Startup Coaching: How Startups Get Suckered

A legitimate business coach can be a windfall, a bad one can wreck your company

Joe Procopio
6 min readFeb 4, 2021


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I’ve never been a fan of coaching in the business sense, but I understand it.

Maybe it’s because I grew up playing a lot of different sports. I’ve had great coaches and I’ve had awful coaches. The great ones pushed me to places I couldn’t get to on my own. The awful ones mostly made we want to never play that sport again.

Now apply this to business and startup. A good coach might add a lot of value, provided the skills are already there and the coaching is individualized. A bad coach can take a promising business and crush it.

The key is in identifying good coaches and bad coaches. This is much easier to do in a sports context, where motivation and the adherence to sound, proven techniques are the primary ingredients for success. But the rules for success in business, and especially startup, change almost daily.

For example, the crow-hop technique to throw a baseball has been around for over 100 years. Anyone can learn it in an afternoon and instantly increase their throwing range.

Negotiating a term sheet requires financial, legal, and even technical experience that no amount of positive motivational reinforcement is going to substitute for.

So let’s talk about startup coaching — what it is, when it’s legit, and when it might not be.

What exactly is startup coaching?

Before I get (really well-written) hate mail, let me assure you that there are indeed legitimate startup coaches out there

Like most scams in startup, even in general business, there are always honest versions of all the sketchy impostors, and this is true for coaches as well. In fact, it’s the success produced by legitimate coaching that winds up breeding sketchy variants. After all, the most believable lies are always based on a nugget of truth — something I pointed out about public investor pitch contests.

In short, startup coaching is intended to make a startup leader or founder better at navigating the challenges in leading their unique startup.



Joe Procopio

I'm a multi-exit, multi-failure entrepreneur. NLG pioneer. Building & GROWERS. Write at and More at