November 29, 2022

Bolt’s Ryan Breslow has boosted the value of his fintech to the moon by promising an Amazon-style checkout to millions of online retailers. Now the newly minted billionaire is making a lot of noise—and powerful critics—challenging the tech industry’s culture. With an $11 billion valuation in the face of widespread skepticism, Breslow is determined to prove that Bolt is more than just a flash in the pan, and that he’s more than just a lightning rod.


Away from South Beach’s pulsing pool parties and the tycoon enclaves dotting Biscayne Bay, Ryan Breslow, one of Miami’s richest residents—and, at 27, one of the world’s youngest billionaires—balances cross-legged atop a blue beanbag pillow in his humble three-bedroom bungalow right on the border of Little Haiti.

Breslow spends most days alone at home. He dances to “house disco” music on the AstroTurf in his backyard. He meditates amid soaring palm trees, white Buddha statues and a humming air conditioner. And, from a treadmill desk in his sunroom, near the ceremonial drums, he runs Bolt—his $11 billion (valuation), 700-employee fintech startup that’s out to provide millions of online shops with frictionless one-click checkout à la Amazon.

“I live a monk lifestyle. It’s amazing what you can get done if you remove distractions,” says Breslow, who is dressed like a confetti cannon: T-shirt printed with a purple cartoon Bolt superhero, rainbow-splattered running shorts, psychedelic Nikes with glitter soles.

Between Zoom meetings and virtual yoga sessions, Breslow, whose stake in Bolt gives him a fortune worth $2 billion, eats a vegan, locally sourced lunch in solitude and silence. He rarely eats in front of other people. He abstains from meat and gluten, caffeine and alcohol. No supplements or illicit substances, either. The strict routine is part of what he calls “working like a lion,” a philosophy of executing in brief bursts of hyperfocus and intensity, similar to how the big cat hunts. “There’s too much work theater, where people go through the motions to appear busy,” says Breslow, who recently instituted a four-day workweek at Bolt. “I’d much rather have you focus on your health, well-being and family during your time off, so that when you’re here working, you’re all in.”

After sunset, he avoids electric lights and screens because they disrupt his sleep. Instead, he lights candles and plays a buffalo-skin drum (he made it himself with the help of a local indigenous tribe) to wind down before bed.

“Most people who get rich want to be a part of an elite circle. I want nothing to do with it—I’m probably one of the only billionaires who has that feeling,” Breslow says with a smirk. “I don’t want to be in their clubs, their groups, their parties.”

For a cloistered homebody who claims to disdain the Silicon Valley scene, Breslow seems to be everywhere in tech these days. In all he has raised $1 billion from venture capitalists, $873 million of it just since 2020 from blue-chip shops like General Atlantic, BlackRock, WestCap and H.I.G. Growth. He has turbocharged Bolt’s valuation to $11 billion—a figure that has many in the investment world scratching their head, given that the company did just $40 million in 2021 sales. The number of shoppers who use Bolt’s software has exploded, from 800,000 at the start of 2020 to more than 12 million today. Breslow has signed deals with Adobe, Forever 21 and Fanatics. Insiders say Bolt has soon-to-be-announced deals with a major social network and one of America’s largest department stores. Outside the company, Breslow has self-published two books (Fundraising and Recruiting) and launched two nonprofits: Conscious.org spreads his “work like a lion” gospel, and Movement offers free dance classes in Miami, Los Angeles and New York.

He has also caused industry-wide confusion and controversy. In January, he stepped down as Bolt’s CEO to become its executive chairman, an extremely unexpected move for a young entrepreneur who had just closed a $355 million funding round. He’s publicly touting a controversial employee stock option loan plan that he calls radical but battle-scarred veterans of Web 1.0 say is just reckless. And he has recently taken to Twitter to throw 280-character haymakers at some of Silicon Valley’s biggest players.

“I’m not afraid of bothering a few powerful people. If I’m not going to speak up about the darkness that I see in Silicon Valley, who is?” 

In January, Breslow tweeted a multithread screed arguing that Stripe, the $95 billion (valu­ation) payment darling, and Y Combinator, the elite startup accelerator, are “mob bosses” that collude to crush fintech competition. It was both business and personal for him. Stripe is a competitor. Y Combinator had rejected him. In February, he wrote that Shopify, the $90 billion e-commerce company that offers high-tech tools to small businesses, eats its own ecosystem by stealing its developer community’s best ideas. Neither Stripe nor Shopify—nor Patrick Collison nor Tobias Lütke, their respective billionaire CEOs—has responded publicly to his provocations.

“I’m not afraid of bothering a few powerful people. If I’m not going to speak up about the darkness that I see in Silicon Valley, who is?” Breslow says. “I believe you should share the knowledge and also share the struggles, because the thing I hate most about Silicon Valley is everyone’s telling a Cinderella story.”

Of course, sharing the struggles makes for good marketing too. Bolt, a wonky digital checkout startup that’s far from a household name, needs to sign up millions of users, fast. A well-timed Twitter beef with well-known competitors is a cheap way to draw attention and build hype.

Breslow says his tweetstorms are far from late-night Trumpian rants. Before posting, he meditates on the thesis and asks his leadership—now made up of seasoned operators from Amazon, Twitter and Pinterest—for feedback. Managers, investors and customers say they’re okay with his outspoken style.

“That’s Ryan. He’s a Gen Z entrepreneur unsatisfied with the order of the world, and he wants to change it,” says Bolt CEO Maju Kuruvilla, a former Amazon exec who managed global logistics and Prime fulfillment. “Most people who achieve success don’t upset the apple cart. Ryan is more fearless.”

BigCommerce CEO Brent Bellm, a Bolt client whose software powers more than 60,000 online stores, is a big fan: “I love it when people use their free speech to say something provocative and interesting, rather than bland or politically correct. It’s fantastic.”

Bolt’s promise is simple: to eventually give millions of merchants, and hundreds of millions of shoppers, seamless one-click digital checkout. Amazon has had it for years. Ditto Shopify. So why not the regional grocery store, midsized retailer or auto shop chain? Bolt is targeting this enormous middle ground.

“They are in a very big market and have very big opportunities. In five to ten years, they could power 20% of the retail market,” says Dennis Cong, the founder of CE Innovation Capital, who invested in Bolt’s Series E round. In 2021, Amazon sold about $600 billion worth of goods. Shopify’s network of more than 1 million stores moved $175 billion. Bolt is going after the rest of the world’s merchants, who, per Statista, sold around $4.9 trillion worth of stuff online in 2021.

For a buyer, Bolt puts an end to filling out forms, hunting down credit card numbers and remembering yet another password. You can join its shopping network by simply checking a box when you check out at a partner store. Then, each time you visit a Bolt-powered site, you’re recognized and can log in and make a purchase with a single click and code sent via text message or email.

For sellers, the reduced friction of one-click checkout means more sales, more often. Today up to 70% of items get stran­ded in online checkout carts. Bolt gets paid only when there is a sale, taking about 2% of each transaction. That’s roughly the same that Shopify charges for customers that don’t use its internal payments software. Amazon handles everything but hits its third-party sellers with hefty fees that range from 8% to 45% of the retail price. Bolt merchants are responsible for paying their own shipping and credit card fees.

On the surface, checkout is boring and simple, but the technology and regulatory challenges are tough. Each retailer’s site must handle payments, sales taxes, inventory, shipping costs, delivery addresses and coupon codes, all while watching eagle-eyed for fraud. “I had to build 30 integrations before I could stand up one checkout. The software’s very hairy; a lot of the commerce ecosystems are hacked together,” Breslow says. “That’s why checkout on most sites looks like it was built ten years prior to the rest of the site. And we had to do something that’s much harder: build a general framework that could be installed anywhere.”

Peter Krukovsky, Moody’s senior analyst for financial technology, says competitors in the crowded space must offer more than speed to win customers. Amazon has scale, dependability and free delivery. PayPal, the granddaddy of online payment processors, which is accepted by 80% of the biggest 500 sites in the U.S., offers fraud protection, peer-to-peer payments and debit cards. Apple Pay, preinstalled in more than 110 million iPhones in America alone, works equally well in the App Store and your local coffee shop. Fintech companies Affirm, Afterpay and Klarna give users instant loans. Even garden-variety web browsers autofill shipping addresses and credit card numbers for easy checkout.

Many mighty efforts have failed. Visa, Chase, American Express, Google, Samsung and Walmart have all launched “buy now” buttons only to see them stall. Even Amazon, the OG of one-click shopping, slowed its campaign to get its yellow buy button affixed on outside sites. “It’s a big graveyard,” says Lisa Ellis, senior managing director at research shop Moffett­Nathanson. “Dozens of companies have gained traction, hit 10% penetration of merchants, and then they die because they never get enough customers.”

Breslow believes Bolt can cheat death—and justify its bubblicious $11 billion valuation—by going beyond the buy button. Let other companies battle over whose button has the best real estate on a site. Bolt wants to work as a bridge, powering transactions behind the scenes. Think “Intel Inside” for retail. In the tribal world of fintech this could be a real differentiator. Bolt wants to be Switzerland. Its middleware works with any payment processor, coding language and purchase method—credit and debit cards, Apple Pay, Google Pay, PayPal, buy-now-pay-later firms and, soon, crypto. With no ties to any credit card, bank, telecom, social media giant or commerce brand, Bolt can work with everyone.

Investors are looking past its paltry $40 million in annual sales partly because it takes months for new, large retailer partners, which Breslow is signing in droves, to go live on the network. They expect both revenue and users to surge in the second half of 2022. “We look for a mix of an amazing founder and team, correct thematics, product traction and very strong customer adoption. Bolt has all of these,” says Lion­Tree investor Howard Han. “Enterprise deals have a backlog from when you sign and onboard a customer. We’re looking at the pipeline more than anything—who’s using the product, the types of businesses they’re winning.”

It’s the potential scale that has backers piling in at decacorn prices. “Yes, valuations have gone bananas for everyone over the last 12 months,” says one of Bolt’s Series D investors. “But Bolt is signing deals with merchants who can deliver $100 million worth of gross transactions a year. For us that’s the main driver.”

It was on a driving range, rather than in a computer lab, where Bres­low started down the path that would lead to billions. He grew up in North Miami Beach in a family of energetic small-business owners. His grandfathers had run a jeans shop, a small accounting firm and a seafood market. His parents’ business: Aqua Golf, a beloved local range where hackers could splash balls into a lake. (It briefly became a tourist attraction in the late 1990s after the Farrelly brothers featured it in There’s Something About Mary.) Breslow spent his youth cleaning clubs, helming the cash register and snagging balls with a fishing net. “I’d be 13 years old and running the entire shop,” he says. “At a young age my dad taught me the value of a dollar.”

He attended Dr. Michael Krop Senior High, a 2,500-student public school where more than half the kids lived below the poverty line. He studied hard, taking as many AP classes as he could while earning additional credits online. He taught himself how to program using online tutorials and YouTube. He launched an online mattress company called Memory Foam Doctor and built websites for Bal Harbour, a luxury shopping center, and UNKNWN, a LeBron James–backed streetwear brand. “I was making around $1,000 a project, so I wasn’t raking it in, but definitely making more than any of my friends.”

“It felt like the universe had a plan. I said ‘screw it’ and dropped out of Stanford to build the company alone.” 

Good grades and entrepreneurial hustle won him admission to Stanford in 2012. Palo Alto was a culture shock. The driving-range cashier was now classmates with the country club set. “I had never met kids with this level of wealth. People’s parents had founded companies and were CEOs of corporations,” he says. “Parents had them in programming classes since they were 12.”

If he was intimidated, he didn’t let it show. He studied computer science, got into breakdancing, relaunched the Stanford chapter of Alpha Epsilon Pi (a Jewish fraternity focused on entrepreneurship) and cofounded the Stanford bitcoin club. Sophomore year he and a classmate began designing a digital wallet that let you buy small amounts of bitcoin to use for everyday commerce. A Silicon Valley tech vet pledged seed capital, and the two got to work.

Soon, though, his cofounder lost interest and their backer bailed. At the same time Breslow’s grandfather, whom he considered his best friend, died and his mother was diagnosed with cancer.

“It felt like the universe had a plan. I said ‘screw it’ and dropped out of Stanford to build the company alone.”

He was no longer in school, but he made a copy of his room key and kept living in his dorm. That semester, Stanford friend Eric Feldman joined as a cofounder. Then, in February 2014, a classmate, Armaan Ali, who now runs the VC firm Human Capital, wrote a small seed check. Tech entrepreneur and Stanford lecturer Jay Borenstein wrote a bigger one, and Breslow got an apartment.

He and Feldman spent a year learning about financial regu­lations, compliance, money laundering rules and fraud prevention. But there was a bigger problem: Bitcoin was horrible for day-to-day purchases. Transactions were slow, fees high and no retailer wanted to accept a currency that could lose half its value overnight. They needed to pivot fast. “One day it hit me like a bolt of lightning. Amazon has offered one-click checkout since 1999 and the rest of the world doesn’t,” he says. “The more I learned, the more I realized how big it could be.”

He still has a lot of persuading to do. His Twitter feed is full of angry missives from grizzled tech execs and grumpy VCs who hate his critiques of Silicon Valley, how he pays employees and Bolt’s surging valuation. Breslow doesn’t care. He continues to needle Stripe and Shopify and is standing his ground on Bolt’s new option loan program, through which, as part of their compensation, he lends employees cash to buy Bolt stock options.

Breslow has called the policy “a breakthrough” and “the most employee-friendly option program possible.” Problem is, it’s not a new idea—and it’s not necessarily a good one. The practice of companies lending employees money to purchase stock options as a way of juicing their pay was common in the 1990s and ended in disaster. When the first tech bubble burst, the options were worthless, people’s jobs evaporated . . . and then the loans came due.

Breslow isn’t afraid to let exaggeration, or sometimes the truth, get in the way of a good story. In February, he boasted to Forbes that he’s an outsider who’s never taken a penny from Sand Hill Road, shorthand for Silicon Valley venture capital. Yet his investor roster includes Bay Area firms Tribe Capital, Soma Capital, Ridge Ventures and Sand Hill Angels. One former Bolt employee says that in the early days, some of the sales team inflated revenue and transaction value to pad their commissions. Breslow owns up to it. “Some salespeople, and some merchants, inflated numbers. We put it to bed super-quick, ending self-reporting and creating an audit committee to go over data and figures. We never misrepresented numbers to shareholders or during fundraising.”

In truth, Breslow is following a well-worn playbook in a fake-it-till-you-make-it industry full of outrageous claims, far-out philosophies, quirky routines and cults of personality. After all, this is the industry responsible for biohacking, microdosing, polyamorous relationships and Burning Man. Compared to many of his peers, he’s positively straight-edge.

With his new CEO running Bolt’s daily operations, Breslow can focus on closing big deals. Sources say he’s currently raising more capital at a $14 billion valuation. He’s also recruiting star coders and, yes, making more noise. He certainly has no plans to quiet down. “If you’re turned off by me speaking my truth, well, guess what? More of that’s going to happen—you probably shouldn’t be investing in me.”

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https://www.forbes.com/sites/stevenbertoni/2022/04/04/meet-the-gen-z-billionaire-whos-speaking-his-truth-to-silicon-valley/