Why Telling a Story Matters


The title of “storyteller” has always conjured up a very specific emotion; it’s nostalgic and comforting. I always get the oddly specific mental image, of sitting in a Barnes and Noble children’s section, listening to someone read from a picture book. I don’t recall ever attending more than one event like that so, I’m not quite sure why it beats out listening to my parents read Harry Potter but, that’s beside the point.

This fascination with “storytellers” stirs childlike wonder, but is often left behind with that specific part of our life. Today, however, the rise of professional “storytellers” can be felt all around us. People make their living telling stories as freelancers or for fortune 500s!

Look no further than Branden Harvey, storyteller extraordinaire. Branden took up photography early in his life and his work propelled him to incredible heights. Yet at the peak of his renown as a photographer, it became evident to him that it wasn’t the actual act of taking photos that he was drawn to; it was the chance to tell a story. With that, he shifted his focus, becoming a trusted advisor and hire for some of the world’s biggest companies, who need to tell a story. Not only that, he now runs a company dedicated to sharing good news stories from around the world!

Not bad, right?

The thing is, each of us needs to embed a little bit of storytelling magic within our own businesses.

Your business is an extension of you. Something all creative entrepreneurs need to understand is that you are primarily selling yourself; you just so happen to be offering a product or service as well. In order to build trust, the way you sell yourself has to be intentional. The best way to do that is by learning how to tell your story.

So how do we present a story to our audience in a way that matters? How do we become storytellers?



Decide Who You Are

Let’s start with small steps. Essentially, you need to decide who you are and what you stand for. How is that is going to be woven into the fabric of your business? Your business is an extension of you, thus, having a clear and defined sense of self is crucial. The best way to do this is to keep it simple.

You should be able to articulate your sense of self or mission statement in one line. Dubsado is the ultimate client management system for the creative entrepreneur. Simple and easy to understand. We've identified who we are, what we do and who we are for. You don’t need to follow this formula exactly, but it helps give a sense of the simplicity you should strive for.

What is it that you are trying to do for others? Where have you come from that makes you the person qualified to do this? Why are you, more worth following along than anyone else? That is your story and where you’ve come from informs that.


Become Excited About Who You Are

I love this one. Once you decide on who you are...become excited about that! People hate to feel like they are being sold a product. An easy way to make the sales portion of entrepreneurship feel less uncomfortable is to make it about selling your own excitement about your story.

I was talking to Jake (Co-Founder of Dubsado) once about the first ever hiring event we attended for Dubsado. At the event, the two of us tag-teamed interviewing some of the most talented programmers around. I know absolutely nothing about computer programming, so Jake obviously talked technical skills and I found myself conveying the heart behind the brand. I talked about the kind of people we are empowering, the stories we hear from our community and why what we were doing goes so beyond software. While sharing his thoughts on that experience, Jake said something I wasn’t expecting. He said that listening to me talk about Dubsado at that event, a program HE had created, was the first moment he truly fell in love with his company.

It isn’t because I love Dubsado any more than Jake does. It was that hearing someone else convey such enthusiasm and genuine passion about what he had built was a turning point. He didn’t need to coach me on that enthusiasm. I didn’t have a script. I was just being honest about a story I was pretty excited to be a part of.  

We found quickly became popular at the event, though we were amongst some of the biggest fortune 500 companies around. We were doing something different. We were genuinely excited about who we were and were offering the chance join that story. To help write the narrative.

Give your potential clients the chance to be a part of your story, by being excited about it yourself.


Be Vulnerable

When social media is clicking, it’s because it’s being leveraged as a platform of genuine connection. Often, the quickest way for that genuine connection to occur is through vulnerability.

People will pick up on fabrication. They will know if you are trying to pull vulnerability out of thin air. If you are trying to put on an appearance. They’ll know if you’re following a script or following the same old social media rules. They’ll also appreciate true, genuine vulnerability and believe in your story all the more passionately.


We’ve talked a lot about the difficulty of the entrepreneurial path, but the amazing part is that if you embrace the power of vulnerability, the difficult points of the journey can become your most powerful storytelling assets. It’s a win-win for you! If something bad happens, that’s ok!  You are able to add new and unexpected chapters to your story. Ones that reminds people that there is a normal person behind the business! Go figure!

One of the things I love most about Dubsado is how much the community has come to trust the authenticity behind not only the co-founders, but the whole team! In an era with so many startups and corporations rushing to hide their phone number as soon as they can, the simple act of having a face to the name creates connection. Even more so when that face is candid about the ahrd times. That’s good storytelling.


Look For Similar Stories

You’ve worked hard, followed these steps and are proud of the story you are crafting for yourself. You still haven’t gotten to the best part. Storytelling comes to life once what you have created finds an audience that it resonates with. People who see themselves in your journey and value that a connection exists. This is when you should start building community.

The story doesn’t end once you think you’ve figured yourself out. Community adds a whole new dynamic. A chance to share your story with more people, a chance to expand upon your own because of the ones they share and so much more.

Communities spring up around common interests, goals or characteristics so having a well defined and genuine story helps to foster more meaningful connections with the communities around you. Whether it’s online or in person, don’t keep what you’ve gone through to yourself!


A good story can be the difference between a good and great business. It can have numerous rewards, financial and beyond. My favorite thing though, is the idea that somewhere, someone may be hooked on our story. They might be where I was not too long ago. Who knows what guidance your story could provide. What strength your vulnerability will pass on. And what loyalty you may foster, through simple storytelling.