A $3.6B founders honest take on the software market right now @MyFirstMillionPod
A $3.6B founders honest take on the software market right now  @MyFirstMillionPod
Uploaded July 2026 | Updated September 2026, 2 weeks ago
*Get Sam and Shaan's hard-won CEO lessons in one guide:* 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.
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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


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Links:
• Box - box.com

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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: joinhampton.com/mfm


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Check Out Shaan's Stuff:
• Shaan's weekly email - shaanpuri.com
• Visit 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 across all of his companies. you can too: mercury.com
Mercury is a fintech company, not an FDIC-insured bank. Banking services provided by Choice Financial Group, Column, N.A., 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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My First Million |

A $3.6B founder's honest take on the software market right now

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