S2E6: Expensify CEO David Barrett on Telling 10 Million Customers to Vote for Joe Biden

Many founders and investors talk about being mission-driven, but Eren Bali truly walks the walk. He's created two separate companies that have had a dramatic impact on increasing access to vital services. He co-founded and served as the CEO of Udemy, a $3B+ online education company, before creating Carbon Health. Carbon Health makes world-class healthcare personal and accessible by bringing technology into the workflow of digital and in-person primary care. Carbon Health just recently closed on a Series C funding of $100 million after expanding from seven states to twenty-seven states in under twelve months. In this episode, Eren shares his journey from an underprivileged upbringing in the mountains of Turkey to creating leading Silicon Valley companies expanding access to education with Udemy and healthcare with Carbon Health. Don't miss it!

Ruben Harris wants you to succeed. Like other guests on The Operators, he left behind a successful career in finance to build a company that helps people. For Ruben, this came in the form of Career Karma, the #1 destination for career advice, and the easiest way to find a job training program. Bridging the gap between education programs that need candidates and prospective students that don't know where to start, Career Karma makes education accessible practically and effectively. Ruben is also the host of the wildly successful podcast Breaking Into Startups, a show about getting into tech from non-traditional backgrounds.  In this episode, he gets into the details of who to pitch, how to talk about your startup, and how Career Karma has raised each of its financings, including getting into YCombinator and raising a Series A from Initialized Capital.

On The Operators, we talk a lot about aligning passion and strategy. Alyson Friedensohn Watson embodies this alignment. Alyson knew that she cared deeply about de-stigmatizing mental health and increasing access to it, but she found a way to turn this passion into a multi-million dollar company: she founded Modern Health, which today announced their Series C funding of $51M dollars led by Battery Ventues with other investors including Felicis Ventures, Kleiner Perkins, and Founders Fund. By implementing mental health resources as a health benefit and preventative measure in corporate settings, Alyson's work has revolutionized the way folks talk about these issues and the way they access this kind of care. Modern Health's clients already include the likes of Pixar, Gusto, Cliff Bar, Lyft, SoFi, and Nextdoor, as they continue their quest to improve access to care and attitudes around mental health for all Americans. Take a listen to hear how she and her team have built Modern Health, one connection at a time.

Rohan Pavuluri isn't even 25, but he's a CEO, one of Forbes' "30 under 30" in Law & Policy, and the creator of a TIME 2020 "Top 100 Inventions of the Year." From his endearing start in local politics while in high school to developing his now-famous nonprofit during a summer off from Harvard, Rohan is a rising advocate for important societal change. He created Upsolve with a specific goal in mind: help low-income Americans navigate bankruptcy without the burden of hiring a lawyer. In its 4 years, Upsolve has already relieved almost $300 million dollars in debt, allowing struggling people earn a fresh start. Rohan's company has directly changed millions of lives by pushing the belief that people aren't defined by their credit scores - a radical and impactful shift in the world of personal finance. 

One week before the presidential election, Expensify founder and CEO David Barrett made a decision that ultimately landed him in the headlines of Bloomberg, CBS News, Business Insider, etc. He sent an email urging all Expensify customers to vote for Joe Biden, stating directly that a vote against Biden is a 'vote against democracy.'  Given that Expensify sells expense management software, it was a shock for customers and investors alike when 10 million people received emails with such an overtly political message. On election day last week, Neil sat down with David to talk over this bold decision, the creation of his company, and the complex relationship between business and politics. 

On this week's episode of The Operators, Neil sits down with Founder & CEO of Tempest Holly Whitaker. Holly never planned on starting her own company, but out of her battle with addiction came her calling to create Tempest. Breaking the typical rules of both entrepreneurship and sober living, Holly details her complex journey of raising almost $20M in venture capital for Tempest, ultimately helping so many in their battles with addiction.

Where would we be without Quizlet? If you've gone to school in the last ten years, this tool has probably saved your life. In this episode of The Operators, we hear how Andrew launched this iconic startup when he was just 15 years old, the early days of the company, and his passion for education reform. Take a listen to hear how one of only a handful of $1B+  educational technology startups has been built from the ground up. With the election coming up, we will be taking a break for the next two weeks. We'll see you in November, and don't forget to vote!

Shivani Siroya built her first career as a strong performer in high-end finance job, but some part of her was craving a more impactful path. In an industry that errs on the side of caution - especially when it comes to lending to low-income borrowers - Shivani began asking,  "how can we better extend trust to more people?" With almost half of the global population unable to participate in the formal financial system, Shivani realized that so many people were left behind simply because of where they were born. She came up with a brilliant solution to a seemingly impossible problem: lending to users who lacked a meaningful credit history or involvement in the formal financial system. All that's needed is a mobile phone to underwrite, originate, and collect on microloans.  These microloans, which range from $100 to $500, drive massive impact for borrowers by enabling them to start new businesses, attain new educational opportunities, and have a stopgap for emergencies. With offices in India, Mexico, the Philippines, and Kenya, Tala now serves millions of borrowers with life-changing loans every single day.  Take a listen to Shivani's fascinating journey to hear about her experiences in starting and building Tala.

Adam Jackson has founded multiple successful companies, including Doctor On Demand with Jay McGraw (the Executive Producer and Creator of The Doctors) and Phil McGraw aka Dr. Phil. He's also a successful investor with investments like SuperHuman, Zenefits, and Bolt.  Despite all his success and experience, Adam believes that how we work is broken. Current structures inhibit employees from having enough control over their own work. Adam shares with us his journeys through entrepreneurship and how his company Braintrust is giving control back to workers. Take a listen to hear about how Adam created the world’s first user-controlled talent platform, his early days as a startup founder, and his passion for meaningful entrepreneurship.

Mondaire Jones is not your typical politician. Despite being raised in Section 8 housing and on food stamps by a single mother working multiple, Mondaire made it to Stanford for college and Harvard for law school before working for President Obama and the Legal Aid Society. Since then, he's decided to run for Congress, winning his party's nomination as a young, gay, black progressive in a mostly white and wealthy district in New York. As he heads toward the general election next month, Mondaire sat down with Neil to talk about his "dialing for dollars" fundraising, winning endorsements from Bernie Sanders, the New York Times, and Elizabeth Warren, and his goal of becoming the first black, LGBTQ+ member of congress.