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…

Teaching Startup is going to help you discover why your users aren’t using what you’re giving them — I’ve been founding startups, building products, and helping others do the same for over 20 years. In that time, I’ve learned that one of the most frustrating puzzles for a startup leader to solve is why customers aren’t using their product. They usually wind up landing on the wrong reason…

There’s Always a Fine Line Between the Future and a Scam — Another day, another crypto/NFT/DeFi scam. If you want a handy transcript of web3 carnage, you can fall down the rabbit hole reading web3 is going just great, former HubSpot developer Molly White’s blow-by-blow account of the seedy underbelly of crypto/NFT/DeFi rug pulls, exploits, wipe-outs, and other shenanigans. I mean, I…

Build Your Marketing Stack With an Anti-Incumbent Strategy — How do you fight multi-billion-dollar companies with a startup’s limited resources? Almost every startup operates in an industry that’s “owned” by a few legacy players. And one of the primary reasons these young startups fail — whether from lack of traction or lack of investment — is because at any…

And how we show other startup leaders how to do that — When I first launched the Teaching Startup minimum viable product two years ago, I immediately opened channels with my beta group asking them what additional features they wanted to see. And then I wound up outright rejecting the very first feature most of them asked for. Finding the right balance…

Successful startups have been getting ripped off forever — If you didn’t read Eco founder Andy Bromberg’s Twitter thread last month accusing Pebble’s cofounding team of the boldface plagiarism of both Eco’s marketing messaging and business model — along with a blow-by-blow accounting of what he called “lying and espionage” in attempts to surface Eco’s intellectual property, you’d be…

You need resources quickly. Should you hire friends and family? — At what point does your employee become your friend and at what point does your friend become your employee? This is one of my least favorite questions. And I get it more often than you’d think. Because it’s where a lot of startups fall apart for the worst possible reasons. …