Masters in Small Business M&A

Today's guests are Alex de Pfyffer and Ross Porter, Co-Founders of Heritage Holding, an investment firm that has completed nearly 50 acquisitions across 12 active platform companies.

After graduating from HBS, where they met as classmates and intramural soccer teammates, Alex and Ross partnered up to pursue a self-funded search. They share what gave them the confidence to move forward on their first acquisition, a business many PE investors passed on due to customer concentration and key-person risk.

Alex and Ross explain how an unexpected second acquisition emerged that set them on the path from self-funded search to an independent sponsor and, eventually, to raising a $220M committed fund focused on acquiring and scaling sub-$10M EBITDA businesses. 

The conversation also covers sourcing, founder partnerships, building acquisition platforms, and advice for the next generation of HBS searchers.

Discussion Points:

Masters in Small Business M&A is produced by its host Peter Lehrman and the team at Axial (www.axial.com). Axial makes it easy for small business owners to confidentially explore growth capital and exit transactions with top-ranked lower middle market M&A advisors and professional capital partners. In every episode, we explore the dynamic world of small business M&A, interviewing a mix of proven and emerging owners, operators, acquirers, and M&A advisors whose strategies and methods are being put to the test.

If you’d like to go deeper, head to Axial.com, where we make available the Axial member directories, downloadable tools for dealmakers, the Axial quarterly lower middle market investment banking league-table rankings, the SMB M&A pipeline report, and other useful information. If you’re a business owner, professional acquirer, or M&A advisor, you can start using Axial for free at Axial.com.

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Today’s guest is Grant Hensel, founder of Entrepreneurial Capital, a fund that partners with self-funded searchers acquiring small businesses through ETA. After building and exiting businesses of his own, making personal ETA investments, and completing an acquisition with his wife, Grant launched Entrepreneurial Capital to back the next generation of owner-operators.

In this episode, Grant explains why he prefers the self-funded search model over traditional search funds, how he evaluates both businesses and searchers, and the investment philosophy behind backing a "trustworthy searcher buying an enduring business." The conversation also covers the evolution of the ETA ecosystem, lessons from underwriting dozens of acquisitions, and the growing role of SBA lending and policy in financing small business acquisitions.

Discussion Points:

Masters in Small Business M&A is produced by its host Peter Lehrman and the team at Axial (www.axial.com). Axial makes it easy for small business owners to confidentially explore growth capital and exit transactions with top-ranked lower middle market M&A advisors and professional capital partners. In every episode, we explore the dynamic world of small business M&A, interviewing a mix of proven and emerging owners, operators, acquirers, and M&A advisors whose strategies and methods are being put to the test.

If you’d like to go deeper, head to Axial.com, where we make available the Axial member directories, downloadable tools for dealmakers, the Axial quarterly lower middle market investment banking league-table rankings, the SMB M&A pipeline report, and other useful information. If you’re a business owner, professional acquirer, or M&A advisor, you can start using Axial for free at Axial.com.

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Today's guest is Lane Carrick, founder of Optima Mergers & Acquisitions, a boutique lower middle market investment bank he launched in 2024. Lane brings a “renaissance man” profile and personal story to the M&A advisory seat: he grew up in the Holiday Inn franchise business his father built, completed a leveraged buyout in his 20s without knowing it, founded and exited a wealth management firm, cofounded B.B. King's Blues Club, and now teaches M&A and alternative investments at SMU as an adjunct professor.  He’s also a published author.  

Lane and Peter discuss the founder's exit journey through a business sale. Drawing on his experience as both an entrepreneur and advisor, Lane explains why some owners begin thinking about an exit only after a triggering event, why he often feels like an emergency room physician for founders, and how emotions are usually what put deals at risk. 

The conversation also covers private equity's complicated reputation among business owners, the importance of buyer chemistry, how sellers begin to second-guess a transaction as it approaches the finish line, and what to do about it.

Discussion Points:

Masters in Small Business M&A is produced by its host Peter Lehrman and the team at Axial (www.axial.com). Axial makes it easy for small business owners to confidentially explore growth capital and exit transactions with top-ranked lower middle market M&A advisors and professional capital partners. In every episode, we explore the dynamic world of small business M&A, interviewing a mix of proven and emerging owners, operators, acquirers, and M&A advisors whose strategies and methods are being put to the test.

If you’d like to go deeper, head to Axial.com, where we make available the Axial member directories, downloadable tools for dealmakers, the Axial quarterly lower middle market investment banking league-table rankings, the SMB M&A pipeline report, and other useful information. If you’re a business owner, professional acquirer, or M&A advisor, you can start using Axial for free at Axial.com.

Resources

Matt Plooster returns to the podcast to deliver a timely update on private credit and specifically its deployment in the lower middle market. 

Despite lingering gaps in awareness and education among business owners and professional advisors, the overall picture is bullish on private credit’s continued growth and deployment. The bearish private credit headlines in the WSJ and Bloomberg aren’t representative of lower middle market activity. AI and private credit in software have undergone a full re-rating. Software no longer gets its own software-centric ARR oriented underwriting framework.  It’s back to cash flow and EBITDA.  

Matt and Peter examine how non-dilutive capital is being used to solve shareholder liquidity issues, fund growth, and support acquisition strategies for Main Street businesses. They also cover the current bifurcation in the private credit market, why software underwriting has shifted materially in the AI era, and why industrial and infrastructure-related sectors continue attracting significant private credit dollars. 

The conversation closes with a broader discussion that is closer to home for Matt regarding AI’s impact on the investment banking industry, the deal process, and how it’s impacting investment banking hiring and diligence processes. Again, listeners will hear some surprising answers that fly in the face of the mainstream media’s generally gloomy AI narrative.   

Discussion Points:

Masters in Small Business M&A (sign up for podcast drops here) is produced by its host Peter Lehrman and the team at Axial (www.axial.com). Axial makes it easy for small business owners to confidentially explore growth capital and exit transactions with top-ranked lower middle market M&A advisors and professional capital partners. In every episode, we explore the dynamic world of small business M&A, interviewing a mix of proven and emerging owners, operators, acquirers, and M&A advisors whose strategies and methods are being put to the test.

If you’d like to go deeper, head to Axial.com, where we make available the Axial member directories, downloadable tools for dealmakers, the Axial quarterly lower middle market investment banking league-table rankings, the SMB M&A pipeline report, and other useful information. If you’re a business owner, professional acquirer, or M&A advisor, you can start using Axial for free at Axial.com.

Resources

Today’s guest is James Bohannon of Belzberg & Co., a family office with a significant history of backing lower middle market independent sponsors and leading direct investments.

James joins Peter to discuss the emerging “F2E” (Finance to Entrepreneurship) category, where pedigreed investment professionals are leaving “partner-track” roles in private equity or investment banking to acquire and operate lower middle market businesses.

James shares how this category differs from traditional ETA or independent sponsor models, why more top-caliber finance professionals are pursuing this path, and how family offices evaluate and partner with these emergent operator investors. The discussion also covers James’ perspective on capital formation, the role of anchor investors, and the key characteristics he sees in the most promising “F2Es”.

Discussion Points:

Masters in Small Business M&A is produced by its host Peter Lehrman and the team at Axial (www.axial.com). Axial makes it easy for small business owners to confidentially explore growth capital and exit transactions with top-ranked lower middle market M&A advisors and professional acquirers. In every episode, we explore the dynamic world of small business M&A, interviewing a mix of proven and emerging owners, operators, acquirers, and M&A advisors whose strategies and methods are being put to the test.

If you’d like to go deeper, head to Axial.com, where we make available the Axial member directories, downloadable tools for dealmakers, the Axial quarterly lower middle market investment banking league-table rankings, our Industry Top 50 reports, the SMB M&A pipeline report, and other useful information. If you’re a business owner, professional acquirer, or M&A advisor, you learn more and get started for free at Axial.com.

Resources

Today’s guest is Eliot Kerlin, Founder and Managing Partner of Broadwing Capital. With 25 years of experience in the lower middle market, Eliot reflects on how the ecosystem has evolved—from fund sizes and leverage trends to seller sophistication and the rise of independent sponsors and family offices. He shares how underwriting, equity contributions, and operational involvement have changed, and why operational alignment from the start is a prerequisite to growth. The conversation closes with Broadwing’s investment philosophy, its approach to founder alignment post-transaction, and a look into their recent acquisition of CloudScale 365.

Discussion Points:

Masters in Small Business M&A is produced by its host Peter Lehrman and the team at Axial (www.axial.com). Axial makes it easy for small business owners to confidentially explore growth capital and exit transactions with top-ranked lower middle market M&A advisors and professional capital partners. In every episode, we explore the dynamic world of small business M&A, interviewing a mix of proven and emerging owners, operators, acquirers, and M&A advisors whose strategies and methods are being put to the test.

If you’d like to go deeper, head to Axial.com, where we make available the Axial member directories, downloadable tools for dealmakers, the Axial quarterly lower middle market investment banking league-table rankings, the SMB M&A pipeline report, and other useful information. If you’re a business owner, professional acquirer, or M&A advisor, you can start using Axial for free at Axial.com.

Today’s guests are Thomas Ince and Logan Lowery, Managing Partners of LP First Capital, a top-rated independent sponsor that has closed 70 deals in just six years. Ince and Lowery share the origin of the firm’s name and dive into how LP First approaches investor alignment, capital structuring, and platform building. They discuss the nuances of working with a diverse mix of LPs, co-GP partnerships with private equity firms, and the firm’s emphasis on speed, sourcing discipline, and founder alignment. The conversation closes with reflections on hold vs. exit decisions, the firm's evolution, and what lies ahead.

Discussion Points:

Masters in Small Business M&A (sign up for podcast drops here) is produced by its host, Peter Lehrman, and the team at Axial (www.axial.com). Axial makes it easy for small business owners to confidentially explore growth capital and exit transactions with top-ranked lower middle market M&A advisors and professional capital partners. In every episode, we explore the dynamic world of small business M&A, interviewing a mix of proven and emerging owners, operators, acquirers, and M&A advisors whose strategies and methods are being put to the test.

If you’d like to go deeper, head to Axial.com, where we make available the Axial member directories, downloadable tools for dealmakers, the Axial quarterly lower middle market investment banking league table rankings, the SMB M&A pipeline report, and other useful information. If you’re a business owner, professional acquirer, or M&A advisor, you can start using Axial for free at Axial.com.

Resources

Today’s guest is Bo Stump, a partner at Stump & Company, a family-owned third-generation M&A advisory firm based in Charlotte, North Carolina. 

The folks at Stump & Company are among the most trusted and respected thinkers and advisors on exit strategy and M&A across the entire furniture supply chain, from wholesale materials and manufacturing, all the way to branded goods and their evolving distribution channels. 

In this episode, Peter and Bo discuss how the furniture industry’s supply chain has evolved — from domestic manufacturing to global sourcing and now e-commerce — and how these shifts impact profit pools, relative valuations, and buyer appetite. 

The conversation also reveals how Stump & Company thinks about sell-side exit process dynamics, how they do the calculus on what kind of process to run, what kinds of buyers to invite, and how they handle the often competing interests of certainty of close, speed to close, and optimal price and terms.

Discussion Points:

Masters in Small Business M&A (sign up for podcast drops here) is produced by its host Peter Lehrman and the team at Axial (www.axial.com). Axial makes it easy for small business owners to confidentially explore growth capital and exit transactions with top-ranked lower middle market M&A advisors and professional capital partners. In every episode, we delve into the dynamic world of small business M&A, interviewing a diverse mix of seasoned and emerging owners, operators, acquirers, and M&A advisors whose strategies and methods are being put to the test.

If you’d like to go deeper, head to Axial.com, where we make available the Axial member directories, downloadable tools for dealmakers, the Axial quarterly lower middle market investment banking league table rankings, the SMB M&A pipeline report, and other useful information. If you’re a business owner, professional acquirer, or M&A advisor, you can start using Axial for free at Axial.com.

Resources:

Today’s guest is Nick Huber, founder and owner of Bolt Storage and current CEO of Somewhere.com, a worldwide staffing business acquired in 2024. 

Nick joins Peter to discuss the formative acquisitions across his entrepreneurial journey – from growing a distressed storage portfolio into 60+ properties, to the $52M acquisition of worldwide remote staffing firm, Somewhere.com. They cover his transition from operator to acquirer and back to CEO, capital structuring tactics, and why he bet so big on Somewhere.com. 

On top of it all, Nick found time to publish his book, The Sweaty Startup, and offers key insights from the book and why he wrote it.

Discussion Points:

Masters in Small Business M&A (sign up for podcast drops here) is produced by its host, Peter Lehrman, and the team at Axial (www.axial.com). 

Axial helps qualified business owners confidentially explore growth capital and exit transactions with top-ranked M&A advisors and professional capital partners in the lower middle market. The podcast seeks to explore the dynamic world of small business M&A, interviewing a mix of proven and emerging owners, operators, acquirers, and M&A advisors whose strategies and methods are being put to the test.

If you’d like to go deeper, head to Axial.com, where we make available the Axial member directories, downloadable tools for dealmakers, the Axial quarterly lower middle market investment banking league-table rankings, the SMB M&A pipeline report, and other useful information. If you’re a business owner, professional acquirer, or M&A advisor, you can start using Axial for free at Axial.com.

Resources:

On today’s episode, Kyle Tucker, founder of Tucker’s Farm Corporation, joins Peter Lehrman to share his journey from big league private equity and hedge fund land to creating a unique investment platform focused on roll-ups in the lower middle market. 

Kyle shares how early inspiration from Warren Buffett and experiences in private equity shaped his approach to long-duration, high-compounding investments. They discuss Tucker’s Farm's focus on aggregation strategies, the importance of friction in deal sourcing and in deal execution, and why Kyle prioritizes operational scale over traditional private equity paths.

Discussion Points:

Masters in Small Business M&A (sign up for podcast drops here) is produced by its host Peter Lehrman and the team at Axial (www.axial.com). Axial makes it easy for qualified business owners to confidentially explore growth capital and exit transactions with the lower middle market’s top-ranked lower middle market M&A advisors and professional capital partners. In every episode, we explore the dynamic world of small business M&A, interviewing a mix of proven and emerging owners, operators, acquirers, and M&A advisors whose strategies and methods are being put to the test.

If you’d like to go deeper, head to Axial.com, where we make available the Axial member directories, downloadable tools for dealmakers, the Axial quarterly lower middle market investment banking league-table rankings, the SMB M&A pipeline report, and other useful information. If you’re a business owner, professional acquirer, or M&A advisor, you can start using Axial for free at Axial.com.