Learn to think big

I often get asked to give advice to people starting on the startup career path. I didn't have an obvious starting point until now.

You should learn to think big. It's the precursor to choosing an ambitious startup idea, which I also strongly recommend.

Unfortunately, thinking big is easier advised than explained. It's hard to explain because thinking big is one of those things that you don't know you're doing wrong until you're doing it right. It's kind of like a high-school relationship vs a good marriage, which I realize is an analogy that also doesn't help a lot of people.

The good news is there is an easy path to getting there quickly -- get a good mentor who already thinks big and then they can keep telling you that you're not thinking big enough or not thinking the right kind of big until you are. In retrospect, this is probably the most concrete thing I know I could have done better years earlier if I had utilized mentors more effectively.

I didn't start to truly grasp thinking big until 2010. That's a decade after doing startups full-time and when I was already thirty. I can't point to one particular moment, but looking back I think I finally got there through a combination of starting to angel invest (and seeing my portfolio struggling with this), committing to blogging for that year (and the benefits that come with it), and starting to see how DuckDuckGo could eventually make a real dent in the search market.

It wasn't for lack of confidence. I've been pretty confident since high school. And it's not like I wasn't doing relatively big or unique things through my twenties. For example, I started and sold a company for millions of dollars.

That may seem like it is only possible through thinking big. But that's not true. I was thinking very small. I was thinking how I personally could make a successful business.

And in that case I took this small thinking to the extreme, which makes it a particularly compelling example. I wrote every line of code and we never hired any employees from beginning to exit. That kind of thinking doesn't scale and it won't maximize your chance of making real change in the world, which I believe is real startup success.

However, it may make you just as much money. And that's an important distinction. Thinking big and making money are not the same thing. If your goal is to make money then an indie company (like my last one) may be your best bet, or some other industry altogether like finance.

But if your primary goal is to change the world, then the first thing you should do is learn to think big. I suggest working on real plan that sketches out how your vision could impact the world. What does your vision look like at scale? How many people or businesses could you possibly impact? How would you change what people do or how they think on a day to day basis?

I've repeatedly seen two common ways this is messed up. First, like I did, you only focus on the first million. This leads to niche ideas in smaller markets and a lack of long-term planning that will bite you when you get to that million.

Second, you put too much detail into what things look like five years from now. You should have a detailed 12-18 month plan, a good sketch for 24-36 months and rough ideas thereafter. The wrong approach here is saying in version 5 we're going to build this and that feature and have these revenue streams because you have no idea right now. In other words you shouldn't have a consistent level of detail but a rapidly declining one. But you can and should have a rough idea of what changes your product may bring if it is a market leader in a large market and how it might evolve to that reality.

The trickiest part about thinking big is you still need to think small at the same time while executing. You need that grand vision, but you also need to bring that back to today in the form of strategy, goals, priorities and of course your very next steps. Being able to articulate both the big and small in a succinct way that makes plausible sense is a signal of a great entrepreneur.

In fact I arguably should have titled this Learn to think big and small since that is ultimately what you need to do, but really I don't see too many people just thinking big except for wannabe entrepreneurs. As soon as you make your first move, you're thinking small because you have to start somewhere and do something.

From the investor point of view, I see a lot of thinking small but not a too lot of cohesive big visions and that's why I have a hunch that the lack of thinking big (often manifest in those above two ways) is the biggest disconnect between startup founders and investors. Looking back at my own wall of shame I think that it is the strongest signal that I missed in ultimately successful companies that I passed on that also wasn't present in ultimately less successful startups.

I don't believe there are any necessary or sufficient conditions in startup success, but along with questioning your operating assumptions enough, learning to think big is another one the key ways to maximize its likelihood.