This Isn’t Philanthropy A Letter to Anand Giridharadas Dear Anand, You wrote the book on why billionaire philanthropy fails — how “changing the world” became a cover for protecting the systems that create the problems philanthropy claims to solve. How the people who benefit most from inequality get to decide how to address it, and unsurprisingly decide on solutions that don’t threaten their position. I read Winners Take All. I’m not writing to argue with it. I’m writing because I built something that tries to route around the whole problem. ...

What If the Infrastructure Gave Automatically? An Open Letter to Bill Gates Dear Mr. Gates, You’ve committed $200 billion over the next 20 years. You’ve said the Gates Foundation will close in 2045. You’ve decided to spend down rather than exist in perpetuity. I want to ask you a question: What happens after 2045? The Giving Pledge Problem The Giving Pledge has enrolled 256 signatories. Reports suggest many haven’t followed through. The critique is structural: pledges depend on individual decisions, individual timelines, individual priorities. When the billionaire dies or changes course, the giving stops. ...

Craigslist for Everything Else A Letter to Craig Newmark Dear Mr. Newmark, You accidentally killed the newspaper classified business and then spent years funding journalism to make up for it. That’s either guilt or integrity — probably both. Either way, it means you understand that building something useful can break something necessary, and that the builder has a responsibility to notice. I’m a veteran. I know you’ve put significant resources into veteran causes. I also know you’ve funded civic tech, journalism, and trustworthy information infrastructure. So I’m writing to you about something that touches all three. ...

What If the Infrastructure Gave Automatically? An Open Letter to Bill Gates Dear Mr. Gates, You’ve committed $200 billion over the next 20 years. You’ve said the Gates Foundation will close in 2045. You’ve decided to spend down rather than exist in perpetuity. I want to ask you a question: What happens after 2045? The Giving Pledge Problem The Giving Pledge has enrolled 256 signatories. Reports suggest many haven’t followed through. The critique is structural: pledges depend on individual decisions, individual timelines, individual priorities. When the billionaire dies or changes course, the giving stops. ...

A Business Model, Not a Charity An Open Letter to Warren Buffett Dear Mr. Buffett, You’ve said you’re “going quiet.” But you also said you’re not going to sit at home and watch soap operas. This isn’t a pitch for money. It’s a pitch for scrutiny — from someone who’s spent 60 years understanding what makes businesses work. The Model Liana Banyan is a cooperative commerce platform with a fixed margin: Cost + 20%. ...

MacKenzie Scott Letter — VERSION 02 (Updated) Dear Ms. Scott, I don’t want your money. I’m asking for something far more valuable: your guidance on who should run six ready-to-launch initiatives that transform how communities provide for each other, and the platform that enables, and from now on sustainably funds, those initiatives. In college, at one time I had two roommates. One was wealthy—his family literally owned ten homes. The other was poor like me. When I needed a suit and couldn’t afford one, my poor roommate immediately gave me one of the two he owned. Only then did my wealthy roommate offer one of his fifteen. That sacrifice thirty years ago still makes me cry, and it exemplifies the truth you wrote about which gift means more—$100 from someone earning $50,000 or $100,000 from someone with millions. ...

What Comes After the Foundation A Letter to Melinda French Gates Dear Ms. French Gates, You spent decades building one of the largest philanthropic organizations in history. Then you left, started Pivotal Ventures, and began doing things differently — faster, more focused, less institutional. I’m writing because you’ve seen what works and what doesn’t at scale. And because the thing I’ve built needs someone who understands that helping women often means helping everyone, and that infrastructure beats charity every time. ...

A Business Model, Not a Charity An Open Letter to Warren Buffett Dear Mr. Buffett, You’ve said you’re “going quiet.” But you also said you’re not going to sit at home and watch soap operas. This isn’t a pitch for money. It’s a pitch for scrutiny — from someone who’s spent 60 years understanding what makes businesses work. The Model Liana Banyan is a cooperative commerce platform with a fixed margin: Cost + 20%. ...