Ally Jane( AJ) Ayers
Co-founder / Brooklyn FI / Brooklyn, N. Y.
AJ Ayers’ s career looks brilliantly mercurial on paper: A onetime journalist and book editor, she once worked for music platform Bandcamp writing record reviews and interviewing bands( anything with a guitar is good by her). Her financial success as one of the few creatives at this tech company got her interested in the subject of money( especially when it came to her own savings and stock options).
She started a podcast on explaining money, which she figured she could do well as a journalist, having a leg up as a communicator. One of her guests was Shane Mason, whom she describes as“ a cool accountant.” Eventually, the two figured they could carve out their own advisory serving musicians and artists. But that pursuit ended up instead unlocking prospective client lists full of young tech execs for the duo’ s burgeoning firm, which they had dubbed Brooklyn FI.
“ Shane had a boutique tax practice where he was doing 1040s for artists, photographers, musicians,” Ayers says.“ So the original intent was creatives. And then we discovered that a lot of those
creatives were married to product designers or marketers who worked at tech companies.”
When music platform Spotify( which had a New York office) went public in 2018, a piñata broke open, eventually offering Brooklyn FI dozens of clients.“ There were a lot of people with equity. A lot of people with tax problems. … So equity compensation just became our thing kind of pretty early on.”
Ayers says the employee compensation and liquidity landscape is ever-evolving, especially amid market turmoil.
“ There’ s this trepidation about going public. So a lot of these companies are staying private longer. So we’ re actually seeing a lot of tender offers. So I would say like, that’ s the trend in equity compensation right now. … A new investor comes in, founders don’ t want to dilute, so [ the investors ] offer a certain amount for existing employee owned shares or employee granted options for a set price.”
Ayers hasn’ t totally stepped away from entertainment topics: In one Wall Street Journal video a few years ago, she broke down the financial planning issues of Th e S o p r a n o s, looking at how a mob boss might diversify holdings.
Andy Baxley, CFP
Founder / Two Trails Financial Planning and BuilderFP / Chicago
Andy Baxley built his financial planning firm for clients standing at life’ s crossroads— not retirees, but people in their 30s and 40s balancing children, careers, aging parents and the nagging suspicion that financial success doesn’ t say what makes a good life.
That tension is embedded in the name of Baxley’ s firm, Two Trails Financial Planning— a nod to American poet Robert Frost and those times people have to choose roads not taken.“ It’ s meant to evoke a sense of possibility and creativity in financial planning,” Baxley says,“ and instill the sense that we don’ t necessarily have to do the thing our parents did.”
He was once a psychology major, envisioning a career in academia. But after graduating during the Great Recession and watching his parents struggle financially, he developed what he describes as an almost“ adversarial” view of money. While teaching English in South Korea, he began reading personal finance books simply to learn how to manage his own life better.
The subject quickly consumed him, wedding his three strongest interests: psychology, teaching and personal finance.
After early-career roles at Fidelity and TIAA, Baxley moved into the RIA world, where he found deeper client relationships but still felt constrained by the firms’ systems and structure. In 2024, he launched Two Trails to build the practice he could believe in: one designed specifically for younger accumulators whose financial lives are often more complicated than their balance sheets suggest.
Today, he oversees roughly $ 50 million in assets for about 37 households. He charges them based on income and net worth rather than just AUM, which fits a clientele of young high earners.“ The job is not so much to help people grow their net worth,” he says,“ but to help people live a great life and use money as a tool to do that.”
And increasingly Baxley is extending his influence beyond clients. He’ s also created BuilderFP, an advisor education platform that teaches fellow planners how to use AI. It’ s not merely about automating administrative tasks; he also shows them how to build custom tools and reimagine how their advice can be delivered. His virtual workshops sell out within minutes of being advertised on LinkedIn.
At heart, he remains what he nearly became in the first place: a teacher. Only now his classroom is larger.
36 | FINANCIAL ADVISOR MAGAZINE | MAY / JUNE 2026 WWW. FA-MAG. COM