It’s (always) a good day to die

3 values that drive entrepreneurial grit and savvy.

2 years ago, in desperate need of a big hairy goal to jumpstart a flatlined strategic planning session — I blurted out to my business partners that Cirklo would be a million dollar social enterprise in 5 years. A couple of months later that idealistic goal was buried under the harsh reality of being cash-strapped entrepreneurs, having to focus on the taxing grind of our daily hustle to make ends meet. Despite all odds, our team pushed forward and last week we forecasted reaching that milestone in 2018 — a year ahead of schedule.

While this accomplishment may sound like an entrepreneurial dream come true, it’s not. We had no idea how we were going to get there, neither did we know what it really takes to survive. We had to pivot and iterate our business model and management structures over and over again, which is part of the process and vital for any start up. However, that required a lot of tenacity, grit, patience, hope, sacrifices, honest feedback and blind trust amongst our team. That emotional/psychological rollercoaster is part of the daily hustle for a founding team as you scale your operation. It takes a lot of grit and savvy to navigate, if you are not prepared for this, don’t quit your corporate job just yet.

Take some time to reflect on the following values I believe are critical for a founding partner to possess.


For an entrepreneur, passion translates into a relentless pursuit of pushing the envelope in order to truly be the best (a.k.a. world-class) at whatever your team defines their value proposition will be. I know many people who possess remarkable expertise and/or battle-hardened insights into an industry. Based on this they begin playing with the idea of starting a business. The problem is the other side of the coin — how to translate that expertise so it inspires your team to want to become the best on a daily basis. My work is fueled by the desire to transcend from the individual to a collective good, a sense of greater purpose about why every detail counts in startup land. If you can embody those founding values at the most critical moments, that will drive everyone on the team forward when the shit hits the fan. (I’ve lived this at Cirklo & Fuckup Nights, countless times)

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I’ve also found this to be true in business, art, music, sports and just about everything worth doing in life.


This will keep you working until 3am and push you out of bed at 5am. The faster you build up your team to leverage your weaknesses, consolidate your cashflow and secure access to growth or emergency capital, the better. Until then be prepared to do like Sisyphus and roll your boulder uphill everyday. Don’t be the kid that asks for the puppy when it’s cute, fun and exciting only to deny responsibility when taking care of it becomes the exact opposite. I’ve seen passionate founders crumble like cookies when leadership and financial pressure surmount their charisma credits.

“The woods are lovely, dark and deep, but I have promises to keep, and miles to go before I sleep, and miles to go before I sleep.” — Robert Frost
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I consider this value like my daily cocktail of intuition, stubbornness, stupor and a dash of bravado. The relentless belief that despite sailing against the wind the conditions will change (a.k.a. market conditions, consumer mindset, technology adoption curve, etc.) If you work hard enough to influence those conditions, your team will succeed. If one day you wake up and don’t feel the magic — be vulnerable and share that with them— based out of their own convictions they can reignite your flame. If you plan to disrupt or better shape an existing business paradigm, you must be disciplined and methodological in your approach to business. Don’t treat entrepreneurship like it’s a right you deserve, treat it like a privilege. Let that shape your decisions and you will thrive through the daily hustle — despite the odds being against your favor.

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Conviction is what differentiates a hobby or side project from a business, it takes your team from being local talent to world class talent.


Ultimately, from my personal experience, when the pressure escalates and shit starts flying everywhere, an entrepreneur is tested in all three of these values. I can guarantee this will occur to every startup and it’s what matters the most. So when you think about taking the plunge into startup land, look deep into yourself and at the eyes of your partners and ask, “do we have what it takes to be in this for the long haul?”.

Fortunately for Cirklo, our accomplishment comes from the tireless and passionate effort of a collective of talented misfits that make up our team of 19 entrepreneurs. I am very grateful for their trust and for person they have helped me iterate into becoming over the past five years — thank you.

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