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Business influencers love to talk about their wins. The internet is awash with charts showing exponential growth, successful exits, and flawless execution. It is far rarer to find a successful entrepreneur willing to eat "humble pie" publicly, dissecting their failures and the brutal lessons learned from near-catastrophic mistakes.
In a candid conversation, Nick Huber opens up about the reality behind his online persona. Known for his "Sweaty Startup" brand and bold opinions, Huber details the turbulent acquisition of Somewhere.com (formerly Shepherd), the collapse of his marketing channels, and why he has pivoted from a diversification strategy back to extreme focus. Beyond the mistakes, he lays out a sophisticated, battle-tested playbook for global hiring that challenges the traditional US-centric employment model.
Key Takeaways
- The danger of arrogance in acquisitions: Success in one domain does not guarantee success in another, and rebranding a company can destroy its SEO and organic lead flow overnight.
- Global talent arbitrage is evolving: The real opportunity isn't outsourcing low-level tasks; it is hiring high-level executives, financial controllers, and sales leaders from countries like South Africa and Colombia.
- The "One Big Thing" method: To escape the trap of reactive work, dedicate the first two hours of every day to a single, high-impact task before checking email or metrics.
- Holding companies are overrated: Running a portfolio of mediocre businesses creates exponentially more problems than running one great business.
- Contrarian market views: Why AI might be a bubble due to energy costs and why "boring" businesses in uncrowded markets (like framing in Alaska) offer the best risk-adjusted returns.
The Acquisition That Humbled a Founder
Success can be a dangerous drug. After launching over ten companies in a few years and building a massive personal brand, Huber felt invincible. This confidence led him to intervene in the acquisition of Shepherd, an outsourcing agency. Originally slated to be sold to tech investor Andrew Wilkinson, Huber stepped in, convinced he could buy the company, rebrand it, and scale it to the moon.
He raised capital, structured a complex deal involving seller financing, and took the reins. Then, reality hit. In a move driven by branding aesthetics rather than data, he changed the company name from "Support Shepherd" to "Somewhere.com."
"Changed the name from SupportShepherd.com to Somewhere.com. Our SEO, our search engine optimization, and our brand recognition vanished overnight. In that one fell swoop, we lost 300 leads a month."
The timing could not have been worse. Simultaneously, Elon Musk acquired Twitter and altered the algorithm, destroying Huber’s ability to drive organic traffic to the business. Interest rates spiked, causing the company’s core customer base—bootstrapped businesses and agencies—to freeze hiring. Huber went from "genius in a bull market" to fighting for the company's survival.
The turnaround didn't come from a magic hack, but from stabilizing operations and accepting that business is cyclical. The experience served as a tuition payment for a lesson in humility: brand power has limits, and fundamental execution matters more than hype.
A New Playbook for Global Talent
While the acquisition was rocky, it forced a complete reimagining of how to build teams. The traditional outsourcing model focuses on finding low-cost virtual assistants in the Philippines for repetitive tasks. Huber’s new approach focuses on executive arbitrage.
He discovered that high-level talent—people with MBAs, CPA equivalents, and decades of experience—could be hired in specific international markets for a fraction of the cost of their US counterparts. This isn't about cheap labor; it is about mispriced elite talent.
Geographic Specialization
Huber has identified specific hubs for specific skill sets:
- South Africa: The premier hub for sales and finance. Culturally similar to the UK and US, with excellent English. You can hire experienced financial controllers or sales leaders who can close high-ticket deals.
- Colombia and Brazil: Ideal for operations and performance marketing. They share US time zones, making collaboration seamless.
- Egypt: A powerhouse for finance and data analysis, specifically for high-level Excel and PowerBI work.
- The Philippines: Remains the standard for administrative tasks and high-volume support, deeply ingrained in the culture of working with US firms.
The Filtering Process
Most employers fail at remote hiring because they cannot handle the volume of applicants. Huber’s companies receive 60,000 applications a month. To filter this down to the top 1%, he uses a ruthless, automated funnel:
- Typing Speed Filter: 85% of applicants are rejected immediately because they cannot type 35 words per minute. In a remote environment, typing speed is a proxy for computer literacy and communication efficiency.
- Video Introduction: Applicants must submit a one-minute video introduction. This tests English fluency, professional maturity, and willingness to do the work. This cuts the remaining pool by another 80%.
- Paid Task Assessment: Resume interviews are notoriously unreliable. Instead, candidates are given a paid task that mimics the actual job—booking travel with fuzzy instructions, analyzing a P&L statement, or researching influencers.
"The person who is competent will shine to the top of the crowd without any work on your end. It's a beautiful thing."
The Myth of the HoldCo and the Power of Focus
For several years, the "HoldCo" (Holding Company) model was the trend du jour in entrepreneurship circles. The idea was to own a portfolio of varied businesses—a newsletter, an agency, a SaaS, and a real estate portfolio—all synergizing together.
Huber, once a poster child for this movement, now argues that for 99% of entrepreneurs, this is a trap. Diversification often disguises a lack of conviction in your primary business. When you split your attention across ten companies, you don't get ten streams of income; you get ten unique sets of crises.
This realization led to the "One Big Thing" productivity method. Instead of the "hustle culture" badge of honor—sleeping in the office and working 80-hour weeks—success comes from sustained, focused intensity on the single most important driver of revenue.
The Protocol:
- Identify the one task that actually moves the needle (e.g., fixing the sales script, analyzing the P&L, hiring a key executive).
- Dedicate the first two hours of the morning to this task exclusively. No email, no Slack, no social media.
- If you accomplish nothing else the rest of the day, you have still won the day.
"The person who wakes up every day... identifies the proper single thing that matters and puts full focus on that one thing... they will crush the average person who simply doesn't even identify the one big thing."
Contrarian Takes: AI Skepticism and Boring Businesses
In a tech landscape obsessed with the next big thing, Huber remains bullish on the unsexy and the tangible. He offers a sharp critique of the current AI boom, comparing it to the dot-com bubble. While he acknowledges the long-term potential, he views the current capital expenditure as unsustainable, specifically regarding energy consumption.
Data centers are driving up energy costs in municipalities across the US, creating a physical bottleneck that software cannot code its way out of. For the average business owner, the ROI on AI tools is often negative. Huber notes that he implemented 15 AI tools across his portfolio and canceled 13 of them because they simply didn't deliver business value.
The "Weak Competition" Thesis
If AI is the crowded trade, where is the opportunity? It lies in markets with low supply and weak competition. Huber cites the example of a framer who left the saturated California construction market to work in Alaska. By going where it was inconvenient for others to go, he secured higher margins and less competition.
This principle applies universally: look for the "roofing broker" opportunities where you can connect demand with supply in fragmented, non-digital industries. The richest people often aren't the ones inventing new technology; they are the ones running the same boring play consistently for two decades.
Conclusion
The shift from "arrogant genius" to "humble operator" is a transition many entrepreneurs face, usually in private. By sharing the stumble publicly, Huber highlights a critical truth: business resilience isn't about never failing. It is about surviving the failures, killing the distractions, and having the discipline to do the boring work consistently over a long time horizon. Whether it is hiring a controller in Cape Town or fixing a roof in Georgia, the fundamentals of margin, focus, and persistence remain undefeated.