The M&A Mastermind Podcast

Hosted by Nick Olsen

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Episodes

100

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Jun 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

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

April 30, 2026Episode 13236 min

Mastering the Buy Side – Episode 132

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 being a proactive hunter. Challenges in sourcing motivated sellers on the buy side and how to overcome them. The significance of industry knowledge and market research for buy-side success. Building a network of potential buyers through strategic relationship cultivation, particularly with private equity firms. How buy-side activity can inform and strengthen sell-side opportunities through market insights. Tips for solo advisors considering enter buy-side work, including the importance of commitment and team support. Tips for identifying the right buy-side clients, assessing motivations, and ensuring alignment. Examples of client types — private equity, family-owned, public companies — and factors influencing engagement strategies. Advice on industry focus and evaluating market fragmentation for strategic buy-side searching. About the Show: The M&A Mastermind Podcast is dedicated to providing 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: Bama Website Cornerstone International Alliance LinkedIn Profile of Bobby Lewis Keywords: Private Equity, M&A, Deal Flow, Buy Side, Investment Banking, Market Trends, Exit Strategies, Middle Market, Mergers & Acquisitions, sell side, M&A Advisor

April 23, 2026Episode 13140 min

How Macroeconomics & Private Equity Deal Activity – Episode 131

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 activity Tools for faster M&A research and buyer identification The role of AI in streamlining deal processes and valuations Market trends and pipeline bulges in private equity Building trust and relationships in M&A transactions About the Show: The M&A Mastermind Podcast is dedicated to providing 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: Private Equity Info - https://privateequityinfo.com TruSight - https://trusight.com Guest links: LinkedIn - https://linkedin.com/in/andyjones Keywords: Private Equity, M&A, Deal Flow, Macroeconomics, AI in Finance, Private Equity Data, Investment Banking Tools, Market Trends, Exit Strategies, Middle Market, Mergers & Acquisitions

April 16, 2026Episode 13040 min

Is Cold E-mail Marketing Still Relevant? – Episode 130

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 marketing in a stricter inbox environment Key mistakes firms make when doing outreach independently How AI tools can enhance outreach, automation, and analysis Best timing and channels for outreach success Building a comprehensive deal sourcing ecosystem Strategies for integrating social proof via LinkedIn and websites Recommendations for leveraging AI without losing human touch About the Show: The M&A Mastermind Podcast is dedicated to providing 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: Exxelerate Group Connect with Manoo Wali: LinkedIn Twitter Email: manoo@exxelerategroup.com Keywords: Mergers & acquisitions, investment banking, email marketing, lead generation, business sales, sell side, buy side, valuation, deal-making, M&A,

April 9, 2026Episode 12936 min

Owner-Led Scaling & The Importance of Total Enterprise Value – Episode 129

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 enterprise value How business owners can identify and decrease dependency to boost company value The role of enterprise value as the primary health metric of a business Strategies for preparing a company for sale, including value acceleration practices before engagement with investment bankers The proprietary Propel software: features and advantages for tracking enterprise value and operations Building a team of expert advisors with the right DNA to support diverse business needs The importance of early value development, even if owners aren't immediately considering an exit About the Show: The M&A Mastermind Podcast is dedicated to providing 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: Propel Your Business Software — Proprietary enterprise value tracking tool Cultivate Advisors — Casey Clark’s firm for value acceleration and owner-led scaling Connect with Casey Clark: LinkedIn Twitter Keywords: Entrepreneurship, Business Scaling, Enterprise Value, Owner Led Growth, Business Exit, Cultivate Advisors, M&A, Business Coaching, Business Sale, Investment Banking, Mergers & Acquisitions