Grit

Guest: Pedro Franceschi

Pedro Franceschi is the co-founder and CEO of Brex, a fintech company reshaping how businesses manage their finances.

Originally from Brazil, Pedro went from teenage hacker to leading one of the most well-known names in modern financial technology—building a platform trusted by startups and enterprises alike.

In this episode, Pedro shares what it took to launch “Brex 3.0,” why he moved to a single-CEO model, and how tough structural changes set the stage for leaner, faster growth.

Chapters:
00:00 Trailer
00:46 Introduction
01:45 Startup roller coaster
05:21 Founders know how to have fun
07:12 Belief barrier evolution
12:00 Early state of life in Brazil
13:23 Controlling variables
15:32 Screen time
19:23 Making small decisions
23:27 Learning raises the bar
26:15 People manager
38:49 Getting underwater
42:05 Growth accelerated
47:51 Vision from the top down
52:13 Leadership organization
54:01 AI software engineering physics
54:43 People complain about change
59:42 Believers and non-believers
1:04:09 Equity and bonus controversy
1:08:40 Big swings and going public
1:14:15 Control in unpredictability
1:18:04 Living in a pixel

1:19:52 Meditate, sleep, diet, exercise

1:24:36 Mental health and stress
1:33:12 Who Brex is hiring
1:33:49 What "grit" means to Pedro
1:34:39 Outro

Mentioned in this episode: Silicon Valley, Facebook, Meta Platforms, Inc., Mark Zuckerberg, Mastercard, Rio de Janeiro, iPhone, Bill Gates, Tim Urban, Jony Ive, Apple Inc., LinkedIn, Salesforce, Brian Chesky, Airbnb, Anthropic Claude, Cursor, Codeium Windsurf, Cognition Labs Devin, Vercel, Retool AI, Amplitude, Spenser Skates, Elon Musk, Tesla, Inc.

Links:

Connect with Pedro:

Guest: Zac Bookman, CEO and Co-Founder of OpenGov

Thirteen years after co-founding the government transparency startup OpenGov, Zac Bookman is still finding ways to surprise people. In 2024, Cox Enterprises bought the company for $1.8 billion — but as far as Zac is concerned, “we’re just getting started.”

“ I left the vast majority of my net worth in the company,” he says. “So I'm a believer. I'm all in.”

The mission of powering “more effective and accountable government” has been stable since OpenGov’s earliest days, and that mission has informed everything from hiring to M&A to the decision to sell.

 “These people buy and don't sell,” Zac said of Cox. “They're all in on the mission. And they're all in on taking care of employees. So I see a triple win: A win for employees, win for the investors, win for the customers, maybe a quadruple win for me and the management.”

Chapters:

• (01:46) - OpenGov’s mission
• (04:34) - Shrinking the product-market fit
• (07:34) - Super misson driven
• (08:59) - Why OpenGov almost shut down
• (13:08) - Zac’s early career
• (16:16) - Picking (and losing) a CTO
• (22:50) - Growing upside-down
• (25:29) - The SPAC backstabber
• (31:26) - Why Zac didn’t get fired
• (33:24) - Selling in 2024
• (37:04) - Growth by acquisition
• (42:31) - John Chambers and PMF
• (49:32) - Zac’s cross-country bike ride
• (56:25) - Expectations vs. reality
• (58:57) - The coup attempt
• (01:01:59) - Tiring work
• (01:05:47) - Going to the White House
• (01:09:40) - DOGE & disrespect
• (01:12:54) - “We’re just getting started”
• (01:14:18) - Who OpenGov is hiring (and where)
• (01:15:13) - What “grit” means to Zac

Mentioned in this episode: Joe Lonsdale, Cox Enterprises, OpenAI, the Department of Government Efficiency, Workday, H.R. McMaster, Stanford University, Formation 8, 8VC, the National Academy of Sciences, the Stanford Review, Kamala Harris, Marc Andreessen, Balaji Srinivasan, Coinbase, Earn, Ben Horowitz, Facebook, Steve Laughlin, Cisco, Laurene Powell Jobs, Glynn Capital, Acme, Allen & Company, Harry You, Joe Tucci, EMC, Bill Green, Accenture, Tyler Technologies, HP, Josh Kushner, GTY Technology Holdings, John Keker, Palantir, CKAN, Oracle, Kevin McCarthy, The American Technology Council Summit, Jeff Bezos, Tim Cook, Satya Nadella, Pat Gelsinger, Donald Trump, Jared Kushner, Elon Musk, Bill Clinton, and Al Gore.

Links:

Connect with Zac

Guest: Ben Chestnut, Former CEO and Co-Founder of Mailchimp

If you find yourself selling your startup, then Mailchimp co-founder Ben Chestnut has some important advice for you: Get a dog. 

When Intuit bought Mailchimp in 2021 for $12 billion, the company asked Ben if he wanted to stay on as CEO, but he chose to “walk off into the sunset” and let the new owners take over. 

After that, he estimates it took 6 to 12 months before he stopped checking his email, social media, and calendar with the same level of stress a CEO might have. Adopting a dog, he discovered, forces you to “get OK with the voices in your head."

“After the acquisition, that's all I do, I walk the dog,” Ben says. “And the dog was good therapy ... No judgments from a dog.”

Guest: Blake Scholl, Founder & CEO of Boom Supersonic

“Passion and drive trumps knowledge and experience,” says Boom Supersonic CEO Blake Scholl. Long before he was running Boom — which earlier this year successfully tested the world’s first privately-developed supersonic jet — he was enabling “the world’s most obnoxious spam cannon” at Groupon, or designing a barcode-scanning game for retail shoppers.

But eventually, Blake found the courage to be more audacious and do something closer to his lifelong love of aviation. He began educating himself about things he had never thought to learn, and tapping his LinkedIn network to get intros to the smartest people in the industry. 

“If you imagine yourself on like the day of IPO, 99 percent of what you needed to know to get to that day, you didn't know on day one,” he says. “So, why not take 99 percent to 99.5 percent, and work on the thing you really want to exist, even if you don't know anything about it yet?”

Chapters: 

• (01:07) - Blake on Boom’s beginnings
• (01:52) - Breaking the sound barrier
• (05:23) - Concorde’s legacy
• (09:36) - Navigating regulations
• (12:08) - Boomless supersonic flight
• (16:48) - The test flight
• (20:11) - Day-of nervousness
• (24:26) - Carrying passengers
• (26:55) - Cost & wi-fi
• (30:19) - “No middle seats”
• (32:35) - Hard tech
• (36:48) - What if Apple made a plane?
• (39:08) - Blake’s career journey
• (43:29) - The risk of failure
• (49:12) - Finding the courage
• (52:49) - Balancing life with Boom
• (56:42) - Learning how to build a jet
• (01:00:20) - The power of LinkedIn
• (01:02:38) - Y Combinator Demo Day
• (01:08:24) - Richard Branson
• (01:11:38) - Dividing yourself
• (01:14:19) - Being a focused dad
• (01:20:05) - Exuberance vs. fear
• (01:24:15) - Hiring slowly
• (01:27:17) - What “grit” means to Blake

Mentioned in this episode: Chuck Yeager, ChatGPT, the Apollo program, Elon Musk, SpaceX and Falcon 1, Boom Overture, Starlink, Boeing, Airbus, iPhone, Jony Ive, Uber, Airbnb, Anduril, United Airlines, American Airlines, Eclipse Aviation, Tesla, Scott Kirby, Mike Leskinen, Inktomi, Yahoo!, Amazon, Pelago, Google Ads, Kima Labs, Barcode Hero, Groupon, iPad, Eric Schmidt, Steve Jobs, Khan Academy, Sam Altman, Loopt, Virgin Atlantic, Paul Graham, Michael Seibel, Ashlee Vance, Bloomberg, Hacker News, Jared Friedman, Sen. Mark Kelly, SV Angel, Ron Conway, Virgin Galactic, Lockheed Martin, Gulfstream, Jeff Bezos, Jeff Holden, and How It’s Made.

Links:

Connect with Blake