Guest: Bipul Sinha, co-founder and CEO of RubrikWhen 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 2014, he had gone through an epiphany: “Only make decisions that you truly believe is the right thing to do,” he says. “If you are here, at the moment of truth, you want to succeed or lose based on your own terms, not what others feel.”In this episode, Bipul and Joubin discuss how debate moves business forward, companies as living systems, growing up poor, refusing to compromise, risk aversion, finding your own potential, paying tuition, context matters, psychological safety, and smelling the roses.In this episode, we cover:Joubin’s interview with Ali Ghodsi (00:51)The importance of authenticity (02:33)Extreme voices (05:10)Being yourself at work (08:14)Reducing blind spots (11:08)Tough feedback (13:09)Learning entrepreneurship through osmosis (14:41)IIT or bust (19:40)Setbacks and reorienting (23:35)Leaving India for America (26:53)From Oracle to Blumberg Capital (30:21)Prioritizing his own happiness (34:36)“This is a career” (37:08)Dissatisfaction and the next thing (40:37)Creating an enduring institution (45:02)No one knows what they’re doing (49:32)Open board meetings (53:39)Hiring and firing (55:37)Good and bad startup advice (57:58)Working forever (01:01:16)Positive feedback and empathy (01:04:19)Who Rubrik is hiring and what “grit” means to Bipul (01:08:55)Links:Connect with BipulTwitterLinkedInConnect with JoubinTwitterLinkedInEmail: grit@kleinerperkins.com Learn more about Kleiner PerkinsThis episode was edited by Eric Johnson from LightningPod.fm

Guest: Ted Purcell, CRO of TealiumThe 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 more important in a market downturn: “That becomes the main job because the winning is not as evenly spread,” he says. In this episode, Ted and Joubin discuss empty-nesters, resisting leadership, liking to win vs. hating to lose, complete commitment, commitment to culture, hardcore accountability, Israeli conversations, Day-Timers, and endurance battles.In this episode, we cover:Growing up and raising kids in Silicon Valley (00:56)From individual contributor to management (05:03)The appreciation for the grind (08:45)Ted’s father and his sudden passing (10:33)Stepping up to take care of the family (14:40)The Purcell family dinner table conversation (18:22)Working with Bill McDermott at SAP (20:50)Ted’s favorite Bill story (26:00)Getting comfortable as a leader (28:35)(Over-) Optimizing for lifestyle (34:02)How to spot greatness in interviews (37:25)A startup guy at big companies (39:48)Clarizen and corporate culture in Israel (42:10)Tealium and the “pressure cooker” environment (47:36)Believing in the “why” (51:13)Tough feedback and misconceptions (53:47)Recording ideas and daily habits (55:33)Pushing to achieve your potential (57:38)Gaining perspective (01:02:05)Who Tealium is hiring and what “grit” means to Ted (01:05:55)Links:Connect with TedLinkedInConnect with JoubinTwitterLinkedInEmail: grit@kleinerperkins.com Learn more about Kleiner PerkinsThis episode was edited by Eric Johnson from LightningPod.fm

Guest: Jay Parikh, CEO of LaceworkJay 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 when they are 10 minutes late, but they should: “I’m like, no, I disrespected 10 minutes of your time. So I take that really seriously.”In this episode, Jay and Joubin discuss non-traditional CEOs, surviving Facebook’s early days, disrupting yourself, Akamai co-founder Danny Lewin, cultivating culture, applying restless energy, the loneliness of leaders, brushing your teeth, the love of the game, and being approachable.In this episode, we cover:The “S-curve of learning” (01:04)Finding new challenges (05:10)“Is this too big of a job?” (07:33)Intensity and zen (11:00)Jay’s first jobs (15:07)Akamai’s post-IPO pop and crash (16:31)9/11 and Danny Lewin’s legacy (19:56)Facebook’s pivot to mobile (24:58)Managing morale when the share price drops (27:16)Learning from Mark Zuckerberg (30:13)Being on time (34:44)Security in the cloud (37:58)Leaving Facebook (40:01)What has surprised Jay about becoming a CEO (45:00)Hiring, onboarding, and unlocking people (49:34)Jay’s favorite interview questions (54:34)Refusing to compromise on greatness (01:00:44)Balancing work and family (01:07:02)Who Lacework is hiring and what “grit” means to Jay (01:09:06)Links:Connect with JayTwitterLinkedInConnect with JoubinTwitterLinkedInEmail: grit@kleinerperkins.com Learn more about Kleiner PerkinsThis episode was edited by Eric Johnson from LightningPod.fm

Guest: Dave McJannet, CEO of HashiCorpTo 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 workers. But even small choices can create a “cultural crater” that you’ll have to dig yourself out of three months later.In this episode, Dave and Joubin discuss returning to the office, the sales data flow, unstructured problem-solving, why companies grow like trees, anonymous town halls entrepreneurs-in-residence, go to market vs. product, committing to the job, the executive “CPU tax,” and the 30-to-100 phase shift. In this episode, we cover:In-person vs. remote collaboration (00:43)How to build any kind of business (05:26)The value of being in the sales motion (07:30)Thinking like a venture capitalist (11:51)Commiserating with other CEOs (13:28)Systems-based thinking (17:37)Administrators vs. builders (20:25)The daily 10 decisions (22:29)Staving off decision fatigue (24:17)Dave’s past jobs and the path to CEO (26:01)The reluctant CEO (28:46)Rapid change vs. high-profile maintenance (32:20)The pressure of being at the top (35:12)The state of HashiCorp when Dave arrived (37:39)How he got the CEO job (40:38)Product-building POV (45:50)The first “oh shit” moment (48:48)Being motivated by competition (50:47)Laddered time horizons (53:47)Paul Moritz and empathy (55:17)Misconceptions about CEOs (57:10)Deciding to go public (59:45)Time and energy management (01:03:10)Anticipating phase shifts (01:06:12)Fierce independence (01:08:12)Getting the right feedback (01:09:13)Who HashiCorp is hiring and what “grit” means to Dave (01:12:30)Links:Connect with DaveTwitterLinkedInConnect with JoubinTwitterLinkedInEmail: grit@kleinerperkins.com Learn more about Kleiner PerkinsThis episode was edited by Eric Johnson from LightningPod.fm

Guest: Robert Chatwani, President and General Manager of Growth at DocuSignRobert 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, where he finds himself solving the same problems over and over again; but when you’re in a little bit over your head, Robert explains, “that’s a good place to be, because that’s where the best learning comes from.”In this episode, Robert and Joubin discuss trusting your intuition, reinventing yourself, personal boards of advisors, people-powered commerce, betting on people, career coaching, taking time for family, being the same person in every room, bone marrow donors, energy takers vs. creators, and leading with empathy.In this episode, we cover:Networking through venture capitalists (02:18)Leaving high-profile jobs (04:29)How to know when it’s time to leave (07:55)12 years at eBay (11:05)The seeds of doubt (15:10)Finding purpose in company-building (17:51)Robert’s personal mission statement (21:01)Growing up in Chicago and his parents (24:40)Losing a parent (27:16)True North by Bill George (29:35)Finding ways to be human (32:45)What accomplishment Robert is most proud of (34:35)MonkeyBin and meeting eBay (36:08)Sameer Bhatia’s battle with leukemia (38:30)Building a global bone marrow campaign (42:38)“You can’t control every outcome” (48:07)Unexpected side effects (52:56)Business is a force for good (56:26)Working at Spring, and then Atlassian (01:00:01)Self-doubt and leaving Atlassian (01:06:29)Making tough calls with IQ & EQ (01:10:24)Who DocuSign is hiring, and what “grit” means to Robert (01:13:48)Links:Connect with RobertLinkedInConnect with JoubinTwitterLinkedInEmail: grit@kleinerperkins.com Learn more about Kleiner PerkinsThis episode was edited by Eric Johnson from LightningPod.fm

Guest: Ariel Cohen, CEO and co-founder of NavanAs 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 change everything,” he says. “... I disconnected from the news and from some of our investors and from ... negativity and started to lead the company again.” In a way, he explains, it was like a reset to the earliest days of the business, because the only people left were long-term believers like him.In this episode, Ariel and Joubin discuss “tier one” VCs, developing goodwill, company money vs. employee money, wartime CEOs, putting handcuffs on founders, staying dynamic, returning to the office, scuba diving, shared values, Macallan whisky, believing in startups, losing employees, in-person connections, secondary liquidity, and “deposits and withdrawals.”In this episode, we cover:Picking the right investors (01:22)Connecting to the Matrix (04:04)Obsessing over failure (10:29)Reflecting on an eight-year journey (14:56)The benefits of naïveté (17:50)Ariel’s entrepreneur father and early jobs (20:45)Older startup founders (23:03)Getting out of large companies (25:35)Personal burn rate (28:03)Becoming the big company (30:11)Pivoting into AI (32:44)Project Reset and personally resetting (34:12)Making controversial decisions (39:55)“What could I have done better?” (45:43)Ariel’s co-founder Ilan Twig (47:04)What makes a co-founder relationship work? (48:50)Running out of cash (51:18)Being a travel startup during COVID (55:53)The depression quarter (01:00:12)Long-term believers (01:02:54)Why Navan would go public (01:07:55)Startup advice and hard-charging CEOs (01:11:27)What “grit” means to Ariel and who Navan is hiring (01:15:24)Links:Connect with ArielLinkedInEmail: ariel@navan.comConnect with JoubinTwitterLinkedInEmail: grit@kleinerperkins.com Learn more about Kleiner PerkinsThis episode was edited by Eric Johnson from LightningPod.fm

Guest: Seth Dallaire, CRO at WalmartWhen 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,’” Seth recalls. “And they obviously convinced me of that and we’re making really good progress.”In this episode, Seth and Joubin discuss startup success, advertising attribution, “maintenance mode,” online grocery shopping, “the ultimate tailwind,” over-buying, digital vs. traditional retail, founder-led businesses, John Furner and Doug McMillon, sentiment vs. data, getting told “no,” the theory of constraints, and why you should visit Bentonville.In this episode, we cover:Seth’s unique career path (00:59)Amazon’s elite team in 2000 (05:24)Growing up & dinner table conversations (08:25)Work-life balance (10:53)Ambition and achievement (12:08)Investing in yourself (16:04)Recommitting to a role (17:38)Leaving Amazon for Instacart (20:14)Grocery stores are underrated (23:56)Transitioning to a much smaller company (25:33)How COVID accelerated Instacart’s business (27:54)Advertising is a full-contact industry (32:03)Getting recruited by Walmart (34:06)Visiting Walmart stores with other execs (40:08)A leadership lesson from Doug McMillon (43:10)Product orientation (45:40)Compounding knowledge capital (47:57)Tough feedback (50:19)Leaving a team behind (54:34)Hand-written notes (56:04)The Goal and On the Shortness of Life (57:35)Relocating and refueling (01:00:40)Who Seth is hiring and what “grit” means to him (01:02:25)Links:Connect with SethLinkedInConnect with JoubinTwitterLinkedInEmail: grit@kleinerperkins.com Learn more about Kleiner PerkinsThis episode was edited by Eric Johnson from LightningPod.fm

Guest: Matt Mochary, CEO of Mochary MethodMatt 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 Brian Armstrong (CEO Coinbase), Bastian Lehmann (CEO Postmates), Sam Altman (CEO OpenAI), and Steve Huffman (CEO Reddit). All the money earned from that work, he says, bypasses his bank account and is funding the development of software that will teach tech workers the “Mochary Method.”In this episode, Matt and Joubin discuss information asymmetry, GPT-4, focusing on fun, coaching software, saving people, the slums of Rio and the South Bronx, surfing vs. friends, the merits of crappy solutions, why companies fail, shadowing the CEO, feedback and resentment, pissing people off, the danger of “excellence,” and energy audits.In this episode, we cover:Putting in effort, finding value (01:11)OpenAI CEO Sam Altman (05:43)Immediate responsiveness (09:48)“Mount Rushmore” referrals (11:54)When Matt’s coaching was free (15:08)His Hungarian grandfather and World War II (19:56)The hero complex (25:12)Stepping away from the game (31:30)Billionaires and inner peace (38:45)The phases of company-building (40:54)The problems Matt helps leaders solve (47:48)“It’s fun to be a founder!” (54:35)Craving feedback (56:48)The zones of excellence and genius (01:02:19)“Today, what went right?” (01:09:12)Growing too early (01:12:32)Who Matt is hiring and what “grit” means to him (01:15:00)Links:Connect with MattTwitterLinkedInConnect with JoubinTwitterLinkedInEmail: grit@kleinerperkins.com Learn more about Kleiner PerkinsThis episode was edited by Eric Johnson from LightningPod.fm

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 competitive advantage. Retreating from freight was “painful,” Shoaib recalls, but helped the company extend its existing lead in trucking — and may have saved the whole business. In this episode — joined by special guest Ilya Fushman from Kleiner Perkins — Shoaib and Joubin discuss curiosity for the world, first impressions, reorienting yourself, electronic logging devices, directly connecting with customers, growing up as a CEO, waiting for the market, having a “low discount rate on the future,” the physical economy TAM, AI dash cams, and pricing in risk, and running out of runway.In this episode, we cover:Shoaib’s Pakistani parents and doing extra homework (01:17)Explaining and experiencing startups (04:26)“High standards are infectious” (08:15)What Motive does (10:08)How Shoaib and Ilya met (10:54)The origins of Motive as “Keep Truckin’” (14:06)Working with friends (17:27)First-time founders (21:56)Deep empathy for users (24:01)Monetization and second-guessing (25:48)Sudden success and scale (29:12)Recruiting top talent (31:04)Shoaib and Ilya’s personal-professional relationship (32:07)“I knew the board I wanted” (34:32)Motive’s failed expansion into freight (36:21)Realizing and correcting the error (39:26)How to make smarter future bets (44:09)Second and third products (47:29)Back to the core mission (50:36)Autonomous driving vs. AI assistants (52:17)Thinking about competition (55:05)A tough conversation about runway (58:52)Sticking your neck out for your partner (01:04:09)Losing Ilya as a board member (01:06:23)Who Motive is hiring (01:08:32)What “grit” means to Shoaib (01:09:32)Links:Connect with ShoaibTwitterLinkedInConnect with IlyaTwitterLinkedInConnect with JoubinTwitterLinkedInEmail: grit@kleinerperkins.com Learn more about Kleiner PerkinsThis episode was edited by Eric Johnson from LightningPod.fm

Guest: Tom Hale, CEO of OuraWhen he was growing up, Tom Hale’s family had pretty ordinary dinner-table conversations: What happened today, how was school, etc. But every day after dinner, Tom and his father would play backgammon, an experience that indirectly taught him a lot about business. Now the CEO of wearable health company Oura, he recalls that the game helped him understand risk-taking, strategy, pattern recognition, and more. Tom’s father also insisted they play for money: “If I could win 20 bucks, I could go down to the store and get something. But when I lost, I felt the sting of it. That’s the best teacher, because you’re learning the preciousness of the decisions you make.”In this episode, Tom and Joubin discuss Tom’s radio voice, games of chance and skill, vacation rentals pre- and post-Airbnb, “irritant” service fees, health tracking, the psychology of rebranding, the consumerization of healthcare, personalized medicine, the myth of the founder-hero, rowing machines, and the meaning of work.In this episode, we cover:Returning to the office (00:50)John Doerr and Macromedia (05:15)Post-dinner backgammon (08:01)Tom’s past jobs and HomeAway (11:31)Competing against private startups (16:09)How Airbnb captured demand (18:55)Being acquired by Expedia (24:26)What Oura’s smart rings do (26:13)Rebranding SurveyMonkey to Momentive (29:55)Leaving Momentive for Oura (31:54)Making the case for himself (34:59)The future of public health, data, and wearables (37:10)“Sleep is strategic” (42:32)Why Oura is an AI company (44:48)The health impact of a taxing job (47:16)Being a non-founder CEO (49:39)Working with people (53:38)What would be in a “working with Tom” doc? (54:52)Managing the psychology of a 10-year-old startup (56:48)Being there for family & colleagues (59:18)Who Oura is hiring, and what “grit” means to Tom (01:02:54)Links:Connect with TomTwitterLinkedInConnect with JoubinTwitterLinkedInEmail: grit@kleinerperkins.com Learn more about Kleiner PerkinsThis episode was edited by Eric Johnson from LightningPod.fm