Every Startup Founder’s Greatest Challenge: Perfecting the Pitch
David Riemer talks about his upcoming book Get Your Startup Story Straight
Each cohort, Berkeley SkyDeck hosts some 50–70 workshops and for the past many years, one of our top five workshops as rated by founders has been our “Product Story” workshop with David Riemer. Then about a month before Demo Day, our accelerator track startups sit down for an intense one on one working session with David and SkyDeck’s Executive Director, Caroline Winnett, to finalize their pitch and iron out the kinks so it is perfect. With his new book coming out, I decided to feature David in my latest blog post so he can share a bit more about his journey as a long time SkyDeck advisor and now the author of the brand new book, Get Your Startup Story Straight: The Definitive Storytelling Framework for Innovators and Entrepreneurs.
Sibyl: You’ve had a long history as a SkyDeck advisor. Your workshop, “Product Story Workshop” has always been an essential workshop for our founders. What was your journey to SkyDeck and how did this become the topic you are most passionate about coaching founders on?
David: I have been teaching storytelling at SkyDeck, advising teams, and coaching them on their demo day pitches for a decade; but I’ve been fascinated with stories my entire life. I was the sports editor for my local town paper in high school, wrote musicals in college, and to this day I’m involved in theater as a commercial producer and board member at the American Conservatory Theater in San Francisco. My entire professional experience, whether as an ad guy in the ’80s and ’90s, or a tech-marketing guy in the 2000’s, was all about telling the story of products and companies. In 2008, I decided to do my own thing after leaving my job as VP Marketing at Yahoo!. I started to help out entrepreneurial students and early stage founders who were desperate to figure out their story. Then I started working with SkyDeck in 2012 when it was in its infancy. At that time, I worked with a few of the founders — along with several early advisors, to advocate for a more robust program and develop a plan for a simple core curriculum. I had been teaching storytelling in various design-thinking and applied-innovation programs at Berkeley-Haas, so it was natural for me to lean into that at SkyDeck.
Sibyl: The VC and investment landscape is ever changing. How has your perspective on startup pitching and storytelling changed over the past many years?
David: My perspective hasn’t changed a whole lot over this decade. SkyDeck has changed — the companies keep getting better and better. And I have grown thanks to learning from all the wonderful teams. It’s easier now to spot the heart of a good story and pick out the Achilles heel we have to navigate. But my core philosophy hasn’t changed at all and that is simply this — you can’t build a great story, unless you HAVE a great story to tell. This means that we can’t even begin to look for ways to make a pitch compelling and memorable until we have figured out the core story in the first place. Have we picked the right first target customer to serve as the protagonist in the story? Have we understood them well enough to derive some useful insights that inform not just the storytelling, but the product itself? Have we picked exactly the right problem to solve (which becomes the conflict in the story)? Do we solve the problem better than the existing alternatives (the context for our story)? As a result, I spend most of my time on story structure in my work with SkyDeck startups so they have the tools to develop and refine their own narrative.
Sibyl: What compelled you to write the book Get Your Startup Story Straight?
David: After virtually every class or workshop I’ve ever run, a student, product person, or founder would approach me and say, I want to learn more about this skill and develop it further. Others would simply ask, “David, when are you going to write the book?” They knew that storytelling was an essential skill if they were to be successful, and they recognized they needed to do the work. I’d refer them to books about storytelling, but none of those resources were expressly written for innovators. There was a clear market need and I’ve been doing this innovation thing long enough to know that someone was going to meet it. It might as well be me. Being stuck at home for two years during a global pandemic was also a useful forcing function!
Sibyl: You’ve seen thousands of startup pitches by now, what do you find to be the toughest part for founders about nailing down their pitch?
David: There are two things. The first challenge is articulating the value proposition for their product or service. A clear and compelling value proposition is gold. It tells the audience exactly how the protagonist in your story is going to be better off if they use your solution. Most people want to list a bunch of benefits, but they have trouble boiling the notion down to something simple and single-minded. Take my book as an example. I ultimately decided to use the value proposition of the book as the title: “Get Your Startup Story Straight.” This tells a reader that if they’re struggling to figure out their innovation story, this book will help them “get it sorted” as British folks would say. It’s typically a little easier — but also important — to nail down a crisp product descriptor as well. Again, in the case of my book, it comes in the subhead, “The Definitive Storytelling Framework for Innovators and Entrepreneurs.” One of my favorite SkyDeck companies, Ava, is empowering Deaf and hard of hearing people through an app that captures group conversations in real-time and ascribes each comment to whoever is making it. Their value proposition is simple: “Captions for all.”
The second challenge is getting founders to build emotion into their story — and the biggest challenge there is to get them to understand and internalize the fact that emotion is appropriate in the first place. Emotion is linked to memory and the best way to get someone to remember your story is to weave some emotion into the narrative. Many founders start with the deep-seated belief that they’re building a business and emotion doesn’t have a place in a business setting. It was hard to even say that out loud, because it is such a nonsensical statement. Businesses build things for people. Even highly technical B2B products are bought by people and used by people. One of my favorite examples of a founding team getting this right is Databricks. The company was founded at UC Berkeley eight or nine years ago, when two Berkeley scholars, Matei Zaharia and Ali Ghodsi teamed with a professor Ion Stoica to turn their open source data analytics engine Apache Spark into a business. Working with the founders, we dug into the narrative and realized that their initial target customer — a data scientist in a rapidly growing data-driven company — was stuck between a rock and a hard place. This protagonist in their innovation story was hired to be the superhero that saved the company by mining the massive amounts of data the company was collecting to find competitive insights to smoke the competition. Expectations were huge. But the data scientists found themselves hamstrung by the inability to easily build and run programs to surface these game-changing findings. Databricks made it far easier for them to do what they were hired to do. Anyone who has ever been saddled with huge expectations without the tools to achieve them can understand how these data scientists felt. There was real emotion in a story about a highly technical product for a technical audience. Today, according to Forbes, Databricks is one of the top 10 “startups” in the world valued at $38B. The keys to Databricks success are a fantastic product, tremendous leadership, great execution, and smart decisions around the business model. But it didn’t hurt that they developed a clear and very human story at the outset that was inspiring and that anyone could understand.
Sibyl: If you could distill your top three pieces of advice to startup founders on getting their pitch right, what would you say?
David: Get my book! The three points are 1) Sweat the story structure 2) Keep digging to find the emotional hook; and 3) Never stop refining the story.
First, regarding story structure, the narrative is everything. You may think you know the story, but by exploring different markets, listening to customers, being honest about the competition, etc. etc., you’re constantly reevaluating the story. Localwise, another SkyDeck company, provides a nice example. Founders Ben Hamlin and Maya Tobias started Localwise with the notion that they were going to build a Yelp-like solution for small businesses to help them discover and vet different service providers. But once they started talking to customers, they heard the same thing over and over again. What these small business owners really needed help with was local hiring. Their default resource for hiring was Craigslist and they hated Craigslist. Ben and Maya had the right protagonist but discovered a different insight and that led to a completely different conflict in their story that they decided to solve. They did a major pivot, rebuilt their narrative and now are a successful local job marketplace operating all over the country.
When it comes to my second point, creating an emotional hook, the magic in the story is rooted in a simple, but powerful human observation. Steve Derico is the founder of SkyDeck company Dottie.ai, and he had one of those epiphanies. He’s creating a platform to make it easier for cancer patients and their caregivers to manage their care. In one of our conversations, Steve mentioned in passing that managing care for a cancer patient is like a full-time job. That bowled me over. One full time job is plenty, thank you very much. His statement really hit me. The emotional roller coaster and pain management is quite enough, but the idea that the care is also terribly time consuming was overwhelming. I suggested that Steve use the “full-time job” notion in all of his pitches. Steve told me later that this simple notion transformed the Dottie.ai story and made his presentations far more powerful.
On my third point that refining the story never ends, founders often ask me “when is the story done?” The answer: it’s never really done. You don’t know when you’re going to land on a phrase, an anecdote, an image or frankly any story element that will level-up your story. A successful women’s fashion company, Cuyana, discovered this when they stumbled on a phrase that catapulted their company. Cuyana was founded by a Berkeley-Haas MBA, Shilpa Shah and a Stanford GSB student, Karla Gallardo. They had a clear antagonist in their innovation narrative — fast fashion. Fast fashion brands like HMS marketed inexpensive clothing that lasted a short season and then it was on to the next thing. Women filled their closets with garments that didn’t last. Cuyana was an anti-fast fashion brand that featured classic, well-made accessories and clothing that lasted season after season. One day in a brainstorm session, someone said Cuyana is simply about, “Fewer, Better, Things.” This simple expression put everything they did into crystal clear focus. It clarified their story in a way that prior articulations of their narrative had not. Today, Cuyana is growing, opening retail outlets and taking on the massive fast fashion business head on.
Sibyl: David, thank you so much for all that you’ve done to help SkyDeck founders find their essence of their story and be able to share their vision in a more compelling way. How can folks find your book, Get Your Startup Story Straight?
Sibyl Chen is the Senior Director of Program at Berkeley SkyDeck, UC Berkeley’s premier tech accelerator.