š“ Iām hosting a webinar with Burney Advisor Services tomorrow on RIA Channel about tax-aware long/short.
š“ September 11, 2025 1:00 PM ET - 1 hour - LIVE - Register
WealthTech enters stache-mode
Weāve been here before.
Blockchain, the tech underlying Bitcoin, as a solution toā¦ what exactly?
Own Bitcoin if you want schmuck insurance via the cockroach of the financial system, or to speculate, or exposure to some new store of value, or whatever, but donāt tell me blockchain solves a technical problem.
The same goes with gen AI.
Itās dubiously useful for prototyping, generating awful Studio Ghibli rips, and drafting terrible outbound emails. I call this the snapchatification or āstache-modeā of everything.
No serious person I know uses it for anything having a dollar sign without domain expert oversight.
But gen AI hype is as relentless as the sunshine here in Huntington Beach, CA, where Iāve been baking at Future Proof.
ā9 out of 10 gen AI-forward companies here wonāt be alive in 3 years,ā a senior operator told me, ābut everyone is afraid theyāre missing the wave.ā
Not me.
Most Gen-AI-forward companies in wealthtech have pivoted back to the comforts of deterministic, no-hallucination outcomes.
As it has always been, the real work in wealth is building relationships.
The best stories Iāve heard over these two days are about old-fashioned DC lobbying, coordinating on the phone with trading partners to achieve best execution, and talking face-to-face.
Josh Brown: āGo in-real-life to the max. AI canāt take that away.ā
Thatās a fact.
And Iām repeating his emphasis as a headphones-on-all-day software guy/tax code introvert. But Iām still aggressively nodding at the value of networking and figuring out ways to collaborate in person.
I give you permission to zone out from gen AI religiosity until a killer app emerges.
What does Future Proof cost?
Set aside expenses, Iām now behind on emails, research, client work, and family time.
My work also requires no-distraction, hard thinking, which simply isnāt happening here.
But those are temporary (costly!) sacrifices for relationships.
Most of the conversations Iāve had over the past two days have looked like:
Hi, how are you, youāre a Mariners fan? What is Tax Alpha Insider?
Hi Brent, how does XYZ tax thing work, and who solves it best?
Brent! Good to see you. How can we work together on ABC?
This is productive, and the meatier stuff happens much faster in person.
If youāre technically curious what people are asking meā¦
What people are asking meā¦
Tax-aware long/short SMA: How does it work? Wonāt it ossify just like direct indexing? Do people actually need this? When? Arenāt the reports going to have tons and tons of line-items? Isnāt this just active management? What could go wrong?
Trader funds: What are they? How do they work? Are the fees deductible? Who needs them?
Borrowing via box spread: How does it work? What are the tax advantages beyond a traditional securities-backed line of credit? When would I ever need something like this?
Private debt/credit, interval funds: What are they? Do I get a 1099 or K-1? What are some tax solutions?
Solutions to concentrated stock positions: What should we know about besides direct indexing? How does a variable prepaid forward work? Should we be looking closely at opportunity zone funds?
Seeding ETFs in-kind (Ā§351): Can I seed it with my Nvidia stock? Do I have to hold the shares for a year? What makes a Ā§351 successful?
Selling tax-aware solutions: No one wants toā¦ 1) look stupid, 2) sell something they canāt explain. How do we get advisers up to speed so they feel confident answering nuanced client questions about this stuff? How does all this complexity fit into the āwe must simplify thingsā mentality?
These are nerdy technical things. But most of my conversations were about projects and partnerships, not about the nuts-and-bolts concepts above.
I think Future Proof was worth it.
Overheard some guys talking about their ETFs distributing 59.7% for only 0.99%/year.
EBITDA
ee-bit-dah vs. ee-bih-duh
bips vs. beeps
Iām judging you.