How to Live an Asymmetric Life: 4 Rules from a Private Equity Investor

Graham Weaver is the Founder of Alpine Investors and a lecturer at Stanford Business School. A couple of years back he delivered a standout lecture “How to Live an Asymmetric Life”, which jolted us out of our comfort zone. It’s something we, at Investability, still reference to this day (the follow up lecture “How to Live your Life at Full Power” is equally good).

If you haven’t watched it, let us fill you in… Weaver opens with a brutal moment. Sitting across from Joe, the largest investor in Weaver’s PE fund and a personal mentor – someone who believed in him early on, when not many others would. Weaver has to deliver the harrowing news that he’s lost half of Joe’s money – his significant, personal (PA) investment.

But that failure taught Weaver a powerful truth – playing it safe and protecting the downside actually doesn’t protect you. It just keeps you from ever breaking out.

It prompted a turning point. After applying the principles of asymmetry to investing, Weaver began to realise that the principles were even more powerful when applied to other areas of life. And they stacked logarithmically – integrate one, and you’ll see meaningful improvement. Apply two or three, and you start to build real momentum. If you can run the table and apply all four of these principles, it becomes difficult not to lead an extraordinary life.

If you’re working on something ambitious and need a growth-focused IR partner to help bring it to life, we’d love to hear from you.

And now, let’s dive in…

Here’s four principles to help you start placing more thoughtful, higher-conviction bets.

1. Do Hard Things

If you want to have an asymmetric life, do hard things. Progress almost always is preceded by discomfort. Any change you are going to make to better your life is almost always going to make your life worse first. Whether it’s ending a relationship to get the relationship you want, having a tough conversation, starting a new exercise regime, learning something new – it’s going to get worse first.

Weaver’s chart showing everything you want in this life is on the other side of “worse first”

Weaver argues that all meaningful change is proceeded by a dip – a period where things get harder before they get better. But the biggest part of the downward curve is just fear. Don’t mistake that fear or discomfort for failure. It’s just the price of admission to real growth.

If you want to live an asymmetric life: Do hard things.

**2. Do Your Thing**

At a dinner in New York, Weaver found himself seated next to a fellow investor enthusiastically discussing debt covenants. In that moment, it hit him: you can’t win chasing someone else’s dream.

Nearly 2,800 years ago, Buddha articulated a core truth that still resonates today: “Life is suffering. So figure out something worth suffering for.” Success is deeply personal; pursuing someone else’s dream may offer short-term stability, but it rarely leads to long-term fulfilment or success.

Weaver adds that when faced with choices about what we want to do, most of us miss one important piece of the equation. We factor in all the risks and tradeoffs, but we completely discount how differently we will show up when we’re truly energised about something. When our whole being is fully invested, we tap into a superpower, and we can sustain that for a long time. You won’t tap into this power as long as you’re living someone else’s dream. Play your own game or risk becoming average at someone else’s.

If you want to have an asymmetric life, do hard things but do your thing.

3. Do It For Decades

Like compound returns, success takes time. There’s no shortage of promoters promising 10x returns in 10 minutes. Weaver’s advice? Ignore them. Consistent effort, year after year, is where momentum builds.

The equation for returns is X = (1+R)^N, where N is quadratic. Consider this equation where X represents your competence in any given role. The R represents everything you’re doing to improve yourself: coaching, reading, learning, writing out your goals, using your imagination, etc. The most powerful part of the equation is the N, the number of years you dedicate to something. If you love what you do, you will do it for a long time, and your N will be large. And if you improve at a reasonable rate over a long period, you can become the best in the world at what you do.

As Weaver puts it: “There is almost no obstacle that won’t yield to you at your full power, excited about something, for a decade or longer.”

If you want to live an asymmetric life: Do hard things. Do your thing. Do it for decades.

4. Write Your Story

Weaver’s final rule is about vision. Write your future – five years from now – and write the story as if it’s already happened. Don’t get caught up in the “how.” That comes later. Why five years? It’s a time horizon that allows for a balance between long-term vision and achievable milestones.

Here’s what you need to do:

Describe your [life / company / dream scenario] five years from now, in detail. Get out of the fog of war in front of your face.
Describe it as the outcome you would want if you knew you would not fail.
Remember, the ‘how’ is the killer of all great dreams. So, don’t worry about how you will achieve any of the story as you’re writing it. Just write it down.

Visualising outcomes helps align your behaviour, choices, and relationships around your goals. When you know what you’re aiming for, your decision-making becomes sharper.

No matter where you are in your life right now, you can write a new story. If you want to live an asymmetric life: Do hard things. Do your thing. Do it for decades. Write your story.

Final Word

Going after asymmetric returns is about more than investment theory. Applied to your life, it’s about setting your target price so high so as to scream (to yourself) that you are your highest conviction trade.

One of the biggest things that will hold you back is fear. Fear is a master manipulator and often disguises itself as somehow keeping you safe. It’s easy to mistake hesitation as being sensible or avoiding risk, but over time, it can become a pattern of inertia.

The principles above offer an antidote to fear: a framework for decision-making that shifts the focus from risk avoidance to positioning yourself thoughtfully for asymmetric outcomes and achieving your long-term potential.

So, to summarise:

Now is a good time to do the hard thing. Whatever you’ve been fearing – go do that. Whatever you’re putting off – do that. Because everything you want in this life is on the other side of “worse first.”
Now is a good time to pursue your own direction. No matter what path you choose, you will suffer. But know this – some things are worth suffering for. Back yourself. As your life goes on, you will realise how precious it really is, and you don’t want to spend it living someone else’s life.
Now is a good time to commit for decades. Great things take time but know there is almost no obstacle that won’t yield to you at full power – have grit and persistence.
Now is a good time to define the shape of your own life. If you’ve read this far it’s very likely you have a magical vision for your life. Take the time to write it down as if it’s already happened. You may be amazed by what happens next.

If you’re building something big and looking for a growth-orientated investor relations partner who will help you achieve your audacious goals, get in touch via our contact page or email us directly: info@investability.com.au.

How to Live an Asymmetric Life: 4 Rules from a Private Equity Investor