When everything works, you learn the wrong lessons

Summary of When everything works, you learn the wrong lessons

by Hubspot Media

56m•January 15, 2026
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Overview of "When everything works, you learn the wrong lessons" (HubSpot Media)

This episode features Nick Huber (guest) interviewed by Sean. Nick—known for a brash, confident online persona—walks through a humbling multi-year business arc: the acquisition of Somewhere (formerly Shepherd), a string of startup wins and failures, and what he learned running and rebuilding companies during changing markets. The conversation covers deal structure, mistakes made in the acquisition, how to hire and scale internationally, how to focus a business, views on holdcos and AI, and practical hiring tactics you can use immediately.

Main themes & big-picture takeaways

  • Success in a bull market can teach the wrong lessons. Early wins led Nick to overconfidence; tougher macro conditions exposed fragile assumptions.
  • Deal terms matter as much as price. Raising capital to buy equity can materially change economic upside for the acquirer.
  • Rebrands and platform dependence are real risks. A name change and social algorithm shifts cost material leads.
  • Global hiring is not just for repeatable tasks—high-quality executive roles can be sourced internationally for far lower cost.
  • Hire by production, not charm. Task-based assessments and paid trials massively reduce bad hires.
  • Focus and consistency win: double down on a single distribution channel that works before diversifying.
  • Holdcos are harder than they look; most wealthy founders focus deeply on one durable business.
  • Be skeptical about the near-term business ROI of many AI plays (Nick is skeptical about sustainability and energy costs), while acknowledging long-term transformational potential.

Notable stories & episode highlights

  • The Somewhere acquisition:

    • Original offer from Andrew Wilkinson around a $47M valuation; final $52M purchase price.
    • Nick decided to buy rather than sell; financed the deal via outside investors (~$20M) plus a seller note carved from the founder (about 18% equity for ~$9M).
    • Structure implications: raising money changed Nick’s economics (carry and dilution), prompting creative seller financing to increase his ownership.

  • Three immediate post-acquisition shocks:

    1. Rebrand from Shepherd → Somewhere: lost ~300 leads/month and much SEO momentum.
    2. Elon Musk’s Twitter changes: Nick’s ability to drive traffic from his personal brand collapsed.
    3. Competition + macro: competitors rushed in and the broader economy got tougher (higher interest rates, more cost-conscious customers).

  • The recovery:

    • Despite setbacks, revenue grew year-over-year; the company rebuilt by recruiting high quality talent across global markets (South Africa, Colombia, Egypt, Sri Lanka, Philippines).
    • Nick learned executive roles (COO, finance, performance marketing) can be filled internationally with high competency and lower cost.

Practical, actionable hiring playbook (step-by-step)

  1. Post and promote the job on LinkedIn:

    • Suggested markets: Colombia, Brazil, South Africa, Philippines (general roles); Egypt for finance/data; Eastern Europe for engineers.
    • Promote with ~$100/day for 5 days → expect ~1,000 applicants.

  2. First filters (automated, fast):

    • Typing-speed test: remove candidates below ~30–35 WPM (85% fail this filter in Nick’s experience).
    • One-minute intro video: removes non-serious applicants (many won’t do it).

  3. Task-based assessment (paid):

    • Give a 60–90 minute production task that mirrors real work. Request a Loom or recorded walkthrough to capture thought process and communication.
    • Examples of assistant tasks Nick uses:
      • Book a trip with options (cheap / balance / luxury).
      • Draft emails from a voice note.
      • Research 10 influencers that match criteria.
      • Create a birthday card mockup in Canva.
      • Solve DMV/licensing / logistics with incomplete instructions.
    • Pay for the task/trial hour(s) to respect candidate time and get honest, committed submissions.

  4. Final interview & hire:

    • Compare outputs, not anecdotes. Hire the person who produced the best task outcome and demonstrated communication and professional maturity.

Tactical business & leadership lessons

  • Terms over headline price: if you need outside capital to buy equity, understand carry, hurdle rates, and how much upside you actually get.
  • Beware “new-owner syndrome”: don’t change everything at once—name changes, brand moves, major executive turnover can fracture existing growth engines.
  • Double down on what works: find the single distribution channel that scales (Peter Thiel’s point) and obsess on it before adding distribution diversification.
  • Consistency > bursts of mania: adopt sustainable rhythms (Nick’s “one big thing” — 2 hours focused at start of day) rather than all-nighters and chaotic sprints.
  • Holdco caution: running multiple operating companies requires deep operational skill; leverage and cyclical risk can make it fragile if done prematurely.
  • Real estate sensitivity: rising interest rates dramatically increase carrying costs; operational efficiency and conservative leverage are critical.

Nick’s hot takes (notable quotes)

  • “Everyone’s a genius in a bull market.”
  • “Task test over interview.”
  • “Go where there’s fish, but not other fishermen.”
  • “The tortoises win in life.” (consistency beats manic bursts)
  • “If you have to raise $20M to buy 40% of a company, your carry and upside change materially—structure matters.”
  • “AI is bullshit and unsustainable and will decrease quality of life for the 99%” (Nick is skeptical of short-term business ROI and worries about energy costs, while acknowledging long-term transformation).

Quick checklist — what to do next (if you run or hire for a small/scale-up business)

  • If buying a company: map the financing and carry scenario (who gets made whole first, your carry, seller notes, dilution).
  • Before rebranding: audit SEO, lead volume and consider a migration strategy—name changes can cost material organic traffic.
  • Build a repeatable hiring funnel: LinkedIn ads + typing test + 1-min video + paid task trial.
  • Pick one distribution channel that already works and double down until diminishing returns, then expand.
  • Think long-term on AI — run small, measured experiments and track real cost vs. benefit (and consider energy/hosting costs).
  • For real estate acquisitions: stress-test modeled cash flows under higher interest rates before bidding.

Episode bottom line (one-paragraph summary)

Nick Huber uses a candid post-mortem of a high-profile acquisition and several portfolio experiments to argue for humility, focus, and rigorous operational processes. He shows how early success can mask structural weaknesses (brand dependence, financing dilution, overconfidence), and offers practical hiring templates and company-building advice: hire by production, choose one distribution channel and work it relentlessly, be conservative about deal structure and leverage, and treat global hiring as a scalable, high-quality resource—if you build a proper funnel and assessment process.

Guest: Nick Huber. Host: Sean (episode sponsored by HubSpot).