Introducing Chief Dark Cloud, Startup Whisperer!

“There’s nothing more exhilarating than pointing out the shortcomings of other people.” — Jeff Anderson. Clerks.

Elijah Tahamont aka Chief Dark Cloud. Source:

Being semi-retired these days means I have a lot of time on my hands. The three hours I spend on the bicycle every morning, for example, are prime thinking hours: thinking about ways to help the startups I’m advising, about business plans for my own ideas, about my next blog post, and given the lack of oxygen to the brain due to extreme exertion, also about many harebrained ideas as well.

A case in point is the story of my latest alter ego, Chief Dark Cloud, as I was recently christened by relatives — a title which, admittedly, is well-deserved. As friends and family will tell you, I am a master nay-sayer, a sourpuss, a grumpy cat. I love telling everyone (including myself) why their latest idea won’t work, why they’re managing their engineering team incorrectly, why their company (or product) will fail.

When it comes to social matters, I pretty much stick to the same script, telling everyone why it’s a bad idea to buy this car or that house, why they’re not raising their kids properly, and why western society in general is doomed. The list goes on and on.

There isn’t a day that friends and family don’t interrupt another one of my rants with: “Ah… I see it’s Chief Dark Cloud speaking again.” Nothing is ever good enough for the Chief, it seems. He can’t help but rain on every parade. He does so instinctively and with the best of intentions, not out of any malice.

In my defense, at least in the case of work, I claim “experience” — which just means I’ve already made all the mistakes they’re about to make. Having been around the industry for so long, I’ve pretty much seen all the reasons why a project fails so it’s easy to detect a pattern when I see it. The team on the ground, often through no fault of their own, are too busy fighting day to day battles to look three years ahead — where they need to be looking.

What most startup founders often don’t seem to internalize is that you don’t just need a great technical idea or an under-served niche or a kick-ass engineering team or an excellent go-to-market plan or a cool advertising campaign or a strong sales team or a wonderful customer service experience in order to win. You need all of the above and a lot more to succeed in today’s competitive environment.

A VP of Engineering at a startup I was advising recently said in parting: “I think of your coaching as a dunk in ice water… once I’ve had it, I have plenty to go run with for a while (just thinking of the pain of the ice bath!) but would love another dunk when I warm up too much.” I took it as a compliment. Thanks for the advice, Chief Dark Cloud. I needed that. But, just like a freezing shower, I’m fine with… err… a lower frequency of repetition.

It turns out that Chief Dark Cloud is a real person who even has his own Wikipedia page. He was an Native American chief who became a Hollywood actor and appeared in dozens of silent movies. Since he died exactly a hundred years ago in 1918, it seems befitting that his spirit has now been been resurrected in me. Sort of like the reincarnated Buddha, but not exactly!

So, as I was huffing and puffing up the mountain recently, I had a seemingly brilliant idea. Why not start a new podcast? Chief Dark Cloud will interview startup founders and review their business plan, technology strategy, engineering plan, architecture diagrams, go-to-market strategy, etc.

Invariably, of course, the Chief will tell them why their idea will never work, why they’ll screw up (or have already screwed up) either the engineering or the marketing or the sales or the talent retention or something.

Think of it like the Soup Nazi for startups but with a Native American bent: No money for you, Kimosabe!

Our advertisers will be cool startups trying to recruit engineers and business people who happen to be our main audience. Come join, where we do engineering right! Or perhaps I could offer a subscription model: Learn from the mistakes of others for only $9.99/month.

Best of all, Chief Dark Cloud will personally invest in your startup if he agrees with your plan. But don’t count on it. Like Grumpy Cat, he is very hard to please. Only the best need apply. Send an email to if you’re interested in participating.

But, Ben, why would any startup want their secrets revealed to the world on a podcast?

Dammit, I knew I was missing something. Never mind. I have lots of other cool ideas on my rides. Did I ever tell you about my drone-based autonomous lawn mower idea? Or, as a colleague dubbed it, The Flying Lawnmower of Death!

Former CTO of VMware, former VP at Microsoft, recovering long distance runner, avid cyclist, newly minted grandpa.

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