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Risk-Reward vs. Success-Failure and Others Lessons from a Serial Entrepreneur

Serial entrepreneur Gregg Oldring recently wrote a post about his recent startup that failed – “Afraid of failing at a startup? Let me tell you what it feels like.” Naturally, I wanted to dive into the title given my past.

There were a couple lines I really enjoyed. Sharing those here, and highlighting my own experience.
  • “When I frame the analysis as risk-reward instead of success-failure, we did well.” Maybe because I failed before with Body Boss, but this was incredibly resonating. Like Gregg highlighted, there was so much gained from the experience that isolating the outcome based on commercial success would be vain. In the end, we threw out risk to attempt something special. The reward beyond was worth it.
  • “One of the things that I hate about being an entrepreneur is that sharing the uncertainties I have about my business usually carries with it negative consequences that outweigh the benefit of transparency. When someone asks, ‘How’s business?’ the answer can seldom be, ‘It doesn’t look like it’s going to be sustainable.’” Geez, this ate at me towards the end of Body Boss. I felt like a fraud when I spoke to others – prospects, yes, but especially with my personal connections (friends and family). The weight of faking a smile was heavy. So heavy, in fact, that I avoided any discussion about the venture as much as possible.
  • “I’m not embarrassed or ashamed that Inkdit didn’t thrive. My friends, family and community haven’t made me feel that way. In fact, they’ve done quite the opposite. I’ve been reminded that I have many people who support me.” As the dust settled from shutting down Body Boss, friends and family came from everywhere pledging support. It was humbling. In many ways, too, I was proud. Many applauded our courage and how we built something from nothing.
Gregg’s experience from failure sounds a lot like mine. As I read the comments to his article, I’m reminded of the power of sharing unsuccessful stories and being vulnerable. Confidence in what we’ve achieved and where we’re heading gives us power to go again. Sharing our stories gives others the confidence and support they, too, can go for greatness.

By the way, you can read more about my experience from my book Postmortem of a Failed Startup: Lessons for Success. It’s a quick read so you can learn, apply, and go (e-book and paperback available).

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