Grit

Guest: Rachel Pike, COO at Modern Treasury

Payment operations startup Modern Treasury is not afraid to do things in “our own weird way,” says COO Rachel Pike. Its values statement is a 150 word essay, it has gone viral by writing about nerdy ACH payments minutiae, and it has an unusual rule for quarterly internal reviews: No slides. Instead, departments have to write one to two page essay, which are packaged together and then shared company-wide, and with the board. In previous jobs, Rachel laments, she and her coworkers would waste time “pushing pixels” around 50-slide decks. “It [the essay] actually takes more thinking and less hours to put together a summary of, ‘where have we been?’” she says.

In this episode, Rachel and Joubin discuss the state of San Francisco, the value of tradition, hunger to learn, the Draper Fisher Jurvetson split, the opportunity cost of staying put, HIPAA and startups, two-entrepreneur households, career transition coaching, “try before you buy” hiring, learning to be remote, the downside of grasping, and fixing inequalities in compensation.

In this episode, we cover:

• Why Rachel doesn’t like talking about herself (01:20)
• Job-hopping and the Bay Area (02:38)
• Early adopters vs. brilliant innovators (05:16)
• Why Rachel left academia (07:44)
• “I got a phD in startups” (10:24)
• The “nights and weekends” gig at AngelList (14:05)
• Describing startups to aliens (16:50)
• Four years at Grand Rounds (18:28)
• What makes Modern Treasury “modern” (21:51)
• How she got hired as employee #1 (24:16)
• Advice for wannabe early-stage startup workers (30:18)
• “Wonder is contagious” (32:00)
• “Do it right the first time” (35:09)
• Hacker News and other growth levers (38:20)
• The excitement of scaling (40:49)
• Advisors and quarterly planning essays (44:02)
• Forced prioritization (49:20)
• Hard feedback (51:50)
• The working with Rachel doc (54:19)
• How Modern Treasury does comp and bonuses (57:21)
• What’s past is prologue (59:43)
• Who Modern Treasury is hiring and what “Grit” means to Rachel (01:02:00)

Links:

• Connect with Rachel
  • 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: Ashley Kramer, CMO & CSO of GitLab

One day, when Ashley Kramer was an SVP at Alteryx, one of her direct reports hit her with a dose of reality: “She said, ‘I think you are trying to put me on a path to be you, and to have your job. I don’t want any of that.’” Now the CMO and CSO of GitLab, Kramer — who has been a perfectionist since childhood — used to hold her team to the same high bar. But as she’s learned over time, “Not everybody’s gonna have your same ambition. Not everybody’s gonna work as hard as you. It doesn’t mean they’re not good at their job. It just means different things are important to them.”

In this episode, Ashley and Joubin discuss what companies get wrong in CEO interviews, “the three P’s” of company values, loosely held disasters, thinking about the future, “everybody does not want to be like me”, how GitLab does meetings, pre-speech nervousness, context switching, skip-level meetings, credibility with the customer, setting the bar too high, and Naval Ravikant.

In this episode, we cover:

• People, Passion, and Product (04:36)
• Joining companies right after they IPO (07:16)
• Scaling questions (10:28)
• Job-hoppers and ambition (12:06)
• Parents and dinner-table conversations (16:35)
• Coping with perfectionism (19:17)
• Coaching and demotivators (21:36)
• Confident public speaking (26:21)
• How Ashley got out of engineering (32:08)
• Being CPO and CMO of Sisense at the same time (35:49)
• Representing “two constituencies” (38:54)
• Why Ashley has two titles again (44:59)
• The radical transparency of GitLab (47:20)
• Growing pains and becoming interim CTO (51:28)
• Working with founder-CEOs (56:08)
• Tough feedback (58:20)
• Personal and professional OKRs (01:01:15)
• Work-life balance (01:03:33)
• How to network (01:06:10)
• Who GitLab is hiring and the meaning of “Grit” (01:08:58)

Links:

• Connect with Ashley
  • 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: Jen Vescio, Chief Business Development Officer at Uber and founder of Awestruck Ventures

If you were to look at Jen Vescio’s calendar, it might look like a pack of Skittles: Every single one of her meetings is color-coded according to the Insights Color Focus system, which assigns the colors red, blue, yellow, and green based on what methods they emphasize in their work. As the chief business development officer of Uber, Jen has to work with people across that spectrum, and preps for each meeting accordingly.

In this episode, Jen and Joubin discuss the pros and cons of media training, Malcolm Gladwell’s Outliers, “semi-pro” soccer, how to ruin your Uber rating, the “fluorescent light” journey, working at “it” companies before they were disrupted, the art and science of business development, self-awareness vs. understanding others, Sean Bratches, what is your motive?, side letter PTSD, “speed and silence are your two worst enemies,” forced time off, getting buy-in, and why “Uber is wired for trauma.”

In this episode, we cover:

• “Dancing in the moment” (00:54)
• The Olympic Development Program (03:22)
• Jen’s parents (08:15)
• DJing and music in Ubers (10:40)
• Talking to Uber drivers (12:48)
• Retiring from soccer (15:04)
• “The big transition” (17:22)
• The dotcom boom and Jen’s first jobs (20:04)
• Innovation and disruption (22:15)
• Buy, build, or partner (27:24)
• Understanding the “color” of others (35:27)
• How to talk to a “double red” (38:38)
• Insights Color Focus and the color of companies (41:16)
• The Trust Quotient (46:45)
• The biggest deal Jen has brokered (50:17)
• The pressure of big deals (51:46)
• The $350 million deal she botched (55:14)
• Getting burned out on corporate jobs (58:22)
• Big, shiny brands like Uber (01:00:38)
• Mental contracts and taking time off (01:05:07)
• Tough feedback (01:08:24)
• Developing trust internally vs. externally (01:09:48)
• How COVID impacted Uber (01:13:08)
• Where Uber is hiring and what Jen thinks of when she hears the word “Grit” (01:18:16) 

Links:

• Connect with Jen
  • 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: Nikesh Arora, CEO and Chairman of Palo Alto Networks

Nikesh Arora has been in the C-Suite for more than two decades, including a 10-year stint as Google’s chief business officer and — most recently — five years as Palo Alto Networks’ CEO. But the COVID-19 pandemic made him radically reconsider the gap between the executive floor and the rest of the company. “There was a tremendous amount of anxiety and fear and uncertainty,” he says, “and this person I was talking to says, ‘Listen, your job as a leader is to create certainty.’ [...] It’s simple: Tell your employees you have their back.” That’s why, for the past 30 months, Nikesh has been making time to virtually meet thousands of Palo Alto Networks employees on Zoom; he gets candid feedback, communicates company goals, and provides a safe space for everyone to bond.

In this episode, Nikesh and Joubin discuss honest CEOs, not having a career plan, process vs. outcomes, remaining independent inside Google, organizational superpowers, understanding your competitors, “evergreen companies,” the ChatGPT disruption, integrating product and sales, blindfolded communication, Evian water, cloud vs. on-prem security, and problem solvers vs. problem representers.

In this episode, we cover:

• Amazing people at Google (02:15)
• T-Motion and T-Mobile (04:05)
• “You cannot control the outcome” (07:36)
• Growing up in India (11:12)
• 400+ rejection letters (14:38)
• Loving what you do (18:26)
• Joining Google (19:55)
• Sergey Brin and Eric Schmidt (24:16)
• Relocating to “the mothership” (27:01)
• “He’s not Googly enough” (28:26)
• Profit, innovation, and paranoia (31:12)
• Cybersecurity and AI (34:04)
• SoftBank CEO Masa Son (38:54)
• Joining Palo Alto Networks (43:04)
• Hiring as home-building (47:04)
• “Nobody comes to work to screw up” (50:25)
• Product and the power of marketing (53:28)
• Cybersecurity “swim lanes” (56:36)
• M&A strategy (01:01:14)
• The two schools of due diligence (01:05:05)
• Moving past problems (01:07:42)
• Creating certainty for employees (01:10:59)

Links:

• Connect with Nikesh
  • 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

Guests: Alex Smith and Shaun Livingston, former players for the San Francisco 49ers and Golden State Warriors

“I just thought, the best of my life is behind me.” That’s what former NFL quarterback Alex Smith recalls of a devastating leg fracture in 2018 that threatened to end his football career forever. Former NBA guard Shaun Livingston suffered a similar injury early in his career, and both men were told the only way forward might be leg amputation & retirement. They endured through depression, surgeries, and painful physical therapy, and both of them found their way back to pro sports. “I hopped on a bike,” Shaun says. “’Oh, I can do this!’ All right, I hopped on a treadmill. ‘Okay, I can do this.’ You give yourself these small victories that, over time, end up adding up.”

In this episode, Alex, Shaun, and Joubin discuss going pro out of high school, the pressure of expectations, talking about emotions, Joe Namath, gratitude for life, military medical care and “group suck”, the D-League, competing against yourself, losing well, “rah-rah guys,” no-look slants, Tom Brady, Kevin Garnett, and the difference between winning and losing.

In this episode, we cover:

• Alex Smith’s background (01:15)
• Shaun Livingston’s background (02:07)
• Alex on the fear of failure (03:23)
• Shaun on “the opportunity of a lifetime” (07:03)
• Imposter syndrome and burying emotions (10:44)
• Anxiety as motivation (13:41)
• Dysfunctional early seasons (16:10)
• Alex and Shaun’s leg injuries (18:57)
• Depression vs. “small victories” (23:51)
• Alex’s recovery process (25:45)
• Shaun’s stint in the NBA Development League (29:51)
• Teaching yourself to walk (31:58)
• Steph Curry and great leadership (36:19)
• Pat Mahomes and the “final shot” (41:05)
• Tough feedback (44:32)
• Recharging in the off-season (47:09)
• Daily consistency (49:41)
• Who Alex and Shaun think of when they hear the word “grit” (54:05)

Links:

• Connect with Shaun
  • 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: Andre Iguodala, forward for the Golden State Warriors

The average professional basketball career lasts around four years. By the first time Andre Iguodala came to play for the Golden State Warriors, in 2013, he was already on year 10 in the NBA. “All I wanted to do was get somewhere where I just truly enjoy going to work every day,” he says. And on his podcast with Evan Turner, Point Forward, he doesn’t shy away from the fact that being a famous and successful player comes with trade-offs. “When you make it ... you’re lifted up, like ‘you’re here to save us all,’” he explains. “There's so many things that go on with us as athletes that people don't get a opportunity to truly understand because there's two sides.”

In this episode, Andre and Joubin discuss the law of attraction, daily practice, former head coach Mark Jackson, Allen Iverson, the value of sports media, Mahmoud Abdul-Rauf’s Tourette Syndrome, Michael Jordan and Scottie Pippen, the lowest point in Andre’s career, and pivoting to stay alive.

In this episode, we cover:

• What goes through Andre’s head when the game rests on his shoulders (01:17)
• Enjoying work every day and playing under head coach Steve Kerr (05:31)
• Avoiding the newspaper, and why he started a podcast (09:59)
• The trauma of success and basketball as a sanctuary (14:07)
• Playing against LeBron James and with Steph Curry (17:59)
• Being addicted to success and finding joy on the court (21:24)
• Kevin Durant’s work ethic (25:41)
• Are the wins or losses more memorable? (28:30)
• Being a student of the game (32:02)
• Why Andre’s memoir is called The Sixth Man, and what changes in the playoffs (35:34)
• His final season in the NBA, and being a part of the tech ecosystem (42:04)
• The qualities of great players, and the most memorable game of his career (45:50)

Links:

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

Guest: Al Gore, Former Vice President and chairman of The Climate Reality Project

Al Gore has been talking about all kinds of renewable energy for decades. The former U.S. Vice President, Nobel Peace Prize winner, and star of An Inconvenient Truth says it’s “thrilling” to see things like wind power and sustainable forestry becoming the norm. But as humanity continues its struggle against the climate crisis, he says, it’s worth remembering that political will is also a renewable resource. Effective storytellers and political organizers can overcome the entrenched political power of the oil and gas industry, and young people are flocking to work for climate-conscious companies that share their values. 

In this episode, Al and Joubin discuss Abraham Lincoln, Silent Spring, “father of the United Nations” Cordell Hull, downhill skiing, “pursuing a grail,” Watershed, An Inconvenient Truth, the Inflation Reduction Act, trolling Newt Gingrich, former CIA director Bob Gates, “let the glory out,” and Greta Thunberg.

In this episode, we cover:

• Which of Al’s many accomplishments is he proudest of? (01:52)
• What he learned from his parents, a pioneering lawyer and a U.S. Senator — and why he decided to get into politics (05:32)
• Being an underdog and finding the energy to fight injustice (16:15)
• The distinction between work and play, and commitments of the heart (19:28)
• The “hidden truth about human endeavors” (28:05)
• Becoming a great storyteller and getting instant, actionable feedback (31:25)
• Al’s “close as brothers” partnership with President Bill Clinton (36:44)
• Accepting hardship and renewing political will (48:08)
• How does Al renew his own energy? (53:57)

Links:

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

Guest: Giancarlo “GC” Lionetti, CRO of Zapier

“I live in a constant state of paranoia,” says Zapier CRO Giancarlo “GC” Lionetti, “which I guess is healthy and unhealthy.” A lifelong hard worker who shows up early and stays late, GC could have kept his job at team collaboration company Atlassian, which he joined before the company even offered stock options to employees. But his hunger for new experiences — and desire to learn things about new disciplines, like sales — took him away to unexpected new roles at Dropbox, Confluent and now Zapier. “If you asked me in every single experience what my next experience was gonna be ... I wouldn’t have guessed the one that I ended up doing,” he says.

In this episode, GC and Joubin discuss in-person retreats, the problem with “hybrid” cultures, in-office perks, dyslexia and ChatGPT, Atlassian as a “mini-MBA,” re-directing energy to find happiness, self-service businesses, “fitting the mold,” the space for meetings, and dinner at home with the kids.

In this episode, we cover:

• The Grit tip jar and being an “anti-remote” person at a fully remote company (00:47)
• How GC compensates for not being able to walk & talk around the office (06:13)
• The dying art of being early, and GC’s brand of hard work (09:03)
• His father’s exhausting work life, and his first summer job (16:18)
• Is GC a “pusher” or a “puller,” and some crucial advice from Atlassian CEO Scott Farquhar (21:15)
• What he thought in the early days of Atlassian’s ride to the top (27:48)
• What Zapier does and how it has helped GC and his wife as parents (31:29)
• “It was hard to take advice, because nobody understood this world” (34:25)
• Why did GC leave Atlassian for Dropbox? (38:04)
• Passing on paranoia, and is balance required for happiness? (41:16)
• Marketing vs. sales, and the danger of re-running the same playbook in different companies (48:46)
• Fitting into a box, and learning from people with different backgrounds (56:28)
• Why GC doesn’t like traveling very much, and  the place of meetings in Zapier’s GTM organization (01:01:09)
• Separating the “church and state” of work and personal life (01:07:38)

Links:

• Connect with GC
  • 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: Claire Hughes Johnson, author of Scaling People and Corporate Officer at Stripe

Former Stripe COO Claire Hughes Johnson’s new book, Scaling People, is not your typical business book: Informed by her experience scaling one of the most valuable private companies in the world, it’s a tactical reference manual, “almost like a textbook,” aimed at helping managers wrestling with a variety of problems. And one of the big uniting themes is that, to solve anything, they’re going to have to look inwards. “Leadership does not start with the other people in the room,” she says. “It starts with you ... if you don’t know yourself, you are not gonna be very successful, because you have to understand your work style preferences, your habits, your blind spots.”

In this episode, Claire and Joubin discuss in-demand books, Google pre-IPO, headcount as a proxy for success, paranoid mentality, self-driving cars, honoring commitments, the illusion of time, customer insights, “act like a founder,” asking for feedback, prioritizing and saying no, “steady Eddies,” imposter syndrome, fruit on the counter, layering titles, and making time for family.

In this episode, we cover:

• Who should read Claire’s new book, Scaling People, and how she expects them to read it (00:57)
• The challenges of building Stripe in its early days: “It was just consumed by it” (04:51)
• Why she left Google to become Stripe’s COO, and what she did for them as the business was starting to take off (12:34)
• How Stripe hired the best people — including Claire — and how they could have done it even better (17:25)
• Leadership starts with self-awareness (26:05)
• Honest criticism that rocks your world, and taking feedback well (29:43)
• The “unauthorized guide” to working with Claire (36:18)
• Getting hired at Google by Sheryl Sandberg, and why Claire didn’t follow her to Facebook (40:26)
• “Pushers and pullers,” a framework for working with top talent (46:43)
• What entrepreneurs can learn from Condoleezza Rice about impact, passion, and ability (58:33)
• Putting your (imperfect) expertise out into the world (01:02:03)
• Implementing Stripe’s first performance feedback process, and why it still doesn’t “do” titles (01:07:06)
• Having a life outside of work, and the “clarifying moment” of a surprise birthday party (01:15:26)

Links:

• Buy Scaling People: Tactics for Management and Company Building
• Connect with Claire
  • 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: Rania Succar, CEO of Intuit Mailchimp

Ten years out of college, and with two advanced degrees under her belt, Rania Succar knew she wanted to be an operator. Taking a job at Google taught her a lot, but she chafed under the limitations imposed on her control and personal impact. At Intuit, she finally found what she had been searching for: “We really do have a structure that's set up to give you massive amounts of accountability and responsibility.” For seven years, Rania worked across the Quickbooks team before becoming the CEO of Mailchimp in August 2022. And along the way, she also discovered the “beauty” in jointly owning some functions with her teammates: “It can actually be brilliant.”

In this episode, Rania and Joubin discuss immigrant culture, boundless energy, the search for meaning, the illusion of control, getting back to equilibrium, registering your ambition, “Mailkimp,” prioritizing family, sleep experiments, passing the baton, finding problem-solvers, and meetings that give you energy.

In this episode, we cover:

• The importance of family to Syrians, Persians, and immigrants (00:43)
• Navigating two cultures at the dinner table, and Rania’s entrepreneurial father (04:48)
• The arc of her career, and figuring out where she wanted to put her energy (08:59)
• What motivates & energizes her, and what takes energy away (14:28)
• The need to own things end to end, and the beauty of sharing the controls (18:32)
• What Rania has learned over seven years at Intuit, and how she pushes to do more (24:32)
• Mailchimp’s “genius” sponsorship of Serial, and preserving its scrappy culture (30:46)
• How Rania allocates her time every week, and finding “30% more efficiency” (34:13)
• Learning about the importance of sleep “the hard way” (38:45)
• Getting through the early months of COVID and being authentic with her team (43:30)
• Learning from leaders like Intuit’s Bill Campbell and Scott Cook, and defining the “next chapter of exceptional” (46:51)
• How a visual impairment became a source of strength (52:54)
• Setting priorities and being a prisoner of one’s calendar (57:16)

Links:

• Connect with Rania
  • 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