Masters in Small Business M&A

Today’s guest is John Hill, Managing Partner of Hyde Park Capital, a boutique investment bank he co-founded in 2000. Hyde Park focuses on raising capital and selling American lower middle market businesses with $5M to $50M in EBITDA. The firm has specialized bankers within the Healthcare, Technology, Industrials, Business & Financial Services, Consumer, and most recently, Digital Infrastructure verticals.   John and Peter discuss what has changed and what has remained the same over more than three decades of lower middle market investment banking. John unpacks how and why private equity has become a dominant exit option for smaller businesses, the extinction of the sub-$100M IPO, why M&A transactions take longer today than decades ago, and how AI will reshape deal execution.  They also cover the growing specialization of investment banks, the challenges of building and managing an advisory firm, and the complexities of evaluating an increasingly diverse universe of buyers. Discussion Points: John's early career at Morgan Stanley and building Raymond James' technology division Founding Hyde Park Capital in 2000, just before the dot-com bubble burst Navigating the early 2000s downturn and diversifying Hyde Park Capital's industry focus The challenges of managing an investment bank built around transaction-based revenue Culture, client relationships, and the importance of emotional intelligence The rise of private equity as an alternative to smaller public offerings Why M&A transactions take longer to close despite advances in technology The growing role of due diligence and quality of earnings reports How AI could improve efficiency across the M&A process The evolving skill sets of junior and senior investment bankers The shift toward greater industry specialization among M&A advisors Balancing specialized expertise with broader buyer relationships Evaluating buyer credibility, financing capabilities, and certainty of closing 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 John Hill | LinkedIn Hyde Park Capital | Website Peter Lehrman | LinkedIn...

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: Why they chose a self-funded search over a traditional search fund Ross's path from Stanford engineering and a hearing-aid startup into search Alex's investment banking background and what drew him to small business acquisitions Underwriting customer concentration risk: how they structured their first acquisition Why earning founder trust starts long before the LOI The shift from mass email campaigns to a relationship-driven sourcing strategy Building acquisition platforms through industry-focused buy-and-build strategies Why their earliest investors continued backing each new platform The decision to raise a $220 million committed fund in 2024  Staying disciplined on deal size: why they target businesses averaging $2 million of EBITDA Why "scaling quickly" appears on Heritage Holding's homepage, and where they deliberately move slowly Returning to HBS to share their deal story and share advice for future searchers Why the firm is named "Heritage Holding," not "Heritage Holdings" 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 Alex de Pfyffer LinkedIn Ross Porter LinkedIn Heritage Holding Website

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: Why Grant is drawn to self-funded search over the traditional search fund model Entrepreneurial Capital’s thesis: a trustworthy searcher buying an enduring business Raising a $12.8 million debut fund backed by 80 LPs Key underwriting risks: customer concentration, economic resilience, and capital efficiency Evaluating searcher trustworthiness using the Speed of Trust framework Why the self-funded search community is a surprisingly small, interconnected world Sourcing talent versus sourcing deals, and the This Week in ETA newsletter Managing a deal with multiple interested searchers and involving the seller in the selection SBA loan basics and its role in financing ETA acquisitions Recent tightening of SBA underwriting standards and citizenship eligibility The SBA E-Tran issue impacting repeat investors in small business acquisitions How Grant thinks about portfolio construction, defaults, and downside risk Distinguishing operational challenges from seller fraud Potential effects of raising the SBA 7(a) loan cap Perspectives on personal guarantees and required equity injections Why Grant favors conservative leverage in SBA-backed acquisitions Outlook on future fund size and the evolving ETA equity capital landscape 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 adviso...

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: Lane Carrick’s entrepreneurial upbringing and early business influences Lessons learned from his father’s successful Holiday Inn exit Building and exiting his own wealth management business Why owners often decide to sell only after a triggering life event The difference between planned exits and emergency-room transactions Challenges of unsolicited acquisition offers from private equity firms The risks of negotiating with a single buyer versus running a competitive process Communication breakdowns between founders and institutional buyers The importance of specialized M&A legal counsel Setting valuation expectations before going to market Recognizing self-sabotaging behavior during the sale process Common misconceptions about private equity buyers Evaluating execution risk across private equity, search funds, and strategic buyers The importance of chemistry, trust, and cultural fit between buyers and sellers Building buyer relationships versus focusing on founder relationships How his new book helps owners assess sellability, optimization, and exit readiness Planning for identity and purpose after the sale of a business 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 ran...

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: The continued education gap around private credit in the lower middle market How private credit helps solve shareholder liquidity and succession issues Why today’s LMM credit environment is more borrower-friendly than headlines suggest The role of non-dilutive capital in growth and acquisition financing How software underwriting standards have shifted in the AI era The growing importance of defensible EBITDA and cash flow generation Why industrials, infrastructure, and data center-related sectors remain attractive Strategic buyers versus private equity buyers in today’s M&A market The impact of AI on investment banking workflows and diligence How AI is reshaping analyst hiring and talent evaluation The future of white-collar work and AI adoption inside professional services firms Why clean financial data is becoming even more important in transactions How younger professionals are approaching careers with greater intentionality and purpose 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 inv...

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: The emergence of the “F2E” (Finance to Entrepreneur) investor in small business acquisitions How “F2E” differs from ETA, search funds, and traditional independent sponsors Why mid-career finance professionals are leaving partner-track roles to buy businesses The risks and personal stakes F2E operators bring when investing their own capital How capital formation works between F2Es and family offices The role of anchor family offices in supporting these new sponsors How reputation and relationships drive deal flow and partnerships in the ecosystem Gaps in skill sets when transitioning from large PE firms to smaller, scrappier deals Why fundraising and sales become core responsibilities for first-time sponsors How family offices source and evaluate emerging sponsors The importance of alignment and trust between investors and F2E sponsors Why the individual operator (“the jockey”) often matters more than the specific deal The potential for F2E to become a meaningful pipeline of talent into the lower middle market over the next decade 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 James Bohannon LinkedIn Peter Lehrman LinkedIn

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: Fund size expansion and the shifting definition of “middle market” Rising purchase multiples, increasing equity contributions, and their implications  The growth of “operational private equity” and specialization How sell-side advisory channels have expanded and digitized The rise of independent sponsors and new buyer pathways Family offices as capital partners in private equity Broadwing’s investment strategy and focus on skilled trades, manufacturing, and services Organic growth versus acquisition-led growth Evaluating management teams and cultural fit Stakeholder impact planning and employee investment initiatives Founder alignment and setting post-transaction expectations The acquisition thesis behind CloudScale 365 AI as both an operational tool and a client advisory opportunity Balancing playbooks with the uniqueness of each company 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: The story behind the name “LP First” and its layered meaning Structuring investor alignment through incentive design Evolving LP mix and the importance of thoughtful capital composition Why LP First often starts transactions all-equity and leverages up later Getting comfortable with private equity funds as LPs Co-GP partnerships with private equity firms and how LP First approaches governance Criteria for selecting GP partners and building trust LP First’s value prop: speed, responsiveness, and sourcing systems Building and executing within a focused buy box Prioritizing founder energy and cultural fit in platform investments Thoughts on hold duration, liquidity timing, and compounding value Scaling thoughtfully while building long-term firm credibility 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 Thomas Ince’s LinkedIn Logan Lowery’s LinkedIn Peter Lehrman’s LinkedIn Thomas Ince’s X Peter Lehrman’s X LP First Capital Website Axial’s 2025 Independent Sponsor Report

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: History and evolution of Stump & Company The firm’s niche focus in the furniture and home goods sectors Shifts in manufacturing: domestic, offshore, and hybrid models Rise of e-commerce and omnichannel distribution The growing influence of interior designers on furniture purchasing Attributes that drive premium valuations in furniture businesses How Bo’s team runs different types of M&A processes A case study on optimizing buyer fit over the highest bid Private equity’s cycles of engagement in the furniture space Bo’s take on how to prepare for an exit and “timing” the market 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

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: Nick’s first storage buildout in 2015 and the pivot to acquisitions A turning point deal: buying a mismanaged Erie, PA portfolio at public auction Transitioning from scrappy operations to managing a global team Building out a PE-backed acquisition engine for Bolt Storage Underwriting and managing 62 storage acquisitions with global remote staff Why Nick slowed down storage deals after the 2022 interest rate spike The story behind acquiring Somewhere.com for $52M Breaking down the deal structure and equity incentives Rebuilding operations post-acquisition: new hires, new brand, new funnel Why South Africa became central to Somewhere.com  Transforming sales and recruiting teams using global talent Which industries are adopting global hiring (law, construction, SaaS, architecture) Why AI is not replacing Somewhere.com’s business model anytime soon Lessons from raising outside capital and the pressure that comes with it The overlap between operating and authoring The Sweaty Startup Masters in Small Business M&A (sign up for podcast drops here) is produced by its host, Peter Lehrman, and the team at Axial (