Inside Out: Is failure in startups a privilege reserved for the few?

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To no one’s surprise, Katie and I are building a company. It’s the thing that consumes most of our day to day lives. We talk and think about it near incessantly. Entrepreneurship so far has been exactly what I thought it would be and nothing like I thought it would be all at once. I don’t want to attempt to distill the last few months into any lessons because we have a long way to go - this is really just the beginning. That said, oftentimes our goal with this little corner of the web is to speak candidly about entrepreneurship and what it means to found a venture capital backed startup. Some days, we’re hyper focused on the hour by hour grind where we’re heads down at work trying to push out content, product and experiments. Then other days, we’ll find ourselves on Slack late at night or on a weekend morning reflecting on some of the big-picture questions that have come out of entrepreneurship and startup life. The latter was one of those weekends where an article on the internet made us pause. 

If you don’t read Man Repeller, you should start. It’s not just a fashion blog, I promise. It’s a blog for killer cultural commentary and more generally those “yes, I totally relate to/have thought that” moments. Anyway, I’ve digressed and my plug for Man Repeller is done. Back to the topic at hand. 

This weekend, I read a piece on there about the glamorization of making mistakes in the startup community. I sent it to Katie last night, and it sparked a pretty interesting Slack conversation and internal debate between us to which we have no real conclusion. There’s a lot to unpack in this one piece and it’s a really nuanced conversation that I want to write subsequent pieces on, but at its core, the startup world has glamorized the idea of moving fast and breaking things, making mistakes, bouncing back and taking big risks for big rewards.

The part of the article that hit home for me came here: 

“While the startup world may be designed to embrace and learn from failure, it’s a world that is welcoming to only certain types of folks. Hustle culture is just American capitalism as it has always been. It’s not an absence of fear that helps some bounce back from failure, it’s all the small, untold ways other people and systems have helped some rise to the top.”

It’s a tricky thing because Katie and I like to think that we’re building this company on our own terms, but we’re also going along with a “playbook” of sorts. There’s a way that startups, specifically venture capital backed startups, go out and build a team, gain customers and grow. And out of what was once a Silicon Valley-only archetype has emerged an entire genre of work designed to help founders and early stage employees everywhere navigate startup life. Books like High Growth Handbook, The Hard Thing about Hard Things and Zero to One become anchor pieces that house the startup vocabulary, lingo and milestones. 

And fundamental to this startup roadmap is a culture that has glamorized making mistakes, failing and getting back up again. And I get it. There are certain industries or problems where no great innovation came without some equally great mistakes. No massive change happens passively. But inherent to this way of thinking is the idea that failure is not catastrophic - you can just bounce back. The truth is though that for a lot of people, failure is catastrophic. Putting everything on the line isn’t an option. 

Not everyone has access to venture capital funding. Not everyone has the pedigree and education that allow them to have fallback options. Not everyone looks the part of what’s ‘acceptable’ as a founder. Yes, Katie and I are two first-time female founders, but we also carry degrees from great colleges, graduated from HBS together and come from incredibly supportive families who are letting us live out this dream. 

I have no real answers and this is not meant to be a rant against Silicon Valley or tech startup culture, but rather broad commentary on access, privilege and what it means in the startup community to tell people that failure is okay.

Failure is okay. We should not punish people for making mistakes - they are learning opportunities. But we have to think about who is allowed to fail in this system. What does it mean to have the luxury to fail over and over again? What types of people are allowed to make mistakes? Are these tried and true paradigms really just reinforcing mechanisms that keep some people in the system and some people out? 

So it’s something that Katie and I have to constantly keep in mind, and these are the questions we must return to regularly. Failure is important, but failure is also a privilege. Who are we making money for? Who is included in what we’re building and who is left behind? What role does privilege play allowing us to live out our dreams and what does that mean we owe back to our team and to society going forward?