Questions to Ask Before You Join a Startup

From my nasty 2002/.COM era experience with a startup would have said the 3 questions were:

1.) Do you like Kool-Aid, psychotic office politics & megalomania? 2.) Can you handle bizarre CXO behavior & feature requests designed for investors and not customers? 3.) Are you financially prepare to be underpaid for your skills AND have your paycheck 'not show up' one day when it tanks?

I hope to hell things have improved since then. I'm personally not willing to take the chance though.

This piece wants to sell us the startup ethos. Be young, work 14 hours a day and get paid 40 kEUR. But we are in Lisbon and will throw in a surfing pass for Ericeira beach!

Other people recommend asking things like the amount of runway left, who the CFO is and how successful he was in past rounds of fundraising, if the founder is fresh out of academia and doing their first company, nevermind the location and the cost of real estate. And the usual things, like the immediate supervisor, company culture and benefits.

"Startups are for grownups. [...] Grownups are willing to give the next five years of life to the pursuits of the startup — the people. Blindly."

Nothing to see here except more patronization. Move along.

This is actually more an aspiration than a reality of startup life:

" Grownups do the difficult thing when it’s the right thing to do, with composure. This means giving peers and employees critical feedback. It means saying the unpopular things about your startup’s product or service offering and assuming responsibility for failures. It means being really honest about the strengths and weaknesses in the management team. This strength comes from surviving and overcoming difficult circumstances. Grownups can do this over and over without losing credibility or support of the team."

But I agree that I tend to find more of this kind of honesty in small startups than in big companies, and for this reason I prefer to work with startups.