Meet Dan: A Peacock Who Can't Fly, Tucker Carlson's Boat, and Dan Wilson's Road to CoFi
This week Wheeler and Colin sit down with Dan Wilson, CoFi Advisors' newest financial planning associate and a CFP® candidate, to get his full story — after months of him quietly feeding the show's news segments from his own five-newsletter-a-day habit. Dan likes to work backward, so they start with how he landed at CoFi (a LinkedIn search for "para-planner near Amesbury" while he was two years into a banking job at Chase) and trace it back through a genuinely winding career: a commercial-bank credit analyst role, weekend serving shifts at what's now Treehouse Brewing, two years in fintech sales at Toast right as the pandemic hit, two years running sales for Athletic Brewing in Arizona, and a remote stint at a home equity company before Chase and the CFP® track.
From there, the conversation traces Dan's actual interest in markets back to sophomore year of college — a copy of Stock Market for Dummies, a professor-mentor who ran the school's investment club, and a behavioral finance class senior year that pulled him away from spreadsheets and toward human decision-making. All three compare notes on their own first finance books (Rich Dad Poor Dad for two of them, The Wolf of Wall Street for the other), and Dan talks about growing up without much money talk at home, balanced against parents who prioritized his time over their careers. Since joining CoFi, the thing that's genuinely surprised him has been estate planning — trusts, and strategies like the intentionally defective grantor trust (IDGT), which he calls one of the more mind-bending things he's studied for the CFP®.
Colin runs Dan through a behavioral finance pop quiz on the Monty Hall problem — why switching doors after the host reveals a "zonk" actually improves your odds from one-in-three to two-in-three, and why that statistic is so much easier to accept than to feel, which becomes a stand-in for how clients relate to their own financial decisions. The back half turns personal: why Dan keeps a running folder of political news to track how fast the news cycle actually moves (with a nod to a line he attributes to Morgan Housel, "bad news is instant, good news is slow"), his belief that a good advisor stays neutral no matter who's across the table, and a detour to a canoe trip in Maine where he's fairly sure he nearly got run over by Tucker Carlson's boat. It closes on why none of the three can take a compliment, and the case for why that's actually a bad habit to have with clients.
Sources: this is a get-to-know-the-team episode rather than a markets week, so there's no Tuesday briefing to pull from. What's cited above is what's referenced directly on the recording — Rich Dad Poor Dad (Robert Kiyosaki), The Psychology of Money and the "bad news is instant" line (Morgan Housel), The Wolf of Wall Street (Jordan Belfort), the Monty Hall problem (a classic probability puzzle popularized by the show Let's Make a Deal), and the intentionally defective grantor trust (IDGT) as an estate-planning strategy. Send over anything else you'd like credited and I'll swap it in.
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Credits:
Created By: Wheeler Crowley and Colin Walker
Production, Editing and Post-Production: Tori Rothwell
