TL;DR: "How do I grow my startup and take on bigger opportunities if I'm too small to pitch them? Do I need to wait until I'm big enough or more fully formed to go after more customers and investors? How do I know when the time is right?"
The only way we grow is to bite off way more than we can chew.
There's this notion, however, that the way startups are built is by first building the entire product, team, and infrastructure, and then attacking our market. While that sounds fantastic, it's actually not how startups grow.
We grow when we take giant leaps that are way beyond our current capacity and then figure it out from there. In order to do that, we need to feel comfortable with taking these steps.
Am I Lying?
The first problem we all deal with is feeling like a fraud. We assume that if we're not 100% ready today, then we shouldn't even attempt to pitch our product to customers or investors. If that were true, startups would never get past a single Founder.
The reality is that we're constantly overselling ourselves. That's how we grow. The difference is how we deliver on those big claims. If we make big promises and fall short — that's on us. But if we make those same big promises and deliver, that's called growth. We can't predict the future (shit happens) but we can become laser focused on backing up our claims.
What if I Fail?
Sometimes we take a huge swing and whiff entirely. But we get so anxious about potentially swinging and missing that we fail to swing at all, which is way worse. What we tend to forget about is that our "misses" are never quite that binary.
Let's say we've got a consulting business and we promise a new client that we'll put 5 new staff members (that we don't have) on the account. When the time comes, we fall short, and only get 3 new members on the account. Initially, we think "Well we missed, so it's a total fail." Not necessarily.
We may find that we have to push our 3 new hires harder. We may spend some time resetting the client's expectations. We may find out it only took 3 people. There are a million versions of how things might not work out, but they don't all end in abject failure. In fact, that's usually the least likely case.
The Cost of Not Swinging
What we should actually be focused on is the cost of NOT taking those swings. Every time we back down we actually hinder the growth of our startup. Our lack of confidence is as much a barrier to our success as the prospect of failure.
It's worth noting, too, that nothing builds confidence in ourselves or our teams like big swings and big wins. The more we make, the more we're willing to step up and make again. We have to think about these big swings as conditioning our team to win, and we only do that when we're willing to step up.
The funny thing is — there's never a "good" time. The time to take the leap is now, and it will always be now. JFDI.