Wealth & Tax Advisor to Early-Employees in late-stage Startups & Tech firms • Book a Call here ⤵️
Texas
Joined February 2010
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It's official, both @AnthropicAI and @OpenAI are set to IPO. And the smartest early employees are making their plans now.
But how?
Business Insider featured both @markcecchini and me for our top advice.
It's behind a pay-wall, so here are the highlights:
Last night, my 2 y/o son played hide & seek with my wife and me in the dark
and now I don’t remember ever having a fun moment before this moment in my lifetime
My friend works for the family business, and his father is finally looking to sell.
Idk the numbers, but I think it will easily clear $50M, could maybe touch 9-figs (gross).
I don't have anything to gain from it, they have a great wealth team, and I don't normally play in that sandbox anyways.
I just can't stop thinking about what this will do to him - the heir of a fortune.
He's in his late 30's, wife is a doctor. Small town, blue collar roots, unassuming wealth.
The father owns 100% of the biz. So as it stands, nothing will come to my friend.
Which means you're waiting 30-yrs to inherit Millions + a private jet (they already own).
What happens to your motivation? Your drive? Your purpose?
Do you retire your entire family? Does his wife - a doctor - stop practicing?
Everyone in your small town already knew you were well-off, but now there's no question. Who do you hang out with, besides your own family?
Wealthy folks are already on an island - it's a big reason why financial advisors have jobs. It's someone you can talk to about your wealth and it's affect on your life.
But if you plan to **inherit** a massive sum - what does it do to you?
If you've seen this in your life, and you've seen happy-cases come from it - what was their secret? what's your advice?
AI is making us soo much more-efficient
and also sooo much less-good at being a normal human-being and having smooth interactions.
My very (nay, most?) connected friend, Ryan, shared my LinkedIn
but it's my old white photo, and I have since gone to the dark side.
Bryan Hasling @bryanhasling
LI: linkedin.com/in/bryanhasling…
What they do: Wealth & Tax Advisor
Company Website: modernfp.com
How far out do you tell clients you’re going to be Out of Office?
Meet me where the light is… I’ll be playing six nights at @SphereVegas -solo, full band and trio.
April 8 • 10 • 11 • 15 • 17 • 18, 2027.
You can sign up now for the Artist Presale for your first chance at tickets beginning next Wednesday, October 7 at 10 AM PT at johnmayer.com
VIP Tickets and @VibeePresents Travel Packages on sale this Wednesday, September 30 at 10 AM PT.
I can’t wait to show you what I’m putting together. See you at Sphere.
Bryan Hasling, CFP® retweeted
Bryan Hasling @bryanhasling
LI: linkedin.com/in/bryanhasling…
What they do: Wealth & Tax Advisor
Company Website: modernfp.com/
It's been 105-days since the @SpaceX mega-IPO, and today was another shares release date.
41% of available shares from Early Employees can now be sold, transferred, borrowed from, etc.
I get asked a lot by other advisors what makes specializing in tech clients so different, challenging.
equity comp #1 is easily the big problem/puzzle we get asked to sort out.
ISOs/NSOs/RSUs/ESPP - these days you can learn these cold in a couple months, and use AI as co-pilot the whole way.
They simply have unique tax concepts (AMT, bargain elements, etc.), mixed with cash flow & goals, and wrangled together w/ overall risk & investing.
But let's be clear: tech ppl are not the only ones getting paid this way. Hundreds of non-tech companies/startup pay in equity comp!
So even though the basics are found in textbooks and online, people in tech really are unique.
-----
If you want to work with them too, here's what I've noticed makes them different:
1) they are generally younger, aiming for moon shots - not only are risk-appetites different, but time-horizons and ability to take risks (nay, *crave* risks) is just different.
2) concentration risk is normal, invited - this is kind of the same point as above, but it would stun most advisors how many of our clients have outsized concentration, and how comfortable they are with it.
3) they're weary of financial advisors - back to the youth part, tech wealth is usually 'sudden wealth.' They've never had enough complexity to have an advisor, and now all of a sudden they are bombarded w/ advisors in LinkedIn inbox :/
The stakes are high, the walls are high, and goal #1 is protecting themselves. It's hard to know who the good-guys are sometimes.
4) counter-culture is the culture - tech people aren't impressed by flash. They're impressed by how smart you are. The bay area was such a meritocracy culture-shock to me, versus the dallas old boys club I saw growing up.
It doesn't matter if you're in a t-shirt or in a class A office building. You're either smart or not, and people in tech can sniff out your merits, or façade, in a heartbeat.
When a prospect books a call, they answer a few questions from the set list.
from those few sentences, you can tell with almost-certainty if they are serious about this, kicking tires, or entirely not a fit.
If they are cagey and don't share basic info from the beginning -> they're not ready.
If they start off with me, my pricing, and what I do for clients (without them telling me any of their problems/symptoms) -> they're not ready (or will choose cheapest cost).
But for the ones who genuinely have needs and share openly - we have a real shot at:
a) giving you free advice on the spot (bc we want to help you!)
b) seeing if we get along. bc we have to get along as work-friends if we're going to be successful.
c) co-creating an arrangement that works for you.
Black polo gang
CC: @markcecchini
Mark Zuckerberg: the whole industry treats AI agents as a single-player game but the real unlock is agents interacting with each other, which Meta has been running internally
"Right now I think most of the industry is thinking about agents as like a single player game, right? It's like you have your agent and you use it."
"And there are going to be all these interesting things that basically you can do by having the agents interact with each other."
"And we already have all these interesting examples internally where people have their agents interacting with each other."
"This isn't, like, for the most part rolling out in this release, but it's going to be like an important part of how I think this works over time. As more of the people who you know start using Muse, it just gets better."
Just realized I haven’t worn a suit to work since I was an Intern.
These days I might even wear a T-Shirt to virtual meetings (only w my Tech clients).
Nice Polos most days.
I usually WFH in a clearly-extra bedroom of my home, and assume it would be bizarre if I wore a blazer to a virtual meeting?
Things that are impossible:
Buying a new Power Washer and only cleaning *one thing*
The entire house just got dealt with.
[my wife is the A. I’m the B]
This job is wild bc some days you’re discussing tax aware long-short to a deca-millionaire
But other days I’m sending reminders to create Schwab logins and setting a screenshare to help someone enroll in a 401k and update beneficiaries and addresses.
Yeah they can do all these things on their own. But it only count if you DO the thing. Even the little things, we do the things that matter.
Bryan Hasling, CFP® retweeted
Hi I’m a FA and Angel investor (part of a group).
SAFE by definition is not stock.
FE stands for Future Equity.
So you’d need a conversion event that turns it into stock, where’d you’d then have a Stock Agreement.
THAT begins the holding period.
For QSBS purposes: you look at the startups books/numbers AT THAT CONVERSION DATE for to determine if it’s QSBS-eligible.
Flipping to the dark side (my wife likes this one)
looks a little AI-ish but it’s just IRL lighting effects
When your stock options vest, Carta pushes out an email and says, hooray! you have options!
but what does this actually mean?
do you *have* to do something?
Options are, after all, just that - an option. A Choice.
You were just emailed a coupon-offer to buy startup stock at a discount.
Which sounds cool.... EXCEPT:
- - what if I never get my money back?
- - I might pay Tax on the diff b/w what I paid vs the stock price
- - I might not have the extra cash
Oh, and this coupon-offer has an expiration date.
The offer expires shortly after you leave the company (or get laid off🙃). If you do nothing, they are Gone forever.
To be successful with the decision,
you must think of yourself as a serious Angel Investor.
Do I have the Money to:
a) buy it and not rob from my other life goals?
b) pay the (potential) tax
c) wait for YEARS to learn if this played out? (or not)
If you answered Yes to all 3, exercising your equity could be right for you!
Carta continues to eat the startup equity-mgmt world.
Pulley - Carta's biggest competitor for startup cap table / early equity mgmt - is shutting down.
And now, they're sending all customers directly *to Carta*
I stand by my statement that most folks are better off *not* implementing Tax-Aware long-short strategies.
And I think Schwab raising minimums to $10m (temporarily?) helps reset a lot of the hype.
But even still, it *does* make a lot of sense for the right cases.
And the <$10m crowd who is makes sense for (who’s advisors are at Schwab) are left high-and-dry right now.
So even though I’m not a power-user, we need to know which custodians are available right now and what’s best for our clients / potential clients.
Lots of convos we’re having with our Tax-Aware partners. And might mean we have to add a backup custodian.
This album changed my life.
I’ll be honest, I didn’t like it at first. Didn’t get it. I liked the prior album and stuck to it.
Then over time, one by one, each song found their way into my life. Hitting a nerve I didn’t know anyone else had.
Then ‘Where The Light Is’ (Live at Nokia) came out, I bought the DVD. And I invested an embarrassing amount of hours - like hurt-my-GPA amount of hours - that year.
In guitar terms he was god.
I learned to play guitar after this. And I became quite good. I’ve performed live a few times.
I studied blues history, the greats, the sleeping giants.
I studied song writing. Shit, even appreciated drums, bass, harmony, and horns more after this.
My brain chemistry was forever-altered.
All bc I *felt* this music. I still do.
Sadly pop culture made it hard being a JM fan. in the late 2000’s / early 2010’s I had to hide my fandom. I’m still afraid of Swifties.
But here we are in 2026, and I’m a bigger fan than ever.
It hit me in my formative years and these songs, the ones before and after, all mean so much to me.
I don't usually celebrate album anniversaries. I have a hard time perceiving the past. I like now, and what's to come. But this album, that turns 20 today, changed my life. I'd had success already, but everything clicked into place on this album. I met some of the greatest musicians and engineers in the world and learned so much about making records from them. When I think back on what made the album so special, some thoughts come to mind, and they're worth my remembering: Life came into the room. I rode bikes on the beach. I was goofy - most of the images from these years are of me doing something wacky. The record took time. Months of writing, giving up on lots of songs, writing new ones, moving studios, taking breaks. As I get older l tend to expect results faster. I get frustrated a little easier. But it's always been the same; you work weeks and months on songs. Some don't make it, but it's never a waste of time. You live more life, you write more songs, and the process starts again. You cherish the tight little list of tunes that matter. When just one joins the ranks, it's a blessing. Joy wins out over discouragement. You have fun with your friends, who are all on the journey of exploring the unknown with you. Great albums are built in layers. You have to become different versions of yourself to create a lasting body of work. Nobody cares how long it takes if the music is meaningful. If you want to make something truly special, you have to bring talented people in the room to contribute. Steve and Pino. Chad Franscoviak and Joe Furla engineering along with Don Smith and Dave O'Brien. Martin Pradler editing vocals. René Martinez handing me the guitar. Ricky Peterson on keys, @jamesbvalentine played some guitar on Stop This Train. Larry Goldings played B3 and @aliciakeys sang backgrounds on Gravity. Roy Hargrove played trumpet.
Charlie Hunter played on In Repair. @BenHarper played slide guitar on Belief. Willie Weeks played bass with Pino on I Don't Trust Myself With Loving You. The right music with the right people at the right time in my life. That's all you can ever hope for. And thank YOU, dear reader, for giving life to these songs. Onward...
