Letters from the Trenches

Why “Throw Deep” is a Good Strategy

Why “Throw Deep” is a Good Strategy

Suppose you want to get ahead of the competition and be a juicy acquisition target. In that case, one of the best strategies is to forget the commoditized benefits everyone in your magic quadrant has and go for the touchdown pass by developing the most advanced and most complex ones first. The ones the competition doesn’t yet have, but you know they’ll be going there soon. Only then go back and either get the commoditized benefits off the shelf or develop them yourself, if necessary.

How to Shoot Yourself in the Foot and Have Fun Doing It

How to Shoot Yourself in the Foot and Have Fun Doing It

Why it’s not very smart to post pics and videos of expensive settings, bragging about visiting exotic locales, snapping selfies on sailboats, wearing expensive watches while holding the wheel of a supercar, and generally acting like a rich asshole while you’re fundraising.

How to Align and Mesure Company Goals: a Case for OKRs

How to Align and Mesure Company Goals: a Case for OKRs

As you scale up your business keeping every single individual tightly aligned to achieve company goals is very difficult. You’re hiring lots of new talent every month while the complexity of your product expands, initiatives pop up, new departments are born and strategies evolve — so how do you make sure everyone is going in the same direction, understand the goals, and how do you measure that without killing the drive?

The Founder’s Syndrome: When it’s Time to Let Go?

The Founder’s Syndrome: When it’s Time to Let Go?

Running a startup and running a scaleup requires two very different skill sets. Very few founder-CEOs posses them both, and those who don’t will either stall the growth (and eventually sink the venture) or be replaced by the Board. Neither is very much fun, so let’s look at how you can avoid the Founder’s Syndrome or treat its symptoms that are epidemic in the entrepreneurial world. For a more rounded insight, please check out my blog on the Founder’s Dilemma.