The M&A Mastermind Podcast
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

Thursday Feb 13, 2025
Thursday Feb 13, 2025
In this episode of the M&A Mastermind podcast, Joe Strazzeri discusses advanced planning strategies for business owners, focusing on the importance of timing, combining, and sequencing various strategies to achieve financial goals. He outlines the eight key goals that business owners should consider, including maintaining control, ensuring lifestyle, and protecting against taxes and lawsuits.
Joe emphasizes the need for integrated planning and the importance of working with knowledgeable professionals to navigate complex financial landscapes. He also shares insights on common and lesser-known strategies, as well as educational resources available for advisors.
Tune in now and elevate your understanding of M&A dynamics with the podcast that delivers actionable insights and unlocks the door to new possibilities. To learn more about M&A trends and insights, please like, subscribe, and rate our podcast. New episodes go live every Thursday at 9 am CST.
Some Key takeaways include:
Timing, combining, and sequencing are crucial for effective planning.
Business owners often focus on numbers without considering net value.
Integrated planning can reduce taxes and increase asset protection.
Emotional and relational factors play a significant role in business transitions.
Cash flow is essential for supporting family and business needs.
Advisors should be aware of both common and niche strategies.
Education and continuous learning are vital for financial advisors.
Professional guidance is necessary to avoid costly mistakes.
Understanding client goals is key to effective planning.
The right strategies can help achieve multiple financial objectives.
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.
Chapters:
00:00 Introduction to Advanced Planning Strategies
08:43 The Eight Goals of Business Owners
17:32 Common and Lesser-Known Strategies for Advisors
Keywords: advanced planning, business strategies, tax planning, asset protection, financial goals, M&A, business owners, estate planning, wealth management, legal strategies

Thursday Feb 06, 2025
Thursday Feb 06, 2025
In this episode of the M&A Mastermind podcast, host Nick Olsen interviews Jim Urban, an expert in exit and succession planning. Jim shares his journey from wealth advisor to specializing in helping privately owned businesses, particularly family businesses, navigate the complexities of exit planning. He discusses the importance of aligning personal wealth with business value, the unique processes he employs, and the critical need for robust continuity plans.
The conversation also touches on the impending 'silver tsunami' of baby boomer business owners looking to exit, the significance of cultural fit in business sales, and the current market trends affecting exits. Jim emphasizes the importance of preparation and timing in exit planning, and he shares insights from his upcoming book, "Succession by Design."
Tune in now and elevate your understanding of M&A dynamics with the podcast that delivers actionable insights and unlocks the door to new possibilities. To learn more about M&A trends and insights, please like, subscribe, and rate our podcast. New episodes go live every Thursday at 9 am CST.
Some Key takeaways include:
Jim Urban started as a wealth advisor and shifted to exit planning.
The unique process begins with understanding the client's objectives.
Aligning personal wealth with business value is crucial for successful exits.
Robust continuity plans are essential to avoid liquidation events.
Timing is key; ideally, clients should start planning 2-15 years before an exit.
The 'silver tsunami' refers to the wave of baby boomers exiting their businesses.
Cultural fit is increasingly important in business sales.
Market conditions are favorable for exits, but preparation is necessary.
Legacy considerations often outweigh the desire for top dollar in sales.
Jim's upcoming book focuses on intentional succession planning.
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.
Chapters:
00:00 Introduction to Exit Planning and Succession
03:06 Understanding the Unique Process of Exit Planning
06:08 Maximizing and Protecting Business Value
09:01 The Importance of Timing in Exit Planning
12:00 The Silver Tsunami: Baby Boomers Exiting
14:54 Cultural Fit in Business Sales
17:54 Market Trends and Future Exits
21:05 Legacy vs. Top Dollar in Business Sales
23:55 The Role of M&A Advisors in Exit Planning
26:58 Jim's Upcoming Book and Its Insights
Keywords: exit planning, succession planning, business value, M&A, baby boomers, legacy, market trends, business sales, continuity planning, risk management

Thursday Jan 30, 2025
Thursday Jan 30, 2025
In this episode of the M&A Mastermind podcast, Nick Olsen interviews Colin Bowman, a partner and VP at Cultivate Advisors. They discuss the intricacies of growing a business, preparing it for sale, and the importance of increasing enterprise value.
Colin shares his journey from the franchise world to advising small businesses, emphasizing the need for a solid business plan and the role of M&A advisors in the selling process. The conversation highlights the collaborative nature of business advisory services and the significance of emotional readiness for business owners considering a sale.
Tune in now and elevate your understanding of M&A dynamics with the podcast that delivers actionable insights and unlocks the door to new possibilities. To learn more about M&A trends and insights, please like, subscribe, and rate our podcast. New episodes go live every Thursday at 9 am CST.
Some Key takeaways include:
Colin's journey from franchise ownership to business advising.
The impact of COVID-19 on small businesses and entrepreneurship.
Cultivate Advisors focuses on increasing enterprise value for clients.
70% of clients want to scale, while 30% are preparing to exit.
Key metrics for increasing enterprise value include financial health and operational efficiency.
Successful case studies demonstrate the effectiveness of their advisory model.
The importance of collaboration between business advisors and M&A professionals.
Emotional readiness is crucial for business owners looking to sell.
Tax strategies play a significant role in post-sale financial planning.
Cultivate Advisors offers complimentary advising to M&A professionals.
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.
Chapters:
00:00 Introduction to Cultivate Advisors and Colin Bowman
01:10 Colin's Journey and the Impact of COVID-19
02:48 Understanding Cultivate Advisors' Business Model
03:41 Client Profiles and Business Lifecycle Stages
05:22 Increasing Enterprise Value: Key Metrics and Strategies
07:40 Success Stories: Case Studies of Growth
10:41 The Team Sport of Business Advisory
13:25 Preparing for Sale: The Role of M&A Advisors
19:32 The Importance of Emotional Readiness in Selling
21:46 Tax Strategies and Financial Planning for Business Owners
25:31 Collaboration with M&A Advisors for Successful Exits
Keywords: business growth, enterprise value, M&A, advisory services, small business, exit strategy, financial planning, entrepreneurship, case studies, business lifecycle

Thursday Jan 23, 2025
Thursday Jan 23, 2025
In this episode of the M&A Mastermind podcast, host Nick Olsen interviews Greg Maloney, CEO of Strategic M&A Advisors, discussing the critical role of insurance and risk management in mergers and acquisitions. They explore how sellers can prepare for buyer due diligence, the importance of professional advisors, and real-life case studies that highlight the impact of risk management on M&A transactions.
The conversation emphasizes the need for sellers to understand the due diligence process and the value of surrounding themselves with knowledgeable advisors to enhance their business's valuation and readiness for sale.
Tune in now and elevate your understanding of M&A dynamics with the podcast that delivers actionable insights and unlocks the door to new possibilities. To learn more about M&A trends and insights, please like, subscribe, and rate our podcast. New episodes go live every Thursday at 9 am CST.
Some Key takeaways include:
Buyer's insurance and risk management are crucial in M&A.
Sellers often lack preparation for buyer due diligence.
Understanding risk factors can enhance business valuation.
Professional advisors play a key role in M&A success.
Real-life incidents can derail M&A transactions.
Effective risk management can lower insurance costs.
Sellers should engage with their insurance firms early.
Due diligence is an extensive and critical process.
Business owners should leverage available resources.
A proactive approach to risk management is essential.
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.
Chapters:
00:00 Introduction to M&A and Risk Management
03:10 Understanding Insurance and Risk Management in M&A
06:00 The Role of Due Diligence in M&A Transactions
09:05 Real-Life Impacts of Risk Management on M&A
11:55 Preparing Sellers for Buyer Due Diligence
14:52 The Importance of Professional Advisors
17:46 Case Studies: Lessons Learned from M&A Transactions
21:07 Final Thoughts on Risk Management and M&A
Keywords: M&A, risk management, insurance, due diligence, buyer's insurance, seller preparation, strategic advisors, case studies, business valuation, insurance policies

Thursday Jan 16, 2025
Thursday Jan 16, 2025
In this episode of the M&A Mastermind Podcast, host Nick Olsen interviews Joe Strazzeri, a tax attorney and expert in advanced tax planning for business owners. Joe shares his background, the importance of tax planning, and the four motives that drive business owners. He emphasizes the need for early conversations about tax planning, the timing of strategies, and shares real-life success stories of clients who benefited from proper planning. The discussion also covers the role of M&A advisors, and the various brands and programs Joe offers to help advisors and business owners navigate the complexities of tax planning and business transitions.
Tune in now and elevate your understanding of M&A dynamics with the podcast that delivers actionable insights and unlocks the door to new possibilities. To learn more about M&A trends and insights, please like, subscribe, and rate our podcast. New episodes go live every Thursday at 9 am CST.
Some Key takeaways include:
Tax planning is crucial for business owners, especially during exit.
Understanding the four motives of business ownership is essential.
Early conversations about tax planning can prevent costly surprises.
The timing of tax planning strategies can significantly impact outcomes.
Real-life examples illustrate the benefits of advanced tax planning.
M&A advisors play a vital role in maximizing business value.
Advanced planning requires a comprehensive approach and collaboration.
Education and resources are available for advisors to enhance their skills.
Proper planning can lead to significant financial benefits for clients.
It's important to keep the client's best interests at heart.
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.
Chapters:
00:00 Introduction to Advanced Tax Planning
05:33 The Importance of Early Tax Planning
12:43 Common Scenarios in Tax Planning
21:44 The Role of M&A Advisors
27:25 Overview of Joe's Brands and Programs
Keywords: tax planning, business owners, M&A, asset protection, wealth management, estate planning, financial advisors, advanced strategies, exit planning, family business

Thursday Jan 09, 2025
Thursday Jan 09, 2025
In this episode of the M&A Mastermind podcast, host Nick Olsen and guest Jim Cumbee discuss the critical role of referral networks in business development. They explore how referrals are often taken for granted, the importance of building relationships and credibility, and the use of content as a tool for connection. Jim shares personal anecdotes that highlight the serendipitous nature of referrals and emphasizes the need for professionalism and trust in these relationships.
In this conversation, Jim Cumbee and Nick Olsen explore the intricacies of building and managing referral networks in professional services. They discuss the importance of trust and quality content in fostering relationships with referral sources, particularly wealth advisors, and how these relationships can lead to successful business transactions. Jim emphasizes the need for professionals to provide value to their referral sources and to maintain open communication throughout the process. The discussion also touches on the challenges of managing a large referral network and the significance of creating meaningful connections rather than transactional relationships.
Tune in now and elevate your understanding of M&A dynamics with the podcast that delivers actionable insights and unlocks the door to new possibilities. To learn more about M&A trends and insights, please like, subscribe, and rate our podcast. New episodes go live every Thursday at 9 am CST.
Some Key takeaways include:
Referrals are often taken for granted in business.
Building a referral network requires active nurturing and relationship building.
Professionalism and capability are essential for gaining referrals.
Content marketing can help reinforce credibility and keep you top of mind.
Casual conversations can lead to significant business opportunities.
Trust is more important than transactional relationships in referrals.
Referral sources need to feel confident in your abilities.
Being helpful and thoughtful can lead to more referrals.
It's important to communicate your value without overtly promoting yourself.
The nature of referrals is often serendipitous and unpredictable. I want the client to hire me if they're fully convinced.
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.
Chapters:
00:00 The Importance of Referral Networks
08:39 Building Relationships and Credibility
17:05 Content as a Tool for Connection
24:44 Trust and Professionalism in Referrals
30:24 Identifying Key Referral Sources
36:44 Building and Managing Referral Networks
44:53 Creating Value Through Quality Content
Keywords: referral networks, business development, credibility, professional relationships, M&A, solopreneurs, networking, content marketing, trust, entrepreneurship, referral fees, professional services, wealth advisors, business transactions, referral networks, quality content, relationship building, trust, networking strategies, business growth

Thursday Jan 02, 2025
Thursday Jan 02, 2025
We’re wrapping up 2024 with Part 2 of our year’s best moments from the M&A Mastermind Podcast! This follow-up episode dives even deeper into the insights, strategies, and success stories that defined the year.
Join us as we spotlight more of the most impactful conversations with industry leaders, dealmakers, and transition experts. In this episode, you’ll discover:
How to hire the right advisor the first time
"Focusing on what you do best and hiring experts" - Episode 50 - YouTube
Insights into the technology space in Germany
"Timing is the key thing in the technology sector regarding M&A." - Episode 49
A deep dive into the software industry and philanthropy
It isn't just about numbers and valuations; it’s about people - Episode 64
The human side of M&A
"Cash at close, equity rollover, and the dreaded earn out." - Episode 48
Whether you’re planning your next move or staying sharp in the M&A arena, this episode is packed with actionable takeaways to help you win big in 2024 and beyond.
Don’t miss Part 2 of this ultimate recap! Subscribe now to stay connected with the strategies shaping the M&A landscape.

Thursday Dec 26, 2024
Thursday Dec 26, 2024
In this special year-in-review episode of the M&A Mastermind Podcast, we’re bringing you the most powerful, insightful, and game-changing moments from the past year. Whether you’re a seasoned dealmaker, a business owner contemplating a sale, or a professional navigating the M&A landscape, this episode distills the key strategies, expert advice, and actionable takeaways from our top conversations.
Listen in as we revisit standout clips covering:
Proven strategies for maximizing business value
"Investing in Employees for Long-Term Success" - Episode 46
Expert insights on cross boarder deals
"Cross-border M&A is all about trust and chemistry" - Episode 22
Tips for all things buy-side
"The Buy Side Advantage" - Episode 33
All you need to know about Good Will
"Maximizing Goodwill Value" - Episode 27
This "greatest hits" episode is your chance to absorb the year’s best M&A wisdom in one powerful conversation.
Don’t forget to subscribe for more expert content and stay ahead in the world of M&A.

Thursday Dec 19, 2024
Thursday Dec 19, 2024
In this episode of the M&A Mastermind podcast, host Nick Olsen interviews Greg Brinson, CEO of CapLinked, a virtual data room platform. They discuss the evolution and importance of virtual data rooms in M&A transactions, highlighting key features, security measures, and the support provided to clients.
Greg emphasizes the need for a sophisticated data room to protect sensitive information and streamline the transaction process, while also hinting at future developments including AI integration.
Tune in now and elevate your understanding of M&A dynamics with the podcast that delivers actionable insights and unlocks the door to new possibilities. To learn more about M&A trends and insights, please like, subscribe, and rate our podcast. New episodes go live every Thursday at 9 am CST.
Some Key takeaways include:
Greg Brinson shares his journey into corporate sales and the importance of virtual data rooms.
CapLinked aims to simplify transactions and protect data with an easy-to-use platform.
The evolution of data rooms from physical to virtual has made transactions more efficient.
Key features of CapLinked include activity tracking, Q&A functionality, and document security.
Security is paramount in M&A transactions, especially when sharing sensitive information.
CapLinked provides extensive support and training for clients to ensure ease of use.
The platform allows for customizable branding, enhancing professionalism in transactions.
Due diligence can be managed effectively through CapLinked's features, reducing confusion.
Future developments may include AI functionalities to enhance reporting and monitoring.
Using a virtual data room is a professional necessity in today's sophisticated M&A landscape.
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.
Chapters:
00:00 Introduction to Corporate Sales and Cooking
01:53 Understanding Virtual Data Rooms
04:52 Evolution of Data Rooms and Their Importance
10:01 Key Features of CapLinked's Data Room
14:50 Security and Access Control in M&A Transactions
19:52 Support and Training for Clients
24:48 Future Developments and Conclusion
Keywords: M&A, virtual data rooms, CapLinked, corporate sales, data security, transaction management, investment banking, due diligence, AI in data rooms, client support

Thursday Dec 12, 2024
Thursday Dec 12, 2024
In this episode of the M&A Mastermind Podcast, host Nick Olsen interviews Shaunna Balady, a member of Cornerstone International Alliance, who specializes in the software industry. Shaunna shares her extensive experience in M&A, emphasizing the importance of operational expertise, philanthropy, and emotional intelligence in transactions. She discusses the evolving landscape of software M&A, the significance of relationships in client acquisition, and the future trends in the industry.
Shaunna also highlights the critical role of people in software companies and the need for retention strategies during transitions. The conversation concludes with insights on how to navigate the complexities of M&A in the software sector.
Tune in now and elevate your understanding of M&A dynamics with the podcast that delivers actionable insights and unlocks the door to new possibilities. To learn more about M&A trends and insights, please like, subscribe, and rate our podcast. New episodes go live every Thursday at 9 am CST.
Some Key takeaways include:
Philanthropy is a core value that drives their business model.
Operational experience is crucial for preparing companies for sale.
Building relationships is key to client acquisition in M&A.
Emotional intelligence plays a significant role in M&A transactions.
Understanding buyer dynamics is essential for successful deals.
The software industry is experiencing rapid digitization and growth.
Retention of key employees is critical during transitions.
Education on software-specific vocabulary is necessary for M&A professionals.
The future of software M&A looks promising with continued opportunities.
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.
Chapters:
00:00 Introduction to Shaunna Balady and Cornerstone International Alliance
06:03 Philanthropy and Knowledge Sharing in M&A
11:53 Building Relationships and Client Acquisition
17:52 Understanding Buyer Dynamics in Software M&A
23:50 Key Takeaways for M&A Professionals
Keywords: M&A, software industry, Shaunna Balady, Cornerstone International Alliance, operational experience, philanthropy, buyer dynamics, future trends, emotional intelligence, client acquisition