- Short Squeez
- Posts
- π Silicon Valley Richmogged the Roth IRA
π Silicon Valley Richmogged the Roth IRA
Plus: OpenAI is building a $30 billion data center in Georgia, $348 billion is trapped in zombie funds, and Mediterranean yacht rentals are cratering.

Together With
βGetting rich and staying rich are different things.β β Morgan Housel
Good Morning! JPMorgan and Goldman are set for $100 million paydays on SoftBank's $40 billion bridge loan for its OpenAI investment. Blackstone is tying up $3 billion to build AirTrunk's new data center in Australia, while OpenAI plans to spend over $30 billion on a massive new one near Savannah, Georgia.
A growing number of hedge funds and asset managers are eyeing a move from Singapore to Hong Kong and other low-tax cities to attract investors. AMD is investing up to $5 billion in Anthropic as part of a computing power deal. And private equity zombie funds hit a record, with over $348.5 billion stuck in funds at least a decade old.
Plus: Mediterranean summer yacht rentals are down 20% to 30% from last year, Miami is overtaking NYC in the return-to-office race, and how to spend less time thinking about money.
Get access to early-stage investment opportunities with Alumni Ventures. See their current deals.
SQUEEZ OF THE DAY
Your IRA Is Cute

The average American family has about $268,000 in IRA savings. But it turns out that Silicon Valley elites are richmogging them. More than 1,000 Americans now have IRAs worth at least $25 million, more than double the number in 2019. Around 11,600 people have IRAs worth at least $10 million, and roughly 200 Americans have retirement accounts worth $100 million or more.
And this is what happens when the retirement system meets startup equity, insider access and a once-in-a-generation tech boom.
The playbook many Silicon Valley elites are employing is buying private startup shares when they are worth basically nothing, put them inside a Roth IRA or another tax-advantaged account, wait for the company to go public, and let the gains compound without the usual tax bill. For normal people, the IRA is where you buy index funds and pray the S&P does its thing for 40 years. But for startup elites, it can become a tax-free venture fund.
For example, Gregory Baszucki, the brother of Robloxβs founder and a longtime board member, accumulated roughly two million Roblox shares in his Roth IRA years before the IPO at an adjusted price of 72 cents each. By the time Roblox went public, the stake was worth $141 million. His remaining Roth stake is valued around $68 million, and if earlier sale proceeds were reinvested, the account could be worth roughly $158 million.
Tench Coxe, a former Sutter Hill Ventures managing director and longtime Nvidia board member, has tax-advantaged retirement savings at an estimated $2 billion or more. He held Nvidia shares in retirement accounts from the days when the stock traded at a split-adjusted price of less than 3 cents.
The issue is not that people made great investments, because great investments should make people rich. The issue is that the biggest upside is mostly available to insiders who can access private shares early, value illiquid stock before the market gets a clean look, and then watch the gains compound inside accounts subsidized by taxpayers. Congress is now looking at forcing withdrawals from giant accounts above $10 million, because βretirement securityβ starts to sound a little different when the retirement account has nine zeros.
Takeaway: The Roth IRA was supposed to help normal Americans build a nest egg, but startup insiders figured out how to turn it into a tax-free venture lottery ticket. For most people, the contribution limit is the constraint. But for people with access to pre-IPO shares, it can be the entry point to a fortune that compounds tax-free for decades.
PRESENTED BY ALUMNI VENTURES
Invest in High-Potential Startups Like These
Alumni Ventures is giving readers early access to high-potential startup opportunities across todayβs most active sectors, co-invested alongside name-brand VC firms like Andreessen Horowitz (a16z), Bessemer, & Y Combinator.
You get:
Curated deal flow of high-potential startups
Invest alongside well known lead venture firms in these deals
No cost to see deals
No obligation to invest
Donβt miss your chance before access closes.
HEADLINES
Top Reads
JPMorgan, Goldman set for $100 million paydays on SoftBank's record loan (BB)
OpenAI plans to spend over $30 billion on Georgia data center (BB)
Blackstone tying up $3 billion AirTrunk loan as data center debt binge woes grow (BB)
Hedge fund stars look to quit Singapore for Hong Kong: AIMA (BB)
AMD and Anthropic sign major chips-and-investment deal (WSJ)
One great chart: the rise of the zombie funds (WSJ)
Renting a yacht in the Mediterranean this summer just got cheaper (CNBC)
Miami overtakes NYC in return-to-office race as companies expand South Florida footprint (Fox Business)
Morgan Stanley's $100 million SpaceX IPO payday was only a start (BB)
KKR-backed Vertis is said to be frontrunner for Megha Engineering Indian roads assets (BB)
Trump's push for American-made AI chips hits TSMC's margins (CNBC)
Private credit and data center wraps are 2008 redux (BB)
SpaceXAI explores major data center expansion in Texas (The Information)
The most important stock decision you'll make this year (BB)
Ray Dalio warned Elon Musk against betting all his money on Mars exploration β the SpaceX CEO said there was 'no need' for a financial backup plan (Fortune)
Citadel Securities opens Amsterdam options trading office (FT)
Deutsche Bank headquarters raided for third time this year (FT)
CAPITAL PULSE
Markets Rundown

Market Update
U.S. equities closed lower as investors weighed rising Middle East tensions, higher oil prices, and new tariff announcements.
The 10-year Treasury yield rose to 4.66% as energy prices moved higher amid concerns around supply disruptions.
The administration announced plans for a 100% tariff on imported generic pharmaceuticals beginning in 2028, while trade policy remains a focus ahead of the expiration of temporary Section 122 tariffs.
Investors are also watching Alphabetβs earnings report for updates on AI investment and spending plans.
Trade & Geopolitical Risks
Oil prices moved higher as negotiations between the U.S. and Iran showed limited progress, while disruptions around key shipping routes added supply concerns.
Recent tariff announcements have increased uncertainty, including additional tariffs on Canadian goods and proposed pharmaceutical import tariffs.
Despite policy uncertainty, markets have historically recovered from tariff-driven volatility, reinforcing the importance of maintaining a long-term investment approach.
Movers & Shakers
(+) Super Micro Computer ($SMCI) +20% after releasing results showing a record order backlog worth $60 billion in new orders.
(+) EQT ($EQT) +8% because the natural gas company raised its guidance.
(β) GE Verona ($GEV) -9% after Q2 earnings of $2.47/share missed the $3.13 consensus despite beating on revenue.
Prediction Markets
Jobless claims come out this morning at 8:30am EDT.
Trade on real-world events with Kalshi. Use code OWS to get a $10 bonus when you trade $10.
Private Dealmaking
Glow, an endpoint security company, raised $180 million
Humanoid, a London-based humanoid robotics company, raised $152 million
Candid Health, an autonomous RCM platform, raised $120 million
Cashea, a Venezuela-based banking and payments fintech, raised $100 million
Oak, an identity governance company, raised $60 million
Auger, a supply-chain software startup, raised $50 million
For more PE, VC & M&A deals, subscribe to our Buysiders newsletter.
BOOK OF THE DAY
You Can Just Do Things

Description:
A refreshing guide from Cate Hall and Sasha Chapin on developing "high agency"βthe belief that you can meaningfully shape your own circumstances. The book argues that many of life's biggest opportunities are missed not because of a lack of talent or resources, but because people underestimate what they are capable of creating. Through practical frameworks, real-world examples, and mental models, it teaches readers how to take initiative, challenge assumptions, solve problems creatively, and act decisively instead of waiting for permission.
Book Length: 304 pages
Release Date: June 3, 2025
Ideal For:
Entrepreneurs, builders, professionals, and anyone looking to develop greater initiative, overcome self-imposed limitations, and create more opportunities through action and ownership
The people who change their lives are often the ones who realize they never needed permission to begin.
DAILY VISUAL
Nolan Capital

PRESENTED BY MOSAIC
Bain: "PE Is Sitting on 32,000 Unsold Companies"
Bain's new Global PE Report put out a huge number: private equity is holding 32,000 unsold companies worth $3.8 trillion. After years of waiting, the exit window appears to be opening.
Medline's listing was the largest PE-backed IPO in history, corporate buyers are back, and Bain's survey of GPs indicates a belief in that momentum carrying through 2026. But buyers are still selective, and the deals getting done are the ones where the seller can back up the price.
PE firms are getting exit-ready in Mosaic, where a new Football Field tab adds a DCF, public comps, and precedent transactions to any completed LBO in one click, and the redesigned Deals View keeps models, metrics, and documents in one place for the whole team.
DAILY ACUMEN
Beauty Contest
Keynes once compared the stock market to a newspaper contest where readers picked the prettiest face from a set of photographs, and the prize went not to whoever picked the face they found prettiest, but to whoever picked the face that matched the majority's vote.
The winning strategy was never about your own opinion. It was about correctly guessing everyone else's opinion, and the sharpest entrants went further still, guessing what the average person expected the average person to think.
This is a more honest description of markets than most people are comfortable with. A stock does not move because it deserves to. It moves because enough participants believe enough other participants will buy it, layered several levels deep in mutual anticipation.
Fundamentals still matter, eventually, but over almost any horizon that matters to a career, the more useful question is rarely what is this actually worth. It is what does the crowd currently believe, and what will make the crowd change its mind next.
ENLIGHTENMENT
Short Squeez Picks
21 management habits that save time weekly
How to spend less time thinking about money
The career edge that no algorithm can take from you
The United States of luxury
Is an AI apocalypse coming?
MEME-A-PALOOZA
Memes of the Day





π£ Partner With Us: Get in front of an audience of over 1 million finance professionals, business leaders, and policy influencers. Submit a partnership inquiry.
π Wall Street Comp & Culture Data: Get the most detailed comp, carry, and culture insights across 1000+ Wall Street firms. Explore the data.
π Grow With Us: Work directly with the Overheard on Wall Street team to scale your finance brand. Schedule your free consult.
π§’ Wall Street Shop: Explore our collection of finance-themed apparel and merchandise. Visit the shop.
π¬ Deals Newsletter β Buysiders: A curated roundup of major M&A, private equity, and VC activity. Plus access to private deal flow. Subscribe here.
What'd you think of today's edition? |




Reply