Inspired with Alexa von Tobel

What if every American were an investor? At Robinhood, Vlad Tenev is on a mission to make the financial system work for everyone. He co-founded the company in 2013, and the fast-growing brokerage has become an investing giant. With over 13 million users and $1 billion in funding, it's no surprise incumbents have been influenced by Robinhood's model, which drove an industry-wide shift toward commission-free trades. Vlad shares why he decided to build Robinhood as a mobile-first platform, how Covid helped to accelerate user growth, and why waking up to an analog alarm clock is a critical part of his routine.

Most startups set out to tackle massive problems, but working to develop a low-cost, long-duration energy storage solution that will enable the electric system to be 100% renewably powered? That's a big one by any standard. At Form Energy, Mateo Jaramillo and his co-founders are working to bring that very vision to life, leveraging the smartest minds in the energy storage space. Mateo shares why he bet his career on the climate tech industry after attending Yale Divinity School, how his time at Tesla taught him the importance of top-quality talent, and what it was like to step into the shoes of a founder at age 40.

What if you could perform like a superhuman at work? That's the idea behind Forethought, the AI company on a mission to bring intelligence to every single workflow. Co-Founder Deon Nicholas is building technology to augment—not replace—workers, starting with an AI for customer support. Since launch, Forethought has resolved over 500,000 customer support claims automatically, won TechCrunch Disrupt's startup contest, and received funding from the likes of Ashton Kutcher and LL Cool J. Deon shares how he learned to be true to himself as a leader, how to identify your business's customer profile, and why technical founders need to spend more time on go-to-market.

Topping the app store charts is a once-in-a-lifetime experience—unless you're a mobile entrepreneurship genius, like Prerna Gupta. She and her husband created hit music apps, like AutoRap, that have been downloaded by 350 million people. Now, Prerna is at the helm of Hooked, building a new television network for Gen Z that has already reached an astronomical number of viewers around the world. Hooked uses data to upend the traditional model, rewriting how content is created and distributed. Prerna shares how her idea for Hooked was inspired by a year of travel, what three rules every mobile app creator should follow, and why TV will look fundamentally different in a decade.

Upon reading that most successful founders start their companies by age 37, David Rubenstein decided to join them. A lawyer who worked in the Carter administration, David set out to start a private equity firm based in Washington DC. He co-founded Carlyle in 1987, and the firm has grown to become an industry giant that manages over $221 billion. David is an avid reader-turned-author who interviewed icons like Jeff Bezos and Oprah for his new book, How to Lead. David shares how he built a strong brand through recruiting top talent, why the most elusive thing in life is the pursuit of happiness, and why the best leaders share humility and a desire to give back to society.

The story behind Slack—the communication platform used by millions around the globe—is almost a happy accident. Cal Henderson and his co-founders had been toiling away on a gaming startup, Glitch, when they realized the product of most value within their organization were the tools they'd hacked together to collaborate across locations. That collaboration tool spun off into Slack, which IPOed in 2019 and now has a market cap of over $16 billion. Slack has become more vital than ever in 2020, standing in as our "digital office." Cal shares how to scale an engineering organization, why the role of the office is forever changed, and how to master personal time management.

What if you could get a life insurance policy in just 3 minutes, 24/7? That's now a reality, thanks to Peter Colis and his digital-forward life insurance startup, Ethos. Ethos is a next-gen InsureTech company that puts accessibility front and center, underwriting applicants in real-time via proprietary algorithms. To date, the company has raised $100M in venture capital and serves people ages 18-85 across 49 states. Peter shares how his experience as a boxer helps him stay calm in the face of adversity, how Covid accelerated the adoption of financial technology, and how he overcame imposter syndrome as a student at Stanford

Parts of our financial system are so deeply ingrained that innovation seems impossible. But after realizing how archaic the credit score was, Jason Gross set out to fix it. He launched Petal to reinvent the credit card and leverage banking data to democratize credit scoring. He's long been committed to fairness in financial services, having served on the Consumer Financial Protection Bureau’s Consumer Advisory Board. Now, with tens of thousands of customers, Petal is rising to combat the financial inequity that Covid has exacerbated. Jason shares how being a lawyer has made him a stronger founder, how to hire a low-ego team, and the importance of prioritizing sleep.

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.

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.

When each member of his family grappled with a life-threatening illness—himself included—Zach Reitano found his mission as an entrepreneur: to provide personalized health care to everyone on the planet. In 2017, Zach and his co-founders started Ro. With offerings that span Roman (for men's health) to Rory (for women's health), Ro quickly took off and, in 2019, it was named one of the world's most innovative companies by Fast Company. Zach shares how Covid has accelerated the adoption of telemedicine, why building trust with patients is so critical, and why putting his dad in Ro's commercial was one of his best decisions to date.

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.

When you sit down to work, do you often find yourself starting at a blank page? Adam and his team at Almanac are trying to fix that. Just as Github has allowed engineers to access a database of code, Almanac is doing the same for knowledge workers and documents. With user growth doubling month over month and a roster of investors that includes 100 expert startup operators, Almanac is on a mission to democratize access to knowledge. Adam shares why we're at an inflection point of businesses going fully digital, why he measures success by users outside of silicon valley, and how an internship at Apple made him realize he wanted to be a founder.

After co-founding and selling ad-tech platform Yodle, serial entrepreneur Milind Mehere had identified a new pain point. After Seeing his investments plummet during the last recession, he wanted to create a digital wealth-management platform that would get people on the road to financial independence. So, in 2014, Milind he launched YieldStreet—which has since been cited on the Inc. 5000 as the fastest-growing company in New York City. on the Inc. 5000 list. Milind shares how YieldStreet educates consumers about the alternative investments space, why founders should personally be involved in a company's first 100 hires, and why he believes the next decade will be the golden age of fintech.

Steven had a big realization: Selfies with celebrities are the new autograph. With strong conviction in his idea, he and his co-founders set out to launch Cameo, the marketplace that allows fans to book video shoutouts from a library of over 30,000 celebrities. The company has taken off—with more than 850,000 Cameos recorded, over $65M in VC funding, and an astounding 1,000 percent increase in bookings during the Covid pandemic. Steven shares how Cameo came back from "the worst product launch of all time," why the best businesses grow via word of mouth, and why he requires a whiteboard and marker in interviews for future Cameo employees.

Bryan came up with the idea for his first startup on the back of a cocktail napkin—and went on to sell the resulting business, WHI solutions, to eBay. Now, he's at the helm of Breather, the company providing flexible workspaces that are as easy to book as an Uber. Breather has expanded to more than 10 cities to date and is poised to grow even faster as commercial real estate evolves in a post-Covid world. Bryan shares how he quickly put together a "get back to work" task force, why he believes crises accelerate disruption, and the importance of being a leader in service to your team.

Chriselle Lim built a fashion empire—replete with a YouTube channel that has gotten more than 29 million views, a collection at Nordstrom that sold out in 48 hours, and a Barbie modeled after her. But after becoming a mom, she realized how hard it was to be present both at work and as a parent. Now, she's the co-founder of Bumo, the startup working to make parenting easier. Chriselle shares her vision for co-locating work and daycare, how she navigated the challenge of convincing investors that she was ready to do something new, and why flexibility is the most important trait of startup employees.

At age 7, he learned to code. At 12, he started his first company. Now, 19-year-old Shane Curran is working to make data privacy simple and accessible for everyone through his startup Evervault. With seed funding from the likes of Sequoia and Kleiner Perkins, the Dublin-based entrepreneur is poised to be a major player in the future of safety on the internet. Shane shares why he believes privacy is a fundamental right, how he learned to interview despite never having held a job before, and why the best founders embrace the macro over the micro.

Austen spotted a major disconnect: a labor market in need of specialized talent and inaccessible education programs to train future employees. Enter Lambda School, a fully remote tech school with Income Share Agreements (ISAs) at its center. Rather than pay up front, students pay a portion of their income after they're hired. Austen shares how a customer survey led him to a brand-new business model, how growing up in small-town Utah has given him a unique view on scalability, and what it feels like when your role models become your peers.

As a D1 athlete, Will Ahmed became obsessed with the idea of recovery. How do you unlock human performance, and what data would you need to do so? This interest led to the creation of WHOOP, the next gen wearable technology. Will started WHOOP in 2012, immediately after graduating from Harvard College. Since then, he's raised over $100M in funding, saw 7x member growth in the last year alone, and has been worn by the likes of Lebron James and Michael Phelps. Will shares how the product was born out of his own over-training as an athlete, why he believes WHOOP is fundamentally a data company, and why the most important part of being a CEO is figuring out who to listen to—and when. Note: This episode was recorded in early March, just as the Covid-19 outbreak took hold of the U.S. Since then, WHOOP has been leveraging their data to aid in health research.

Armed with a lifelong passion for cosmetics, Marla Beck saw an opportunity to transform the makeup shopping experience. In 1999, she founded Bluemercury, and then went on to scale the company into hundreds of stores and multiple product lines—while surviving several recessions—before being acquired by Macy's in 2015. Marla shares why omnichannel customers are most valuable for retail businesses, how she implemented a radical HR model, why she hires for "skill, will, and fit," and why she believes entrepreneurship isn't about risk-taking—it's about risk management.

From a career as a successful wedding photographer to launching one of the top-five highest-grossing photo apps in the App Store, Joel Flory's trajectory is a noteworthy one. As the co-founder and CEO of VSCO, Joel's work centers on his passion for photography, design, and technology. VSCO went viral from the start: Its first product launch grossed north of $250K in the first 24 hours, and its debut app gained a million followers in the first week. Joel shares how to build something people are willing to pay for, why moving forward is one of VSCO's core values, and why he believes the future will be defined by the "experience economy."

Fifteen years into his career in the self-driving-vehicle industry, Chris Urmson has assembled a team of his own. His vision? To make our roads safer by building the world's driver. With a PhD from Carnegie Mellon's Robotics Institute and experience developing Google's self-driving-car program, Chris partnered with his co-founders in 2017 to launch Aurora. Since then, Aurora has raised over $600M in venture funding and inked partnerships across the auto industry. Chris explains how he drives urgency despite the long road ahead, how to foster diversity of thought, and what he thinks the rollout of autonomous vehicles will look like for the average consumer.

After starting his career as a management consultant, Richie Serna left it all behind to move to San Francisco and learn to code. After sharpening his engineering skills at a startup, Richie took the leap to build one of his own: Finix, a payments infrastructure platform that has raised over $55M to bring payments technology to a wide range of customers. Richie shares how being an engineer helped him build a better product, why fundraising is a combination of running a clear process and lots of pitch practice, and why he's a creature of habit (eating the same meals every day to drive efficiency).

It all started with a crush. Yale student Kevin Tan wanted to gift his crush a smoothie, which led him to the idea for Snackpass: a food app that saves its users time, money, and most importantly, is social. Since launching in 2017, Snackpass reached over 80% penetration on Yale's campus and now has plans to scale to 100 campuses in the next two years. Kevin shares why Snackpass is focused on pick-up over delivery, how the company is transitioning from building a product to building a team, and why the secret to capturing any customer is authenticity.

When you start your career as one of the first employees at Yahoo and go on to launch photo tagging at Facebook, what do you do next? For Doug Hirsch, the answer came from looking around for the most challenging problem to solve next. In 2010, after being quoted an outrageous price for a prescription, he had the idea for GoodRx - a company that now provides millions of Americans with affordable and convenient access to prescription medications. GoodRx is now the #1 rated medical app and has a $2.8 billion valuation. Doug shares why he's obsessed with solving messy problems, the importance of blocking out time each day for thinking, and how he views his career through the lens of wanting to make the world a better place.

In 2006, Brian Halligan and Dharmesh Shah teamed up in Boston to launch Hubspot. Since then, Hubspot has become the leading B2B software for inbound marketing and sales. The company went public in 2014 and continues to grow rapidly, with approx. 70,000 customers today. Along the way, Brian has co-authored two books, is a lecturer at MIT Sloan, and has been named a Top-Rated CEO by Glassdoor four times. Brian shares how he made the switch from delighting prospects to delighting customers, why he believes in being a product-focused org, and why he personally receives a 30+ page 360 degree review to optimize his performance as CEO. Make sure to follow Brian on social at @hubspot and @brian_halligan.

In 2011, Samantha Fishbein came together with two college classmates to start an anonymous website, "Betches Love This." When the site took off, Betches quickly went from a fun project to a meaningful business known for deeply resonating with its massive millennial audience. Today, the Betches empire includes New York Times bestselling books, an e-commerce platform, podcasts, and nearly 7 million instagram followers. Samantha shares why bootstrapping helped the company grow at a steady pace, why positive feedback is critical as a manager, and what makes gen z tick. Make sure to follow Samantha on social at @betches and @sami.

As we all strive to increase our productivity, it's no wonder that productivity startup Notion has taken off. Since co-founder and CEO Ivan Zhao launched a prototype a few years ago, Notion has gained a cult following of over one million users. With a team of less than 30 employees, the company has already achieved a sky-high valuation of $800M. Ivan shares his approach to democratizing software, why he believes engineers are the scribes of our time, and why he moved to Kyoto to reboot the company in its earliest days. Make sure to follow Ivan on social at @notionhq and @ivanhzhao.

In 2010, professional hairstylist Alli Webb had the idea to open a salon with a simple motto: "No cuts, no color, just blowouts." She teamed up with her brother, and Drybar has since become a clear beauty industry leader, with over 130 salons and full suite of products. Now, a long stream of upstarts claim to be "the Drybar of [insert service here]." Alli and Michael share how they found investors who could add value and not just capital, why Michael joined Alli even though he was skeptical about the market fit, and how they've trained thousands of stylists over the last decade. Make sure to follow Alli and Michael on social at @thedrybar @alliwebb and @mdlandau.

The era of cars being our go-to mode of transportation may be behind us. At least, if companies like Lime continue on their trajectories of rapid growth. Since launching in 2017, Lime has revolutionized the first and last mile for people around the world, serving more than 15 million users in just a few short years. Toby shares how growing up in a city of over 20 million people inspired his big idea, how Lime grew 10x last year and achieved profitability in key markets, and why he believes our future cities will be built around people—and not cars. Make sure to follow Toby on social at @lime and @toby.lime.

In today's world, the success or failure of a company is often attributed to its company culture. But what defines culture? That's the question Ben Horowitz sets out to answer in his new book, What You Do Is Who You Are—drawing on key lessons from history and his own experience co-founding Opsware (which sold to HP for $1.6 billion) and venture firm Andreessen Horowitz (which counts Airbnb, Lyft, and Slack in its portfolio). Ben shares the two things he looks for in founders before backing them, why culture is how people behave when you're not there, and what prison culture has to do with corporate culture. Make sure to follow Ben on social at @bhorowitz0 and @andreessenhorowitz.

What if 3D printing was 100x faster? That's the big question Dr. Joseph DeSimone posed in his 2015 TED talk, which he gave at the very same moment he unveiled his new company's website. Since then, his company, Carbon, has quickly grown to become the most valuable 3D tech company in the world with a valuation north of $2 billion. Joseph shares how his 20+ years as a professor at UNC lead him to entrepreneurship, what it feels like to have a team counting on you, and how Carbon has achieved an 89 NPS score with the first-ever manufacturing product available via subscription. Be sure to follow Joseph on social at @carbon.

Advancements in fintech mean that entrepreneurs are shaking up every aspect of the financial system. Co-founders Everett Cook and Alex Wheldon have just launched their company, Rho, to do exactly that for business banking. They believe a winning formula is a mix of better rates, best-in-class service, and sleek technology. Everett shares why over-communication is key for a strong partnership, how he leverages his Sunday afternoons to make for more productive weeks, and why he believes in hiring employees who have a sense of urgency. Be sure to follow Everett on social at @rhobusiness

What started as a childhood hobby for sisters Danielle and Jodie has turned into a thriving fashion business, Dannijo. Through a commitment to scrappiness and a knack for marketing via ever-evolving social media channels, Dannijo has managed to stay relevant to its community of super fans for over a decade. Danielle and Jodie share how getting fired gave them the courage to launch, how they put their sisterhood aside in pursuit of a strong business partnership, and why the retail experience needs to be rebuilt from the ground up. Be sure to follow Danielle and Jodi on social at @dannijo, @danielleasnyder, and @jodiesnydermorel.

Money is an inherently emotional topic—and the emotions it tends to inspire are anxiety and fear. Jason Brown is working to change that through Tally. With empathy ingrained in its company culture, Tally now manages more than $400M of consumer credit card debt, and counting. Jason shares why he gets his best ideas on a weekly 60 mile bike ride, the importance of finding an investor who's aligned to your mission, and how he's scaling the business while maintaining a sky-high retention rate. Follow Jason on social at @meettally and on Twitter at @SF_JCB.