
The M&A Mastermind Podcast features thought leaders who specialize in the lower middle market space and share their experiences and expertise across key areas of execution, such as: market analysis, lead generation, deal management, strategic partnerships, buyer access and much more.
With host Nick Olsen, each episode’s ”mastermind” will share ways in which they have found success in navigating the M&A industry to best support the small-to-medium sized private business owners they focus on serving.
The M&A Mastermind Podcast is your go-to source for the latest industry trends and strategies to level up your M&A practice.
The show features thought leaders who specialize in the lower middle market space and share their experiences and expertise across key areas of execution, such as: market analysis, lead generation, deal management, strategic partnerships, buyer access and much more.
With host Nick Olsen, each episode’s ”mastermind” will share ways in which they have found success in navigating the M&A industry to best support the small-to-medium sized private business owners they focus on serving.
Gary Shields has worked through the 1987 crash, the dot-com bubble, and now the AI boom. Host Nick Olsen talks with Gary, chairman and managing partner of Nassau Street Partners, about his career in investment banking, venture capital, and entrepreneurship. They also cover what past market cycles reveal about the “AI tsunami,” and why revenue and earnings still matter in the AI era.
Key Topics:
Gary Shields’ career, from Crédit Lyonnais to venture capital
Lessons from the 1987 crash and the dot-com bubble
How the semiconductor shaped the tech markets
The rise of AI and how it compares to past booms
How to build sustainable companies that generate revenue
Why real earnings matter in the AI era
How markets and investors behave during tech booms
The future of investment banking and venture capital with AI
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.
Subscribe and never miss an episode: Apple Podcasts | Spotify | YouTube
Resources: Nassau Street Partners | Gary Shields on LinkedInlinkedin | Cornerstone International Alliance
Keywords: investment banking, venture capital, entrepreneurship, market cycles, AI boom, tech investing, mergers and acquisitions, startup growth, market trends, business strategy, AI in M&A, dot-com bubble, Robertson Stephens, capital raising
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More on this week’s episode
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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.





