Take Your Fundraising Pitch from Mediocre to Memorable with These Storytelling Tips

Oren Jacob grew up in a family of storytellers. His parents were teachers who were constantly hosting family, friends, colleagues, passersby from around the world — each with their own story to tell. So it’s not surprising he’s built his career around compelling narratives.

After spending 20 years at Pixar working on films that revolutionized visual media, he is now the co-founder and CEO of ToyTalk, an interactive entertainment company that enables kids to converse with and learn from animated characters. In fact, the company just released its second season of The Winston Show today.

All of this work required continuous and creative pitching. At Pixar, it was about developing movie pitches for $100 million stamps of approval. And now, at ToyTalk, Jacob has helped raise over $16 million to make their groundbreaking vision a reality.

In all of these situations, storytelling has been a crucial part of making pitches memorable and resonant. Whether you’re talking about your product or your company, Jacob recommends several specific storytelling tactics to both appeal to your audience for the first time, and to forge successful long-term relationships.


Great Stories Are Practiced

The first thing to know is that no pitch is static. It evolves based on who you’re talking to, where you are, what you need to get across.

“You have your one-minute version, your 10-minute version, your hour-long version,” says Jacob. “Some people think this means having the same story edited to different lengths, but you can’t do that. It’s impossible. There’s no way to compress an hour of material into a minute and still speak with the same passion. You have to have a new approach for each one of those situations.”

On top of that, your pitch has to accommodate constant learning. Every day you have new information to work with. You have a better sense of your market, new hires with new capabilities, ideas that have only just now bubbled to the surface. Your pitch has to be as dynamic as your startup itself. “Every minute of every day, it’s never the same thing.”

For all these reasons and more, the number one most important thing you can do is practice — constantly, continuously, adaptively. This might sound like common sense, but a lot more is involved than most people think. Before he started ToyTalk, Jacob was an EIR at August Capital, where he saw countless startup pitches. “The ones that stood out were the ones that felt natural because the person knew the material so well.”

A pitch is a live performance. You have to know it so well that it seems spontaneous.

You can’t just practice your one-minute, or ten-minute or hour-long pitch over and over and over again. You have to consider what it will be like to read a room, to read investors’ body language, absorb the truth of the moment and adjust accordingly, Jacob says.

“Your pitch has to be infused with humanity,” he says. “The best stand-up comedians practice their routine for a year, so many times that they can work a crowd back and forth, move the routine wherever they need to. If someone yells out something random, they handle it and move on. You’re at your most human when you can respond well off the cuff.”

At Pixar, this meant working on a script for so long that the animated characters actually appeared to be improvising — a concept ToyTalk is taking even further. In a fundraising setting, Jacob has focused his efforts on being simultaneously so rehearsed and so comfortable that he could field any question with ease. And if he didn’t know the answer immediately, he could simply say he’d follow up without forcing an answer or getting flustered.

To get to this level, Jacob has several recommendations:

“Practice in front of someone who gets your enthusiasm but knows only a little about the actual technical, financial or business details of your company,” he says. “This could be your husband, wife or a close friend who’s not involved. Start your pitch and tell them that, by slide 2, they have to interrupt and ask a question that pertains to slide 12. Have them continue to pepper you with questions out of order so you can practice moving the conversation in and out of the various points that you want and need to make. It’s only by working the transitions in and out of your key points that you’ll actually get a real handle on the various bridges you can use to get to where you need to be in the conversation.”

One of the trickiest things an entrepreneur can face in a fundraising meeting is getting stuck midway through a conversation. One of the investors in the room asks a question, and you find yourself down a rabbit hole without a clear route back to your narrative.

“In this situation, you really have to very firmly say, ‘Hey, I have two more minutes to spend talking about this, but I can get back to you tomorrow with more information,’” Jacob says. “You have to be outside your head enough to recognize that the conversation is getting away from you and know where you need to be. Do a momentary internal audit to think, okay we’re on slide five and I have 10 minutes left. If you’ve practiced enough, you should be able to check-in with yourself and make live edits. Don’t just cram everything in. You might say to yourself , ‘Okay great they are talking about market size which connects very naturally to engagement.’”

Great Stories Have Structure

A pitch meeting should have a natural cadence, like a screenplay.

“You need to take the whole room on a journey together,” says Jacob. “This means there has to be a narrative arc with a beginning, middle and end. When you’re in command of your material, creating this structure is in your control.”

The best meetings are the ones where the VCs in the room want to take this journey with you — and to ensure this, you have to hit all the stops they’re anticipating. “Lay out the map for them at the beginning: ‘I am going to talk about engagement; I am going to talk about monetization; I am going to talk about our team and features and potential competitors,’” Jacob says.

You may walk into a meeting with 12 slides — he recommends 12 — with the plan to touch on each of them sequentially. But more often than not, an investor will ask to skip slide two or jump ahead to slide eight.

“You might be in control of how to tell your story, but you also need to read the room. If they are trying to pull you toward one topic, listen to them and adjust accordingly but keep the story’s structure intact. You have designed the story to build toward the conclusion that they have to invest in you. You have to build that case no matter what.”

Jacob readily admits that he usually starts off with 60 to 70 slides, and very painfully and thoughtfully molds his presentation to fit 12. All of his pitches have had to endure many rewrites before his team felt that they captured the spirit and intentions of the company.

If you’re having trouble cutting your presentation down, go home and deliver it to the mirror, he says. “If you’re really honest with yourself, you’ll hit that slide that doesn’t really work. You’ll see better how you can set up your conclusion without including a slide or a section.”

This is how ToyTalk storyboards its work. Mapping out your narrative visually like this can dramatically improve the flow of your fundraising pitch.

When you design your presentation, you want to make sure to emphasize the points that will drive people to the conviction that they should back your idea. If you believe the market opportunity is the most compelling thing you have to share, spend more time on it. If you believe the strength of your team is unmatched, take the time to dive into their bios and experience. You want to build your presentation and slides so that your argument only gets stronger and gains momentum as you go along.

“You might have 10 slides of nerdy graphs in the appendix that you can use to answer questions, but your story should be condensed to the point that you’re never even reading your slides.”

Never read your slides. If you find yourself doing that, you've already lost.

Tactically, Jacob says it’s also critical to not plan a full hour of material. You should be able to tell your whole story, in a compelling and detailed fashion, in just 20 minutes. “This will almost always expand to fill the hour. You’ll be interrupted. You’ll answer questions. You’ll decide in that moment to flesh something out a bit more or add more detail to something. You’ll get the sense that someone in the room wants to dwell more on product construction or this stat or that stat. You don’t want to end up running out of time

At the same time, you want to have hours and hours of nerdy details squirreled away in your head, Jacob says. “Through practicing you can feel better and better about leaving those details out, but should the conversation go that way, you can bring them to the forefront if necessary. Have some well-known short stories as examples — a user who loves what you’re doing, for example. Those can be useful answers to general questions. When you tell stories like that you can find ways to move the conversation to other points you want to hit.”

The important thing is to make the words your own. “You should be able to give your pitch with no slides. Cold,” says Jacob. “Hit every key point you want, unrushed in 20 minutes. Practice as if the projector bulb blew out several times and make sure you can still do it then — and don’t wait until the night before. Be able to recreate any idea you have on a white board in less than one minute. Label the axes and call out the three to four critical points on the graph that characterize the point you are trying to make.”

Great Stories Have Context

A big part of ToyTalk’s narrative arc was why it was special to launch in 2011. This required Jacob to vividly set the scene. With different technology spaces becoming more and more crowded with competitors, making this a bigger part of your pitch — with sharp, current intel — is highly advisable.

Why are you relevant? Why this year? Why this decade? Those are two very different questions. Answer both to give different scales of context.

When Jacob went out to field ToyTalk’s seed round in 2011, he secured financing from Greylock Partners, True Ventures, and First Round. He started with his small but very impressive team, then zoomed out to talk about trends in entertainment, why the company was relevant, and why the timing was right.

“We talked about the family market in entertainment and where storytelling was going,” he says. “We talked about what technology had made available at that point that hadn’t been possible in years before. We talked about how we’re a family entertainment company first and foremost, versus a technology company. We wanted to tell the story about building a product so in-sync with families’ needs and behaviors that the technology would fade into the background.”

ToyTalk's hypothesis was that technology would become a lot more human-centric, and that people would be looking for that feeling of naturalism and ease.

“We were able to place ToyTalk at the intersection of several trends — the idea of finding new ways to create characters and tell stories; the idea that content is showing up in so many new forms, especially in forms that we can interact with. In fact, right after we told this story in several meetings, we got lucky and Apple launched Siri. So we wanted to place ToyTalk in the context of this larger, global story.”

When the company raised more funding a year ago, bringing Charles River Ventures into the fold, a lot of these predictions had come true. There were proof points that Jacob and his team were headed in the right direction. Speech recognition was just becoming a serious focus, and more companies were expanding into a category that could be roughly labeled as “family technology” — friendly to kids, and comforting for parents.

“Opportunities come from things like that opening up,” Jacob says. “When you take those ingredients and turn them into something new, that’s an interesting potential investment. People haven’t tried it before, but could it grow? Could it be a big market? Suddenly those questions make sense against the backdrop of what’s going on in the rest of the market.”

Great Stories Have Inspiring Protagonists

Oren Jacob at ToyTalk HQ in San Francisco.

When asked, Oren Jacob will be the first to tell you that he would be happy running ToyTalk for the next 20 years. He’s that confident in the space and his company — and that made his conversations with investors all the easier.

“When they asked me if I could see spending my life making this product, my answer was ‘hell yeah!’” he says. “It’s not just a business opportunity for me. I spent 20 years at my last job, so I’m not coming in here with the intention to fly in and out in a couple years. When I say that, I’m not overselling myself, because it’s true.”

For Jacob and ToyTalk, the people involved have been a vital part of their value.

Humans have an innate desire for relationships they can trust.

“They grow and evolve over time, but that’s what you want with an investor. You’re marrying them. You can’t divorce them. It’s a serious commitment,” Jacob says. And when you’re forging a bond like that, you want investors to know they are placing bets on talented, competent, compelling protagonists in a story where everyone is rooting for them to win.

That’s why crafting an intriguing and confidence-inspiring team story is so important, Jacob says. “By far, the most important slide for us was slide 3 in our pitch. That was the one that said ‘Hi, we’re ToyTalk, this is our first round, and this is what we’re doing.'"

At the time, the team was comprised of Jacob himself, Martin Reddy, Renee Adams, Brian Langner, Michael Chann and a few others — most of whom had spent significant time at Pixar and other influential software companies that only hired the very best.

In some meetings, this infamous slide No. 3 was so convincing that investors told Jacob to close his laptop at that point — they were in. Don’t underestimate the power of the characters in your story.

“The team was a direct match to the challenge at hand,” he says. “There was a resonance there. There was an obvious passion that we all shared.”

Great Stories Are Unexpected

The best stories take a bunch of familiar puzzle pieces and combine them into something new and valuable, Jacob says.

“You can find creative people. You can find experts in speech recognition and talented mobile developers. Each one of these elements is a solid investment that has worked in other ways before."

When you shuffle them in different ways, you can end up with something very unique.

"People might have those elements, but they don’t have the kind of writing we do — so that separates us from the pack. Our background from Pixar suggested we could do that very well and we could recruit for that going forward. I could defend each of our puzzle pieces, and I could defend deploying them in ways that investors had never seen before.”

There's one other element that a lot of investors rarely expect to see these days:

“You have to make them believe how much you believe in it, and how much you want to go on that journey with them — even if neither of you knows how big it can get," Jacob says. "When you’re in pitches you should make your case not to raise money but because you’re so excited about what you could possibly accomplish.”

Photography by Michael George.