A Little Love Can Go a Long Way

Danielle Gillespie
3 min readAug 2, 2022


For startups, a little meaningful love is way better than a whole bunch of superficial like.

I founded a company a while back and as we started to think about sales, our first goal became to onboard a handful (20–30) of paying customers who loved us.

It took some time but eventually we onboarded many customers who truly loved us. I know that they loved us because they were recommending us to their professional peers and sending unsolicited five star feedback.

Unfortunately, we ended up being a covid casualty and while the outcome wasn’t great, it was was a graceful conclusion. When the time came to wind the business down, I knew we had truly created something special because many of our customers stepped forward offering words of encouragement and in many cases, spearheading personal efforts to help us keep the product alive. My customers were on my team and had my back.

One particular customer from those early days has always been a personal favorite of mine. The client was a challenging prospect and frankly I was afraid to close the sale. But, once on board they have been my most committed and loyal fan. They even went so far as to try to find other investors, buyers or at least more customers to help us persist.

My Bedside Manner Sucks

So how did it happen? I’m not completely sure how we ended up with such a great set of clients but I do know that every single interaction had these elements of genuine interaction:

  • Listen: I listened to prospective and current customer concerns, what they were saying and also what they were not saying
  • Respond: I responded to the feedback without bias
  • Treated like a human: I treated each client like a human who had something valuable to say
  • Honest: I was honest even when I did not want to be
  • Overdelivered: I gave them more than they were asking for as often as possible

It cost nothing more than a little bit of my time to make my clients feel important and understood. There are many companies that put customers first and those companies have very loyal followings. Love and loyalty cannot be underestimated and is frankly an objective that we do not talk about enough.

Why was our mission to get a handful of customers who love us?

Honestly, it was probably just dumb luck. I was looking for a way to talk to investors about the group of paying customers that we had on-boarded. I was insecure because the numbers were low but then while talking to one of my advisors I realized we had built something pretty cool.

Later I learned that I’m not alone in embracing this way of thinking. In this Inc Magazine article, Brian Chesky shares the following, “The best piece of advice I ever got was from our first investor, Paul Graham. He said it’s better to have 100 people love you than a million people that sort of like you, so if you can find 100 people that love your product — as long as there are more people like them in the world — then you have an idea that I believe will spread around the world. But if you can’t get 100 people who absolutely love your product, then you do have a problem.”

Getting Started

If you’re just getting ready to launch or if your product is already in the wild, you can always focus on finding the customers who love you. A few simple things you can and should be doing:

  • Collect usage stats to see how and when people are using your product
  • Find power users and talk to them, give them stuff and engage them — they will be an important referral network and will help shape subsequent product versions
  • Get blind feedback and ask good questions
  • Ask your customers what are the three most important things your product provides for them
  • Measure love
  • Get to 100 customers who love you

In collecting user data and feedback, you may find that you’re already more loved than you think!

Feel free to share your love story in the comments.



Danielle Gillespie

Defining the intersection between technology and human connection (I also help entrepreneurs build rock solid tech products: daniellegillespie.net)