Building the next successful startup requires grit, sweat and tears. But what happens when you chase your dreams and don’t succeed?

A Brief Introduction

A little over 10 years have passed since I graduated from college in Ireland. During that time I started 3 companies (2 failed), and an independent consultancy. I worked with 5 startups at varying stages of growth; EngineYard (pre-acquisition), New Relic (pre-IPO), Fivetran (pre-IPO, I currently work here), Intercom (pre-funding, circa 2011), and a non-profit: ChangeX.

Across those companies I’ve worked as a full-stack developer, sales engineer, technical support engineer, alliance manager, product manager, account executive, and most recently as a solutions architect; each role a career path in its own right.

Having had time to reflect on the first decade of my career has made a few things very clear:

• My career path has been everything but linear.
• The 3 years of my first startup taught me more about myself, people and business than any other point in my life.
• Despite the painful experience of shutting down a business, I discovered I had grit, driving my passion and perseverance.
• The compounding benefit of experience and learning has set me on a great path, but the ambiguity of what lies ahead remains.

Grit and Lessons Learned

I’ve started this blog to share my experiences and lessons learned, based on the past, present and what’s yet to come. When my first company failed, I wrote a blog post announcing we were shutting down, and detailed some of the factors that contributed to this event. In Ireland, failure was rarely spoken about. Realising I had already lost everything, I figured I had nothing to lose and so I published the blog post, shut my laptop and went for a walk. What followed a mere 24 hours later shocked me; a stream of job offers, interview requests from various media outlets, entrepreneurs emailing me to share similar experiences.

Coming out the other side of this experience shaped a key part of who I am today. This deeply rooted emotion is what motivates me now to begin this writing journey.

My Commitment to the Reader

My commitment to you, the reader, is just as as much a commitment to myself. The stories and insights I share should be built on the following pillars:

• Vulnerability. To truly share these experiences I need to be vulnerable, and highlight moments of weakness, fear, uncertainty. There will be no hiding behind the glamorous curtain of Silicon Valley and all its “success”.
• Honesty. I will focus on sticking to the facts, and keeping myself honest so that neither the highs or lows touch the realm of fiction.
• Humbleness. I will leave my ego and pride at the door when I sit down to write. After all, these stories are from me, Kevin, and I am no more or less human than anyone else.
• Insightful / fun. Lastly, I want to ensure that what I share is insightful to the reader, and of most of all fun. Life is too short.

My goal is to publish an article the 2nd and 4th Monday of every month. This bi-weekly routine will hopefully help me build a strong writing habit, but also let readers know when to expect new content.

As I publish this, I am merely days away from becoming a first-time father. And for the first time in 10 years there’s a certain security and “adjusted risk” that has set in as we start our family. This has given me the comfort to sit down, reflect, and write.

So let’s see where this journey takes us!