Beyond the Deal: Leadership Decisions that Shaped the Journey

Matthew Gurwin is a First Vice President, Private Wealth Advisor, and Certified Exit Planning Advisor (CEPA®) for Graystone Consulting at Morgan Stanley. He specializes in advising wealthy business owners and families, especially those considering substantial liquidity events due to the sale or recapitalization of a privately held business. A veteran of the financial services industry, Matt draws on his 25 years of experience, helping entrepreneurs and private business owners maximize the value of their business, take their personal and personal financial plans to the next level, and be prepared for what adventure comes next after transitioning their current company. He draws on his 20 years of experience in the field to collaborate with professionals in a range of industries, build relationships with existing and prospective clients, and enhance internal operations to improve our clients' experience.

Matt earned both his BBA and his MBA from the University of Michigan Ross School of Business. Prior to joining Graystone Consulting - Chicago, Matt was a Principal at Doeren Mayhew leading their firm’s business development efforts. Earlier in his career, Matt worked at Telemus Capital Partners, LLC, as a managing director and as an Investment Banker for Deloitte Corporate Finance.

Outside the office, Matt enjoys spending quality time with his spouse and their four children.

Shawn Bercuson is Founder & CEO of EarlyAsset and Managing Director of EarlyAsset Capital, focusing on venture secondaries. Previously, he was a founding member and VP of Business Development at Groupon and a Principal at Lightbank, with earlier experience in alternative asset management and fixed income trading. He brings more than two decades of experience across investing, operating, and entrepreneurship.

Billy leads the Nelson Mullins Private Equity Practice Group, where he counsels companies and their owners, private equity funds, and venture capital funds in a wide array of, buy-side and sell-side M&A transactions, equity financings, and complex corporate matters.

Mark Holland is CEO and Co-Founder of Choose Your Horizon, an Austin-based telehealth platform that is focused on advancing addiction medicine and changing how Americans get treated for alcohol use disorder. The company provides affordable care, discreetly from the comfort of patients' own homes, and is in network with major insurers. The team has delivered more than 30,000 clinically guided treatments across all 50 states, pairing medication-assisted treatment protocols including naltrexone and GLP-1s with counseling, at-home liver testing, and digital therapeutics. It ranked No. 102 on the 2026 Inc. 500, the second company Holland has built onto the list. Previously, as CEO of North America for Lifes2good, he grew the business from $200,000 to $50 million in revenue and led the commercial side of its $165 million exit to a Fortune 500 acquirer. He is deeply passionate about integrative, root-cause psychiatry.

Brenda Jacobsen is an experienced M&A advisor and former operator with a proven track record of running, growing, and selling companies, including family owned businesses. Over more than 25 years as a CEO and advisor, she has led transactions across industries such as healthcare, digital healthcare, industrial manufacturing, events, and specialty consumer markets, with deal experience exceeding $500M, including the sale of a family owned business in the automotive luxury and supercar industry. Her dual background as both CEO and advisor helps business owners exceed market valuations through the right strategic buyer and deal structure.

Experienced Principal, President & COO for a national cold chain brokerage, built from negative equity to category leadership, exited inside the business in 2025.