Matthew T. Streif, CEPA®
Managing Partner, Westport Wealth Partners
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 security 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 most 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:
A Client Story
One of Matt's long-term clients had been running their company for over 20 years. They'd never really focused on what the business was worth, there was always something more pressing to manage. When they started working together, the question was simple: if you were going to sell this, what would a buyer actually pay?
In the first year, they worked through the answer. Which metrics outside investors care about most in their industry. Where the business stood on those metrics. What the gap was between where it was and where it could be.
The next two years were spent systematically improving those metrics. Not by changing the business fundamentally, by building the story that an outside buyer would need to see.
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That's the kind of engagement Matt finds most meaningful: multi-year work that changes someone's financial trajectory, not a transaction completed and moved on from.
Outside the Office
Matt grew up in Austin, Texas, and moved to Connecticut in 2021. He lives in Ridgefield with his wife Sarah, his 13-year-old daughter Quinn, his 13-year-old son Tucker (twins), and their dogs Gus and Pig.
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.
