Inspired with Alexa von Tobel

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.