One year ago today I quit my job, leaving my comfort zone to start a new business. The thought had been circling in my mind for some time, but I’d always silenced it with self-doubt and a perceived sense of security from my regular paycheck. But last October I finally stepped into the unknown, thanked my fantastic colleagues for their inspiration and encouragement, and moved from London to San Francisco. Here’s my retrospective on entrepreneurship.

Entrepreneurship (and in fact any new venture) is never really what you expect. In many ways that’s the point. It’s a voyage of personal and professional discovery — about yourself, your customers and your business model. There isn’t a linear trajectory toward success or failure. It’s an experiment, and a challenging one at that.

I spent today at Ryōan-ji in Kyoto, a Zen temple with a famous rock garden where only fourteen of the fifteen stones are visible at any one time. It is said that only through attaining enlightenment can one view all fifteen stones at once. I thought it was the perfect place to run my own personal retrospective of the last year. Here’s what I’ve learned so far.

Clarity of Vision Matters

A clear vision sets the context for all the other pieces of the venture to fall into place. How well I communicate my vision matters — and maybe it even matters the most. Being able to clearly articulate my vision helps people connect with it, and if people can connect with it they can buy into it. My vision also informs what matters most and helps me to prioritize what and where I invest my most valuable commodity — time.

I constantly ask myself, ‘Is this helping me move towards my vision or not?’. If it is, do it. If not, don’t.

Define Success Over Multiple Time Horizons and Perspectives, and Review It Regularly

In conditions of extreme uncertainty I need a mechanism to make difficult decisions. Without anything to be accountable to, it’s easy to continually spin wheels, burn time and convince myself that I’m making progress.

Every well executed experiment begins with defining success before it starts. I have a regular cadence to set and evaluate target conditions over multiple time horizons (one week, one month, three months, six months, two years) and perspectives (personal, business, customer, market). This designs rigor, discipline and good governance into my operation rhythm.

If Business Partner(s) Aren’t  100% Committed—Don’t Continue Together

If the team has misaligned expectations or if someone discovers that the reality isn’t what they thought it would be, it’s best to accept the situation, part company and move on. Team members who aren’t fully committed can cause friction, poor decision making and negatively impact others.

Just as no business plan survives first contact with customers, the same goes for personal assumptions and entrepreneurship. They’re hypotheses that only get exercised when tested. Failing fast, cheaply and early is as successful and validating that you’ve found a willing team.

Work Hard To Be Self-aware

I’ve learnt to understand what I like and don’t like. Where do I need help? What are my gaps, and how can I plug them? No one excels at all aspects of life or business. The trick is to enhance strengths and manage weaknesses. If you struggle with accounting, get an accountant. If your enjoy writing blogs, write them. Don’t ignore what needs to be done because you don’t like or understand it, it will come back to bite you – it’s only a matter of time.

Accept Self-doubt and Trust Yourself

I constantly ask myself questions like ‘Why me?’, ‘Do I have what it takes to make this work?’, ‘Should I have left my job, friends and city?’ or ‘Was this a bad idea?’ These thoughts run through more people’s minds than you would think. Questioning yourself can be healthy, but over-analyzing less so.

I remember that the reason I decided to get out of my comfort zone was because that’s where the real magic happens. I remember to trust myself, the decision I make and my ability to get there. I’ve never met anyone who said they wouldn’t hire me because I tried to start my own company, regardless of whether it worked out or not. Actually they admire it, often sharing how they wished they had tried it but never did. Remember that.

Entrepreneurship Is About Embracing Uncertainty As A Lifestyle

There will always be ups and downs. To deal with this I have what I call an emotional control chart. I celebrate the wins, but don’t get too drunk on them. Similarly, when failures happen I don’t get down, but gather the lessons learnt and keep working. Persistence is what breeds success.


From Kryo Beshay Jul-31-2015 It’s in my office to constantly remind me and keep me focused on what matters. Thanks Kryo!

Not Many Other Jobs Offer The Same Level of Experiential and Exponential Growth

I moved to a new country, started a business, immersed myself in a new work culture and learned a new tax system along they way! I’ve done aspects of business I’ve never had to do before – digital marketing, accounting, business operations, procurement processing, company legislation and healthcare policies. The list is endless, but so has been the growth.

I’ve learnt new skills, and learnt by doing. I’ve discovered new things about myself I never knew existed (good and bad) but it’s been great. I’m more self-aware, confident and humble. No other job has offered me this level of experience. That alone has been worth the investment.

Do Everything Manually—Then Decide What To Automate

When I was a developer I learned the hard lesson of automating too early. Automating removes you from the process and prevents you from learning more from it. When you experience how each aspect of a business operates you understand how it works. By feeling the pain you develop context to make better decisions on what to outsource, automate, or stop doing altogether.

Doing expenses still sucks but I have a much better insight into where expenses come from and go to. Doing things manually helps me to build that context and understand the process. Then I can decide how to handle it going forward.

Find A Mentor—Even Better, Find A Few

I’ll never have all the answers. No one does. Mentors won’t either, but the best ones know that. Their role isn’t to provide me with answers, it’s to help me ask better questions – of myself, my direction and business purpose.

I’ve been lucky to have a lot of great people share words of encouragement and advice with me over the last year – my late cousin Philip J. Moore specifically. Thank you to everyone who made time to help me. The list is long. I hope it continues to grow and I give a little back in return.

Entrepreneurship can be a lonely existence. Don’t be afraid to reach out to people for support and advice. And try to share what you’ve learned with someone you know who is starting out. Mentoring other people is as powerful, if not more, than receiving guidance from others.

Have A Small Trusted Group Of People For Collaboration, Discussion and Support

Having a group of people I respect and admire to test crazy ideas, hypotheses and thoughts with has been invaluable. Their social, emotional and operational support is essential. My group started with a few people in a Slack group. We help and encourage one another, and collaborate on all sort of initiatives. It’s a community I never would have discovered without changing my circumstances, and I couldn’t be happier with the result.

Your Network Is A Great Source Of Business Opportunity and Growth

My personal network is a source of hidden strength and has rescued me at least twice. Building and nurturing that network is one of the best investments I’ve made. Seek out interesting people, with a growth mindset and appetite for learning. The future belongs to folks like that.

The people I’ve enjoyed working with are the people I want to continue to work with in the future. Value great working relationships when you find them because they are difficult to find.

There Isn’t Just One Shot, There Are Many

Many people mistakenly believe that you only have one shot at success. That introduction, that meeting, that deal. There’s nothing further from the truth.

Entrepreneurship is about life, and life is about growth through learning experiences. Sometimes things I’ve tried have worked, other times they haven’t. The trick is to pick yourself up, dust yourself down and ready yourself for your next shot when it comes around, because it will come around.

As my cousin Philip always said, “If you are still breathing, you haven’t failed. Make sure you learn something for the next spin. Take the night off, send your special someone some roses and go out and see something to inspire you.

Today, I found myself at a rock garden in Kyoto. Tomorrow I’ll start year two.

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