Storytelling for entrepreneurs

Last week I met with a friend who’s a founder of a pre-IPO company. Two things we discussed struck me as fascinating:

(1) just like every other person (myself included) who’s obsessed with success, my friend, although insanely accomplished by most people’s standards, was comparing himself upwards. He was looking at companies that have achieved rare world-class success and felt dissatisfied with his progress. What a familiar pattern! And how funny it is that it never ends for ambitious people as we continue finding ever-renewing sources of upward benchmarking that cause us to feel unsatisfied with our progress, while observers would consider us extremely successful.

(2) we chatted about the challenges of managing a post-IPO company, one of which is managing the public opinion that determines the price of your stock. Although I’m nowhere close to dealing with an IPO, this sounded shockingly familiar. While the logistics of an IPO or of managing a public company are very different from raising typical VC funding, the determining factors of success remain the same: you have to tell the story of your company in a simple, yet compelling manner to get people to see the promising future of your company. If your story resonates, you win and people give you lots of money. If it doesn’t, your stock price drops. Facts are important, but public opinion is rarely based on facts alone. Even when the facts are there, humans look for the narrative to tie them together and give them context.

What did this all mean? For one, I was reminded that happiness and fulfillment are not derived from external circumstances. Thinking that they are is an illusion and a trap. More on that in later posts.

The second point was a reminder that the game doesn’t change as you grow and evolve. Regardless of the stage of the company, your biggest job as an entrepreneur is to continuously create and manage the story of your company for the world.

A critical point about storytelling is that stories are not fact or reality (yet). A story (a term I use very broadly) of a company usually focuses on creating the future to compel some sort of an action (investors giving you money, employees joining, etc.). The story starts as an idea (an imagined course of action) of a better future: a future where a particular problem is solved, your customer is delighted and the world is a happy place.

This future doesn’t exist. There is no one in the world who can make a reliable judgement on the probability of your version of the future existing (everyone tries, naturally). Investors try to come up with good justifications for their decisions, but they are human like the rest of us and all they have to go on is their judgement (see

Storytelling is a risky proposition. The future hasn’t happened yet and your story is not reality. You could easily be wrong! You could even — gasp! — fail! It takes real courage and commitment to continuously create your story for yourself and for the rest of the world.

Where do you find the courage to cross the gap between current reality and your vision of the future? You find it in the realization that there is no absolute authority and no one person who knows how things will go. And if there are no guarantees of the future, all you have is your commitment. There’s a gap, and the only way to cross is to jump.

Commitment is fascinating. True commitment is internally generated and is an acknowledgment of your ability to have agency (i.e. capacity to act), to be the source of experience and reality. It’s also the source of leadership. A leader is someone who commits to a vision and has the courage to put himself on the line for making his story a reality.

Most people want a definitive opinion on how the future will go because uncertainty is uncomfortable and it’s easier and safer to not be responsible for creating the future. Yet realizing that there are no authorities on the future and that nobody can tell you the final outcome of your efforts, gives you power. Your power is in your courage to create, commit to, and share your story.

Show your support

Clapping shows how much you appreciated Deena Varshavskaya’s story.