Rebecca Reeve Henderson

Warren Buffett, in his first sit-down since stepping down as Berkshire CEO, gave the cleanest indictment of legalized gambling in a decade. He called it a tax cut for the wealthy. The math proves him exactly right. Americans wagered $165 billion at legal sportsbooks in 2025. They lost $16 billion of that. FanDuel pulled $6 billion of the losses. DraftKings pulled $5.3 billion. Every state with legal mobile sports betting collected a tax on the bettor side. New York alone took in over $1.2 billion in 2025 sports betting tax revenue. Layer the lottery on top. State lotteries generate over $90 billion a year. The bottom half of income earners account for roughly 70% of total spend. The average lottery player makes $38,000. A household earning $20,000 spends three times more on tickets than one earning $30,000. The implicit tax rate, meaning whatever the state keeps after prizes, runs 30 to 50% depending on the game. No other revenue source in America has that base and that rate. The structural design is the engine. A single straight sports bet carries a hold of 4 to 5%. A four-leg parlay carries a hold above 30%. FanDuel and DraftKings spent five years rebuilding their apps to make parlays the default product. FanDuel's blended hold rate hit 11.4% in 2025, up from roughly 7% in 2022. The product got worse for the customer and the customer wagered more anyway. Now look at the substitution. Nine US states have no state income tax. Seven of those nine run state lotteries. Seven of those nine have legalized sports betting. The states most committed to never taxing wealth are the same states running the largest extraction machines on people who cannot afford to lose. Read it as policy. Here is what Buffett is actually pointing at. The state needs revenue. It can raise income tax on the top decile, or it can run a lottery plus a sports betting tax. The second option raises the money from the people who can least afford it. The first option becomes politically optional. New York's $1.2 billion in 2025 sports betting tax is $1.2 billion the state did not have to ask of someone earning $5 million. DraftKings and FanDuel sell a privatized collection mechanism for a regressive tax that the state never has to defend at the ballot box again. Voters approve legalization once. Collection runs forever. The state takes a cut. The wealthy get a quieter top bracket. The bettor's cut shrinks every quarter as the parlay menu gets pushed harder. The function of a government, Buffett said, is not to play its people for suckers. Thirty-nine state governments now do.

@MikeIsaac I'd read an article about why this hasn't been a regulatory priority. My phone is essentially bricked.

(as an aside, feel like someone running on a platform of "i will imprison Autodialing businesses and owners of headlights that are too bright" would sweep the presidency in 2028 still insane to me this hasn't been solved from a regulatory POV)

b/c i get an unconscionable amount of spam calls i subbed to the app "hiya" but turned on call screening thing which prompts people unknown numbers to record their name before it goes through to me & worried ill miss real calls do you auto hang up if you hear those screeners

America First? Not When It Comes to Your Health. nytimes.com/2025/08/24/opi… via @NYTOpinion

@wennmachers @a16z Congratulations! I remember reading the news about you joining A16Z and how gobsmacked I was about what was possible for comms in Silicon Valley. You led the way!

Time for a Margit update! Here is the news: I’m “graduating” from operating partner to partner emeritus @a16z. First, let me back up. It seems that I do things in decade and a half increments. I got to the US in 1991 (October 19 is like a sort of birthday. Ask any immigrant and they will know their US birthday!). There was a tech recession at the time. Also, no American resume. Nor academic credentials. But this is America! And it came through for me. I spent a few years trying to get a job. I got a temp job at a tech PR firm. Then I got my first real break. A huge thank you to @simonecoxe and @maureenblanc for giving me my first real job and a shot at an actual career. That was a job as Account Executive at Blanc & Otus. I worked there for 4+ years. Then the talented @carynm650 and I started The Outcast Agency, which turned out to be the very best tech comms firm in the world. We built Outcast into the most sought after firm for tech franchises for over a decade and a half. We sold it to Nextfifteen (thank you, @timdyson . So that house was built; it’s still around and has amazing clients. @bhorowitz and @pmarca came calling. Before they ever raised money. These guys were ballsy. It was the height of the financial crisis, there was zero liquidity. Ben and Marc wanted to raise $300m. Just the two of them. When probed on this, Marc just said, “Let’s assume success, shall we?” Despite the risk…. It was a chance to build the top brand in venture capital. Period. Mind you, back then no VC firm was doing any marketing at all. It was seen as almost unseemly! I love building so I took a chance. The founders made me - I think - the first VC firm CMO. Now every firm has one of those, and that’s a good thing. Over the last 15 fabulous years, we’ve done so many things: - We marketed ahead of any result. We had to. So we marketed people and their ideas. - We invented going direct, creating a powerful content operation that allows us to communicate on our terms. - We produced events where people tried to crash multiple times and had to be escorted out by security. - Literally so many firsts and big things, there are too many to list them all. Now we actually have results! And we’re still the most exciting brand. a16z is full of talented people giving their best, full of amazing portfolio companies, and a very large and powerful network that everyone in our orbit can plug into. I can’t possibly thank every single person in the firm here, so I will keep it to the founders for being committed to building the top brand, and to @garcegarce of course. She was my first hire - she also took a chance on me and our entire project. Finally, a heartfelt thanks to the indefatigable @Mili10 , who has made my life easier and more productive for a decade. My sincerest thanks. Many more of you deserve a thank you, I’ll ping you directly. What’s ahead? I will be an active advisor for the next 6 months. We all want to make sure the change is smooth, in particular for the folks in our network who have a long-standing relationship. After that, I will not be gone and dead, haha. While I’ll take a nice break, I’ll also be looking for what to build next. My number won’t change. So feel free to reach out if you need anything. The house is built. I will forever bleed a16z. Here’s to more building!

How about supportive family-friendly policies like national maternity leave, universal TK, and affordable and accessible childcare? nytimes.com/2025/04/21/us/…

@MikeIsaac Horrifying

alternate headline: facebook board member hangs out with alleged human traffickers

Never felt more grateful for the Commonwealth.

@parkerconrad Saw this happen with a client who owned a huge chunk of SMB online invoicing market, until Xero came along, raised $100m+, and went on to not only eat their lunch but build a new market with their sales team. No coming back from that despite the massive head start.

The way this will play out is a competitor will raise a ton of financing, invest more deeply in R&D, build a better product, and absolutely crush this guy with sales and marketing. You have to play the game on the field.

4yo at 2am: I'm scared, can I sleep in your bed? Me: Sure. 4yo for the rest of the night:

I hope Snoop Dogg's deal included a kicker that gets him comp'd commensurate with insane amount of value he created for NBC.

@MikeIsaac I'm shocked they served it at 9am. I've gotten dead eye stares when I've tried to order before 2pm.

committing another crime of afternoon tea at nine am

@alirayl @bumble Congrats! A great collaboration ahead.

So proud of his skill, humor and empathy. What a wonderful and wild ride!

Proud supporter of the work of @19thnews, abortion access is a winning issue.

@CeciStalls I just had tomato toast for lunch, and the same for breakfast.

To👏ma👏to👏toast👏

@johnnyrodgersis @aweissman I didn't even have the chance, he's already got them on order after a text from @ph this morning 😂

@aweissman @Rsquared this is what you buy the man who has everything

Blue Bottle x New Balance collab

@merci Agreed Rage-giving reco: thenext50.us

In moments like this, it's felt particularly productive to donate to @theNext50US which is building up the next gen of young Democrats thenext50.us nytimes.com/2023/07/27/us/…

How on earth does "it's summer in San Francisco" make into a story about a 7:30pm shootout in a playground where parents are laying on top of their children? I was here w/ my kids the day before. Shots fired in drive-by shootout at Precita Park in Bernal missionlocal.org/2023/06/shots-…

@timoni I couldn't get past episode 2 of the last season, I think the squicky cuteness is what we needed circa 2020/21, but !not landing the same way now.

Did anyone else *not* like Ted Lasso S03—especially the ending? It was a GoT S08 for me, but everyone else seems to have loved it. I need a safe space to be sad 🥺