providing practical insights into how others can get started too.

This episode offers a balanced, candid look into what it means to become an angel investor without being in Silicon Valley, and how any professional can diversify their portfolio with intentionality, access, and a strong network.

Takeaways

1. Early exposure matters – Kelly’s understanding of investing came from parents who talked openly about money and emphasized long-term financial planning.
2. You can’t do it all yourself – A key mental shift was learning to trust others, especially when investing in vehicles where she doesn’t control the outcome.
3. Worst-case scenarios are critical – Before investing, she always asks: what’s the worst that could happen, and are we okay with that?
4. First startup investment was in real estate tech – Her entry into startups came through a trusted connection in the real estate space, aligning with her expertise.
5. Track record trumps hype – Kelly looks for founders who have successfully built and exited companies, especially in areas where she isn’t a technical expert.
6. The person matters more than the pitch – Understanding the ethics, mindset, and motivations of a founder is more important than projected returns.
7. Diversification with intent – She divides her portfolio across asset classes: real estate for cash flow, equities for long-term hold, startups for potential home runs.
8. Angel networks didn’t feel like the right fit – Kelly has chosen to rely on curated opportunities from her network rather than broad investment platforms.
9. Start small, start now – One of her guiding principles is to take action early, even with small capital, and build from there.
10. She’s still learning—and that’s okay – Kelly’s honesty about being new in the startup space makes this episode particularly accessible for aspiring investors.

Chapters

• [00:00] Getting to Know Kelly Iannone
  • Kelly shares how she and Brandon first met through Disney and a real estate investing meetup, and the broad scope of her investing experience.
• [01:29] Why Investing (Even in Risky Places) Made Sense
  • Growing up in a household that emphasized 401(k)s and stock investing, Kelly learned early that putting money to work is essential.
• [04:42] The Myth of Doing It All Yourself
  • Kelly explains why trying to control every part of the process is unrealistic and how trusting others is essential to scalable investing.
• [06:48] First Big Risk in Real Estate Syndication
  • A $30K investment into an RV park syndication became the test case for trusting operators and the power of passive investing.
• [09:56] What Most Investors Aren’t Asking
  • Kelly argues that investors focus too much on returns and not enough on understanding the founders or operators themselves.
• [11:39] When You Don’t Know the Founder Directly
  • In startup deals with stealth founders, Kelly explains how she leans on her network’s credibility to vet the opportunity.
• [14:58] What Drew Kelly to Startups
  • Her first tech startup investment happened through a trusted contact, and she saw a clear market fit based on her own expertise in real estate.
• [21:22] How Startups Fit in Her Portfolio Strategy
  • Kelly breaks down how startups serve a very different role than real estate or equities—aiming for growth, not cash flow.
• [26:10] Angel Networks: Why They Didn’t Fit Her Style
  • Kelly reflects on why she hasn’t used angel investing platforms—preferring vetted, high-trust deals through personal connections.
• [33:14] What’s Next in Startup Investing for Her
  • Kelly shares how she’s vetting her next SaaS investment opportunity and how she’s evolving her filters and frameworks.
• [37:58] Starting Over with $1,000 and a Laptop
  • Kelly says she’d start by identifying her goals and then getting in the room with the right people in that space—relationships first, always.
• [40:42] One Quote to Live By
  • “Start small, start now”—Kelly’s philosophy for both investing and life, rooted in clarity, discipline, and long-term thinking.