Building a business is a team sport. No one understands that better than Josh Reeves and his co-founders at Gusto. Since 2012, they have been hard at work building the leading people platform that empowers small businesses to take care of their hard-working teams. With a valuation of nearly 4 billion, Gusto now helps over 100,000 companies with payroll, health insurance, HR, and more. Josh shares why he focused on the small business segment, why it's critical to put employees first, and why raising venture capital is just like hiring.

Dr. Paul Judge is a serial entrepreneur through and through. After stumbling into coding as a kid, he has spent his career as an expert in information security issues. With a Ph.D. and 30 patented technologies in his name, he's co-founded three companies that have been acquired and is currently the co-founder of Pindrop, which has raised over $100 million in funding. Now, he's paying it forward to other founders in Atlanta through TechSquare Labs. Paul shares how he removes the fear of failure, why cofounders need to share a sense of urgency, and how to align your time management to your priorities.

In 2011, Steve and his co-founders set out to build a company. They understood the power of a vertical strategy and realized that restaurants were ripe for innovation. Enter Toast, which powers restaurants with point of sale, front of house, back of house, and guest-facing technology. Toast has grown rapidly with a clear focus on their customers: restaurants. Toast has raised a whopping $850 million in venture capital and was recognized as the third fastest growing tech company in North America. Steve shares the secret to gauging product market fit before you build a product, how Toast won its first customers through competitive pricing, and why Covid pushed technology from a nice-to-have into a must-have.

Chris Bennett grew up in Miami, and out of his 31 first cousins, he was the first to go to college. Looking back, he realized it was his access to early childhood education that set him on his trajectory—to a degree from Wharton and a job in private equity. So, he launched Wonderschool with an aim to provide high quality early education to every child. The education marketplace has already matched thousands of families with quality educators. Chris shares why in-home education will pay a role in the future of edtech, the importance of talking to customers, and why the best moment to date was Wonderschool's very first enrollment.

At 15, Dylan Diamond built an app to help his high school classmates manage their schedules. The simple tool was an instant hit, with over 90% of the campus using the app daily. Fast-forward to college: Dylan met Max, and the two decided to go all-in on Saturn. They are working to build community around the calendar in high schools, with a big vision fueling them: to own the time layer of the internet. Dylan and Max share why retention is social, how living together has given them an "always on" founder mindset, and what they learned from their early work experience at Tesla and Havas.

What if you could discover what diseases you're genetically predisposed for? That's the problem Othman Laraki set out to solve at Color, with a tech-forward approach to genomics. Since launching in 2013, Color's aim has expanded to building public health infrastructure (making it no surprise that Color is one of San Francisco's biggest Covid-19 test providers). With degrees from Stanford and MIT and tech experience from Twitter and Google, Othman is bringing an outsider's view to healthtech. Othman shares why entrepreneurship requires a level of irrationality, why a minimalistic UI is critical in healthcare, and how he defines Color's customers.

When Brynne moved to Bogota, Colombia after graduating from Harvard Business School, she quickly realized that there was no tech solution for finding a home. In 2019, she teamed up with co-founder Sebastian Noguera to tackle the $10 trillion Spanish Latin American real estate market with the launch of Habi. In just the past year, Brynne and Sebastian have positioned Habi as Colombia's largest homebuyer, scaled their team to 50 employees, and built a game-changing dataset for the Colombian real estate market. Brynne shares why choosing a cofounder is like getting married, what makes the Bogota tech scene so special, and the importance of holding strong views weakly.

Trying to get a diagnosis for a myriad of symptoms she was experiencing, Julia Cheek ended up spending thousands of dollars on lab testing bills for results she never even saw. Julia saw an opportunity to transform the 25 billion dollar lab testing industry, so in 2015, she founded Everlywell. With 30+ types of at-home lab tests, Everlywell has scaled to tens of millions in sales and is sold in Target and CVS stores nationwide. Julia shares why she decided to pitch on SharkTank, what being a professional equestrian taught her about entrepreneurship, and how she led her team through an industry-leading response to Covid testing.

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.