Felipe Millan (SendGrid) on bad co-founders, joining a company with a startup mindset, and happiness

Frank Heijdenrijk ♛
Startup Stories
Published in
7 min readAug 10, 2018

At Pirate Summit, we had the opportunity to talk to Felipe Millan. He is the Community Development Manager — Developer Evangelist of email delivery service SendGrid, a Denver, Colorado-based customer communication platform for transactional and marketing emails.

Originally from Santiago, Chile, that is also where his entrepreneurial journey started. Right after an earthquake, he started an entrepreneurship agency with his brother, helping people start and grow their own companies. Both of his parents are entrepreneurs, and even his grandparents had their own businesses. At the age of 16, Millan started selling second-hand instruments. After that, he started getting into online marketing. We talked to Millan about success, advice, and failures.

Felipe Millan

What does success look like to you?
“Success to me means a happy steady mind: when you feel like you’re doing something good. Or when you’re feeling that somebody else, based on your feedback and story, is rethinking what they’re doing. If they then actually take action in one way or another, that doesn’t matter. But when people say ‘It is really interesting, I didn’t think about it’, or when they can learn from my f*ck-ups; that’s success to me.

As a startup guy, I don’t have a unicorn or a company worth a hundred million dollars. But I can still share my failures, and that is part of why I am still happy today.”

“…if something does not make sense, that is the first red flag.”

What advice would you give to someone who thinks about setting up a company?
“I would tell them to be honest with themselves and check whether their idea makes sense. Go out into the streets, give a short pitch to people, and ask them what they think. I once participated in one of the Lean Startup Machine workshops in Chile, because I wanted to make an app that helped me get money back from my friends. I kept paying for my friends when going out and it’s awkward to ask your money back. You’re not going to ask your friends ‘can I have my money back?’ five times a week, but as a student, I needed my money. So, I pitched the idea at the Lean Startup Machine, and they selected me. I had a team of five guys and I was the only local. During the workshop, we had to go out — get out of the building. And, in five hours we made $150 with the team. The simple question we asked people in the streets was ‘would you pay a monthly subscription to get your money back from your friends?’, and many people were like ‘f*ck yeah’!

What I took from that experience is that if the first twelve people tell you it doesn’t make sense reshape it — I believe that if something does not make sense, that is the first red flag. And making sense is not the same as your idea being useless, stupid or bold. It’s just that first reaction that you have to things, like finding something interesting — then it probably makes sense and you you can think about how to execute that idea to make it useful. So, then go back onto the street: First, explain the problem. Then, ask them if the problem makes sense to them: ‘I can’t get my money back from my friends. Would you use an app to get your money back?’. People will tell you from their point of view if it makes sense. To me, that’s the most simple, basic discovery. That allows you to ask yourself ‘how can I make it? How can I find out if it’s worth building?’.

I also use the grandma test. I go to my grandma and ask if she has the problem. She will then ask me why I want to make it. She will ask me numerous times. And that helps me to shape it.”

“Co-founding with a friend is not necessarily a good match.”

What would you consider your biggest failure and what can other people learn from that?
“I chose the worst co-founder that I could have ever imagined. In two weeks, he killed two years of our company. He burned out the whole shed. He disappeared with everything. It was painful. I lost a lot of friends because focusing on that startup for that long. After working on a project for a long time, I felt like I needed a co-founder. He was a friend. He was great at coding. Then something in his personal life happened and he disappeared.

Co-founding with a friend is not necessarily a good match: you have to be in control of everything. For example, I trusted my co-founder blindly, and I didn’t ask him to document the accounts, or access to these accounts somewhere. I took care of the strategy, and follow-ups, but when I asked him where the actual software was he was gone. We were in an accelerator with the company, and all of a sudden I had to tell them I didn’t have a company anymore.

They say starting a company is all about the relationships you create, and that is true. You’re going to spend more time with that person and that team than your partner. You’re with them every day. Your co-founder is the one who sits next to you, who tells you when you’re wrong. And you need someone who can take criticism, and who can listen to your points and who can help reflect on your own thoughts. If you have that, you have the right co-founder.”

SendGrid’s logo

What do you consider your biggest struggle right now?
“It’s way too easy to come up with a startup idea now, so I would say the struggle is about ‘stop[ping] the bullshit in the startup scene’. You can just buy any SaaS platform or full-made app, create a landing page, and you have a company. But to me that doesn’t mean you have a company, you need to create your company. You need to know how to scale and how to grow it. I also think that there’s too much access to proper mentorship and proper knowledge, but some people are not taking it: they’re filling their minds with their Silicon Valley-show mindset.

The best decision, as an entrepreneur, that I made in my life is to join a company with a startup mindset: SendGrid. It’s the first startup from Techstars to IPO NYSE: SEND, which happened in November 2017. In my three years at the company, the main thing I have learned is how important processes are. Many founders say it’s corporate BS, that it’s not lean and that it’s stupid, but I see it differently. Right now, we sit down and think about why we do something: What do you want to get back from it? How are you going to call a campaign successful? What is the value proposition? My manager and director is always telling me to write these goals down in a document. And it’s not about writing a long document, but about knowing why you’re doing something and what you want to get out of it and what kind of tools and implementation, will be defined after it’s agreed as a team that that project is needed. After that as a team you can see if you already have the resources and tools, maybe someone in the team is already working on it or has the tools or resources to execute it. Basically, you’re creating a strategy that reminds you of why you’re committing to these processes.

I think that the founders that really learn and have learned from their failures are the ones that are in this environment for about five years. To me, because of working at SendGrid, I finally ‘got it’. And that brought me to now first putting down my thoughts and then start doing things.”

What is your favourite quote, something you live by?
“My personal favourite quote is “Just be happy”. If you’re not happy while running your startup, you’re doing something extremely wrong. Everybody wants to make an impact. Everybody wants to be a billionaire. But if you are not happy, nobody will be happy. Whenever I see the CEO SendGrid he always has a huge smile, ear to ear, on his face. But he’s also extremely focused. For example, I’ve only been to the headquarters of the company in Denver a few times over the last three years — but he knows my name. He makes sure he knows my name. He asks me about my family, added me on Facebook, and he even shares his family life there — so I can see that side of him too. I could not join a company where someone doesn’t do that. To me, family comes first. And that implies for me that when you’re not happy as a founder then you’re not focused. So, just be happy.”

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Frank Heijdenrijk ♛
Startup Stories

Sometimes I believe I have amazing things to write about. Most of the times I am absolutely wrong.