Podcast Summary: My First Million – "When Everything Works, You Learn The Wrong Lessons"

Date: January 15, 2026
Hosts: Sam Parr, Shaan Puri
Guest: Nick Huber

Episode Overview

In this candid and insightful episode, Sam and Shaan welcome entrepreneur Nick Huber for an unusually vulnerable conversation. While most business podcasts focus on wins and success stories, this episode explores Nick’s humbling business journey, mistakes made, and hard-learned lessons from running and acquiring multiple companies—highlighted by his high-profile acquisition of somewhere.com (formerly Support Shepherd). The discussion ranges from the perils of overconfidence in bull markets, lessons about focus and consistency, tactical hiring advice, and sharp opinions on modern business trends like AI, holdcos, and content creation.

Key Discussion Points & Insights

1. The Fallacy of Perpetual Success

• Overconfidence in Boom Years

  • Nick reflects on his mindset during the 2020-2023 boom (01:30):

    "I thought business was easy... I thought customers just came... I thought I could do no wrong because I had this personal brand started. All these companies started, 10 plus companies over a three year period." — Nick (02:20)

  • Many businesses prospered due to favorable market conditions, but those conditions didn’t last.

• Failure and the Power Law Curve

  • Out of 11 companies founded, Nick shut down four, with two barely treading water. Only a few ("three-headed monster") drive the majority of success (03:46–04:36).

2. Behind the Scenes of a Big Acquisition

• The Somewhere.com Acquisition Story

  • Nick tells the full, unvarnished story of acquiring what became somewhere.com, sharing the high-wire deals, creative structuring, and the many ways things went off-script (06:31–12:19).
  • The risks of negotiating against experienced buyers and raising lucrative seller notes:

    "It was a $47 million valuation. The company was three years old and growing really fast... This was peak Nick Huber, not humble Nick Huber of thinking I can do anything and I can't go wrong." — Nick (06:31)

• Strategic Mistakes Immediately After Acquisition

  • Rebranding from Support Shepherd to somewhere.com severely damaged their SEO and web traffic, cutting leads by one-third overnight (11:47–12:19).
  • The collapse of Twitter’s organic reach (Elon Musk buying Twitter, algorithm changes) dramatically reduced Nick’s ability to drive leads through his personal brand (12:25–12:54).
  • The market became crowded with new competitors, a direct result of the public acquisition (13:06).
  • Economic headwinds hit key client bases—agencies, e-commerce, home services, and real estate—making lead growth and spending harder (13:43–15:03).
  • Despite these missteps, the company rebounded:

    "Over the last four months... up about 60% from a revenue perspective and over last year it's 28%. So... revenue is growing very healthily and our team is awesome." — Nick (15:40)

3. Hiring & Talent: Tactical, Global, and Surprising

• Revolutionizing Executive Teams with Global Talent

  • Nick shares how he built high-level teams practically entirely outside the US—COOs in South Africa, finance leads in Egypt, marketers in Colombia, etc. (18:45–19:38).
  • The only truly irreplaceable US-based talent: sales and account management ("can't replicate the American's ability to close high-ticket deals").

• How to Hire Internationally—Exact Playbook

  • Job postings: Target countries—Colombia, Brazil, South Africa, Philippines. Use LinkedIn job ads ($100/day for five days = ~$2K for 1,000+ applicants) (19:50–20:36).
  • Filtering:
    • 35 WPM typing test filters out 85% (20:57).
    • One-minute intro video: 80% drop-off (21:01–21:24).
    • Assessment-based (task) tests over traditional interviews. Use simulations that closely resemble day-to-day work (22:01–24:05).
    • Example task list: booking travel, transcribing from a voice note, handling DMV processes, graphic design, and research (24:05–26:12).

    "The person who's competent will shine to the top of the crowd without any work on your end." — Nick (26:16)

• Country Specialization Cheat Sheet

  • Egypt: Finance/data analysis (Excel, Power BI)
  • Colombia/Brazil: Ops roles on US time zones
  • South Africa: Sales/finance; many big-four-trained auditors
  • Sri Lanka, Philippines: General virtual assistant roles

4. The Danger of "Many Plays" vs. "One Thing That Works"

• The Illusion of Layering Revenue Streams

  • Nick and Shaan discuss Peter Thiel’s "Blake Masters" notes concept:

    "If they tell me seven [revenue streams]... all that tells me is they don't have one amazing thing." — Shaan (29:10)

  • The best companies tend to find and double down on a single distribution channel or revenue stream before branching out.

• Saying NO: The Key to Focus

  • Stories on ignoring distractions and "shiny object syndrome":

    "The job of a CEO sometimes is literally just to tell your team no and to get them focused on what's already working." — Nick (34:18)

  • Consistent, repetitive execution on proved channels is undervalued—success is more about durability and compounding than fireworks (41:00–43:22).

5. Trends & Takedowns: HoldCos, Consistency, Content, and AI

• HoldCos Are Overrated

  • "You really got to know your shit to run more than one company... things can go really wrong, really quick." — Nick (36:04)
  • Most truly wealthy people focus on one thing for a long time; the complexity of multi-business portfolios is often underestimated.

• The Superpower of Consistency

  • Marathoners, not sprinters, win in the long run—counterintuitive in a culture obsessed with overnight success:

    "If you can just keep from gaining weight the first time, it's gonna be a lot easier to stay healthy the rest of your life... stay focused on one business... you can really win." — Nick (37:28)

• Content Creation: The YouTube Trap

  • Entering YouTube/video-first content is now table stakes for growth, but the hamster wheel is daunting and exhausting:

    "As an entrepreneur, I'm really hesitant to get on that hamster wheel... You gotta follow it up the next week and the next week... How would that look for 10 years?" — Nick (44:02)

• AI Skepticism

  • "AI is bullshit and unsustainable and will decrease quality of life for the 99%." — Nick (44:38)
    • Current business impact underwhelming—most tools are cost-inefficient, useful for productivity but not transformative.
    • Cost concerns: surging energy bills due to massive data center demand.
    • Parallel drawn to electric vehicles—progress slower and costlier than hyped.

6. Real Estate, Niche Arbitrage & Blue Collar Wisdom

• Find Weak Competition, Even If It's Unfamiliar

  • Stories about friends finding prosperity by working in overlooked markets (framing in Alaska, self-storage six hours away from home)

    "The secret to winning in life is weak competition... Go where there’s fish but not other fishermen." — Shaan (50:02)

• Real Estate Carnage Explained

  • Rising interest rates have hammered cashflow/valuations; survival requires inventiveness and efficiency.

    "There's guys that are going broke in real estate right now in real time that I know. It's total carnage... luckily we've done some things operationally..." — Nick (54:04)

• Looking Forward

  • Nick plans to double down on his core businesses, with a newly humble and focused approach:

    "My ego has written a lot of checks... now I've got to go cash them. I'm pretty focused on growing somewhere. I want to grow recost seg and I want to buy more storage." (55:01)

Notable Quotes & Memorable Moments

| Timestamp | Speaker | Quote | |-----------|---------|-------| | 02:20 | Nick | "I thought business was easy. I thought building executive teams was easy. I thought customers just came. I thought I could do no wrong..." | | 11:47 | Nick | "We bought somewhere.com for $400,000... changed the name... our SEO vanished overnight. In that one fell swoop, we lost 300 leads a month."| | 19:38 | Nick | "I used to think like, okay, I need repeatable tasks and I need to outsource those... Now I'm realizing that the people who can run my company can do it better and cheaper internationally."| | 29:10 | Shaan | "When they have seven revenue streams... all that tells me is they don't have one. Great one." | | 34:18 | Nick | "The job of a CEO sometimes is literally just to tell your team no and to get them focused on what's already working."| | 44:38 | Nick | "AI is bullshit and unsustainable and will decrease quality of life for the 99%."| | 50:02 | Shaan | "The secret to winning in life is weak competition. Go where there's fish but not other fishermen."| | 55:01 | Nick | "My ego has written a lot of checks... now I've got to go cash them." |

Timestamps for Key Segments

• The Humbling of Nick Huber & Bull Market Lessons..................................[01:30]
• Breakdown of the Somewhere.com Acquisition Story..................................[06:31]
• Mistakes Made (Name Change, Algorithm Loss, Competition).........................[11:47 – 14:18]
• How to Build a Global Executive Team & Hire Internationally........................[18:45 – 24:05]
• CEO’s Real Job: Doubling Down on What Works.......................................[29:10 – 34:18]
• HoldCos, Consistency, and Long-Game Wisdom.........................................[36:04 – 43:22]
• Social Media & YouTube: The Relentless Grind........................................[43:32 – 44:38]
• Nick’s Sharpest Take: AI as Overhyped, Costly Bubble................................[44:38 – 47:36]
• Niche Opportunities & Weak Competition..............................................[50:02 – 52:25]
• Real Estate Challenges in a High-Interest-Rate World...............................[53:04 – 54:50]
• Nick's Refocused Future............................................................[55:01]

Final Thoughts

Tone: Humorous, self-deprecating, direct
Vibe: Real talk about hard lessons, willingness to admit mistakes, actionable advice

This episode is highly recommended for anyone interested in entrepreneurship “warts and all”—especially those who want wisdom beyond the highlight reels. Nick Huber’s story and Shaan’s honest probing offer a rare peek behind the curtain of what happens when everything seems to work—until it doesn’t—and how to recover when you’ve believed the wrong business lessons.

For more:

• Go to somewhere.com for vetted global talent
• Contact Nick for specific candidate shortlists: nick@sweatystartup.com