I read a piece recently about all the things that can surprise you when you start an independent advisory firm.
It read a little like a warning.
I don’t blame them.
I’ve been known to deliberately scare the bejesus out of people who tell me they’re thinking about becoming a financial advisor, let alone starting their own firm.
Recently, a good friend and client asked if I’d talk with a friend considering becoming an advisor.
I was triggered. And I mean that in the most respectful way.
Because this is hard.
Borrowing from one of my favorite movies, A League of Their Own, the hard is what makes it great.
I got his number.
“All right. I’ll call him tomorrow morning.”
And I did.
If he picks up or returns my call, we’ll talk.
One shot.
I’m not trying to be a hard-ass. I’m making a point.
Details matter. Following through matters. Responsiveness matters.
The big things are usually obvious.
It’s everything else that gets missed.
The Predictable Shouldn’t Become Urgent
I’ve been running Hilpan Moxie since 2012. August was one of those months that reminded me the building never really stops.
We became an SEC-registered investment adviser.
We ended 2025 with just over $97 million under management, so we knew this was coming. After talking with our compliance consultant, we decided to file early rather than wait until the transition became necessary.
Now we’re preparing for what comes next, including mock SEC examinations, finding our own gaps before an actual examiner does.
We’re rebuilding our website, too.
The old one served us well. But the practice had outgrown it.
The website needed to catch up with the firm.
Meanwhile, client work kept moving.
We reviewed Treasuries coming due and bought new paper with maturities in Q4 and early next year.
Why?
Because RMDs are coming.
September estimated taxes are coming.
We’re coordinating with clients’ CPAs and tax advisors now, including making tax payments from client accounts where appropriate.
I’d rather think about a cash need months early than figure out what to sell the day the money has to go out.
The predictable shouldn’t become urgent.
Less Retrieval. More Presence.
August also gave me a chance to think about where this profession is going.
I joined Zeplyn for a webinar about how AI can support advisory firms. Zeplyn CEO and co-founder Era Jain is a Xoogler, a former Google AI engineer who went on to build a company for wealth managers.
Going into the presentation, I had one North Star:
AI remembers the facts so that we can remember the person.
Let technology retrieve what someone told us six months ago. Organize the information. Help prepare the meeting. Surface what we might otherwise miss.
Then let us be present.
Less retrieval. More presence.
I also spent time with another Xoogler, Erika Ho, who spent 10 years in marketing analytics at Google, became work-optional in her 30s, and now helps women in tech think through the path to early retirement.
We kept coming back to a deceptively simple question:
How much is enough?
I’ve had a front-row seat to the arc of a lot of Googlers’ financial lives.
Joining Google. Building wealth. Retiring. Moving overseas. Starting businesses. Figuring out what comes next.
At some point, the math can say you’re fine.
That doesn’t necessarily mean you feel fine.
Our work approaches that question from different places. I spend more time on the longer arc: investments, taxes, retirement and how those pieces fit together.
Erika gets closer to the day-to-day: cash flow, accountability, spending decisions and someone’s relationship with money.
A spreadsheet can help answer one version of “Is it enough?”
It can’t answer all of it.
I have a feeling there’s something interesting there. I’m looking forward to finding out.
Know When Someone Else Knows More
Era and Erika have taken very different paths since Google.
Google may be where someone builds wealth.
It doesn’t necessarily tell you what they’ll build next.
And when I finished writing this month’s piece about why I bought long-term care insurance at 41, I sent it to Cathy Flanagan, an LTC specialist I’ve trusted for years.
My message was basically:
What am I missing?
She found two things.
Insurability and inflation.
She was right.
I rewrote it.
Twenty years in financial services doesn’t mean I know everything. It means I’ve had twenty years to learn how important it is to know when someone else knows more.
Maybe that’s what August was really about.
The practice changed.
The regulation changed.
The technology changed.
Our clients’ lives keep changing.
So we keep building.
Not because what’s here isn’t working.
Because what got us here isn’t the finish line.
This content is for educational and informational purposes only and should not be considered personalized investment, tax, or legal advice. Each situation is unique and should be evaluated individually.