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How 50 Cups of Coffee Can Change Your Life

Raising investment, changing careers, or leaving your city? Then you owe it to yourself to have coffee with 50 people.
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Each time I make a significant change in my life, I have coffee with 50 people to get their views on my plans.

If you’re raising investment for a start-up, changing careers, or moving to a new city, then you owe it to yourself to have coffee with 50 people before making the jump.

Setting the goal of having coffee with 50 people forces you to be clear about your goals. Making the goal public, one person at a time, also makes it much stronger. Having 50 coffees is good because then you have to commit to the specific move that you want to make. You’ll also get input from smart and interesting people.

50 people could change your life

I first came across the idea in the book, What Colour is Your Parachute?. More recently, Mark Suster put a number on it in his article, Why You Need to Take 50 Coffee Meetings. Until then, I’d just aimed for as many coffees as needed until I had gathered enough input to act on. Now I aim for 50 because it simplifies the process, makes the goal concrete, and is large enough to be a stretch target.

Megan Gebhart became a bit of an Internet celeb and travelled the world meeting new people for the 52 Cup Project. She was inspired by a quote from Charlie Jones: “You will be the same person in five years as you are today, except for the people you meet and the books you read.” 

The hidden insight in the 50 coffees idea is that the biggest changes in your life will only happen through the people that you meet and conversations you have. Human beings create and convey meaning through stories and conversations. If you change the conversations that you’re a part of, then your life changes automatically.

Who to get coffee with

This isn’t 50 coffees with complete strangers. The coffees will be mostly with friends and existing acquaintances. You know that favorite former colleague you keep meaning to catch up with? Now is the time.

Mutual introductions are good. Think one degree of separation. Ask your friends, investors, clients, and colleagues if they know anyone interesting you should meet.

Having coffee with a purpose but without an ulterior motive has made me more confident about meeting new people. I still get nervous about asking someone new for coffee, but I’ve met great people and made some real friends.

50 coffees are worth it

I had 50 coffees when I left law for design. I did it again when I moved to London, and most recently when I published a book. The 50 coffees idea has worked so well for me in the past for these reasons:

My best ideas always come up during a heated conversation. My brain seems to be wired up to my mouth--not always a good thing--but it means that I think better when I’ve got a smart conversation partner to debate with. (Caffeine is great fuel for conspiracy.) For any big life change, there are people out there who have already done what I’m thinking of doing. I can get more from their anecdotes than any book, blog, or article.

To get more input, I try to meet people who have very different backgrounds than mine. I'm not talking about generic catch-up coffees and awkward first-time meetings with sales prospects. Instead, I'm looking for a focused debate with an intelligent peer. The best coffee discussions are about an idea you’re both interested in, or where the other person can give you input on something they like discussing.

Make the most of the coffee

The focus on a real project or issue is what makes this coffee different from just catching up. Instead, you’ll be conspiring, debating, and swapping stories. Being specific about what you want to talk about will make the coffee feel much more valuable. Here's what I've learned: 

Be intentional and focused. Keep the coffee under 20 minutes. I usually meet people at their office and use the walk to and from the cafe to get the conversation going. 

Be honest about what you want. Tell the other person upfront that you want their input on a big move.

Don’t ask for anything. Let the conversation be the value. No selling, no pitching, no interviewing. The other person’s time, advice and story is all that you can ask for in a short coffee meeting like this. 

Think ahead. Formulate five to ten questions in your head that would be interesting for the other person to answer and that would help you triangulate your problem.

Take notes. A general chit-chat will be lost in the sands of time. For your 50 coffees, you should be taking notes because it shows you’re there for a reason and it’ll help you find common themes. Bring a small Moleskine notebook.

A small tickle can be good before asking someone to coffee. Stef and Paul from the start-up foundry Makeshift add people to a Twitter list like, “We should meet” or “Would like to chat." You can do simple things like follow the other person on Twitter or favorite their tweets. Don’t overdo it and add the other person on LinkedIn before even meeting them--that's a bit too forward. Still, it's nice to make some sort of connection in advance.

TIP: Don't waste people's time

Having coffee is contrary to a lot of the popular start-up buzz. Many investors and consultants are sick of getting coffees with strangers who waste their time. Rob and Sal from FounderCentric and LeanCamp invented Startup Burger Nights to avoid coffee meetings, and I know of several London investors who use the “just grab me at Silicon Drinkabout” line to dodge coffee. 

These days it's hip to be unavailable, which is fair enough, but your 50 coffees shouldn’t be the type of banal, time-wasting catch-up that people avoid. You should make the experience fun, easy, and productive.

TechStars mentoring coffee

Coffee meetings are easier in a connected context like the start-up ecosystem, but you can meet anyone if you ask politely. My trick is to watch the other person’s drink. When they finish their coffee, the meeting is over. The theory is that if they’re enjoying the discussion, they’ll be too engaged to drink their coffee. We all reach for our glass in a moment of awkward silence or when we’re bored. Their coffee cup is your hourglass.

TIP: Never steal time

If the other person gives people advice for a living (think consultants and creatives), then don’t ask them for advice on your problem. Instead, just absorb their way of approaching it. Ask for war stories of interesting projects. Ask about how they got started. Let them talk about what they’re interested in.

How to get coffee with anyone

There are lots of ways to ask someone for a coffee, but I like to keep it simple:

Pick a good place. Think from their perspective and offer to meet at a high-quality independent cafe close to their office. I’m lucky because my blogging for The Coffee Hunter takes me to cafes all over London. You can use FourSquare to find a good place that’s close to their office.

Make it a good time. Some people like to do quick meetings in the morning to get them fired up. Others prefer a regular morning coffee or quick lunch. The Brits like "stopping for just one" on the way home from work, and that can be a good time to meet people. The most important thing is that it suits them.

Be interesting. Figure out what they are working on or would be interested in discussing. Put that in the first email.

Be direct. Put the invitation in the first line of the email. The preamble stuff is nice, but don’t bury the lede. 

Tip: Travel for coffee

People crave novelty, so ask for coffee with a local when you travel. I’m now in London and would love to have coffee with someone who has just arrived from New Zealand. Likewise, when I was in New Zealand, I would have been happy to hear from someone who had just arrived from London. Even if you're on vacation, you can always put on your nice jeans and T-shirt to ask a local for coffee.

My next 50 coffees

My next move is to get back into consulting with companies in innovation and social media. I’ve loved working with start-ups in London, and will continue to work with the start-up scene through Converge and the Innovation Warehouse. But now it’s time for the next phase of my career. I’ll be reporting back on the coffees that I have along the way.

This post was reprinted with permission from the digital brand strategy blog, PeterJThomson.com

IMAGE: Courtesy Peter Thomson
Last updated: Sep 13, 2013




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