7 entrepreneurs share how to rethink risk and fail smarter

For an innovator, there’s no sure-fire way to avoid failure.

And why should there be?

Innovation is all about taking new approaches to familiar problems, processes, or ways of thinking.

This is what makes it both uncertain and full of possibilities for growth and progress. 

The question isn’t how to never fail. Instead, it’s a matter of how to take the right risks, bounce back, and reframe failure itself. 

Here, seven experienced entrepreneurs from the CIC community share their best advice on failing — or not. 

“Learn from the failure of others.”

— Floris Wolswijk, Founder & CEO, Queal

For CIC Rotterdam-based entrepreneur Floris Wolswijk, seeing that someone else unsuccessfully tried to introduce a product isn’t enough to rule out its viability. “Was it the wrong timing, too expensive, or something else?” he recommends asking. “There are thousands of examples online, and you can discover them for your specific industry without having to bear the costs yourself.”

In the case that none have gone before you, “fail small,” Wolswijk says. “If you run an advertising campaign, test it on a subset of your audience. Want to release a new product? First ship it to your most loyal customers. You can’t always test something on a small scale, and then you have to take a leap of faith. But before doing that, see what others have done and what you can do to test and fail on a small scale.”

“Sometimes when a company flops, another company is born.”

— Tiffanie Stanard, Founder & CEO, Stimulus

Award-winning entrepreneur and CIC Philadelphia member Tiffanie Stanard performs random market research in her everyday life to help assess if a new venture is worth pursuing. “When I’m at an event, I casually ask company leaders the same question. If I receive the same answers on their pain points, then the risk [of launching an idea or company to solve that problem] is worth taking,” she says.

As for overcoming failure, “you have to look at why a company failed, what processes you used or didn’t use, and your next idea will be there,” Stanard says. “The founders of Brex and Slack have discussed how their original ideas flopped. Stimulus became a company because of the pain points I experienced from my previous company when trying to close contracts with large companies.”

“The biggest failure for an entrepreneur is the failure to try something.”

— Stas Gayshan, Managing Director, CIC

For CIC’s Stas Gayshan, an entrepreneur himself, failure is a step within a longer process. “Failure is not the finale,” he says. “Failure is just the prelude to success.”

Moreover, a seeming flop can become one’s next discovery. “A scientist at 3M made a terrible glue once; it was so bad, it couldn’t permanently stick anything to anything. But, it turns out, glue that doesn’t stick is perfect for notes you want to temporarily put somewhere — and so Post-It Notes (and a massive industry) were born. Figuring out the difference between momentary setback and permanent failure is where true entrepreneurs show their genius, and where others miss the boat.

“For the entrepreneur, risk is measured differently than for a non-entrepreneur,” Gayshan says. “Risk for an entrepreneur is the risk of non-action. What will the world look like if we don’t try this? If this problem isn’t fixed? If the world stays the same? Considering the condition of the world, that’s the real risk.”

“Gratitude provides a lot of motivation to keep trying day after day.”

— Dr. Christi Barb, Owner and Accentologist, Adastra Speech

CIC Cambridge member Dr. Christi Barb keeps a note with her favorite quote about failure on her calendar:

There are only three ways to fail: 1) Never try. 2) Don’t improve. 3) Quit.

“On days when I’m feeling overwhelmed with the business side of running my business,” she says, “it’s a good reminder that when I take a break from that to do research and read about what I truly enjoy, it’s not wasting time. That’s improving myself and, ultimately, my business. It reminds me why I started my own business — to do exactly what I wanted to do — and I’m grateful.”

“Failure is simply feedback that something needs to be shifted and refined.”

– Ingrid Goldbloom Bloch, Career & Innovation Coach, Mosaic Careers

When it comes to assessing risk, CIC Boston member Ingrid Goldbloom Bloch suggests asking yourself the following questions:

  • How will I feel about myself if I don’t try?

  • What will it take for me to pass on this opportunity?

  • Who will I become if I take this opportunity?

  • How will I grow as a result of this opportunity, regardless of outcome?

  • How will this opportunity enhance what is important to me in my life?

  • Have I gathered enough information?

  • Have I tested my assumptions?

  • Do I have mentors and support?

  • What is my plan B if this doesn’t pan out as planned?

  • Can I tolerate being in a state of not knowing?

Once you’ve taken the plunge, you can contend with the results — even those you hadn’t hoped for — by using so-called failure as a learning tool. “By apply design thinking principles as a framework and cultivating a growth mindset as a muscle, failure ceases to exist,” she says. “Life, business, careers, and products are best viewed as part of an iterative process.”

“The risks worth taking are the ones I can’t not take.”

— Jung Starrett, Cofounder, SoulCo LLC

There’s always an element of unknown when you try something new. “Even with the most rigorous risk-benefit analysis, there’s no guarantee that I’ll make a perfect decision, because what I know is always less than what I don’t know,” says CIC Cambridge member Jung Starrett. Over the years she’s learned to follow the feeling of “when I know that the risk of stepping into the unknown pales in comparison to the risk of staying small in an old familiar place to avoid failure.”

Starrett has a process set up for herself to overcome risk aversion due to blame and shame. “When things flop, first I acknowledge how painful it is to face my own failure,” she says. “Second, I remember that failure is as much a part of life as success for everyone, not just me. This helps me to get over being hard on myself and feeling worthless. Then, I’m ready to ask myself, ‘What do I need to learn and carry forward?’”

“Never, ever, give up on trying.”

— Gustavo Rego, Founder, Blue Ape

In an article on Medium, CIC Rotterdam member Gustavo Rego applies the Swiss cheese model of accident causation to the question of why startups fail. According to this model, failure doesn’t result from a single action; rather it results when multiple contributing factors align. He identifies “latent conditions,” such as excessive optimism and misalignment between founders, and “active errors” in handling finances or market assessment, for example. Rego’s hope is that startups can use this methodology to examine their work proactively, not only analyze failure in hindsight.

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