Front Matter – Startups in Action: The Critical Year One Choices That Built Etsy, HotelTonight, Fiverr, and More

JP Silva

Startups in Action

The Critical Year One Choices That Built Etsy, HotelTonight, Fiverr, and More

JP Silva
Toronto, ON, Canada
ISBN 978-1-4842-5786-9e-ISBN 978-1-4842-5787-6
© JP Silva 2020
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To Andre, Matilde, Teo, and all the dragons.


Stories are works of sense-making and weaving, of bringing together dates, subjects, objects, facts, actions, causes, and consequences. Unsurprisingly, we are all very drawn to stories as they inform, inspire, engage, and encourage. Stories about founders and startups are no exception. Entrepreneurship has always been understood as a very strong social and discursive phenomenon, with the process of founding a startup being deeply rooted in social interactions and accounts. Entrepreneurial narratives live off this social embeddedness of founders and startups as they expose and frame the moments of individual and collective success and everyday struggle, the webs of relationships, or the flows of information, capital, and other resources. The dense articulation of knowledge and reflection on experiences, whether wounding or uplifting, renders entrepreneurial stories into potent motivational instruments. Even if they might sometimes suffer from exaggeration and concealment, the portrayal of founders and startups as they act, struggle, reflect, grow, or pivot is tremendously looked for and valued.

The active search for insight from founders and startups, and their elevation into role models, typically starts with the detection of idiosyncrasies and behaviors (the role aspect) and the possibility to gain insight and be inspired from (the model aspect). In order for this to happen, some degree of similarity with the role model is expected, even if the role model may likely occupy a far more desirable position. Without such possibilities, it is difficult for any compatibility to be perceived. While exposure to potential role models through mainstream media has increased substantially during recent decades, these entrepreneurial icons have not always been taken up as role models. As the degree of affinity and relatedness often cannot be established, for numerous reasons including media accounts being too broad and atemporal, most new entrepreneurs end up electing next-door examples that can be more easily observed, approached, and probed.

The choices of new entrepreneurs when choosing influencers and role models should not be limited to those in their communities. The preference for geographical proximity and social accessibility does not always offer a useful range of possibilities for examination of entrepreneurial identities, for comparison of tacit principles and attitudes, and more importantly for exploration of self-determination and self-direction principles. With so many new founders struggling to navigate extreme ambiguity and uncertainty across a global geography, the range of options that can inspire and energize them needs to be enhanced and expanded. In the absence of having direct (literal or virtual) access to influential founders, new entrepreneurs need to at least have access to purposely curated resources that they can use to compare their own journey to the journeys of influential startups and founders, so that they can build their simple or blended role models.

In putting together this book, the objective has been to create a foundation for such a curated resource of dates, subjects, objects, facts, actions, causes, and consequences that can engage and encourage new entrepreneurs to draw insight and inspiration from influential startups and founders and eventually identify tried heuristics and debunked myths to include in their blended role models. In this, the intention is not to encourage imitation of idealized traits and behaviors, but quite the contrary. The detailed and timestamped account of what ten very successful startups and respective founders went through in the first year is to encourage relatedness by way of revealing how close they once were to where many new entrepreneurs and their startups may find themselves at present.

Through timestamping and framing , this book may eventually render entrepreneurship as more or less daunting, as more or less desirable. Fortunately, any personal interpretations emerging from this book, whether encouraging or discouraging, will have to contend with the underlying social, cultural, economic, technological, environmental, legal, and political forces surrounding new entrepreneurs and their startups, just like with entrepreneurship itself.


I would firstly like to thank all the founders and aspiring entrepreneurs that I have met over the years. Learning about your struggles, the uncertainties that you went through, the insights that you looked for, and the gaps that you came across encouraged me to go out of my way to try putting this book together. It may come a little too late, but hopefully you will still be able to find some of the answers that you were looking for. Here is to you.

Shiva Ramachandran and Rita Fernando. Without your confidence and contribution as well as your encouragement and guidance, this book would certainly not exist. You are such stars. I also have to acknowledge the outstanding support from all the other Apress team members. Working on this book as a side project required a lot of patience and understanding, which were always exceedingly available. My deepest gratitude.

Dhiraj Mukherjee, Jeff Fluhr, Shai Wininger, Jared Simon, Amit Ranjan, Martin Rastellino, Markus Frind, David Sacks, Adam Wiggins, and Chris Maguire. I am still in awe as to how so many of you generously shared your stories and your time. Thank you so very much. It was absolutely extraordinary to go through those very exciting first months of your startups and in so much detail with you. Memorable.

James Gibbons, Kristina Flynn, Kevin Fernando, Tabitha Grant, Pankaj Sood, Ambreen Khan, Jarrod Ladouceur, and so many more friends. You never held back on your time and feedback, sharing your comments and concerns so many times and so unreservedly. Looking so much forward to support you as well.

Brian Bulcke. If this book was to have a “ghost” co-author, someone that accompanied the entire journey, suffered and celebrated through all the setbacks and breakthroughs, and explored and savored all the insights and data points, it would be you. The best ships are friendships indeed.

Patricia Bentancur. I still can’t understand how you got me to overcome all my initial reservations and hesitations and take on this untried and untested challenge. The personal doubts and anxieties were so many. I am also infinitely grateful for the unending and contagious weekly motivation and excitement, which, without, would have made many frustrations and obstacles unsurmountable. Palakupsa.

I would lastly like to thank every reader. I hope you find in these ten stories the inspiration and insight that they were set out to convey. And if you are starting or about to start your entrepreneurial journeys, I am genuinely excited that you may well be where once were many of the successful entrepreneurs and startups that you will read about. Godspeed.

About the Author
JP Silva

is a fellow of the Royal Society for the Encouragement of Arts, Manufactures and Commerce. He has a PhD from the University of Cambridge, where he spent several years researching the development of several technology startups based in the United Kingdom and the United States. When he is not learning from successful technology startup founders, you can find him working with early-stage entrepreneurs, another of his strongest passions. To bounce off ideas on how to get started on your new side project or share the first year of the technology company that you sold or took public, drop him a note .