How “Boring” Businesses Make Big Money with Nick Huber (& Alex Lieberman)

Entrepreneur and investor Nick Huber joins Connor Tomkies and Alex Lieberman to break down how he built a $100M+ empire starting with sweaty, unsexy businesses like student storage. They discuss his new book The Sweaty Startup, the trap of chasing big ideas too early, and why momentum, urgency, and simplicity often beat innovation. From self-storage to buying a $50M company, Nick shares tactical advice, brutal honesty, and hilarious truths about what it really takes to make it. Plus: how Alex is building his own HoldCo, and why AI isn’t eating their businesses just yet.

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Nick's Book!
 
Chapter Markers:

[00:00:00] Introducing Nick Huber & Alex Lieberman
[00:01:00] The Sweaty Startup Philosophy
[00:02:30] Building Skills Before Innovation
[00:03:30] Sales as a Foundational Skill
[00:05:00] Knowing When to Quit
[00:06:30] Urgency and Speed in Business
[00:08:00] The Power of Momentum
[00:09:00] Redefining Success and Leverage
[00:10:30] Life After $20K a Month
[00:12:00] Embracing the Hedonic Treadmill
[00:13:00] Huber's Business Timeline
[00:15:00] Raising Capital and Scaling Up
[00:16:30] Lessons From Starting Ten Companies
[00:17:30] Avoiding Bottlenecks as a Founder
[00:18:30] Holding Companies vs. Private Equity
[00:20:00] Ownership Philosophy and Exit Strategy
[00:21:00] Optimizing for Joy or Growth
[00:22:30] Buying Businesses and Taking Swings
[00:24:00] Challenges and Wins With Somewhere.com
[00:25:30] Offshoring Strategy and Market Dynamics
[00:27:00] Global Hiring Trends and Niches
[00:29:00] AI, Automation, and Agency Moats
[00:31:00] The Value of Cold Emails
[00:32:00] Leveraging AI for Lead Gen
[00:34:00] Building Distro as a Product Funnel
[00:35:30] Why AI Tools Are Just Getting Started
[00:37:00] Hunting for Business Ideas
[00:39:00] Filtering Good vs. Bad Ideas
[00:41:00] Dangerous and Unsustainable Businesses
[00:42:00] Nick’s Next Chapter in Entrepreneurship
[00:43:30] Final Thoughts From the Group

Nick's Stuff:

Website: https://sweatystartup.com/
X: https://x.com/sweatystartup
Podcasts: https://sweatystartup.com/podcast/
Youtube: https://www.youtube.com/channel/UCBYwRdRw6x9bH4PsyCLnmOw

Alex's Stuff:

Website: https://foundersjournalpod.morningbrew.com/
X: https://x.com/businessbarista
LinkedIn: https://www.linkedin.com/in/alex-lieberman/

My Stuff:

Podcast: https://www.madeitpod.com/
Website: https://www.connortomkies.com/
X: https://twitter.com/ConnorTomkies
LinkedIn: https://www.linkedin.com/in/connortomkies/