Digital Coffee (Free) #5 — cashing out $700m pre-IPO 🧐 as well as striking while the iron is cold, and approaching interactions with kindness

Happy Sunday! 👋 Thank you to each and every one of you who have opened this email. Also, whilst in the mood of gratitude, thanks to those of you who are providing feedback and helping me shape and evolve the content. 

By way of recap, I want Digital Coffee to be a mix of great commentary to news, trends and analysis — as it’s happening. Couple that with that a dose of smart thinking, advice and challenges — and hopefully you will be able to save time and not make the same mistakes that I have. 

As always — please forward this to anyone you think would benefit from subscribing. Also, I’ve noticed I’ll probably get a bunch more organic signups from Substack.com if everyone clicks the little ❤️ icon at the top of this post. It will take two seconds (if you do enjoy the content) and will help the community grow. 🚀


As for this week’s brief piece of advice — strike while the iron is cold. Don’t quit your job, leave your spouse, or engage in an online feud when emotions are running hot. If you have the urge to strike, sleep on it, hit the gym, take a long walk or binge watch some Netflix. 

Taking feelings, ego and emotion out of behaviour and decisions is not easy. When the mind begins racing, the heart pounding, and the blood pressure skyrocketing, it’s a good idea to take notice and take pause.

By waiting to strike, you usually realise you don’t actually have to. And if you do, you can act in a deliberate fashion. Any hot emotions have simmered into a more meaningful and cool determination. Physiological evidence also indicates that access to the rational part of our brain is essentially cut off when we’re stressed. We instinctively begin our “fight or flight” response. Knowing this, I’ve tried to err toward temporary flight. Instead of immediately fighting back, or leaving, it’s best to strike whilst the iron is cold.


This week’s espresso shots

👨🏻‍💼 Ray Dalio on Paradigm Shifts - Ray Dalio has made the case for investing in gold as central banks devalue currencies. The hedge-fund boss predicts a "paradigm shift" in investing. Dalio said too many investors have been pushed into stocks and other equity-like assets and are likely to face diminishing returns. 

👑 Farnham Street’s take on Peter Thiel’s ‘Zero to One’ - I’ve been a long fan of Shane Parish and Farnham Street — in this brief article the talks about a book that Peter Thiel co-authored a couple of years ago. “Zero To One is an exercise in thinking — about questioning and rethinking received wisdom in order to create the future. And thinking about thinking is what we’re all about.” I’ve probably read the book 10+ times. And whether you love or hate Thiel, he raises great points on what you should be optimising for as a company founder.

🤡 Boris Johnson is set to become the next UK prime minister. Quartz puts it rather well in saying “in 2019—the age of Trump and rampant populism—that vote for Johnson feels very different. So why do we vote for leaders who are good enough, rather than good?” 

🛠 Have we reached peak tech? WeWork co-founder reportedly cashing out more than $700m. As WeWork gears up for an IPO, its co-founder and CEO Adam Neumann is reportedly selling off the company's stock. Unnamed sources told the Wall Street Journal that Neumann has cashed out more than $700 million from WeWork through stock and debt. It isn't uncommon for execs to cash in on a start-up's success, but doing so in the run-up to going public can send investors mixed signals about the CEO's confidence in the company. Despite the sell-off, Neuman remains the company's largest single shareholder.

📉 Fed Chairman hints at first interest rate cut in over a decade. The US looks increasingly likely to cut interest rates for the first time in over a decade, the Federal Reserve chairman, Jerome Powell, hinted on Wednesday. “Many” Fed officials now believe a weakening global economy and rising trade tensions have strengthened the case for a rate cut, Powell wrote in a report released ahead of his appearance before Congress.

Coffee & chats (longer form piece)

This week I wanted to talk about kindness & giving. So many people go through life ascertaining each interaction selfishly, in the form of “what can I get from this” — not batting an eyelid, nearly like they are entitled to whatever they wish for. It happens to me time and time again. People reach out for help, and they don’t actually want any help in how to approach a problem, they just want their problem solved for them. 

Take the modern job market as an example.

For someone who has grown up “entitled” — when they apply to a job, they’d expect their glowing CV / resume to open the door and a conversation to ensue. That may be the case. But there’s a tonne of smart hard working people out there. So by going this selfish, ego-driven, route — you’re going to risk not getting an interview. Your expectations will actually be your downfall.

If you approach it from a different angle. Think about a candidate who is kind, smart thinking, (and most likely humble) — they will think about how they can help the company before they’ve even got an interview. They’ll work on a project that showcases their ability to self start and problem solve.

I raise this today as I think it’s something specific to my generation (and the generations to follow). People are too pampered and spoiled. They expect that if they moan long enough they will eventually get whatever they want. Simon Sinek has a great video on it. And one of my favourite quotes: 

The generation, that we call the Millennials, too many of them grew up subject to, not my words, failed parenting strategies. Where, for example, they were told that they were special… all the time, they were told that they can have anything they want in life, just because they want it.

He goes on to say:

So, you take this group of people, and they graduate school, and they get a job, and they’re thrust into the real world. And in an instant they find out they’re not special their moms can’t get them a promotion; that you get nothing for coming in last and, by the way, you can’t just have it because you want it. And in an instant, their entire self-image is shattered. And so you have an entire generation that’s growing up with lower self-esteem than previous generations.

So I guess this was a long way of saying, don’t approach each situation in terms of what you can extract from it. Approach it in terms of what you can contribute.

No act of kindness, no matter how small, is ever wasted.” - Aesop


Bonus section; stumbled upon this answer on Quora, and thought it boded well for us all to remember as we go into the week ahead:

What are the most valuable life lessons you have learned? 

  1. If you don’t ask, the answer is no.

  2. You can get much farther with love than with fear.

  3. When life gives you lemons, make lemonade.

  4. The most important person you need to be accountable to and make happy is you.

  5. Draw your boundaries and protect them viciously.

  6. Things don’t make us happy, experiences do.

  7. If you’re too comfortable, you’re not growing.


P.S. did you know there’s a paid version that gets sent out 2-3 times per week?

That’s it folks, I hope you enjoyed this first newsletter. Again, if you did — please share it with your friends! See you next Sunday (hopefully) 🗓