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Chris Comparato, CEO, the Toast, Inc. IPO at the New York Stock Exchange, on September 22, 2021.
Source: NYSE

Not long after selling software company Endeca to Oracle in 2011 for over $1 billion, Steve Papa called Bessemer Venture Partners with a hot tip. He said three of his best engineers were working on something new that Bessemer, which had previously backed Endeca, would be crazy not to fund.

Kent Bennett, who’d been a junior associate on the Endeca deal, fielded the call. He told Papa there was some empty space at the firm’s office in Boston that his people could use. But Bennett knew he couldn’t get his firm, one of the biggest and most successful in the venture industry, to write a check to three engineers with an unspecified project.

“I said, ‘Well just send them over here and they can hang out here until they figure it out,'” Bennett told CNBC, recalling his conversation with Papa.

The three guys and some office space eventually became Toast, a provider of software and hardware to restaurants that held its New York Stock Exchange debut on Wednesday, closing the day with a market cap of over $31 billion. (It’s since slipped to $28 billion.) The three co-founders — Steve Fredette, Aman Narang and Jonathan Grimm — are billionaires, and remain top executives at the company.

Fredette, Narang and Grimm now have about 2,200 co-workers. They call them Toasters.

Bessemer eventually ended up investing in Toast in 2015, and Bennett joined the board. But even though it’s one of the largest holders, with over a 12% stake, the returns would’ve been much larger had Bessemer jumped in earlier.

Bennett told one of his partners he’d made a “massive mistake” by passing. It wasn’t just Bessemer. Venture capitalists wanted nothing to do with the restaurant industry, where margins are low and budgets notoriously tight.

So in early 2013, Papa filled the initial void by investing $500,000 of his own money into his buddies’ start-up.

“I said, ‘guys it’s not my space, but you helped me be successful, and I owe it to you,'” Papa, who was on the Toast board until recently, said in an interview after the IPO. “I was going to help them no matter what. In this case it meant capital to get them going. Did we understand the shape of it at that time? No.”

Papa’s investment today can be measured in billions. As of Friday’s close, his 12% stake in Toast is worth $3.1 billion, amassed from the initial investment and follow-on funding. He controls slightly less than Bessemer, which owns $3.3 billion in Toast shares after investing just over $100 million between 2015 and early 2020.

No ‘West Coast offense’

Start-up origin stories are part of the fabric of the tech industry. Apple and Google famously started in Silicon Valley garages, Facebook was built by a boy-wonder Harvard dropout, and PayPal came together through an awkward collaboration between Elon Musk and Peter Thiel and included an exhaustive list of engineers who would go on to build other billion-dollar companies.

Increasingly, Silicon Valley stories have become more formulaic, thanks to programs such as Y Combinator, which has turned into a Unicorn factory over the past decade. The start-up incubator has helped spawn Dropbox, Airbnb, Stripe, DoorDash, Coinbase and Instacart, and serves as a direct path to meetings with the top venture capitalist firms.

Toast was born on the other side of the country and a world away. The founders lived in the Boston area and had no plans to leave. Boston had been a venture hub in an earlier era, but the momentum had shifted to Silicon Valley, where all the big exits were taking place. Bessemer has offices in both locations.

Papa said one Bay Area VC indicated interest in the pitch for Toast, but said he didn’t want to get on a plane.

Fredette, Toast’s president, said the company’s East Coast roots ultimately became an advantage because it could be “a little unconstrained by the traditional wisdom of grow, grow, grow.”

“We used to talk about West Coast offense, which was hype over substance,” Fredette said in an interview from the NYSE on Wednesday. “East Coast would be substance first and not enough hype.”

The founders sprinkled in a healthy dose of naivete. Fredette said they were so inexperienced with fundraising and business in general that he and Narang, the chief operating officer, would often debate each other during investor meetings.

The original idea for Toast came from all the hours Fredette, Narang and Grimm spent hanging out in Boston bars, cafes and restaurants trying to figure out what to build. After experiencing a particularly long wait time for the check one day, they thought they’d found a problem that could be fixed by paying the check from their smartphone — if only the technology existed.

They developed an app and launched it in 2012 with Firebrand Saints, a bar they frequented in Cambridge. The app gave customers a way to start a tab at the restaurant and link a credit card.

“We used to go there a lot after work to get a burger and a beer,” Fredette said.

As they slowly expanded in the region, they signed up Dwelltime, a cafe in Cambridge.

That’s where Bennett got to demo the product. The transaction went through. Still, Bennett was terrified of putting money into a company that was trying to take on incumbent point-of-sale (POS) vendors like Micros, which Oracle bought in 2014 for $5.3 billion, and NCR.

“To me it sounded like a suicide mission,” said Bennett, recalling that he told the founders it would take them five years to build something viable. “These legacy systems were old and painful but they were 50,000 features into a really complex roadmap.”

Meanwhile, Papa would soon start flying around the country trying to help land new business deals and recruit talent.

One place he wasn’t going: The Bay Area.

“We intentionally chose not to put reps in Silicon Valley,” Papa said. As long as potential competitors didn’t see the product in action, they could continue “arrogantly dismissing it,” he said.

Instead, Papa was traveling to places like Grand Rapids, Michigan, home to a 124-year old company called Gordon Food Service. Gordon distributed food to restaurants across the country and became a critical distribution partner for Toast.

“We focused on the middle of the country, which was mostly overlooked,” Papa said.

Toast quickly evolved from a relatively simple mobile app at Firebrand Saints and a few other spots to a more complete back-end restaurant system that used Android tablets as terminals. At the time, iPads were the far superior product, and were being used by buzzy start-ups like Revel Systems.

Toast opted for Google’s open source Android technology, which allowed the company to design its own hardware and customize software rather than being restricted to Apple’s closed system.

Toast point of sale system
Toast

By late 2015, Toast was up to 170 employees, had millions of dollars in revenue and was used in thousands of restaurants, including Costa Vida, a Mexican-themed chain with 75 locations, and Beach Hut Deli, which had 40 locations on the West Coast. Chris Comparato, another Endeca alum, had just joined as CEO.

That’s when Bessemer finally took the plunge, leading a $30 million round along with Google’s venture arm at a valuation of about $100 million. Bennett said the big move that changed his thinking was Toast’s push into payments. As a full POS vendor that was getting a cut of every transaction on the system, Toast at last had a volume business with a consistent and profitable revenue stream.

They used margin from payment processing to support software development, Bennett said, and the business model clearly worked. In a memo to the firm in December 2015, Bennett wrote that “we’ve stood by anxiously as the team hit obvious product-market fit but punted on raising more equity.” 

To get onto the cap table, Bennett was having monthly dinners with the founders trying to convince them to take Bessemer’s money. He also recalled telling Felda Hardymon, his mentor at the firm, “I think this will be the biggest business Boston has ever seen.'”

Papa was making similar pronouncements as he tried luring investors. In a June 2015 presentation, he wrote in one slide that Toast had “the potential to be the next Uber or Airbnb valued in the many billions” and that it had “potential to build $10b+ exit.”

“In fairness to VCs, a lot of people put stuff like that on slides,” Papa said. “We have survivorship bias.”

Toast in 2015
Steve Papa

Bessemer was very bullish, but it never predicted Toast would be worth this much. In Bennett’s memo, he laid out potential outcomes and how much the firm would receive in each case. The off-the-charts “just goes nuts” scenario would produce an $8.3 billion company and a $700 million return for Bessemer.

‘Oh my god, we’re going to lose it’

Toast’s growth trajectory over the next four-plus years was so dramatic that in February 2020, the company raised $400 million at a $5 billion valuation. Annual revenue had swelled to $665 million, mostly from payment transaction fees. Toast was helped by a 10-year bull market in the tech industry, featuring astronomical valuations for companies across the board.

A month after that mega-financing round, it almost all came crashing down.

The Covid-19 pandemic immediately exposed Toast’s glaring risk: Reliance on a single industry. As infections spread rapidly, restaurants across the country saw revenue plunge 80% in March, squashing Toast’s business.

Cash quickly dwindled and Toast was force to slash about 50% of its workforce in April, eliminating roughly 1,300 jobs.

“With limited visibility into how quickly the industry may recover, and facing slower than anticipated growth, we now find ourselves in the unenviable position of reducing our headcount,” Comparato wrote in a blog post announcing the job cuts.

At the board level, panic set in.

“Immediately we said we’re burning a ton of capital and are going to go out of business if we don’t do something now,” Bennett said. “I remember everyday going by thinking, ‘oh my god, we’re going to lose it.'”

Even more shocking was the speed of the rebound.

Restaurants reopened their doors to takeout and outdoor dining, and brought in a bunch of new technology to enable contactless ordering and mobile payments.

Toast’s POS system had expanded to include inventory management, payroll, and multi-location menu controls, which were all useful in simplifying a manager’s job. But what restaurants really needed was a takeout app that synced with their existing system and a way for diners and wait staff to limit contact.

So they turned to Toast for newer products like curbside notifications for takeout, flat-fee deliveries, and mobile software that enabled ordering and payments from their devices.

By the third quarter, revenue was increasing again from the prior year. And for all of 2020, sales jumped more than 20% to $823.1 million. Headcount is back near pre-Covid levels.

Bennett said that during the pandemic Toast became a consumer brand. He knows because his friends started telling him about their experience at restaurants using mobile payments with the Toast logo.

Toast mobile payments
Toast

“I probably got three-dozen texts this year from friends who were like, ‘this is the piece of bread from your t-shirts,'” Bennett said.

It’s the exact idea that inspired the founders eight years earlier, long before the technology existed to make it work. Narang said on Wednesday that, “we were just too early” and the company has come “full circle.”

Even Bennett has been surprised by how many restaurants now use it.

After a recent meal at Pammy’s in Cambridge, Bennett was waiting a while for the check to arrive. After eventually paying by card, he noticed the QR code on the receipt. Had he scanned it, the Toast payment option would have popped up on his phone.

“It would’ve gotten me out of there a lot sooner,” he said.

Papa is also hearing from friends, including those who could never have imagined that the restaurant-tech start-up he seeded almost a decade ago would be worth close to $30 billion.

“I remember you telling me exactly how this would all play out over lunch one day in Kendall Square,” a friend emailed him on Thursday. “But I don’t remember you mentioning the part about the pandemic. Anyways, quite the success story.” 

WATCH: Toast and AKA Brands make their NYSE debut

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Astronomer CEO Andy Byron resigns after viral Coldplay kiss-cam controversy

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Astronomer CEO Andy Byron resigns after viral Coldplay kiss-cam controversy

Chris Martin of Coldplay performs at the O2 Shepherd’s Bush Empire on October 12, 2021 in London, England.

Simone Joyner | Getty Images Entertainment | Getty Images

Astronomer, the technology company that faced backlash after its CEO was allegedly caught in an affair at a Coldplay concert, said the CEO has resigned, the company announced Saturday.

“Andy Byron has tendered his resignation, and the Board of Directors has accepted,” the company said in a statement. “The Board will begin a search for our next Chief Executive as Cofounder and Chief Product Officer Pete DeJoy continues to serve as interim CEO.”

Byron was shown on a big screen at a Coldplay concert on Wednesday with his arms around the company’s chief people officer, Kristin Cabot. Byron, who is married with children, immediately hid when the couple was shown on screen. Lead singer Chris Martin said, “Either they’re having an affair or they’re just very shy.” A concert attendee’s video of the affair went viral.

In May, Astronomer announced a $93 million investment round led by Bain Ventures and other investors, including Salesforce Ventures.

Byron’s resignation comes after Astronomer said Friday that it had launched a “formal investigation” into the matter, and the CEO was placed on administrative leave.

“Before this week, we were known as a pioneer in the DataOps space, helping data teams power everything from modern analytics to production AI,” the company said in its Saturday statement. “Our leaders are expected to set the standard in both conduct and accountability, and recently, that standard was not met.”

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Nvidia CEO Jensen Huang sells an additional $12.94 million worth of shares

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Nvidia CEO Jensen Huang sells an additional .94 million worth of shares

Jensen Huang, co-founder and CEO of Nvidia Corp., speaks during a news conference in Taipei on May 21, 2025.

I-hwa Cheng | Afp | Getty Images

Nvidia CEO Jensen Huang sold 75,000 shares on Friday, valued at about $12.94 million, according to a filing with the U.S. Securities and Exchange Commission. 

Friday’s sale is part of a plan adopted in March for Huang to sell up to 6 million shares of the leading artificial intelligence company. Earlier this week, Huang sold 225,000 shares of the chipmaker, totaling about $37 million, according to a separate SEC filing. The CEO began trading stock per the plan last month.

Surging demand for AI and the graphics processing units that power large language models has significantly boosted Huang’s net worth and pushed Nvidia’s market capitalization beyond $4 trillion, making it the world’s most valuable company.

Nvidia announced this week that it expects to resume sales of its H20 chips to China soon, following signals from the Trump administration that it would approve export licenses. Earlier this year, U.S. officials had stated that Nvidia would require special permission to ship the chips, which are specifically designed for the Chinese market.

“The U.S. government has assured NVIDIA that licenses will be granted, and NVIDIA hopes to start deliveries soon,” the company said in a statement on Tuesday. Huang said during a news conference on Wednesday in Beijing that he wants to sell chips more advanced than the H20 to China at some point.

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Peter Thiel-backed cryptocurrency exchange Bullish files to go public on NYSE

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Peter Thiel-backed cryptocurrency exchange Bullish files to go public on NYSE

Peter Thiel, co-founder of PayPal, Palantir Technologies, and Founders Fund, holds hundred dollar bills as he speaks during the Bitcoin 2022 Conference at Miami Beach Convention Center on April 7, 2022 in Miami, Florida.

Marco Bello | Getty Images

The Peter Thiel-backed cryptocurrency exchange Bullish filed for an IPO on Friday, the latest digital asset firm to head for the public market.

The company, led by CEO Tom Farley, a veteran of the finance industry and former president of the New York Stock Exchange, said it plans to trade on the NYSE under the ticker symbol “BLSH.”

A spinout of Block.one, Bullish started with an initial investment from backers including Thiel’s Founders Fund and Thiel Capital, along with Nomura, Mike Novogratz and others. Bullish acquired crypto news site CoinDesk in 2023.

“In the first quarter of 2025, Bullish exchange executed over $2.5 billion in average daily volume, ranking in the top five exchanges by spot volume for Bitcoin and Ether,” the company said on its website. The prospectus listed top competitors as Binance, Coinbase and Kraken.

The IPO filing says that as of March 31, the total trading volume since launch has exceeded $1.25 trillion.

Read more CNBC tech news

The filing is another significant step for the cryptocurrency industry, which has fought for years to convince institutions to embrace digital assets as legitimate investments.

It’s already been a big year on the market for crypto offerings, highlighted by stablecoin issuer Circle, which has jumped more than sevenfold since its IPO in June. Etoro, an online trading platform that includes services for crypto investors, debuted in May.

Novogratz‘s crypto firm Galaxy Digital started trading on the Nasdaq in May, moving its listing from the Toronto Stock Exchange. And in June, Gemini, the cryptocurrency exchange and custodian founded by Cameron and Tyler Winklevoss, confidentially filed for an IPO in the U.S.

Meanwhile, investors continue to flock to bitcoin. The digital currency is trading at over $117,000, up from about $94,000 at the start of the year.

President Donald Trump, on Friday, signed the GENIUS Act into law — a set of regulations that establish some initial consumer protections around stablecoins, which are tied to assets like the U.S. dollar with the intent of reducing price volatility associated with many cryptocurrencies.

In its filing with the SEC, Bullish says its mission is partly to “drive the adoption of stablecoins, digital assets, and blockchain technology.”

Crypto industry players, including Thiel, Elon Musk, and President Trump’s AI and Crypto czar David Sacks spent heavily to re-elect Trump and have pushed for legislation that legitimizes digital assets and exchanges.

WATCH: Trump’s crypto plan

Trump's crypto reserve plan is 'incredibly bullish' for crypto as a whole, asset manager says

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