Matthew T. Streif, CEPA®
Managing Partner, Westport Wealth PartnersWealth Advisor, RJFS
Matthew T. Streif spent most of his life in Austin, TX and obtained both his Bachelors and MBA from the University of Texas at Austin. He spent the first 21 years of his Wealth Management career working as a Financial Advisor for Morgan Stanley and UBS and left both firms as a Senior Vice President.
He holds the Certified Exit Planning Advisor (CEPA®) designation from the Exit Planning Institute: a credential that goes well beyond general financial planning into the specific mechanics of what drives business valuation, exit structuring, and post-sale financial planning. He is a Managing Partner at Westport Wealth Partners, a three-partner wealth advisory practice in Westport, CT affiliated with Raymond James Financial Services.
What Most Business Owners Miss
Nearly thirty years later, that lesson still shapes how Matt works with business owners. He's seen it again and again: an owner decides it's "time to sell" because of a personal milestone (retirement, a health scare, a partner walking away) without realizing that the value and marketability of their business could have been meaningfully improved years earlier, simply by focusing on the right metrics in advance. By the time life says it's time, the business, or the market, often isn't ready.
Who Matt Works With
Matt works primarily with business owners who are somewhere in the years before a sale or transition: people who've been running their company for decades, who haven't had a reason to think about what it's worth, and who are starting to realize that the business is the retirement plan, and there's no plan yet for the transition.
He works well with Baby Boomers and young entrepreneurs alike, who are starting to think seriously about the next phase of their lives, and who need to understand how to convert a business they've spent years building into the personal income and financial confidence they want for the next chapter.
He's particularly well-suited for clients who want to understand their options, not just be told what to do. He describes his approach as collaborative: "I try to be a sounding board as much as an advisor. The best clients I work with are the ones who want to understand the thinking, not just the recommendation."
What Matt Focuses On
The central problem Matt helps business owners solve is one that many general financial advisors aren't well-positioned to address: after a business sale, two things stop, the cash flow, and the deductions. The business that has been functioning as both the income source and the primary tax shelter disappears, often simultaneously. Building a personal financial plan that replaces both requires planning that starts before the transaction, not after.
His work with clients covers the full scope of this challenge:
- helping owners understand what outside buyers actually focus on, and what changes can improve business value before a transaction is explored.
- evaluating the realistic buyer landscape for a specific business type, including strategic acquirers, private equity firms, employee stock ownership plans (ESOP), and family succession.
- building the personal financial plan that accounts for investment management, income replacement, tax coordination (with the client's CPA), estate planning, and risk management together, not in silos.
- for clients ready to explore a transaction, working alongside Raymond James investment bankers who specialize in middle-market business sales.
"I understand that there are both qualitative and quantitative dimensions to personal finance. The best analytical solution means nothing if the client isn't comfortable with it, if it doesn't feel right for their life. I spend as much time understanding the qualitative side as I do the numbers."
Outside the Office
Matt grew up in Austin, Texas, and moved to Connecticut in 2021. He lives in Ridgefield with his wife, Sarah, their 14-year-old twins and two dogs.
He's an avid runner, a skier, saltwater fisherman, enjoys a range of fitness activities, and is a passionate supporter of Broadway theater. He follows the English Premier League, a wide variety of live music, and, with characteristic analytical energy, has developed a fairly serious approach to maximizing credit card points for travel.
