Through A Cracked Camera Glass: Conversations About Failure

A crowd of about 50 people listened to three successful entrepreneurs dish out anecdotes, and advice, on how to handle failure and achieve success.

Tech Fail 2David Kadavy, serial entrepreneur and author of Design for Hackers: Reverse Engineering Beauty, a book which premiered at number 18 on Book list in August 2011, got the crowd chuckling from the start. “Where’s the fire?” he joked. Kadavy and Craig Ulliott, VP of Product and CTO at Belly were the featured speakers at the event. They were in the BellyCard offices of 600 West Chicago Avenue. Hosting the talk was Mana Ionescu, president of the digital marketing company, Lightspan Digital.

Both speakers offered up counsel for entrepreneurs, often politely disagreeing with each other, while Ionescu occasionally threw in a bit of her expert advice. Expletives were thrown around to the comfortable crowd, sipping wine and lounging on couches and at high tables. Both speakers were chosen for their differing backgrounds and opinions, according to Lisa Russell, co-founder of Ms. Tech, which was evident throughout the chat. Kadavy confessed his love of passion rather than money, while Ulliott unabashedly chimed his fondness for profit. Here are some highlights from the event.


While the speakers agreed that failure is just part of an entrepreneurs story, Ulliott insisted on failing quickly.

“You want to capitalize on your time,” Ulliott said. “If you have an idea, you want to try it and fail as quickly as possible, because if you drag out an idea that isn’t going anywhere, you’re basically wasting time, probably burning relationships and making yourself look bad.”

Ulliott also spoke about failing versus working for a company.

“I’d rather fail and keep failing than sit in a cubicle and build someone else’s dream. And it’s hard, but I’d rather fight. You’ve got to enjoy working 100 hours a week. There has to be that drive in you.”

Kadavy added that he sees failure as a learning experience. He said he “messed around” for three years until he found an endeavor that stuck: his book. He said he chooses to take failed risks with little investment until he feels like the venture will succeed.


Kadavy and Ulliott began to debate when it came time to talk about success and emotions.

“If you can’t make measured risks, then you’re probably going to fold and fail,” Ulliott began. “You need to be very objective and cool. Running a company is not an experience that should be emotional. It should be very calculated.” Kadavy then chuckled, working off Ulliott’s advice.

“For me, ideas and whether or not to pursue them is a very personal thing,” Kadavy said. “This is what I’m going to spend my days doing. How do I feel about spending my time doing this? But at the same time, you have to pay attention to the market a little bit.”


Ulliott decided to offer advice for creating an initial business model, while Kadavy gave a quick anecdote.

“People underestimate the importance of a financial model, and it can be very simple,” Ulliott said. “It can be just a Google doc spread sheet… and that’s then your business. Find out what the cash needs are going to be and stay the [expletive] to that plan. Passion is not going to get you where you need to go if you’re not sticking to that plan.”

Ionescu nodded her agreement, adding a quick tip to the chat.

“I think a lot of entrepreneurs don’t know what their books look like, and that’s just criminal. Ionescu warned. “If I wake you up in the middle of the night, you should be able to tell me what the bottom line is and where you project it to be; otherwise, you’re running in the dark.”

However, Kadavy said he has had a different approach throughout his years of serial entrepreneurship. His recommendation was to pursue multiple ventures before finding the right idea.

“For the most part, as an individual, I’ve just been going by the seat of my pants,” Kadavy said. “I just sort of have this internal calculator. Some people should maybe pursue multiple ideas, and it can be surprising how explosive something could be if you hit the right thing.”


“The one word I didn’t hear either of you mention is pivoting, but it’s a very common word,” Ionescu prodded. “If you walk into 1871, you walk through the room and you hear and you hear it a hundred times.”

Kadavy responded by calling it “Oh, this didn’t work,” receiving a laugh from the crowd, as Ulliott chortled and said it was quite concerning that it had a name. ‘Pivoting’ is attractive to venture-backed companies because venture capitalists get a second chance with their money, according to Ulliott.

“Pivoting is a popularized term because it makes a ton of sense for the guys with the money in,” Ulliott said. “It doesn’t necessarily make sense for the entrepreneurs unless you have significant assets that you can pivot into something else. That one business shouldn’t be a vehicle for you to keep trying.”

Kadavy agreed with Ulliott’s points before qualifying them.

“But if you really are ahead of the curve in some way,” Kadavy said, “you actually really have a vision or something you really see differently than others, sometimes you’ve got to persevere.”

The discussion ended with a few wise words from the entrepreneurs, encouraging the audience to learn from Britney Spears’ mistakes and pursue their passions. “Why did Britney Spears go nuts?” Kadavy prompted. “Duh! She wasn’t pursuing things that were fulfilling things to her, as a human being.” ❒

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