Inspired with Alexa von Tobel

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.

Growing up, Ara saw firsthand how hard his father worked as a contractor running a trade business. When he met Vahe Kuzoyan, a fellow Armenian immigrant whose family worked in the trades, they saw an opportunity to help their own families work more efficiently and grow their businesses. Over time, word spread and they decided to go all in on building ServiceTitan. With a valuation over $9B, ServiceTitan helps thousands of customers in the trillion dollar trade industry. Ara shares how his dad wandering the aisles of Barnes & Noble kicked off his coding skills, why the two victories of B2B software are making customers money or saving them money, and how he and Vahe strive to cultivate a winning culture.

Co-founder dynamics can be notoriously challenging. But Waseem Daher and his co-founders, Jeff Arnold and Jessica McKellar, are now building their third business together. Their most recent company is Pilot, which they started in 2016 to solve a pain point they experienced as founders: how time-consuming it can be to manage company finances. Pilot is now the largest startup and SMB bookkeeper in the United States, serving over 1,900 clients. Waseem shares why speed is the most critical advantage for startups to leverage, how he learned to delegate in later stages, and why a founder's strongest ethical obligation is to their customers and team.