Skip to main content
The Operators

The Operators

By Neil Devani
Starting your own company? Finally ready to make that big change?

There’s so much to learn but so little time. The Operators brings you insights on success, whether you’re building a company or a career.

Our guests are execs with operational experience at both fast-rising startups, like Brex, Calm, DocSend, and Zeus Living, and more established companies, like AirBnB, Facebook, Google, and Uber.

Listen in as they share strategies and tactics for building your first a company and charting your career in tech.
Where to listen
Apple Podcasts Logo

Apple Podcasts

Google Podcasts Logo

Google Podcasts

Overcast Logo


PodBean Logo


RadioPublic Logo


Spotify Logo


S2E10: Healthcare and Education for All: Eren Bali on creating Carbon Health and Udemy
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!
December 22, 2020
S2E9: How Ruben Harris "Broke Into Startups" and Raised Career Karma's Series A
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.
December 17, 2020
S2E8: How Modern Health Founder Alyson Friedensohn Watson Raised $95M to Make Mental Health Mainstream
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.
December 15, 2020
S2E7: Rohan Pavuluri on creating Upsolve, one of TIME's "Top 100 Inventions of the Year"
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. 
November 19, 2020
S2E6: Expensify CEO David Barrett on Telling 10 Million Customers to Vote for Joe Biden
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. 
November 12, 2020
S2E5: It's Personal: Addiction, Sobriety and Multi-Million Dollar Entrepreneurship with Tempest CEO Holly Whitaker
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.
October 29, 2020
S2E4: How Andrew Sutherland Created an Ed Tech Unicorn with Quizlet (and saved your GPA)
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!
October 22, 2020
S2E3: How Shivani Siroya Raised $200M+ to Change Her Customers' Lives
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.
October 15, 2020
S2E2: From Raising Over $100M to Change Healthcare to Empowering Workers with Blockchain: learning from Adam Jackson @ Braintrust
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.
October 08, 2020
S2E1: Endorsed by Bernie Sanders, the New York Times, and Elizabeth Warren: Who is Mondaire Jones?
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.
October 01, 2020
S1E10: Hustle CEO Sam Parr & SmartNews Chief Journalist Rich Jaroslavsky on the Future of Media
In this episode, you’ll hear from Sam Parr, the co-founder and CEO of The Hustle, one of the fastest-growing email newsletters, along with Rich Jaroslavsky, the Vice President of Content and Chief Journalist at SmartNews, a news aggregation startup that recently achieved a unicorn valuation.   Our discussion touched on some of the most important questions in digital media: What opportunities are there for new media entrants How it is impossible to start a successful media company today without having a strong grasp of how technology can be leveraged How the hardest problems in media today center around distribution and monetization Why content creation is actually one of the easier problems to address How increasingly the medium is the message: the iPhone changed media consumption and increasingly it looks like how we consume audio is changing the delivery of media, consumption, and monetization An analysis on the current state of media and their predictions on where media is headed Rich Jaroslavsky began his media career as a journalist for the Wall Street Journal before becoming the national political editor as a White House correspondent. He was instrumental in bringing the Wall Street Journal online years ago. For the past 25 years, Rich has been involved in digital news at and Bloomberg and is currently at Smart News, where he is Chief Journalist and the VP of Content. Sam Parr is the co-founder and CEO of The Hustle, a beloved and rapidly growing newsletter, conference convener, and broadening digital media business.
February 23, 2020
S1E9: Growth - What It Is and How To Get It
In this episode, we’re talking about growth. Growth means different things at different companies, but correctly identifying avenues for sustainable and scalable growth is a priority for almost all companies. On this topic, we’ll cover: Defining growth and being good at it Managing growth without losing sight of the big picture How companies should approach growth To learn more, we spoke with two experts in the field of growth: Isaac Silverman began his career as an entrepreneur before joining the team at Zynga to work on growth development. At Zynga, Isaac focused on some of the most cutting-edge approaches to growth and development. He then moved to Postmates where he focused on growth product and is now the head of rider growth at Uber. Matias Honorato is currently a senior manager on the growth team at Tally, a growth-stage tech company, and also brings his own entrepreneurial roots and experience at companies like Earnest and Tradecraft. If you're considering a career in growth or building a company,  you can't afford to miss this episode!
November 20, 2019
S1E8: Recruiting Your First Hires
In this episode, we’re talking about hiring and recruiting, including why people take the risk of working at early-stage startups, when and how to work with recruiters, and how to make your first hires.  A company’s first hires are often the hardest. Money is usually too tight to pay competitive salaries. There’s no recognizable brand or reputation yet, and people more often want to work at a company that their friends and family have heard of before. There’s also fair presumption of risk and unviability. Who wants to take a job that might not be around in a year? Startup founders overcome these odds on a regular basis. To figure out how, we spoke with two experts, Farah and Kelly. Farah Sharghi-Dolatabadi began her career as a software developer and a financial advisor before moving into recruiting. She’s been a recruiter at startups in addition to companies like Google and Lyft. She’s currently a senior technical recruiter at Uber and an active career coach at HireClub. Kelly Kinnard is the Vice President of Talent at Battery Ventures, where she’s worked with startups like Wag, Coupa, Fastly, and Gainsight. She also has experience at top recruiting firms and in executive search at Oracle. If you're going to be doing any hiring in the near future, you can't miss this episode!
November 06, 2019
S1E7: Getting Press for Your Startup and the True Role of Communications in Tech
In this episode, we’re talking about the vast world of communications. Early on, most founders and investors focus on driving positive coverage in the press. If they’re unfortunate or mess up, mitigating negative coverage may end being a goal too. But communications also includes more broadly considering how and what information to share what inside and outside of the company. It touches on domains like management, recruiting, marketing, and business development. It’s basically everywhere. It’s also a highly optimizable domain in that the difference between using the right words and the wrong words can be the difference between dramatic success and catastrophic failure. We spoke with three communications experts to learn more: Sean Garrett was the first VP of Communications at Twitter. He previously worked for Governor Pete Wilson of California and has also co-founded two separate communications firms, with clients including Slack, Cisco, and Disney. He’s currently the Managing Partner at Pramana Collective. Faryl Ury is a former reporter, with experience at NPR and the Associated Press. Her communications experience also began in government, working for a US Senator, before moving to Square, Uber, and then Dropbox for a marketing role. She’s now the Director of Communications at Aurora, a leading autonomous vehicle company, with investors including Sequoia Capital, Amazon, and Hyundai. Adi Raval served as a journalist at both ABC News and the BBC, covering 9/11, the Iraq War, and the White House before moving into government. He was first a diplomat for the State Department, serving in Afghanistan, and then a spokesperson and Director of Communications at USAID. After leaving government, Adi was the top communications executive for the Bechtel Corporation, and most recently Head of Comms and PR for TaskRabbit. He’s also a term member for the Council on Foreign Relations.
September 26, 2019
S1E6: Mo Money Mo Problems: The Role of Finance in Tech Startups
Hear from two finance experts with experience from Calm, AdRoll, Morgan Stanley,, Zeus Living, and Duda as we unpack how to build a career in finance at a tech startup and how founders should be thinking about hiring and managing this function.  Our guests for this episode are: Stephanie Hsiung is the CFO of Duda, a new and exciting enterprise website builder. Prior to taking the CFO role at Duda, Stephanie served as the VP of Finance at Calm, the leading meditation and mental wellness app and recent unicorn. She was also previously the VP of Finance at, and was at AdRoll before that. Mark Kang is the Head of Finance at Zeus Living, which is one of the fastest-growing providers of furnished housing for business travelers. He brings experience from venture capital, banking at Morgan Stanley, where he managed IPOs, and also spent time at Barclays.
August 20, 2019
S1E5: Be a Chik-Fil-A, not a Comcast: The Keys to Amazing Customer Service
This week’s episode features AirBnB's Global Product Director of Customer and Community Support Platform Products, Andy Yasutake, and Carta's Head of Enterprise Relationship Management, Jared Thomas. AirBnB, one of the most valuable private tech companies in the world, has millions of hosts who trust strangers (guests) to come into their homes and hundreds of millions of guests who trust strangers (hosts) to provide a roof over their head.   Carta, a $1 Billion+ company formerly known as eShares, is the leading provider of cap table management and valuation software, with thousands of customers and almost a million individual shareholders as users. Customers and users entrust Carta to manage their investments, a very serious responsibility requiring trust and security.
August 08, 2019
S1E4: Experts from WeWork and Brex Talk Marketing: Getting the Most Bang for your Buck
This week’s edition features Christiana Rattazzi, Head of Technology Marketing at WeWork, the leading coworking company with a valuation of $47 Billion and a rumored impending IPO after almost $8 billion in financing. Also joining the show is Elenitsa Staykova, VP of Marketing at Brex, another fast growing unicorn that is the leading provider of credit cards to startups and tech companies.  In this episode, Christiana and Elinitsa explain how marketing works, how to get into and succeed in a marketing career, and how founders should think about hiring and managing the marketing function. With their experiences at two of tech’s biggest and most innovative marketers, WeWork and Brex, this episode is packed with broad perspectives and deep insights. 
July 24, 2019
S1E3: Understanding Your User - The Art and Science of the Design and UI/UX Behind Facebook, Google, Mint, and Edmodo
This week’s edition features Gülay Birand, UX Lead and Product Design Manager at Facebook, and Tim Rechin, Head of Design at Edmodo, the leading education technology company. Gülay and Tim share their experiences and explain design, UI/UX, how to build a career in these fields, and how entrepreneurs should think about them. Gülay and Tim bring experience from other great companies beyond just Facebook and Edmodo, including the likes of Google, Amazon, Mint, and SAP. Having seen and grown in their disciplines from across a variety of companies and customer types, they share both broad and deep insights from the tech industry.
July 11, 2019
S1E2: Product Management - What Even Is It? Answers from PMs at Google and Slack
This week’s edition of The Operators features Lorilyn McCue, product manager at the recently publicly listed company Slack, the fastest growing enterprise software company ever, and Jamal Eason, a senior product manager at Google, known as a training ground for great product managers.   Lorilyn and Jamal explain what product management is and isn't, how to get good at it, and how entrepreneurs should think about product management as a discipline.  More at
June 25, 2019
S1E1: Enterprise Sales w/ DocSend CEO Russ Heddleston and Acceleprise General Partner Whitney Sales
This week’s edition of The Operators features Whitney Sales, a general partner at Acceleprise, the leading enterprise SaaS accelerator, and Russ Heddleston, founder and CEO of DocSend, a fast rising document management and sharing product.  Whitney brings sales experience from Loopnet, Meltwater, SpringAhead/Tallie, and People Data Labs, before starting her own sales consultancy aptly named “The Sales Method.” Russ brings experience from founding and selling his first company to Facebook, before becoming the first sales person of the second company he founded, DocSend.  If you’ve ever had to convince anyone of anything, or are interested in a career in sales or starting a company where you will have to hire or manage sales people, you can’t miss this episode. More at
June 17, 2019