Guest: Matt MacInnis, COO of Rippling

One of the most important things a non-founder can do, says Rippling COO Matt MacInnis, is to learn how to operate in the context of the company they’re joining. His CEO, Parker Conrad, “spikes” in certain skill areas, and the rest of the executive team needs to maximize his ability to thrive while “taking care of the rest of it.” Matt likened the work to being a hobbyist airplane pilot, who can’t get a license without knowing all the minute details about their plane’s engine and aerodynamics.

“You can’t be a good pilot if you don’t understand the engine, because if something goes wrong, you want to be able to troubleshoot it,” he says. “An executive coming in to fly your airplane better learn the engine.”

Chapters:

• (01:08) - Telling Rippling’s story
• (04:27) - Founding & failing at Inkling
• (09:30) - Different types of hard
• (13:55) - Discipline and stamina
• (15:22) - Meeting with Steve Jobs
• (19:20) - Definitely, give up!
• (22:29) - Product-market fit
• (27:15) - Founders and culture
• (33:24) - Executive instincts
• (36:06) - Talent Signal and AI
• (40:06) - 150 former founders
• (44:08) - Zero to one projects
• (48:06) - The failure of Silicon Valley Bank
• (55:25) - Routines and discipline
• (59:37) - Disagreeing with Parker
• (01:02:25) - Who Rippling is hiring
• (01:03:37) - What “grit” means to Matt

Mentioned in this episode: Parker Conrad, London Breed, Apple, Sequoia Capital, Sapphire Ventures, Tenaya Capital, digital textbooks on iPad, Oricom, Netscape, Peter Cho, Eddy Cue, John Couch, iBooks, Slack, Airbnb, Paul Graham, Brian Chesky, “founder mode,” Larry Ellison, Ivan Zhao and Notion, Intel and ARM, Salesforce, United Airlines, LLMs, GitHub, DocuCharm, Peter Thiel, Mamoon Hamid, Expensify, Navan, Costco, Comcast, HBO’s Silicon Valley, Jensen Huang and NVIDIA, and Taylor Swift.

Links:

Connect with Matt

• LinkedIn
• Twitter

Connect with Joubin

• Twitter
• LinkedIn
• Email: grit@kleinerperkins.com

Learn more about Kleiner Perkins

This episode was edited by Eric Johnson from LightningPod.fm

Guest: Jason Kilar, former CEO & co-founder of Hulu and former CEO of WarnerMedia

When Jason Kilar was a child, he was obsessed with Walt Disney — not just as a filmmaker or the creator of Disneyland, but as an entrepreneur. He started his career at the Walt Disney Company (where else?) but then got his first opportunity to help build something new when a young startup entrepreneur from Seattle visited his business school classroom. Most of Jason’s classmates predicted the failure of this startup, Amazon.com, which elicited “this awesome laugh, the Jeff Bezos trademark laugh.” How a leader reacts to criticism or doubts, Jason learned, says a lot about their conviction and intelligence.

Chapters:

• (01:08) - Bing Gordon and John Doerr
• (04:11) - Warner Bros.
• (06:12) - Walt Disney
• (11:10) - Working at Disney
• (14:32) - What makes it special
• (18:31) - Meeting your heroes
• (20:06) - “Walt’s folly,” Disneyland
• (22:45) - Harvard and Amazon
• (25:09) - Meeting Jeff Bezos
• (29:10) - “Help people understand Amazon exists”
• (33:25) - Amazon’s culture
• (38:07) - What Warner Bros. makes
• (40:55) - Obscurity and relevance
• (45:53) - Feeling the lows
• (50:09) - Launching Hulu
• (53:36) - NewCo or ClownCo?
• (59:13) - Over-communication
• (01:03:14) - The future of TV memo
• (01:06:46) - Innovator’s dilemma
• (01:08:57) - No labels
• (01:14:04) - Unfinished business
• (01:16:22) - Staying present
• (01:20:26) - The theatrical window
• (01:26:19) - What’s next?

Mentioned in this episode: Amazon, The Matrix, Star Wars: A New Hope, Disney World, Diane Disney Miller, Honey, I Shrunk the Kids, Michael Eisner, Universal Studios and Harry Potter, Disney University, Jeffrey Rayport, Barnes & Noble, Joel Spiegel, David Risher, Joy Covey, Garry Trudeau and Doonesbury, Andy Jassy, Brian Birtwistle, Jim Kingsbury, Vessel and Verizon, HBO, Friends, Hogwarts Legacy, Sony, Netflix, NBCUniversal, Paramount, AT&T, Discovery, Richard Tom, Kara Swisher, Fox, YouTube and Google, Saturday Night Live, Peter Chernin, Jeff Zucker, Bob Iger, Andy Rachleff and Benchmark, CBS, Miracle on 34th Street, Marissa Mayer and Yahoo, Rony Abovitz and Magic Leap, House of the Dragon and Industry, Dune, Christopher Nolan, and the TSA.

Links:

Connect with Jason

• Twitter
• LinkedIn

Connect with Joubin

• Twitter
• LinkedIn
• Email: grit@kleinerperkins.com

Learn more about Kleiner Perkins

This episode was edited by Eric Johnson from LightningPod.fm

Guests: Joe Thomas, CEO and co-founder of Loom; and Ilya Fushman, partner at Kleiner Perkins

Loom CEO Joe Thomas had a lot of things to think about before he sold his company to Atlassian for $975 million: The impact an acquisition might have on the product, how to keep the Loom brand alive, the risk of remaining independent... but it wasn’t until after the deal was announced that he really understood what it meant for his team.

“I didn't know how emotional it'd be for me,” Joe says. “All of the Loom employees, current and former, that reached out when this was announced, they did their calculation and they're like, ‘Oh my God.’ That, to me, was the most emotionally transformative part of the process. I didn't fully recognize what that would be like, on the individual front.”

Chapters:

• (01:34) - The Atlassian acquisition
• (05:25) - The bittersweet moment
• (08:15) - Transforming Loom
• (13:30) - Ilya’s perspective
• (18:04) - Life-changing
• (22:55) - Doing it again
• (25:00) - Loom’s early days
• (28:26) - The Series A
• (32:33) - Turning on monetization
• (35:37) - The Series B
• (37:05) - Loom AI
• (43:13) - Revenue orientation
• (48:18) - The acquisition landscape
• (52:27) - Working inside Atlassian
• (54:04) - Atlanta tech
• (55:00) - Who Atlassian is hiring
• (55:24) - What “grit” means to Joe

Mentioned in this episode: Wilson Sonsini, Vinay Hiremath, Andrew Reed and Sequoia Capital, Zoom, Mike Cannon-Brookes, Shahed Khan, COTU Ventures, Andreessen Horowitz, Scott Farquhar, the Lindy Effect, SVB, Google Chrome, Dropbox, Slack, Snapchat, HubSpot, the Van Westendorp Price Sensitivity Meter, Dylan Field and Figma, Atlassian Rovo, Palo Alto Networks, Salesforce, and Garrett Langley and Flock Safety.

Links:

Connect with Joe

• LinkedIn
• Twitter

Connect with Ilya

• Twitter
• LinkedIn

Connect with Joubin

• Twitter
• LinkedIn
• Email: grit@kleinerperkins.com

Learn more about Kleiner Perkins

This episode was edited by Eric Johnson from LightningPod.fm