🔴 I’m hosting a webinar with Burney Advisor Services tomorrow on RIA Channel about tax-aware long/short.
🔴 September 11, 2025 1:00 PM ET - 1 hour - LIVE - Register
WealthTech enters stache-mode
We’ve been here before.
Blockchain, the tech underlying Bitcoin, as a solution to… 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 don’t tell me blockchain solves a technical problem.
The same goes with gen AI.
It’s dubiously useful for prototyping, generating awful Studio Ghibli rips, and drafting terrible outbound emails. I call this the snapchatification or “stache-mode” 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 I’ve been baking at Future Proof.
“9 out of 10 gen AI-forward companies here won’t be alive in 3 years,” a senior operator told me, “but everyone is afraid they’re missing the wave.”
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 I’ve 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: “Go in-real-life to the max. AI can’t take that away.”
That’s a fact.
And I’m repeating his emphasis as a headphones-on-all-day software guy/tax code introvert. But I’m 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, I’m now behind on emails, research, client work, and family time.
My work also requires no-distraction, hard thinking, which simply isn’t happening here.
But those are temporary (costly!) sacrifices for relationships.
Most of the conversations I’ve had over the past two days have looked like:
Hi, how are you, you’re 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 you’re technically curious what people are asking me…
What people are asking me…
Tax-aware long/short SMA: How does it work? Won’t it ossify just like direct indexing? Do people actually need this? When? Aren’t the reports going to have tons and tons of line-items? Isn’t 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 (§351): Can I seed it with my Nvidia stock? Do I have to hold the shares for a year? What makes a §351 successful?
Selling tax-aware solutions: No one wants to… 1) look stupid, 2) sell something they can’t 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 “we must simplify things” 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
I’m judging you.
“9 out of 10 gen AI-forward companies here won’t be alive in 3 years,” a senior operator told me, “but everyone is afraid they’re missing the wave.”
I've been thinking this too, but what if... each of the 26 notetakers has gotten enough clients to survive, though not thrive... if someone is using one of the smaller ones, and it works decent, will they be inclined to move to Jump/Zocks/Wealthbox/Hazel, etc?