Notes to the Next Founder

2.25 decades of entrepreneurship will make you or break you — usually both — on an hourly, weekly, monthly, and yearly basis.

And still, for me… it’s art.

I’m writing this for the corporate drone, the aspiring founder, and especially the idea-obsessed, action-averse soul. I don’t blame you for waiting. It’s heady out here.

Let’s begin with the truth:

No one — not your friends, family, investors, or even early customers — believes a word you say. They only believe what you do.

So: be about it.

Here’s a quick gut-check to see if you’ve got it for entrepreneurship:

  • Is “no” your favorite word?

  • Is mental loneliness familiar territory?

  • Can you live broke for a long time?

  • Can you change your mind — often?

  • Can you survive without a plan?

  • When everything fails, do you still show up?

If you answered yes across the board…

I’ll save you the heartache: welcome to the path. You’ll make it.

But let’s run one more to be sure:

Do you feel special?

If the answer is no…

Read on, comrade.

Here’s what’s up:

  • If you’re a 1–3 person services business: invoice from an alias like finance@ or billing@. Follow up immediately from that same address. Set the tone.

  • Two founders are better than three. Starting a company is like ordering a pizza. One person wants Hawaiian, the other wants pepperoni. You settle on half-and-half… but guess what? The third person still wants pepperoni — and everyone knows Hawaiian sucks.

  • Raising money is easier than getting a mortgage. But it will require you to step far outside your comfort zone. Don’t rely on friends and family. You’ll need strangers to believe in you.

  • Even in the darkest hours: show up. Show up. Show up.

  • Envy — not money — is the root of evil. Cheer for the ones who win the right way. Ignore the ones who cheat.

  • Marry well. Choose someone who says yes more often than no. Someone who sees the glass as half full more than empty.

  • Put yourself out there. The loudest voices in your head often come from people closest to you who don’t understand what you’re doing — until you do. Don’t let anyone slow you down. The real hater is probably you.

  • A little delusion is healthy.

  • Being multi-dimensional isn’t a flaw — it’s your edge.

  • As Pop says: If you know you’re right — and good-looking — go for it.

You’re ready.

I’m rooting for you. Always.

— MM

Mark Ashley