Branching Out: TreeFork Strategies

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. 

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.

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.

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.

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.

Elizabeth Shea sits down with Wayne Schepens, founder of LaunchTech Communications, to share the story of building a cybersecurity PR firm with the goal to sell. Wayne discusses how he created an agile business and honed a disciplined approach to growth, focusing on recurring revenue, strong margins, a client-centric approach, and a niche market strategy. He walks through how he prepared for an exit over several years, from working with an M&A advisor to building a unique team structure that reduced founder dependency. Wayne also offers candid insight into the sale process, choosing the right buyer, and the realities of post-acquisition integration. This episode is for founders who want to understand what it truly means to build a company designed for exit.

Elizabeth Shea sits down with Sean Griffey, co-founder and former CEO of Industry Dive, to discuss his journey of building a bootstrapped media company and navigating two successful exits. Sean shares how he and his co-founders left stable careers to launch niche industry publications at a time when investors were chasing "the next Buzzfeed” and why their contrarian strategy paid off. He reflects on the differences between partnering with private equity and running a competitive sale process to a strategic buyer. He also touches on the importance of financial transparency and the role of strategic communications in appealing to prospective buyers. This episode is for founders looking to maximize their enterprise value and find a buyer who aligns with their culture and long-term vision.

Elizabeth Shea sits down with John Burns, founder and managing director at Clare Advisors, a boutique M&A advisory firm specializing in marketing and advertising services agencies. John explains the advisor’s role throughout a sell-side process and shares how the marketing services landscape is evolving as AI capabilities are incorporated into the landscape and the buyer pool is becoming more diverse. He continually emphasizes that culture alignment can be the most valuable driver of true enterprise value that affects whether sellers can maximize their earn outs and retain their teams post-close. John also offers concrete ways to assess buyer fit, such as requesting references from CEOs of previously acquired companies, and reminds founders of the importance of selling when it feels “right” from a personal, financial, and operational perspective instead of jumping the gun as soon as a buyer reaches out.

In this episode of Branching Out, Elizabeth Shea is joined by Karl Sigerist, author of Selling Your Canadian Business, a book written for founders contemplating the sale of their privately owned, lower middle market Canadian business. Drawing on decades of experience as an operator, buyer, seller, and advisor, Karl offers nuanced insight into why most deals fail, how lack of early planning can leave value on the table, and why founders must answer the question “why do I want to sell?” long before going to market and use this “why” to anchor the entire process. His practical advice on prudent advisor selection, emotional readiness, maintaining clean books, and recognizing the value of your brand applies to founders everywhere contemplating or navigating a transition into the next chapter. 

Ab Emam shares how WDG evolved from a single website project for a friend into a full-scale, midmarket agency he deliberately built for sale. He breaks down why founders should plan years before they initiate a transaction, why hiring the right business banker can dramatically change your multiple, and why leadership teams need to keep their eye on the ball long after receiving the letter of intent. Ab also speaks candidly about the identity shift that founders can experience after closing and the importance of putting a strong operator in place. This episode is a practical, founder-to-founder look at selling with intention and keeping your head in the game until the ink is dry.

In this episode of Branching Out, Elizabeth Shea sits down with Jim Datovech, former CEO of LKC Technologies, to explore the long road from acquiring a medical device company to refining the product and orchestrating a successful exit. Jim shares how a deal that died at the last minute unexpectedly validated the company’s scalability and paved the way for a stronger deal months later. He offers candid insights on disciplined spending, legal preparedness, the importance of marketing to suitors, and why founders must align their expectations with market reality. This episode is a must-listen for leaders looking for practical advice to navigate a highly regulated industry.

In this episode of Branching Out, Elizabeth Shea sits down with Andrew Sherman, senior partner at Brown Rudnick, for a candid look at how deals really get priced, structured, and won. Andrew explains why M&A is cyclical, the differences between strategic and financial buyers, why sellers must perform reverse due diligence on buyers, and how to surface the “gold bars in the attic” — the intangible value drivers that buyers won’t pay for unless you point them out. He also unpacks common gotchas like PPP/EIDL distortions, rollover equity, earnouts, and under-capitalized “buyers” who look legit until it’s time to close. The bottom line: don’t just prepare your business — prepare your story, your expectations, and your deal team.

In this episode of Branching Out, Elizabeth sits down with Bess Winston, the founder of The Winston agency. She talks about how one modest media relations project-turned-campaign laid the foundation for her to meticulously build a nationally respected boutique firm with a powerhouse team before ultimately selling her agency in 2022. Bess shares her journey with the humor and unfiltered honesty only an experienced founder can bring. She sheds light on the emotional jolt of parting with a company, the importance of protecting your people, navigating post-acquisition culture shifts, the advice she wishes she hadn’t ignored, and the moment she learned the hard truth: “When you sign your name, you’re done.” This episode is for anyone weighing a major inflection point — whether you’re debating when to slow down, when to scale up, or who really deserves a seat at your deal table.

In this episode of Branching Out, Allan Klassen, former CEO and managing partner of Albi Homes, shares how he helped turn a Calgary-based luxury home builder into a “niche of one” and a strategic acquisition target which was acquired by Brookfield Residential in 2015. Allan walks through the realities of negotiating with a globally recognized asset management company, keeping a deal alive when it nearly collapsed, and the lessons he learned about non-negotiables, timing, and values alignment. He also opens up about the deeply emotional transition from entrepreneurial leader to an executive inside a finance-driven organization, and how that journey led him to a new role as Chief Experience Officer and ultimately to launching his own advisory practice, Clarity Quest. This conversation is a must-listen for founders and leaders who want to prepare not just their business — but themselves — for a future transaction.

In this episode of Branching Out, Ethan McAfee shares how he built Amify from a one-man operation in his Arlington townhouse into one of the largest Amazon agencies in the country, helping major consumer brands with their strategy content, advertising, and supply chain before selling to Cart.com in 2024.  Drawing on his earlier career as an internet stock investment analyst, Ethan explains how venture capital, market cycles, and founder energy can all factor into the timing and structure of an exit. He offers practical advice on preparing your company years ahead of a sale, reducing founder dependence, and balancing growth against burn to maintain control over your options. Now a senior advisor at a private equity fund, Ethan reflects on what it’s like to move from operator to investor-mentor — and why closing one chapter can be the best way to open the next.

In this episode of Branching Out, Susan Apgood, the former CEO of News Generation, shares candid insights about her journey selling her company in April 2020 in the midst of the COVID lockdown. She opens up about navigating a challenging broker relationship, unexpected cultural clashes between merging teams after the acquisition, and the emotional reality of watching a company you built change in ways you didn’t foresee. Susan also reflects on why due diligence, communication, and support networks—especially for women founders—are essential during an exit. Now a full-time professor at American University, she brings those lessons forward to empower the next generation of women business leaders.

In this episode of Branching Out, Jake Bittner, former CEO of Qlarion, recounts his path from co-founding a government data analytics firm to leading it through a successful acquisition by GCOM in 2021. He offers a transparent look at what it’s like to navigate the sale process with private equity buyers, from managing due diligence to balancing emotion with strategy. Jake also reflects on how selling a business changes your perspective on leadership, purpose, and personal identity. His story reveals the often-overlooked realities of exiting a company—and finding clarity on what comes next. 

In this episode of Branching Out, Cary Hatch, former CEO of MDB Communications, opens up about the deals she walked away from, the one that finally felt right, and what it takes to step away from the CEO seat after decades at the helm. She shares how timing, values alignment, and a deep sense of purpose shaped her journey — and offers honest insights into the realities of selling an agency after years of leadership. Cary discusses the critical factors that influenced her decision, the importance of understanding market dynamics, and the challenges of transitioning to a new role post-sale. She also highlights the need for introspection and the emotional aspects of letting go. Her story is a powerful reminder that success in an exit isn’t just about valuation—it’s about vision, integrity, and fulfillment beyond the deal.

In the inaugural episode of Branching Out, Elizabeth Shea interviews Viraj Gandhi– former CEO and founder of Paradyme Inc. – about his 21-year journey from building a local and state contracting business to leading a major federal contractor acquired in 2024. Viraj shares how an unexpected AI partnership propelled the company toward acquisition and reflects on the complexities of cultural fit, emotional readiness, and life after selling a business. Their conversation offers candid insights for founders preparing to navigate both the practical and deeply personal sides of an exit.