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. 

Sometimes, change starts at the top. Carolyn Childers and Lindsay Kaplan weren't willing to wait to reach gender parity in the workplace, so they started Chief. These startup vets — who helped build Soap.com, Casper, and Handy — have created a community for senior women executives that already has a waitlist in the thousands. Carolyn and Lindsay share how they've built a no-judgement zone, their approach to creating a game-changing brand, and why coaching is critical to the future of work. Make sure to follow Carolyn and Lindsay on social at @childerscarolyn, @lindsaykap, and  @chiefamongstus. 

What if there was a stock market for private companies? Carta is well on its way to realizing that vision. Henry Ward launched the company to 2012 under the name eShares. Fast-forward and Carta now manages over $575B in equity for 11,000+ companies and has a sky-high valuation of its own at $1.7 billion. Henry shares his vision for closing the wealth inequality gap, how he's hiring 50 new employees each month, and how his previous startup's failure led to Carta's success. Check out the full episode in the player below. Make sure to follow Henry on social at @cartainc

In 2012, Max Levchin launched Affirm to give consumers a new way to buy with instant point-of-sale loans. Max is no stranger to transforming financial services—as a co-founder of PayPal, he's been reimagining our relationship to money for decades. Max shares how his quest to build a better FICO score expanded into a broader mission for Affirm, what he learns from listening to customer service calls, why he set out for Palo Alto after college to start "an internet company" (which became PayPal), and reveals his Myers-Briggs type.  Follow Max on social at @affirm and on Twitter at @mlevchin. 

Will the future of retail be decentralized (think: what Uber's done for transportation and Airbnb for lodging)? This entrepreneur thinks so. Eric shares how Storr is enabling anyone to monetize their style by opening a digital store in just three clicks, why he started by researching the history of retail (all the way back to the 1800s), and how he got creative to sign his first brand partners before raising seed funding. 

While insurance is a $5 trillion dollar market, Daniel noticed an opportunity: most insurance companies are not described as lovable or delightful. He wants consumers to forget everything they know about insurance and start fresh. Daniel shares how Lemonade leverages technology to build trust, how they've achieved an NPS of 70+, and why keeping Shabbat each week helps him set healthy boundaries as a founder. 

70% of American employees work in open floor plan offices—and according to Brian Chen, they don't like it. Brian and his cofounders set out to reimagine the modern workplace and launched their first product, an office phone booth (which already graces the offices of Google, Apple, and J.P. Morgan). Brian shares his own frustration with not being able to find a quiet space at work, explains how he and his co-founder personally delivered and assembled their first prototypes, and why they care about being responsible citizens of the world. 

Bobbi Brown began her career as a freelance makeup artist. She didn't set out to build a billion dollar makeup business, but she quickly accelerated from creating a line of lipsticks to an acquisition by Estee Lauder four years later. Bobbi went on to spend nearly two decades building Bobbi Brown into a household name. Bobbi shares how she adapted to being a corporate employee post-acquisition, why being able to wear jeans to work matters, and how she interviews for work ethic.

Aaron Levie dropped out of college and moved into his uncle's garage to launch Box. Fast-forward and the company has 95,000 enterprise customers and a $3 billion market cap. While one of his first win's was securing an investment from Mark Cuban off of a cold email, it wasn't always an easy journey. Aaron shares how he zeroed in on the right business model, how he hires for culture adds, and why startups have to be 10X better in some way (like simplicity). 

Justin McLeod has an unusual mission: build a dating app designed to be deleted. It was his own offline love story that helped him gain clarity into his vision for Hinge and guided the company through a critical pivot. Justin shares what it was like to be acquired by the Match Group, why he thinks social media is the new smoking, and how to know when a new business strategy is working. 

From the time she was a teen, Misha Nonoo dreamed of becoming a fashion designer. She has since grown her women's apparel company into a powerhouse that constantly stays ahead of seismic shifts in the retail landscape. Misha shares why she forewent the wholesale model to gain a direct relationship with her customer, why sustainability is critical to the future of fashion, and why discipline is the most important trait for entrepreneurs to embody (and to hire for). 

After meeting as freshmen at Georgetown, Jonathan and his two-cofounders set out to open a healthy fast food restaurant in a 500 square feet storefront. From those quaint beginnings, Sweetgreen has grown into a massive food platform, with over 100+ locations and 200+ outposts. Jonathan shares why authenticity is core to the brand, why their inexperience actually enabled innovation, and how he thinks about falling on the right side of this equation: as companies get bigger, they either get better or worse.

From her parents' house to two million+ monthly readers, Leandra has built a media business at the forefront of fashion. With a firm belief that quality content should drive all, the Man Repeller team has grown to over twenty employees and continues to innovate into new lines of business. Leandra shares the blessings (and curses) of building a brand on social media, why creativity is a key ingredient for a great day at work, and the difference between being a good leader and a good boss. 

Susan started Framebridge out of a personal paint point: she tried to frame a series of National Parks posters and realized the process was both confusing and expensive. With $82 million in funding and a major facility in Kentucky, Framebridge has fundamentally transformed the experience for consumers across the country. Susan shares why she always does the hard thing first, the challenge of managing seasonal spikes in business, and how she doesn't waste time on guilt as a working parent.

There's something about sneakers. It's one of those rare product categories that can get people to line up around the block. GOAT has made a huge dent in the sneaker scene, building a managed marketplace that currently lists over 1 million sneakers. Eddy shares how GOAT authenticates the product moving across their platform, how he thinks about online vs. retail sales, and what it was like to acquire a sneaker pioneer as a new upstart.

Shan-Lyn Ma is transforming the wedding business. After graduating from Stanford Business School and joining Gilt as their first product person, Shan launched Zola in 2013—and has already helped over half a million couples. Shan shares why product is so important to every business, how to get smart (and actionable!) consumer feedback, and the real story behind Zola's creative name.

Mattress shopping never sparked joy — until Casper came around. Philip and his coworkers have upended the industry and now have a $1.1 billion dollar valuation. Philip shares his vision for the future of sleep, how to scale a brand (both digitally and in retail experiences), how he thinks about the competition, and tells us about the synchronous run-in at a co-working space that led to Casper.

After working for 8 years as a Wall Street Journal reporter, Jessica set out to build a new content model - a subscription business founded on a simple premise: create articles worth paying for. Jessica shares why she became an entrepreneur, how she learned to make decisions quickly, and how content consumption will evolve over the next decade. 

Umbrella is on a unique mission: the startup is aiming to help people 65+ stay in their homes longer. The demographic they serve is not only one of the fastest-growing, it's also an audience that avidly uses tech. Lindsay shares what excites her about the market opportunity, how product testing uncovered key wins, and most importantly, how she makes it work with her cofounder, Sam Gerstenzang.

Chances are, you've experienced Danny Meyer's brilliance. He's the founder behind Union Square Hospitality Group, which holds a remarkable 28 James Beard awards and is responsible for Shake Shack, which now has over 250 locations worldwide. Meyer opens up about what he looks for in new hires, how he took the leap into the food world, and shares his scariest moment to date (spoiler: getting punched in the face by a diner).

Brynn Putnam is no stranger to building businesses. In 2010, she started Refine Method, the award-winning boutique fitness studio. Now, she's the Founder & CEO of MIRROR, tapping into the $14 billion dollar home fitness market with a connected fitness system that streams classes to users in-home, all via (you guessed it) a mirror. Putnam shares how she came up with the idea and built her first prototype, the surprising range of users who love the platform, and how her professional dancing career makes her a stronger CEO.

Founder of Airtable, Howie Liu, built his first company at age 20 and sold it to Salesforce just a year later. The second time around, he's built a new platform that's already valued at over a billion dollars, putting Airtable in the rarified group of unicorn tech companies. Liu shares how he's found success via a slow and steady approach, his aspirations to become the next great tech company, and why he prefers farming metaphors to the wartime ones so often used by entrepreneurs.