Dear Tech Bros: Stop Whining about Wealth Taxes and “Get in the Arena”
"Accelerationists" should be advocating for a tax code with the dexterity to adapt to a world of abundant AI.
Dear Tech Bros: Stop Whining about Wealth Taxes and “Get in the Arena”
A few weeks ago, I wrote a piece arguing that Elizabeth Warren has the right diagnosis (billionaires pay lower effective rates than teachers, “buy/borrow/die” is indefensible) but the wrong prescription: a wealth tax is a new system bolted onto a 75,000-page mess that already doesn’t work. Right problem, wrong solution.
Today I want to point a similar critique in a different direction: the indignance that “tech bros” have shown towards various efforts to tax extreme wealth.
Take, for example, the All-In Podcast. When it was first launched, All-In was one of my favorite pods. I appreciated the raw, unfiltered, often contrarian takes on what was happening in the technology markets. Four experienced and outspoken perspectives, different ideologies, stress-testing each other in public. It was a good product.
But somewhere along the way the “first principles” they regularly espoused became “me-first principles.” Chamath and Sacks went all in on Trump-era sycophancy, despite having said after January 6 that he should be barred from public office. The show veered hard into politics, and the obvious hypocrisy and political tone-deafness of four very rich guys became overwhelming. So I stopped listening.
But lately, I’ve caught wind of their latest target of indignation: wealth tax policy. If Senator Warren is offering the wrong answer to extreme wealth inequality, the All-In guys are offering no answer. And refusing to propose anything while complaining about everything is, in some ways, the more frustrating posture. It abdicates the chance to actually shape the outcome.
The whining problem
As All-In’s “friend-of-the-pod” Ray Dalio has repeatedly pointed out, extreme wealth disparity never ends well. His framework, built on 500 years of historical data, identifies wealth concentration at current levels as a leading indicator of internal conflict and political rupture. Not a leftist talking point. Just the data.
Efforts to curb extreme wealth disparity are gaining momentum across the country, with bespoke laws being introduced state by state. In March 2026, Washington state passed SB 6346, a 9.9% income tax on personal earnings over $1M. Massachusetts passed a 4% millionaire’s surtax in 2022, Mamdani won in New York running (in part) on a pied-à-terre tax and an income surcharge, Seattle has its JumpStart payroll tax on high earners at large companies, and California is now moving toward a 5% wealth tax on net worth over $50M.
The All-In crowd’s responses to these policies has ranged from:
“You’re driving away the job creators.” (Sacks: “Democrats steal everything, then blame job creators for their ‘greed.’”)
Move to Austin / Miami / Nevada, it’s great. (Musk to Texas, Lonsdale to Texas, Page and Brin to Nevada, Schultz to Miami.)
Mamdani is a socialist. So is California. (Brin: “I fled socialism with my family in 1979 and know the devastating, oppressive society it created in the Soviet Union. I don’t want California to end up in the same place.”)
You can’t tax unrealized gains! It’s asset seizure! (Sacks, again: “This is not a tax — this is asset seizure. It’s not a one time, it’s a first time.”)
We need to cut waste, fraud, and abuse. No taxes needed. (Sacks, again: “Why does California need a wealth tax? To fund the massive fraud. Red states like Texas and Florida don’t even have income taxes.”)
Just unleash AI and the deficit takes care of itself. (Friedberg: “If we have enough power, the $38T of debt doesn’t matter.”)
That is not a “first principles” policy response. It is scattershot complaining devoid of self-awareness.
To steelman: their actual position is not “inequality is fine” or “the deficit isn’t a problem.” It is closer to “growth solves everything” plus “there’s too much fraud and waste.” No need for new revenues. Cut taxes, cut regulation, grow the pie, everyone wins. Your slice may shrink as a percentage, but the pie grows so much that your slice is bigger in absolute terms than it ever was.
The problem with this view is twofold. First, as Dalio exhaustively chronicles, “growth lifts everyone” works only up to a point. Past a certain concentration threshold, the political and economic system itself becomes the bottleneck. Second, growth alone cannot close a deficit gap this large. CBO’s long-term projections consistently show structural deficits even under optimistic productivity assumptions. Growth and cost cutting are both necessary. They are not sufficient. Revenue will need to be part of the answer. (More on the math of deficits in a future post.)
You can dismiss any one of these state-level policies as a local fluke. You cannot dismiss all of them. There is a political groundswell gaining momentum around wealth disparity, as there has been many times before in history. And when the tax-the-rich movement goes federal (and I think it will), the pied-à-terre in Miami doesn’t help. Howard Schultz would have to move to Dubai instead of Florida. That is a much harder sell.
So rather than just complaining, how about a) recognizing the social risks of wealth disparity and a runaway federal deficit, and b) actually proposing some viable, systems-oriented “first principles” alternatives to these hacky, one-off state tax policies?
First principles, actually
So basically the All-In response to taxing wealth is “we earned it, leave us alone, let us cook.” Here’s why that frame leaves out some load-bearing facts.
1. You did not build this alone. The internet you got rich on came out of DARPA-funded research from the 1960s onward, with tens of billions of federal R&D dollars over decades. The semiconductor industry was built on Bell Labs (effectively a regulated public utility), DOD procurement, federally-funded basic research, and most recently the $52B CHIPS Act. Your educated workforce came out of public universities and federally-subsidized student loans. Your contracts get enforced by federal courts. Your products ship on public roads. Your IPO got cleared by the SEC. None of this is socialism. It is just true. The point is not “you owe us.” The point is that the system that made you rich is a system, and a system needs maintenance. (More reading: Mariana Mazzucato’s The Entrepreneurial State.)
2. Luck did more than you think. I am not saying you are not talented or hard-working. You deserve to be incredibly wealthy. But I am saying that while talent and hard work are necessary, they are nowhere close to sufficient ingredients in your financial success. The gap between “talented” and “lottery winner” is highly random. And a society that taxes luck-dependent windfalls more than effort-driven income is, if anything, more meritocratic than the current system. Not less. (More reading: a 2018 paper by Pluchino, Biondo, and Rapisarda in Advances in Complex Systems simulates 1,000 agents with normally-distributed talent and randomly-distributed luck. The most successful agent had a talent score of 0.61. The mean was 0.6. The most talented agent, at 0.89, ended up below average in success. The Pareto-distributed wealth tail is almost entirely luck-driven.)
3. Wealth begets wealth. Once you are already rich, your next venture has a massive advantage over the kid in the dorm room with the same idea. You take less risk. You stay rich if it fails. You can self-fund. You can absorb losses. You can wait out bad markets. You have the network. TThe current tax code amplifies this advantage (step-up basis, the buy/borrow/die playbook, perpetually lower capital gains rates than ordinary income). If you actually want a meritocracy of ideas, advocate for one.
4. Pay attention to history. As noted, Ray Dalio wrote the book on this: Principles for Dealing with the Changing World Order. His framework actually identifies two parallel risks: extreme wealth concentration and unsustainable debt. Both are at historic levels right now. Both are addressable through the same set of structural tax reforms. (More on that in a future post.) Extreme concentration ends the same way every time: 1789, 1917, the 1930s. The U.S. avoided that fate during the Depression by passing the New Deal, which is to say, by reducing concentration through policy. This is not a leftist talking point. This is pattern recognition from the guy you keep quoting.
And now, the AI part
Your investment thesis repeated in one form or another basically every episode is that AI will unleash an unprecedented period of economic growth and we can grow our way out of the deficit.
If you are right, then:
Labor market disruption hits faster than any retraining or social safety net can absorb. Calacanis himself has talked about young workers (20–24) seeing unemployment spikes from AI replacement. Right now. Pre-hockey-stick.
Wealth concentration accelerates dramatically. AI markets concentrate even more aggressively than software markets did, because frontier model development is a multi-billion-dollar fixed cost only a handful of companies can absorb. The companies that own the models and the chips capture an obscene fraction of global productivity gains. Meanwhile, the writers, artists, and journalists whose work was used to train those models are not being compensated at all.
The political response to an increasing gap between the uber-wealthy and everyone else will be aggressive and populist - the seeds of which we are already seeing in state policies.
AI’s public reputation is already in the toilet. Pew polling shows 52% of Americans more concerned than excited about AI, against just 10% more excited than concerned. You are about to ride a productivity boom into a country that already does not trust the people building it. If the productivity gains visibly accrue to the same fifty people while everyone else watches their job get automated, you don’t get a wealth tax. You get something worse.
If you actually believe your own thesis, you should be the loudest voices in America for a tax code with the dexterity to adapt to a new world of abundant AI.
Six things you should be loudly for
Here are several centrist ideas that a true AI accelerationist and “first principles system thinker” should support:
1. Portable benefits. Healthcare and retirement decoupled from employer. Workers carry them across jobs. Better for the gig economy, better for entrepreneurship, better for AI-driven labor disruption. Why is this not a libertarian-coded position already? It should be. Friedberg, shouldn’t this one be right in your wheelhouse?
2. A radically simpler tax code. No itemization. No phase-outs. Close the loopholes. Kill the alphabet soup of credits and deductions. Automate everything. Compliance costs in the U.S. run $536B per year. That is pure deadweight. A multi-billion-dollar tax prep industry exists because the code is absurd and byzantine. Imagine a tax return that fits on an index card. (I have a draft.)
3. FICA reform. The wage cap is currently $176,100. Anyone earning above that pays exactly zero additional Social Security tax on the next dollar. So a worker making $80K pays FICA on every dollar of wages; a hedge fund manager pays it on a tiny fraction of theirs. This is a regressive tax pretending to be a flat one. Lift the cap. Pair it with progressive benefit adjustments at the top so it is not a pure transfer. (Romney proposed something close to this. So have several Senate Democrats. The bipartisan version is right there for the taking.)
4. Universal Savings Accounts. Collapse the alphabet soup (401k, 403b, IRA, Roth, HSA, FSA, 529, Coverdell, ABLE, SEP, SIMPLE…and Trump Accounts) into one Roth-style account everyone has from birth. Same tax treatment. Same contribution limits. Portable. Simple. This should be a libertarian fever dream and instead nobody is championing it.
5. Close buy/borrow/die. Death is a realization event. Step-up basis ends. A lifetime capital gains framework with a meaningful exemption (so we are not chasing middle-class retirees) and a clean transition (no retroactive tax on gains accrued before the change). This is the alternative to a wealth tax. It taxes realized gains instead of trying to value an illiquid asset every year, and it runs on infrastructure the IRS already operates. Even Tucker Carlson, who like Dalio has been on the show and is a “Friend of the Pod,” has been openly questioning why capital gets taxed at half the rate of labor. He raised it again in his recent NYT Daily interview, talking about “the true hoarding of capital by a tiny group of people.” When the populist right starts asking that question, the political coalition defending the current treatment is already gone. You just haven’t noticed yet. (Yes, closing buy/borrow/die would cost some of you money. Be honest about it. The alternative is not “no change.” The alternative is a wealth tax designed by people who do not care about capital formation. Better to negotiate now while you still have leverage than to have a worse version forced through later.)
6. Separate tax collection from social policy delivery. The tax code is currently asked to do two completely different jobs: collect revenue and deliver social programs through deductions, credits, and phase-outs. EITC. Child Tax Credit. SNAP eligibility tied to income calculations. 80 different overlapping programs disguised as tax provisions. AI is going to make Congress’s instinct worse, not better. The first response to AI-driven job loss will be a bolt-on: “AI Displacement Credit,” “Reskilling Refundable Deduction,” “Uncompensated Training Data Offset.” Each one well-meaning. Each one adding to the sprawl. The structural alternative is to separate the concerns. Tax code does taxes. A direct, simpler mechanism (UBI being the most discussed candidate) does distribution. Same architectural move you should already support for savings (USAs instead of the alphabet soup) and for taxation (a simple code instead of 75,000 pages). One principle. Three domains. (More on what comes after simplification in a future post.)
Some people are actually getting in the arena
And in case you think nobody from your demographic ever does this, let me name a few extremely wealthy people who have, to use Chamath’s phrase, “gotten in the arena.”
In December 2025, Mitt Romney wrote a New York Times op-ed titled, in essence, “tax me more, I was wrong before.” He called the loopholes “tax caverns.” He named carried interest, the FICA cap, real estate depreciation, and the stepped-up basis on inheritances over $100M as specific things to fix. He used Elon Musk as an example of how the current system breaks. He is a former Republican presidential nominee and former Bain Capital founder, and he put his name on a concrete list. The WSJ editorial board attacked him for it. That is what taking a real position looks like.
Mark Cuban, who paid $275.9M in taxes in 2023 and was proudly public about it, has been actively advising campaigns on capital gains policy. He talked Harris down from Biden’s higher cap gains proposal because he can articulate why higher rates discourage investment in early-stage, riskier companies (especially those started by women, people of color, and recent grads). He disagrees with Warren on unrealized gains. He thinks billionaires should pay more under the current realization-based system. That is a coherent position with specifics. You can disagree with it. It is in the arena.
Bill Gates and Warren Buffett have been publicly arguing for years that people like them should pay more. Buffett’s Berkshire Hathaway paid a record $26.8B in federal taxes in 2024. The “Buffett Rule” was a specific proposal with a number attached.
You do not have to agree with any of these people. But they made proposals. They put their names on something concrete. They got attacked by their own side and held their position. That is what “getting in the arena” looks like.
Your move
I would love to hear an episode where you engage seriously with tax reform and make concrete proposals. Not “Mamdani is a socialist” or “Warren is a hypocrite” or “Come join me in Austin,” but rather a 30-minute thought experiment about tax reform that would actually work in concert with the growth of an AI economy.
The wealth tax movement is going to keep gaining momentum. Societies simply will not tolerate our current levels of wealth disparity forever (see Dalio, once again). So acknowledge the diagnosis. Stop defending bolt-ons. Propose systemic fixes. Get specific.
Get in the arena, guys.