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The M&A Mastermind Podcast

The M&A Mastermind Podcast

Nick Olsen 100 episodes Latest May 29, 2026

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.

Episodes

Elevating Risk Management for Business Growth – Episode 138 Jun 11, 2026 1591 Discover how strategic insurance planning and proactive risk management can drive business value, secure operations, and enhance exit opportunities. Led by Brian Riemer, CEO of Riemer Insurance Group, this episode delves into transforming insurance from a transactional expense into a strategic tool for businesses. Main Topics: The evolution of insurance from transactional to strategic advisory Ho
Unlocking AI Potential – Episode 137 Jun 4, 2026 2295 Explore how AI can transform leadership, strategy, and efficiency in business with Ivey Conefry, a trusted advisor with experience in the military and aerospace industries. Learn practical prompting techniques, the importance of CRIT methodology, and how to integrate AI into daily workflows for a competitive advantage. Key  Topics: Prompting best practices CRIT methodology (Context, Role, Intervi
The Hidden Challenges After a Business Exit – Episode 136 May 30, 2026 2394 In this episode, Jerome Myers, founder of Exit Excellence, dives deep into the often-overlooked psychological and emotional impacts of business exits. He emphasizes the importance of preparing business owners not just financially, but for a fulfilling post-exit life, tackling themes like identity loss, purpose, and mental health. Key Topics The "Founder’s Exit Paradox" — why the hardest part begi
How Structure Unlocks Hidden Business Value – Episode 135 May 21, 2026 1970 Unlock the secrets to sustainable business growth, overcoming stall zones, and preparing for exit strategies with real-world insights from Chris Burke. Whether you're scaling up or planning to sell, learn what structures create real value, how owner dependency impacts valuation, and practical steps to elevate your business. Main Topics Covered: The importance of system and structure over ideas fo
Achieving Outrageous Prices in M&A Deals – Episode 134 May 14, 2026 2200 Kevin Short, CEO of Clayton Capital Partners, shares his expertise on how to engineer better M&A outcomes by proactively preparing companies and understanding buyer psychology. Learn about the outrageous price process, the importance of competitive advantages, and how to call buyers' bluff to maximize deal value. Key Topics Outrageous price process and its four pillars How to identify and lev
An Acquisition in the Dealmaking Tech Space – Episode 133 May 7, 2026 1521 Nevin Raj, co-founder of Grata, discusses the transformative role of AI in M&A, recent acquisitions, and practical AI strategies for private market professionals. Insights include platform integrations, market intelligence, and the future of AI-driven workflows.  Nevin also dives into the partnership with Datasite and his viewpoint as the seller. Key Topics AI's impact on M&A workflows Pl
Mastering the Buy Side – Episode 132 Apr 30, 2026 2196 Explore the nuances of building a successful buy-side practice in M&A with Bobby Lewis, a seasoned expert with over 16 years of experience. Discover how to develop your market expertise, identify motivated sellers, and leverage buy-side activities to benefit your overall M&A strategy. In this episode: Key differences between sell-side and buy-side practices, emphasizing the importance of
How Macroeconomics & Private Equity Deal Activity – Episode 131 Apr 23, 2026 2404 In this episode, Andy Jones, founder of Private Equity Info, shares insights on macroeconomic trends shaping private equity deal activity, the importance of data quality, and how AI can revolutionize M&A processes. Discover practical tools and strategies to accelerate deal flow and build trust in the industry. Main Topics: Impact of interest rates on private equity exit and acquisition activi
Is Cold E-mail Marketing Still Relevant? – Episode 130 Apr 16, 2026 2428 In this episode, Nick Olsen chats with Manoo Wali about the current state and future of cold email outreach in deal-making, exploring how AI and changing inbox behaviors are reshaping B2B marketing strategies. They share actionable insights on crafting effective outreach, leveraging automation, and maintaining credibility in a noisy digital world. Main Topics: The evolution of cold email marketin
Owner-Led Scaling & The Importance of Total Enterprise Value – Episode 129 Apr 9, 2026 2174 In this episode, Casey Clark shares the story behind founding Cultivate Advisors, a venture that helps business owners accelerate value and transition toward owner-led scaling. Gain practical advice on reducing dependency, preparing for sale, and leveraging enterprise value for long-term success. Key Topics Covered: The concept of owner-led scaling and its importance in building transferable ente
Collaboration Amongst Business Coaches & M&A Advisors – Episode 128 Apr 2, 2026 2274 Looking to accelerate your business growth or prepare for a successful exit? In this episode, Jason Wells, CEO of Scaling Up Coaches, shares insights on the four key disciplines of scaling—strategy, people, execution, and cash—and how they can be leveraged to significantly increase business valuation. In This Episode: Overview of the Scaling Up methodology and its four core disciplines How to ide
The Importance of Connection & Collaboration in M&A – Episode 127 Mar 26, 2026 2959 Discover how industry leaders like Grant MacQuilkan leverage peer collaboration, practical AI applications, and strategic networking to elevate their firms' performance. This episode dives into the value of peer groups, real-world deal insights, and continuous learning to stay ahead in the competitive M&A landscape.  Hear directly from Grant on his recent experience at Cornerstone Internationa

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