Better Storytelling for Startup Founders

I love all things data. But when I transitioned from software engineering to sales, I had to ditch the numbers.

Don’t get me wrong. Numbers are obviously critical for sales when setting prices, tracking revenue, and paying out commissions. When it came to speaking to customers though, I had to learn to lean less on the facts and rely more on the story.

As an engineer, I planned everything in excruciating detail. My presentations were full of architecture diagrams, code examples, and hard data. I scripted the entire pitch. I ensured the demo was rock solid. And I made sure to never veer from the script.

As a famous boxer once said though, “Everyone has a plan until they get punched in the face.” I took plenty of punches in meetings. Customer were not interested in sitting idly, and would deliberately fling questions at me, interrupt my demo flow, and pepper me with endless needs not addressed in my pitch.

I thought this was annoying and rude. Then a much more seasoned sales executive took me aside and told me that my customer pitch sucked. I did not listen to customers. I was abrasive when questioned. I ignored signs of disengagement. My most critical mistake though was that my pitch had no story.

I did not understand the cardinal rule of effective communications. It is more than just the transmission of information. To be effective, the information being communicated must be clearly understood. That requires understanding how people consume the information being conveyed.

Science has confirmed that stories are the best vehicle for learning and influencing others. Research suggest that facts are 20 times more likely to be remembered when delivered in a story. This is due to how humans process information, where more factual data only activates the language center of the brain whereas stories activate multiple areas. This releases the hormone oxytocin in listeners, which increases their empathy for the person sharing the story.

I did not turn around my horrendous pitching habits immediately. I had to become a better listener, do more upfront work to understand the needs of the audience, and get better at handling objections. Only then could I give more consideration to this idea of storytelling.

So how did I get better at storytelling? I had to completely invert my perspective from what I wanted to say to what customers needed to solve. In other words, start from the customer and work backwards to address what they are interesting in hearing. As Dale Carnegie once said:

Next, I had to discard my crutch of relying on knowledge, data, and facts. This would carry over into the slides I presented, which were eyecharts of information. Those things are still important, but they have to be weaved into a bigger narrative to become memorable.

Last big shift was to learn the art of crafting a compelling story. The key to any good story hinges on the element of change, one that is meaningful enough to provoke attention. This was the key to helping me pull together a story connecting what the customer needs to the solution I was proposing. That was the element missing in my pitches, the big scary change that we were best positioned to solve.

Years later and after many presentations, storytelling is much more natural to me. As I review startup pitches though, it is clear that many founders struggle to tell a clear, compelling story. They are stuck in the land of facts and figures.

To help you shift from a fact-teller to a storyteller, here are 10 practical tips to consider when pulling together your pitch:

1. Define Your Narrative – What's your "why"? Identify the heart of your startup's story. Is it about solving a problem, a personal journey, or a vision for the future? Identifying your why will be the foundation of your storytelling.

2. Develop a Narrative Structure – Organize your story with a clear beginning, middle, and end. You want to start with your “why”, describe the journey, highlight how it ties to your solution, and the summarize to help your audience connect the dots and make your “ask”.

3. Incorporate Storytelling Elements – Are there heroes and villains in your story? Great stories utilize elements like conflict, resolution, and redemption to create a compelling narrative that leads your audience into wanting more with each slide and transition.

4. Make the Language Lively – This is not the moment to be humble. Use vivid descriptions that paint a picture with your words to help your audience to visualize in their minds the story you are telling.

5. Be Authentic – The idea of “fake it till you make it” is dead. Never fabricate or exaggerate as it is easier than ever to smell a fraud. Instead, be vulnerable and share your struggles, failures, and triumphs. Authentic stories resonate deeper and build trust.

6. Know Your Audience – Tailor your story to your audience. Investors care about the market & big returns, employees want to know culture & vision, and customers need to understand how you solve their problem. Remember, your pitch starts with the customer in mind!

7. Show, Don't Tell – Use vivid anecdotes and examples to bring your story to life. Show the impact of your startup’s solution through real-life scenarios, “day-in-the-life” demos, customer testimonials, or personal experiences.

8. Keep It Simple – Write down all your ideas, then edit ruthlessly. This is because the brain hates complexity. Simplify your narrative down to only the most impactful elements that capture the essence of why your startup is unique and special.

9. Evolve Your Story – As your startup grows and scales, so should your story. Update it to reflect new milestones and insights. A dynamic story shows traction and adaptability, something that particularly resonates with investors.

10. Practice but Don’t Memorize – Storytelling improves with practice. Use any opportunity to pitch in front of audiences. Then seek feedback and refine it. But never memorize which makes you sound robotic and unnatural, which is an instant turn-off to audiences.

When sharing these tips, founders will ask us if there are templates that can help them get started. We provided some resources in our post about crafting pitch decks. Be warned however, these templates are heavy on telling facts and stifle your opportunity to show your uniqueness!

Templates help VC’s filter through hundreds of pitches. The result is that your story never stands out. Ignore their structure! We recommend founders create their story and then weave slides from these templates in a way that tells your best and most compelling unique story. For example, if your personal story is the strongest opener, tell that first. If your team is amazingly talented, start there.

So what is your unique story? We are always seeking founder stories for this newsletter and our other content channels. If you have a story that you think needs tweaking, reach out and we would be glad to give you some pointers.

Mark & Basil

Two interesting posts that we wanted to highlight this week. First, we want to congratulate the Reddit team for listing on the New York Stock Exchange on Thursday! This is a huge milestone for the 19 year old social media channel, the first to IPO since Pinterest in 2019.

In a bellwether for future tech IPO’s, the shares popped 48%, closing its first day at $50.44 for a $9.5 billion market cap. Let’s see if this gives other tech unicorns encouragement to move forward this year. If this happens, expect to see a lot of relieved VC’s that have been sitting on big paper money gains, but without any distributions to investors over the past two years.

Earlier this week, an early Notion employee brought up how they had a “no hello” rule across their company, outlined in their internal communications guidelines. They wanted to prevent employees from just saying “hi” in a Slack message without explaining more about their request.

Where are you on this “hello or no hello” debate? We believe startups should have clear and explicit guidelines on their culture, values, and work practices. This is a net positive for employees and helps everyone to work better together.

However sometimes these practices can border on petty. If someone says “hi” in a message without elaborating, you can 1) stew about it in silent fury, 2) angrily send a link to the “no hello” site, or 3) ignore it and blissfully move on with your day. We think the third approach is much healthier for everyone involved. If it’s truly important, the person will respond with more details.

Or maybe we just act like decent humans and send a “hi” back 👋😊

We wanted to give a shout out to our colleague Isaiah Steinfeld for an awesome article he published on Fast Company this month. He shares how Generative AI is revolutionizing metadata tagging for videos, automating tedious and error-prone work previously done by humans and older AI techniques.

Mark is in week one of his tour across Southeast Asia having stopped in Singapore and Bangkok. Thanks for everyone that joined the healthtech coffee chat in Singapore and kudos to the startups that pitched last night at the FACE event in Bangkok. Next week he is off to Saigon, Singapore, and Kuala Lumpur!

Last thing we wanted to share, we are now actively updating our Founders in the Cloud YouTube channel, and we now have our first ten “Founder Mistakes” videos loaded there. These are one-minute tips covering some of the most common mistakes we see startup make (and that we made ourselves 🤦️). Please do check it out, subscribe, and like!