Courageous Risks


How Random Acts of Entrepreneurship may be hurting your business

My clients are my heroes because of their passion and drive to bring their vision to life. I appreciate the risks they take to “launch” their big ideas and I often reflect back on lessons learned along the way.

One big lesson learned is to focus on having something to launch early and often. From experience, once a season works well. Pushing yourself to launch something every season creates a sense of urgency and focus to prioritize, gain momentum, track performance, and measure results.  Your launch could be as simple as sharing your pitch deck with a few trusted advisors or as big as launching your business.

Neil Armstrong said, “There can be no great accomplishment without risk “. As the first man to walk on the moon, Neil Armstrong was one of my childhood heroes. He opened my eyes to see risk as something to embrace as a key part of the journey; not to be feared as a barrier to success.

I love how this infographic from Paul Graham’s essay “How to start a startup” maps the journey and adventure of bringing your vision to life.


The big take-away from this infographic (which by the way is one of my favorite infographics of all time) is that there are little wins to be had at each milestone along the road to success.  These milestones provide a great guide to planning your seasonal launches. These wins are a result of taking courageous risks, often coming with few bumps, bruises, and “lessons learned”.

However, there is a BIG difference between reckless risks and courageous risks, at least as they relate to starting a new business.  Reckless risks come from Random Acts of Entrepreneurship. These are ad hoc, well-intentioned, not-completely-thought-out, fingers-crossed, I-hope-this-works-decisions made because “it feels right for my business”. Whereas courageous risks are a part of following a plan and logical steps along the road to success. Because, as we all know, there is no guarantee of success, no matter how well you envision your path forward.

Depending on the T-shirt size of your big idea (i.e. x-small, small, medium, large, extra-large) the steps along the road to success could take days, weeks, months or years. The key here is the word “Steps” vs. “Random Acts of Entrepreneurship”, though we all get excited and do these!

Common Random Acts of Entrepreneurship include entering into business deals with friends without a clearly defined statement of work because they are our “friends”, giving away our services and products for greatly reduced prices to “get our foot in the door”, or how about working nights and weekends at our family’s expense because we are “hustling” to succeed.

Based on both my personal and client experience, I find that the reckless risks of Random Acts of Entrepreneurship either cause sloppy mistakes resulting in waste and embarrassment or high-stakes mistakes that impact the viability of the business, your health or relationships. Rarely, if ever, do these Random Acts of Entrepreneurship with their inherent reckless risks work out in the long run. When you take courageous risks as a part of following the steps of your startup journey, the mistakes that occur along the way can be leveraged into valuable learning experiences for the future and help build key skills required for the business to succeed.

We have all participated in Random Acts of Entrepreneurship and taken these reckless risks. When the inevitable sloppy or high stake mistake happens, we dust ourselves off and keep moving forward. Learning the difference between courageous risks that result from working a plan and reckless risks that are inherent in "Random Acts of Entrepreneurship" will help you move forward along your startup journey.

My tip for your 2017 seasonal launch strategy is to take a minute to reflect on your lessons learned from winter and spring. Think back to what worked and what didn’t in terms of momentum, performance, and results. Take the momentum and hard earned lessons learned to see what milestones to aim for with your summer and fall launches this year.  Map out a well-paced plan with plenty of opportunity to pick up small wins in 2017. Rally your support team while making sure everyone has clearly defined roles and expectations for success, and get started! 

Note to self: Just make sure to have a plan and direction, and avoid indulging in Random Acts of Entrepreneurship.

You got this! 

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