This Is The Least You Can Do When You’re Pitched An Idea

Write a list about why it will fail.

In January I joined Gautam Mishra on a quick around-the-world trip to connect with investors. Gautam recounted Inkl’s origin story in each meeting and one act he performed religiously in the early days in response to each pitch struck a chord with me.

If a new venture is in your future, you should follow Gautam’s lead.

But first, what happens when you’re pitched an idea?

For starters, you’re facing another human who has mustered the courage to share the vision they’ve been obsessing over for weeks, if not months.

They practice their pitch before going to bed, in the shower, countless times during their day and again before bedtime.

The opportunity that awaits, in their mind, is crystal clear. The value to be captured is ripe for the taking and the path to the way ‘things will be’ is just a few steps away.

It’s that simple.

Or it is until they pitch it to you.

Watch closely as they start their pitch. They’re summoning 99% of their energy to communicate the most compelling set of messages they hope you’ve ever heard. The remaining 1% is focused on simultaneously processing your every cue, from the notes you jot down to your facial expressions. Don’t be surprised if some of these acts result in slight corrections to the intended messages.

Right now the person opposite you is as vulnerable as their fledgling vision, which could very well be the next big thing.

They don’t have your context or experience and you don’t have theirs. All you need to do is listen hard, suspend judgement and hold onto the questions you’re itching to ask and the comments you’re desperate to make.


“Thank you, any questions?”

The pitch just ended. Here’s where you come in.

You’re about to draw on your experience and context to respond to what you’ve just heard.

And if like me you’re an optimist, you’ll hunt for value in new ideas and business models and try to help evolve the current thinking of the entrepreneur and their team. This might take the form of diving into unit economics, business development or looking at ways to accelerate traction (or anything in between where you can add value).

Of course it’s also just as easy to rattle off a long list of reasons why you think it will fail.

You might see the latter as lacking empathy but the truth is it’s probably a little more valuable. And this insight became Gautam’s super power as he set out to build Inkl.

In every early meeting Gautam sought to intimately understand, from news publishers and readers alike, why Inkl would fail.

After formulating his vision he set out to systematically solve each issue that his prospective partners and customers said would lead to failure. The rest is history and today Inkl’s marketplace metrics continue to impress.

“Why do you think [venture name] will fail?”

There are three reasons why it’s important to ask this question each time you pitch from now on.

1. It gives your audience permission to be candid

Time is valuable. The quicker someone believes they can be honest about their thoughts, the quicker you’ll have insights to examine and action. Without permission to speak candidly people can have the tendency to sugarcoat feedback and that’s less useful.

2. It demonstrates you’re prepared to learn and grow

Investors look for entrepreneurs who have the mettle to rapidly process and adjust to feedback signals. It’s a precursor to understanding how well they will perform when the going inevitably gets tough.

3. It gets people thinking

I’ve found that people who accept permission to be candid on why a model or venture will fail are the same people who offer up additional insight after the initial conversation. This has come in the form of ideas for product features, offers to test and introductions to other interested parties.


Next time you’re pitched an idea, think about responding with a constructive list of reasons why you think it will fail and ask if they’ve received similar feedback. It might be the most valuable email they receive this week.


Please hit recommend (❤) if you learned something and leave a comment below if you’d like to dive deeper.

You can also follow me on Twitter and subscribe to my personal newsletter to be notified when I release my next pieces.