For Starters with Alexa von Tobel

Today, Webflow is a company valued at over $4 billion. But it took Vlad and his cofounders repeated attempts to get the company off the ground. In 2012, they started gaining steam for their vision to allow people to create websites with no coding experience. The company now brings the power of software engineering to designers through an intuitive visual interface and has grown to over 3.5 million users. Vlad shares how Webflow has made its user community a superpower, why having two kids when he started the company gave him extra motivation to succeed, and how he predicts no-code and generative AI will intersect. 

While in business school, Jeff Raider co-founded Warby Parker and watched the iconic glasses company take off. So when his friend, Andy Katz-Mayfield, G-chatted him one day with an idea to reimagine mens' razors, Jeff was intrigued. In 2013, the duo started Harry's to create exceptional shaving and personal care products that better meet the needs of modern men. The company has since reached tens of millions of people and become the #2 men's shave brand in the country. Jeff shares how they signed on a German factory to manufacture a million blades before writing a business plan, how their first referral program led to over 100,000 email sign-ups in a week, and how he found the silver lining when the FTC blocked a planned acquisition of Harry's in 2020.

At fourteen, Reese Witherspoon’s acting career kicked off. In the ensuing decades, she has become an A-list star, earning an Academy Award for her performance in Walk the Line and starring in iconic films like Legally Blonde and Election. But despite her success, she found herself underwhelmed by the quality of roles for women. In 2016, she started Hello Sunshine, a cross-platform media brand and content company, to drive the production of female-centric content. Hello Sunshine was named one of Time Magazine’s 100 Most Influential Companies and was acquired for $900M in 2021. Reese shares why female collaboration fuels creativity, how Hello Sunshine has found success across so many media platforms, and what she learned from her first business (a custom barrette company in the third grade). 

Jyoti Bansal is a serial entrepreneur, through and through. In 2008, he first made the leap from startup engineer to CEO with AppDynamics, a company that was acquired by Cisco for $3.7 billion just under a decade later. After giving retirement a shot, he returned to the founder seat: he started software delivery unicorn Harness, cybersecurity platform Traceable, startup accelerator BIG Labs, and VC firm Unusual Ventures—and has more than 25 US patents under his name. Jyoti shares his simple formula for finding product-market fit, why ringing the Nasdaq closing bell was part of his Cisco negotiation, and how he's learned not to stress about things outside of his control.

Over his decade-plus at Microsoft, Eugenio Pace became an expert in cloud computing and identity management, co-authoring several books on the topic. His drive to solve the problem of identity management for fellow developers inspired him to start a company of his own, Auth0, in 2013. Over eight years, he scaled the company into a trusted global brand, leading to a 2021 acquisition by Okta in a $6.5 billion dollar deal. Today, Eugenio is the President of Customer Identity at Okta, serving Auth0's and Okta's combined customer base. Eugenio shares why they decided to offer parts of Auth0 for free, why he attributes his success to a CEO development program, and why he felt like it was the right moment to sell his company—even though Okta started courting him years prior.

Tim Chen, co-founder and CEO of NerdWallet, shares the evolution of NerdWallet from a credit card shopping tool to a platform offering assistance with various financial products. They explore self-driving wallets and the importance of trust in accurate decision-making. Tim highlights his scrappiness in the early days of NerdWallet and the influence of his parents. He discusses favorite interview questions, irreversible decisions, and book recommendations emphasizing trust in business.

While a sophomore at Harvard, James Hirschfeld put lots of time into planning his 21st birthday party—but when it came time to figure out invitations, there was no option that spoke to him, between expensive stationery and clunky online tools. He started Paperless Post in 2009 along with his sister, Alexa, and has since reimagined the experience of sending and receiving invitations for over 175 million users. James shares why it was an uphill battle convincing investors that consumers wanted premium tools for digital communication, how they turned the business impact of the pandemic (the worst thing that could happen to a company centered on events) into an investment in the future, and why user trust and loyalty is sacred.

In 2012, George Fraser teamed up with his lifelong friend, Taylor Brown, to build Fivetran. Their initial vision was completely different from what Fivetran is today: a fully managed automated data integration provider, valued at over $5 billion. But the two listened to customer conversations and realized that they could build a viable business around a singular pain point. Fivetran now serves thousands of customers and hundreds of leading brands across the globe. George shares how his PhD in Neurobiology impacts his style as a founder, why fear of failure is an underrated motivator, and why they got creative with a major acquisition in order to build a full-spectrum offering overnight. 

Allon Bloch is no stranger to starting companies, but when he launched K Health, he was new to healthcare. Before K Health, he was the CEO of website publishing platform Wix and car retailer Vroom. But his father's health struggles inspired him to turn his focus to delivering high quality medicine at scale. He co-founded K Health in 2016 and has scaled the platform into the #1 downloaded app in the medical category, covering over 6 million people. Allon explains how K Health leveraged AI early on to teach a machine the language of medicine, why he believes it's a great time to be a healthcare entrepreneur, and why he attributes his success to the partnership of strong co-founding teams.

Nearly twenty years ago, Anthony Casalena was a student at the University of Maryland who wanted to build himself a website. Finding no easy platform in the market, he created his own. Today, Squarespace is an all-in-one website building and ecommerce platform used by more than 4.2 million people. Anthony worked as a team of one for the first few years, but now has over 1,800 employees and took Squarespace public in 2021. Anthony shares how he got his idea off the ground with a $30,000 investment in servers and Google AdWords, why it still feels surreal to see a Squarespace ad at the Super Bowl, and how running a public company is completely different than what he expected.