May you be blessed enough to make a thousand mistakes once, not one mistake a thousand times

I have a good friend (lets call him Bob) who worked at a Fortune 50 IT technology company for 21 years. After reaching the top of his organization (partnerships), he then left, for a startup to head up their partnership and business development efforts. He was their first “suit” / “business guy”. The startup was funded by a very well known venture firm in Sand Hill, had 21 people (mostly engineers, product managers and the like) and a hot product in the networking (infrastructure) space. The interview and courting lasted many months, so he was confident he made the right choice.

He could not have been more excited during the first week at work. There was creative energy and fresh thinking daily, new and yet unsolved problems that had no obvious solutions and he felt he was finally “learning again”.

In in the 2nd week the cofounders and he had a catch-up lunch, when they told him “they needed to go another direction and his position was to be eliminated” and they’d like him to leave. No other reason was given, but just that they were not ready for a BD person at this time, since the company was going to pursue another route.

I recall him telling me over lunch a few weeks later, when he mentioned that he was not totally shocked, but it surprised him for sure. We did some Monday-morning quarterbacking and figured it must have been either his inability to fit into their “culture”, which was very developer-centric or his relatively higher salary.

A few years went by and he continued to be friends with the co-founders and met one of them for a catch-up lunch.

The conversation was enlightening for sure. The co-founder was more candid and particularly said “most of the engineers said the amount and breadth of experience that my friend possessed was narrow and limiting”. Which shocked Bob, since he had really “21 years of experience”. He had dealt with all types of ISV‘s – small and large, had experience with all the system integrators, from consultants to outsourcers and had connections at every level.

The cofounder then said “Yes, but you did practically the same thing for 21 years, not 21 different things in a year”, which skewed your thinking to solving every problem literally the same way.

Bob was shocked for sure, but he took it in stride and in the meanwhile had started his own BD consulting company, helping many startups navigate the large ecosystem of partners.

Over the next 2 years of his consulting he claimed to learn a lot more than he had in his 20+ years at the F50.

What did he learn that he did not know before?

“I found more ways I could be wrong and more mistakes I made daily” he said. “With a large brand name on my business card, those mistakes were largely ignored. They were a lot more magnified when you are dealing with others who now have that large brand name on their business card.”

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3 thoughts on “May you be blessed enough to make a thousand mistakes once, not one mistake a thousand times”

  1. My feelings exactly! In the past few yrs. that I became an entrepreneur, I have learnt so much not just about technology or domain but also about life that I couldn’t have if had continued working for someone else. A great way to live many lives in just a single one. Isn’t it 🙂

  2. Was getting the feeling that I have stopped doing those mistakes since I’ve been in this job for a while now … Time to head out and start doing some ! Thanks Mukund

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