Inspired with Alexa von Tobel

Over the course of her career, Divya Gokulnath has gone from teacher to cofounder of the world's largest edtech company. In 2011, she co-founded BYJU'S with her husband, Byju Raveendran, to create a world where every student can learn better. By harnessing technology, BYJU'S has scaled to educate over 150 million students around the world, and the company has become India's most valuable startup. Divya shares why her biggest strength comes from starting as a teacher, how BYJU'S assesses every acquisition through three specific parameters, and why being the founder of a hyper-growth company is like being "an elephant with wings."

John Berkowitz's default is to be in problem-solving mode. So after selling his first company Yodle for $340 million, he was ready to get back in the ring. In 2015, John started OJO, an industry-leading real estate technology company that partners with the top real estate teams and agents to deliver value for millions of consumers. OJO was early to use AI to help people navigate the world of real estate. John shares how the company delivers personalization at scale, why it's important to stay curious, and why he treats OJO as a family business and considers his wife and four kids as an extension of his executive team.

Over lunch with a nurse friend, Heather Hasson realized that the whole experience of buying scrubs—from the shopping process to product quality—was subpar. So she and co-founder Trina Spear set out to create a direct-to-consumer brand dedicated to modern healthcare professionals: FIGS. They went from selling scrubs out of a car in 2013 to going public in 2021 at a valuation of over $5 billion. FIGS was the first company led by two female co-founders to ever be taken public. Trina shares how the company quickly pivoted during Covid to produce protective gear, how leading a public company forces improvements in areas that are not working, and what she learned from her first job as a waitress at Johnny Rockets.

What if lawyers could work 10x more efficiently? That's the problem Jason Boehmig set out to solve in 2014 at Ironclad, a leading legal software provider that helps businesses create and manage contracts. But as AI's capabilities have grown, Jason now has his sights set on making legal work 1,000x more efficient. Jason transitioned from corporate attorney to founder, and Ironclad now has over 1,000 customers and a $3.2 billion valuation. Jason shares why Ironclad invested in the legal community early on, how the company is closing the "access to justice gap," and why he starts off every year by reading a poem to the whole company.

Today, Webflow is a company valued at over $4 billion. But it took Vlad and his cofounders repeated attempts to get the company off the ground. In 2012, they started gaining steam for their vision to allow people to create websites with no coding experience. The company now brings the power of software engineering to designers through an intuitive visual interface and has grown to over 3.5 million users. Vlad shares how Webflow has made its user community a superpower, why having two kids when he started the company gave him extra motivation to succeed, and how he predicts no-code and generative AI will intersect.

While in business school, Jeff Raider co-founded Warby Parker and watched the iconic glasses company take off. So when his friend, Andy Katz-Mayfield, G-chatted him one day with an idea to reimagine mens' razors, Jeff was intrigued. In 2013, the duo started Harry's to create exceptional shaving and personal care products that better meet the needs of modern men. The company has since reached tens of millions of people and become the #2 men's shave brand in the country. Jeff shares how they signed on a German factory to manufacture a million blades before writing a business plan, how their first referral program led to over 100,000 email sign-ups in a week, and how he found the silver lining when the FTC blocked a planned acquisition of Harry's in 2020.

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.

In 2009, Tim Chen found himself laid off from his Wall Street job and was trying to figure out his next move. But a simple question from his sister about finding the right credit card turned into the core idea for NerdWallet, the company on a mission to give consumers clarity around all of life's financial decisions. NerdWallet started as a tool to help people shop for credit cards, but has scaled to serve over 19 million users. In 2021, Tim led NerdWallet through an IPO. Tim shares why they raised venture capital only after the company was profitable, why he loves the Jeff Bezos quote that very few decisions are irreversible, and how his parents instilled Tim's entrepreneurial drive.

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)

Just a year into medical school at Harvard, Sean Duffy decided to pursue a new route toward healthcare delivery. In 2011, he started Omada Health to explore how design and technology could make a difference in healthcare. Today, Omada Health is a virtual-first care provider that blends clinical protocols with behavior science to help people with chronic conditions achieve long term improvements. The company now serves over 700,000 members and has facilitated over 13 million messages between members and care teams. Sean shares why Omada chose to focus on in-between-visit care, how the pandemic accelerated digital adoption by a matter of years, and why his most helpful read as he started a company was The Entrepreneur's Guide to Business Law.

Today, millions of users know Noom as the most-installed weight loss app of 2020. But it took countless pivots and many years for the consumer-led digital health company to turn its mission—of helping people live healthier, happier lives—into a product users are obsessed with. Saeju's intense desire to help people dates back to childhood in South Korea, growing up in a family of doctors. He started working on what would become Noom in 2007, but it took nearly a decade for the company to hit its stride. Saeju shares why he's hyper-focused on preventative healthcare, why he would have been shocked as an early founder to learn he'd be in the weight loss business, and how becoming a father made him realize the value of his parents' unconditional love.

Harley Finkelstein first encountered Shopify as a user. Back in 2006, while in law school, he was one of the first merchants to use the platform. He joined the company in 2010 and now serves as President, helping to scale Shopify to millions of daily active users across 175 countries driving $444B in global economic activity. Today, Shopify is the all-in-one commerce platform to start, run, and grow a business—and is second only to Amazon as the largest online retailer in the US. Harley shares why the future of e-commerce is just the future of commerce, why his favorite motto is "how you do anything is how you do everything," and how being a power extrovert has made him a stronger leader.

It has been nearly two decades since Sebastian Siemiatkowski started Klarna, based on the simple idea of enabling customers to pay how they'd like. Today, Klarna is a fintech giant on a mission to revolutionize the retail banking industry. Headquartered in Sweden, Klarna is now a fully licensed bank operating across 45 markets. The company has scaled to over 150 million active consumers and over 450,000 merchant partners. Sebastian shares why he thinks of Klarna as a digital assistant that saves people time and money, why he thinks the banking industry will shrink (making Klarna a larger player in a smaller industry), and how growing up as a Polish immigrant in Sweden gave him a hunger for entrepreneurship.

How do retailers find brands to feature in their stores? For years, trade shows were the default option. Until Faire entered the scene. Max Rhodes started Faire in 2017 as an online marketplace where retailers discover their next bestsellers from independent brands across the globe. Today, the company supports over half a million retailers in 15,000 cities and connects them to over 70,000 brands around the world--earning the company a $12B valuation. Max shares what it felt like when he realized Faire had reached product-market fit, why he thinks solely direct-to-consumer brands will go away, and why being a college athlete at Yale felt like entering the working world four years early.

Amidst a fintech boom over the past decade, Acorns has continued to scale dramatically. The app which allows consumers to save and invest has grown to serve over 11 million customers and has helped its users invest over $15 billion to date. Noah's path into the CEO seat was an unusual one: he's a 4x entrepreneur and former DJ for Jennifer Lopez. But growing up in New York City gave him a life and career purpose to help level the playing field. Noah shares how he thinks of Acorns as a financial wellness system, why behavioral economics have helped the company make an emotional connection with users, and why he's inspired by the quote "the process is the prize."

Three years after the first human genome was sequenced, Anne Wojcicki cofounded 23andMe. After a decade on Wall Street investing in healthcare, Anne started a new career chapter as a founder working to empower people with direct access to genetic information. Fast-forward and 23andMe has become the only personal genetic test with FDA authorization to deliver health information directly to consumers. To date, over 12 million people have taken a 23andMe DNA test kit. Anne shares why she adopted a low-margin and high-volume business strategy, why she believes personalized medicine is the future, and how figuring out time management was one of her biggest hurdles.

As an expert in global payroll and global workforce management, it was only a matter of time before Eynat took the leap to close the industry's technology gap. In 2016, she started a revolution in global payroll management when she co-founded Papaya Global. As the pandemic accelerated the growth of global teams, Papaya has scaled to work with over 700 companies, managing over $3B in total payroll. Eynat shares how customer discovery sessions impacted Papaya's product roadmap, why she believes in worst-case-scenario planning, and why she stayed the course with an aggressive growth plan in 2020.

In 2012, as a Ruby programmer, Sid Sijbrandij encountered GitLab, an open source technology that sparked his interest. Soon after, he decided to build a company on top of GitLab and has since scaled the DevOps platform to an estimated 30 million+ registered users from startups to global enterprises alike. A decade after the first GitLab code was written, the company went public at a valuation of $11B. Sid shares how their pricing model is based on end user, the value of starting a CEO shadow program, and why he decided to make the company's 2,000 page employee handbook public.

In 2007, Emmett co-founded a live streaming service called Justin.tv along with his childhood friend and neighbor, Justin. That first entrepreneurial spark grew into Twitch, an interactive livestreaming service that spans gaming, entertainment, sports, music, and more. Today, at any given moment, more than 2.5 million people globally are engaging with Twitch. While Twitch was acquired by Amazon in 2014 for nearly $1 billion, Emmett has stayed on as CEO and continued to scale. Emmett shares why the company's hardest engineering challenge was scaling live video, why the future of the creator economy is "micro-patronage," and the role Twitch plays in combating loneliness.

When repeat founder Brian Long set out to build a text communication platform for businesses, he soon realized that the first version of his product didn't have the market pull he was looking for. After a pivot, Brian found himself building Attentive, the comprehensive mobile messaging platform for brands. Six years in, Attentive has become a major player in the e-commerce space and counts thousands of major brands as customers, from CB2 to Michaels. On average, Attentive drives 20% of total online revenue for its customers. Brian shares how he managed hypergrowth in 2020 as customers grew by 270%, why he always asks for quantitative feedback in every customer conversation, and why his unusual trick to destress at work is through reading World War II books.

Throughout his career, Dan worked at tech giants Amazon, Microsoft, and Google. In 2015, he set out to build a tech giant of his own: Convoy. Convoy is a digital trucking network that is transforming the trillion-dollar global trucking industry. Dan went from interviewing truckers on the side of the road to building a business that works with over 300,000 trucks across the country. Dan shares how the rise of mobile technology was an accelerant to his business, how he used YouTube to learn the language of trucking, and the pivotal advice Jeff Bezos gave him about building a leadership team.

Today, millions of homes across the country have installed solar panels. But that was not the case when Ed Fenster co-founded Sunrun in 2007. Since starting the company with his business school classmate, Sunrun has grown to become the leading home solar and storage company. Ed is driven by a deep mission to power the planet through the sun, and Sunrun, which went public in 2015, now operates in 23 states. Ed shares how he recognized a huge opportunity on the residential side of the market, how his successful business partnership was fueled by an alignment in ethics and decision-making, and why his secret to unwinding is playing blues piano.

In 2009, Adi and her husband Alon Cohen embarked on a home renovation. They quickly realized how challenging it was to find both inspiration and qualified home professionals, so they started a side project to bring technology into the home design space. Organically, the Houzz community blossomed to hundreds of thousands of users before Adi decided to take on outside capital and make Houzz her day job. Today, Houzz is the leading platform for home renovation and design and has over 65 million users. Adi shares how she overcame knowing no one when she first moved to Silicon Valley, how she built a thriving two-sided marketplace through word of mouth, and why she loves building the company alongside her husband.

In 2010, over a sushi dinner with a friend, Jason sparked an interest in what would become his next entrepreneurial adventure: transforming modern card issuing. With a deep intellectual curiosity for how credit cards work, Jason built Marqeta to bring game-changing card products into the world. Marqeta now works with customers in 39 countries, has a team of nearly 900 employees, and IPOed in 2021. Jason shares how he almost moved to Australia to start a Jamba Juice-style chain before Marqeta, how he persevered after nearly running out of money in 2015, and why he's fueled by the challenge of people not believing in him.

Family farmers, who are the backbone of the food and agricultural system globally, represent fast-growing small businesses looking to innovate. That's why Amol Deshpande left his career as an investor to start Farmers Business Network (FBN), the global farmer-to-farmer network and agtech company. FBN is on a mission to power the prosperity of family farmers around the world and now supports over 43,000 farmers responsible for over 80 million acres in the U.S., Canada, and Australia. Amol shares why—despite the stereotype—farmers are tech-forward, how his upbringing instilled an appetite for risk-taking, and why it's critical to invest time with your children consistently, just as you show up consistently at work.

In 2011, Jay Kreps was an engineer at LinkedIn, leading the platform's search, recommendation engine, and social graph. In an effort to figure out how to make real-time streams of data useful to organizations, he started an open-source project called Kafka, and it took off. Realizing a major business opportunity, Jay took the leap into entrepreneurship and started Confluent in 2014. Today, over 70% of Fortune 500 companies use Kafka, and he took Confluent public in 2021. Jay shares what it means to process "data in motion," why it's daunting to go from being a software engineer to CEO, and why he only spent one year in a traditional high school before deciding to teach himself.

Growing up in Alabama, Josh Tetrick dreamed of being an NFL player. But when that dream didn't come true, he set his sights on a wholly new endeavor: to make a better version of an egg. He started Eat Just, a food technology company working to build a healthier and more sustainable food system. Since then, Eat Just has created America’s fastest-growing egg brand, which is made entirely of plants, and the world’s first-to-market meat made from animal cells. Josh shares how he got his plant-based eggs into nearly every major retailer, how he's overcome the challenge of scaling from a lab to national distribution, and why thinking about death helps him frame the urgency of his priorities.

In 2019, with a belief that work was becoming increasingly borderless, Alex Bouaziz and his cofounder Shuo Wang started Deel. They built a global compliance and payroll solution that helps businesses hire anyone in over 150 countries. Fueled by a shift to distributed work unlocked by the pandemic, Deel has experienced unprecedented growth: the company has raised over $600M in funding, scaled to over $100M in ARR, and now has over 1,000 employees in 75 different countries. Alex shares why he holds two KPIs sacred (monthly growth and customer satisfaction), the importance of keeping money in the bank and spending like you're a round earlier, and why larger companies are beginning to think more about output than input.

If you've heard of NFTs (non-fungible tokens), it's likely thanks to the work of Roham Gharegozlou. Roham is the Co-Founder and CEO of Dapper Labs, the NFT company that has created some of the most viral brands out there, from CryptoKitties to NBA Top Shot. Through his venture studio Axiom Zen, he started looking into crypto back in 2014. With a mission to bring play to crypto, Dapper Labs has been named one of the most innovative gaming companies by Fast Company and has created some of the most broadly used applications in the history of crypto. Roham shares how NBA Top Shot scaled to over one million users, why he thinks of NFTs as the next evolution of social media, and why entrepreneurship requires a healthy balance of optimism and paranoia.

In 2011, when Pat Brown took a sabbatical from his position as a biochemistry professor at Stanford, he had already spent decades making a positive mark on the world. He had developed a technology that made it possible to monitor the activity of all the genes in a genome, a huge development in cancer research. But during his sabbatical he decided to address the environmental impact of animal farming. Enter Impossible Foods, which is now available in thousands of grocery stores and restaurants across the country. Pat shares why he's on a mission to completely replace the use of animals in food technology by 2035, why their initial go-to-market strategy centered on top chefs, and how trail running and large amounts of coffee fuel his entrepreneurial journey.

While working at a small sales intelligence firm in Las Vegas, Henry saw an opportunity to leverage technology to unlock opportunity for go-to-market teams. In 2007, he started DiscoverOrg from his law school dorm. Brick by brick, he scaled DiscoverOrg, leading the company through 11 acquisitions (including of Zoom Information, from which the business takes its name). Thirteen years after founding the company, ZoomInfo became the first tech company to go public during the Covid-19 pandemic. Henry shares why he believes in the American dream, what it was like to take a company public in a fully remote environment, and why the practice of gratitude journaling makes him a better founder.

As a serial cybersecurity entrepreneur and operator, Michael found himself investigating a $200M bitcoin hack that happened in 2017. As he dug into it, he realized there was a big opportunity to help companies manage digital assets securely. In 2018, he co-founded Fireblocks, the leader in digital assets and cryptocurrency custody, transfer, and issuance technology—or in Michael's words, "Shopify for crypto." Fireblocks now works with over 1,200 financial institutions and supports over 850 tokens. Michael shares how Fireblocks built up a referral network that drives a third of inbound inquiries, how serving on an elite military technological unit gave him a refuse-to-lose mentality, and why he believes NFTs will transform how people do business on the internet.

What does it take to grow a company from zero to over $10 billion of value in just five years? In the case of Nikil Viswanathan's Alchemy, the answer comes down to speed and hustle. Nikil and his cofounder are both Stanford-educated serial entrepreneurs who set out to build a company that would change the world. They see web3 as a major paradigm shift and business opportunity, and the duo has scaled Alchemy into the world's leading blockchain developer platform (think: Microsoft for web3). Nikil shares why 22 of the company's first 27 hires were former founders, why he believes NFTs will be the first web3 iteration to be mass-market friendly, and why he and his cofounder celebrate big wins with a trip to the gym.

How did Didier Elzinga go from CEO of an Academy-Award winning visual effects company to tech founder of the world's leading employee experience platform? Spoiler: it's all about the people. In his first CEO role, Didier realized that people were everything and that his role was primarily focused on people management. So in 2009, he set out to create a better world of work. Since then, Culture Amp has scaled to work with more than 5,000 companies and 25 million employees across the globe. Didier shares why he believes in the transformative power of story, how the importance of communication ramps up during periods of hyper-growth, and why post-Covid offices must facilitate a different way of bringing people together.

A three-time entrepreneur and seasoned product leader, Todd Olson is on a journey to build software that makes software better. At Pendo, his Raleigh-based company, he's helped over 2,300 customers—from Salesforce to Toast—build product-led organizations. Nearly a decade into building Pendo, Todd feels he's finally found the entrepreneurial success he's been striving for throughout his career. Todd shares how he got his first customers through community-driven events, why companies should have separate product and engineering leaders, and how he incorporates his family into the company, often cooking for investors and customers in his home.

With the rise of fintech apps, consumers find themselves with accounts scattered across institutions and brands. But what if there was one financial superapp that functioned on a global scale? Enter Revolut, the company Nik Storonsky co-founded in 2015 that is transforming the way we do all things money. The app has seen exponential growth with more than 18 million customers across 35 countries, earning it a valuation over $33B. Nik shares how the company went from a single card product to a one-stop financial solution, how a great product scaled the company entirely by word of mouth for the first five years, and why the secret to his management philosophy is rooted in the math of hiring exceptional people.

When a consumer adds an AppleCare warranty to their purchase, it adds a layer of trust and protection. What if you could insure most purchases you make online? In 2019, Woody Levin co-founded Extend to modernize the warranty industry. As Covid accelerated the e-commerce, Extend's business has seen rapid growth, working with customers from Sur La Table to Peloton. Woody shares how his aha moment for Extend came from losing a fantasy football bet, why it was like to hire 350 employees in one year, and how he's used career failures as fuel.

In 2015, Ariel co-founded TripActions to transform business travel. In the classic Blockbuster vs. Netflix analogy, TripActions set out to be the latter—replacing travel agents and complex expense reports with a best-in-class digital experience. The company's tremendous growth came to a screeching halt in 2020, when Covid stopped business travel altogether. But TripActions adapted and came back even stronger, now boasting over 9,000 customers and a valuation north of $7B. Ariel shares how a disastrous business trip to Ukraine was one of his aha moments, what it was like to lose all revenue in a two-day span when the pandemic hit, and why distributed teams have now unlocked a new category of business travel.

When Kate Ryder founded Maven in 2014, to reimagine healthcare for women and families from the ground up, she was ahead of the curve. With virtual care delivery at its core, she's grown Maven into the largest telehealth network for women's and family health globally. Maven's growth started with a "boots on the ground" marketing strategy and was accelerated in recent years by Covid. Today, the company has a thriving B2B model that supports over 10 million families in 175 countries. Kate shares why her earlier career as a journalist makes her a stronger founder, how summers in the Adirondacks sparked her imagination and self-reliance, and how she created a new category in healthcare to fill in all the moments outside of the doctor's office.

To build one successful company is a major achievement—particularly in an industry as complex as healthcare delivery. But Glen Tullman has done it time and time again. He digitized electronic prescriptions, led a hospital resource management company, and built the first at-scale digital health company to empower people with chronic conditions. He led his last company, Livongo, through the largest consumer digital health IPO in history. With Transcarent, he's back in the CEO seat, building a better healthcare experience for employees of self-insured companies. Glen shares why "telehealth" should just be called "health," why he'd rather be building a business than sleeping, and what role tech players like Apple and Amazon will have in the future of healthcare.