Inspired with Alexa von Tobel

When Olivier and his co-founder launched Datadog in 2010, they didn't write a single line of code for the first six months—despite having backgrounds as engineers. Out of the gate, they have made it their mission to listen to customers and understand what problems they can solve for them. Fast-forward a decade: Datadog is the essential monitoring platform for cloud applications and a true DevOps pioneer. The company IPOed in 2019 and its market cap now exceeds $27B. Olivier shares why he thinks of companies as a set of systems, how to push forward even when VCs tell you no, and why he's still subscribed to all Datadog support emails.

When Daniel Gross was 18, he traveled from Jerusalem to Silicon Valley to join Y Combinator as the youngest founder ever accepted at the time. In just a few short years, his search engine startup, Cue, was acquired by Apple. Now, he's at the helm of Pioneer, a fully remote accelerator that backs unconventional startups from around the world—no matter the founder's zip code. Daniel shares why community is critical for business-building, what it means to be a company born online, and why he thinks space will fuel the next decade of innovation.

Why is it so hard to stay on top of your email? After building Rapportive, the first Gmail plugin to scale to millions of users, Rahul Vohra was ready to tackle the problem of email itself. In 2014, he started Superhuman with the goal of building the fastest email experience in the world. If his waitlist of over 300,000 people is any indication, he's done just that. Rahul shares why domain expertise matters, how he learned to choose a strategy and stick with it, and why you have to figure out positioning before pricing.

At his core, Jack is a creator. While his musical group Pomplamoose had taken off on YouTube, he realized that the mechanism for turning his fans' attention into dollars was broken. So, he built Patreon, a membership platform that makes it easy for creators to earn salaries directly from their biggest fans. Since its launch in 2013, Patreon has paid out more than $1 billion to creators on its platform. Jack shares why the myth of the starving artist is over, why he's willing to work harder than the competition, and how all creators should think about engaging their fans.

Why isn't it easy to securely prove your identity online? That's the big question Blake Hall is working to solve with ID.me, the next-generation digital identity network, that is now used by government agencies, healthcare organizations, and retailers alike. A third-generation soldier, Blake started his post-college life leading a reconnaissance platoon in Iraq, for which he was awarded two Bronze Stars. With a Harvard MBA in hand, he set out to build ID.me and has scaled it to over 24 million users. Blake shares the big pivots he took in his early startup years, what his military career taught him about leadership, and why ID.me has credentialed 30% of all nurses in the country to give back during Covid-19.

Julie Bornstein is a seasoned e-commerce executive, who has spent her career building major retailers online, including Nordstrom, Sephora, and Urban Outfitters. After scaling Stitch Fix to over $1 billion in revenue as COO, Julie has launched The Yes - the digital department store of the future. Julie shares what it's been like to launch during COVID, how she has gained the confidence to set out on her own, and why she believes shopping should be more like browsing on Spotify.

After their day jobs wrapped, Wade and his co-founders spent their nights building what would eventually become Zapier, the workflow automation tool. Originally based in Missouri, they decided to put their full focus onto their budding startup by joining the Y Combinator accelerator. Zapier is now one of the highest valued companies to come out of the program. Today, it has millions of users and connects to more than 2,000 apps. Wade shares how he got his first beta customer from a cold email, how the company's formula for scaling is a blend of data and intuition, and the surprising upsides of having relied on a fully remote team from the earliest days.

When he was a child, he set up a stand in front of his house to sell his mom's clothes. In college, he ran an airline miles business with 17 friends working out of his apartment. And post-college, he started Brightstar, which became the world's largest global wireless distribution company, with over $10 billion in revenue. Marcelo Claure's career accomplishments run deep. He led Sprint through its historic merger with T-Mobile and now serves as COO of SoftBank and executive chairman of WeWork. Marcelo shares how he picks new pursuits (like doubling down on WeWork), why his current goal is to set the world record for being the oldest soccer player in a professional match, and why his latest venture is leading SoftBank's new Opportunity Fund, which will invest $100 million in companies led by people of color.

Zach Reitano, entrepreneur focused on personalized healthcare, shares how Covid accelerated telemedicine adoption, the importance of building trust with patients, and the impact of Ro's commercial featuring his dad.

After co-founding the top organic baby food brand in the country, Jessica Rolph got her second startup idea from an unlikely source: a doctoral thesis on child development. Jessica launched Lovevery in 2015 to offer products to help parents feel confident they're delivering the tools their children need. The company has taken off, with backers like Maveron and the Chan Zuckerberg Initiative. Jessica shares why becoming a serial entrepreneur is scarier than it looks, why she chose to build Lovevery in Boise, Idaho, and what tips she swears by to help us all parent better during COVID and beyond.