35 Years in American Investment Banking with John Hill, Managing Partner at Hyde Park Capital

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 Axial | Website