Matt Higgins

You need to structure your big bets in life to give yourself time to be right. It’s hard enough to be right, it’s impossible to predict when you’ll be right. ... I tell people it takes at least three years for a startup to stabilize, five to reap the harvest—and almost never less, no matter the product.

I process failure in four stages: 1. I have failed. 2. But I am not a failure. 3. I will unearth what failure was trying to teach me. 4. And next time, I will win.

Intrinsic motivations borne of personal experience are the most valuable assets we possess. No visions are ever rendered to us in the dead of the night that we are incapable of pursuing at the break of dawn. But we have to give ourselves permission to see them and then act on them.

Opportunity is not an inexhaustible resource, and when you see an opening you have to take advantage.

I’ve seen hesitation kill more deals than speed ever will. And when you hesitate, or when you hedge, or when you divide your attention between your goal and the safety net you think you need to build, it all just begs the question: What are you waiting for?

I believe you dilute your doubt by cultivating your conviction. The degree to which you diversify should have an inverse relationship with how convinced you are of your success. It is counterproductive to spread your energy across a landscape of opportunities such that you can’t actually invest your full self into any of them.

The best leaders make decisions that masquerade as data-driven choices when they are actually what I call gut sandwiches: data sandwiched between insights and intuition that we can’t justify with numbers alone. Game-changing ideas have too many ingredients to be reduced to a formula.

No te quaesiveras extra. It’s the first line of Emerson’s ‘Self-Reliance,’ and in Latin it means, ‘Do not seek outside thyself.’

If you are someone who is worried that you won’t succeed, trust me, you’ve already failed.

It’s hard to achieve greatness if you’re spending mental energy trying to rein yourself in. When I talk about going all in, it’s not just about eliminating backup plans and hedges—it’s also literally about putting all of yourself into the endeavor, and not holding back.