Dear Startup CEOs

Dear Startup CEOs

The four lessons that made the biggest difference for Wiley Cerilli, founder and CEO of $100M acquisition SinglePlatform.

Being a founding CEO is hard. It’s an emotional roller coaster filled with incredible highs and unimaginable lows — sometimes in the same day.

The weight of your team is riding on your shoulders and it’s up to you to make things happen. It can be a lonely job. However, through that process, amazing things can happen and you learn a lot along the way.

This was most certainly the story of Wiley Cerilli and SinglePlatform. In just over two years, Wiley built the company from a napkin sketch (which he sold door-to-door) through a successful exit. We were fortunate to partner with Wiley when he raised his first round of capital back in 2010.

When Wiley exited, he did what many other First Round CEOs have done — he wrote a letter via Network (our internal collaboration platform) to his fellow First Round CEOs to share what he had learned during his journey. It was one of the most thoughtfully written summaries on company building I've ever read. He agreed to share it here for the first time publicly.

I hope you enjoy it as much as I did.


Howard Morgan


Dear First Round CEOs,

As some of you may know SinglePlatform announced that we were acquired by Constant Contact. Although this is an amazing event for all of us here at SP, one downside is that I will no longer be a First Round Capital CEO. I wanted to take this time to quickly thank you all, thank the FRC team, and also share a few things I learned along the way besides what was in my exit interview here.

I’ve learned a lot from being at two companies with successful exits. Most of all, I’ve learned that I’m not very good at many things, and that I’m only good at a few things. I can’t tell you how to build the best product, how to manage your financials, or how to best market your business, or even write a grammatically correct letter (see this letter). I can tell you, however, that focusing on the following fours areas where I am actually good at, helped me get to where we are today.

1. Building & Managing a Team

“Great teamwork is the only way we create breakthroughs that define our careers.” — Pat Riley

Your job is to create the best team. It’s not to execute.

I spent over 60% of my time trying to improve the talent on my team at all levels.

"The one thing I know is that you win with good people." — Don Shula

We defined our culture very early on. We hire people we really like over more talented people, and we let go of top performers because they were disrupting the environment.

This goes for investors as well. FRC are not good people, they are great people. We could not have done this deal without them. Howard and FRC were always there to make the right decision when I needed them.

We even hired GREAT lawyers. Ward Breeze and his team at Gunderson helped save our business and get us the best terms. Great lawyers, great people.

"He who says he can, and he who says he can't, are both usually right." - Confucius

Hire those who say they can and have shown that they can.

Hire people with positive outlooks, negativity is viral and it only takes one person to turn a team upside down. It happened to us twice, and both times the people were gone, our company was better.

"Fire people as quickly as you hire them." — I think Jeff Weiner of LinkedIn (but I'm not sure)

I believe he said something to the extent of, “As soon as you are having doubts about someone, it means they are no longer doubts.”

Do not settle for people who are “OK.” As soon as you settle for OK, your business will be only that.

2. Execute

"A good plan violently executed now is better than a perfect plan executed next week." — George S. Patton

We never made our plans very complicated. We focused on monthly goals and didn’t think too much beyond that.

We poured our resources into doing a couple of things right until we had the money to then focus on 3 things.

“Be so good they can't ignore you.” — Steve Martin

Our management team decided early on that we were going to make a name for ourselves, and it could only be for 1 to 2 things.

Pick those 1 to 2 things and tell the market you are known for it. Tell them in articles, tell your team, tell everyone, and then execute.

"The winner in the fight between the bear and the alligator is determined by the terrain." — Jim Barksdale (I think. Angus Davis from Swipely told me about this quote.)

Compete on the terrain in which you can win on.

We compete in the local space and I know how to sell and create teams. Product is not my specialty, and neither is marketing, so we didn’t try to be the absolutely best designed etc… product.

“We will either find a way, or make one.” — Hannibal

Nuff said.

3. Inspire and Motivate vs. Dictate

"Our chief want is someone who will inspire us to be what we know we could be." — Ralph Waldo Emerson

People want to be led. They yearn to be inspired. Give them a higher meaning to being at your company.

Challenge them to be better. Do not let people settle.

“The task of the leader is to get his people from where they are to where they have not been.” — Henry Kissinger

Convince people that together you will help them to take the company to where they thought was not possible.

Make sure the leadership team is the most on board because they will be the ones getting everyone else to drink the juice.

If you can’t give motivating speeches, use ppt with music.

“Don’t be an idiot. Get on a rocket ship. When companies are growing quickly and they are having a lot of impact, careers take care of themselves. If you are offered a seat on a rocket ship, don’t ask what seat, just get on.” — Eric Schmidt to Sheryl Sandberg

In my last company-wide email l referenced a part of Sheryl Sandberg’s speech that she recently gave at the HBS graduation. During the speech, she described her hesitations in accepting a job offer with Google, which vanished when Eric Schmidt, the company’s former CEO, told her the above. I love telling this to people to help them to see a longer-term fit with them and the business and to stop worrying about their tasks they are responsible for today.

4. Celebrate with the team

“Celebrate your wins.” — Jed York, CEO 49ers

Make sure you and you team celebrate the wins even when they are small wins. I know it's stressful being the CEO, but you must celebrate with your team.

Set goals earlier on that you can hit to build the team’s confidence in their ability to hit goals and that you know how to set them.

I send out a weekly email to the whole company of what each dept’s goals are and if we have met them. We go go-karting, have a gong in our office, and we celebrate once per month if every group hits their goals.

“It's not whether you can become successful, it's how many people can you help become successful.” — Magic Johnson

My proudest moment was knowing that every person in our company was in a better place because of our deal with Constant Contact.

If you can put your people in a position to win, your business will win.