From Failing Fast to Breaking Through: A Tech Startup Story with OneUp Sales

Derry Holt, founder and CEO of OneUp Sales, joins us for episode 10 of Tech Startup Stories to share the very real, very human journey of building a startup, from scratch. So often, we only hear about how great the journey has been and it’s easy for CEO’s and Founders to put a positive spin on everything they’ve experience. In this refreshingly candid episode, Derry reflects on the hard lessons, near-death moments, and unexpected wins that have shaped OneUp Sales to the business it is today.

Listen to the Podcast Available on Spotify, Amazon Music, Apple Podcasts, and YouTube.

From Online Gaming to Sales Gamification

The Early Days Before launching OneUp Sales, Derry studied computer game programming at university and later worked in the gaming industry as a developer. But his transition into sales tech came from an unexpected mix of influences, including his co-founder James' experience in door-to-door sales. They decided to merge their skills to create something unique: a gamified way to motivate and manage sales teams.

Like many first-time founders, they dived into the deep end with a bold idea, limited experience, and lots of enthusiasm. In Derry’s words, those early days were “classically very, very scrappy.” They made all the usual mistakes, building a product before speaking to customers, hiring friends instead of the right people, and sinking time and money into the wrong areas. By Derry’s own admission, those mistakes probably cost them five years of progress.

Facing the Toughest Moments

OneUp Sales didn’t have the easiest start. There were at least three points when the business nearly folded. From living on minimal income and sleeping on floors, to running out of cash with no clear plan, to losing clients during COVID-19, it was a journey that could have ended many times over.

But thankfully, they didn’t quit and Derry and James stuck it out. Whether it was stubbornness, grit, or just sheer belief in what they were doing, they kept moving forward. Slowly, they built the company back up. A few key partnerships, a focus on recurring revenue, and lots of late nights meant the business began to gain traction. What followed was sustainable growth, a stable team, and a place in the competitive world of recruitment software.

Learning the Hard Way (And Owning It!)

Derry is the first to admit they built the business back to front. Instead of identifying a clear market problem and building a product to solve it, they started with the product and tried to find someone to buy it. They were fortunate that some of their early features resonated, but this was far from a perfect plan.

Their first customer came through a chance encounter at an event, and Derry reaching out to the execs over X (Twitter). It wasn’t smooth sailing either, for six months the client questioned whether the product had any value at all, but they stuck with it, refined their approach, and eventually won that client back years later. That story, like many others Derry shares, captures the rollercoaster of running a startup, full of setbacks, recoveries, and the importance of persistence.

Getting Back to Their Roots

Now with a team and customers in place, Derry admits that focusing too much on "being a proper business" risked them losing sight of why they started OneUp Sales in the first place, to build cool, innovative things. He and James are now carving out time to experiment, to create fast MVPs, and to try bold new ideas through an internal incubator. It's their way of reigniting the creativity that fuelled the startup from day one.

Advice for Startup Founders

Derry’s story is full of honest lessons. Here’s what he’d share with others starting their own tech journey:

• Don’t build before you talk to customers, understand the problem first.

• Don’t hire based on convenience, hire the right people at the right time.

• Perseverance matters, even when the odds are against you, keep going.

• Embrace the chaos, but learn from it, mistakes are part of the process.

• Never forget why you started, innovation needs space, make time for it.

OneUp Sales is proof that resilience, honesty, and learning from failure are more than just buzzwords, they’re survival skills. Now leading a team of 40, Derry’s journey is a testament to the power of reflection and reinvention.

Listen to the Podcast Available on Spotify, Amazon Music, Apple Podcasts, and YouTube.

Learn more about OneUp Sales and get in touch with Derry Holt.