HELLO THERE!
Cheraine Escott, Founder of Cheraine & Co
I’m turning 50 next year, and instead of settling in, I’m starting again. After almost five decades of carrying inherited beliefs about money, success, security, and what was "realistic", I decided to challenge them and build a portfolio of my own. Today I run Cheraine & Co, a holding company for AI-first digital businesses and I’m documenting the whole thing in public: the experiments, the lessons, the doubt, and the wins.

Cheraine Escott
Hey there!
You're reading Cheraine & Co, a weekly newsletter about starting again and building businesses out loud. Every issue is an honest look at what I'm making, what's working, what isn't, and what it really feels like from the inside. No highlight reel. Let's get into it.
THE INTERVIEW
Getting to know me, and why I’m doing this
Why start over now, at almost 50?
Because I'm not actually starting from zero. I'm starting from experience.
Over my career I've been an executive assistant, a real estate agency owner, a recruiter, a teacher across three countries, a university lecturer, and a startup founder. I've built businesses and closed them, including a startup that connected more than 8,000 professionals with employers across 119 countries.
So when I say I'm starting again, I don't mean naively. For years I still told myself that building something of my own again was for other people. Younger people. People with less to lose. Then I realised that was just a story, and I had a choice. Keep protecting a version of my life I'd outgrown, or find out what I'm actually capable of.
Turning 50 didn't make me feel like time was running out. It made me feel like it was time to begin.
I have made the mistakes. You do not have to.
That's the whole reason I'm sharing my method. I've tried enough things to know what actually works and what doesn't. So that's exactly what you get from me: what worked, what didn't, and the lessons that cost me years, so you can skip them.
Your past does not have to define your future.
What is Cheraine & Co, exactly?
It's my holding company for AI-first digital businesses. Rather than betting everything on one big startup, I'm building a portfolio of focused brands that solve real problems where AI can do most of the hard work. My main business right now is Approached, which helps senior professionals get discovered for opportunities instead of endlessly applying for jobs. Behind it I'm testing other ideas that I can’t wait to share with you soon!
Aren’t you scared? What about the doubt?
Of course. The doubt doesn't disappear because you decide to be brave. Some weeks I feel like I have no idea what I'm doing, or that everyone can see straight through me. I've learned not to wait for the fear to go away before I act. I've stopped treating doubt as a stop sign and started treating it as a sign I'm doing something that matters. I feel it, and I build anyway.
The biggest risk is not failing. It's spending your life wondering, what if I had tried?
Why build in public instead of quietly?
Two reasons. First, accountability. It’s a lot harder to quit something when people are watching. Second, I think the messy middle is the most useful part of any story, and almost nobody shows it. You see the launch and the win, never the wobble in between. I want to document the wobble too, because that's the part that helps someone else believe they can start.
You cannot think your way into a new life. You have to experiment your way there.
TODAY’S WORKSPACE
Live from Kyoto, Japan
Right now I'm writing this from my desk in the tatami room inside my Kyoto apartment. It’s minimalist, not glamorous but it doesn't need to be. Most of what I build happens here, one focused block at a time, with two screens, a messy desk and more browser tabs open than I'd like to admit.
This is what reinvention actually looks like.
But since I just got back from Greece last week, and the office is still a mess, here’s a pic of me in Folegandros instead.

Absolutely love the Greek Islands!
▶ How I usually start the day: Yoga when I wake up and then walking my Bali rescue dog through the parks of Kyoto (this is the 3rd country she’s lived in now!)
▶ Podcast on repeat: Insight Timer Meditations
▶ Current read: The shortest history of Greece - great holiday reading!
▶ Must-have tool: Wispr Flow - I can’t live without it (check out the offer down below)
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Come build with me
▶ Prefer to listen? I read each entry aloud on YouTube (coming soon)
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