Rebecca Reeve Henderson

Founder/CEO of Rsquared Communication, scaling industry-leading B2B SaaS companies. Advisor and investor.

[Aakash Gupta @aakashgupta]

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.

[Rebecca Reeve Henderson @Rsquared]

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

[Rebecca Reeve Henderson @Rsquared]

America First? Not When It Comes to Your Health. https://t.co/ARgKyZ26zX via @NYTOpinion

[Rebecca Reeve Henderson @Rsquared]

@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!

[Rebecca Reeve Henderson @Rsquared]

How about supportive family-friendly policies like national maternity leave, universal TK, and affordable and accessible childcare?
https://t.co/qrT9fBNiwl

[Rebecca Reeve Henderson @Rsquared]

@MikeIsaac Horrifying

[Rebecca Reeve Henderson @Rsquared]

Never felt more grateful for the Commonwealth.

[Rebecca Reeve Henderson @Rsquared]

@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.

[Adam Morris @adamwm89]

4yo at 2am: I'm scared, can I sleep in your bed?

Me: Sure.

4yo for the rest of the night:

[Rebecca Reeve Henderson @Rsquared]

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

[Brian Stelter @brianstelter]

The Summer Olympics have been a huge success for NBC. Ratings are way up. Revenues, too. I spoke with several NBC Sports and Peacock execs about what they've observed and learned 🧵

[Rebecca Reeve Henderson @Rsquared]

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

[Rebecca Reeve Henderson @Rsquared]

@alirayl @bumble Congrats! A great collaboration ahead.

[Rebecca Reeve Henderson @Rsquared]

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

[Cal Henderson @iamcal]

Happy 10th birthday to Slack 🎉
Happy 20th birthday to Flickr 🎉

Time for me to take a little break 😅

[Rebecca Reeve Henderson @Rsquared]

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

[Emily Ramshaw @eramshaw]

.@19thnews and its impact, in one short story:

1. @shefalil reports and writes a story about an Arizona Supreme Court justice who openly opposes abortion being on the bench to decide its legality in the state anyway.

https://t.co/uWRiph70Vt

[Rebecca Reeve Henderson @Rsquared]

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

[Rebecca Reeve Henderson @Rsquared]

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

[Rebecca Reeve Henderson @Rsquared]

@merci Agreed

Rage-giving reco: https://t.co/6W6VHhjgx1

[Rebecca Reeve Henderson @Rsquared]

In moments like this, it's felt particularly productive to donate to @theNext50US which is building up the next gen of young Democrats https://t.co/6W6VHhjgx1

https://t.co/iWsxQ8Zre2

[Rebecca Reeve Henderson @Rsquared]

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 https://t.co/Fad5dUelP9

[Rebecca Reeve Henderson @Rsquared]

@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.