The Gates Girls & The Ceiling of Inherited Advantages
Phoebe's cookie-stuffing scandal and Jennifer's wasted Olympic horse tell the same story about what money can't manufacture.
You know who Bill Gates is, right? Microsoft co-founder, the world’s richest man for several years running, associate of Jeffrey Epstein? Yeah, good.
Well, Bill Gates has two daughters: Jennifer and Phoebe.
Phoebe Gates, the younger daughter, has been in the headlines recently. She co-founded an AI shopping app called Phia with her Stanford roommate Sophia Kianni in 2025. It functions as a browser extension and phone app, price-checks items as a user shops, and then sources cheaper new or secondhand versions from across the web. It’s marketed as “Google Flights, but for fashion.” The startup built a star-studded cap table. Backers include Hailey Bieber, Khloé Kardashian, Sheryl Sandberg, Sara Blakely, Alix Earle and Tyra Banks. Currently, Phia has raised roughly $43 million.
This past week, Phia was accused of “cookie stuffing”. What that means is it’s overriding other affiliates’ referral codes to claim commissions for sales it did not drive. The scheme led to the app's suspension from the affiliate platform Impact.com. Phia addressed the issue promptly, saying it was a bug, not fraud, and that the issue has been fixed. And that may very well be the case, but you know the internet: worst-case scenario is the presiding fact. Also, I feel like the media was harsher about this than they are toward AI companies that steal people’s work and don't compensate them. Such is the life of women in…well, anything, really.
So, I will give Phoebe that; the scrutiny and response to this seemed disproportionate to what men in tech have done. I don’t remember people being this vocal when Mark Zuckerberg and Facebook were accused of fueling a genocide in Myanmar. Elon Musk ordered employees back to work in defiance of a stay-at-home order meant to stop the spread of a pandemic. Don’t get me started on Peter Thiel.
The thing is, though, why did this happen? I don’t really know much about tech and software engineering, but I would assume that a daughter of Bill Gates will be paired with top engineers and project managers. Maybe there’s an employee with something to gain, either way it’s certainly not a good look. How can someone with the right connections and wealth botch running an app? And, thinking about that, I realized this is not the first time Bill Gates has had a daughter completely miss the landing on an opportunity served on a gold platter.
Bill’s other daughter is Jennifer “Jenn” Gates. She the eldest. Jenn is now married, has two children, and is a doctor, specifically a pediatric resident. However, she used to be an avid competitor in the equestrian sport of show jumping. The thing to know right away: Jenn was competing at the level where most horses cost upper six figures and into the millions. Expensive.
Like most riders, we can assume she wanted to rise to the top of the sport and go to the Olympics. So her dad got her the best horses. And then he got her thee best horse: Darry Lou.
Darry Lou was being ridden by Beezie Madden at the time and having tremendous success. He and Beezie were slated to compete in individual and team show jumping at the 2020 Tokyo Olympics. Unfortunately, COVID delayed the games by one year. Safe assumption that the sale agreement for Darry Lou specified that transfer of ownership would occure after the original 2020 Olympic date.
Did Jennifer acquiesce to let Beezie ride for another year to give Team USA the best chance at gold? No, she did not. She took over the ride soon after the games were canceled and proceeded to do nothing. Jenn never got this horse to a podium, IIRC, and, again, this was the best horse money could buy at the time.
Eventually Jenn gave up and let her husband, Nayel Nassar, have the ride. If you’re not into horses, quick summary: Nayel rides for Egypt and is top-ranked (#60 at time of this writing). So like he’s good, and he did have some success but never was able to get Darry Lou to the Olympics as Beezie nearly had. Darry Lou retired to stud in 2024.
Honestly, I do think his legacy was marred by the sale to Jennifer Gates. Also, it’s very reasonable to say that the US Olympic team very likely lost a medal. And for what? Jennifer is a good rider but she’s never been close enough for Olympic consideration. She also wasn’t riding well enough at the time to warrant the jump to Darry Lou. I guess she thought maybe she would grow as a rider with him but I think their partnership exposed that she has hit the ceiling of her riding capabilities.
Jenn is good but not the best and, turns out, not Olympic caliber. It’s tough but that’s life and that’s most people. For what it’s worth, I am also not an Olympic caliber rider. It’s just kind of unfortunate that bigger stakes and a top horse’s prime were wasted so a rich girl could come to terms with the limitations of her riding ability.
So, it turns out money really can only take you so far. You can buy the best horse in the world, but Beezie Madden’s talent doesn’t come with the bill of sale. You can staff a startup with a billionaire dad, and it still won’t stop you from (allegedly) getting caught cookie-stuffing your way to commissions you didn’t earn. Both Gates daughters had the same resource: a seemingly inexhaustible supply of their father’s money. And both ran into the same wall: the job asked for something a check can’t buy, and neither of them had it. You can inherit the cap table, the connections, and the horse. You can’t inherit the part that actually makes it work.
But, you know what, at the end of the day I commend them both for getting degrees and working. I don’t even blame either of them for using the opportunities afforded to them. This article merely serves as a reminder that life is hard, and so is success - even with every possible advantage. So be easy on yourself if your own journey isn’t turning out how you’d hoped.
Anyway.
Live, laugh, love, spend your dad’s money,
Jay