The Failures & Lessons From Building 3 Multi-Million Dollar Businesses; Brian Samson in Conversation with Caitlin Durning
Originally featured on the The End in Mind: Personal Development For Entrepreneurs with Caitlin Durning | Guest: Brian Samson, Founder of Plugg Technologies
The Failure Stories Nobody Tells You About
Caitlin Durning opens most episodes of The End in Mind by asking guests to talk about what actually went wrong, not the highlight reel. When Brian Samson joined the show, Durning referenced one of her most popular episodes ever, an entrepreneur who came on to talk about her donut shop going bankrupt, and noted how much listeners connected with the honesty of it. That set the tone for one of the more candid conversations Samson has had about the parts of entrepreneurship most founders leave out of their pitch decks.
Samson has earned the right to talk about failure because he has racked up plenty of it. Over 11 years as an entrepreneur, he has taken three different companies from zero to $4 million in annual revenue, built a company in Argentina to 80 engineers before exiting, and made more than 500 placements through Plugg Technologies, the nearshore staffing company he now runs from Hawaii. But the businesses that worked are only half the story. The other half, the failed Shopify clothing venture, the expensive salespeople who didn't move the needle, the customer who owed him a quarter million dollars, is where the real lessons live.
Why Founders Get Grace That Salespeople Never Do
One of the sharpest insights in the episode had nothing to do with product or market fit. It was about who is doing the selling. Early in his first venture, a company Samson raised roughly $2 million to build, he hired two expensive salespeople to go out and generate revenue. It didn't work the way he expected. He described the capital as something closer to a crutch, one that let him avoid a skill he needed to build himself.
The reason, Samson explained, comes down to grace. When a founder fumbles a pitch or says the wrong thing, prospects tend to forgive it, because they can tell the person in front of them cares more about the business than anyone else in the room. A hired salesperson doesn't get that same benefit of the doubt. Samson has been the face of his own sales process for a decade now, mistakes and all, and says people still don't seem to mind. It's a distinction worth sitting with for any founder tempted to hire their way out of a sales problem before they've done it themselves.
The Case for Stoicism Over Positivity
Caitlin Durning pushed Samson on how he handles uncertainty, asking directly, "what did you tell yourself in those moments or how did you maybe like prepare for knowing that the next wave was coming," a question aimed at the fear that comes with not knowing if the business will survive its next crisis. Samson's answer leaned away from the productivity-guru script and toward something closer to stoicism.
He described entrepreneurship as a process of getting punched in the face repeatedly, at some point losing all your revenue overnight to something like COVID, or spending a year in litigation trying to collect a debt from a client who owes you a quarter million dollars, and needing to expect it rather than be surprised by it. His point wasn't that founders shouldn't feel anxious. It was that dwelling in the anxiety instead of moving quickly into problem solving is what actually derails people. Every hard stretch, in his framing, compounds into more resilience for the next one, the same way Benjamin Franklin's famous description of compound interest applies to nearly any skill built under pressure.
The Cash Flow Quadrant, and Why Skipping Stages Backfires
Samson leaned on Robert Kiyosaki's Cash Flow Quadrant framework, employee, self-employed, business owner, investor, to explain how he thinks about his own career arc and the mistake he sees other founders make. He has moved through all four quadrants over 11 years, and his advice for anyone earlier in that journey was blunt: don't rush it.
Watching someone else's highlight reel on social media makes it easy to assume they skipped straight to the investor stage. Samson argued that skipping stages produces what he called a half-baked investor, someone who hasn't put in the reps needed to actually evaluate deals well. Whether it takes a founder a year or a decade to move through each stage, he framed the timeline itself as far less important than actually going through it. Caitlin Durning, reflecting on her own path at 30 years old, noted how different her expectations at 23 were from where she has actually landed, a reminder that the timeline rarely matches the plan.
Building a Leverage Machine Out of Labor, AI, and Capital
The most tactical section of the episode was Samson walking through how he evaluates new investments today. He described a personal framework built on four types of leverage: labor leverage through his nearshore talent network at Plugg Technologies, operational leverage through the AI automation company he launched this year, capital built up through years of rental property and business ownership, and what he called wisdom, the accumulated judgment from over a decade of running companies.
His ideal acquisition target is a business with zero of those four things already in place, typically a scrappy, capable operator who is excellent at the craft itself but has no back-office support, no digital presence, and no access to affordable talent. By bringing labor, AI efficiency, and capital to that kind of business, Samson said he can create an immediate lift in valuation without spending much of his own time running day-to-day operations. It's a clear example of how a nearshore staffing model, the same one behind Plugg Technologies, becomes more than a cost play when it's paired with capital and operational expertise.
Why Boring, Old-School Businesses Are the Better Deal
Samson's current portfolio includes a cleaning company and a locksmith business, and he's actively looking at junk hauling and electrical services. The appeal isn't glamour. It's the gap. He estimated that in Hawaii, roughly 95 percent of home service businesses still don't have a website or accept digital payments, and many are still collecting checks by hand. That gap means a business only has to do a little to stand out from the rest of the market.
This is also where his nearshore staffing background pays off in an unexpected way. A cleaning company doesn't need a nearshore hire to clean houses, but it can use one to run pricing, scheduling, digital payments, and customer communication, freeing the on-the-ground team to focus on quality control. Samson pointed out that Plugg's recurring revenue model, built on monthly billing for placed talent, is part of what makes the underlying business itself more valuable if he ever wanted to sell it, since buyers pay for predictable future cash flow rather than a one-time transaction.
What to Do Next
For listeners weighing their own next move, a few concrete takeaways stood out from the conversation:
If you're the founder, be the one selling first. Don't outsource the pitch to a hired salesperson before you've proven you can close deals yourself. Prospects give founders room to make mistakes that they won't give anyone else.
Expect the hard stretch instead of being surprised by it. Build a mental model where setbacks, lost revenue, difficult clients, slow quarters, are normal rather than evidence something has gone wrong.
Don't skip stages in your own Cash Flow Quadrant journey. Put in the reps as an employee, then self-employed, then business owner, before jumping into investing. The timeline matters less than actually going through each stage.
Look for old-school businesses with an obvious digital gap. A missing website or the absence of digital payments is often a sign of an easy, low-cost improvement that can meaningfully shift a business's value.
The Takeaway
What made this conversation different from a typical founder interview was Caitlin Durning's insistence on the parts most guests skip past, the failed ventures, the anxiety, the years it actually takes to get somewhere. Samson's answers add up to a picture of entrepreneurship that has less to do with big swings and more to do with steady compounding, in skills, in reputation, and eventually in the kind of leverage that makes each new venture easier than the last.
🎧 Listen to the full episode: Brian Samson on The End in Mind Podcast
🔗 Learn more about nearshore hiring: plugg.tech
🎙 The Nearshore Cafe Podcast
Brian Samson is the founder of Plugg Technologies and host of The Nearshore Cafe Podcast. This post is based on his appearance on The End in Mind: Personal Development For Entrepreneurs.