Surviving Booms and Busts: How Gary Shields Separates Real Value from Hype in the AI Era | Ep. 159

What can five decades of booms and busts teach dealmakers about today’s AI boom? On this episode of The M&A Mastermind Podcast, host Nick Olsen talks with Gary Shields, chairman and managing partner of Nassau Street Partners. Gary’s career began at Crédit Lyonnais and ran through L.F. Rothschild, Robertson Stephens, and The Chicago Corporation. He also helped run a healthcare company, invested in more than 50 venture-backed companies, and served on more than 20 boards. He compares the 1987 crash and the dot-com bubble with what he calls the “AI tsunami.” He also explains why revenue and earnings still separate the winners from the hype, and how his firm uses AI in every part of the deal process.

In This Episode, You’ll Learn:

  • How Gary went from Crédit Lyonnais to Wall Street, venture capital, and founding Nassau Street Partners
  • What it taught him to work on the operating side of a company, and how he sold it to Eli Lilly in the middle of an IPO
  • Lessons from Robertson Stephens and the “Four Horsemen” era of technology banking
  • Why Gary likes hiring athletes to build a winning team
  • What the 1987 crash and the dot-com bubble can teach dealmakers today
  • How the semiconductor led to the 1980s and 1990s tech boom, and how that compares to AI
  • Why AI companies that generate real revenue and earnings will be the winners
  • Why clients should include AI in their story without leading with it
  • Whether buyers are paying a premium for companies that use AI
  • How Nassau Street Partners uses AI for deal sourcing, buyer targeting, and keeping teasers anonymous
  • Why AI won’t replace investment bankers, and why you shouldn’t build a deal on what ChatGPT says

About the Guest:

Gary Shields, CFA, is the chairman and managing partner of Nassau Street Partners, a global capital advisory firm headquartered at 40 Wall Street in New York. He is also chairman of investment banking at Nassau Street Securities LLC, Member FINRA/SIPC. Gary’s five-decade career includes:

  • Roles at Crédit Lyonnais, Technological Investors, L.F. Rothschild, and Robertson Stephens
  • Head of healthcare investment banking at The Chicago Corporation
  • Number two executive at Integrated Medical Systems, where he negotiated a strategic alliance with McKesson and led the company’s sale to Eli Lilly
  • Co-founder of the investment bank Flemming, Lessard & Shields
  • Founder of AvTech Ventures, where he managed investments alongside Gateway founder Ted Waitt

Gary has invested in more than 50 venture-backed companies and served on more than 20 boards. Learn more at nassaustreetpartners.com or connect with Gary on LinkedIn.

About the Show:
The M&A Mastermind Podcast provides actionable insights and effective strategies tailored for dealmakers in the lower middle market. Hosted by Nick Olsen, the show features conversations with leading industry experts who share valuable knowledge on topics such as industry intelligence, deal management, collaborative successes, and specialized expertise. Listeners who support small to medium-sized business owners will find practical tactics and advice they can immediately apply to advance their mastery in mergers and acquisitions.

If you enjoyed this episode, please subscribe, rate, and leave a review. It helps more lower middle market dealmakers find the show.

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