On a late spring evening in New York's Flatiron District – the heart of the city's buzzing tech ecosystem – more than 100 startup founders convened for dinner. At one end of the table sat an early-stage pediatric mental healthcare founder, and a few spots away sat a person building a data privacy startup. Meanwhile, a founder of a well-known fintech startup made a lap around the room.
At the center of it all was Alexa von Tobel, a staple of the New York VC community and one of the investors behind VC firm Inspired Capital. Since co-founding the firm in 2019, she's hosted Inspired's portfolio companies for an annual dinner where startup founders can build community and find common ground.
It's an important ritual at a firm like Inspired, a generalist VC fund that now commands nearly $900 million in assets under management and invests in startups revolutionizing stagnant markets, rather than focusing on specific sectors.
It's also on brand for von Tobel, who has earned a reputation in the VC industry not just for taking a hands-on approach when mentoring portfolio companies, but for being the person who knows absolutely everyone.
"She sort of collects people and keeps them around, so I know her elementary school friends as well as her business school friends as well as her husband's colleagues from his first job," said Lucy Deland, one of Inspired Capital's co-founders who's known von Tobel since they were undergraduates together at Harvard University.
"She brings people together, constantly."
Born and raised in Jacksonville, Florida, von Tobel attended Harvard University, where she graduated with a degree in psychology. It was during this time that she developed a keen interest in the intersection of entrepreneurship and finance, driven in part by her work with the psychology department's 'Happiness Lab,' which studies the science of happiness — as well as a number of peers who would also go on to make a name for themselves in the tech world.
"Mark Zuckerburg was one of my classmates, so I had an idea of what an entrepreneur is," she said. "I've been an investor my whole life, since right out of college."
After graduating in 2006, von Tobel moved to New York to complete a stint at Morgan Stanley as an analyst in its proprietary trading group and later spent six months heading up business development for file-sharing service Drop.io, which was acquired by Facebook in 2010.
She was also working toward an MBA at Harvard Business School but dropped out after her first few months in 2008 to build LearnVest, a fintech startup that aimed to democratize financial planning and empower individuals to take better control of their finances.
Over the next eight years, LearnVest raised over $75 million in venture capital funding from firms including Accel Partners and American Express Ventures. The startup was also an early arena for von Tobel to build out her network: in 2013, she hired Mark Batsiyan as the startup's director of business development.
When Northwestern Mutual acquired LearnVest in 2015, the pair moved together to the financial giant, with von Tobel remaining LearnVest's CEO and later becoming Northwest's chief digital and innovation officer — under that umbrella, she worked with Batsiyan to launch the company's first venture fund, NM Future Ventures.
"Learnvest was solving a problem I believed in, but I joined because of Alexa—the core bet I was making was on her," he said. Batsiyan added that he and von Tobel were a deal team of two that didn't use any bankers to sell LearnVest, doing the diligence themselves after hours. The pair had an understanding that they'd eventually move on together from Northwestern Mutual to start something new.
"Alexa had started angel investing right as the tech ecosystem began to grow more rapidly in New York," he said. "And after convincing the Northwestern Mutual's executive to launch a venture fund and doing it for a while, we realized we were good at it."
Four years later, in 2019, von Tobel was ready to re-join the startup world, this time to support other founders. She co-founded Inspired Capital and tapped multiple people in her network to help make the launch a success, including Deland, a founding member of Paperless Post and von Tobel's early friend at Harvard; and Penny Pritzker, the former US Secretary of Commerce in the Obama Administration.
As a sector-agnostic fund, Inspired focuses on investing in mission-driven companies that are poised to disrupt traditional industries and drive significant societal impact. The firm debuted with a $200 million fund and has backed dozens of AI, healthcare, fintech, and software startups. Notably, Inspired has backed AI startup Mosaic, fintech platform Rho, and software quality assurance startup QA Wolf.
"At my best, I'm helping build companies that I wish existed, and they're big, wild ideas that are moving the world forward," von Tobel said.
For Brynne McNulty Rojas, von Tobel has been a key player in her startup's success.
While the two long shared a large group of mutual friends and business connections, the pair hit it off at a conference in Miami in 2018. They reconnected a year later while founding their respective companies — von Tobel had just launched Inspired, while McNulty Rojas was building Habi.co, a real estate startup streamlining the home-ownership process in Latin America.
Inspired went on to lead the company's $10 million Series A funding round, and Habi has since raised more than $550 million in VC funding from other firms, including 8VC, SoftBank's Latin America Fund, and Tiger Global Management.
For McNulty Rojas, having von Tobel and Inspired on her cap table at an early stage has been key to Habi's transition to a growth-stage startup.
"Alexa is so well connected and made sure to set us up with the right partners at the right firms and helped us frame our conversations," McNulty Rojas said. She added that in addition to helping her team go through various financial models and slide decks, von Tobel connected Habi to SoftBank, which eventually led the startup's $100 million Series B in 2021.
Von Tobel's background as a founder-turned-investor has not only been instrumental in shaping Inspired Capital's investment philosophy, but her ability to identify high-potential startups and guide them through critical growth stages has solidified her reputation as a VC who keeps cool under pressure.
"I don't think Alexa gets overwhelmed," Deland said. "We talk a lot about how, for founders, one of the qualities we're trying to assess is whether stressful situations put you in fight-or-flight or if they turn you on. For Alexa, stress-absolutely puts her in her clearest mindset and focuses her energy on solving a problem."
In the five years since Inspired's launch, it's closed two additional funds — a $281 million Fund II in 2021 and a $330 million Fund III earlier this year — and has stayed focused on its bread and butter: making pre-seed through Series A investments ranging from $1 million to $15 million.
The firm has invested in more than 70 startups that have collectively raised $1.5 billion in follow-on capital.
Even as the scope of Inspired has grown, founders say von Tobel is as hands-on as ever.
"One thing I was really excited about in terms of working with Alexa is that she is extraordinarily ambitious and really in it to win it, completely all-in," McNulty Rojas said. She recalled a recent instance of working through a business problem. Although von Tobel was on vacation outside the country, she stepped away from a fancy dinner to take McNulty Rojas's call and brainstorm solutions.
"There hasn't been a single time when I've reached out to Alexa for advice or assistance, and she hasn't made herself available," she said. Whether it's 11 p.m. on a Saturday or 7 a.m. on a Sunday, she'll do whatever it takes to ensure that you're going to be a success. "
Back at Inspired's annual founder dinner, von Tobel's plate of tacos, elote, chips, and guac went untouched for most of the evening while she popped up from her seat again and again, greeting everyone in the room. She's dressed in head-to-toe white with a large turquoise necklace — among VCs in New York, many of whom stick a uniform of t-shirts and jeans, von Tobel is known for her style in clothing as well as with spaces. Benjamin Vandiver designed Inspired Capital's HQ, which features large couches, artwork, and statement light fixtures. The space was featured two years ago in Architectural Digest.
In rare moments where she sits down, von Tobel was tapping on her phone — which is covered in a bright red case so it's easy to find — and chipping away at a neverending stream of inbounds.
Her phone has hundreds of unread notifications. Some of these messages are certainly investing-related: setting up meetings for pitches, working through diligence, and landing term sheets. But beyond the day-to-day work she does with startup founders, von Tobel has worked relentlessly in recent years to build up the Inspired brand — and, by extension, her own. She hosts a podcast with Inc. Magazine, which is called "For Starters" and covers conversations between her and notable entrepreneurs, including Notion's Ivan Zhao and Winter Olympics Gold Medalist Lindsey Vonn.
She's also written multiple books: two investing titles for adults and Rebel Girls Money Matters, a financial literacy book for young girls published earlier this year. With fellow New York VC firm Primary, she and Inspired have co-hosted an annual conference in the fall called Primary Summit, which brings together the New York startup ecosystem.
"It's that sort of classic extroversion where she gains energy from all of these relationships and touchpoints, whether it's texting or meeting in person — it's all just fuel," Deland said. "Being in a room with Alexa is like a caffeinated experience without any substances."
