Sell With Story: The Storytelling Systems Great Sellers Use
“Three years ago, my cat died, and I was devastated. He was a one-and-a-half-year-old cat, seemingly perfectly healthy. One day he was there, and the next day, he was gone.”
That’s how Daniel Rotman, founder of PrettyLitter, opened his pitch to venture investors.
A story.
Within minutes, the investors were fully locked in. Why? Because stories do something facts alone can’t.
They make people care. Attention rises, skepticism softens, and the audience becomes more open to receiving the underlying message.
PrettyLitter was later acquired by Mars, Inc. in 2021 for a reported sum of $1 billion, with Martha Stewart becoming the brand’s spokesperson – proof that the right story doesn’t just capture attention; it can shape real business outcomes.
In Episode 08 of Sales Reframed, host Eric Janssen breaks down the storytelling systems great sellers use to earn attention, cut through skepticism, and make their message land.
You’ll hear from Kellogg Sales Institute Executive Director Craig Wortmann, who built the “Story Matrix” framework that helps individuals organize and draw from stories on demand…
from Eric Silverberg and Eli Gladstone, Co-Founders of Speaker Labs, where they teach professionals how to wrap ideas in a story to cut through skepticism and make messages stick…
and from Miri Rodriguez, Microsoft alumna, CEO of Empressa.ai, and author of Brand Storytelling, who explains why your origin story may be your most powerful differentiator.
The takeaway is simple: great storytelling is always a great strategy for sales.
Reframe Takeaway
After listening, you’ll understand that storytelling isn’t a gift reserved for a few naturally charismatic people – it’s a discipline anyone can learn. When you stop treating story as something spontaneous and start building systems to collect, shape, and deliver stories intentionally, your ideas become clearer, more memorable, and more persuasive. The best sellers don’t rely on facts alone; they wrap their insights in narratives that help people see, feel, and understand why something matters — and feel empowered to act.
Episode Guests
Craig Wortmann: Executive Director of the Kellogg Sales Institute at Northwestern University; Founder of Sales Engine Inc.
Eric Silverberg: Co-Founder of Speakerlabs.
Eli Gladstone: Co-Founder of Speakerlabs.
Miri Rodriguez: Co-Founder & CEO of Empressa.ai; Microsoft alumna.
Top Episode Learnings
Storytelling Is a Skill You Can Learn
Great storytellers aren’t improvising every time they speak. They actively collect experiences, lessons, and examples they can draw on when the moment calls for it. Building a “story library” — much like Craig Wortmann’s Story Matrix — ensures you always have a meaningful story to clarify an idea or reinforce a point when it matters most.Start With the Point, Then Build the Story:
Many people tell stories and hope a lesson emerges. Effective communicators do the opposite. They decide what they want the audience to remember, then choose an experience that proves it. When the story's destination is clear from the start, the story becomes sharper and far more impactful.Authentic Stories Create Trust and Memorability:
People can sense when a story feels performative. When storytellers share real experiences, let the audience into what they felt, and bring it home with a clear takeaway, their message becomes easier to trust, easier to recall, and far more likely to influence decisions. Authenticity isn’t a style to copy — it’s doing it in your own way. And that’s what gives a story lasting impact.
Resources Mentioned in This Episode
Nazaré, Portugal (“Mount Everest of surfing”), world-record waves.
Since 2009, billions of dollars have been pledged through Kickstarter, but historically > 40% of campaigns have successfully met funding targets
Research: “Redefining success in innovative crowdfunding projects: Empirical evidence of effective mindful consumption promotion in Kickstarter”, article in the Journal of Innovation & Knowledge by Ana M. Gómez-Olmedo, María Eizaguirre Diéguez, and Jose Antonio Vicente Pascual
Research: “Persuasion in crowdfunding: An elaboration likelihood model of crowdfunding performance” article in Journal of Business Venturing by Thomas H Allison, Blakley C. Davis, Justin W. Webb and Jeremy C. Short
Research: “The Use of Narrative in Science and Health Communication: A Scoping Review” article in the Patient Education and Counseling by Matthew Z. Dudley, Gordon K. Squires, Tracy M. Petroske, Sandra Dawson, and Janesse Brewer.
Research: “Storytelling as a research tool and intervention around public health perceptions and behaviour: A protocol for a systematic narrative review” published in the BMJ Open by Becky McCall, Laura J Shallcross, Michael Wilson and Christoper Fuller
Book: What’s Your Story? by Craig Wortmann (2006)
Framework: Story Matrix created by Craig Wortmann
Case Example: “The pill in peanut butter” taught by SpeakerLabs
Research: “Telling an authentic story by aligning with your product type and price” article in the Journal of Business Research by Chin-Ching Yin, Yun-Chia Tang, Hung-Chang Chiu, Yi-Ching Hsieh, and Yi-Ting Lai.
Book: Brand Storytelling: Put Customers at the Heart of Your Brand Story by Miri Rodriguez (2020)
Framework: Superpowers and Superpassions (Talent Stack Exercise) – Episode 02 of Sales Reframed, “Unlock Your Hidden Value with Superpowers and Superpassions”
Case Example: Daniel Rotman, founder VC pitch story for PrettyLitter + Mars Inc. acquisition and Martha Stewart partnership.
Transcript
ERIC JANSSEN: In 2022, my wife and I did something that most people would consider, well, a little crazy. We sold our house, sold our cars, pulled our four kids out of school, and spent a year traveling around the world. We'd always dreamed of doing a trip like this, showing our kids that the world was much bigger than what they'd see in a classroom. And one of the places that we stopped was Nazaré, Portugal.
Nazaré is known as the Mount Everest of surfing. It's in the Guinness Book of World Records for the biggest waves ever surfed. We're talking waves as tall as an eight storey building, like 100 feet tall. When you see footage of someone dropping down the face of one of those waves, it looks like madness or magic. Like you'd have to be born with something the rest of us just don't have.
But when we visited the beach and talked to some of the surfers, we learned something that reframed how we saw them. They're not just hurling themselves at these waves and hoping for the best. They work with coaches. They study the mechanics of how the swells form. They practice for years on smaller waves before they ever attempt a monster like these ones. It wasn't magic. It was a discipline. And that's exactly how I want you to think about storytelling.
For a lot of people, crafting a killer narrative feels as impossible as surfing a 100 foot wave. But just like those surfers at Nazaré, the best storytellers aren't born. They're made. They study the craft, they practice, they build up to it. And that's what this episode is all about. We're going to break down storytelling, what it is, why it matters, and how you can get better at it.
To help us do that, we've got some incredible guests. Kellogg's award winning sales Professor Craig Wortmann, speaker labs Eric Silverberg and Eli Gladstone and Miri Rodriguez from Empresas.AI. Let's get into it. I'm Eric Janssen, an entrepreneur turned sales professor. And I have a simple mission to change the way people think about sales, because sales is a life skill. And this is Sales Reframed, a podcast brought to you in partnership with Ivey Executive Education.
Between 2009 and 2021, over $4 billion were pledged on the world's most popular crowdfunding site, Kickstarter, but less than 40% of campaigns actually hit their fundraising goal. So what is it that separates the winners from the rest? Researchers studied over 80,000 campaigns and found that the biggest predictor of success wasn't the product or the funding goal, it was the narrative.
In sales, we often get caught up making an argument for the thing we're selling. Facts and figures and features and benefits. But the best pitches wrap the facts inside a narrative that makes people care enough to listen. And this isn't just limited to crowdfunding campaigns. The same holds true for almost every kind of sale, fundraising for political campaigns, soliciting charitable donations, pitching your startup, you name it.
In fact, a number of public health studies have found that stories are much more effective than data when it comes to patients retaining information, and greatly reduce a patient's tendency to counter argue against a treatment option. Stories aren't just decoration, they're the delivery mechanism for persuasion.
Craig Wortmann has spent his entire career studying exactly this. He's a clinical professor of marketing and the executive director of the Kellogg Sales Institute at Northwestern University. Craig is also an entrepreneur, a CEO, and an author. He's the founder of Sales Engine, a professional development and consulting firm. And his 2006 book, What's Your Story? Is a must read for every aspiring storyteller. Craig's also a phenomenal guy, a great friend, and a mentor of mine. When it comes to his classes at Northwestern. Storytelling is a foundational part of his approach. But to hear Craig tell it, sales didn't come naturally to him.
CRAIG WORTMANN: When I was 17 years old, I walked up to the prettiest girl in my high school and I asked her out on a date and she said, yes. And we're still together. I was 17, she was 16 years old. And I'm not a born salesperson. I have always felt that I've got to put myself out there and take some risks. But I'm really clear with people. I'm not a born salesperson. I had to learn it and IBM taught it to me, and it took me a couple of years to really understand it. I kind of sucked in my first couple of years at IBM, and it took me a while to understand it.
So I'm not a born salesperson at all. It's an acquired set of skills and disciplines, but man, it has affected every part of my life. I'm a really good networker, because I just love people and I love talking to people, and that's a sales skill, right? And a discipline, that's changed my life. My networks changed my life multiple times. It got me here, you know, it got me teaching. It's built my business. It's been a blast.
I was running my first tragic company. My little disaster of my own making. And we were in the story business. So we were mixing up stories and creating stories that we tried to make really sticky for corporations that had dispersed audiences all over the world. And so we'd tell a story to try to illustrate something. They were trying to teach those people product development or negotiations or whatever it might be. And so we would create stories around them.
And I just got really interested in why these things are so powerful, why these things called stories are so powerful. And so I sat down and started a learning journey that continues to this day, I wrote a book about it. And I just-- I ever since, I just can't-- I see them everywhere. It's like the matrix, right? I see them, I see stories everywhere, and I try to do a good job collecting them. So I'm actually a collector, some people collect wine or whatever, matchbooks I collect stories, I literally collect stories.
ERIC JANSSEN: Do you have a story journal or a file? Where do you log these?
CRAIG WORTMANN: I do so-- I so I was trying to get better at this. So they always say writing a book is the beginning of your learning journey, not the end. And that is so true. And I wrote a chapter in my book called the story matrix. And the story matrix is a tool that I created. It's a spreadsheet. It's no more complex than that, but it's got rows and columns, and the columns are the types of stories that we as leaders, salespeople, whatever, must tell success, failure, fun, and legends.
And the rows are the situations where you need stories. Because I was trying to get better at this, so I was like, well, if I'm in negotiations, I need a success story, a failure story. If I'm teaching storytelling, I need success stories of stories, failure stories, fun stories. So I just created this matrix and I have thousands of stories. I mean, it's been 25 years I've been after this.
ERIC JANSSEN: Just keeps growing and growing and growing.
CRAIG WORTMANN: Yeah, and it's just super fun. It's a spreadsheet, so you just click on it, you click on the name, you know, jar of mayonnaise, you click on jar of mayonnaise. And there's the story. So I'm literally a collector.
ERIC JANSSEN: I love this idea of collecting a story matrix and having a systematized library of stories that you can pull from for any occasion. This really reinforces how becoming a great storyteller is a discipline. Anyone can collect these kinds of stories on organize them like this. It's not something that's unique to Craig or anybody else. You just have to put in the work and keep adding stories to the database. And a few years later, you're close to having a story for every possible audience and every possible setting. And there's a great reason why this is so important.
When I talk about sales, people come in thinking they're going to talk. Let's get into cold calling, let's get into pitching, let's get in-- and no doubt we cover all that. I have a hard time getting there without talking about value proposition. What is it actually that you're selling and customer selection? Who are we trying to talk to? Who are we selling it to? And so you have a quote that I thought was really good. "People will not work to understand your message. You need to work to be understood."
CRAIG WORTMANN: That is another mentor of mine. This is a woman named Professor Dr. Waverly Deutsch. Waverly is a buddy. Wave took me under her wing at booth. She's an incredible booth professor taught entrepreneurship. She is brilliant, hilarious. She's all the things. And for some reason, she took a liking to me and took me under her wing and taught me how to teach. And she would scream that from the rooftops. And I stole that straight from her. That's absolutely right. People will not work to understand. You have to work to be understood. Such a great reframe. Gah! Brilliant.
One of the most interesting activities I ever took part in with one of my businesses. We were in an incubator and accelerator for all these top Canadian tech companies. So we came together and got these amazing mentors and had these awesome workshops. Bill Reichert, who was guy Kawasaki's business partner at garage technology ventures, ran this value proposition workshop for us, and he made us stand up. We didn't know what was coming, but he'd say, all right, Craig, stand up. What do you do? What's your business?
And you'd get up and talk about it. And we're all kind of nodding our head, kind of getting parts of it, but honestly not getting all of it. And then Bill would cold call and say, Eric, in your words, what is Craig's business do? Something about story. And there's some sales involved. And like he literally said it ten seconds ago Eric, and I saw you listening. Or at least pretending like you were listening, and you can't articulate it back to him. These are entrepreneurs that are doing. You had to beat 10, 20 million revenue to even be there, and they can't stand in front of a room and say it clearly enough that someone can just actually articulate back to them what they do.
We have a tool, Eric, in the entrepreneurial selling course called the sales trailer. It uses a movie trailer metaphor, and I literally do the same thing. I say, what do you do? The students will say, well, I have a piece of tech for the guitar business. You know, something like that. And I say, great, what do you do? I'm a consultant. What do you do? I'm in banking. And I say these are all authentically true answers. Then I'll get the student that says, you know, three paragraphs of stuff and nobody understands what he or she is saying. And we have the same discussion.
And I say, I want you to say it. You know your assignment tonight is to go home and answer the second most common question you get asked in your entire life behind, how are you? What do you do? That's the second most common question you get asked in your entire life. You better have an answer for me, because consultant is not an answer. It's a super boring answer. You're missing an opportunity to be interesting and tight. Be both. And they come back like that was remarkably hard to do. What was it? Dickens, who said, you know, I didn't have time to write one letter, so I wrote you two. It's hard.
ERIC JANSSEN: What strikes me about Craig's approach is that people won't work to understand your message. You need to work to be understood. That's a reframe. Most of us assume if we just explain our idea clearly, enough people are going to get it. But clarity doesn't happen by accident. Craig's been refining his own pitch for years. He practices it, he tests it in real conversations, and he makes it tighter.
The same is true for storytelling. A great story doesn't just happen. It's built. It's tested. It's refined. So how do you actually construct one? For that, let's turn to Speaker labs. The founders at Speaker labs are dedicated to demystifying how killer narratives are crafted, and it all starts with the belief that anyone can be a great storyteller.
ERIC SILVERBERG: People think that there are some that are great storytellers and they've got this superpower that I don't. And then there's me. And I could never be a good storyteller. And that is just that, a limiting belief. Anyone can be a good storyteller.
ERIC JANSSEN: Eric Silverberg and Eli Gladstone used to teach with me at Ivey, but they left to chase the startup dream. They realized while they were working in tech that communication was a huge stumbling block for a lot of people. They were entrepreneurs with great ideas who just couldn't get people to connect with those ideas emotionally. So they started Speaker labs to help teach people that storytelling is a skill, something you can work at, develop, and master.
ERIC SILVERBERG: We think in story you recall things all the time with a sequence of events, and that's really what a story is It's a sequence of events, an experience that happened to you. We think in story, the only difference between storytellers and everyone else is they actually then go and say those things, but it's going on in all of our brains no matter what we do.
So maybe it just comes down to the confidence and the belief in yourself or the willingness to try and fail that separates the best storytellers from the rest. Everyone thinks in story, but only some people tell them. There's no good reason for that. Everyone should tell them they work.
ELI GLADSTONE: I think it's also a path of least resistance. So people form ways of communicating, and often partly because of society, partly because of disposition. People have been trained to focus on concision and get to the point. Get to the point. And when that's habituated into someone, they fall back on that as the mode to communicate. And even though they know story's awesome, they encounter this resistance to change, the discomfort of trying new things and putting it into practice and seeing how it goes and refining and tinkering from there. It's just the default mode.
ERIC SILVERBERG: There's one more thing that I wanted to say about why storytelling works, and we actually don't talk about this that much in our programs, but maybe we should, which is I think most people are skeptics in general. You hear something, especially in business. And you're like, well, Where'd you get that? Prove it. Where's the data? But when you tell a story, what you do is you cut through skepticism.
So if I were to tell you something like public speaking is the easiest skill to master in the world, what most people would be looking for is prove it, punk. But if I were to tell you six years ago, I was sitting in my office, do you notice how you just drop skepticism and you're just following along? So if you can wrap your ideas in story, what also happens is another byproduct. And I can't reference any science here, but I just know it to be true. Through anecdotal observation, we just listen to stories without skepticism. But when you hear someone tell you an opinion or a fact, what you want is proof and story cuts through that.
ERIC JANSSEN: But story doesn't replace substance. It delivers it. The best pitches don't choose between emotion and evidence. They wrap the facts inside a narrative that makes people care enough to pay attention. Eric and Eli have the perfect metaphor to describe how stories and data can work in tandem. It's like hiding a pill in a spoonful of peanut butter.
ELI GLADSTONE: People think that an idea is a fixed, boxed, defined thing, but an idea is malleable and it can be shaped and positioned and framed in so many ways. So what I love to do is I love to think about how can I articulate the same thing differently. The number 10 5 plus 5 equals 10. So does 8 plus 2. So does 11 minus 1. So does 100 minus 90. There's so many ways to articulate 10. And ideas are the same.
And so I think what people are so afraid of when we talk about the pill and the peanut butter is the idea that everybody focuses on the pill, meaning the idea that they want to get across. But if you put a pill in peanut butter, a dog is going to consume it more predictably. Similarly to how if you put any medication inside of a juice box, a kid's going to take it. Or if you put broccoli with melted cheese, they're going to eat it more readily. They're going to be more open to it. All you're doing is taking the core thing and packaging it in different ways.
So when we talk about the pill and the peanut butter, what we're really saying is how can you articulate your idea in 1,000 different ways? It's about creativity that ultimately makes people stand out, makes people unique, allows people to share ideas that an audience may already know, but to express it in a way that an audience may not have already heard.
And so for us, we like to tell this story. That's a very common experience for any dog owner, which is I had a dog that got sick and I couldn't figure out how to take the medication, and it was frustrating until I figured out the obvious solution put the pill in peanut butter, and then she becomes a drug addict and she's totally fine. The insight being put the pill in peanut butter, put any idea in different packaging and you increase the odds that people are going to take it.
ERIC SILVERBERG: OK, we talked about why does story work? Where do we talk about where people screw it up? Because like conceptually, Yes, I get it. We should tell more stories and then they don't. But say they do. Where do people screw it up mostly?
There's a couple places where people screw it up. The one that we find to be the most common is ending their story, getting to a punchline, or a moral, or a lesson, or a realization. We find that a lot of people, they tell stories and they just don't know how to make it end. So we see people ending stories. They tell the story. This thing happened, then this thing happened, and I felt this way, and then this final thing happened.
And yeah. That's a really bad punchline. And yeah. And you wouldn't believe how many really tenured, brilliant executives do that in our programs. What you need to do is you need to plan your punchline. Ask yourself before you tell the story, why am I telling this story? What's the point I'm trying to make? What's my destination?
And then in your prep, the main thing you should be doing isn't thinking about what's the story and what happened. Likely, it's something that happened to you, and you already know that. What you need to be thinking of and what you need to be prepping, really to avoid that trap, is how are you going to bring it home.
We like to liken it to landing the plane. It's the most precarious part. It's the most dangerous part of a flight, but it's also the most important get me back on the ground. The same is true with storytelling. People tell stories and they sort of flutter and don't really get anywhere at the end. But if you can figure out in advance how am I going to land this plane, so to speak, then you're going to avoid what I think is probably the most common trap.
ERIC JANSSEN: So that's the last thing that they do in the story, but it's the first thing that you recommend they do when they're starting to think about where to weave in story?
ERIC SILVERBERG: Yeah, that's exactly right is if you want to keep your audience on the edge of their seat, which is a very useful thing to do when you're speaking to someone one on one, one to many, whatever your communication context is, if you can keep people's intrigue and interest up, that's great.
So you don't want to blow the lead and tell them where you're going in advance, but certainly you and your prep work beforehand. You need to know why you're telling this story, and then you hit them with the punchline at the end.
So their experience is different than you. That's well said. Is that your experience goes, what's my point? What story am I going to tell? Make sure I know how I'm going to come to my point. They don't hear your point till the end. So it's where you start in your prep, but it's where they end in what they hear.
Another common pitfall is people saying too much, and there's so many reasons for it. Mainly psychological. Well, I haven't made them laugh yet in telling this story, so I better say more until I get a laugh or I feel like I have left out some details. So let me circle back to that moment and trying to get it perfect, trying to fill time. But ultimately, we find that concision usually wins.
So we don't say take it to an extreme, like tell 10 second stories. Ultimately, there's no right answer for how long a story should be, but it is a common pitfall when we run exercises in our programs. And when we get people trying the storytelling tool that often people say too much, just stick to the plan, trust your gut, and less is usually more.
We don't love universal truths, so that's not always true. Some of my favorite stories are long, some are short, but it is a common pitfall that people just end up saying way too much and rambling and finding their roundabout way rather than the straight way.
ERIC JANSSEN: So we talked a little bit about how people screw it up. Some points on how to do it well. If we were to coach someone through doesn't need to be in-depth step by step, but high level. How does someone think about crafting a good story? You mentioned start with the point you want to make. Then what?
ELI GLADSTONE: People have to recognize that a story is nothing more than a simple experience a person has had in their life. So often people will push back on not being a good storyteller because they don't have interesting enough stories. I tell stories about the time I learned a different way to tie my shoe. I tell stories about a time I didn't eat chocolate covered pretzels when I liked chocolate covered pretzels.
You don't need these mind bending stories, and what people need to recognize is if it is in fact true that a story is nothing more than a lived experience and you're a human being, you got lots of experiences. Once you have the point, you need to find a story to tell. But a lot of people get blocked there because they think they need crazy stories. Just find an experience from your life, when you realize the idea that you want other people to get.
And once you have that, then it becomes a matter of how do I articulate that story in a really effective way? What most people do is they focus so much on what happened, like it was 10 years ago and it was raining, and then this happened, and then this happened, and then this happened, and then this happened. And it doesn't really make stories pop. What makes stories pop is humanity, emotion. It's what people feel when they are experiencing things.
So if I say it was 10 years ago, it was raining and I went downstairs and I felt very, very nervous. That moment right there is where the story connects. But if I say it was 10 years ago, it was dark outside. And I went downstairs and then I went into the kitchen, and then I got a cup and then I got some milk. You're just waiting to hear where it's going.
But the moment I let you in to what's going on inside me and I poured the milk into the cup, and then I felt terrified. I felt the hair on my neck stand up. Now the story is coming to life, because a human is experiencing something emotional beyond just the sequence of events.
So find the point. Think about an experience you've had in your life where you realize that point. And then tell people that experience. But make sure you let them into your humanity along the way. And the last thing, as Eric pointed out earlier, you got to land the plane. Make sure that at the end of your story, no one's left thinking, why did you tell me that at the end of your story? People should know. And that's the idea you wanted me to take from that story. You got to be explicit about it. You want it to really resonate because you could take whatever this idea is, and you could just tell it to people, or you could package it in something that makes it land.
ERIC JANSSEN: So those are the basics. But there's one more aspect of storytelling that's also really important. Authenticity. Eric and Eli explain why.
ERIC SILVERBERG: There are the five senses, but everyone really does have a sixth sense for bullshit or inauthenticity. I don't know what it is, and I don't know the science behind it, so I can't reference any studies. But I know that we all can tell when someone is not being themselves, when someone's being inauthentic, and we all don't like it.
So the role that authenticity can play in sales or in storytelling is you don't need to become something you're not in order to succeed as a storyteller or as someone in sales. We like to say, and this is a bit of an abstracted view here, but we say that we teach people how to be better public speakers, not just storytellers.
One of the thought experiments that we do, and sometimes we just provide examples for it, is there are so many amazing public speakers, to name a few. You've got Oprah Winfrey, you've got Steve Jobs, you've got Michelle Obama, you've got Jim Carrey. The list could go on forever.
But in those four people alone that I just named, you won't find too many similarities between them. But they're all amazing. And what that proves is there's no right way to public speak, and you can do it in your way. Your authenticity should shine because there's no right way. So why are you trying to be something else? And it's not just true in public speaking.
This salesperson is much different than that salesperson. And they've got the exact same close rate. There's no right way to sell either. This storyteller is just as good as that storyteller, and they do it in different ways. There's no one right way to storytell either. So I think the reason that people are inauthentic is because they fall for this trap of there's a right way, or I want to do it that way.
But what they need to hear is and it's clear, by way of example, that it would be very hard for you to prove to me that there is one right way to do any of these things. Therefore, do it in your way. And when you shed the inauthenticity, stop trying to be someone else. What you'll probably find is people start liking you even more because they've got that sixth sense that I spoke about.
There's one more thing on authenticity. I don't know who to credit it to, but there's a perspective I heard once around, we want to be more like the people we admire. So borrowing from other people in their style, in what they do, I don't think that that's inauthentic all the time. I think that ultimately, for many people, borrowing from other sources that you yourself really enjoy, that might be how you find your authenticity, not how you compromise it.
So that borrowing thing that we were talking earlier, or being something you're not, maybe it's something that you want to become. And so it might be a bit of a rocky road to get there. But if you admire something in someone else, maybe doing that exact thing is what you should try. Because if you admire them, I bet you wish you were more like them. So you'll find your authenticity along the way in trying some of the things from that person and some of the things from that person, and some things from that person, and amalgamating it into whatever combination is best for you.
ERIC JANSSEN: So that's the Speaker Labs framework. Plan your punchline. Find an experience that illustrates your point. Add emotional texture to make it pop and land the plane. And through all of it, be yourself. These guys have taken something that feels like magic and made it repeatable. Something you can practice, refine, and get better at.
And sometimes the most important story is the one we tell about ourselves. It defines who we are, how we show up, and what we have to offer. My next guest has made that kind of personal storytelling a central part of her career, both as a way to differentiate herself from others in the field. And by teaching others to share their own stories authentically.
MIRI RODRIGUEZ: There are so many stories to tell about yourself, but I will choose to start with my origin story, which is where I come from my culture, where I was born. I was born in Venezuela to missionary parents, and it was a beautiful childhood. I'm a family of five, three sisters. I'm the middle one, and we traveled the country by car and outside the country, different countries in Latin America delivering missions.
ERIC JANSSEN: That's Miri Rodriguez, she's the co-founder and CEO of Empresa AI, a company dedicated to closing the gender parity gap through the use of innovative AI tech. She's also a strategic consultant, a brand consultant, a Microsoft alumni, and an expert storyteller. Not to mention the best selling author of the award winning book Brand Storytelling. Again, through line that connects all of these incredible lines to her CV is her steadfast belief that a person's own life story is one of the most valuable tools that they have.
MIRI RODRIGUEZ: Eventually, the missions brought us to Miami. They invited us over to Miami and we started our lives here. I was 13, which is definitely not a fun age to move to another country, learn a new language and all the things, but we made it work. It was very humble means.
So starting to work at 16 to make ends meet and to get through high school and through college. We each earn scholarships, full ride scholarships because our parents couldn't afford to pay for our school. It was a great time because that also instilled in us in me hard work.
ERIC JANSSEN: Miri graduated with a degree in communications and started working in tech. She was eventually recruited by Microsoft where she spent 13 years helping to define their brand strategy through a focus on storytelling, as well as helming their global internship program. I want to talk about your role as the head of the Global internship program you've been on-- I'm going to assume the receiving end of, I can't even guess 100, thousands, Tens of thousands of applications.
MIRI RODRIGUEZ: Tens of thousands, probably.
ERIC JANSSEN: Tens of thousands of applications, hundreds or thousands of interviews, probably. This is originally how we connected because I'm like, you must be a magnet for all of these, the good and the bad and the amazing. And the horrible, everything in between. From your perspective, then having seen tens of thousands of these applications, what is it at the top of the funnel when you're doing your first screen? What is it about the good applicants that make them stand out?
MIRI RODRIGUEZ: We look for personal story. I mean, when we've hired people and again, so many applications come in so many well qualified candidates, it really becomes not just about the academia and the background qualifications, the technical backgrounds or the hard skills. We look for soft skills and we look for the story. And we've seen, I mean, incredible stories, incredible ways that students, you know, present themselves and share that story. They get very creative.
I'll say it's not about the creativity. I mean, that's points for creativity, but beyond creativity, it is the essence of how they're putting themselves out there for something that they want. Ultimately, when we make decisions to hire someone, it is about how well they can articulate their mission aligning to our mission, their story, aligning to our story.
And it's not broad. It's not like, Oh, I love what you're doing because you're changing the world. I to go change the world to, OK, how? What have you been doing to change the world? Where have you started? It's as simple as I led a group, you know, in my high school, and I did-- I made this change or whatever, whatever that looks like. It doesn't have to be bombastic.
It doesn't have to be this crazy story. It's just the story that tells you that you've already aligned and you're already there, and you're ready to take on the next steps. And so I had to make a choice at that point. How do I want to show up for the audience that I'm targeting? And so this is where people are thinking about career, thinking about companies understand the company as an entity, understand the core values and the story of that company, because ultimately hiring managers are looking to see not at the academia level or the background.
There's 10 resumes that probably look like yours in that data point. But what they're looking for is, are you a fit culturally? Are you aligning to our mission? And so if you really stand out when you're telling your story, that does align. Example would be I get a lot of this question at Microsoft. We always ask, I actually used to lead the global intern program, and we asked every, every time we asked this question, why Microsoft at the hiring point when we're interviewing, why Microsoft?
And we get a lot of great answers, of course. But the best answers are those that people say, well, I'll give you an example. If it was me, I would answer, knowing my story, hey, you know, Microsoft was about empowerment. That's your thing. You exist to empower. And I know about empowerment because I came from the slums and I had to work my way through it. I started to work at 16. I had three jobs.
I know about self-empowerment because I've done this and this and that. I know about empowerment because when I got breast cancer, this is what I did and I advocated for myself. So I build my story based on empowerment. I lived notion of that mission that aligns to them, and immediately they're seeing themselves, Oh, she belongs in our culture. She's about empowerment. We're about empowerment. And there's the match. And so that's when you start to really delineate your big story information into clusters of stories designed to enable and inform your audience and land them in the best way depending on who your audience is, you should have a lot of different stories, all being part of your origin story.
You know, one of the things that became very important for me was a women in tech, especially early career rising professionals. And that's because when I was a rising professional in early in my career, I sought out other women, mentorships and allies, and that was hard to come by. It was a lot of limitations. There was a lot of micro and macro aggressions.
And obviously, this is not my own story. This is for a lot of women in this industry. And so I began to share some of my branding tips, my storytelling skill sets. And I delivered workshops, one on one mentorships and that, you know, became more and more and actually extended outside of Microsoft. And it's really is my personal mission to enable to empower women.
ERIC JANSSEN: That's amazing. Part of what I talk about in sales class is selling yourself. And often when my students or young people get asked in an interview, tell me about yourself. Probably should anticipate the question is coming, right? You kind of started way back at your family's origin story and talked about your mission and values. And I love how intentional you are about that.
MIRI RODRIGUEZ: Yeah, you know, it's interesting because I get the same thing a lot of people will, even when you apply for a role or you're applying for an award or whatever it is, you know, that question comes up, well, tell me about yourself. And it's very broad. And people do go through their resume thinking that it is the data set that you've created on a paper that's going to give people an idea of who you are, and it isn't. It's really your story that people want to know about.
And so I came up with this a long time ago when I became a storyteller professionally six years ago at Microsoft, and I was brought in as a storyteller. I had a marketing background, and even with that, I didn't really know how to put the story together in a really great way. You have to design it.
And so that designing of that product, the story that you deliver, you anticipate what your audience needs from you when they ask, tell me about you as a hiring manager. If it's somebody at a cafe, what are they seeking? And truly, it is always your origin story. What they're saying is, where do you come from? What are you about? The resume fills in the gaps of academia, and accolades. But truly, what they're seeking to know is, are you someone I can trust?
And we do this psychologically. Psychologically, we ask ourselves when we meet someone for the first time, really two questions. Is she someone I can trust? And if the answer is Yes, then no. The next question your brain will ask is, do I want to get to know her more? And if it's yes, then you tell me your story. And so that's where it comes from, is you want to get to know me more, and me giving you a little bit more than you will see on a LinkedIn profile.
ERIC JANSSEN: How did you do the work to pull out that those were themes or values that you thought to be important?
MIRI RODRIGUEZ: That's a very foundational question, and it's also a very important question, because when you start doing this work, two things are going to happen. One, you are forced to think about your personal mission and your core values. And those two things begin to either align or not align with companies that you want to be a part of, or companies you want to create. And so a lot of times we get jobs for the job sake just to get the job, and we don't care or we don't pay attention, and we silence our own core values and just get the job.
When you begin to work on your personal story, it really becomes about, Wow, this is who I am, this is who I want to be. This is what I'm about. Does this company align to my mission? And so now you find yourself interviewing the companies more than having them interview you, because you want to make sure when you land there that there's a synergy in that foundation of mission.
And I mentioned in my story that, you know I work at Microsoft, I love our mission to empower every person and organization on the planet to achieve more. I cannot tell you how many times I've quoted that for myself. I'm empowering myself to empower other people, and that's how impressed I was born out of this same mission, because it's people and it's hard work.
And so a lot of times we misalign we don't align, we're not intentional. And that's where you see a lot of people halfway through the career, desperate, quitting, burnt out all the things that we hate to see because you're not aligned. So it starts with the origin story. You ask how?
ERIC JANSSEN: What I love about Mira approach to storytelling is how well it balances the emotional connection that can come from a personal narrative with a really strategic sense of storytelling as a tool, something tactical, and walking through your own origin story where you come from, where you want to go, what you want to do. That's a great place to start. It might even be the first story that you enter into your own version of Craig Wortmann's story matrix. Once you have the story, the next step is to figure out how you want to use it.
MIRI RODRIGUEZ: So now you have all this information. OK what do you do with that? Who do you want to tell it and how? And what parts of that are you willing to share and why? Now I have, of course, a lot of information in my origin story, and I leverage it in different platforms in different ways when I'm speaking to people of different cultural backgrounds or immigrants. I have an immigrant story to share. When I'm speaking to people about women, about breast cancer. I have a breast cancer story to share.
We are living an entire multifaceted life, and all of these pieces of our lives come together to bring up and make up who we are. And it's really, you are in power of that story and what you want to say. So what I do next is all of that information informs your next step. Who do you want to impact with that story? And that's you choosing your audience. Everybody has an audience, so that also shapes how you're going to show up.
ERIC JANSSEN: This is great. I'm going to mix two analogies here. One analogy would be a hit singer, you know, really popular band. My daughter is into Taylor Swift, right? She's got a song that she sings and she goes from stage to stage, arena to arena singing that song. And there are people who love it. And there are people who hate it. But this is my song. Like it or not, that analogy may be not the best one to apply to a job interview, right?
It's not like I have my story and I tell the same story to 20 different audiences, like it or not. You know, this is it. Contrast that to almost like a piano chord, right? It's like I have all these notes that I can hit. All of them are true, but the chord that I play depends actually on the audience that I'm sitting across from. Is that a fair analogy?
MIRI RODRIGUEZ: It is. And I will say this because I do get asked a question. Well, isn't that an authentic. Isn't that not all of you? Are you hiding parts of yourself? And I'm asking the question back and saying, do you see all the parts of all the people that you love? Do you see all the parts of all the people that you consider heroes, or that you like the brand? No. They're showing you parts of their brands that works for them and what they choose.
And that's the intersectionality of us all, and that's what we choose. And I will also warn and say if you're trying to fit in every single staging company again, you don't have possibly don't have a mission statement that's driving you. And then you're going to find yourself lost in an industry or in a career that you possibly just got just because you started the first job. I got to go and make money.
So and there's that dichotomy, especially at the age of 20 something where you're just you're trying to make money. Sure. And I've been 25 and I was trying to make money, but eventually that mentality wears out quickly and you realize it's not just money. You need something bigger than that to be motivated and wake up every single day, whether that's your own company or working for a company, that of your dreams or both. Which is what I'm doing right now. So it is mission based every single time.
ERIC JANSSEN: We've talked in previous episodes about how the most important pitch you can make is the way you pitch yourself to employers, friends, family, even romantic partners. Having a defined sense of your own story and being able to use that story intentionally as the emotional hook that captures someone's attention and imagination is crucial, not just on a sales call, but in every part of your life.
The ability to tell a story about yourself, to articulate your superpowers and your super passions can open incredible doors. So I hope after listening to this episode, you feel better prepared to start putting in the work, collecting your own stories, and practicing how to tell them with emotion, impact, and authenticity.
[MUSIC PLAYING]
This time around, our one thing is going to be a little bit different. We've talked about how to construct a great story, how those stories can help you connect to an audience on a deep emotional level, and how a great story can be the peanut butter around a pill that makes it easier to swallow. And after all of that, I think it's fitting that we end this episode with a really, really great story.
And for that, I'm going to turn things back over to Craig Wortmann and a story he shared with me about a young entrepreneur named Daniel, who was pitching an idea to Craig and his colleague Carter Cast.
CRAIG WORTMANN: Most people when they're pitching their businesses, they rely on facts. We should do the exact opposite. Not divorced from facts, but tell stories. 4 and 1/2 years ago, we were in our Monday morning meeting at our venture capital firm. And Carter has a lot of talents, this man, one of them is e-commerce. He was the founder and CEO of walmart.com. Like, the guy is the man.
He and I were in a meeting and one of our limited partners said, just kind of offhand, hey, Carter, there's a cat litter business in California. It's an e-commerce play started by a young guy named Daniel. He's 27 years old. Can you just take a look at it and see if there there? And Carter says, sure.
The meeting goes on. Meeting ends. I run down the hall, put my hand on my buddy's shoulder. I'm like, hey, man, can I sit-in with you on that, me like, I know nothing about e-commerce. I'm a sales guy, but I'd love to just hear what you would ask a cat litter business to determine whether that's a fit for our portfolio. He's like Craig, of course, man, you could sit-in.
So 3 and 1/2 weeks go by and we're all super busy, including this young entrepreneur. And the meeting gets set up and it's 6:30 at night in Chicago. I'm at home having a glass of wine already, and Carter's driving through a rainstorm in Indiana, going to see his elderly parents.
So here's the thing. You're a 27-year-old entrepreneur. You got a 20 minute meeting with two venture capitalists. That's all you're going to get. And when I teach this to students, they say, what's your move? And they just look at me and I say, here's what this guy's move was.
Carter gets on the phone. He introduces me. He says, Craig safely at home. Daniel, I'm so sorry. You can hear I'm driving through a tremendous rainstorm, but I just want to assure you, you've got 20 minutes. You have our full attention. Tell us about your business. And there's a long pause.
And this young man says, three years ago, my cat died and I was devastated. He was a 1 and 1/2 year old cat, seemingly perfectly healthy. And one day he was there, and the next day he was gone. And I was devastated. I wandered around in a funk for a couple of weeks, and then I got angry. I had to figure out why this had happened to this cat, and I went to a bunch of veterinarians and I asked a lot of questions.
And you know what, you two, I learned a lot about cats. I learned that vets call cats stoic animals, because they wear their emotions on the inside. And I don't know if you two are even pet owners, but if you're, you know, if your dog lovers, when you get home from work and you have a dog, you know exactly what you're getting because they're the exact opposite. They wear their emotions on the outside.
But what that can mean for a cat is that your cat can have a terribly debilitating disease, and you'll never know it unless you take your cat to the vet. The vet recommended quarterly visit, which is like 280 bucks. And I didn't do that, and I regret it. So I resolved to solve this problem. So no one would go through what I went through. I invented a new cat litter. It's called Pretty Litter.
It's called Pretty Litter, because it's based on a white silica that's mined in only four places in China. I own the exclusive rights to one of those mines. The reason that's important to you, too, is white silica is four times lighter than clay, which is what every other cat litter on planet Earth is made out of. Which means I can turn this entire industry on its head by disrupting its going business model.
Subscription businesses have been tried before. They don't work because clay is too heavy. Not anymore. Furthermore, I've treated the White silica with an enzyme such that if your cat has any of seven disease states when it pees on the cat litter, the cat litter turns red. So now you know what questions do you have? That was the first three minutes of that call.
Carter cast, who one of the most accomplished people I know in the world, does not suffer fools. He had pulled off the highway in the first minute of that story. He was he was entranced, as was I, and I was writing as fast as I could because I am a story collector. And as soon as he said, three years ago, my cat died. I was to my notes, writing everything down. I called him afterwards and verified the story. I said, did you practice that story? He goes hundreds of times. Do you put those pauses in? Yep by design. Can you believe that? Now the fun part is, would you like to know if we invested?
ERIC JANSSEN: Yeah.
CRAIG WORTMANN: We did not, because no one did. Everybody wanted into this kid, including us. Everybody wanted in. And he figured out he was such a great storyteller. He didn't need money. He got customers. He got bored. He just did it. He sold Pretty Litter to Mars Corporation two years ago for $1 billion. Martha Stewart is their spokesperson. It's a thing. It's unbelievable.
When Carter and I teach and we teach together sometimes, you know, one of the things we say to students is, did that story have any facts? And there's 15 facts in that story. So I always say to students, it's not it's not a competition between facts and story. Don't spew facts at me. I'm not listening because I don't care. Tell me the goddamn story and take a risk.
Did this guy take a risk? Goddamn right he did. Starts a story with. Three years ago, my cat died. Here's my pro forma revenue curve, which is garbage. Here's my first cohort analysis and what the people are saying about it. Here's the silica, here's the enzyme, here's the science. And that's all wonderful. We have to know all that stuff. We'll figure that out in diligence. Get us interested, set the hook.
ERIC JANSSEN: Thanks again to my guest this week, Craig Wortmann, Eric Silverberg, Eli Gladstone, and Miri Rodriguez. And of course, thanks to all of you out there for listening. And remember, a great story is always a great strategy. Next time on sales reframed, it's our final episode of the first season and we're taking on a big topic the future of sales.
This podcast is brought to you in partnership with Ivey Executive education, part of the Ivey business school. Consistently ranked among the top business schools globally, Ivey Executive education delivers high impact learning experiences for organizations and leaders at all levels, from custom designed programs to coaching and open enrollment courses. Ivey works with executives and business operators around the world to drive real results.
Their mission, like ours, is to turn cutting edge research into practical insights that help people learn, grow, and succeed in a changing world. This show takes a village. I'd like to thank our executive producer, Sean Acklin Grant, and our editorial advisor, James Greenhill. Our audio engineer and producer is Carol Eugene Park, and our narrative producer is Michael Catano. Thanks also to our creative directors, Cristina Ball and Michelle Stanescu. Thanks for listening. We'll see you next time.
About Sales Reframed
Sales Reframed is a podcast that redefines sales as the ultimate life skill. Blending research, storytelling, and strategy, it explores how influence, resilience, and purpose drive success in every field.
Developed by award-winning professor and entrepreneur Eric Janssen, and in partnership with Ivey Executive Education, the show makes sales human, practical, and accessible to everyone.