Grit

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 confirmed Brian’s belief that it’s possible to over-commit to one solution, when in fact there may be bigger and better problems to solve. “I’ve just seen so many entrepreneurs spend years of their life building something being stuck with it,” he says, “and then trying to figure out how to fit it into something that doesn’t work.” 

In this episode, Brian and Joubin discuss zero to one building, the problem with how entrepreneurs solve problems, How to Win Friends and Influence People, Matt Mochary, Tom Mendoza, transactional relationships, the dangers of ego, optimists and realists, best man speeches, defining a unique culture, reverse selling, Lunar Holdings, Peter Reinhardt, marketing conservatively, and business book sales.

In this episode, we cover:

• New York vs LA (00:54)
• How Brian feels, six months after stepping away from the CEO role (02:37)
• Product-market fit and TAM modeling (06:07)
  Build last (09:05)
• The qualities of great entrepreneurs (13:24)
• Tap Commerce and starting in sales (15:49)
• Listening and remembering names (20:40)
• The day after selling Tap Commerce (23:32)
• Starting another company, Attentive (25:07)
• Resilience and optimism (29:21)
• Fear, doubt, and the worst-case outcome (32:50)
• What Brian would tell his 29 year old self (37:13)
• Hiring and pivoting at Attentive (41:17)
• Text message marketing (45:49)
• How Brian interviews people (50:12)
• His new holding company, Lunar and its first startup (51:52)
• Don’t go social (55:21)
• What Brian is personally excited about and what “grit” means to him (01:01:57)

Links:

• Connect with Brian
  • LinkedIn
  • Buy Brian’s book, Problem Hunting: The Tech Startup Textbook
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

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 teaches this case to his students because this dilemma was not unique to 2001: “What the hell do you do when you’re running a company ... and all of a sudden, a pandemic happens? Or SVB shuts down?”

In this episode, Spencer and Joubin discuss Zestimates, context switching, Tom Brady, reinvention, Shaq, the live music business, beating pain, personal connection to tragedies, the structure of rounds, Juul, the qualities of success, Stewart Butterfield, Travis Kalanick, second homes, two-way doors, overstating risk, “Dad, I Have a Question,” management by walking around, and Carl Eschenbach.

In this episode, we cover:

• Spencer’s post-Zillow life (00:57)
• From player to coach (03:47)
• “The Forrest Gump of technology” (08:21)
• Joseph Rascoff and the Rolling Stones (10:56)
• Teaching grit to kids (14:43)
• Spencer’s brother (18:55)
• Channeling pain into achievement (21:35)
• Co-founding Hotwire (24:37)
• The impact of 9/11 (27:51)
• Re-capitalization and selling to Expedia (35:17)
• “Let’s build a real estate website” (38:05)
• Office Hours and founder-product fit (45:12)
• How Pacaso works (53:22)
• Career mirrors and leaving big companies (57:01)
• Staying organized (01:04:20)
• Dinner with the family (01:07:43)
• What “grit” means to him (01:09:14)

Links:

• Connect with Spencer
  • Twitter
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

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.” Today, more than 4,500 universities accept the results of the online Duolingo English Test — a boon for the estimated 2 billion people currently learning English around the world.

In this episode, Luis and Joubin discuss returning to the office, Carnegie Mellon, identifying strivers, the “Luis dashboard,” ignoring Reddit, pre-meetings, the hardest part of learning, sounding dumb, private security, the job of a professor, digitizing books, 
working out every day, April Fools’ campaigns, Duo the owl, and hiring nice people.

In this episode, we cover:

• Working in Pittsburgh, in-person (00:57)
• How Duolingo hires (06:48)
• Growing up in Guatemala (10:29)
• Luis’ parents, intelligence, and drive (12:09)
• His morning routine (16:56)
• Ground truth (19:39)
• “The smaller the team, the better” (22:29)
• Language education and human behavior (24:32)
• Learning English (28:53)
• Back to Guatemala (32:03)
• CAPTCHA and reCAPTCHA (36:10)
• Money vs. impact (41:26)
• Luis’ TEDx Talk and public speaking tips (44:46)
• Love Language and nontraditional marketing (48:46)
• Doubling down on what works (53:27)
• Slow hiring (56:44)
• Would Luis ever start something new? (59:28)
• Who Duolingo is hiring and what “grit” means to Luis (01:01:46)

Links:

• Connect with Luis
  • Twitter
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

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, René believes he failed to keep up with how PayCycle was changing. “My job as a CEO, it changes every freaking day,” he says of Bill. “We’ve 10x’d in four years. My job today has far more responsibilities and requirements than it had four years ago. So how do you get ready for that?”

In this episode, René and Joubin discuss Silicon Valley OGs, the office environment, taking care of yourself, memorizing acronyms, Christmas presents, 11-finger jazz, intentionality and spontaneity, ordering your job titles, problem-solving at night, understanding insecurities, and measuring success.

In this episode, we cover:

• Why René did not want a corner office (02:22)
• The weight of being CEO (04:40)
• Dinner with the kids (08:50)
• Prioritizing, energy, and fitness (11:05)
• Music and René’s parents (17:31)
• His father and pride (23:13)
• Empathy for small businesses (28:00)
• Family values (32:46)
• “Legacy, I don’t care about that” (36:15)
• Stepping down from PayCycle (41:16) 
• Starting Bill (46:58)
• Leading in hyper-growth (50:10)
• The early years (53:07)
• Conventional wisdom (56:08)
• Who Bill is hiring and what “grit” means to René (01:01:02)

Links:

• Connect with René
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

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 was an opportunity there, [and] if it works ... it’s going to be fundamentally and foundationally better as a product.” It worked. As of March, Rippling has been valued at more than $11 billion, more than double Zenefits’ peak.

In this episode, Parker, Mamoon, and Joubin discuss what happened at Zenefits, avoiding press coverage, FOMO and expectations, Paul Graham, fixing corporate insurance, Ryan Peterson’s “revenge portfolio,” CEO coaches, Mike Vernal, approving expenses, anecdata, and the Costco of SaaS. 

In this episode, we cover:

• How Parker and Mamoon met (00:56)
• The Zenefits Series B (06:29) 
• “Stuck in a nightmare” (09:20) 
• Entrepreneurship is “soul-destroying” (12:46) 
• Parker’s first company, SigFig (17:17) 
• Starting a company for the right reasons (21:02) 
• Starting over after Zenefits (27:06) 
• Avenging Zenefits (31:57) 
• Rippling’s unusual Series A (38:40) 
• What it does well (43:13) 
• “Go and see” (46:35) 
• The compound startup (51:44)
• Who Rippling is hiring and what “grit” means to Parker (01:00:39) 

Links:

• Connect with Parker
  • Twitter
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

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 I did just get married and we were going to have a kid, I still had this real appetite for risk.” The gamble paid off: In 2016, Oracle bought Netsuite for $9.3 billion, and he’s been back “home” ever since.

In this episode, Evan and Joubin discuss overestimating and underestimating, rose-colored glasses, collaborative partnerships, Marc Benioff, Larry Ellison’s superpowers, AI skepticism, Rise of the Resistance, energy vs. focus, supportive partners, Zach Nelson and Jim McGeever, and building the cloud.

In this episode, we cover:

• Eighteen years to $9.3 billion (00:47)
• Startups and failure (03:36)
• CEO vs. CTO vs. technical founder (06:38)
• Growing up and moving to California (10:08)
• Eight years at Oracle (12:30)
• Introversion (16:12)
• AI is the new internet (17:38)
• The incumbents’ advantage in AI (23:30)
• Inspiration to start something new (25:30)
• Leaving Oracle in 1995 & starting Embed (28:17)
• When to cut and run (32:16)
• Evan’s wife, Cindy (36:05)
• Starting NetSuite (40:18)
• Going public and the stock rollercoaster (43:46)
• OneWorld and fighter jets (47:17)
• Oracle’s acquisition of NetSuite (50:48)
• Co-founder and family cohesion (56:58)
• Do-overs (59:25)
• What would Evan do if not Netsuite? (01:02:29)
• Who Netsuite is hiring and what “grit” means to him (01:03:41)

Links:

• Connect with Evan
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

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, we can actually help people across a much broader swath of communication tasks.”

In this episode, Rahul and Joubin discuss digital distraction, responsible AI, John Oliver, Ali Ghodsi, the hype cycle, fragmentation, being kind to yourself, Amp It Up, intentional strategy, candid dialogue, Google Chrome, and Dancing with the Butterfly.

In this episode, we cover:

• Growing up in India (01:05)
• Meaningful, impactful work (07:12)
• The potential of AI (13:09)
• Invisible AI (19:53)
• Would Grammarly go public? (23:51)
• What drives the business (28:19)
• Too many emails (31:05)
• Being an introvert CEO (35:11)
• How Rahul got the top job (37:36)
• Insecurity (39:48)
• Snowflake CEO Frank Slootman (41:57)
• Rahul’s decision-making framework (45:40)
• “I deprecated the thing I built” (54:12)
• The dino game (56:28)
• The book on Rahul’s desk (59:49)
• Who Grammarly is hiring and what “grit” means to Rahul (01:01:06)

Links:

• Connect with Rahul
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

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 try to empty out the customer support queue every day. If the company hadn’t waited 14 years to raise outside funding, Jeff says, it would have been a lot harder to listen to them and build the best product.

In this episode, Jeff and Joubin discuss PowerPoint slides, LEGO sorting, early computers, artificial general intelligence, e-commerce, users vs. customers, loss of control, outsourcing, managers and team leads, OKRs, password schemes, Polish food, Ryan Reynolds, and live TV hits.

In this episode, we cover:

• Abnormal sleeping patterns (02:39) 
• “Playing farmer” (05:00)
• Running and competition (07:05)
• Fear of failure & the speed of technology (10:14)
• Jeff’s pre-1Password jobs (14:46)
• The Silicon Valley bubble (17:05)
• Raising $920 million (19:47)
• Hiring after the signals (23:44)
• Chief Eliminator of Obstacles (30:52)
• “We need to do less” (33:32)
• Could 1Password have grown differently? (38:22)
• 1Password vs. the competition (41:43)
• Customer Support Monday (43:57)
• Hiring by doubling (46:23)
• Thinking about exits (49:16)
• Imposter syndrome (54:29)
• “Do I have any real skills left?” (57:04)
• Speed and confidence (59:26)
• Who 1Password is hiring and what “grit” means to Jeff (01:03:02)

Links:

• Connect with Jeff
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

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. “That’s something that a lot of companies, both tech and non-tech, miss ... Are you losing candidates at the very end, where you spent a tremendous amount of time and resources getting to that decision?”

In this episode, Matt and Joubin discuss security clearance, Lockheed Martin and Boeing, politics vs. technology, Palantir, consensus building, border security, command and control technology, the qualities of great defense tech workers, and long-term thinking. 

In this episode, we cover:

• The importance of defense tech (02:37)
• What Anduril does (04:33)
• Barriers to entry (07:58)
• How the government picks winners (11:56)
• Matt’s path to the defense industry (17:04)
• Why he left Palantir (19:57)
• Low moments and self-awareness (22:17)
• What you can control (27:36)
• Joining Anduril (30:14)
• Surveillance towers (33:26)
• Dive Technologies (37:30)
• Risk mitigation (39:24)
• Kinetic warfare (42:43)
• Recruiting top talent (45:26)
• Performance against expectations (48:34)
• Caring and empathy (51:25)
• Hitting revenue goals (52:31)
• How Matt manages his calendar (54:38)
• The economics of defense (56:26)
• Who Anduril is hiring and what “grit” means to Matt (58:11)

Links:

• Connect with Matt
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

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 be able to block out the noise,” Greg says. “Focus on what you can control and maniacally execute against those objectives.”

In this episode, Greg and Joubin discuss fitness routines, VO₂ max, multi-athletes, Webex, the dotcom bust, Gregg Coccari, streamlining, setting priorities, listening to analysts, and being intentional with family.

In this episode, we cover:

• Cold plunges and healthspan (00:42)
• Finding time for fitness (07:48)
• Greg’s father (10:04)
• From sports to business (15:55)
• Two-year investments in companies (18:15)
• Achievers and motivation data (22:57)
• Becoming CEO of Reflektive (26:07)
• Why Greg joined Udemy and what it does (28:40)
• The distraction of a stock price (34:54)
• Daily to-do lists (39:20)
• Back to growth (41:45)
• Go to market CEOs (48:25)
• Coachability (50:49)
• Applying AI to customer solutions (52:16)
• At-home office hours (56:09)
• Who Udemy is hiring and what “grit” means to Greg (58:12)

Links:

• Connect with Greg
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm