Elimination is a powerful tool. Living in a world of abundance, what we say NO to is becoming far more important than what we allow to happen. What not to do as a Founder is as (or more) critical as everything that people would tell you to focus on.
“There’s something powerful in knowing what not to do.“
I’m sharing below the top 4 things from my personal experience at PopUp72.com, that will almost guarantee failure.
- Keeping “busy”
Most founders have ambition and self assurance as key traits. When there is lack of actual progress (which would be many weeks or months in this journey), self assuring people tend to find ways to convince themselves that they’re “at it”. By doing stuff. Stuff that may not be important.
Bias for Action is good, Action Bias is dangerous.
Reminds me of a Sheldon Cooper quote
“I never said that you’re not good at what you do. It’s just that what you do is not worth doing.”
How to Fail? Keep working 15-hour days without evaluating highest impact paths.
- Playing too safe
“Ships in the harbour are safe. But that’s not what ships are built for”
I’m skeptical of the term “calculated risk”. Calculated risk is basically strategy. Risk is what’s left over after you think that you’ve thought of everything. It’s what no one sees coming. And being ready (in fact excited) to take this real risk on a daily basis, is almost a mandatory requirement in a start-up.
How to Fail? Get scared of uncertainty and overthink. Think in straight lines. Have self pity.
- Not knowing your role
It’s tough for early-stage startups to have clear role demarcations, mainly because the sheer workload always surpasses resources. The founder’s time however is a critical resource and must only be used for the hardest problems. Sure, you must get your hands dirty from time to time, but being mindful of when to be a player, captain, or coach creates ownership in rest of the team.
How to Fail? Try to do everything, be everyone. Fail to delegate and hold people accountable. Hire people with no ownership.
If you’re a single person business (which will surely become more common with AI), feel free to ignore this point
- Pessimism
“Entrepreneurship is like jumping off a cliff with the hope of building a plane on the way down.”
That’s probably the level of optimism (borderline insanity?) needed. Aren’t the most successful founders just fiercely optimistic? There is no other way. If 90% of businesses fail, starting one automatically places founders in the top percentile of optimists! Keeping it that way on the toughest days is harder, but critical. Spiralling down is the easiest thing – and grit will be tested to its core.
I do say “Hope is not a strategy”, but sometimes hope is all you need! Of course, we need to make robust plans & execute with rigour, but in the darkest moments, only logic may not be enough to keep you going.
How to Fail? Lose conviction in the idea you once thought can shake up an industry. Think more of why it could fail vs how it could succeed.
Sharing 3 of my favourite entrepreneurial stories / books
- Shoe Dog: A Memoir by the Creator of Nike | Phil Knight
- Masters of Scale | Reid Hoffman
- Same as Ever | Morgan Housel
Shrey Kapoor 
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