Dear Entrepreneurs

Dear Entrepreneurs,


Today, I’m officially joining First Round     as a Venture Partner in New York. I couldn’t be more excited, but it’s also given me a chance to think about the long, unexpected road that got me here —a road that many of you either know well or are just starting down.

When I was 19 years old, I dropped out of New York University to join the founding team of a new startup called SeamlessWeb. The company became successful early on, and after leading the sales and partner services divisions and serving on the executive team there for 10 years, I felt “ready”to start my own company, SinglePlatform. I left thinking my business would follow the same ascending path as Seamless.

I opened SinglePlatform’s doors with a beautiful vision of success on the horizon. About 99% of me felt good and optimistic, and 1% was completely stressed out. Of course, it only took a couple of months for those numbers to flip. I worried that my product sucked, that customers weren’t buying, and about any number of bizarre bugs.

I also couldn’t help but notice the dwindling balances in my bank accounts (personal and business) and the effect it was having on every aspect of my life. With a lot of hard work, fingers crossed, and experimentation —especially around sales —things turned around, and SinglePlatform was happily acquired by Constant Contact two years ago. I have learned a lot from these experiences, and from sitting on the executive team of a public company for the last two years, but one thing is clear: I know for a fact that I couldn’t have weathered all the storms I encountered as CEO without my amazing teams at both companies, and for that I will be eternally grateful.

An entrepreneur friend of mine recently observed that starting your own company is like that scene in Top Gun when a relatively calm Tom Cruise sees an enemy fighter plane coast across his radar, and then, seconds later, a dozen other enemy planes appear. It’s too late for him to turn around, all he can do is fly and fight.

The truth is, if founders knew what they were up against, many would never leave the runway. That said, hearing other entrepreneurs share their startup experiences has saved me from hundreds of metaphorical fighter planes. They gave me the data points I needed to make more educated and confident decisions. Just like the best teachers I had in school, they didn’t tell me what to do —they simply offered me their stories, stories that included some good decisions, many wrong decisions, and more than a few times when they were flat out luck. They left their stories with me, to apply the wisdom of their experience as I chose.

So when I first heard about the opportunity to join First Round, I was intrigued. Here is a firm that is all about helping founders share stories to help each other win. I may not be a seasoned investor, but with this emphasis on community, I feel like I can play an important role.

What I am is an entrepreneur. I am an entrepreneur who knows what it’s like to spend countless sleepless nights worrying. I am an entrepreneur who has 15 years experience scaling very effective sales operations. I am an entrepreneur who made many mistakes, but who was still fortunate enough to be a part of two incredible teams that scaled businesses from day one through successful acquisitions. I am an entrepreneur who will not tell you what to do, but will tell you a lot of stories to help you as you build your business. And finally, I am an entrepreneur who loves, more than anything, to help other entrepreneurs achieve their potential.

That is why I am taking this job —for the same reasons I wanted First Round to lead SinglePlatform’s seed round and sit on our board. First Round is a rare, remarkable team run by entrepreneurs for entrepreneurs. They offer both a tremendous amount of operating experience and an amazing platform that connects dozens of experts across the portfolio to share their knowledge, compare notes, and achieve together. Additionally, because I had the pleasure of seeing First Round in action as investors, I know that they go above and beyond to do the right thing for founders in good times and bad. This is truly unique.

I am thrilled and honored to be First Round’s first ever Venture Partner, and to be joining Howard Morgan and Chris Fralic on the investment team in New York. I can’t wait to help the hundreds of entrepreneurs in this community learn how to build and sell to the best of their ability —and learn from some of the best investors and entrepreneurs along the way. Starting today, I invite founders to reach out to me any time to talk through their business challenges and opportunities. I’m looking forward to working with all of you.

Always here to learn and help,


Wiley B. Cerilli



  1. Congrats on your new adventure Wiley. Fly high & make a positive impact.

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