The M&A Mastermind Podcast

By Nick OlsenBusiness Entrepreneurship Management

The M&A Mastermind Podcast episodes

May 30The 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)
40 min
May 21How 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
33 min
May 14Achieving 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
37 min
May 07An 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
26 min
April 30Mastering 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
37 min
April 23How 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
41 min
April 16Is 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: [email protected]
Keywords:
Mergers & acquisitions, investment banking, email marketing, lead generation, business sales, sell side, buy side, valuation, deal-making, M&A,
41 min
April 09Owner-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
37 min
April 02Collaboration Amongst Business Coaches & M&A Advisors – Episode 128
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 identify if your business is ready for sale and what gaps to address
The importance of third-party valuations in strategic planning
Role of experienced coaches with real-world business exit experience
Synergies between Scaling Up and strategic partnership frameworks for maximizing business value
Future trends in business transfer of wealth and how to prepare for upcoming market opportunities
Resources & Links:
Scaling Up
Jason Wells on LinkedIn
Scaling Up Coaches on LinkedIn
This episode underscores the importance of a strategic, disciplined approach to scaling and preparing your business for sale, emphasizing early planning, valuation, and the value of experienced coaches to bridge gaps and accelerate growth. Tune in every week for more insights on building, scaling, and selling your business effectively.
Keywords:
Mergers & Acquisitions, M&A, scaling up, business coaches, business sale, strategy, valuations, growth, exit
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/
38 min
March 26The Importance of Connection & Collaboration in M&A – Episode 127
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 International Alliance’s annual conference.
In this episode:
The importance of collaborative peer groups in the M&A industry
How conferences foster real-time learning, validation, and deal sharing
Practical applications of AI in deal analysis and communications
The impact of social activities in building trust and stronger relationships
Insights from private equity panels and deal strategy sessions
The value of sharing deal insights and real-world experiences
How to create a culture of continuous improvement and learning
Effective strategies to stay top of mind with potential clients and partners
Resources & Links:
ICCG - Integrated Corporate Consulting Group
Cornerstone International Alliance
Connect with Grant MacQuilkan:
ICCG - LinkedIn
ICCG - Website
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/
Keywords:
Mergers & acquisitions, M&A, investment banking, business sales, collaboration, Cornerstone International Alliance, private equity, family office, sell side, buy side, valuation, due diligence, AI, differentiation
50 min

About The M&A Mastermind Podcast

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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…