Inspired with Alexa von Tobel

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. 

What if brands were empowered to deliver personalized experiences online, just as well as they could do in a store? That's the idea that underpins Klaviyo, the leading customer and marketing automation platform. Andrew Bialecki cofounded Klaviyo in 2012 and now serves over 100,000 brands, helping them generate $28 billion in revenue for its customers in 2021 alone. Andrew shares why he bootstrapped the business until profitability, how early partnerships can be a key to efficient customer acquisition, and why he feels like he's only achieved 1% of Klaviyo's potential.

After business school, David Velez moved to Latin America to become a venture capitalist. But after finding a dearth of startups to invest in, he founded one of his own. Since then, Nubank has grown into the largest independent digital bank in the world. The Brazil-based company has over 39 million users and a valuation north of $25 billion. David shares how Nubank built a waitlist of over a million people in just 18 months, why the company's first product was a purple credit card, and how waking up at 5am every day makes him a better founder.(Original Air Date: Jun-9-2021)

In 2013, a team of academics at UC Berkeley was working to solve massive data challenges that were impacting the tech companies in their backyard. Fast-forward and that team now represents the co-founders of Databricks, a data and AI company used by more than 5,000 organizations worldwide. In 2016, Ali Ghodsi stepped into the CEO seat and the company is now valued at $28 billion. Ali shares why he prioritizes building leaders over making decisions, how he sees the future of AI, and how he navigates the unique experience of having six co-founders.(Original Air Date: 3-17-2021)