Coaching your business from its teen phase to adulthood — Ask anyone who’s worked at more than one startup and they’ll probably tell you the same thing: Young companies start to go off the rails once they hit 50 employees. I call this the “teenager” startup phase, and I’ve been there several times, both as an employee and an executive. …

Save the big announcements for big deals — If you want to give your new business a decent shot at success, you need to build traction — clear, measurable evidence that people are interested in what your company is offering. And that won’t happen on Day One. So why do startups make big, splashy announcements the day they…

The more revenue you have coming in, the better the chances you can raise (and not waste) investor funds — At startups, the difference between survival and running out of runway always comes down to taking our eyes off revenue. We don’t want to do this, and we certainly don’t do it on purpose. But when we’re in the middle of the startup run, it’s pretty easy to fall into…

Before you scale you need to grow, before you grow you need to sell — Sometimes we forget that starting a business is about selling customers things they need. You can probably blame the equity-meets-live-action theater of Shark Tank for that. Or maybe it’s the stylized chase of the billion-dollar valuation in the Facebook movie The Social Network. You could even throw shade at the…

Where I learned the sneaky value in hearing the answer to someone else’s question — When you’re an entrepreneur, there’s no such thing as a stupid question. That said, most entrepreneurs aren’t afraid to ask stupid questions. But they’re super hesitant to ask a question when they’re not sure how to ask it. So what they do, in my experience anyway, is they ignore whatever…

It’s kinda their own fault — If you’re an entrepreneur and didn’t get the pants scared off you last week reading the “leaked” YCombinator founder memo calling for their incubees to go to the mattresses, don’t bother. It’ll only fill you with dread. You may also want to steer clear of all the subsequent memos that…

How hockey stick growth expectations get in the way of goals — It’s a phenomenon that happens to a lot of startup founders and leaders. It definitely happened to an entrepreneur I’ll call “Jeff,” who reached out to me a couple weeks ago. Jeff is a repeat founder, now in the early stages helming his second startup, after exiting his first through…

DIY is DIY, doesn’t matter if it’s applied to code, marketing, finance or whatever — If you’re going to tell someone what they should do, you should have already done it yourself. This is one of the tenets I’ve built into the Teaching Startup answers-to-your-inbox advice model. If one of our advisors isn’t doing (or hasn’t done) the thing they’re about to tell someone else…

Most entrepreneurs define success incorrectly and then never get there — Having been an entrepreneur for over two decades, I think about success a lot, but not in the way you might think. I’m sure you’ve asked yourself what success means to you. …