Everything on the web, and in SaaS, these days is about going big. Larry Page at Google I/O wants Google to start doing brave new things that build billion dollar markets. Peter Thiel wants the best of us to skip college and go straight to building the next Pallantir and PayPal, just bigger. Elon Musk (bless him) takes out a $150,000,000 loan from Goldman (because even though he’s a so-called “billionaire”, it’s almost all paper money) to invest $100,000,000 into Tesla at a $10,000,000,000 valuation.
And the related message is: if you don’t Go Big, you’re not Part of It. You’re some sort of short-term loser, or at least, a penny player.
I get it. And you know what, I agree. If I did a third start-up as a co-founder … a big if … I wouldn’t settle for Less Than a Billion. Period. Not interested otherwise. Don’t talk to me about F-You Money, Selling to Google or Salesforce or whatever. I. Want. A. Billion.
But why?
The truth is, and I think this is especially true of Go Big VCs … Going Big … In Most Cases, It’s Just Math. Disguised as a Religion.
My obvious learning, with time and hindsight, is just this. In start-ups, you can’t do 10 companies at once as a founder. You can only do one. And in SaaS especially, it’s at least a 7-10 year journey. So you don’t get a ton of at-bats as a founder. Maybe 2-3 if you do well, a few more if you are Elon Musk. But even there, not much more than that. And even VCs, they only do 1-2 deals each a year, on average. It takes time for them too.
So let’s imagine you a centimillionaire VC or founder. (I’m not, but I can imagine). If you have $100m, and you start a company, or invest in a company, and you make $10,000,000. Then, dude, it wasn’t worth it. It’s too much work, and more importantly, too much time. Too much opportunity cost. You only added 10% to your balance sheet for all that work and time. If you have $100,000,000 … or $10,000,000 … or $1,000,000 … you need to shoot for An Order of Magnitude Bigger Next Time.
There no other way to grow, get ahead, and make the math of time and limited at-bats work.
So here’s the sometimes pernicious effect that comes from Order of Magnitude Math. The advice you get is heavily biased by the advisor’s Order of Magnitude Math. And that most likely won’t align with your math:
- If it’s your first start-up, period, you just want to learn.
- If it’s your first start-up as an executive, you want to learn how to manage, grow and scale.
- If it’s your first start-up as a founder, and it doesn’t totally explode relatively early … you just want a Real, True Win.
- If it’s your second-at-bat, and the first one was a success — you want 10x or more of the last one.
I want you to Go Big. And I want to Go Even Bigger Myself. Don’t get me wrong.
Just don’t necessarily listen to me, or them. Of course, don’t do something Small. That never pays.
But you change the world by doing great things, and then having great markets multiply the effects of those great things. Aim high. But get there the way that works for you and your team.

(Cross-posted @ saastr)
@Jason, thanks for this post, it’s a good perspective on this aspect of start-up culture.
It makes a lot of sense that there are stages to entrepreneurship, and I think a lot of folks see the big (or should I say huge) success stories and get a bit carried away. (I’ll admit to that myself while working on my project.) Instead, each stage should be about applying previous lessons and building on those to go bigger.
I guess, it’s not about ignoring the advice to go bigger as you say in your title, but rather aiming to go bigger in a staged way: Maybe call it Iterative Entrepreneurship.