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EntrepreneurshipShaan's Masterclass

The Four Beliefs Check-In

A yearly four-question audit of founder conviction that tells you whether it is time to sell.

Difficulty
Starter
Time to result
~days to results
Steps
5
Confidence
88%

Shaan Puri argues the first question in any sale process is not who will buy you, it is whether you even want to sell. When you start a company you hold four beliefs at once: this is going to work, this will be big if it works, I can do this, and I want to do this more than anything else. The test is to re-ask all four at year seven and score each one as more true, less true, or the same as when you started. When Shaan sold his first company, every belief held except this will be big if it works, and he judged that a medium-sized exit four years out was not worth four more years of his time. With Milk Road it was the fourth belief that broke: the business was working and could have been big, but his brain was wandering to new ideas and he was loving the podcast, so it was no longer the one thing he wanted to wake up and do with laser focus.

Origin

Shaan built the check-in after selling Bebo to Twitch and Milk Road to two private buyers, noticing that each decision came down to exactly one of the four founding beliefs breaking rather than to any offer on the table.

Core principles

  • 01Selling starts as a self-question, not a market question
  • 02Never run the check on your most frustrated day
  • 03Score direction of travel, not absolute conviction
  • 04Belief drives massive action, and no belief means no results
  • 05Time is the scarce asset, not the multiple

How to run it

  1. 1

    Recover your day-one beliefs

    Write out the four beliefs as you held them when you started: this is going to work, this will be big if it works, I can do this, and I want to do this more than anything else. That is the baseline you measure against.

    Pro tip Write them in your own original words, not a polished investor-deck version.

  2. 2

    Pick a neutral day to check in

    Schedule the review deliberately rather than letting it ambush you. A check-in run on your worst week measures your mood, not your business.

    Watch out A frustrated founder will fail all four questions on a Tuesday and pass all four on the Friday.

  3. 3

    Score each belief as a direction

    For each of the four, ask whether it is more true today, less true today, or the same as when you started. Direction of travel is the signal, not the absolute level.

    Pro tip If a belief is flat but the others are rising, that flat one is usually the real story.

  4. 4

    Isolate the belief that broke

    Name the single belief that has degraded most. Shaan's first exit failed only on this will be big if it works; Milk Road failed only on I want to do this more than anything else.

    Pro tip One broken belief is a reason to sell. Zero broken beliefs means keep building.

  5. 5

    Convert the answer into one of three moves

    If the right offer arrives, consider it. If you no longer believe in the business, sell the assets, because without belief you will not take massive action and will simply prove yourself right. If you just do not want to run it anymore, exit rather than hiring an operator you do not want to manage.

    Watch out Staying without belief is the worst option: no action, no results, and a self-fulfilling conclusion that it was never going to work.

In the wild

Bebo: the medium-sized exit that was not worth four more years

At the first company, Shaan scored all four beliefs and found they were broadly intact except for this will be big if it works. He judged the realistic path as a medium-sized exit roughly four years out, worth multiples of the current value but costing four more years of his life.

He sold rather than playing it out, on the reasoning that the multiple was real but the time was more precious.

Milk Road: a working business sold on the fourth belief

Milk Road was actually working and Shaan thought it could be big, so the first three beliefs held. What broke was the fourth: his brain was wandering to new ideas and he was loving doing the podcast, so the honest answer to whether this was the one thing he wanted to wake up and do with laser focus was no.

He sold Milk Road to two private buyers, a completely different transaction from the Twitch deal.

Common mistakes

Running the check-in on your most frustrated day

Shaan explicitly warns to try not to check in on your most frustrated day. Founder conviction swings hard week to week, so a badly timed audit measures the current fire rather than the trajectory of the business.

Staying in a business you no longer believe in

If you do not believe, you will not take massive action, and without massive action you get no results, which reinforces the original belief that it was never going to work. The honest move is to sell the assets rather than grind out a self-fulfilling prophecy.

Treating the sale decision as a market question first

Founders jump straight to who might buy us and what are we worth. Shaan puts do you even want to sell as the first slide, because the buyer list and the negotiation posture both change depending on the answer.

Is it for you?

Best for

Founders several years in who are quietly wondering whether to keep going or exit

Not ideal for

Founders in year one, or anyone running the check on their most frustrated day

From the transcript

the first thing when it comes to selling your company is figure out do you even want to sell?

Shaan Puri · 05:00

Do I still believe this will be big if it works? Do I still believe I can do this? And do I still want to…

Shaan Puri · 05:30

Say, are these more true today, less true today, or are they the same as when I started?

Shaan Puri · 06:30

From the episode

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