*Get Sam and Shaan's hard-won CEO lessons in one guide:* https://clickhubspot.com/wqe5
Episode 838: Sam Parr ( https://x.com/theSamParr ) and Shaan Puri ( https://x.com/ShaanVP ) talk to Aaron Levie ( https://x.com/levie ) talk about building Box, getting rich slowly, why AI might make us work harder.
—
Show Notes:
(0:00) Story of Box
(06:30) Enterprise Over Consumer
(10:00) Turning Down Huge Acquisition Offers
(17:05) Angel Investing, Missed Bets, and Investing in Your P&L
(23:00) Aaron’s Contrarian AI Takes: More Jobs, More Work
(30:00) Founder Anxiety, Therapy, and Surviving the CEO Grind
(38:45) The Business Strategy Books Aaron Swears By
(48:00) AI Tools, Software Stocks, and Why SaaS Isn’t Dead
—
Links:
• Box - https://www.box.com/
—
Check Out Sam's Stuff:
• Hampton (joinhampton.com): My community for founders. Average member does $25m/year. Many of the guests are members. Get after it...apply: http://joinhampton.com/mfm
—
Check Out Shaan's Stuff:
• Shaan's weekly email - https://www.shaanpuri.com
• Visit https://www.somewhere.com/mfm to hire worldwide talent like Shaan and get $500 off for being an MFM listener. Hire developers, assistants, marketing pros, sales teams and more for 80% less than US equivalents.
• Mercury - Shaan uses Mercury for banking across all of his companies. you can too: http://mercury.com/
Mercury is a fintech company, not an FDIC-insured bank. Banking services provided by Choice Financial Group, Column, N.A., and Evolve Bank & Trust, Members FDIC
• I run all my newsletters on Beehiiv and you should too + we're giving away $10k to our favorite newsletter, check it out:
beehiiv.com/mfm-challenge
My First Million is a HubSpot Original Podcast // Brought to you by HubSpot Media // Production by Arie Desormeaux // Editing by Ezra Bakker Trupiano /
I dropped out of college and built a $3.6B company from scratch
Imagine dropping out of college with no clear plan, then building a $3.6 billion company from scratch. That’s exactly what happened to the founder featured in My First Million. He saw an opportunity in a crowded market, took the plunge — despite everyone telling him to stay — and focused on solving a real problem. According to the podcast, what sets successful founders apart isn’t just their ideas but their grit, resilience, and willingness to pivot. The story shows that even unconventional paths can lead to massive success if you’re willing to work hard and learn as you go. And here’s where it gets interesting — his journey wasn’t about overnight fame but about relentless execution and trusting his instincts. As My First Million points out, dropping out was the start, not the end. The big takeaway? Sometimes, you’ve got to break the rules to build something truly extraordinary. That shift is subtle now, but it’s exactly the kind of signal that usually defines the next big thing.
Audio Transcript
*Get Sam and Shaan's hard-won CEO lessons in one guide:* https://clickhubspot.com/wqe5
Episode 838: Sam Parr ( https://x.com/theSamParr ) and Shaan Puri ( https://x.com/ShaanVP ) talk to Aaron Levie ( https://x.com/levie ) talk about building Box, getting rich slowly, why AI might make us work harder.
—
Show Notes:
(0:00) Story of Box
(06:30) Enterprise Over Consumer
(10:00) Turning Down Huge Acquisition Offers
(17:05) Angel Investing, Missed Bets, and Investing in Your P&L
(23:00) Aaron’s Contrarian AI Takes: More Jobs, More Work
(30:00) Founder Anxiety, Therapy, and Surviving the CEO Grind
(38:45) The Business Strategy Books Aaron Swears By
(48:00) AI Tools, Software Stocks, and Why SaaS Isn’t Dead
—
Links:
• Box - https://www.box.com/
—
Check Out Sam's Stuff:
• Hampton (joinhampton.com): My community for founders. Average member does $25m/year. Many of the guests are members. Get after it...apply: http://joinhampton.com/mfm
—
Check Out Shaan's Stuff:
• Shaan's weekly email - https://www.shaanpuri.com
• Visit https://www.somewhere.com/mfm to hire worldwide talent like Shaan and get $500 off for being an MFM listener. Hire developers, assistants, marketing pros, sales teams and more for 80% less than US equivalents.
• Mercury - Shaan uses Mercury for banking across all of his companies. you can too: http://mercury.com/
Mercury is a fintech company, not an FDIC-insured bank. Banking services provided by Choice Financial Group, Column, N.A., and Evolve Bank & Trust, Members FDIC
• I run all my newsletters on Beehiiv and you should too + we're giving away $10k to our favorite newsletter, check it out:
beehiiv.com/mfm-challenge
My First Million is a HubSpot Original Podcast // Brought to you by HubSpot Media // Production by Arie Desormeaux // Editing by Ezra Bakker Trupiano /
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