Put Your Chin Strap On: Interview with David Tobin

Put Your Chin Strap On: Interview with David Tobin

Elizabeth Shea chats with David Tobin, Managing Partner of TobinLeff LLC, about how founders can best prepare themselves and their businesses for a successful exit. Drawing on his experience as both a former agency owner and longtime M&A advisor, David explains what buyers are prioritizing in today’s market, including sustainable growth, strong margins, leadership continuity, recurring revenue, and reduced founder dependency. The discussion dives into the realities of adjusted EBITDA, client concentration risk, due diligence, and how AI readiness is increasingly becoming part of buyer evaluations. David also breaks down the differences between strategic and private equity buyers, including platform acquisitions, rollover equity, and earnout structures, while emphasizing why deal terms often matter just as much as valuation. Throughout the episode, he offers practical insight into creating competitive buyer dynamics, choosing the right advisor, and navigating the intensity of the M&A process.

Quarterbacking the Deal: Interview with Salman Husain

Elizabeth Shea sits down with Salman Husain, co-founder and managing director of Monument Capital Partners, to discuss the evolving M&A landscape for founder-owned government services companies. Salman shares his journey from government consulting into investment banking and explains how his experiences in this sector have shaped his perspective on mission-driven businesses and the founders behind them. He offers insight into what buyers are really looking for in today’s market, including strong leadership teams, scalable growth pipelines, and reduced owner dependency. Salman also discusses why preparation matters years before a sale, the importance of surrounding yourself with experienced advisors, and how deal terms can impact outcomes just as much as valuation.

Find Your Platters: Interview with Sue Keith

Elizabeth Shea sits down with Sue Keith, co-founder of Ceres Talent, to share her story of building a specialized recruiting firm and navigating an unexpected path to exit. Sue discusses her unconventional career journey, how she and her partner grew the business organically by reaching key inflection points, and how a chance meeting at a conference led to a successful acquisition by Landrum HR. She offers candid insights into the realities of the deal process: from timelines and negotiations to identifying non-negotiables and protecting employees. Sue also reflects on life after the sale and the importance of cultural fit and shared values in choosing the right partner.

Alpha the Deal: Interview with Chris Mechanic

Elizabeth Shea sits down with Chris Mechanic, co-founder and former CEO of Web Mechanics, to share the story of building and exiting a successful digital agency. Chris reflects on his entrepreneurial beginnings, from an early online venture to launching Web Mechanics and growing it organically over 15 years. He discusses how an unexpected opportunity led to the sale of the business and offers candid insight into negotiating deal terms, navigating due diligence, and transitioning post-acquisition. Chris also shares lessons learned about founder identity, recognizing his personal strengths, and why he ultimately returned to the founder role launching a new AI-driven venture. This episode is for founders thinking about the full lifecycle from startup to exit and beyond.

Better Together: Interview with Houston Goodwin

Elizabeth Shea talks with Houston Goodwin, CEO of Better Impact, about a different approach to growth: entrepreneurship through acquisition. Houston shares how he stepped into Better Impact through a private equity partnership and led the strategic acquisition of Galaxy Digital to expand the company’s impact in the volunteer management space. He walks through the realities of the acquisition process from diligence to integration, emphasizing the value of operational readiness, cultural alignment, and clear communication. Houston also discusses how the two companies built a “better together” strategy rooted in shared mission and values. This episode is for operators and founders exploring acquisition as a path to growth and what it takes to execute it successfully.