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Trinny Woodall and Susannah Constantine – ‘Trinny & Susannah’ – are one of TV’s most recognisable duos.

The fashion advisors became household names through BBC series What Not to Wear before fronting Trinny & Susannah Undress… on ITV.

Woodall’s beauty brand Trinny London booked £42 million of revenue in the last year. She also has years of newspaper columns and chart-topping books behind her.

For all her success, however, she has also been through one of the hardest experiences for a person – alcoholism – and one of the most difficult for an entrepreneur: closing down a business.

Ready2shop.com was a late 20th Century startup which built a team of dozens of engineers to provide personalised fashion advice. Despite signing up 220,000 women, it ran out of cash.

“We took too long building out the concept and not long enough deciding how we were going to sell,” Woodall tells the Secret Leaders podcast. “People get so caught in the creative weeds, that they just want to make it perfect, perfect, perfect. They don’t take long enough to think of how they’re going to make money.

“How many channels are we going to have? Who’s going to be in those channels? We want to do cooking… just so many goddamn channels. I wanted to offer everything to women from the get-go. 

“Offering too much, too soon took cash. If there hadn’t been a Dotcom Bubble, maybe we could have easily carried on because [later] people were like ‘I don’t care how you’re ever gonna make profit on the customer, get tons of customers’… and that’s what weirdly we were doing really early on. 

“If we started that business at the beginning of Casper Mattress blitzkrieg, we would have got a second and third round because we would have had so much data and traction and customers.

“But you can’t put everything down to the wrong timing. If everyone puts it down to ‘it was the Dotcom Bubble, there are brands who survived that period, and we didn’t.

“What I’ve learned at Trinny London is to start with one: let’s get that woman to feel comfortable and understand what we’re doing and want to do for her.”

Emotional ending

With the soon-to-be-famous duo unable to raise further funding and Susannah taking time off to have a baby, the job of closing down the business fell to Woodall. She describes the period as “a bit of a blur”.

“I was negotiating with our investors… closing down is the hardest thing to do with a business. I wanted to give everyone a three-month bonus – but if I had there would literally have been no money left for anything.

“There were a lot of people who had worked so hard and I just felt it was horrible to be suddenly without a job. 80% of them were women… there was lots of emotion in the room, and lots of sadness. 

“It’s terribly sad when everyone buys into a vision and they’re on the journey and they’re so committed… and then it doesn’t work out.”

Woodall’s story is told in more detail on the Secret Leaders podcast, hosted by serial entrepreneur Dan Murray-Serter, which is launching a mini-series focused on failures rather than triumphs.

Address the Big L this Mental Health Awareness Week

Alcohol recovery

She says her previous experience in alcohol recovery actually helped her to cope. “I was lucky that I had slight knowledge of meditation because I’d had lots of impostor syndrome in my early 20s – lots of lacking in self worth – and going into recovery taught me to fit in my skin,” she explains. 

“Over the last few years that journey has gotten better and better for me, but when this business closed, I was devastated. I was so sad. It’s like losing something incredibly precious to you. 

“It’s all to do with the voices inside your head, and nothing to do with the exterior. You’ve got to separate out circumstance, business decision, your thoughts. A lot of that has to be processed. 

“I went to a retreat in America called Cottonwood and just made peace with myself. I went for a walk in the desert with the cacti and had a little spiritual awakening moment where I let go of what had happened. 

“I said: ‘I’m open to whatever else is coming in my life. And I’m not trying to paint the picture of coming up with another idea, just keep going like a bloody locomotive train…. I need to stop at the station, get out and take a breath’. 

“I’d forgiven myself a little bit for this failure, because we are our harshest critic.”

Weeks later the BBC called and the pair’s runaway success began.

“Advice I always give to younger entrepreneurs is: stay in your own lane. Because if you look too much at the competition, you dilute the uniqueness of your offering,” Woodall says.

Secret Leaders is available on Apple, Spotify and all major podcast platforms.

What it’s like to make a fortune and lose it – twice