The Right Stuff

When I went to hear Sanjay Singhal’s fireside chat with Startup Grind Toronto’s Sharn Kandola I happened to be reading An Astronaut’s Guide to Life on Earth, by Chris Hadfield.

If Tom Wolfe re-wrote The Right Stuff today, Hadfield would be a lead character. Farm boy grows up to be a top test pilot, a space robotics expert, and the second non-American and non-Russian to command the International Space Station.

Singhal’s is his third startup. He is now a Canadian venture partner of 500 Startups. As he talked about his journey my ear was caught by the similarities of the career arcs of astronaut Hadfield and founder Singhal.

Both pursued multiple technical degrees at increasingly prestigious institutions.

Both discovered that these heady accomplishments are just table stakes to get an all-nothing-roll at the big game – to apply to the astronaut office or to pitch VCs. The odds of coming out on top in either pursuit are vanishingly small.

Both discovered that when you make it into the astronaut's office or raise that financing round -- that's when the real pressure starts. The stress amps up to levels never experienced before.
Many founders and astronauts discover that their marriages can’t stand the strain. Singhal was one of the unfortunate ones. Hadfield’s marriage survived.

Hadfield’s insights into the sources of that pressure really resonated with my startup experience.

The Startup Experience 

First of all, the work. Whether you’re a founder or an astronaut candidate you’re being evaluated and compared to everything. Moving forward depends on doing better than all your hyper-competitive peers. As Hadfield put it, “the demands are bottomless.” Oh yes.

Second, the dislocation. Hadfield described how he stepped onto the elevator at the Johnson Space Center for his first ride up to the Astronaut Office. When he got on he felt like a god... when he stepped off he felt like a gnat. He was back on the bottom rung, looking up at giants.

Close a financing round and you’re on top of the world. Then you have to deliver.

Hadfield talks about the steep learning curve where there are very few opportunities to stand out. If you can’t learn to get your self-affirmation internally, it’s brutal.  The same is true for the founders of startups clawing for traction.

Third, there’s the loneliness. Hadfield talks about how his previous life in the military had a communal rhythm, people lived in the same neighborhood, did things together. That doesn't happen in the astronaut's office. People are just too busy.

The first startup I did I was coming from a series of small companies so I wasn’t aware of the loneliness.  Between then and now I’ve worked for big companies and I find that I really miss the community that went with the big company. I expect the same is true when a founder comes from a faculty position.

Being a founder really isolates you.

If you have the opportunity to work with an incubator that has a lot of alum who are active advisors – take it. Spend every second you can spare with these folks. That’s the real value of the experience.

Dealing with failure. 

Dealing with failure is a huge part of both jobs. And it turns out that a career of steadily increasing achievement is poor preparation for the shock of failures that come later.

Singhal talked about how he jetted off to San Diego after completing his Cornell MBA to be a founder of a startup in Silicon Valley. It failed. Determined to succeed, Singhal jumped back on the horse. He helped to found another startup.

It too failed.

This one still stings. Singhal’s second startup brought mobile email to market two years before RIM. As Blackberry headed toward the stratosphere, Singhal’s company was dying and his marriage was imploding. He settled his divorce, got a job at Cisco and vowed to never do another startup.

Singhal said that he came to see these shattered dreams for what they were: valuable learning experiences.

He later recanted his vow of startup celibacy. Singhal’s third startup,, became a success.

Which is harder, founder or astronaut? Impossible to say. We’ve seen astronauts die in nasty, violent and unpleasant ways. Fuel tanks explode during ascent; heat shields fail during re-entry.

Founders don’t face this extreme level of mortal risk.

The risks for founders are more subtle.

It has to do with the ups and downs. Pretty much every startup survives multiple near-death experiences before it’s shut down, sold or emerges as a new star. Founders can become identified with their creations. This sort of mind meld is really dangerous given the insane ups and downs. It happens to many of us and is seldom acknowledged.

Founders who dodge this bullet are often nailed by a different challenge. They feel like they’re not permitted to acknowledge their doubts. And in time, these kinds of stresses can be quite lethal too.


That’s why it’s important to find advisors and investors who understand the crazy roller coaster that founders ride. In a startup get someone who can stand by you in those dark, uncertain days.