Kleiner Perkins Grit Podcast

What’s the real luxury: a business class bed at 40,000 feet or a supersonic jet that gets you there in half the time? Blake Scholl believes it’s the latter. The Boom Supersonic founder reveals why aviation’s future hinges on a rebel who can outtalk the skeptics, outsmart the physics, and outlast the odds. With just a 10% fuel efficiency edge over Concorde, he’s chasing a trillion-dollar market where time is the ultimate luxury. Can an industry outsider really bring back supersonic flight, or will the legacy giants reclaim the future they abandoned? Full episode linked in the comments.xx

What’s tougher: raising a billion-dollar company or walking away from it? Ben Chestnut, Mailchimp’s founder, carved a 20-year empire—no investors, only his rules. How did a bootstrapper outlast VC darlings and still quit on top? Full episode linked in the comments.

Ever come within days of shutting down your startup? Zachary Bookman, CEO of OpenGov Inc., knows the feeling. Three days from closing the doors, with no product and no cash, he was desperate. A Christmas spent slogging through a thick finance book sparked a tiny win—a $1,800 deal. Fast forward 12 years, and that relentless grind paid off. OpenGov just sold for $1.8 billion. What changed? Hear the full story from Zac, hosted by Joubin Mirzadegan, on Grit.

A few of our upcoming guests on Grit: 1) Ryan Petersen, Flexport 2) Pedro Franceschi, Brex 3) Jay Chaudhry, Zscaler 4) Chris Urmson, Aurora ???Episodes drop every week on Monday morning!

?? Tune in to our CEO Zachary Bookman's interview on Kleiner Perkins Grit Podcast! Join Zac and host Joubin Mirzadegan as they explore the early days of OpenGov, share inspiring stories of resilience, and discuss the grit required to build a business focused on powering a more effective and accountable government. Listen here: https://lnkd.in/gvP9iCUU YouTube: https://lnkd.in/gm8ZrcjC Spotify: https://lnkd.in/gBpsdACE Apple https://lnkd.in/gvP9iCUU #Leadership #Entrepreneurship #StartupJourney #GovernmentInnovation #BusinessInsights #CEOInterviews #Resilience #Grit

It was great to join Joubin Mirzadegan on Kleiner Perkins Grit Podcast. We dove into the origins of OpenGov, and I told stories about the pain and confusion of growing a software company and building leadership.? If you’ve never listened to “Grit,” it’s an amazing podcast about the mistakes, failures, and learnings endemic to entrepreneurship, business, and trying to do big things with teams.? Thank you Joubin!? I’m grateful to work with 2000 governments across America with incredible, mission-driven people at OpenGov.? And fired up for all the challenges and opportunities ahead.? Take a listen and let me know what you think! YouTube: https://lnkd.in/gSrZsfGY

Zachary Bookman spent more than a decade building OpenGov Inc. into a leader in cloud software for local governments—then landed a $1.8 billion acquisition by Cox Enterprises. He founded the company with Joe Lonsdale backed by investor and board member John Chambers, and built a team driven by a passion for public service. On the Grit podcast this week, Zac shares why building software for governments isn’t the typical Silicon Valley dream, how they navigated tough challenges, and why being mission-driven made all the difference. Full episode on YouTube and all your favorite podcast platforms below ??

Why cram in shaky "beds" when 3 hours beats 10? Blake Scholl, founder of Boom Supersonic is capping Overture at 64 seats, chasing business-class profits over overnight frills. His take on airline flatbeds? Useless when flights hit 3 hours. Passengers want time, not turbulence naps. To unpack Blake Scholl’s strategy for finding a product market fit, tune in to the full episode—link in the comments.

What started as a web gig for Ben Chestnut, turned Mailchimp mainstream, fueled by 20 years of grit and a knack for turning chaos into cash without ever raising a penny from VC’s. The catalyst? Fun, creative ads and a well timed Saturday Night Live shoutout. Full episode linked in the comments.

Mailchimp Co-Founder Ben Chestnut built one of the most successful bootstrapped companies ever—then walked away at the top. After selling Mailchimp to Intuit for $12 billion, Ben had the option to stay on as CEO but chose a different path. On the Grit podcast this week, he shares what it was like to step away, how long it took to truly disconnect, and why his best advice for founders selling their companies is simple: Get a dog. “No judgments from a dog.” Full episode on YouTube and all your favorite podcast platforms below ??