How to Tell Your Story With Authenticity and Watch Investors, Customers and Talent Come Pouring In

There’s a YouTube channel I love that charts a man’s mission to hike around the world. He’s been at it for a couple of years now, and one thing I appreciate, in addition to the amazing landscapes and diverse cultures he encounters, is seeing the difficult side of his journey. This isn’t a regular travelogue where you only see the highlights — picturesque hotels, perfectly poured plaza-side beers, jaunty hiking outfits. Those things happen, but they’re occasional.

More often than not, his followers endure his tribulations along with him. More than once, I’ve felt a deep pang of empathy when the trail gets washed out after heavy rains, or when he wakes up in a frigid tent on the third day with a nasty bout of flu. It can be easy to glamorize something as romantic-seeming as a hike across multiple continents; to edit out the pain and document only the glory. But he doesn’t. His followers get it all. And on those days when things go well — a surprise home-cooked meal, a glorious vista — those of us watching feel like we’ve won, too.

Founders face a similar choice with how we tell our stories. It would be easy enough to paint a picture of everything going well, just one straight line of continuous growth and progress trending up, up, up. The problem is that it’s not real — and more importantly, it’s not interesting. Here’s how to tell your story in a way that will actually resonate with people.

The case for vulnerability

Not long ago, businesses were accustomed to speaking in absolutes, even if their claims were obviously false. Peruse a newspaper from the late 1800s and you’ll find no shortage of advertisements for everything from pills that promised to cure rheumatism, toothaches and cancer to electric belts that guaranteed “complete restoration of health, vigor and manhood.” Clark Stanley’s Snake Oil Liniment claimed to be a miracle cure — until it was tested in 1916 and found to contain nothing but mineral oil, beef fat and turpentine.

We’ve grown more skeptical of such promises, yet the impulse to present a flawless image persists. Leaders have long felt they needed to project unwavering confidence and never show doubt. Admitting struggles felt like admitting weakness.

But research increasingly shows the opposite is true. Gen Z in particular “distrusts overt persuasion,” the LA Times reports, instead prizing transparency and penalizing corporate-speak. As a result, brands are focusing on “unvarnished narratives” like employees talking about the process of product development, user-generated testimonials and influencers who share their genuine experiences, good and bad.

This push for more vulnerability isn’t just true of brands. For founders, sharing the ups and downs of their journey can be a powerful way to garner community and attract loyal followers.

The fine line between authenticity and oversharing

There’s an important distinction between being transparent about the trials of running a business and plain old whining. The difference comes down to purpose: Why are you telling this story, and who benefits from hearing it?

Social media is a breeding ground for a certain type of oversharing. I follow an old colleague on X who is constantly posting about their poor luck, blaming everything from the market to Mercury in retrograde for continually losing clients and seeing their business underperform. They sailed past “vulnerable” and entered the darker territory of “hard to watch.” Worse still, they come across as unreliable, and I have to admit: I wouldn’t hire them.

Before you share a difficult moment from your journey, ask yourself: What can others learn from this? How does this help someone else navigate their own challenges? If the answer is “it doesn’t,” you might want to reconsider hitting publish.

When I share stories about Jotform’s early days — living with my parents while building a product I released for free, or spending entire days recovering from database crashes — it’s because I’m trying to normalize the messy reality of building something from scratch. I know how easy it is to construct a fictional world where everyone else seems to be enjoying an unbroken winning streak, and I want other founders to know that uncertainty and setbacks aren’t a sign of failure. They’re just part of the process.

The dos and don’ts of authentic content

How you tell your story matters just as much as your intention. One habit I developed early (and still do today) is posting on forums where I can be an engaged part of the community I want to reach. I was a coder long before I became a founder, and I still love sharing tech insights with readers on platforms like Reddit and IndieHackers. By the time I released the first version of Jotform, I was deeply ingrained in these community forums, so asking people to try it out didn’t feel overly promotional.

Being authentic also means knowing where to draw the line. As Tomas Chamorro-Premuzic points out in Harvard Business Review, the key is having the psychological maturity to “recognize that just because you feel like saying something does not mean you should.”

In other words: Do share genuine stories about your journey when they’ll be helpful to others. Don’t overshare or convey yourself in an unflattering light for no reason, or when what you’re sharing is unnecessary, inappropriate or simply unhelpful. You don’t need to bare your soul with every post or video. Instead, the goal is to shed light on the path for others — showing them the washed-out trails and frigid mornings alongside the glorious vistas, so when they face their own challenges, they’ll know they’re in good company.