The 1 Question To Ask When You Meet Fellow Bootstrappers

John D. Rockefeller once said “A friendship founded on business is better than a business founded on friendship.” I could probably find a few dozen more quotes that higlight the fact that connecting with people around you is a sure fire way to increase your success in business.

But I'd rather show you a way beyond traditional "networking" and tell you about how I discovered the one question that changed how I do networking.

Networking > Exchanging Business Cards

The first steps young entrepreneurs (me being no exception to the rule) usually take down that path are:

  1. get fancy business cards
  2. Go to "networking events"
  3. Exchange business cards
  4. Wait for spam in your inbox

I learned one important lesson:

Superficial "connections" get you nowhere – friendships matter!

After I learned that lesson, I knew that I had to change things around.

What I am doing different now

So instead of trying to meet as many random people as possible in 2 hours of "networking", I now focus on having more contacts with the same people. And you know what? That (for me) is actually more fun. I don't like meeting 50 people and forgetting 49 names instantly. I enjoy spending an hour (or four) with truly inspirational people over dinner or a coffee.

This gives you way more time to actually talk about interesting stuff – instead of trying to memorize names and exchanging pleasantries – and getting to know each other.

The Question That Makes People Scramble For Words

A while back I was travelling to Victoria, BC, Canada and while I was in town I managed to have coffee with Matthew Lehner – a fellow bootstrapper. After about an hour of covering topics ranging from places to see around the area to consulting gigs to building a SaaS application, I asked him one very simple question:

"How can I help you?" – and what followed were at least 30 seconds of silence 🙂

Matthew – never having been asked that question before – just didn't know how to respond to that. We are just not used to someone being sincerely interested in helping you.

It's a bit like customer service: The bar for good service is so low, that it has become ridiculously easy to stand out of the crowd. The same is true for networking: Put the other person first, try to actively help him and you are on a good track to making new friends.

Matthew even followed up with the following tweet:

Just had coffee with @itengelhardt. He asked "What can I help you with?" My response: "derrrr.. never been asked that before.."

In the same conversation he later concluded:

I feel like asking that might be a cheat code for life.


Hell, YES, Matthew! That is spot on! I didn't know it up to seeing his reaction, but it really is a cheat code. It immediately tells your fellow bootstrapper, that you genuinely care about him (You of course have to mean it…).

Please, go out and use this hack. I have made it a habit since to ask every founder I meet the very same question: "How can I help you?" – You wouldn't believe how happy they are just to hear those words! It works even better, if you can help them by giving feedback, buying their product or connecting them to other people you know.

PS: Another awesome idea (that I haven't tried yet) is the "Help Me Help You" dinner. I have not the slightest doubt, that it is well worth imitating – and it limits the number of names you have to learn in one evening. 🙂

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About Christoph

Christoph lives in Munich, Germany and is bootstrapping his own SaaS application as a part-time entrepreneur.

He likes to write on this blog about anything of relevance to single-founder bootstrapped software startups.


  1. See, when I was growing up, we called this "making friends"… it seems this now that this concept appears to have morphed into some semi-superficial "network relationship" where we all are only doing stuff for others in order that we may get something beneficial out of the deal… like connections with your friends or some kind of returned favour.

    Whatever happened to making friends with someone just because "Hey, that shit you're doing looks like a ton of fun, let me get in on that with you and maybe we can make it even more awesome together!" or "Hey, you're awesome and I wanna hang out with you!"

    I think I'll continue networking the way I have since I was 5… because all this sociopathic inability that people have to actually connect with other people as soon as they're "in a professional environment" is tedious.

    • Christoph says

      Hi Ben. 

      Thank you. I appreciate you writing such a lengthy comment.

      I might not have made that clear enough (and the intro to the article is confusing in that way, too): I am not looking for a return (besides having a great time) with this.
      I started out going to networking parties, because I was told that it was the way to go in business. I didn’t like it and have since changed the approach to something that makes me happy. 

      This being said, we are both aware of the fact that being helpful will eventually have benefits for you (reciprocity).



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