I’ve been approached by a few people lately asking me a few questions about working in / applying for a job at a startup.

What should I look for? What should I consider?

Firstly, In my head a startup is one that has not raised a gazillion dollars at a Billion dollar valuation.

For this post, I’ll consider a startup that is cash-constrained, cannot hire the best people at market rates and has upside as it’s primary selling point.

As a founder who’s hired over 100 people in the last 30 months, and fired a few people, and as a founder who scrounges every day to find the best talent around, I’ve had a few ideas that crystallized lately into a thesis. And here it is.


Founder: The founder(s) set the culture, build the bedrock of the startup.

Are the founder(s) worth working for? Can she hustle? Can she fundraise? Is she approachable? Is she humble enough to accept mistake? Can she look beyond the obvious? Is she impressive? Do Investors and Customers trust her? Does she know the business well enough? Can you work with her? Has she attracted any other world class talent you’d be excited to work with? Does she have social cache with people you admire?

The Vision: The vision sets the long term trajectory of the startup.

Is the vision hairy enough? Does it resonate with you? Is it too utopian? Is it too simplistic? Is the Vision being confused with the Mission? Has the Vision morphed over time? How rigid are they about the Vision? Can you spend the next 10 years working towards this Vision?

And finally,,,

The Market: The market is the Go-To strategy that establishes the basis of the business that will feed the company revenue.

Is the Market realistic? How soon does the company start making money? Will this market serve the company long enough to be a Billion Dollar company someday? Is the market competitive, crowded? Can this startup differentiate itself from the crowd? What are the levers for growth? Can this company pivot to another market to fulfill its vision?

Now here’s the real kicker… Most startups try to optimize for all 3 in the early stages.

But as they grow, they compromise by looking for either 2 out of 3 or even 1 out of 3 to fill the ranks.

This is a mistake, In my Opinion.

Are you here for the Founder? That’s going to cause friction when the Market demands outstrip the Founder’s niceness.
Are you here for the Market? That’s going to make you disillusioned if the startup outgrows the Market and pivots or if the Founder changes gears.
Are you here for the Vision? What if the Market isn’t big enough? Or the Founder leaves? Will you carry the Vision?

1–10 team size: As the company grows from 1–10 team members, people come on board either for the Founder or the Vision. The Market is not set yet and the Founder is charismatic enough to show something where there is nothing,

10–50 team size: As the team grows from 10–50, people come on board for the Market or the Founder. The Vision is in the background, but the startup has found some Product-Market fit, the wheels are turning and the Founder is building the right culture and the right people are jumping on.

50+ team size: It is at this point that you need to understand the real long term motivations of your crew. If you can afford Market salary, stop reading now. If you cannot, and you’re still selling your prospective team member on the opportunity, then it’s both your responsibility and duty to clarify intents: Do you want to solve this problem? Do you want to attack this Market? Are you happy in your role? Is the culture open enough for you to find your peace? Can you see yourself working here for the foreseeable future?

Just 1 of 3 is not enough.



One clap, two clap, three clap, forty?

By clapping more or less, you can signal to us which stories really stand out.