Three years ago, in the spring of 2012, I got an email from a recent Yale graduate named Chris LoPresti seeking advice for first time entrepreneurs. Chris had started a “rough shell” of a company, developed a minimally viable product, acquired one paying customer, and was trying to decide if he would “go all-in” and attempt to turn it into a business, or, like many of his classmates, take a more traditional job with generous benefits and a guaranteed salary. He was seeking mentorship from older entrepreneurs who had been through the start-up phase before, and wondered if I had any thoughts I would be willing to share.
At the time, I was in the throes of running my startup (incubated at Yale), and had already learned a number of lessons — the hard way — that I was more than happy to talk about. I sent him my thoughts, and did not think much more about it, until I got an email a few weeks ago announcing the launch of Chris’s new book: INSIGHTS: Reflections from 101 of Yale’s Most Successful Entrepreneurs. I downloaded a copy from Amazon and immediately devoured it in a single sitting.
This book weaves together advice from a wide variety of people, including entrepreneurial celebrities like Eric Ries (author of The Lean Startup), Barry Nalebuff (co-founder of Honest Tea) and Kevin Ryan (founder and Chairman of GILT Groupe) alongside everyday entrepreneurs like myself, all in very different stages and types of businesses. From a few sentences to several pages, each entrepreneur shares key lessons from his or her unique journey which, when taken together, reveal the many commonalities that define the entrepreneurial experience.
It is a great read, and as soon as I finished it, I reached out to Chris to learn more about how the book came to be, and what he had learned from the entrepreneurial experience of putting it together:
Kate: When did you realize there was a book here instead of just interviews, and how did you go about getting it published?
Chris: While I was trying to decide whether to proceed with my company, I reached out to a handful of successful Yale alumni who had started their own businesses and asked them for advice. At first, I thought only one or two entrepreneurs would respond to my outreach, but quickly that number became a dozen. The feedback I received was so helpful, that I wanted to share it with future Yale grads — and anyone else wrestling with the challenges of turning an idea into a company.
My first thought was that I could turn these twelve interviews into a series of blog posts, but as the number began to grow, I knew I had to do something more with it. Publishing a book was something brand new to me. Halfway through the process, I realized that the book itself had become an entrepreneurial endeavor! In the beginning, I read everything I could about traditional publishing — finding a literary agent, licensing contracts, distribution networks, etc. However, with all of the major changes in the publishing industry over the last few years, the best option for INSIGHTS was leveraging new publishing technology. I went with a hybrid option and published through Merry Dissonance Press, a boutique press in Colorado that I think is at the sweet spot of technology, experience, and most importantly, author control. I didn’t want this book to get shelved because the publisher had other priorities this quarter. I wanted to get the book, and the advice inside it, to as many people as I could.
Kate: The book offers a remarkable diversity of perspectives. How did you decide which entrepreneurs to include in the project?
Chris: I wanted to emphasize the diversity of Yale alumni and the diversity of their startups. No two startups are the same, so the more variety the better. While we do have some major internet tech founders featured in the book, INSIGHTS also includes startups that focus on education, retail, food and beverage, finance, supply chain, and nonprofits.
Kate: Was everyone willing to help you?
Chris: Every entrepreneur has sought advice from mentors, advisers, and peers. All of the entrepreneurs I contacted and portrayed in the book were excited by the opportunity to share what they have learned with the next generation. The hardest part was convincing them to spend some of their precious time reflecting on what the most helpful advice or lesson would be to share with other young entrepreneurs.
Kate: Did any of the contributions surprise you? If so, which one stood out most and why?
Chris: A lot of the entrepreneurs in this book surprised me with their advice. One of my favorite sections is from Jens Molbak, the founder of Coinstar — those green kiosks at grocery stores that convert your jar of loose change into bills. Coinstar has processed over a trillion coins worth over $40 billion dollars, and they have donated $80 million dollars of profit to charity. Molbak’s advice is titled “Doing Well and Doing Good.” Coinstar gave consumers the choice between converting their loose change into cash or donating it to charity. It paid off big time for both the company and charities, and the U.S. government as well, by saving over $200 million a year in unnecessary coin production.
Kate: What piece of advice resonated most with you personally?
Chris: Another thing that Jens Molbak shared is a suggestion for where entrepreneurs can find their next big idea: “Want to find a cool idea for a new startup that can grow into something substantial? Look to the public sector. Yes, that’s right, to government. I believe that new startups can thrive where there are inefficiencies in the market, and the government offers many opportunities. Pick any federal or state organization and ask if there is a way for the private sector to help provide better service(s). Do research, brainstorm, and see what you find.
Kate: What are some of the common themes you saw emerge from the collection?
Chris: It’s all about the people. The number one theme shared by these 101 successful entrepreneurs is that people matter the most. What’s really interesting is that all of these entrepreneurs were asked to pick one piece of advice, and even though the group of entrepreneurs in this book have started completely different types of companies, they focused on the importance of hiring the right people as their best advice.
One of my favorite chapters comes from Kevin Ryan, one of the most successful serial entrepreneurs whose companies include Business Insider, MongoDB, GILT Groupe, Zola, as well as being the former CEO of DoubleClick. His chapter focuses on the keys to hiring the right people. It’s too important to distill down to one sentence here, but it’s a lesson I will use in every company I am a part of, going forward.
Kate: Looking back, would you have done anything differently in the process?
Chris: Now that’s pretty ‘meta’ — lessons learned about writing a book on lessons learned. Putting this book together was, in fact, very similar to starting a company. There is legal, project management, assembling a team, accounting, marketing, and technology. While I am familiar with many of these functions, I still had to seek advice from people who had done these tasks before. For anyone who plans to write a book, I suggest you do three things: 1) Read Guy Kawasaki’s book, APE; 2) grab coffee with at least three different people who have published a book before; and 3) keep track of milestones and the people who have helped you along the way.
Kate: What do you personally plan to do next? What's your next venture?
Chris: The common theme in my two most recent entrepreneurial endeavors is community. I knew that one of those communities included people who could help support what I was passionate about, so I reached out to them — and that’s how this book came to be. My current entrepreneurial venture is called TouchPoints. Our tagline is “Reconnect with Everyone” — because we help brands reconnect with former customers, and increase engagement with current customers through better data management. At TouchPoints we are on a mission to empower communities through stronger engagement. I think all of my future ventures will revolve around this theme.
Kate: Is there anything else that you wish to share with the readers about the book?
Chris: Yes. I hope that this concept of looking at the communities you are a part of and reaching out to seek advice and/or mentorship becomes contagious. A book like this should exist at every school, organization, and company.
I should also mention that 100% of the profits from the book are going to STEM and entrepreneurial causes. We are going to distribute the funds based on reader-suggested organizations, and everyone interested gets to vote.
You can find INSIGHTS: Reflections from 101 of Yale’s Most Successful Entrepreneurs on Amazon and follow Chris @Chris_LoPresti
