Buying from First-Time Sellers: How to Navigate Inexperience and Close with Confidence
Presented By: Bowditch & Dewey / KLR CPAs & Business Advisors
For most entrepreneurs, selling a company is a once-in-a-lifetime experience—while for buyers, it can become routine. That imbalance can create friction, delays, emotional decision-making, and unrealistic expectations. This session brings together experienced acquirers, private equity leaders, and deal advisors to share real-world examples of common pitfalls, communication breakdowns, and negotiation challenges, along with practical strategies for building trust, maintaining momentum, and protecting value while guiding inexperienced sellers through a complex process.
Moderator:
Partner, CGO + Director of Private Equity and Transaction Services
KLR CPAs & Business Advisors
John Surrette is a Partner, CGO + Director of Private Equity and Transaction Services at KLR. He works with PE firms with back office and portfolio company needs. He assists clients in evaluating investment opportunities as well as providing hands on experience during the pre and post transaction process, including providing buy-side and sell-side due diligence/quality of earnings services.
Panelists:
Partner
Bowditch & Dewey
Peter Cifichiello is a dynamic business lawyer at Bowditch, specializing in corporate transactions. He advises clients on mergers and acquisitions, equity and convertible note financings for startup and emerging growth companies, corporate structuring and outside general counsel matters including governance. Peter is also well versed in commercial transactions that involve vendor and consumer services, licensing, shareholder rights, and executive employment. His clients are comprised of small and mid-cap companies, professional service providers, investment entities and financial institutions.
Working closely with clients, Peter manages deals from beginning to end. Many clients also call upon him to provide outside general counsel services both before and after transactions. Peter’s deep understanding of a client’s businesses, respective risk tolerance and the legal issues most relevant to them is invaluable. His hands-on approach enables him to help companies seamlessly adapt to rapidly changing markets. Peter applies an execution-oriented approach to the practice of law that facilitates the efficient management of the clients’ growth, corporate structures, intellectual property, and financial discipline.
The CEO to CEOs
Symphony Advantage Inc.
Kent Gregoire has successfully exited 15 of his own companies and raised over $250 million in capital across his career as a serial entrepreneur. As Co-Founder and CEO of Symphony Advantage, he advises purpose-driven CEOs on building businesses positioned for successful exits, working alongside M&A teams on behalf of his clients. Kent is a Certified Conscious Capitalism Consultant.
President & Co-Owner
Tread Labs
Nathan Isaacson is President & Co-Owner of Tread Labs, a Boston-based insoles and footwear brand. He and his partner, Joe Rusckowski, acquired Tread Labs in 2025. Previously, Nathan spent over 10 years at New Balance, where he held multiple senior leadership roles both in the US and internationally. Nathan is a graduate of Bowdoin College and the Tuck School at Dartmouth, and is married with three daughters.