C0-Founder Insperis, the premier CEO community for scaling CEOs. https://xitter.cf/t.co/0PBr2TVeTT. 9x Founder. 2 great exits. 3x author. Urban farmer. “Gramps” at home.
Silicon Valley (San Jose) CA
Joined April 2018
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Have we met? If not, mea culpa.
First off, Hittler really is my name. No, really, it is.
My parents doubled the fun by buying our family home in a Jewish neighborhood. It was a counterintuitive genius move, as it forced all of us (9 kids) to figure out early what we stood for.
The result: I like people on purpose. Otherwise, I would have been in a fight every day or gone crazy.
Professionally, after 17 years coaching CEOs 1:1, one thing became painfully obvious: Founders don’t need another framework — they need a room of battle-tested peers who actually get it (and won’t BS you).
So four founders built Insperis.
Rap sheet: 9x founder/CEO (2 great exits) • 3x published author • ex-Forbes contributor.
Oddities: Kidnapped at 19 with my 1 yo daughter. Founded the first legal non-profit is Russia, right after 9/11. Won “whitest legs in Santa Cruz County” two years in a row.
Happily married, blended family of 7 kids (chaos level: expert), urban organic farmer, competitive athlete, foodie (wine pairing mandatory), and the kids call me ‘Gramps'.
On the feed: CEO scaling hacks, economics, politics, contrarian hot takes, and occasional humor that may or may not land.
No AI slop. Still trying to master functional intelligence.
Should we meet? DM me.
If you are selling credit card protection, or underbody rustproofing for my car, please DM my ex-wife.
The biggest CEO mistakes I made with equity funded companies were thinking we had a 2 or 3 year burn rate.
Time wasted = burned capital.
Figure out the steps to get to your next big milestone, and then ruthlessly cut out 1/3 of the steps.
You'll be amazed at how much faster you make progress.
Money is rarely the enemy. Time always is.
Q: What constraints are you putting on your speed of execution?
The biggest difference between SpaceX and Elon Musk versus NASA and the US government is speed.
NASA launches a rocket every once in a while.
Elon launches 100 rockets each year.
The only difference? Elon puts no constraints on launching every week.
Imagine what it must be like to be a rocket scientist with one launch per year, versus 100.
Now go and speed up your execution!
When it gets right down to it, any great CEO has to make trade-offs.
For those friends and peers who do not understand what you're gunning for, these trade-offs can look confusing.
Here's the rule: The bigger the trade-off, the bigger the win.
Any partial effort will become a loss, as you already traded up front.
Go all in.
Get the full win!
The most successful CEOs in our Insperis community have the highest self-belief.
Three reasons why:
1) Their self-belief is reflected in their actions.
2) Talent is always attracted to a leader with self-belief.
3) They can almost always sell.
Rate your self-belief.
Taxation is a disincentive….always.
People do not simply pay it.
They take action, like the 28.6% of CA billionaires who have left in time to avoid the tax entirely.
this California wealth tax thing is just incredible.
so in October 2025, a California healthcare union proposed a "one time" 5% tax on any billionaire's wealth. the ballot measure will be voted on next month. In early December 2025, California announced that it would be a retroactive tax if passed, applying to anyone with CA residency as of Jan 1, 2026. The objective is to pay for Medi-Cal, California's incredibly dysfunctional healthcare system. (which also functions as a glorified welfare apparatus, but that's a discussion for another time).
polls reveal that the CA electorate is split around 50/50 on the tax, but prediction markets only give Prop 40 a ~23% chance of passing (there are competing measures on the ballet that would nullify it).
there are 200 billionaires in CA, worth collectively somewhere between $2.3 and $2.6 trillion. 5% of that is around $100b, accounting for a small amount of attrition. proponents of the tax forecasted a significant windfall, assuming only a 10% departure rate.
supporters thought they were being clever with the retroactive concept. no billionares would leave CA in the few short months between the tax being proposed and the residency cutoff date, without the tax even having passed yet, right?
well as it turns out, they did.
a new paper [1] from two academics at Stanford called "The Net Present Value of the California Billionaire Tax Act", argues that not only did more billionaires leave due to the proposed tax than its proponents expected, but that the value of the tax, if it does pass, is actually negative.
proponents of the tax only assumed 10% avoidance, that is, only 10% of the taxable base of targeted billionaires would leave CA within the very short Oct-Dec 2025 window. Jaros and Rauh, the Stanford academics, find that a lower bound of 28.6% of the taxable base managed to leave.
just based on known departures, those departures total $577b in net worth, or $28.8b in potential tax lost. this of course does not capture everyone (many left without announcing their departure), so the authors normalize to departure rates estimated from other wealth tax events, and apply other discounts for litigation, arriving arrive at a figure of only $28-$36b in forecasted tax revenues.
but this isn't all! all of the income taxes paid by the departed billionaires are also forsaken. the authors estimate that CA billionaires pay $3.3- 5.8b in annual income taxes. they assume a midpoint of $2b lost in annual collections from departed billionaires. the net present value of that lost income stream is -$68.9 billion.
so when you add it all up you get:
+ $30b one-time tax windfall (estimated)
- $69b in present value of lost future income taxes
= - 38.9b overall net present value of the tax
of course, this analysis is highly estimate driven. the authors simulate the parameters 100k times and find a negative NPV of the implemented tax 85 percent of the time.
and if the tax doesn't pass, which it's not looking like it will, California still ended up losing at least $577b in departed net worth, and they have permanently poisoned the well with entrepreneurs who will now worry about future wealth taxes.
[1]: nber.org/system/files/workin…
The simple litmus test for systems and activities that scale?
If it get us closer to our goals - Keep it.
If it gets in our way in any manner - Cut it.
Do this for one month with every team, and see how much "addition by subtraction" your team will experience.
Then scale!
If prospects want to join Insperis for our membership roster, they are in the wrong group.
We help great CEOs get to a successful exit.
The members would be great for everyone to sell to.
We don't allow that. Ever!
We get two questions a lot:
- Why don't you share your membership rolls with guests?
- Why do you not have pictures of your events on your website?
It's simple:
Our members make the room work.
Our members in the room are the key.
Confidentiality then becomes the most important ingredient.
For great CEOs, the goal is not negotiable.
It's ambitious.
How you get there can take almost any form.
Tomorrow in Wash, DC, and Wednesday, Oct 28th in Silicon Valley, two of our CEO groups meet to improve their odds of a successful exit.
Exiting starts in your first year, and ends long after you cash out.
Insperis helps ambitious CEOs create successful exits.
Is that you?
It's truer now more than ever:
"Busy is the new stupid."
- Warren Bufett
What activities are you doing that fully qualified as stupid....ahem, busy?
How much does your biggest goal scare you?
If it does not scare you at all, you're playing (too) small.
Energy increases when you set an outrageous or impossible goal.
Play big or play small.
It's your choice and your life.
Unpopular opinion: If you are the sum of the five people you spend the most time with, who is on your list to go?
If you have more than two people who need to go, you are probably on other people's list to cut.
CEOs, how unreasonable are you in your expectations and execution?
Elon runs multiple trillion dollar companies because he sets no limits on expectations.
That starts at the top?
Are you unreasonable?
The best CEO I coach has this simple rule:
"In God we trust. All others require data."
Their organization simply makes better decisions than others.
I have founded and been CEO for 10 companies and exited nicely twice.
Both exits started with a handshake, not a big contract.
If your gut says it's not a good deal, a lawyer won't be able to protect you with a big contract.
My Grandpa used to give us little pearls of wisdom.
One of my favorites?
"Be the bigger person. Always end the fight."
He was my maternal g'pa, last name Hunter, so he knew that my siblings and I would face violence, since we lived only one generation after WW2.
We did get jumped and ganged up on as kids, always from boys, always 3 - 4 years older, and always outnumbered.
His wisdom was implied:
- Find a way to find common ground and settle your dispute with dignity.
- If there was no chance for the first outcome, knock the other guy out.
I prefer this first idea, and stand ready if things get rough.
