Rewind to the millennium. You were 32, with a four-year-old and another child on the way, and you picked that moment to leave Late Show With David Letterman, where you’d spent five very successful years, to do something that had never been done before. That seems a risky, if not downright reckless, move. What convinced you it was time to go it alone?

I’d always wanted to be an entrepreneur and I believed absolutely that if I harnessed the knowledge and experience and relationships I’d gained at Letterman, created a powerhouse team and offered that expertise to other media outlets it was going to work. And so did Letterman. They immediately said: ‘We’ll be your first client’.

How has the industry changed since you started out in 2000?

Media is constantly evolving. Two decades ago CTB booked six magazines including Oprah and Jane. We don’t book any now because there are hardly any left. Late night will always remain my true love but I recognised the business was changing. There were more late night shows, an increasing number of daytime shows, morning television was expanding and outlets like YouTube, Twitter, Netflix were appearing.

When you live and breathe media, as I have for 30 years, you can feel when the shifts occur and predict which direction the industry’s moving in – and where those all-important advertising dollars are headed. That’s how we were ahead of the curve when streaming and podcasts became a thing. But it’s not just the formats that have changed, it’s the way projects are publicised too. Companies like Apple and Amazon have a guaranteed audience and their focus is about winning awards and accolades so that’s become something we concentrate on too.

You clearly have quite a work ethic?

I do. I am completely focused on results. I’m extremely direct. I never take no for an answer. I admit to being a borderline workaholic but I learnt to delegate because I don’t have a choice. I have enormously strong willpower when it comes to hard work and I know that my clients recognise and appreciate that because they’re the same. David Letterman, Oprah Winfrey, Jimmy Kimmel -- these people don’t just happen. The work they put in is off the scale. Celebrities are on the move all the time. It never stops. The higher their profile, the faster it gets.

Showbusiness is called that for a reason but any industry insider knows all too well that however glamorous the Oscars are, everyone’s feet are hurting on that red carpet. It’s the same day-to-day, working behind the scenes to pull something special out the hat. This is the craziest thing which I seldom told anyone: back when I was a single mum, trying to grow my new business while supporting three kids, I would wait until they went to sleep and then I would put on a neck brace because I was too tired to hold my head up, and continue to work. The washing machine would be running in the background while I’d be doing my emails and then I’d watch a TED Talk every night to fill up my tank because I still craved stimulation and knowledge. And then usually I’d be woken up in the night whether it was a teenager coming home in the small hours or a toddler waking early to play. Glamorous it wasn’t. But there’s always a little magic with the madness.

So it’s 90% madness and 10% magic? Is that what motivates you?

Something people tend not to realize about success is that the pressure only ever increases because once you’ve built your castle you want it to stand strong and not fall. The pressure is delivering more and more, staying creative, staying focused. Fortunately I thrive on it. My mission is always to give every client the best, to elevate them. Creatively speaking, that’s the drug for me.

But I’m also a CEO and what people might miss about my motivation is that I’m an employer with a loyalty and sense of responsibility to the people I have working for me. We are very much a team and I’m extremely proud, not to mention relieved, that CTB managed to retain the entire staff throughout the pandemic.

It sounds like CTB is a great place to be employed. What is its appeal for clients?

Our impressive client list helps. At the start when David Letterman wanted to continue to work with me as an independent company it was a big calling card. It meant I was current. That’s continued over the years. We’ve always had clients with the cool factor whether it was Jon Favreau’s IFC TV show Dinner For Five back in 2001 or the 20th anniversary of Jimmy Kimmel Live in 2023. Our entire podcast division gives us cachet because people see that the key players in that business are with CTB.

The reason people continue to work with us is because of our track record. They trust our brand. Back in the day the media had this arrogant attitude of “We are in charge. We are the ones who dictate what your image will be, how your project will be promoted”. At CTB we’re not about any outlet being more important than any celebrity. We’re always working to finding ways to collaborate creatively -- because everybody wants to narrate their own story – and ensuring that everyone has a positive experience.

I’m proud of the fact that people have confidence that if we’re booking something we’re not just going to treat the client with respect, we’re also going to treat the talent with courtesy and consideration. We’re not about those ‘gotcha!’ moments. It’s our job to deliver somebody who is entertaining, who has the right tone and sensibility for that individual host, and for that to happen the talent has to feel comfortable and secure in order to be their best self in the interview environment.

We’re also known for going the extra mile. Maybe I’m a closet people-pleaser but I’m someone who likes to say “yes” and make things work if I can. And one thing I hope I make work is treading the line between being as tough as necessary, but also flexible. My loyalty is to doing the right thing and that’s how I want our clients to be perceived too.

Many people underestimate the power of the bigger picture strategy, but it’s always been my gameplan because I’m in the business of elevation -- helping people get where they want to go. I want to help every client achieve the success they dream of reaching and it’s always a joint enterprise. The bigger picture means thinking ahead, not just to plan a strategy but to avoid pitfalls and obstacles. We’re experienced and we are seasoned as a company, not just as individuals. That frees the client so they can concentrate on showcasing their content well.

Who have been your inspirations?

Certainly women such as Oprah and Gayle King, Anna Wintour, Katharine Graham of the Washington Post, Liz Tilberis. Women who were strong but who also -- and I didn’t necessarily fully understand this when I started at 32 -- not only knew what they were doing, but treated people with dignity and grace, who were generous.

CTB booked Huffington Post and I remember having breakfast with Arianna Huffington before she sold her company and loving her honesty and her directness. Not acting like everything’s easy, admitting that you have to work round the clock and fight for it.

I was influenced by women outside the industry too. I admired the work ethic of my pediatrician Dr Barbara Landreth who I’d run to for help when I was trying to do my job while being a single mum raising three kids. And by other women I saw go through so much abuse and trauma without even having a job and I just wonder how they survived. I’m always grateful for being a woman who always had a career and the ability support my children. Anyone who knows me in the business knows I have always tried to help women less fortunate than me because I know how hard it was for me -- and I had a good job.

At Letterman you were nicknamed Rainman because of your uncanny memory for every night’s rating. More recently you’ve been described as ‘the OG of talent booking’ because you pretty much invented the industry.

Ha ha. That makes me sound like the Anna Wintour of talent booking! I have huge respect for her as an innovator so I’ll take that.

Seriously though, you have to remember that until I started CTB, talent booking had always been done in-house so for me, as an independent operator, there were no rules to follow. I had to make them up as I went along with the producers and publicity teams and I think the ones we came up with have proved sound because many of them still apply across the industry today. Much of what’s accepted as standard in the business stems from leading the way and setting the precedent and naturally that’s my history.

As for my longevity, that’s due to a combination of constantly looking forward while learning from experience. So when people say ‘OMG it’s amazing that you booked that!’ I always remember the story behind how it was booked because it’s never straightforward. Every booking has a story and, when you’ve been doing it almost 30 years, as I have, you have a history of learning – sometimes the hard way -- banked to draw on if something goes wrong. People pay me to play an expert game and I’m pretty well-versed in the tricks of the trade, but I’m constantly devising new ones too. The industry is continually evolving so I am continually innovating.

Who keeps you humble?

I know where my strengths and skills lie and while I’m creative I also know enough to stay in my own lane. It doesn’t mean I always resist trying to contribute my ideas in late night but I’m not a comedy writer as people like to remind me. I’m like: “I know I’m not a comedy writer, but wouldn’t it be funny if…?” And they’re like: “No. It wouldn’t be. That’s such a cheesy idea.” And I’m like: “Oh. Better stick to talent booking”. The same happens with my kids. I’ll play some song I like to them and they just say: “That’s not cool”. And I’m like “Oh” again. I have plenty of people around who keep me humble.

Tell us about your team.

Another thing I notice people underestimating is the importance of teamwork. I’ve employed a varied and diverse staff because different types of people have different strengths. They’re working from Brooklyn to the Valley to Notting Hill which means CTB is like the city that never sleeps, we always have a booker awake! And we all have each others’ backs.

When I’m hiring I’m looking for someone personable, smart and likeable. Someone a little bit nerdy perhaps, but not too much, and who understands that there’s no room for individual egos because our job is a little bit like arranging the top table at a wedding every day of the week and we have enough of those to deal with already.

Bookers need to be able to compartmentalise while simultaneously keeping as many plates spinning as humanly possible because the pressure is always in-fucking-tense, a little like being a trader on the Wall Street floor. And I don’t just mean juggling the practicalities and logistics but also information. You need to keep a running mental tally of who’s filming in which city versus who’s likely to be available. And you need to keep an eye on other relationships in the industry. Obviously contacts count and being on good terms with managers and publicists is part of our job. But this a business. You’re not trying to be everyone’s best friend. Your job is to deliver consistently and professionally.

Lastly, attention to detail is what that gets you to where you are but you are still only as good as your last 20 bookings plus your next 20 bookings. And those next 20 bookings will change 20 times before they make it on air. But you have to know how to pull from different places, to recognise the importance of having a Plan B and then be able to think on your feet when Plan B doesn’t pan out either. If there’s one thing the pandemic proved it’s that.

Written by Ruby Millington