The 1st Step For Creating A High-Impact Entrepreneurial Ecosystem

This is the first post of a 7 part series diving into the pillars of what creates high impact entrepreneurial ecosystems. After you read this post, check out the next one on the 2nd pillar. 

[tweetthis]Read The 1st Step For Creating High-Impact Entrepreneurial Ecosystems!

ec·o·sys·tem // [  ēkōˌsistəm / ]

noun: ecosystem; plural noun: ecosystems;

Add heading (2)

  1. a biological community of interacting organisms & their physical environment.
  2. (in general use) a complex network or interconnected system.
    • ex: “Silicon Valley’s entrepreneurial ecosystem”

Entrepreneurial ecosystems are something I’m incredibly passionate about. And yet, I’m still trying to figure out how to exactly define them. You can look at formal definitions from Wikipedia, Harvard Business Review, Kauffman Foundation or Forbes. Or look to leaders like Brad Feld who explored them in his book or Daniel Isenberg who wrote a series searching for a definition. But here’s my take – it’s kinetic connections that intertwine intentionally and serendipitously to create an environment that sets entrepreneurs up for success to flourish. It’s a type of magical entropy that can’t quite be calculated by an equation, that spans across space it encompasses and the types of players who are a part of it.

Entrepreneurial ecosystems = kinetic connections that intertwine intentionally & serendipitously to create an environment that setting up all for success to flourish.

An ecosystem can range from a co-working space to a continent and includes people, organizations, policies, government, investors, entrepreneurs, mentors, accelerators, non-profits financial trends, and beyond. Regardless, it’s this surging force forging creative collaborations, kinetic connections, and collective impact that creates exponential possibilities for entrepreneurs to realize their visions. Something I like to call “impactful serendipity”. To take it back to The Lion King, it’s a circle of life in which different relationships are interdependent on one another and their environment to survive and thrive. The organisms part of the ecosystem is just as important as the environment in which the organisms are existing for an ecosystem to be born. The larger space gets (from a coworking space to a continent) the more actors are needed and the more components of the environment exist as well as the length of time to create a flourishing state lengthens.

[tweetthis]”Don’t let the noise of others’ opinions drown out your inner voice. Have the courage to follow your heart & intuition.” – Steve Jobs[/tweetthis]

Accelerators and incubators are great examples of intentional creations of flourishing ecosystems by bringing together entrepreneurs in an environment for a fixed time period that set them up for success with the tools they need and the people they need to get to the next stage of their growth. By throwing them at a wall as fast as possible by challenging their conceptions of possibility, these are houses of a power of innovation and rapid evolution of startups who participate. However, one of the biggest criticisms of these programs is the fact that they have a huge impact, but this is just the sprint in what is the marathon of creating a successful startup (which on average is a 10 year journey from concept to exit – whether that be a failure, acquisition or otherwise).

By throwing entrepreneurs at a wall as fast as possible & challenging their conceptions of possibility, accelerators are force fields of innovation.

Which is why I’m diving into 5 entrepreneurial ecosystems over the next 5 years on 5 different continents and derive on-the-ground insights from accelerators, communities, networks, organizations and beyond to unlock human-centric trends, ideas, industries, people, mentors, investors, startups, and game-changing x-factors. To explore these drivers in an ecosystem that takes different forms in different places, but are unleashing their collective power to move the needle for entrepreneurs around the world. I’m beginning this entrepreneurial ecosystem writing series by exploring different frameworks and theories behind global entrepreneurial ecosystems that can apply from the highest macro level to the micro space in which you work. I’ll then dive into different methods of exploring on the ground insights from the different places I’ll be working over the next 5 years, starting in Puerto Rico. (I’m heading to Australia, South Africa, Scotland, Brazil, and Asia on the horizon..if you have any badass connections to people or organizations in these regions, I’d be forever grateful...reach out to me via email.)

The 1st pillar of the 6 pillars necessary to create high-impact entrepreneurial ecosystems: creating a risk-taking culture.

This kick off article explores entrepreneurial ecosystems based on a framework by Kauffman Fellow who did research of Stanford entrepreneurial ecosystem that breaks down the key components of an entrepreneurial ecosystem into 6 foundational pillars that are imperative for ecosystems to exist and for high-impact interactions. Looking forward to your feedback, thoughts, comments and beyond! Here are the 6 pillars of flourishing entrepreneurial ecosystems and how I’ve experienced them throughout my entrepreneurial journey as well as over the last 3 months in Puerto Rico.

Drumroll, please…

[tweetthis]Create a risk-taking culture fueled by a spirit of experimentation, fearlessness in the wake of failure, open attitude & a pirate’y disregard for the status quo.[/tweetthis]

Create A Risk Taking Culture &

How To Do It

As I mentioned, the launch of this series explores the first pillar of the 6 pillars that create badass entrepreneurial ecosystems. And the first pillar: creating a risk-taking culture. A culture in which it is okay to fail and that is fueled by a spirit of experimentation, an open attitude, learner’s mindset, and a pirate’y disregard for the status quo. But how do we create this? I believe it comes from our collective actions as individuals, teams, and communities. Here are some experts and my take on how to create a risk-taking culture.

#1. Lessons From Mentors.

Overcoming comfort is like overcoming gravity. These are the wise words of Singularity VP and legendary Heretic, Pascal Finette, in an article on how comfort is an entrepreneur’s number one enemy. One of the first fundamentals of a thriving entrepreneurial ecosystem is one that is permeated with a risk-taking culture. Proof of this being that the world’s most potent entrepreneurial ecosystem – Silicon Valley – has a status quo belief that failure is a badge of honor. One that sees failure as important lessons learned instead of an experience to fear. As Parallel 18 mentor Beto Pallares says, “An aversion to failure can be the greatest enemy of a flourishing entrepreneurial ecosystem. Communities no matter how small need to implement a culture of acceptance in the wake of failure.

Overcoming comfort is like overcoming gravity.” – Pascal Finette, Singularity University & author of

#2. Lessons From Fellow Entrepreneurs.

Indeed, my on-the-ground research interviewing 70+ mentors and entrepreneurs in Puerto Rico proved just this. In every interview, I love to ask my burning question that I hope unlocks insight to fellow entrepreneurs around the world: What lessons have you learned that have been most impactful on your entrepreneurial journey or advice you have to share w/ fellow entrepreneurs? Roughly 75% shared either a personal story of failure or advice to find comfort in failure. Failing is to entrepreneurial journeys as growing old is to living. It’s inevitable. It comes with the territory. Seek advice and kinship with fellow entrepreneurs and opt for candid conversations on failing and supporting one another.

Failing is to entrepreneurial journeys as growing old is to living.  It’s inevitable but glorious.

#3. Find Your Community Of Fellow Failures.

A global community does just that – F*ck Up Nights exists to celebrate failure by sharing it with community members. Imagine a TED talk + AA meeting combined into one, where fellows can tell their stories and find the kindred community to not only support them but make sure they know they are not alone in this experience. These events happen in over 80 countries and 252 cities, so find yours near you and meet the fellowship of failures who are debunking the status quo of failure as we know it.

[tweetthis]” Take away all the shame from failure & leave the lessons.” – @BetoPallares, Parallel 18 Mentor[/tweetthis]

#4. See Failure As = Learning Minus Shame.

My former colleague and CEO at Unreasonable is a huge advocate for trying to change the way we experience failure from a shameful norm to a learning experience. To share a personal experience, one of my biggest failures happened in a global spotlight running operations for an inaugural Unreasonable program. This was the most important and meaningful job of my life and something I was extremely passionate about; yet no matter how much I cared and how hard I was working, I did not set up myself up for success and lacked the experience and maturity to operate and execute successfully in the midst of unexpected curve balls, fast paced work and in a situation I had never experienced. We were working 90 hour weeks pulling off a program that hadn’t been done before with scrappy startup resources (a.ka. no money). Despite these factors and unique circumstances, there’s no excuse for my performance (or lack there of at this program). This program ended up being a smashing success for everyone involved and the mistakes I made and balls I dropped didn’t negatively affect the program at large (however a few people were forgotten at the airport and some flights didn’t get booked until last minute of which I’m truly humbly sorry…), my performance and the expectations of my personal results were absolutely not met. I was ashamed, drained, exhausted, shocked, embarrassed, guilt-ridden and absolutely sure I was going to be fired. I was devastated and heartbroken when I arrived at my debrief interview with my boss and CEO of Unreasonable, Daniel Epstein. As opposed to firing me and confirming my then conception of failure as horrible, fearful and shameful – though we both acknowledged that in fact –I did fail and failed hard – Daniel celebrated the lessons learned from my failure and the investment made in this experience by sharing with me a great story. A story that flipped my perspective of failure on its head and has been close to my heart ever since.

A young executive is at IBM is promoted and makes several huge mistakes on the first day that loses the company millions of dollars, instigates havoc from stakeholders, investors, and board members, and gets smeared across headlines in the media publicly shaming his incompetence. The CEO, Tom Watson Jr., calls him into his office and the executive is sure he knows what is about to happen.

He says to the CEO: “I suppose after that set of mistakes you will want to fire me.”

His answer: “Fire you? Not at all, young man, we have just spent a couple of million dollars educating you.”

Daniel’s leadership in this situation spoke more to me and empowered me more than I have ever been – truly backing up his belief in seeing the positivity of failure. More leaders need to do the same.

Employee: ” I suppose after the mistakes that cost us millions you’ll want to fire me. ”

Boss:Fire you? Not at all, we have just spent a million dollars educating you. ”

#5. Self-Love > Shame.

Take away all the shame from failure, leave the lessons. Nearly always easier said than done. On my days in which I fall flat on my face and get the wind knocked out of me, I remember this story and find comfort in it. I can’t say failure ever gets comfortable for me – I’ve failed, again and again, sometimes even doing the same thing that I thought I learned the first time. I don’t consider myself someone who isn’t insightful enough to evolve given insights and lessons, but there are so many ways to fail and mistakes to be made doing one thing that often times we have an ongoing list of what not to do despite the expectation that the next time we should have learned exactly what to do. My advice? Be kind to yourself. No matter what and no matter how hard. A great mentor of mine once told me that shame and guilt are useless emotions. I just read an article on how worry is likewise in this category of useless feelings.They drive no positive value to yourself or your future. So take a deep breath, channel the song from Frozen – let it go, and have faith in the documented entrepreneur lessons + research that again and again say, failure is a prerequisite for success.

Take a page from Frozen: let it go. Guilt, worry & shame are useless emotions.

#6. Participate In The Bigger Picture.

Beyond creating a personal relationship that embraces failure, how do we create this in our company? Communities? Ecosystems at large? The first step is lead by doing, especially if you are an influencer or an executive at your startup. Celebrate failures of your employees and don’t punish them. Actions speak louder than words and when frustrating f*ck ups happen, remember that failure is a fundamental part of creating a risk taking culture and flourishing ecosystem, not to mention believe in the research and lessons from others that these failures (no matter how frustrating when they cost you valuable time, resources or reputation) are instrumental lessons and part of the physics that control the trajectory of the entrepreneurial journey toward success. Empathy builds empires, so treat your employees with empathy and if you build it, they will come. Thank you, Field of Dreams (your wisdom is the gift that keeps on giving ;- ) )

[tweetthis]Lead by doing.[/tweetthis] 

#7. Encourage Your Company’s Risk-Taking Culture.

And encouraging this failure is one of the 4 ways you encourage a risk taking culture at your company, according to Founding Editorial Director of Upworthy, Sara Critchfield who shares 4 ways to push your team to take risks and experiment in her Harvard Business Review article. It’s critical to go from a “best practices” mentality to a dynamic experimental mentality. Here’s how.

How to create an experimental mentality across your team:

  1. Truly Normalize Failure With Actions + Words. Sara says, “The first thing the team needed to hear me say was, ‘A 95% fail rate means you are doing a great job! No, not just a great job — a fantastic job!’.
  2. Individual Accountability For Experiments. It’s useless to separate the person with an idea and the person who tests the idea. Honor humanity in that experiential learning is how humans are hardwired to learn, iterate, innovate and ultimately evolve.
  3. Tests and Data For New Tests. Tests and data should be used to create a new test, not to generate best practices. Throw the goal of creating best practices out the window.
  4. Foster Divergent Thinking like a MOFO. Divergent thinking is not creative thinking, rather it’s the ability to come up with lots of different answers to the same question as opposed to coming up with an original idea (which = creative thinking).

[tweetthis]”A 95% fail rate means you’re doing a good job. No, you’re doing a fantastic job.” – Sara Critchfield, Founding Director at @Upworthy[/tweetthis] 

Here are some tactical activities to encourage divergent thinking.

  • Brainstorm problem solving by having your teammates come up with 15 potential solutions to a problem, create 20 mockups for one design change, write 10 potential titles for before committing to an editorial headline.
  • If you are a manager, stop answering and instead question your employees further with probing questions What do you think? What else? Opt for asking “what” over “why” to get more tangible solutions instead of subjective opinions.
  • Intentionally create space and time for brainstorming and thinking. So rarely we take the time to make sure our office environments are fostering the type of thinking and behavior we want. Chris Good, Creative Director of One Workplace, is truly a thought leader, expert, and mentor in this field with the belief that your physical space shapes your culture and your team.
  • Leverage resources like Intuit’s Catalyst Toolkit, Stanford’s Bootcamp Bootleg, or IDEO’s resources on risk, a white paper on risk innovation and employee engagement activities.

[tweetthis]Foster divergent thinking like a MOFO.[/tweetthis]

#8. Values-Driven Actions To Build Risk-Taking Culture.

As we continue to zoom out beyond your personal experience and those of fellow employees, how can actors and influencers bring to life cultures, communities, and ecosystems through the oxygen that is risk taking mentality? A few tenets below to be a builder of these ecosystems through values-based actions from my research. These opinions are my own and it’s my deep-hearted belief that if we take risks in how we lead, how we explore, think, hang out with, work with, and support, we collectively contribute to the impactful serendipity and entrepreneurial entropy that encourages and supports others to do the same in life and in business. Here are my thoughts and insights derived from research and experience.

Collectively contribute to the entropy that encourages and supports others to do the same in life and in business.

Here are my 5 thoughts and insights derived from research and experience.

  1. Top-down Leadership. It needs to come from the top. Leaders, influencers, and top organizations with reputable brands, influence, and creators of foundational practices and organizations need to lead by doing. If this is you, with great power comes great responsibility and take on the responsibility of risk taking for the greater good of a strong entrepreneurial ecosystem. Though you may feel you carry more consequence for your failures than your employees, your power to influence others and create a ceiling on what is considered “safe” can be a gravitational force field to keep masses down. Encourage risk by risking yourself. Doing is better than saying (hopeless cliche, but true nonetheless).
  2. Diversify. Infuse as much diversity as possible. The definition of risk aversion is, in fact, inhibiting consideration and implementation of alternative models. Question existing models, accept divergent ideas and embrace “the other” in business and in life. Hire and hang with people from all different genders, races, religions, ages, political parties, and general tastes and takes on life. You may never agree, but you can break down those barriers and silos which make you categorize those different from you as the “other” and get access to a new perspective from your own that might not change what you think, but may change the way you think of others. The more diverse people and infusions of different opinions, experiences, and lifestyles, the more likely you are to find refuge and get a new lease on life through an alternative lens. The more experiences we are exposed to and people we see as different, the more agile, empathetic and understanding we become – all important muscles to strengthen the values supporting a risk-taking culture.
  3. Curiosity > Blind Acceptance. Question everything and explore the possibilities. A mantra of mine is: explore widely but deeply. Before inheriting the norm as your perspective, question the blinders that shield you from the alternative view points of what is possible. Push aside a black and white stance and dive into the gray area. Get outside your comfort zone. It’s where the magic happens. Ditch the grind and the prison of what is comfortable and expose yourself to new people, ideas and communities through new meet ups outside your bubble. Something that may seem obviously insane to you or a gargantuan risk may, in fact, be taken down by diving in deeper than the surface and your opinion based on superficial facts and your particular perspective.
  4. Support Business As UNusual. Support debunkers of the status quo and wayward business practices through what you consume, who you follow, what you share, and beyond. I’m not saying that all mainstream business is bad or wrong, I’m just encouraging us all to be evangelists for the hidden gems who may just need more exposure to do more and lead with more influence. Be a fearless follower of your kindred startup spirits and build their global community to further turn up the volume of their voice to be heard from their collective community. Evangelize for those you believe in. Invest in these risk takers who are sprinting down a road less traveled. The more support of a risk, the less risky it becomes.
  5. Radical Inclusivity. No one should be the gatekeeper and feel they are the dictator of a culture or a community. Practice radical inclusivity in your network and events and open up your circle to allow new people, ideas, and business join forces for a stronger community. The more openness and support you show for others, the more they will support you in risky endeavors and the often consequential failure that will ensue.

[tweetthis]Invest in risk takers drinking out of the firehose and sprinting down the road less traveled.[/tweetthis] 

In my ensuing posts, I’ll dive into the 5 other pillars necessary for creating the infrastructure integral to house a high-impact, high-performing entrepreneurial ecosystem. Next up: access to abundant capital. Stay thirsty + stay tuned my friends.

Burning Questions //

  • In what ways do you think you can create a risk taking culture on the bigger level of an entrepreneurial ecosystem? What are most important factors and who are most important influencers?
  • What lessons have you learned in successful entrepreneurial ecosystem creation?
  • What risk-taking lessons have you learned?

[tweetthis]Stay thirsty. Stay foolish. And stay tuned my friends.[/tweetthis]


Read the next post on the 2nd pillar of high-impact entrepreneur ecosystems here.

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