Made It with Connor Tomkies

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/

Creators and Guests

Host
Connor Tomkies
Tweet stories and lessons learned. SupportNinja | Acquired by Boston Ventures. Hear Made It Podcast Here: https://t.co/QjryGKbaKS

What is Made It with Connor Tomkies?

"Made It" is a podcast hosted by Connor Tomkies that delves into the journeys of successful entrepreneurs who have not only built and exited their companies, but who are writing the next chapter of their journeys. The show focuses on the unique challenges and lessons learned while moving beyond the exit, offering insights and strategies for listeners aiming to grow their own businesses. Through engaging conversations with various guests, the podcast provides a blend of motivational stories, practical advice, and insider tips on entrepreneurship, business growth, and personal development.