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Against the Odds

“The point of roller coasters isn’t to be better at riding roller coasters; it’s to learn how not to board the roller coaster at all. Coney Island’s Cyclone is best appreciated from the ground. Resilience isn’t the goal; it’s the path. The goal is the equanimity of a warrior.” – Jerry Colonna 

“The failing process is pressure-packed and painful,” notes Tom Eisenman in this podcast conversation with Jerry. In his new book, Why Startups Fail: A New Roadmap for Entrepreneurial Success, Tom dives into the various patterns that contribute to startup failures in his research. In a nutshell, it’s more than just the jockey (the founders) or the horse (the idea or product), and has to do with a variety of conditions both on and off the racetrack. While it helps one’s chance for success to know the patterns that lead to failure, the way one walks the entrepreneurial path helps one weather the existential “happening” that is ‘starting, building, and scaling a company.’

The pressure and the pain Tom references come from the relationships and decisions a leader faces when they are not heading to the winner’s circle. Navigating the decisions and the process of shutting down a company bring up a mix of intense feelings. These feelings are tied to the core ways we as humans experience our sense of self in the world through our work. While moving through a non-successful business situation, an entrepreneur will be faced with many choices, thoughts, and questions including, but not limited to: 

  • How has the leader’s identity merged with the company? How might their image as an entrepreneur certainly be faltering in the face of failure? 
  • What is the magnitude of the weight of responsibility the leaders feel for the employees of the company if there is no longer a company?
  • What will the investors think? 
  • How does a leader decide to back out of the race? Who can they turn to? How can they not feel so alone in this situation? 
  • What might other non-work relationships have left in them? If relationships with a spouse or friends have been stretched thin, what support does a leader have there? Are these people available to be a support?
  • What’s the right thing to do? Close or sell the company?
  • When there is no company anymore, when does the depression set in? 

The pressure of failure compounded with questions like these can make even an equanimous mind waver a bit. For the leaders and founders who don’t walk this entrepreneurial path with their inner resiliency, failing can be soul-crushing. 

In our almost 150 podcast conversations, failure is a theme that comes up often. I think of these hearts who’ve had poignant conversations with us about how they faced failure: Avni Patel Thompson, Rand Fishkin, Ben Rubin, and Ben Saunders. Moreover, what we learn is that in the ventures we set out to do: Failure is normal. Perhaps, even more so, we learn that a company that fails doesn’t mean you are a failure.

What is an entrepreneur to do when we have a drive towards a vision we feel is possible? Knowing that the stakes are high, how do we withstand the ride? As Kenny Rogers sings in his ballad, The Gambler,  “If you’re gonna play the game, boy | You gotta learn to play it right.” Or, as Jerry writes in his book, Reboot: Leadership and the Art of Growing Up, “True grit is more than the capacity to grin and bear it. To understand true grit, we need to understand false grit.” 

“False grit is brittle. It’s the sense we are nothing if we can’t take a punch. In fact, we define “taking a punch” as the ability to to feel pain when we are punched. False grit is dangerous. It feeds a stubbornness that, in turn, can feed delusion. We mistake the tendency to delude ourselves that our relationship will improve, our companies will succeed, if only we double down on our old patterns, grip the steering wheel until our knuckles whiten, and bear down. Stubbornness is not the hallmark of the warrior. […] Leaders who persist out of stubbornness, believing themselves to be gritty, are at best delusional and, at worst, reckless.” 

False grit awakens our inner critics, the inner voice whose messages tell us that we should ‘persist to prove we aren’t as worthy’ as that critic claims. But there’s more: the second implicit message is that “if we feel like shit after being punched in the face, it must mean that we are shit.” “The only way to escape the grip of false grit is to recognize its falsity,” he writes. 

“True grit is kind. True grit is persistent. True grit persists not in holding on to false beliefs against all evidence but in believing in one’s inherent lovability and worthiness. True grit is the leader believing in the team’s purpose, it’s capacity to overcome obstacles, and the relevancy of the cause. True grit acknowledges the potential of failure, embraces the fear of disappointment, and rallies the team to reach and try, regardless of the potential loss. […] True grit, the capacity to stick with something to the end, stems from knowing oneself well enough to be able to forgive oneself. To have inquired deeply and steadily enough to find the deep sense of purpose that is beyond a personal mission statement. In that knowing of oneself, one is then able to stand as a single warrior amid a community of brokenhearted fellow leaders.”

Where might you be exercising false grit? What are you facing, now, that calls for true grit? 

How can we stand against the odds? From a high-level view, there are patterns that we see in our work as coaches that might help you navigate the world as an entrepreneur. These questions below might pose as useful journal prompts or points of departure to deeper inquiry for yourself: 

  • Who are you without your company? How do you separate yourself from your company? 
  • What do you know about yourself? Who are you on your best day? How are you when you’re at your worst? What are your non-negotiable needs? 
  • What happens when you’re under stress? How do you handle unknown unknowns? How do you work with your shadow and blindspots?
  • When there’s conflict happening, and hard conversations to be had, what is your default setting? How do you like to give and receive feedback?
  • What did your family teach you about work and money? What parts of that are you bringing into this endeavor? 
  • What do you know about your values? What is your ethic towards yourself, others and the world? 
  • What drives you to show up everyday? What’s the outcome you’d see happen? What happens if you miss the mark? 
  • What fears might be driving this endeavor for you? 
  • Who can you turn to that you can trust? What additional support might you need? 
  • What agreements and commitments will you make to yourself, your partner, your family and your friends and other important relationships in your life? 
  • What are your boundaries around your needs? 
  • How do you proactively take time away from your work? How do you recharge and nourish yourself? How do you ensure this is a priority?
  • What do you know about what makes you feel safe? About what gives you a sense of belonging? And what makes you feel loved? What inside of you tells you that you are inherently loveable?


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