Indy's Culture of Failing Successfully

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Ali Cudby is the founder of Your Iconic Brand. Ali Cudby is the founder of Your Iconic Brand.

Asking successful executives to share their failures can be somewhat disingenuous.

As a newcomer to Indianapolis, I was curious to attend the inX3 conference and see how Indiana’s tech luminaries chose to tell their stories of failure at the conference launch event, Fail Fest.

I expected thinly veiled self-promotion and affirmations of ultimate triumph.

I was pleasantly surprised to see thoughtful assessment and genuine introspection as business leaders shared accounts of their stumbles.

Kevin Bailey talked about going from "zero to sixty to zero" as the CEO of Slingshot SEO. When the company was at its pinnacle of success, instead of leaning into the moment, he was hit with a crisis of confidence. In worrying that he couldn't take the company forward, he brought in a more seasoned CEO. The decision to outsource was the wrong call for the company, sending it on a downward slide.

After being pressured to accept a candidate to lead a company in his Venture Capital portfolio, Don Aquilano failed to trust his judgment and voted with the pack. The company seemed like a sure thing, until the wrong leader stepped in. It was an expensive error that not only brought down the company; it nearly tanked the entire fund.

Jim Brown was so in love with his idea for Porchlight (which later became Haven), he failed to objectively ask the market what it wanted and needed. By ignoring the true needs of his customers, he ended up building a million-dollar service to solve a problem too few people actually had.

These leaders were willing to put their less-than-attractive stories out for public consumption. That's just one of the remarkable things about Fail Fest.

Here's the other: During Fail Fest, not one business leader talked about failures of technology. Nobody discussed a time when a good business failed from lack of funding.

Each person who took the podium at Fail Fest shared a story that revolved around failure from the interpersonal side of business.

They failed by not engaging customers, by mismanaging employees and even undermining themselves as leaders.

This combination of being open about failures and sharing them publicly says a lot about the culture of the tech community in Indy.

As Scott McCorkle noted, "culture isn't shaped by fiat at the CEO level." Words, pep talks and nifty murals extolling company values don't create culture. Rather, culture evolves through the actions leaders take. Culture is shaped by the decisions leaders makes when times are tough and how they celebrate when times are good.

Getting a look at the culture of the tech community was also interesting to experience as a newcomer to Indy - it's very different from the other places I've lived and worked.

I've always been in big cities where the underlying energy is competitive. Too often, leaders there engage like business is a zero-sum game - where one person's win means everyone else's loss.

The energy is tough.

It's kill-or-be-killed, and you'd better have your game-face on.

Indianapolis has a very different culture. From what I’ve seen, collaboration here is more prominent and competition is healthier - less cutthroat. Of course, there's competition to be successful, but the general sense is that one company's win is something people cheer together as a win for the tech sector, the city and the state.

What I saw at Fail Fest reflected this dynamic.

There's a lot to unpack here, and a deep dive into drivers of company culture could be its own series of articles.

Here are my takeaways from Fail Fest:

First, it's easy for start-ups to hyper focus on their tech. Based on what we learned at Fail Fest, tech isn't the what makes a company fail. The human factor is what ultimately makes the difference between winning or losing in the long term.

Second, culture is created with actions, not words. When being open and sharing (both successes and failures) is shown to be valued in companies, the greater community endorses a culture of being open and sharing. It's a virtuous cycle. Everyone wins by learning from previous mistakes, and events like Fail Fest are living, breathing embodiments of Indy’s tech culture.

Finally, Indy's culture of collaboration may or may not have been cultivated deliberately, but it's worth acknowledging how it differs from the ultra-competitive dynamic in larger tech centers. Indy has an opportunity to actively highlight its culture. By practicing the values reflected in Fail Fest, culture can become a feature of Indy's tech sector - and ultimately a differentiator.

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