10 Things I Learned by Taking 250 Coffee Meetings in 400 Days

Meeting is the name. Coffee is the game. As the title suggests, I took 250 coffee meetings in 400 days.

My main motivations were 1) I like meeting and connecting people and 2) I had just quit my job and had no Chicago connections. I wanted to get connected in a deep way.

Here’s a summary of what happened as a result of these coffee meetings:

My lie detector improved dramatically. I’m not saying it’s perfect, but I have gotten good at determining who’s telling the truth and who’s exaggerating. It’s now easy for me to answer these questions: Are you just trying to get me to develop your product for free, or do you really want technology insight? Do you really have 3 full-time employees, or are they all unpaid interns? Is your startup really doing well, or are you just saying that to make yourself feel better?

Trust is everything. “Do I trust you?” is the question I usually ask myself when meeting someone over coffee. My first goal in any coffee meeting is to understand how I can help this person. Whether it’s offering technical advice or connecting them to another entrepreneur, developer, business owner or investor, I really just want to help. I’m a give forward type of person. If I trust you and like you, we’ll connect. Sometimes I’m on the fence about someone. I’m not really sure what this person is really up to even after a coffee meeting. I will shoot someone else an email or ask someone I trust what they think about that person. Which brings me to my next point.

Some people have no business being entrepreneurs. I hate to say this, but some people really should not start a project or quit their job to start their dream project. I get the hustle and persistence and follow your dreams and all, but there has to be a point where you look in the mirror and ask yourself what you’ve really accomplished in the past 6 months or year. No product, no co-founders, no customers, no funding, no industry knowledge and no real vision. Sure, it’s a great learning experience, but I sometimes question why people do it. Get a real job and get paid.

Under no condition should you talk smack or gossip about another person or their business. I made this mistake once and I’ll never do it again. Gossip was going around about a startup funding situation, and I repeated what I had heard at a Starbucks. I’m 99.9% sure the company’s CEO was sitting right next to me and heard everything I said. That’s the last time I spread gossip about someone I didn’t even know. I felt like crap for days. Just don’t do it. I’ve also made the mistake of telling someone I hate a product, only to discover their best friend was the founder of that product. It just doesn’t pay to talk smack. Nobody wins.

People are surprisingly open about difficult situations. I don’t know if this is a Chicago thing, a startup thing or people just trust me thing, but for the most part people are willing to share the troubles their companies have. I like when a meeting starts with “I need help.” It takes guts to say that and although I usually can’t do much to solve their problems, I still want to help this person. I appreciate when someone is vulnerable and opens up.

A bad reputation can screw you, quickly. Once word gets out that you’re a bad person or that you do shady business deals, word travels fast. Actually the word travels to everyone besides you. If I ask a trusted person about someone else and I hear bad things, I immediately discredit the other person. It was as if we never had coffee.

Execution matters. Technical or non-technical, I just want to hear you created something, anything. It shows that you care and you can execute at the bare minimum. If I’m talking to you about the same idea you had a year ago, the conversation isn’t going to last long.

CREATE.CREATE.CREATE. Even if you create something that sucks. People like other people who create and execute.

The most powerful question you can ask is, “How can I help you?” It’s a game-changing question. The look on someone’s face and the contemplative sigh while they think about how I can help them is awesome. It needs to be asked at every meeting. This question can open doors and opportunities.

The more I see you, the more I like you, and the more we can help each other. The coffee meeting is just the start. The people I see consistently at meetings and networking events are the people I end up doing business with. It shows they care about the community as much as I do, and I appreciate their efforts more.

Being addicted to coffee is awesome, but sucks at the same time. I was anti-coffee in a previous life. Now, I’m all about it. I seriously cannot imagine a morning without coffee. It’s hot and makes me feel awesome. It sucks because I know it’s not good for me. I want to stop. But I probably won’t. Coffee is for closers, right?

Being connected in any community opens a lot of doors. The people I would have never had access to a year ago are now people I talk to often. And because I have worked to become connected in a community, I receive more responses to my cold emails.

Yes, coffee meetings can be a huge waste of time. I don’t take coffee meetings to make me feel busy. What I did was necessary to build my personal platform in Chicago, but not necessarily the best route going forward.

Overall, those 400 days were amazing. I don’t regret taking that many coffee meetings. It was one of the best decisions I’ve ever made.

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I am the author of the book Fire Me I Beg You and an experienced independent IT Consultant. If you want to advance your career by leaving your day job, sign up for the Summer of Quitting email course. It will be the best decision you make all day.

If you want to get a hold of me directly, please send me an email to robbie.abed@gmail.com. I read every email.