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    2023 Annual Review

    By Kieran Drew

    2023 marked my second year as an entrepreneur, and what a rollercoaster it’s been. I:

    • Attracted 100,000 new followers

    • Hit two 6-figure months

    • Grossed over $500,000

    Today, I want to share with you the five key decisions that impacted my business growth the most. Including killing my brand, making an important hire, and what’s next going forward.

    It’s a 7-minute read.

    Let’s dive in.

    Going all in

    I began the year drowning in commitments: Group coaching, 1-1 coaching, consulting, newsletter ads, affiliating, digital product sales, emails, and social media. A circus clown would’ve been proud of my juggling, but I was exhausted and not enjoying my direction.

    Thankfully, I revisited Essentialism during the holidays.

    I didn’t need a book to tell me I was spread too thin, but I did need to be reminded of the costs. You can’t do everything at once. And you can’t make your best contribution when you’re bogged down in non-essential work.

    In February, I announced that I’d go all in on one thing:


    I cancelled most of my clients. I stopped consulting. I turned down ads and affiliates. My income plummeted by 70%, but I wasn’t worried. The decision felt good. My gut was screaming at me to strip away the fluff from my focus and I knew as soon as I did, it was the right choice (for my sanity at the very least!).

    Of course, ‘writing’ in itself is not a goal.

    So I set two targets:

    1) Build a newsletter under the name ‘Digital Freedom’. I loved the name, but unfortunately, the brand didn’t survive the year. I’ve not spoken about that publicly yet, but I’ve explained it in the 4th point of this review.

    2) Achieve a 10% ‘low leveraged’ income. This was a fun target because it forced me to turn down some lucrative but time-intensive opportunities. Unexpectedly, it also worked. We went from 35% to 9% — a great example of ‘what you measure, you improve.’

    Playing the right games

    Marcus Aurelius once said, "The more you say no to the things that don't matter, the more you can say yes to the things that do”.

    I felt like I was rebuilding the business from the ground up. Only this time, I had a different plan: Invest all energy into compounding activities I enjoy.

    I focused on three areas:

    1) Writing. In 2022, writing was squeezed around the business. In 2023, writing is the business. I’ve written 4-6 hours a day, 5-6 days per week. I didn’t feel the progress day-to-day, but I cringe at my content from 6 months ago — a painful but useful indicator of improvement.

    2) Pursuing curiosity. I now read for 2-3 hours per day. Many smarter and better writers swear by reading constantly, and I finally get why this “luxury” is a growth hack. I’ve explored three topics this year: Marketing, copywriting, and human nature. I’ve now read many of the classics and am starting to gain what Naval Ravikant often discusses: Specific knowledge. Ideas and concepts are clicking in exciting ways.

    3) Building products. When I quit coaching, I got many requests for my writing systems. This was a good lesson in scarcity: less availability means more demand. I read Purple Cow during my marketing binge and became fascinated by building products I’d be proud of.

    It took three months to build High Impact Writing.

    Considering my first product launch grossed $5,000, making $140,000 in a month was mind-blowing. It felt like a massive fluke. September’s relaunch then pulled in $180,000. This did not do any favours for my flukey feeling, but I’m eternally grateful for the wins (thank you for the support).

    For Black Friday, I soft-launched my third digital product, the Magnetic Content Masterclass. This is a monthly subscription, and the reception has been great from current buyers. The difference between my group coaching and the masterclass is that the group coaching was limited to 5 people. Instead, the masterclass is like a mini-course every week, so I can deliver it en masse. This feels more aligned with my mission of making an impact at scale.

    I’m relaunching in a few days and will scale it gradually over the year.

    The key takeaway here is the importance of doing less but better. Much of business success is luck, but it’s also judgment, too. You need to pick the right games by leaning into work that feels like play. And constantly prioritise the highest-leverage returns on your energy.

    But I couldn’t have pulled this off without a key investment (if I may call her that).

    What you must invest in

    Despite the income uncertainty at the start of the year, I asked my girlfriend Jena to quit her 9-5 to join the business. I jokingly call her my chief clarity officer because she’s made my life so much easier. We’ve built systems for almost everything, meaning I can spend 95% of my week writing, thinking, and building.

    It also means we’re free to work where we want when we want, which has been a blessing and a massive boost in quality of life (although it can be hard to switch off).

    If you want to grow your business, you need help (sorry, Jena is not for rent). I wish I had hired her earlier. Even if hiring ruins your profit margins, you win back so much time that your earning capacity will skyrocket. You must spend money to make money.

    I also invested heavily in mentorship.

    Before 2023, I thought having a mentor was an overhyped concept from Hormozi and his army of clones. I’m now fully converted, and you can expect more nose-strap pictures from me in 2024.

    Jokes aside, I spent $31,000 on a business mentor in September. He has already paid for himself. The benefit of having an expert to bounce ideas off saves so much mental energy and skyrockets your learning rate. We have nine months left, and I plan to make good use of it with focused execution (2024’s plan is at the end of this review).

    I also invested ~$3,000 in my first writing coach(es). One for email and one for longer form. Again, unbelievably helpful. You don’t realise how much your writing sucks until someone tears it apart.

    Let’s talk about the problem of USPs.

    Killing the brand

    In May, I jokingly emailed that Digital Freedom was the wrong name for my newsletter. Little did I know that it was the crack that would become a canyon.

    The problem?

    I had started cringing when I said it in conversation. I thought it was an excellent name at first, but I don’t feel comfortable selling ‘hopium’ to struggling 9-5ers, nor do I want to build my business by dangling a dream of freedom in front of you like a carrot on a stick.

    Don’t get me wrong, as someone who recently quit his 9-5, I care deeply about helping people escape the rat race and experience entrepreneurial freedom. I’ll continue to share ideas for anyone who wants to do the same.

    But I hate this vibe of people preaching that you can escape your 9-5 whilst relaxing on a beach. I’ve never worked harder to build what I have, and I refuse to pretend otherwise for a quick profit. Writing is hard. Entrepreneurship is hard. But that’s the bloody point. Few people have what it takes to see this thing through, and that’s precisely the group of people I want to write to.

    So, what does this mean for my brand?

    Well, I’ve let Digital Freedom die a slow death. And I’m avoiding any brand USPs going forward. Labels mean limits, and the online world moves so fast that, in my opinion, flexibility is well worth the trade-off in memorability.

    For now, my promise is to help you become a smarter writer, thinker, and entrepreneur because that’s the mission I’m on, too. I will follow Naval Ravikant’s advice and build under my name for maximum accountability. And I want to own the position of ‘guide not guru’ in 2024, so this feels right.

    Let’s wrap up with the plan going forward.

    Building smart

    We started this review by discussing priorities. We’ll finish with the same.

    Last month, I saw Chris Williamson live. He was great but ignited a serious pang of envy. Chris went to the same university as me, and here he was giving live talks (something I’d love to do because it sounds terrifying), yet here I am writing tweets.

    I’ve always wanted a podcast because it sounds like the greatest forcing function to pursue your curiosity and meet smart people. Last year, I thought about starting one. I decided the timing was wrong. Over the last month, I thought about seriously starting one, but I’ve again decided that the timing is wrong.


    Not because I’m waiting for the perfect moment. Hell, that was a year ago. But because you can only do a few things well. Compounding requires focus, and focus requires sacrifice. You can’t win it all at once.

    I have two priorities in 2024. My writing and my business. Both have just started to get good, and the big mistake would be to take the foot off the gas because of a few early results. As Charlie Munger once said, the golden rule of compounding is never unnecessarily interrupting it.

    First, I’ll keep writing and reading as much as possible and have faith that this will help carry my brand and business in an exciting direction.

    Second, I’m fascinated by leverage and consider myself a keen student of systems. 2024, I want to combine everything I’ve learned to turn my business into a well-oiled machine.

    The first goal is to make High Impact Writing the best social media writing product in the world. I’ve taken pretty much all of them, and I know this is a realistic target because few people can teach copywriting, storytelling, and personality-based content blended together as I see it (which is the only way you can succeed in the evolving social media arena).

    This means I’ll upgrade the course content heavily in the next few months.

    Once that’s done, I have several other products to build. I won’t spill the sauce now, but I refuse to charge for anything until I’m confident I can build it better than everyone else. The first product will help you ace a topic close to my heart — it rhymes with Drewsletter, and it will be awesome.

    I have no financial target for 2024 because I believe number goals lead to poor decisions and steal joy from the process. The aim is to have every business procedure streamlined, every system dialled in, and a product library my fans find immensely helpful.

    If, by then, I’m still thinking about a podcast, I’ll be in a great position to take it on. It’s my carrot on a stick. Or maybe I’ll start thinking about something else, like a book.

    I’m not sure what the future holds, but I look forward to sharing everything with you as we go.

    As always, cheers for reading. Best of luck with the year ahead. Let me know if I can help with anything.

    Writing online to grow your business? Two ways I can help:

    1.⁠ ⁠Get a step-by-step blueprint for attracting an engaged audience with High Impact Writing

    2.⁠ ⁠⁠Join a weekly masterclass and get 5 content ideas delivered to your inbox every Thursday
    The black eye was also a parting treat from 2023. Don’t get off the sofa too fast!

    Kieran Drew

    About Kieran

    Ex dentist, current writer, future Onlyfans star · Sharing what I learn about writing well, thinking clearly, and building an online business