Lessons from a Conversation with a Billionaire


Hey friends,

A couple of days ago, I had a lovely conversation with Andrew Wilkinson on my Deep Dive podcast. He’s about to publish his first book – Never Enough: From Barista to Billionaire. I read it this week – it’s awesome, super engaging, with lots of food for thought.

I’ve been following Andrew on Twitter for like 10+ years – I was an enthusiast and small-fish-entrepreneur in the worlds of web design and web development back in the day (circa 2010-2018), and Andrew was niche-famous in that world for running MetaLab, a high end design agency that designed apps like Slack and Facebook Messenger. I (and the rest of the design community, and later a lot of internet entrepreneur type people) followed Andrew’s journey as he started a holding company called Tiny and began to buy businesses like DribbbleAeropress and others. Now he’s officially a billionaire with 40+ businesses in his portfolio. Absolutely bananas.

In this email, I wanted to share what my biggest lesson from the conversation was.

But first, it’s worth emphasising just how nuts being a billionaire is. It’s just a single letter that separates it from millionaire, which can lead people (including me) to think “oh it’s like a millionaire but a bit richer”. Here’s how I visualise just how much richer it really is: Imagine earning so much that you could save or invest $1m every year… that would be pretty cool, right? Now imagine earning so much that you could save or invest $25 million every year… now imagine doing that for 40 years, every year, from age 25 to age 65. If you saved $25m for 40 years, you’d end up with $1 billion.

Andrew Wilkinson’s a billionaire, and he’s 36. (Yes I know that a lot of that is paper net worth based on company valuations etc etc, which fluctuates etc etc, but it’s still pretty bloody bananas).

So with that out of the way – the biggest lesson I took away from the conversation was the idea of anti-goals – that it’s all well and good setting goals (career, financial, health, relationships, anything) and working towards them. But it’s worth figuring out what your anti-goals are. Ie: What are the things you definitely want to avoid in pursuit of your goals?

Andrew told me a bunch of stories (and his book has a bunch more) of ridiculously rich people he’s met who are pretty stressed and miserable. The pursuit of wealth (and fame, status, success etc) has the tendency to torpedo your health and relationships, and bind you in a prison of your own making. Obviously, no one’s crying tears for billionaires and celebrities, but from hearing stories about them (from Andrew, and from other people I know who know those sorts of people), a lot of them lead pretty unenviable lives. You certainly wouldn’t want to swap places with a lot of them.

I asked Andrew what seems to separate the people who are rich and happy, from the people who are rich and unhappy. And from what he gathers (and from his own personal experience), a lot of it comes down to Anti-Goals: The people who are rich and also happy know what they want, but crucially also what they don’t want. And they avoid what they don’t want, even if it comes at the cost of more of the thing they do want.

This vibes with something I’ve heard from James Clear (mega bestselling author of Atomic Habits) too: that the happiest (successful) writers seem to be the ones who define what they want their life to look like, and optimise their work within the constraints of their life.

Charlie Munger (apparently) had a nice quote to this effect: “All I want to know is where I’m going to die so I’ll never go there”.

It’s pretty hard for us to know exactly what it would take for us to be happy, but it’s pretty easy for us to work out what it would take for us to be very unhappy.

In my case, if I imagine what a miserable working week would be (within the context of my existing business), it would be Zoom calls all day, no creative work, strict deadlines from sponsors, and the feeling that I’m making videos that I don’t actually think are useful just for the sake of an algorithm or a sponsor. I’m also staying in the house all day, not doing any exercise, eating unhealthy takeaway food, and not seeing any friends.

Okay great, I’ve just defined what my nightmare work week would look like. So now I can just make sure to avoid having work days that look like that. Easy enough.

Similarly, when I’m in pursuit of any of my goals (especially the work-themed one of growing our business to $10m in annual revenue), it’s very useful to define the anti-goals along the way. In my case, sure, I’m playing the entrepreneurship game and trying to grow the business. But with the following constraints:

  1. That I should never feel like I “have” to do something I don’t want to do
  2. That growing the business never comes at the expense of my personal integrity or authenticity
  3. That growing the business never comes at the expense of doing the right thing for our students and customers
  4. That growing the business never leads to me feeling like I have to sacrifice my health or relationships to get to an arbitrary revenue milestone
  5. … And a few others

These constraints are likely to hamper our business growth. You can always grow the numbers by being a little scammy with your customers (in the short-term anyway), and by sacrificing other aspects of your life for the sake of the hustle (again, in the short term). But those are almost never the right moves when it comes to the long-term, infinite game of continuing to be able to play the game, while enjoying the journey along the way.

But even outside of the more obvious integrity-themed areas, there are plenty of ways in which we could grow the business… I just don’t want to do any of them if they’d require me to do things I fundamentally don’t want to do. For example, there’s a lot of money we could make if I just did a load of corporate talks all the time. Or if I churned out a bunch more sponsored YouTube videos each month. Or if we focused on helping big companies build a presence on YouTube. Those would all be avenues to get the business to $10m in revenue… but none of them are things I want to do.

In fact, one of my core philosophies in trying to build a Feel-Good Business is that my day-to-day calendar looks as close as possible to the calendar I’d have if I wasn’t actually trying to grow the business. This means having large blocks of time for deep creative work, for reading and writing and thinking. It means taking long lunch breaks, and not being too “optimised” with the videos I’m making, podcasts I’m recording or the emails I’m writing (hence why this email is already 1,200 words lol). It could definitely be shorter, but if I wasn’t trying to grow the business, I’d want to have a weekly email where I just wrote from the heart and wrote whatever came to mind without thinking about it too hard. If people want to read it, great. If they don’t, they’re very welcome to unsubscribe 🙂

The conversation with Andrew helped reinforce to me the importance of going after what genuinely sparks joy and fulfilment, rather than chasing success metrics: the journey rather than the destination.

So let’s wrap up with a question: As you pursue success in your own work, what are some anti-goals you’d like to commit to avoiding? I’d love if you could hit reply and let me know what you decide 🙂

Have a great week!

Ali xx

♥️ My Favourite Things

  1. Book – I absolutely loved Ryan Deiss’ book Get Scaleable: The Operating System Your Business Needs To Run and Scale Without You. I discovered Ryan on my friend Billy Broas’ YouTube channel via this interview – Billy’s channel incidentally has like 22 subscribers as I write this, and the interview has like 120 views, so it really felt like I was discovering a new corner of the internet. I later discovered that Ryan’s plenty famous in the world of entrepreneurs, I’d just never really come across his stuff. But now I’m a fan after this interview + reading the book.
  2. Book – This week, I also finished reading A New Earth by Eckhart Tolle. It’s the latest in my exploration of the world of spirituality. I actually much preferred it to The Power of Now which is Tolle’s more famous book – I thought A New Earth was structured in a way that made a lot more sense to me. If you’re into the whole spirituality enlightenment stuff, you might like it 🙂 Although tbh if you’re in that world, you’ve probably read it long before I have 🤣
  3. Video – I continue to enjoy and relate to Vanessa Lau’s explorations into the world of being a YouTuber on her own terms. Her recent video about why she cancelled $200k worth of sponsorships resonated a lot with my own experiences: it’s always nice to see fellow creators choosing to prioritise their mental, emotional and physical health over the demands of audiences and algorithms 😃 Helps reinforce the path I try to stick to as well which is broadly similar.
  4. Podcast – I also really enjoyed Shaan Puri’s interview with Tim Ferriss on My First Million. As you guys know, Tim’s been a major inspiration in my own life and career. We’ve never met (although I’m sure it’ll happen some time), but I always listen whenever he’s interviewed on podcasts as in many ways, I (and many, many others) are following the path that Tim introduced us to in The Four-Hour Work Week. Hearing how he’s grappling with life, success, money, happiness and mental health is hugely interesting and inspiring. GG Shaan for an awesome interview.

🎬 My New Videos

🤑My honest advice to someone who wants financial freedom – The other day I had a conversation with someone about their financial goals. It sparked the idea for this video, where I share my honest advice to anyone who wants to hit financial freedom. I hope you get some value out of it!

✍️ Quote of the Week

“I think a lot of people, myself included, can sometimes get stuck. Like ‘They haven’t called me, so I’m not going to call them.’ If you want to talk to your friend just call them. You don’t have to play chicken about who’s going to take the first step.”

From How Friends Become Closer by Julie Beck. Resurfaced using Readwise.

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Mike J
Mike J
18 days ago

Great article! I really enjoyed the advice, and I will take time today to figure out what my anti-goals will be. Thank you for taking the time to write this.