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Tamsin Henderson of The Copy Kooks Club: “Hire mentors, coaches and people smarter than you”

Hire mentors, coaches and people smarter than you For a long time, I resisted hiring a coach, convinced I could figure it all out myself. How arrogant! How blinkered! I can honestly say, the day I put some skin in the game and hired my first business coach — a gigantic and deeply scary investment for me at […]

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Hire mentors, coaches and people smarter than you

For a long time, I resisted hiring a coach, convinced I could figure it all out myself. How arrogant! How blinkered! I can honestly say, the day I put some skin in the game and hired my first business coach — a gigantic and deeply scary investment for me at the time — everything changed.

The opportunities, connections, accountability, shortcuts and transformations that came out of talking to someone a few steps ahead of me was astonishing. Nowadays, I don’t think twice about hiring mentors or enrolling in courses. I see it as an investment rather than a cost. One that will pay back dividends for years to come.


As part of our series called “5 Things I Wish Someone Told Me Before I Began Leading My Company”, I had the pleasure of interviewing Tamsin Henderson, a freelance copywriter and creator of a best-selling copywriting course. Over 40,000 students have the copy bug thanks to her fun, down-to-earth digital programs.

She is also the founder of The Copy Kooks Club, where she helps entrepreneurial word nerds give their businesses the best possible chance of success.

When not evangelizing about the life-changing magic of words, she can be found cozying up with her daughter and mini schnauzer at home in Cambridge, England.


Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

Well, like most copywriters I fell into this world.

It all kicked off in 2013, while I was working as a PR consultant. I’d written a press release about this crazy Swarovski-crystal covered piano commissioned by a wealthy Sheikh.

When not a single media outlet showed interest in the story, I panicked and hit up Google in search of help.

That was where I stumbled across the Four U’s. Essentially, it’s a copywriting checklist to run your headlines and subject lines through, to increase your chances of them getting read and opened.

(If you’re curious, the four U’s are: Unique, Urgent, Ultra-specific and Useful.)

I rewrote my headline to make it ultra-specific, then repitched the media with the exact same story. Within a few days, over 70 websites and newspapers had covered it, reaching millions of eyeballs, worldwide. I was stunned, my client was thrilled, and I immediately became hooked on copywriting.

Pretty soon people started asking me to write for them. I began helping businesses attract customers through their words… and after a few years, I became a teacher too. Curious about online education and on maternity leave, I tried my hand at a copywriting course.

That course ended up becoming a best seller with over 42,000 students in 171 countries. Still blows me away! And soon after that, I created Copy Kooks, a copywriting school for entrepreneurial word nerds.

What was the “Aha Moment” that led to the idea for your current company? Can you share that story with us?

The reviews from my students often mentioned how the short, simple lessons encouraged them to stay motivated.

And I realized that not everybody wants to be the next Ben Settle or an A-list direct response copywriter. Many people just want to build simple businesses they can control from their laptops. Freelancing, remote work, flexible side-hustles, that sort of thing.

It became clear there was a need for fun, non-intimidating copywriting courses to help busy, easily distracted people get more of their ideas seen, heard and acted on. And so, Copy Kooks was born. A series of short, snappy, business building courses for freelance writers and entrepreneurs.

Can you tell us a story about the hard times that you faced when you first started your journey? Did you ever consider giving up? Where did you get the drive to continue even though things were so hard?

I struggled with visibility at first. Like a lot of introverts, the showing up side of online business can be a tough nut to crack. I remember rewriting and deleting a Facebook post over and over again. Staring down the lens of a video camera like a lost rabbit. And regularly throwing my hands into the air, thinking, “I’m not cut out for this!”

But with every incremental win — a gingerly produced Facebook live, a particularly personal email — I grew stronger and more resilient. I found that the more I gave, the more I got back. And even though I still struggle with shyness sometimes, I know that by sharing this, I’m helping other people see what’s possible. This is what drives me to keep going when things get sticky.

So, how are things going today? How did your grit and resilience lead to your eventual success?

I’m so glad I didn’t let my inner critic stop me in my tracks. Today, there are over 10,000 people in The Copy Kooks Club and my original course is a number one on Udemy.

I frequently get emails from people telling me my courses have helped them move past a block, or given them the strength to break out of their comfort zone.

The woman in tears because she could finally afford a plane ticket home. The guy who smashed imposter syndrome and landed a 12,000 dollars job. The single mum who’s business, once flapping in the wind, is now thriving.

These stories are my grit and resilience.

What do you think makes your company stand out? Can you share a story?

I’ve got a T-shirted printed with the words ‘Typo Tam’. It’s a badge I wear with honor as a self-proclaimed imperfectionist, because I believe that a) done is better than perfect when you’re building a business and b) we should all be hiring proofreaders anyway!

I see a lot of people never getting their businesses off the ground because they’re stuck in the mindset of being perfect. Of having everything figured out. And I see a lot of pain because of it. I want to show people that it’s okay to make mistakes. In fact, it’s an important part of the journey.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘takeaways’ you learned from that?

I’m not sure it’s particularly funny, but the tech issues I had around producing a digital course were laughable. From endlessly trying to fix sound quality to editing the videos, I spent way too much time troubleshooting software and hardware issues.

After a few more years in business and continued tech challenges, I’ve come to realize the common denominator here. Me. I am just not great with tech. I don’t have the patience for reading instructions. I plough into things and try to figure them out as I go — often with disastrous consequences. I think I’m becoming known for it and that’s embarrassing!

Often leaders are asked to share the best advice they received. But let’s reverse the question. Can you share a story about advice you’ve received that you now wish you never followed?

Truly, I don’t think I’ve ever had any dud advice! I’ve been really lucky to work with some amazing, kind, smart people across my career. I can honestly say I’ve learnt something from every single one of them. Even if it wasn’t obvious at first.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

  1. Empathy

When I created Copy Kooks, I had this fixed plan to serve only online business owners. I’d done my research and that was what I wanted to do… end of. But I wasn’t listening to what people were saying. People kept asking for advice on setting up freelance businesses. Or how to get copywriting clients. How to write cold emails, that sort of thing.

I resisted for far too long, before realizing that instead of trying to mold my business around me, I needed to address the problems my students were having. As soon as I focused on that everything clicked into place and my business became truly viable.

2. Long term thinking

It took me an entire year to build a 3-hour course. All the content, editing, lighting, sound mastery, slide design, video tech — there was so much to learn and think about and progress was slow.

There were a million times I wanted to give up. Many a night, I would want to crash on the sofa and make it through at least half an episode of Breaking Bad. But I knew that if I put in the work now, it would pay off in the end. And it did.

A lot of people want overnight success and give up at the first hurdle. But almost everything meaningful takes time. So if you can cultivate a long-term approach and respect the process, the rewards often far outweigh the discomfort at the time.

3. Imperfection

Confession time. I am never happy with anything I write, make, do or create. Far from it, in fact. But if I waited until that mythical moment to arrive — the moment where everything feels perfect (hint: it never does) — I’d be washed up and stony-broke with no business to speak of!

I’ve learnt that pushing forward, pressing publish, and accepting yourself warts ’n’ all is what makes you stronger. Yes, you will feel uncomfortable and vulnerable at first. But pursuing perfection is a mirage, a pitfall and ultimately will hold you back.

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

Running a business and looking after yourself can be tricky. I would often ignore warning signs from my body. Disrupted sleep, swirling thoughts, anxiety, and forgetfulness. We all know the signs to watch for, but how often do we truly listen?

I’ve learnt an awful lot about the effects of cortisol on the body in the last few years and for me, making an extra buck is not worth damaging my physical and mental health. So these days I make a conscious effort to make self-care as easy as possible. And I don’t shy away from paying for help to buy time back.

What are the most common mistakes you have seen CEOs & founders make when they start a business? What can be done to avoid those errors?

Trying to get everything perfect upfront. Stuck in procrasta-research and never moving forward. Get your ideas out and tested as soon as possible, then tweak and iterate them. Want to build your own online course? Pre-sell it. Yes, it’s scary, but nothing is more motivating or useful than seeing your ideas out there in the wild.

In your experience, which aspect of running a company tends to be most underestimated? Can you explain or give an example?

All the moving parts and how hard it is to delegate when you’re always busy. Hire help before you’re ready. Put systems in place to pre-empt those moments of chaotic panic and keep you on an even keel.

There was one particular course launch, where I left hiring the right help until it was too late. So when things started to go wrong, it was down to me fix them while also trying to run the launch. All the time, resources and energy I’d put into building up to that launch pretty much went up in a cloud of smoke. So hire before you’re ready!

Addendum: When you find people you know, like and trust, hold on to them like gold dust.

Ok super. Here is the main question of our interview. What are your “5 Things I Wish Someone Told Me Before I Began Leading My Company”? Please share a story or an example for each.

  1. 90% of business problems are personal problems in disguise.

Michael Port’s awesome quote really hammers home that business is personal. I’ve found creating a business to be the biggest form of self-development there is. It bubbles to the surface all of your foibles, shortcomings and anxieties, and shines a piercing spotlight on them.

That’s both an uncomfortable and a good thing… as long as you take time to work through them. For me, those were things like setting boundaries, fear of criticism and being willing to ask for help.

2. Pause to celebrate wins

The hamster wheel of entrepreneurship means we rarely stop to celebrate our achievements. Instead, we soldier on, looking for the next goal and the next milestone, heading closer and closer towards burn out.

When I started to observe this in myself, I wondered what it was I was really reaching for. Was it the big revenue goal? Was it more zeros on my email list? Or was this just a state of entrepreneurial delirium that I couldn’t slap myself awake from?

Pausing to focus on your achievements forces you into gratitude mode. This halts the merry-go-round of constant ‘doing’ and gives you the feeling of satisfaction we need to anchor ourselves in, before skidding off to the next big idea.

3. Hire mentors, coaches and people smarter than you

For a long time, I resisted hiring a coach, convinced I could figure it all out myself. How arrogant! How blinkered! I can honestly say, the day I put some skin in the game and hired my first business coach — a gigantic and deeply scary investment for me at the time — everything changed.

The opportunities, connections, accountability, shortcuts and transformations that came out of talking to someone a few steps ahead of me was astonishing. Nowadays, I don’t think twice about hiring mentors or enrolling in courses. I see it as an investment rather than a cost. One that will pay back dividends for years to come.

4. Practice relentless self-trust

There are a million ways to get from A to B in business. And what works for some may not work for you, and vice versa. I believe in trusting your gut wholeheartedly and only doing things that feel like a “HELL YEAH!” or “no.” (Nod to my favorite entrepreneur, Derek Sivers, there).

Looking back I can tie every win or mistake to a sensation in my soul that I either followed or ignored. In time that compass has sharpened though, and I’ve learnt to let it guide me relentlessly.

5. Don’t take yourself too seriously

The more I dropped the cloak of ‘professionalism’ and acting how I thought I was supposed to, the more fun I had. And the more fun I had, the more my content resonated with others and the more my business thrived.

Self-consciousness freezes you. It locks you in its grip and stops you from growing. I do not know the secret shortcut to this! Only to say that the more often you do the thing that scares you, the more you realize nobody’s going to throw rotten tomatoes at you — and that’s freeing.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

I believe everybody should learn the art and science of copywriting! Of course, I’m biased, but I’ve also seen how dramatically your odds can change when you can write clearly and persuasively.

Because if you can get more of your ideas seen, heard, understood and acted on, you’re going to enjoy more success, be it in life or business.

And since we all communicate online these days, that pretty much all comes down to the written word. So yeah, I’m kind of evangelical about the power of learning how to write with clarity and punch. It can make all the difference to your career and business.

How can our readers further follow you online?

www.copykooks.com

https://www.facebook.com/groups/CopyKooksClub
https://www.linkedin.com/in/tamhenderson/

This was very inspiring. Thank you so much for the time you spent with this!

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