I couldn’t afford nappies for my newborn. Now I have a multi-million tech firm

When he was at his lowest point, Ashley Bailey remembers being awake at 3am, frantically hunting for cheaper nappies and baby formula, unsure how he would make it financially until the end of the month.

Ashley, 40, who was raised in Accrington, Lancashire, said he did not come from a privileged background, but was driven to succeed and worked his way up through sales and tech before entering the high-stakes start-up world.

The tech entrepreneur spent his time building, scaling, and exiting businesses, landing global partnerships and gaining recognition in the US.

He was living in Didsbury, Manchester, when he met his wife, former Irish pop singer Ciara Newell Bailey, on a train.

“She lived in London and I lived in Manchester and we met when we ended up sitting next to each other on a train,” he said. “I was going back home after a meeting in London and she was going to Manchester for a gig. We kept in contact and about 18 months later, we got together.”

After relocating to London with Ciara, Ashley soon found that what was meant to be a fresh start spiralled into financial strain. By the time his first child was born, it looked like he had made it. He had built businesses, worked with global giants like Google and secured backing through Telefonica’s Wayra start-up accelerator.

But he says behind closed doors, it was a different story. “We couldn’t just go out and buy what we needed without thinking twice,” he recalled. “Every single purchase felt like a calculation.

“On paper, it looked like I was doing well as companies were investing and they were great names. But underneath, there are months of legal work, and you’re running out of money. It takes months to get things live and the reality is, you have about 18 months of not getting revenue.

“Business founders are very good at showing the highlights, funding rounds, growth and big wins. What they don’t talk about is the stress, the debt and the moments when things start slipping.”

For Ashley, things came to a head during Covid when as a small business, he had months of people not seeing him. He says that, as a new father, the pressure was relentless.

“At first, you think it is temporary, then one missed payment leads to another and it creeps up on you. You tell yourself you’ll fix it next month, but it keeps stacking up.

“As a father, you picture being able to provide, not sitting there worrying how to afford the basics.”

Ashley and Ciara bought a house in Richmond, London, during Covid and it was a fixer-upper. “We had just bought this house and every penny counted,” said Ashley. “So I had 18 months of panic and trying to survive.

“We had raised some money just before Covid hit and that money had to last 18 months. We had to carry on paying staff and had a mortgage to pay and it got to the point where I was looking at every single cost including nappies, formula and baby clothes.

“There’s a different kind of weight when you have a child. It’s not just about you anymore. I was up late thinking we couldn’t even afford nappies and I would switch between different websites trying to work out what was the cheapest.”

What began as a desperate solution when he was at rock bottom has since transformed into a multi-million-pound business for Ashley, as he launched a fast-growing tech business called Dig that helps households slash their everyday prices.

The AI-powered platform searches across the entire web to find the lowest prices on exact items, from iPhones and trainers to nappies, buggies and everyday essentials. Ashley says it uncovers significantly lower prices than a standard search, helping families stretch their budgets further at a time when every penny counts.

His business model has attracted key investors, including millionaire businessman Paul Wright, who co-founded Ideal World and Jezz Skelton, founder of jewellery brand Abbott Lyon.

“The cost of living isn’t easing; it’s becoming more predictable,” said Ashley. “With global instability continuing to push prices higher, the need has never been greater.

“As conflicts like the situation with Iran start to impact oil prices and supply chains, it is ordinary families who feel it first.

“Dig came from a real place, that’s why it resonates. It is the thing I wish I’d had at 3am when I was stressed, exhausted and trying to make the last bit of money last.

“I have always been a savvy shopper and like to get the best deal. But at that point in my life, I was living a lifestyle where I needed to try and find the cheapest of everything.”

Dig now has 17,000 users.

Now a father of two, to a five-year-old son and a three-year-old daughter, Ashley says even though his life is now a far cry from the desperate sleepless nights where every pound felt like a battle, he feels it is important to talk about the financial struggles as a business founder, rather than just the successes.

“There’s a lot of pressure to look like you’ve got it all together, especially as a man and when you’ve got a family. Keeping it in just makes it worse.

“It was awful at the time, but it made me a lot stronger. Going through these horrible times shapes you and puts things into perspective and makes you slow down and focus on where you want to be.”