From raw potential to enduring impact.

Before ChatGPT, before AI search was a category, Talia Goldberg wrote a blog post about the next trillion-dollar opportunity. Her thesis: AI would fundamentally change how people find and access information. She met Perplexity Founder Aravind Srinivas at a seed-stage event built around exactly that idea. They couldn't align on valuation, but they stayed in contact. When the company took off and the round turned competitive, top VCs were calling. Refusing to miss the deal, Talia raced to the airport and handed Aravind the term sheet as he was about to board a flight. Bessemer joined Perplexity's Series B in 2024. The company has since raised at a $20 billion valuation.

Twilio's bet was that developers would become the most important buyers in enterprise software, able to wire communication into any product with a few lines of code. Byron Deeter was convinced enough to write a $125,000 seed check over breakfast. Then, when it came time to make the Series A offer, the team skipped the printed term sheet entirely and built a custom app on Twilio's own API to text it directly to Jeff Lawson's phone. The best way to pitch a developer tools company is to act like one. Twilio raised $150 million in its 2016 IPO, the first US venture-backed tech IPO of the year, closing its first day up 91 percent.

Jeremy Levine had three hours to kill before his flight home to NYC from San Francisco. His colleague, Sarah Tavel, suggested they drive to Palo Alto to visit Pinterest, then a five-person company working out of an apartment where at least two of the employees were also living. They sat in the rain for 90 minutes of bumper-to-bumper traffic to get there. The office was nothing. The product was nothing on paper. But Jeremy was so engrossed in the pitch, he had missed his flight by the time he looked at the clock. The eventual red-eye was worth it. Bessemer led Pinterest's $10 million Series A in 2011. Eight years later, Pinterest went public at a $12 billion valuation.

Elliott Robinson had bought a plane ticket to Stockholm when the call came: Max Junestrand already had five term sheets and told Elliott the deal would be signed before he landed and not to bother making the transatlantic flight. Elliott unpacked his suitcase, sent a note saying they'd stay close, and meant it. Four months later, Legora had more than doubled, and Bessemer wasn't going to miss it twice. Elliott and Sameer Dholokia flew from California to New York to meet Max in person. Max’s flight from DC was severely delayed, then ultimately canceled. He took a train. They met him at Penn Station after midnight, got turned away from two bars, and found a third that stayed open until 2 AM. Max ordered a Red Bull and pulled out his laptop for a product demo at the bar. Bessemer ultimately led the Series C at a $1.8B valuation in 2025.

Talia Goldberg has been friends with Fal.ai co-founder Gorkem Yurtseven since college. When she moved to a new townhouse, she invited him and his girlfriend to live in the other unit. She had a front-row seat to everything: the financial services idea that didn't land, the developer tool that brought python into data workflows, and the pivot to Fal.ai, the generative media platform for developers. She believed in the team before she believed in any idea. They were a rare combo of relentless but humble and kind, and had a knack for finding and attracting top talent in unlikely places. What sealed it was her Nest camera, which logged Gorkem arriving home from the office late every single night for months. That was just how he worked. She'd seen enough. She had to back them. Bessemer joined Fal's Series B in 2025. The company has since raised at >$4.5 billion valuation and grew to many hundreds of millions of revenue in less than two years.

Kent Bennett got a call from Steve Papa, the founder of Endeca, with a simple message: three of his best engineers were starting something, and Kent would regret it if he passed. Kent didn't invest. He did, however, hand them the empty office next to his. He passed again, skeptical about the model, when they landed on a restaurant POS. Then one morning Aman Narang walked him through how they'd baked payments directly into the product. Kent called his mentor Felda Hardymon on the spot: "I made a massive mistake." Felda's advice: hand them a term sheet that day, and every day until they accept. It took a while. They did. Toast went public in September 2021 at a valuation of $20 billion.

At a poker game in 1994, MIT Professor Ron Rivest explained to David Cowan how cryptographic certificates could enable trust on the web. David flew to Florida, drove to the Everglades, and tracked down Addison Fischer under a tin-corrugated roof to propose an investment in RSA Data Security. Fischer said no. He was, however, open to an equity deal in a new certificate authority. David filed the incorporation papers in Delaware in January 1995, hired a CEO, changed the name to VeriSign, and convinced Netscape to embed the public key that created the first SSL lock for encrypted web traffic. VeriSign went public in January 1998 and today carries a market cap of more than $23 billion.

Bessemer had the opportunity to invest in pre-IPO secondary stock in Apple at a $60M valuation. Neill Brownstein called it "outrageously expensive."

Byron Deeter flew straight to Atlassian in 2006 when he caught wind of a developer tool from Australia (of all places!). Notes from the meeting included “totally self-financed, started with a credit card” and “great business, but Scott & Mike don’t ever want to be a public company.” Years and countless meetings later, the first opportunity to invest emerged in 2010, but the $400m company valuation was thought to be a tad “rich.” In 2015, Atlassian became the largest tech IPO in Australian history, and the shares we passed on are worth more than a billion dollars today.

“Stamps? Coins? Comic books? You’ve GOT to be kidding,” thought David Cowan. “No-brainer pass.”

Jeremy Levine spent a weekend at a corporate retreat in the summer of 2004 dodging persistent Harvard undergrad Eduardo Saverin's rabid pitch. Finally, cornered in a lunch line, Jeremy delivered some sage advice: "Kid, haven't you heard of Friendster? Move on. It's over!"

Incredibly, Bessemer passed on Federal Express seven times.

David Cowan's college friend rented her garage to Sergey and Larry for their first year. In 1999 and 2000 she tried to introduce Cowan to "these two really smart Stanford students writing a search engine." Students? A new search engine? In the most important moment ever for Bessemer's anti-portfolio, Cowan asked her, "How can I get out of this house without going anywhere near your garage?"

In 2006 Byron Deeter met the team and test-drove a roadster. He put a deposit on the car, but passed on the negative margin company telling his partners, “It’s a win-win. I get a great car and some other VC pays for it!” The company passed $30B in market cap in 2014. Byron paid full price for his Model X.