Guest: Scott Cutler, CEO of StockX What’s the point of climbing a mountain, or heli-skiing in the Swiss Alps, or biking in the Tour de France? StockX CEO Scott Cutler has done all three, and for him, the answer is momentary perspective. “When you’re descending, you don’t see, but you know what is above,” he says. “You have experienced and have seen what you saw at the peak and you take that with you into the next experience.” He stressed that the pleasure of being at the top is a fleeting incent...
Dec 04, 2023•56 min•Ep. 167
Guest: Brian Long, former CEO of Attentive and author of Problem Hunting: The Tech Startup Textbook Brian Long’s most recent company, Attentive, was originally designed to help clients communicate with their distributed workforce — but about six months in, he and his co-founder realized that that business would not grow as quickly as they had hoped. So, they decided to pivot to SMS marketing, at the cost of a few dubious employees and a well-known Fortune 500 client. The successful pivot confirm...
Nov 27, 2023•1 hr 5 min•Ep. 166
Guest: Spencer Rascoff, co-founder and former CEO of Zillow + co-founder and general partner at 75 & Sunny When terrorists attacked the US on 9/11, Hotwire co-founder Spencer Rascoff and his colleagues had to put their own trauma aside and “spring into action” — the travel site had sold tens of millions of dollars’ worth of non-refundable flights and hotel rooms and customers who wouldn’t be traveling wanted their money back. Now a visiting professor at Harvard Business School, Spencer teach...
Nov 20, 2023•1 hr 11 min•Ep. 165
Guest: Luis von Ahn, CEO and co-founder of Duolingo When Luis von Ahn wanted to go to college in the United States, he had to take a standardized test called the TOEFL, or Test of English as a Foreign Language. But there was nowhere in his home country of Guatemala that could accommodate another test-taker, so he flew to war-torn El Salvador, just to take the TOEFL. Many years later, as the co-founder and CEO of Duolingo, Luis and his team “decided this type of thing, we could do a lot better.” ...
Nov 13, 2023•1 hr 4 min•Ep. 164
Guest: René Lacerte, CEO of Bill René Lacerte co-founded the online payroll firm PayCycle in 1999, and led it for six years until he was asked by the board to step down. Today, with 17 years as the CEO of Bill under his belt, he’s able to look back on that time with clearer eyes. “The title on my card is ‘CEO and Founder,’” he says. “At Paycycle, it was ‘Co-Founder and CEO.’” The order matters, because once you’ve become a founder or co-founder, you are one no matter what — and in hindsight, Ren...
Nov 06, 2023•1 hr 3 min•Ep. 163
Guests: Parker Conrad, CEO of Rippling, and Mamoon Hamid, partner at Kleiner Perkins How long did it take for Parker Conrad to stop wanting revenge? “I’ll let you know when it switches over,” the Rippling CEO and co-founder jokes. He resigned from his last company , the buzzy HR unicorn Zenefits, in 2016 and then quickly realized that the company’s new leaders would never return it to its former glory. He still loved the problems he had been trying to solve, and launched Rippling because “there ...
Oct 30, 2023•1 hr 2 min•Ep. 162
Guest: Evan Goldberg, founder and EVP of Oracle Netsuite In the late 1980s and early 1990s, Evan Goldberg working at Oracle, helping to bring its database software to the Mac. He left in 1995 because “I always wanted to do my own thing” and — with Larry Ellison’s support — launched his first startup, Embed. When it failed, he told Larry that he wanted another bite of the apple. “It’s the most exciting, it’s the most satisfying,” Evan said of startups. “It’s the highest risk, but ... even though ...
Oct 23, 2023•1 hr 6 min•Ep. 161
Guest: Rahul Roy-Chowdhury, CEO of Grammarly Driven by generative tools like ChatGPT, artificial intelligence is hot — but Grammarly CEO Rahul Roy-Chowdhury wishes that “AI” stood for something else: “Augmented Intelligence.” A longtime Googler and lifelong believer in using technology to make peoples’ lives better at scale, Roy-Chowdhury now leads a company well-positioned to do exactly that. “In the early days, Grammarly was all about the rules of language,” he says. “Now, with generative AI, ...
Oct 16, 2023•1 hr 3 min•Ep. 160
Guest: Jeff Shiner, CEO of 1Password Far from the Silicon Valley bubble, in Waterloo, Ontario, they try to do things a bit differently, says 1Password CEO Jeff Shiner. “Our mantra has been, build a good product, support the heck out of your customers,” he says. Some businesses and VCs in the Valley, he argues, don’t draw enough of a distinction between customers and users, spending all their time chasing the latter. For many years, the whole team at 1Password — including the co-founders — would ...
Oct 09, 2023•1 hr 4 min•Ep. 159
Guest: Matt Steckman, CRO of Anduril Industries Walk into one of Anduril Industries’ offices and it might take a minute for you to realize: This is a defense contractor. “It feels like a tech company, stylistically,” says CRO Matt Steckman, “because we know we have to recruit the best software talent in the world.” Matt says the executive team spends a “comical” amount of time on recruiting, one of his personal passions, and especially works to minimize the number of people who turn down offers....
Oct 02, 2023•1 hr•Ep. 158
Guest: Greg Brown, CEO of Udemy Every night before he goes to bed, Greg Brown makes a to-do list. He has to because, as the CEO of the online learning platform Udemy, setting his priorities helps ensure that he makes the most of the scarce time on his calendar. “If I’m meeting with employees, what’s the message I want them to walk away with?” he asks. He also wants to make sure his team isn’t getting distracted by Udemy’s stock price. “Where it be sports, or life, or in business, you’ve got to b...
Sep 25, 2023•1 hr 1 min•Ep. 157
Guest: Chris Degnan, CRO of Snowflake Chris Degnan was a teenager when his world got turned upside-down: His stockbroker father was revealed to be a serial liar & fraudster and was sent to prison; the wealth he thought his family had evaporated; and their house was foreclosed on by the IRS. The traumatic experience gave him both an “insane drive” and a slew of anxieties, which shaped the person he became as an adult ... and led him, eventually, to the C-Suite of Snowflake. “Those things have...
Sep 18, 2023•54 min•Ep. 156
Guest: Jim Lanzone, CEO of Yahoo Jim Lanzone doesn’t waste time thinking about what other people think of him ... or the companies he has run. After helping to rejuvenate Ask.com in the early 2000s, he has more recently served as CEO of Tinder, and now Yahoo. As an expert in brand turnarounds, he says, “don’t worry about what the world thinks ... worry about your growth versus yourself.” With a focus on people and product, Jim believes, “not only can you accomplish a lot, you’re going to make a ...
Sep 11, 2023•1 hr 7 min•Ep. 155
In this special episode of Grit, Joubin looks back at what five past guests had to say about building a sales operation inside rapidly-growing companies: Intro (00:30) Stripe’s Mike Clayville on first principles & “tornado companies” (01:02) Former Paypal VP Marcy Campbell on establishing a successful sales motion (11:37) LinkedIn COO Dan Shapero on effective sales leadership during hypergrowth (20:16) Herbold Consulting CEO Jim Herbold on “unicorn meat” (32:32) CRO Chris Degnan on the pivot...
Sep 04, 2023•1 hr 8 min•Ep. 154
Guest: Yan-David Erlich, COO and CRO of Weights & Biases After starting four companies, Yan-David Erlich had found happiness and success as a GP in Coatue’s venture fund — but then, after investing in the AI developer platform Weights & Biases, he realized the time was right to get back into operating. That was not a decision he made lightly, consulting with his wife before he became the startup’s COO. The challenges of entrepreneurship get easier, he explains, when you have a supportive...
Aug 28, 2023•1 hr 12 min•Ep. 153
Guest: Nick Mehta, CEO of Gainsight Gainsight CEO Nick Mehta describes himself as “the person who goes all in, on whatever.” So when he had a personally difficult year, he didn’t just go to therapy — he also talked to a professional coach, and read about religion, and experimented with (legal) ketamine therapy. All of that led to him “better understanding the inner self ... [and] helping to find ways to suppress the exterior.” In other words, even though Gainsight’s culture is suffused with Nick...
Aug 21, 2023•1 hr 12 min•Ep. 152
Guest: Manny Medina, CEO of Outreach In its Seattle headquarters, the sales execution platform Outreach has at least one wall covered in AI diagrams and architectural flows. CEO Manny Medina says that’s because he believes “there’s no world in which reps don’t have an assistant the way that coders do.” The AI revolution has also given Manny — who got his M.A. in computer science at Penn — a chance to be more hands-on than your average CEO of a $4 billion company. “I try not to think myself as a ...
Aug 14, 2023•1 hr 7 min•Ep. 151
Guest: Aaron Levie, CEO of Box, and Mamoon Hamid, partner at Kleiner Perkins When he was a newly minted venture capitalist at USVP, Mamoon Hamid got a tip that he should meet a young entrepreneur named Aaron Levie, and fought for the right to invest in his cloud storage startup, Box. For years after that initial investment, the two men say, Box’s fate was precarious: “We could have died any day,” Mamoon says, and Aaron recalled several times he had to be talked “down from a ledge.” Today, they t...
Aug 07, 2023•1 hr 3 min•Ep. 150
Guest: Carl Eschenbach, co-CEO of Workday When Carl Eschenbach decided to leave VMWare after more than 14 years as COO, no one believed it: Not chairman Joe Tucci, not CEO Pat Gelsinger, and maybe not Carl himself. But he needed a more predictable work-life balance to help raise his teenage children. For the next seven years, he served as a partner at Sequoia Capital. And every day, he thought — and to his wife’s chagrin, talked — about going back: “It was always on the back of my mind,” he says...
Jul 31, 2023•1 hr 22 min•Ep. 149
Guest: Bob Muglia, “The Datapreneurs” Co-Author and Former Snowflake CEO Longtime Microsoft executive and former Snowflake CEO Bob Muglia was done with his book about using data to drive the digital economy — and then ChatGPT came out. “The timeline for artificial intelligence moved in by 50 years in my head,” he recalls. Bob then told his co-author Steve Hamm that they needed to update “The Datapreneurs” to focus more on AI. “For the first time, we have intelligence in a computer,” he says. “En...
Jul 24, 2023•1 hr 21 min•Ep. 148
Guest: Noam Bardin, founder of Post News One of the “aha” moments that could sway a dubious Waze user, recalls former CEO Noam Bardin, was navigating around “all those idiots sitting in traffic... and you’re like, ‘I’m a genius.’” Now, at the social news app Post, Noam says the “aha” is avoiding partisan gridlock and paywalls. Social incumbents boost engagement by making users angry, while Post just wants you to read. “If we can remove friction and give you the right articles at the right time, ...
Jul 17, 2023•1 hr 30 min•Ep. 147
Guest: Bipul Sinha, co-founder and CEO of Rubrik When Bipul Sinha graduated from the Indian Insitute of Technology and came to America to work in tech, his mother told him: Don’t start a company. His ambitious father was a failed pharma entrepreneur, and Bipul was content for most of a decade to hold a steady job at Oracle. But in his early 30s, he began to shed his risk aversion, pursuing a part-time MBA and more difficult jobs, and by the time he co-founded the data security firm Rubrik in 201...
Jul 10, 2023•1 hr 10 min•Ep. 146
Guest: Ted Purcell, CRO of Tealium The biggest difference between small companies and big companies, says Tealium CRO Ted Purcell, is that at untested early-stage firms, you have to convince workers “to truly believe in what they believe... It’s not just ‘do this’ or ‘do that.’” To unlock high performers, Ted explains, you need to give them a “religious level” of belief in the company and the value it delivers to customers, which will carry over into every aspect of their jobs. And this is even ...
Jul 03, 2023•1 hr 8 min•Ep. 145
Guest: Jay Parikh, CEO of Lacework Jay Parikh describes himself as a “stickler” for meetings that start and end on time, and holds himself to the same expectations as his workers. “It’s just really important as a leader to set the standard for how everybody else should be respected,” the Lacework CEO says. “Too often in our industry, executives think that they can show up late, hold a meeting late, and everybody will adjust.” No one will complain, he says, to the person on top of the org chart w...
Jun 26, 2023•1 hr 11 min•Ep. 144
Guest: Dave McJannet, CEO of HashiCorp To scale a company effectively, says HashiCorp CEO Dave McJannet, you will have to make something like 10 decisions every single day. “There’s generally one that really needs to be right, but there are eight that if you get them wrong, you will cause real damage to yourself,” he says. “It won’t be fatal, and a lot of times, it’s cultural damage.” Sometimes, he adds, these decisions can seem innocuous, like deciding how to run internal town halls with worker...
Jun 19, 2023•1 hr 15 min•Ep. 143
Guest: Robert Chatwani, President and General Manager of Growth at DocuSign Robert Chatwani’s first reinvention was in his early 20s, when he left McKinsey & Company to start a people-powered commerce startup called MonkeyBin. And in the ensuing decades, his entrepreneurial energy hasn’t slowed down, with hops to eBay, Spring, Atlassian, and now DocuSign, where he is the President and General Manager of Growth. He cites a “healthy anxiety” that comes from getting too comfortable in any role,...
Jun 12, 2023•1 hr 17 min•Ep. 142
Guest: Ariel Cohen, CEO and co-founder of Navan As a business travel-focused startup, Navan (previously known as TripActions) was heavily impacted by the coronavirus pandemic in 2020; after laying off 24% of the staff, CEO Ariel Cohen says he became a “wartime CEO,” spending three months in “complete denial and just executing.” By June, employees were leaving and he was depressed — but he still believed that business travel would come back. “You cannot just look at a moment and say that it will ...
Jun 05, 2023•1 hr 17 min•Ep. 141
Guest: Seth Dallaire, CRO at Walmart When Seth Dallaire was approached by Walmart about joining their team as CRO, he had one question: Are they serious? Seth knew that Walmart wanted him for his digital experience, having worked at Instacart and Amazon, but he also knew that building alternative revenue streams at a traditional retailer could be an uphill battle. “I knew I was gonna have to [fight the fight], it was just whether I’d have the air cover from up top to say, ‘This is strategic,’” S...
May 29, 2023•1 hr 6 min•Ep. 140
Guest: Matt Mochary, CEO of Mochary Method Matt Mochary was only 31 when he sold the company he co-founded, Totality, to Verizon, “and I made enough money that that was it,” he recalls. “I didn’t have to make more money anymore.” Instead, he decided to pursue projects that in one way or another would help other people, including a documentary about the slums of Rio de Janeiro and a program to train ex-convicts in the skills of legitimate work. Today, he coaches tech and finance leaders such as B...
May 22, 2023•1 hr 17 min•Ep. 139
Guest: Shoaib Makani, CEO of Motive “When we fail,” says Shoaib Makani, “it is because we have not understood the customer problem deeply and allowed them to guide us.” This wisdom is hard-won: Motive’s first product, an app for fleet management of trucks, idled for four years before becoming a runaway success story. Emboldened by this, the CEO tried to make an orthogonal push into all kinds of freight, “guns blazing,” only to realize six months in that he had way overestimated Motive’s competit...
May 15, 2023•1 hr 10 min•Ep. 138
