Tech on Tap May 2026 Recap
Tyler Robertson's Journey from Garage Startup to $100 Million
Tyler Robertson, founder and CEO of Diesel Laptops, opened this month's Tech on Tap with a number that still doesn't feel real to him: $100 million in annual revenue. But his story didn't start with venture capital, a tech accelerator, or even a grand vision of building an empire. It started with a newborn son, a pile of debt, and a desperate search for a side hustle that actually worked.
The Accidental Beginning
Years ago, Tyler was like most people, essentially living paycheck to paycheck. After discovering Dave Ramsey's debt elimination philosophy, he started looking for ways to make extra money. Working in commercial truck dealerships his whole life, he stumbled across a Canadian software developer on eBay who had created a diagnostic program for commercial trucks. The website was dated, but Tyler saw an opportunity.
He put together a package: the software, a laptop, and the hardware needed to connect to commercial trucks. He listed it on eBay for $2,000 without actually buying any of the components. He went to bed, woke up the next morning, and it had sold. He pocketed about $1,000 cash overnight. So he did it again, marked it up, and it sold again.
The $100 Million Decision
As the side hustle grew, Tyler found himself working two full-time jobs. Then his boss made him an offer: double his bonus, 10% raise, but he had to shut down his side business. The dealership saw him as competition.
Tyler had a one-year-old, a three-year-old, a stay-at-home wife, and was the sole income earner. His dad told him to take the safe road and shut it down.
But his ex-wife asked him a question that changed everything: "What's the worst that happens if it doesn't work?"
Tyler thought about it. They had six months of cash saved. If it failed, he'd find another job. That was it. Once he got the fear out of his head, the decision became easier. He quit and went all in on Diesel Laptops.
That first year: $1.2 million in revenue. The next year: $3.5 million. Then $7.5 million, $16 million, $32 million. They landed on the Inc 5000, the Inc 500, and became the fastest growing company in South Carolina.
The Blueprint (Sort of)
Tyler admits he can't blueprint the explosive growth for everyone, but but he can break it down into a few core principles.
Relentless focus on sales and marketing. From day one, Tyler committed to doing at least one thing every single day to rank higher on Google and position himself as the industry expert. That work continues today.
Listen to what customers are actually asking. It wasn't about answering questions, but about understanding why customers were asking those questions in the first place. The first product was a diagnostic tool. Then customers needed troubleshooting guides, wiring diagrams, and training. So Diesel Laptops built all of it. Now they run training centers across the US, teaching people how to fix trucks, not just use software.
Even today, Tyler personally calls customers who give low NPS scores. "What did we screw up? What could we have done better?"
Find your why – and keep redefining it. In the beginning, Tyler's "why" was putting a roof over his kids' heads. Once that was handled, it became building a real business. Now, it's changing an entire industry. Last year, over $80 billion was spent on commercial truck repair in North America – bigger than the music and cruise industries combined. The industry is fragmented and chaotic, with over 80,000 open diesel tech jobs. Tyler's solution: make existing techs more efficient through better tools and training.
Hire for intangibles, not resumes. Tyler has people running multimillion-dollar divisions who wouldn't get past HR with their original resumes. His retail sales manager (responsible for $60-70 million in revenue) was his executive assistant five years ago. His data division manager was an assistant kindergarten teacher who knew nothing about trucks.
His favorite interview question: "Where do you see yourself in five years?" Most people give the HR answer. But once in a while, someone shares their real vision, and not what they think the hiring manager wants to hear – even if that means not being with his company in 5 years. Those are the people Tyler hires.
The Hard Parts Nobody Talks About
Tyler didn't take a salary for the first year and a half. When he finally did, he was the lowest-paid employee in the company. He bootstrapped everything, and cash was a challenge as the company grew. For years, he didn't take a distribution that wasn't for taxes.
His philosophy: he's never seen a company go bankrupt that didn't have debt. So he avoided it.
Key Takeaways
Courage is what holds most people back. Tyler didn't want to quit his job – he was convinced to do it by confronting the fear and realizing the downside wasn't that bad. Everything he hasn't done in life has been from a lack of courage.
Give up control or cap your growth. The reason most businesses plateau is the owner. You can't do it all. You have to trust people and let the business grow itself.
Riches are in the niches. Tyler's deep, firsthand experience in commercial truck repair gave him an edge nobody else could replicate. That knowledge created a moat around the business.
Goals without plans are wishes. The people who know where they're going and have a blueprint to get there are the ones who will treat your customers right and become leaders in your company.
Photos by The Good Habit Photography.
What is Tech On Tap?
Tech on Tap is our monthly series bringing together Columbia's tech community for expert insights and real connections, every third Thursday from 5-6:30pm at the Boyd Innovation Center. Featured speakers share practical lessons from their founder journeys, followed by networking over drinks and light bites. It's where Columbia's tech founders, professionals, and future entrepreneurs gather to learn, connect, and grow.
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