17 Things I Have Learned From Taking Over 250 Coffee Meetings in 400 days

Meeting is the name. Coffee is the game.

Mark Suster inspired me to take 50 coffee meetings. I took his advice, and then I took it again, and again and again and again. To the tune of 250 coffee meetings in 400 days. The result was phenomenal.


My main motivation to do this was because 1)I like people and 2)I knew no one in Chicago after I quit my job. I wanted to get connected in a deep way.

Here is a summary of what has happened:

  1. My bullshit detector has improved dramatically. I’m not saying it’s perfect, but I have gotten very good at determining who is telling the truth and who is exaggerating. 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 fulltime employees, or are they all unpaid interns? Is your startup really doing well, or are you just saying that to make yourself feel better?
  2. People think that developers are going to solve all of their problems – “If only I had a developer, this business would take off and I can get the real funding I need to take this off. I need a developer to take on sweat equity”. I sigh every time I hear this. Somehow, someway successful starters with non technical backgrounds make things happen with very little money. These are the people who developers want to work with! Not the people who “just need a developer to finish the last 20% of a project started by a college kid over the summer”.  To quote The Social Network “If you guys were the inventors of Facebookyou‘d have invented Facebook”.
  3. Some people have no business being entrepreneurs – I hate to say this, but there are some people who have no business starting a business or quitting their full-time jobs to pursue a project. I get the hustle and persistence and follow your dreams and all, but there has to be a point where you look at yourself in the mirror and ask yourself what have you 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 extremely great learning experience, but I sometimes question why people do it. Get a real job and get paid.
  4. 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. There was gossip about a startup funding situation and I repeated the gossip at a Starbucks and I’m about 99.9% sure that the CEO of the company was sitting right next to me and heard everything I said. 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 and find out that the person’s best friend is the founder of that product. It just doesn’t pay to talk smack. Nobody wins.
  5. People are surprisingly very 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 very open about the troubles they are having at their companies. When a meeting starts with “I need help”. These are the meetings I like, because it takes guts to say that and although I’m usually of very little help – I want to help this person. The person has opened themselves open to be vulnerable, and I appreciate that.
  6. 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 understanding how I can help this person. Whether it is technical advice or connecting them to another entrepreneur, developer, business owner, investor, etc. I really just want to help. I’m a give forward type of person. If I trust you and like you, I will connect you. Sometimes I’m “on the fence” with 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 a trust about what they think about a person. Which brings me to my next point.
  7. A bad reputation can screw you, very quickly – Once the word gets out that you’re a bad person or you do shady business deals, the 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 about them I immediately discredit the other person. It was as if we never had coffee.
  8. I still love Dunkin Donuts more than Starbucks Coffee any day of the week. DD is so simple when ordering. Medium coffee cream and sugar please. None of this special edition coffee that they got from some tribe in Africa or Nicaragua type coffee crap. I do drink more Starbucks than I do Dunkin Donuts because taking coffee meetings at Dunkin Donuts is not really an option. DD all the way.
  9. Shipping Matters. Technical or Non Technical, I just want to hear you shipped 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. SHIP.SHIP.SHIP. Even if you ship something that sucks. People like other people who ship.
  10. The most powerful question you can ever ask is “How can I help you?” It’s a game changing question. The look on people’s face and the big sigh while they think of how I can help them is awesome. It needs to be asked at every meeting. It can open doors and opportunities.
  11. 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 who I see consistently attend meetings and networking events are the people who I end up doing business with. It shows that they care about the community as much as I do, and I appreciate it more.
  12. There needs to be something better than Starbucks to meet people. If I didn’t have an office, I would pay a monthly charge to a coffee shop that gives me access to a private room with computer / project setup and coffee. I’ve had this idea for ages, please someone do this.
  13. 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?
  14. Rapportive is an absolute life saver. Seriously, it’s amazing. It’s a chrome extension for Gmail that gives you detailed information about somebody just from their email address. It’s super simple and super effective. I use it to pre-stalk the people I’m going to meet.
  15. There is no easy way to track people after you meet with them. I would have loved to have some simple dashboard interface that allows me to see the progress people have made since I met them. I imagine it would integrate with my calendar and give me summary highlights of everyone. I keep up with people by randomly seeing them at events, saying hello over email, etc. As I said before the people I follow-up with the most are people who show up to the events. There are some software products that reminds me when I haven’t emailed someone in a few weeks. I couldn’t care less if I havent emailed someone in 2 weeks. That’s not what I care about. I want to see how they are progressing and what they are working on. I dont’ know how this could be done, but it would be amazing.
  16. Being connected has its perks – Being connected in any community opens a lot of doors. The type of people who I would never have access to a year ago, are now people who I talk too often and I get a better response rate on my cold emails.
  17. Yes, coffee meetings can be a huge waste of time – I don’t take coffee meetings to make it feel like I’m actually busy. What I’ve done in the past 400 days is not sustainable. I think what I did was necessary to build my personal platform in Chicago, but not necessarily the best route for me to take going forward.

Overall, the past 400 days have been amazing and I don’t regret taking that many coffee meetings. It’s one of the best decision’s I’ve ever made.

PS: Read the only resignation letter template you’ll ever need.