An Entrepreneur’s Humanity

Jeffrey Osborne
3 min readNov 25, 2021

This is a story about someone named Aaron.

As I once again find myself in the early customer discovery phase of a new venture, I spend a good chunk of time reaching out to people across industries trying to learn about their problems. Cold outreach is still a big part of my customer discovery process. And let’s be honest, cold outreach can be frustrating. In early ventures you really have no idea what you’re doing. You want to solve someone’s problem, but you don’t know what the problem is (or worse, you think you do). You are told to get out of the building to meet customers, but every time you go outside you get the cold shoulder.

I’m not the right person to talk to.

We have a solution for that.

Reach back when you have something.

I’ve heard all the excuses. These excuses are understandable; why spend time with someone who has nothing to offer?

So what does Aaron have to do with this? It’s because he took my call.

Favors In >> Favors Out

I’ve met Aaron’s before. They are fellow entrepreneurs that will give you their time for no benefit to themselves. They take your call because, as Aaron said in ours, they’ve been in our shoes. They are repaying some long ago received favor. People like Aaron have an internal counter of favors received and favors given. The former always outweighs the latter. Not with ten lives could I repay all the favors I’ve received, and certainly not to those who directly gave those favors. My only hope in repaying those favors, as Aaron realized, is to help others.

Most people enter entrepreneurship because they are techies. They want to build really BIG and cool things. The most surprising thing about entrepreneurship though is discovering humanity along the way. I believe that entrepreneurship is the most human of professions. You are in the business of solving problems for others, problems which are oftentimes unarticulated and undiscovered. As an entrepreneur, you are obligated to understand the ambitions of others, their challenges, and their constraints. It takes immense empathy to be a successful entrepreneur.

Perhaps this is why entrepreneurs, more than any others I’ve seen, will respond to a cold outreach. They see that glimmer of a younger (and certainly more naïve) version of themselves and instinctually empathize. The Aarons of the world think back to when someone helped them out, and feel an obligation to repay that favor.

An Accidental Thanksgiving Story

I had this story in my head for a little while, but only decided to put it into words purely by coincidence on American Thanksgiving. As a proud Canadian who’s Thanksgiving has long passed, I think it nonetheless befitting to tie this story somewhat to the holiday du jour.

I’m thankful for the entrepreneurs like Aaron. I’ve met hundreds, if not thousands of them. People that will give you their time for no reason other than perhaps some cosmic karma counter they are trying to right. I believe this built-in culture of paying-it-forward is what makes entrepreneurship the world’s most impactful profession, and certainly something that makes it enjoyable.

To the countless people that have given me their time, thank you. I can never repay those favors to you, but I’ll do what I can to pass it on.

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Jeffrey Osborne

Engineer turned business development guy. Passionate about the space economy, disruptive innovation, and sustainable corporate strategies.