Grit

Guest: Dev Ittycheria, CEO and President of MongoDB

When you think about who you were and the decisions you made two, or four, or eight years ago ... how do you feel? Dev Ittycheria, the President and CEO of MongoDB, says he’s embarrassed about certain things he did — and that’s a good thing. “If you’re not [embarrassed], that means you’re not really growing that fast,” he says. He recalled one of his mentors, former BladeLogic chairman Steve Walske, explaining that everyone has an overinflated opinion of themselves, and the great leaders keep the gap between that opinion and reality narrow. One of the hallmarks of such a leader, Dev says, is that they have the intellectually honesty to recognize their own strengths and weaknesses, which others perceive.

In this episode, Dev and Joubin discuss looking for bad news, chips on your shoulder, Ivy League schools, being an outsider, highly educated parents, “aging out,” Bruce Springsteen, Chief People Officers, Frank Slootman and John McMahon, passive aggression, vulnerability as strength, imposter syndrome, open-source licenses, introverts, and time management.

In this episode, we cover:

• Shlomo Kramer and the “burden of persona” (00:59)
• Why BladeLogic started in Boston (04:30)
• The psychological edge (07:08)
• Dev’s family and education (08:56)
• “Am I good enough?” (13:11)
• “Do not squander this opportunity” (16:22)
• Dev’s wife (19:32)
• Fear of irrelevance (21:23)
• Relevance after retirement (26:06)
• Why CEO is a lonely job (28:14)
• Trusting your team (31:43)
• The meaning of life (35:16)
• Judgment and introspection (38:16)
• Taking people to the woodshed (40:54)
• What matters to other people (44:39)
• Taking risks at MongoDB (51:08)
• Founder-led businesses (53:26)
• What type of company is MongoDB? (57:39)
• Work-life harmony (01:00:20)
• Who MongoDB is hiring (01:03:17)

Links:

• Connect with Dev
  • 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: Frank Slootman, CEO and Chairman of Snowflake and author of Amp It Up

Snowflake CEO Frank Slootman doesn’t recall a time in his childhood where new achievements were celebrated — because, according to his father, putting everything into your work and “leaving it all on the field” was the only choice. “The problem with it,” Frank says, is that “it becomes a ‘never enough’ dynamic, because when is it enough?” To this day, he comes home on Friday night and asks himself, “Did it mater that I was there? ... If I’m just a passenger on the ship, that’s my nightmare.”

In this episode, Frank and Joubin discuss acting with urgency, Shlomo Kramer, negative role models, Elon Musk, Teddy Roosevelt’s “Man in the Arena” speech, aptitudes and weaknesses, ServiceNow, and the life spark of business.

In this episode, we cover:

• Being tough on yourself (00:59)
• Sailing and inner peace (03:00)
• Confronting your demons (09:07)
• Scaling Data Domain (11:15)
• Judging talent (15:20)
• That gnawing feeling (18:16)
• Daring greatly and rejecting pride (21:04)
• “Did it matter that I was there?” (25:02)
• How you play the game (27:59)
• The best version of yourself (29:59)
• Learning from the best (34:06)
• Sales as inspiration (37:52)
• Retirement and Tom Brady (39:09)
• The fog of war (41:16)
• Snowflake vs. Data Domain (44:31)
• Respect for luck (48:48)
• Who Snowflake is hiring (50:42)

Links:

• Connect with Frank
  • LinkedIn
  • Buy Frank’s book, Amp It Up: Leading for Hypergrowth by Raising Expectations, Increasing Urgency, and Elevating Intensity
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Jason Kelly, CEO and co-founder of Ginkgo Bioworks

Almost everyone in the second generation of biotechnology entrepreneurs, says Ginkgo Bioworks CEO Jason Kelly, works in that field because of one thing: Jurassic Park. The Michael Crichton novel-turned-Steven Spielberg movie captured both the wonder and beauty of bioengineering, and the challenges of bending DNA to your own ends. “You didn’t invent biology,” Jason says. “You need to have humility in the face of it ... because life will find a way. It will do things you don’t expect. It’s not a computer.” 

In this episode, Jason and Joubin discuss the Wall Street rollercoaster, designer cells, the history of biotech, Herbert Boyer and Genentech, ChatGPT, extinct flowers, Sam Altman and YCombinator, first principles thinking, compounding risk, Patrick Collison, super-voting shares, capital intensive businesses, Pets.com, and why biology is like “freakishly powerful alien technology.”

In this episode, we cover:

• Being private vs. being public (00:58)
• How bioengineering works (04:27)
• Jurassic Park (08:51)
• Biotech breakthroughs (12:15)
• Why this field is not well-known yet (16:57)
• “The ChatGPT moment for biotech” (22:05)
• Meaningful stuff takes forever (26:23)
• Ginkgo’s first five years (29:02)
• Why the company went public (36:20)
• Short sellers, Warren Buffett, and Elon Musk (42:08)
• Applying AI to DNA engineering (47:57)
• The long-term future (55:57)
• Who Ginkgo is hiring (58:39)

Links:

• Connect with Jason
  • 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: John McMahon, author of The Qualified Sales Leader: Proven Lessons from a Five Time CRO

A hell of a lot of people work in sales. But until recently, says five-time CRO and The Qualified Sales Leader author John McMahon, it was rare for colleges and universities to offer a sales degree. Salespeople had to learn on the job from experienced coaches, and adapt. And their bosses, John explains, had to themselves as agents of transformation. “If somebody’s really smart, they’re going to pick up the knowledge,” he says. “If they have what I call a PHD — persistence, heart, and desire — they’re going to learn the skills ... You’re going to have to do thousands and thousands of repetitions before you’re going to get good.”

In this episode, John and Joubin discuss lazy LinkedIn cold calls, Tom Brady’s retirement, being “married to your job,” Carl Eschenbach, crying, sales as a calling, corporate culture vs. coaching culture, adaptable workers, opportunity vs. title, Bob Muglia, transactional leaders, sad rich people, cookie-cutter advice, handshake evaluations, and David Cancel.

In this episode, we cover:

• CRO to CEO? (02:21)
• Ego and relevance (04:25)
• Escaping the 90-day grind (06:25)
• Persistence and physical discipline (09:05)
• Daily habits and positive energy (14:12)
• Why John quit BMC (17:09)
• Poor communication (21:17)
• Was there another way? (24:37)
• Identifying sales talent (28:36)
• Showing that you care (32:58)
• Sales leaders as hockey coaches (39:46)
• Firing people (44:25)
• Interviewing the right type of salesperson (49:14)
• Snowflake and Chris Degnan (51:22)
• “What’s the book on you?” (56:03)
• Managing from a position of power (58:01)
• The three “whys” (01:00:31)
• Why John never went VC (01:04:33)
• Is he really done? (01:07:17)
• Shlomo Kramer (01:10:20)
• Having impact (01:13:11)
• Bad advice (01:16:19)
• Working with marketing (01:19:32)
• Sizing people up (01:21:26)
• Can CEOs give up? (01:26:51)
• Coaching sales “artists” (01:28:29)
• What “grit” means to John (01:30:48)

Links:

• Connect with John
  • LinkedIn
  • Buy The Qualified Sales Leader: Proven Lessons from a Five Time CRO
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Angela Duckworth, professor at the University of Pennsylvania and author of Grit: The Power of Passion and Perseverance

“There’s got to be a cost” when you pursue your passions, says University of Pennsylvania professor Angela Duckworth; in fact, the word “passion” comes from the Latin word for “suffering.” But that doesn’t mean that gritty people are unhappy. After the time needed for sleep, daily exercise, friends, and family, Dr. Duckworth explains, “what’s left is more than 40 hours.” Informed by her research and her own happiness, she tries to discourage her students from settling for a 9 to 5 life: “There’s so many people that exemplify a life of dedication, and hard work, and of happiness, and humor, and friends, and family, that I think we should tell young people, ‘Look, don't assume that's not possible.’”

In this episode, Angela and Joubin discuss being punctual, Danny Kahneman, AP Calculus, moving the finish line, teaching grit to children, Arthur Ashe, Diana Nyad, passion and sacrifice, hiring gritty people, “change your situation,” Marc Leder and Rodger Krouse, Invictus, ChatGPT, neural autopilot, and Steve Jobs.

In this episode, we cover:

• “I have a thing with time” (01:36)
• Being the GOAT (06:37)
• Mr. Yom (09:27)
• Chef Marc Vetri (14:15)
• The Devil Wears Prada (16:03)
• Talking about grit (18:12)
• Satisfaction, loneliness, and happiness (20:24)
• Success as a journey (28:23)
• The cost of hard work (32:52)
• Angela’s 70-hour work week (36:31)
• Charisma and loving what you do (40:55)
• Why high achievers have supportive partners (47:07)
• The next book (55:25)
• Pick the right market (57:45)
• Therapy questions (59:53)
• The Incredible Hulk vs. James Bond (01:02:45)
• Automating decisions (01:05:43)
• What “grit” means to Angela (01:09:39)

Links:

• Connect with Angela
  • Twitter
  • LinkedIn
• Additional reading:
  • Redefining Success: Adopt the Journey Mindset to Move Forward
  • Buy Grit: The Power of Passion and Perseverance
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: David Cancel, founder and former CEO of Drift; founder of Rey

After HubSpot acquired his company Performable in 2011, David Cancel became his acquirer’s Chief Product Officer — and didn’t give any thought to how long he’d be in that role. When he started eyeing the exit a few years later, he was told that wasn’t an option: HubSpot had already filed to go public, and an officer of the company leaving in the first 18 months would raise major red flags. “Maybe this is what’s led me to be an entrepreneur,” David recalls. “I can never feel trapped … Someone telling me, ‘you can’t leave,’ I was like, boom. Switch went off in my head … and I was like, ‘I’m out.’” The filing was ultimately delayed and David was able to quit just before the IPO; one day later, he started his next company, Drift.

In this episode, David and Joubin discuss the accountability of doing something, creating constraints, the Whitney Museum, imposter syndrome, Tony Hawk, John Romero, wandering without a map, conservative spending, Brian Halligan and Dharmesh Shah, Phil Jackson, the voices in your head, Shlomo Kramer, righteous independence, cancel culture and diversity, gut vs. data, and killing ideas with discipline.

In this episode, we cover:

• Action and distractions (00:50)
• Observer and outsider (05:36)
• Advising entrepreneurs (11:18)
• “It has to be bigger” (13:23)
• David’s new company, Rey (16:38)
• Remote vs. in-person work (21:24)
• Who David will hire first (25:39)
• Fundraising and bootstrapping (27:39)
• The timeline for Rey (31:48)
• Rebuilding Hubspot’s code base (33:36)
• Leaving HubSpot at the IPO (42:54)
• “You’re not done” (48:19)
• HubSpot’s infamous exec meetings (54:44)
• David’s hardest year and selling Drift (59:26)
• The upmarket mistake (01:03:13)
• Saying no to good ideas (01:08:12)
• What “grit” means to David (01:11:52)

Links:

• Connect with David
  • 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: John Doerr, chairman of Kleiner Perkins

After Kleiner Perkins chairman John Doerr first invested in Google — $12.8 million for 13 percent of the company — he told co-founders Larry Page and Sergey Brin that they needed to hire a CEO to help them build the business. After they took meetings with a variety of successful tech execs, they came back to Doerr and told him “We’ve got some good news and some bad news.” The good news was that they agreed on the need for a CEO; the bad news, Doerr recalls, is that they believed there was only one person qualified for the role: The then-CEO of Pixar and interim CEO of Apple, Steve Jobs. 

In this encore presentation of the 100th episode of Grit, John and Joubin discuss the urgent need to act on the climate crisis, getting turned down by Kleiner Perkins, CEOs as sales leaders, the microprocessor revolution, balancing between work and family, the opportunity of AI and sustainability, what makes Jeff Bezos special, Bing Gordon and the invention of Amazon Prime, the Google CEO search, how the iPhone nearly killed Apple, Steve Jobs’ greatest gift, Bill Gates’ philanthropy, and how Doerr divides his time.

In this episode, we cover:

• John’s two books — Measure What Matters and Speed & Scale — and applying OKRs to the climate crisis (02:39)
• How John got to Silicon Valley and what he learned from his entrepreneurial father, Lou (08:55)
• “I didn’t want to be in venture capital” (16:27)
• Joining Kleiner Perkins at the dawn of personal computing (20:03)
• The internet, cloud computing, smartphones, and the next big tech wave: AI (24:41)
• How John met Amazon founder Jeff Bezos (29:46)
• Google co-founders Larry Page and Sergey Brin, and teaming up with Mike Moritz from Sequoia (38:26)
• John’s friendship with Steve Jobs and the creation of the $100 million iFund for iPhone apps (45:12)
• “Family first” and setting personal OKRs (50:10)
• Working with Bill Gates outside of Kleiner Perkins (52:51)
• Brian Roberts, Comcast, and hustling to make at-home broadband nationwide (59:28)

Links:

• Connect with John
  • 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: Shlomo Kramer, founder and CEO of Cato Networks

Shlomo Kramer has founded three companies to date — Check Point, Imperva, and most recently Cato Networks — and taken the first two public, with plans to do the same with Cato. By any measure, he is a successful entrepreneur, but he defines “success” as “a burden you need to shake off every day.” And the easiest way to do that he’s found is to keep moving, keep failing, and keep creating. The material wealth he’s created, he explains, was never the goal: “It was never about things. It was about ideas and making them real.”

In this episode, Shlomo and Joubin discuss the contexts of our actions, the IDF, taking three companies public, ideas vs. things, kibbutzes, Gong, Sumo Logic, serial entrepreneurs, leading by example, consumer cybersecurity, trusting others, Albert Einstein, “making it to the pass before winter,” and Israeli directness.

In this episode, we cover:

• The delta between micro and macro (00:54)
• Working in wartime Israel (03:18)
• The burden of persona (06:37)
• Shlomo’s family (13:19)
• The time between startups (16:30)
• Self-fulfillment (18:31)
• “What am I going to do next?” (21:14)
• Rebelliousness (24:58)
• Palo Alto Networks (29:42)
• Loyalty and competition (31:32)
• Building trust relationships (35:02)
• “The last one” (37:41)
• Shaq, Tom Brady, and Carl Eschenbach (42:15)
• Tough feedback (46:50)
• Shlomo’s friends (48:18)
• Intellectual honesty (50:14)
• What Cato does (52:37)
• Hiring and work culture (55:23)
• Ignoring startup advice (58:15)
• Ideation and being present (59:22)

Links:

• Connect with Shlomo
  • 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: Arvind Jain, Founder and CEO of Glean, and Mamoon Hamid, partner at Kleiner Perkins

“I’m an engineer, so I have doubts about everything,” says Glean founder and CEO Arvind Jain. Well ... almost everything. Since launching Glean in 2019, he has held to the belief that “all of us are going to have really powerful AI assistants” in the future. With a several-year lead on generative AI tools like ChatGPT, Glean has built a growing club of CIO fans. With the broad acceptance of AI over the past year, Arvind says, “the level of confidence is higher than ever before.”

In this episode, Arvind, Mamoon, and Joubin discuss golfer hats, ideas vs. execution, X1, energy audits, small towns in India, IIT, proving yourself, Rubrik, rejecting product-led growth, “workplace assistants,” CIO fans, internet ’94, Parker Conrad, and work as a hobby.

In this episode, we cover:

• Arvind’s newfound fame (01:08)
• The state of the AI business (03:42)
• “Why now?” (06:05)
• Building great products (09:16)
• Company-building (11:27)
• Arvind’s childhood (14:37)
• Competition and hard work (16:44)
• Leaving Google (18:46)
• Glean vs. Rubrik (20:53)
• The future of work (27:22)
• “Holy shit” moments (29:25)
• Finding positivity (32:51)
• AI hype (34:31)
• How to pick a venture capitalist (38:55)
• Turning off (42:24)
• Hiring and the meaning of “grit” (44:41)

Links:

• Connect with Arvind
  • LinkedIn
• Connect with Mamoon
  • 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: 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 incentive to do it again, not the destination; in life, and in our careers, he argues, the journey is about continually facing new challenges and getting brief glimpses from the top.

In this episode, Scott and Joubin discuss out-of-touch VCs, the challenges of marketplaces, Josh Luber, Dan Gilbert, almost missing flights, gaining perspective, scary blackberry bushes, work-family balance, daily workouts, sleeping on planes, e-commerce in the U.S. vs. China, and digital ownership.

In this episode, we cover:

• Special shoes (01:07)
• Scott’s past jobs at the NYSE, StubHub, and eBay (05:47)
• Detroit and frequent flying (10:02)
• Over-optimizing your time (15:25)
• Why do you climb a mountain? (18:00)
• Scott’s childhood and his own kids (22:39)
• Routines and energy (30:15)
• StockX and the future of e-commerce (36:52)
• Going public (43:24)
• SPACs and NFTs (46:21)
• What’s next? (50:11)
• Persistence (52:06)
• Who StockX is hiring (54:34)

Links:

• Connect with Scott
  • 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