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Figma’s CEO sent cold emails to and bought coffee for his ‘heroes’ while convincing ex-coworkers to use his product before its $68 billion success

Emma Burleigh
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Emma Burleigh
Emma Burleigh
Reporter, Success
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August 11, 2025, 11:07 AM ET
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Dylan Field may not be helming a $68 billion company if it weren’t for cold-calling his former coworkers and taking his tech “heroes” for coffee—and execs at Google and Squarespace found success the same way.Bloomberg / Contributor / Getty Images
  • Figma’s billionaire CEO Dylan Field hit up his former coworkers from LinkedIn, Flipboard, and O’Reilly Media as the then 19-year-old was looking to get his design tool off the ground. The millennial cofounder also cold-emailed his tech “heroes” to invite them out for coffee. Now, Figma is a $68 billion success. And multimillionaires and executives at Google and Squarespace have found success the same way.

Job-seekers are all turning to out-of-the-box ways to advance their careers: from delivering donuts to Silicon Valley bosses, to waitressing at tech conferences to hand out CVs. However, Figma CEO Dylan Field used some age-old tricks to get people on board with his now $68 billion breakout success.

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The 33-year-old CEO was just 19 when he founded the online design tool in 2012, and the aspiring tech entrepreneur pulled on any loose thread he could find to persuade others to use it. 

“Really, the first users of Figma, a lot of it was cold-emailing and people in-network,” Field recently revealed at Y Combinator’s AI startup school. “So folks that I had interned with…and from that, there were people I could reach out to that could tell me others to talk with.”

Field had dropped out of the Ivy League school Brown University and took up Peter Thiel’s prestigious fellowship, granting Field $100,000 to launch his startup. But if it weren’t for his nine-month research assistant job at Microsoft, four-month data analytics internship at LinkedIn, and two internships at aggregation software company Flipboard, he may not have amassed a base to get his business running. 

Field didn’t stop at hitting up his ex-coworkers and gaining steam behind a screen—he also scraped the internet for the best tech talent. If they agreed to hear out his Figma dream, he took them out for coffee and sang his praises of their influence. Surprisingly, in a world of rampant ghosting, a lot of people took the bait. 

“I just looked online, like, ‘Who are the designers that I think could be really helpful to us and I respect their work?’ If they answer my email and they let me buy them a coffee, it’ll just be like a personal moment for me, because they’re my hero,” Field recalled. “And a lot of them replied. It’s kind of wild that people reply to cold emails, but they do.”

Fortune reached out to Figma for comment. 

Millionaires and executives at Google and Squarespace who put themselves out there 

Figma’s CEO isn’t the only one admitting to reaching out to the upper echelons of business for help out of the blue—and actually finding success from it. 

Venture capitalist and multimillionaire Rashaun Williams, now a host on the iconic investing show Shark Tank, found success by employing a strategy he calls “sneaking into the party.” With few business opportunities growing up on the South Side of Chicago, he would insert himself into any event, starting every conversation with “Hear me out.” Williams told Fortune: “I don’t mind cold-calling people. I don’t mind pulling up at conferences.”

Google executive Sameer Samat also didn’t achieve success by sitting on the sidelines. He began his meteoric rise in tech by plucking up the courage to cold-email one of the biggest names in his industry: Google cofounder Sergey Brin.

At the time Samat was in his twenties, trying to make it in the startup world, when a cofounder at his company Mohomine was weighing leaving the business for graduate school. Unsure of how to convince them to stay, he emailed Brin at 3 a.m., hoping for some words of wisdom. A mere minute later, Brin replied and invited Samat and his entire team down to Google’s headquarters, interviewing them on the spot. Brin offered Samat a job, but the now executive turned down the opportunity, opting instead to build up his company. 

Even the CMO of $7.2 billion company Squarespace calls cold-calling employers the “life hack to avoiding long interview processes.” Years before her success in tech, Kinjil Mathur spent her summers as a college student skimming telephone books to find the contacts of businesses and professionals in her city. She would go to the company listings section, and started cold-calling businesses inquiring about internships—stating she was even willing to do without a paycheck. 

“I was willing to work for free; I was willing to work any hours they needed, even on evenings and weekends. I was not focused on traveling,” Mathur told Fortune. “You really have to just be willing to do anything, any hours, any pay, any type of job—just really remain open.”

Join us at the Fortune Workplace Innovation Summit May 19–20, 2026, in Atlanta. The next era of workplace innovation is here—and the old playbook is being rewritten. At this exclusive, high-energy event, the world’s most innovative leaders will convene to explore how AI, humanity, and strategy converge to redefine, again, the future of work. Register now.
About the Author
Emma Burleigh
By Emma BurleighReporter, Success

Emma Burleigh is a reporter at Fortune, covering success, careers, entrepreneurship, and personal finance. Before joining the Success desk, she co-authored Fortune’s CHRO Daily newsletter, extensively covering the workplace and the future of jobs. Emma has also written for publications including the Observer and The China Project, publishing long-form stories on culture, entertainment, and geopolitics. She has a joint-master’s degree from New York University in Global Journalism and East Asian Studies.

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