Health-tech CEOs reveal their storytelling secrets

For my book, The Storyteller’s Advantage, I interviewed dozens of CEOs about how they developed effective narratives - and what you can learn from them.

I recently met with a founder who described the success of a larger competitor in the following way: “We have a better product. But I guess they were better at telling the story.” 

That comment was meant to disparage the competition, as little more than smoke and mirrors. But the ability to tell a story is a highly effective - and often underestimated - business strategy that should be praised, versus undermined. A good story can get any team well on their way, and it’s extremely challenging to compete against a company that has strong awareness in the market plus a strong product. In those all too rare cases, I’ve personally seen companies grow from being small startups to achieving escape velocity. 

Over the past five years, I’ve spent countless nights and weekends working on a book about the secrets of the best storytellers in business. I wrote the book through two births and postpartum periods, and I edited it on countless subway rides or hovering by the tub while my kids took a bath. The book is so important to me because I genuinely believe that healthcare entrepreneurs (and, really, all entrepreneurs) have the odds are stacked against them. And I know deep in my bones, from 15 years of interviewing founders and business leaders, that storytelling matters and can give them an edge.

Good storytellers aren’t just effective at winning media attention. They are also more adept at hiring and recruiting, at sales, and at raising investor capital. Storytelling catalyzes all the important business processes because humans are not objective beings that are driven by numbers and statistics. Our brains process information and retain it through stories. Neuroscientists have proven that via countless studies. I spoke to many of them in the process of writing the book, who confirmed that even in an era of AI.

So how can you learn from the top storytellers, and apply it to your own company? Well, I would first invite you to pre-order the book. For authors, that means the world and it’s especially important to give the book lift in the early days. But if you’re more of a CliffsNotes person or you need to read more to be convinced (your time is extremely valuable), then I wrote a preview for you of five lessons from the book. Several of these feature storytellers in the health-tech industry, although I chatted with CEOs across entertainment, retail, consumer, technology, sports, and more. 

1. Don’t forget about the underdog 

I can’t tell you how many times I’ve heard companies describe themselves as the “leader” of a category they essentially made up! While being the leader might be strong positioning for sales, there might actually be some downsides that aren’t discussed enough. Think of the tale of David and Goliath - a story has been shared countless times, and while Goliath might have been slated to win the fight, very few people would have been rooting for him at the time. Consider every good sports story ever told. We’re all searching for the magic moment when a team of players manages to pull off an upset that rocks the world and changes the face of sports history. Psychologists have studied this fascination with the underdog, and found that the human brain is wired to support the contender who isn’t the favorite.

The tactical takeaway: For the startups out there reading Second Opinion, consider positioning that involves being an innovator taking on an incumbent or group of incumbents. That lets people root for a company and rally around the idea that their success will make the world a better place. One good example from health-tech is PillPack, which got a lot of press related to its battles with companies like Surescripts. The press reported both sides, but many people in the industry sided with PillPack, viewing their battle as being linked with the struggle to liberate patient data. There might also be opportunities to toggle between two messaging strategies - to be a leader in one arena, and an underdog in another. I believe the ambient AI scribing companies have that opportunity now - they might describe themselves as a leader in solving physician burnout, but also take a stand against a larger player like Epic as it encroaches on their market.

2. Build up the founder story, but don’t forget about everyone else

The founder story is one of the most powerful storytelling assets out there. We are collectively fascinated by it. What drives that individual to take on a massive personal and professional risk to strike out on their own and solve an intractable problem? The founders I admire most from a storytelling perspective can relay the founder story in their sleep, and they know how to tweak it for the benefit of various audiences. One of my favorite examples in health-tech is Glen Tullman’s story of how he started Livongo, which was sparked by his son’s diagnosis of Type 1 diabetes. 

The tactical takeaway: The founder story is powerful, but there is a key person risk associated with it. What happens when that individual steps down? Who else After Livongo got sold to Teladoc and Tullman stepped away to start a new business, how could the company enter into a new era without him? Who can tell that compelling story that fuels sales in a crowded market? With billions in market value wiped out since the acquisition, that may have indeed been a challenge. One potential solution is to get the voices and opinions out there for others in the organization, without forcing them to compete with the CEO. For instance, take someone like Brandan Keeler, who is an interoperability lead at HTD Health. Keeler does a lot of writing, public speaking, and other forms of content about what he knows best (interoperability, APIs, portability of data, health data policy), and in ways that are entirely authentic. What other individuals in the organization could build their own followings about their areas of expertise, and in the forums that feel natural for them?

3. Use storytelling to raise capital 

Aside from writing this newsletter, I do occasionally work with companies on their fundraising materials and strategy. For companies of all stages, but particularly early-stage, it is imperative that they use their deck to tell a story that builds. A lot of founders make the mistake of trying to tell their whole story in a single slide, which becomes incredibly crowded and hard to read. There should be a framework that starts with the vision and mission, flows into the problem to be solved, dwells on the solution, and runs us through a future where the business is successful. The numbers matter, but investors aren’t purely objective; there is also that like-ability factor that compels them to lean in. 

The tactical takeaway: The classic narrative arc known as the “hero’s journey” is one that every founder should familiarize themselves with before they raise money. On page 243 of the book, I walk readers through how Kate Ryder tells the story of Maven Clinic, and how investors related to it. Investors aren’t interested in a story of linear success, and rarely will they believe it. Founders should be willing to describe how they overcame obstacles, and how those struggles made them far more effective than they would have been otherwise. Most startups fail; so investors are looking for evidence that a founder won’t throw in the towel, but will do what it takes to make the business successful. For early-stage, grit is everything, and that quality can be teased out through powerful narratives.

4. Be honest and direct, especially with journalists

I can’t tell you how many times I see companies trying to treat journalists like corporate mouthpieces. But journalists are motivated by the needs and wants and interests of their own readers (the public interest), versus what a company would like them to say. For that reason, the official messaging can often fall flat, because a journalist is smart enough to see through it - and the company won’t answer their questions. That can motivate a journalist to look deeper on their own, which breeds distrust on both sides. 

The tactical takeaway: I have rarely seen much downside in cases where founders are open and honest about stumbles and challenges. I highlighted two health-tech examples in the book. One from Alex Benson, who took over as CEO of a company called Bardavon in 2024. At that time, he chose to write a public post highlighting the shifts in the operating model, even noting some missteps that were made in the past to chase shiny objects versus focus on the core product. “Like others before us, we stumbled here,” he wrote in a LinkedIn post. Likewise, when Brightline, a kids’ mental health company, made a decision to make a layoff of employees and shift the business strategy, she wrote a refreshingly honest post about the change in business model. And she offered to help those who had been impacted by the cuts find new roles. Her post garnered thousands of views, dozens of positive comments, and no negative commentary in the press.

5. Communications leaders should not report to marketing

I spent a lot of the book writing about how communications leaders are not in the right part of the org chart. Those that report to marketing are focused on generating leads from the sales team, which is primarily in the form of clicks and attention. Those that report to the CEO can be far more effective, working across the entire company to bolster not just the brand but the reputation of the entire team. They can take more risks, and they can focus on more than just generating fluffy media stories. And that, in this climate, is basically an impossible job, given every day there are new layoffs in mainstream media. 

The tactical takeaway: Put comms under the CEO, and change their responsibilities to building influence with target audiences via direct channels, building relationships with the media (not just their own, but ensuring the CEO also has those connections), using internal communications to help create a happy work culture, and more. I spent a lot of time in the book describing how media is changing. Bottom line: News articles won’t drive much in the way of clicks anymore. What matters is brand and reputation; and that can drive an entirely new type of marketing that is far more powerful than spending millions of dollars on Facebook ads. 

If this piece resonates with you, I’d love it if you bought the book. I’ll be doing more events in the coming weeks to talk about it, so if you’d like me to participate in one, please don’t hesitate to reach out. I care very deeply about this topic because healthcare in particular needs its storytellers. This is a very tough market to succeed in, so founders should leverage every tool in their arsenal - and this is a very powerful one! Thank you for reading.

Want to support Second Opinion?

• 🌟 Leave a review for the Second Opinion Podcast
• 📧 Share this email with other friends in the healthcare space!
• 💵 Become a paid subscriber!
• 📢 Become a sponsor