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My First Million

The Richest People I Know Do One Thing

Episode 785: Shaan Puri talks to Nick Huber about the biggest bet he ever made and the mistakes he learned the hard way.

Shaan PurihostNick Huberguest

Jan 15, 202654mWatch on YouTube ↗

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CHAPTERS

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Chapter summaries

Nick Huber’s “humbling” era: when the market stopped being easy
Shaan sets up the episode as Nick publicly walking through major mistakes rather than only wins. Nick explains how his earlier confidence came from a period when growth felt easy, and how the last few years forced a more sober view of how hard business really is.
- •Shaan frames the conversation around learning from mistakes rather than highlight reels
- •Nick contrasts his earlier “knew everything” mindset with current humility
- •Nick says business felt easy in prior years, but recent years have been materially harder for entrepreneurs
- •Nick attributes some prior success to irrational confidence he still values
From 11 companies to a power-law portfolio: what got shut down and why
Nick and Shaan discuss Nick’s burst of starting many companies and the reality that several didn’t work out. Nick describes a power-law outcome where a few businesses drive most results while others stalled or closed.
- •Nick says he started 11 companies, including agencies and service businesses
- •He names several ventures (e.g., AdRhino, Huber Method, a business brokerage) as part of the expansion phase
- •Nick says four companies have been shut down and two are treading water
- •He notes current group cash flow is higher now, driven by a small number of winners
The Somewhere acquisition origin story: competing with (then partnering with) Andrew’s bid
Shaan recounts the internal backstory of the acquisition offer for the company (then Support Shepherd/Shepherd), including a proposed purchase by Andrew Wilkinson. Nick explains why he didn’t want to sell and decided to try to buy a controlling stake instead.
- •Shaan describes Marshall receiving an acquisition offer and leaning toward taking it
- •Shaan and Nick both preferred holding their stake rather than swapping for another company’s stock
- •Nick recalls deciding he wanted more of the business, not an exit
- •Nick describes the moment as “peak” confidence and ambition
Deal structure and terms: raising $20M and negotiating a seller note
Nick breaks down how deal terms determined whether the acquisition made sense for him. He explains the initial structure, why the economics didn’t work, and how he restructured it by negotiating seller financing to increase his ownership and upside.
- •Nick says the acquisition price moved to $52M as the business grew during the process
- •He explains raising $20M to buy roughly 40% would only yield limited upside for him under a carry structure
- •Nick says he concluded the deal was foolish unless he could buy more ownership
- •He negotiated an 18% seller note from Marshall (about $9M), bringing total capital to roughly $29M
New owner syndrome in action: the name change that wiped out a third of leads
After taking control, Nick describes major rapid changes—starting with rebranding and a domain purchase. The move from Support Shepherd to Somewhere.com caused an immediate collapse in SEO and brand recognition, reducing inbound leads sharply.
- •Nick says the company renamed because “Shepherd” was frequently misspelled
- •They bought Somewhere.com for $400,000 shortly after closing
- •Nick says SEO and brand recognition vanished overnight after the domain switch
- •He reports losing about 300 leads per month out of roughly 1,000
Traffic collapse, platform risk, and competition: Twitter changes + loud announcing backfired
Nick attributes further headwinds to major changes in social distribution and increased competitive pressure. He says Elon Musk’s Twitter changes reduced his ability to drive leads from his personal brand, and that publicizing the acquisition helped invite new competitors.
- •Nick says the Twitter algorithm shift reduced his ability to generate visits and leads from tweets
- •He describes going from large lead spikes to “virtually nothing” from social posts
- •Nick says many competitors entered international hiring over the following months
- •Shaan notes the acquisition announcement produced a short-term growth burst but also intensified competition
Macro headwinds and aggressive exec changes: expanding beyond the Philippines
They describe how the customer base became more cautious as the economy shifted, reducing hiring demand. Nick also recounts making bold operational and executive changes—expanding hiring focus into new geographies and higher-skilled roles.
- •Nick cites macro shifts (including higher interest rates) reducing hiring across customer segments
- •Shaan explains their customers were cost-sensitive “real businesses,” not heavily VC-subsidized spenders
- •Nick describes shifting beyond a Philippines-heavy focus into Latin America, South Africa, and Egypt
- •He frames the post-acquisition period as a broad operational expansion into higher-skill hiring
The recovery: growth returns, but behind pro forma expectations
Nick provides the “spoiler” that the business recovered and is growing again. He shares comparative growth figures and emphasizes how much he learned about worldwide recruiting while rebuilding momentum.
- •Nick says recent months are up about 60% in revenue compared to the pre-acquisition period he references
- •He says revenue is up 28% year over year
- •Nick notes he’s still behind his original pro forma expectations
- •He emphasizes learning and improved global recruiting execution
Building international executive teams (and how to hire globally without Somewhere)
Nick and Shaan explain how they shifted from thinking global hiring was only for junior roles to using it for leadership and specialized positions. Nick then lays out a step-by-step sourcing and filtering process, including simple screening tactics and practical assessments.
- •Nick shares team composition across businesses, emphasizing very few Americans outside sales/account roles
- •He says he’s found senior operators and heads of functions in places like South Africa and Colombia
- •Nick outlines a DIY global hiring funnel: promoted LinkedIn job posts, then fast filters
- •He describes two key screens: typing speed and requiring a one-minute intro video, followed by role-based assessments
Assessments over interviews: Shaan’s example task list for hiring an assistant
Shaan gives concrete examples of paid, task-based trials designed to simulate real work and reveal communication and execution quality. He explains how clarifying the ‘test’ also clarifies what the employer truly needs—reducing bad hires driven by likability in interviews.
- •Shaan describes using Loom-based task demos to evaluate candidates’ process and communication
- •He shares example tasks: planning travel options, drafting emails from a voice note, conducting practical research, and creating a Canva card
- •He argues most interview processes fail because employers don’t know what they’re looking for
- •Nick adds that strong candidates quickly stand out with minimal effort from the employer
One thing done relentlessly: the richest operators “hammer” one play for years
Nick describes being impressed by operators who find one thing that works and repeat it for years without chasing trends. Shaan connects this to Peter Thiel’s view that too many revenue streams or acquisition channels often signals the absence of one truly great engine.
- •Nick says he’s impressed by someone building a major company by running the same play for years
- •He emphasizes that many big outcomes come from doing one thing exceptionally well
- •Shaan recounts Thiel’s idea that listing many channels/revenue streams can be a negative signal
- •They discuss examples of focusing on a single strong distribution channel and a single monetization method
Suli’s “brutal” focus rule and the CEO’s real job: saying no
Shaan shares a story about being told not to pursue new channels until the current one is scaled to a clear benchmark. Nick mirrors this with an example of refocusing executives on the most profitable channel rather than forcing paid ads to work.
- •Shaan recounts being told to avoid ‘influencers’ until Facebook ads hit a specific scale milestone
- •He explains how focusing on what’s already working prevented distraction and compounded results
- •Nick contrasts a low-profit paid ads channel with a high-profit referral engine in one company
- •Nick concludes a key CEO role is repeatedly saying no and focusing the team on what works
Holdcos are overrated + consistency wins: fewer fires, longer horizon
Nick argues that running multiple businesses is often underestimated and that most people who do it well mastered one company first. He and Shaan discuss durability, avoiding burnout cycles, and the advantage of steady execution over short intense sprints.
- •Nick says many aspiring holdco builders underestimate the skill required to run multiple companies
- •He contrasts real estate’s relative predictability with operating companies’ revenue volatility
- •Nick says multiple companies create constant problem escalation to the owner
- •They emphasize even-keeled consistency and long-term compounding over boom-and-bust intensity
The ‘one big thing’ method, creator treadmill fears, and Nick’s AI skepticism
Shaan explains his daily routine of identifying and focusing on a single high-impact task, arguing it outperforms scattered hustle. They then discuss how video dominates modern content growth, why the creator hamster wheel feels difficult, and Nick’s belief that AI is overhyped and constrained by energy costs—despite long-term potential.
- •Shaan describes his two-hour ‘one big thing’ focus block and why it compounds over time
- •Nick says content creation increasingly requires video and worries about the ongoing treadmill of weekly performance
- •Nick calls AI overhyped in the near term while acknowledging long-term impact
- •He cites rising energy costs and data center buildout as a central concern and says many AI tools didn’t justify their cost in his businesses
Blue-collar margins and real estate cycles: roofing spreads, storage carnage, and what’s next
Nick and Shaan discuss unsexy businesses with attractive economics, using roofing as an example of selling and managing subcontracted work for a spread. They transition to self-storage and broader real estate stress from rising interest rates, and Nick closes with what he plans to focus on going forward.
- •Nick explains roofing economics: selling the job, subcontracting labor, and capturing the spread
- •Shaan shares an example of a contractor choosing Alaska to face weaker competition
- •Nick explains why higher interest rates create real estate ‘carnage’ by doubling debt service costs and reducing what buyers can pay
- •Nick says his team refinanced without investor capital calls, improved conversion via South African sales talent, and plans to focus on Somewhere, RE Cost Seg, and more storage acquisitions

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