On a recent episode of the All-In Podcast, co-host David Sacks discussed two issues facing tech investors: why companies should be cautious about inviting government regulation and how to interpret the reported Stripe and Advent joint takeover offer for PayPal at a price of roughly $60 per share.
Sacks, the White House AI and Crypto Czar and a longtime Silicon Valley investor, argued that tech executives who ask Washington to regulate their industries might end up ceding more control than they expect and hurt the entire industry in the process. “When you go to the government and say, please regulate me, you know, you should have more power, there’s hardly anyone in government who will ever say, oh no, no, no, we’re not qualified,” he said. His warning to founders and boards is that once oversight is offered up, the government will “come back for more and more and more until it’s fully under government control.”
“Grow a Spine:” Sacks Warns Tech Leaders Against Inviting Regulation
Sacks urged tech leaders to “grow a spine” and draw a firm line on scope. His view is that a self-regulatory organization can be workable, but only if companies demand legal preemption in exchange for any SRO framework, rather than offering oversight freely.
For investors, regulatory posture is now a material input into fintech and AI platform valuations. Payments companies sit at the intersection of consumer protection, banking, AI agent commerce, and stablecoins, which are all potential avenues for Washington to add more regulation.
Stripe and Advent Reportedly Open With a $60/Share Bid for PayPal
Co-host Jason Calacanis said on the same segment that Stripe and private equity firm Advent are jointly offering roughly $60 per share to acquire PayPal, with Block potentially joining the bid. Calacanis described the $60 level as a low opening bid, with most observers expecting a final price closer to $70.
Several investors argue that a $60-per-share offer would significantly undervalue PayPal. On his Substack, “The Big Short” investor Michael Burry called the reported bid “simply too low” and “only an opening bid.” He said he is holding his shares and values PayPal at $75 to $115, with a best estimate near $100. Thomas Hayes of Great Hill Capital went further, arguing that even a bid above $80 would still undervalue the company.
PayPal (NASDAQ:PYPL | PYPL Price Prediction) trades around $56.56, with a market capitalization near $49.89 billion. Shares are up 22.11% over the past week and 34.41% over the past month, though still down 22.76% over one year. In its Q1 FY2026 report, PayPal posted non-GAAP EPS of $1.34 on revenue of $8.353 billion, up 7.2% year over year, with total payment volume of $463.95 billion across 439 million active accounts.
Prediction Markets See a 69% Chance PayPal Gets Acquired
Prediction markets on Polymarket now imply a 68.5% probability that PayPal is acquired before 2027, a 52.5% probability that Stripe acquires any part of PayPal in 2026, and only a 30.1% probability of a full Stripe-PayPal deal in 2026.
Chamath Palihapitiya noted that the deal’s complexity shifts significantly depending on whether Block is involved, and that media reporting has been inconsistent on this point. PayPal’s ew CEO Enrique Lores said he is “energized by the opportunity to improve execution and accelerate PayPal’s growth” and is “taking deliberate steps to sharpen our strategy, simplify our organization, and improve both our growth trajectory and cost structure.”
Block Could Join the Bid and Complicate the Entire Deal
Block (NYSE:XYZ), Jack Dorsey’s parent for Cash App, Square, and Afterpay, sits at roughly $79.94 per share and is up 22.81% year to date. Q1 FY2026 delivered adjusted diluted EPS of $0.85 and Cash App gross profit of $1.91 billion, up 38% year over year. Management raised FY2026 guidance to gross profit of $12.33 billion and adjusted diluted EPS of $3.85.
Chamath’s point about Block matters because Cash App competes directly with Venmo. If Block joins the consortium, antitrust review lengthens and the deal shape changes, which is why the partial-acquisition Polymarket sits materially above the full-deal contract.
What to Watch
Sacks’s broader message is that companies should negotiate carefully with both regulators and potential buyers. Tech leaders should seek federal preemption before supporting new regulations, while PayPal investors should watch whether the reported $60 opening offer is confirmed and eventually moves closer to the roughly $70-per-share price observers expect.
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