The M&A Mastermind Podcast

Hosted by Nick Olsen

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Episodes

100

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Jul 2026

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About the show

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.

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60 recent

July 9, 2026Episode 14238 min

Risks That Can Sabotage Business Transfers - Episode 142

In this episode, Laurie Barkman, a seasoned exit strategist and author, shares insights on business transition, exit planning, and building transferable value. She discusses common pitfalls, the importance of succession planning, and how business owners can prepare for a successful exit. Key Topics Business transition and exit planning Common pitfalls in business transfer Building transferable business value Succession planning and owner dependency Employee bench and leadership development Timing and communication during exit Choosing the right buyer and exit options Internal vs external transfer of business Tools and resources for exit planning 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. Tune in Every Week: Subscribe: https://www.youtube.com/@UCl0qSCwwZLyZxY7RnqNghiw Apple: https://podcasts.apple.com/us/podcast/the-m-a-mastermind-podcast/id1726394585 Spotify: https://open.spotify.com/show/4fpVjEXbJ0FXKMgEK0m7QQ Find all our episodes at https://cornerstoneia.com/podcast/ Resources The Business Transition Handbook - https://lauriebarkman.me/book Succession Stories Podcast - https://podcasts.apple.com/us/podcast/succession-stories/id123456789 Business Transition Sherpa - https://btsherpa.com Laurie Barkman - LinkedIn - https://www.linkedin.com/in/lauriebarkman/ Keywords: Exit planning, business transition, succession, value creation, ownership transfer, business sale, exit strategy, business growth, leadership, entrepreneurship, mergers & acquisitions, M&A, sell side, buy side, valuation

July 2, 2026Episode 14139 min

Hidden Costs of Not Having a Succession Plan – Episode 141

This episode features Renee Russo discussing exit planning, succession strategies, and the importance of early preparation for business owners. She emphasizes the need for a comprehensive team approach, addressing emotional and structural challenges, and leveraging AI for future success. Key Topics: Exit planning importance Succession conversation barriers Business valuation and transferability Team and advisory collaboration Future of exit planning 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. Tune in Every Week: Subscribe: https://www.youtube.com/@UCl0qSCwwZLyZxY7RnqNghiw Apple: https://podcasts.apple.com/us/podcast/the-m-a-mastermind-podcast/id1726394585 Spotify: https://open.spotify.com/show/4fpVjEXbJ0FXKMgEK0m7QQ Find all our episodes at https://cornerstoneia.com/podcast/ Resources: Exit Planning Institute - https://exitplanninginstitute.com ReadyToRiseBook.com - https://ReadyToRiseBook.com DriveValue.com - https://drivevalue.com Connect: LinkedIn - https://linkedin.com/in/reneerusso Keywords: Mergers & acquisitions (M&A), exit planning, succession, business owner, valuation, advisory, AI, business transition, preparation, team, wealth management, sell side, buy side, valuation

June 25, 2026Episode 14035 min

Succession by Design – Episode 140

Jim Erben, a veteran succession and exit planning advisor, discusses the importance of strategic planning for business owners to ensure successful exits, minimize taxes, and secure their legacy. He emphasizes the need for intentionality, comprehensive valuation, and building a strong team to navigate the upcoming trillion-dollar business transition. Key Topics: The upcoming $13 trillion business transition The importance of strategic succession planning Building a dream team for exit readiness 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. Tune in Every Week: Subscribe: https://www.youtube.com/@UCl0qSCwwZLyZxY7RnqNghiw Apple: https://podcasts.apple.com/us/podcast/the-m-a-mastermind-podcast/id1726394585 Spotify: https://open.spotify.com/show/4fpVjEXbJ0FXKMgEK0m7QQ Find all our episodes at https://cornerstoneia.com/podcast/ Resources: Success by Design book launch details Erben Associates Cornerstone International Alliance Keywords: Succession planning, exit strategy, business valuation, legacy, business exit, planning, wealth management, M&A, business owner, succession by design

June 18, 2026Episode 13933 min

Digital Resilience Explained – Episode 139

Understanding cybersecurity risks is crucial for M&A transactions, especially in the lower middle market where these risks often go unchecked. This episode features Philippe Flichy, founder of Cykur, who shares his expertise on integrating cybersecurity into the valuation process and safeguarding enterprise value. Main Topics: The concept of business resilience and its importance in cybersecurity planning Common cybersecurity vulnerabilities overlooked in M&A due diligence Six pillars of cybersecurity assessment: governance, architecture, data protection, security operations, compliance, and legal How digital and cyber risks differ, and why digital risks are now tangible The impact of cyber breaches on company valuation, including real-world examples Due diligence practices: policies, procedures, and assessing third-party risks The role of AI in cybersecurity risks and best practices for protection Cyber insurance or cyber risk coverage: what to look for and questions to ask Post-transaction cyber integration strategies and the importance of incident response planning Key Highlights: Business resilience involves pre-attack preparations (like backups and incident response plans) and post-attack recovery strategies. Large breaches (e.g., Marriott's 500 million records breach) highlight the importance of cybersecurity for all company sizes. Cyber risks are increasingly tangible and can significantly impact enterprise value—up to 30% in some cases. Questions around policies, procedural revisions, and third-party risk assessments are critical for early cybersecurity evaluation. AI tools introduce new risks, such as unauthorized access and attacks, emphasizing the need for controlled and monitored usage. Effective cybersecurity due diligence can unlock an additional 30% of perceived value in M&A transactions. 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. Tune in Every Week: Subscribe: https://www.youtube.com/@UCl0qSCwwZLyZxY7RnqNghiw Apple: https://podcasts.apple.com/us/podcast/the-m-a-mastermind-podcast/id1726394585 Spotify: https://open.spotify.com/show/4fpVjEXbJ0FXKMgEK0m7QQ Find all our episodes at https://cornerstoneia.com/podcast/ Connect with Philippe Flichy: LinkedIn Twitter Keywords: Cybersecurity, M&A Due Diligence, Digital Resilience, Cyber Risks, Business Valuation, Cyber Insurance, AI Security, Data Protection, Incident Response, Cyber Threats, Mergers & Acquisitions, Sell Side, Buy Side, Valuations, Sell my Business

June 11, 2026Episode 13826 min

Elevating Risk Management for Business Growth – Episode 138

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 How private equity deal analysis informs better risk management practices The importance of continuous insurance reviews aligned with business growth Private equity insights: due diligence and insurance considerations during deal transactions Creating operational resilience through risk assessments, cybersecurity, and disaster planning Industry shifts: data analytics, specialization, and the impact of consolidation among insurance agencies Practical steps for business owners to prepare for sale or exit with optimal risk management 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. Tune in Every Week: Subscribe: https://www.youtube.com/@UCl0qSCwwZLyZxY7RnqNghiw Apple: https://podcasts.apple.com/us/podcast/the-m-a-mastermind-podcast/id1726394585 Spotify: https://open.spotify.com/show/4fpVjEXbJ0FXKMgEK0m7QQ Find all our episodes at https://cornerstoneia.com/podcast/ Connect with Brian Riemer: Riemer Insurance Group LinkedIn Keywords: Mergers & Acquisitions (M&A), insurance, investment banking, sell side, buy side, valuation, risk management

June 4, 2026Episode 13738 min

Unlocking AI Potential – Episode 137

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, Interview, Task) AI integration in workflows Overcoming AI adoption resistance Using AI for M&A and deal analysis 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. Tune in Every Week: Subscribe: https://www.youtube.com/@UCl0qSCwwZLyZxY7RnqNghiw Apple: https://podcasts.apple.com/us/podcast/the-m-a-mastermind-podcast/id1726394585 Spotify: https://open.spotify.com/show/4fpVjEXbJ0FXKMgEK0m7QQ Find all our episodes at https://cornerstoneia.com/podcast/ Resources: AI Leadership - https://aileadership.com/ LinkedIn - https://www.linkedin.com/in/ivey-mcclam-conefry/ Cornerstone International Alliance - https://cornerstoneia.com/ Keywords: AI leadership, prompting techniques, CRIT methodology, business efficiency, AI in M&A, AI strategies, Ivey Conefry, AI transformation, mergers & acquisitions, sell side, buy side, valuation, investment banking

May 30, 2026Episode 13639 min

The Hidden Challenges After a Business Exit – Episode 136

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 begins after the sale Common emotional pitfalls post-exit such as identity loss and purpose crisis How advisors can facilitate meaningful conversations about life after sale The significance of early planning for personal fulfillment and purpose Recognizing warning signs that a founder is not emotionally or physically ready to exit The impact of structuring deals, including earn-outs and transition periods, on post-exit well-being Jerome’s frameworks: Transaction Illusion and Exit to Fulfillment Strategies for advisors to hold space and support founders through emotional challenges The role of relationships, health, prosperity, and significance centers in post-exit satisfaction 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. Tune in Every Week: Subscribe: https://www.youtube.com/@UCl0qSCwwZLyZxY7RnqNghiw Apple: https://podcasts.apple.com/us/podcast/the-m-a-mastermind-podcast/id1726394585 Spotify: https://open.spotify.com/show/4fpVjEXbJ0FXKMgEK0m7QQ Find all our episodes at https://cornerstoneia.com/podcast/ Resources & Links Your Next: A Guide to Finding Fulfillment Post Exit – Jerome Myers’ podcast on life after exit Exit Readiness Assessment Tool – Jerome’s tool to evaluate client preparedness Book: Exit to the Next by Jerome Myers – For deeper understanding of exit planning Jerome Myers - LinkedIn | Twitter Keywords Exit Planning, Post-Exit Life, Founder’s Exit Paradox, Transaction Illusion, Emotional Readiness, Earn-Outs, Transition Periods, Exit Readiness Assessment, Six Centers of Doubt, Business Owner Support, Personal Fulfillment, Advisor Strategies, Life Beyond Business, Mergers & Acquisitions (M&A)

May 21, 2026Episode 13532 min

How Structure Unlocks Hidden Business Value – Episode 135

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 for business growth Identifying and overcoming the "stall zone" from 10 to 30 million dollars How founder dependency reduces business value and strategies to minimize owner reliance Practical steps to transition from operator to owner, including team building and system implementation Critical aspects of preparing a business for sale, including legal, financial, and cultural considerations Using acquisition as a growth strategy when organic growth slows Best practices for owner exit planning and negotiations 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. Tune in Every Week: Subscribe: https://www.youtube.com/@UCl0qSCwwZLyZxY7RnqNghiw Apple: https://podcasts.apple.com/us/podcast/the-m-a-mastermind-podcast/id1726394585 Spotify: https://open.spotify.com/show/4fpVjEXbJ0FXKMgEK0m7QQ Find all our episodes at https://cornerstoneia.com/podcast/ Resources & Links: theduvo.com Keywords: Mergers & acquisitions, M&A, sell side, buy side, valuation, exit planning, business exit, sell your business, deal structure, business owner, investment banking, due diligence

May 14, 2026Episode 13436 min

Achieving Outrageous Prices in M&A Deals – Episode 134

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 leverage competitive advantages Strategies for calling buyers' bluff and setting high price benchmarks The importance of research and understanding buyer psychology Case studies of successful high-multiple deals 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. Tune in Every Week: Subscribe: https://www.youtube.com/@UCl0qSCwwZLyZxY7RnqNghiw Apple: https://podcasts.apple.com/us/podcast/the-m-a-mastermind-podcast/id1726394585 Spotify: https://open.spotify.com/show/4fpVjEXbJ0FXKMgEK0m7QQ Find all our episodes at https://cornerstoneia.com/podcast/ Resources Sell Your Business for an Outrageous Price Clayton Capital Partners com Keywords M&A, business valuation, outrageous price, competitive advantage, deal strategy, buyer psychology, middle market, Kevin Short, Clayton Capital Partners, mergers, acquisitions, Cornerstone International Alliance, sell side, buy side

May 7, 2026Episode 13325 min

An Acquisition in the Dealmaking Tech Space – Episode 133

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 Platform integrations and acquisitions Market intelligence and deal activity insights Practical AI tools for private market professionals 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. Tune in Every Week: Subscribe: https://www.youtube.com/@UCl0qSCwwZLyZxY7RnqNghiw Apple: https://podcasts.apple.com/us/podcast/the-m-a-mastermind-podcast/id1726394585 Spotify: https://open.spotify.com/show/4fpVjEXbJ0FXKMgEK0m7QQ Find all our episodes at https://cornerstoneia.com/podcast/ Resources Grata Website - https://grata.com Datasite - https://www.datasite.com Blue Flame AI - https://blueflame.ai Cornerstone International Alliance - https://cornerstoneia.com/ Keywords AI, M&A, private markets, data platform, acquisitions, workflow automation, market intelligence, Grata, Datasite, Blue Flame AI, sell side, buy side, business sales, mergers & acquisitions