In 2016, I walked away from a comfortable corporate career to build a startup in hospitality technology.
I was fifty years old. I had a mortgage, a wife, and all the obligations that come with a stable life. I was not the typical hoodie-wearing founder in their twenties. I was a senior executive with something real to lose.
What I didn't have was a single lightning-bolt moment of inspiration.
Instead, I had something more dangerous. A slow, growing certainty that the industry I worked in was broken.
The Problem I Couldn't Ignore
For most of my career, I worked in event and hospitality technology. I sold event management systems to planners and watched hotels struggle to manage group bookings with spreadsheets, emails, and phone calls.
Event organizers were paying for expensive software. Hotels were hosting those events but had no tools of their own. They had almost no visibility into attendees until they arrived. Upselling was manual. Reporting was painful. Room blocks leaked revenue through bad processes.
It felt backwards.
Hotels are experts at selling rooms, but terrible at managing groups.
The idea started simply. What if hotels provided their own event and group management system to planners for free? What if that system gave hotels data, control, and a way to sell more than just bedrooms?
The more I thought about it, the more obvious it seemed. This was a structural problem, not a feature gap.
Why Steven and Me
I didn't start alone.
I had known Steven Hopkinson since 2001, when we worked together at Photolibrary before we exited to Getty Images. He was my manager, he trusted me, and later sent me to Singapore to rescue a failing regional business. We built something real together back then.
Years later, after Getty, The Active Network, and then Lanyon, I was ready to leave corporate life. Over coffee with Steven, I explained what I was seeing in hotels and events.
He had deep hospitality relationships. I had product and sales experience. We both had leadership scars and entrepreneurial itch.
It felt right. Dangerous, but right.
The Fear Nobody Talks About
Leaving a senior job in your fifties hits differently.
This was not "ramen and sleeping on a couch" risk. This was "what happens to my house if this fails" type of risk. "What happens to my marriage" risk. "What happens to my reputation" risk.
Leaving a senior job in your fifties hits differently. This was not ramen-and-a-couch risk. This was house-and-marriage risk.
I remember lying awake asking myself: Am I good enough for this? Why would anyone buy from me? What if I fail publicly?
The only reason I went through with it was my wife Adeline. She was all in from day one. She gave me the confidence and safety to risk a lifetime of gains for the risk of a startup. Without that, I would have stayed where it was safe.
Fear never left. I just learned to work with it.
Our First Yes
We built an ambitious first product. Too ambitious.
Our MVP was a full event management system for hotels. Registration, payments, websites, agendas, speakers, exhibitors, mobile apps. It was more than an MVP. It was a full product pretending to be a prototype.
Our first pilot hotel was Novotel Clarke Quay in Singapore. The general manager, Marcus Hanna, did not need convincing. He volunteered.
That mattered so much more than he probably knows. He gave us time, trust, and access to his team. We showed up to meetings with something half-built and a lot of hope.
Looking back, that first yes was everything. Without it, there is no company.
The Mistake That Almost Killed Us
We overbuilt.
We spent too much time and too much money trying to make something perfect. We believed more features meant more value.
We were wrong.
We built a product we loved. The market did not.
Hotels did not know how to sell an event management system. Planners did not know why they should use it. Nobody wanted to pay.
That was our first near-death moment. Not dramatic collapse, but quiet realization. The product we loved was not the product the market wanted.
Money ran low. Development took longer than planned. Capital disappeared faster than confidence.
Then something important happened. We started listening instead of defending.
The Pivot That Saved Us
In those conversations with hotels, one pain point kept coming up. Room blocks. Group reservations. Housing management.
These processes were deeply broken. Manual, error-prone, and expensive. Hotels lost revenue. Planners lost control. Guests got confused.
We scrapped our original idea and rebuilt around this.
Scrapping our original idea hurt. But listening to customers saved the company.
That pivot hurt. Emotionally and financially. We walked away from something we had spent years creating.
But it was the right call. The new product had a clear buyer, a clear problem, and a clear price.
Learning to Build a Team
We found our CTO, Daniel Low, after reading about his company online. He left his own startup to join ours. That decision still amazes me.
We first tried outsourcing engineering in Vietnam. It did not work. Communication was hard. Quality was inconsistent.
So we changed strategy. We hired engineers directly. Slowly, painfully, one by one, we built our own team in Vietnam under Daniel's leadership.
That team became the backbone of everything that followed.
Momentum
Growth came through relationships and referrals.
Steven's connections opened doors. Accor introduced us to hotels. Conferences created leads. When staff moved hotels, they asked for our system again.
Customer by customer, we reached forty hotels.
We were no longer an idea. We were a product.
The Accor Bet
In 2016, Accor signed a Memorandum of Understanding with us.
It was a startup gamble. We agreed to build with them for twelve months without revenue. They gave us feedback, testing, and credibility. We gave them free licenses.
That deal shaped our product. It forced us to think like an enterprise company.
Three years later, in 2019, that relationship became a commercial Letter of Intent across multiple countries. We went from a pilot to a global rollout conversation.
That moment changed how the market saw us.
Recognition
In 2019, we won WiT Startup of the Year.
Awards do not build companies. But credibility does.
Customers felt proud to use us. Staff felt proud to work for us. Investors paid attention. And Groups360 noticed us.
The Exit That Was Not Simple
Groups360 first approached us about a partnership. In December 2019, that conversation turned into an acquisition, and we signed a Letter of Intent in early 2020.
We were excited. Our technologies were genuinely complementary. Together, we could create an end-to-end solution for group bookings on a global scale.
Then COVID arrived.
Group travel collapsed almost overnight. Hotels shut down. The industry we both served came to a standstill.
Naturally, we worried. Any founder in our position would have. Deals get reconsidered when the world changes that fast.
But what stayed constant was Groups360’s belief in the product. Their message to us was clear. The timing was uncertain, but the strategy was not. They still needed our technology to complete their stack.
Those months were tense. We waited, we wondered, and we kept building.
When they came back and confirmed they were moving forward on the same terms, it felt like a verdict on everything we had built.
That moment still makes me smile.
We won.
The Fight Nobody Sees
Selling the company was not smooth.
Our investors did not want to sell. They wanted to raise more money and grow independently. We wanted to partner with the largest hotel brands in the world.
It became political. Emotional. Personal.
We believed in the combined future enough that we took most of the deal in stock, not cash. We wanted to stay and build, not just exit.
In August 2020, we sold IDEM Hospitality to Groups360.
What Almost Broke Me
Two things surprised me most.
First, legal costs. What should have been a simple deal became months of negotiation and nearly six figures in fees.
Second, how ruthless exits make people. Smiles disappear. Everyone protects their own position. Contracts matter more than trust.
It was exhausting.
It was also worth it.
What I'd Do Differently
I would build less and focus on revenue generation sooner.
I would find five customers before writing code. I would ship something ugly. I would charge earlier.
Features create technical debt. Revenue creates freedom.
I would get better legal advice earlier. Cheap lawyers (or non-existent ones) are expensive later.
The Best Decision We Made
We listened to customers, even when it meant abandoning our original idea.
And we stayed obsessively focused on making something simple enough that nobody needed training.
That is what created referrals. That is what reduced sales friction. That is what built trust.
Why I'm Sharing This
Startup stories are usually written backwards. Success first, struggle edited out.
This one almost broke me.
But it also gave me the most meaningful professional experience of my life.
If you are building something and feel lost, scared, or behind - you are not broken. You are normal.
And if you are sitting on an idea because it feels too risky, I get it. I was fifty when I started. I had everything to lose.
I would still do it again.
Because building something that matters changes you. Even if it nearly destroys you first.
Transparency note: This article was written with the help of an AI language model reflecting how I use modern tools to improve my writing and communication; the story and experiences are mine, and the AI simply helped me tell them more clearly.