The Bregman Leadership Podcast
Episode 46

Terri Sjodin



What are you doing to create opportunities for yourself? Terri Sjodin determined that if you want to accomplish your goals faster, you have to be “scrappy,” and that means bending the rules and thinking creatively. We discuss the stories of successful scrappy people in her book, Scrappy: A Little Book about Choosing to Play Big. Learn how to create “clever awakenings” that get your audience to pause and take notice, turn your irritation into something positive, and break out of normal routines to get scrappy about your success. Listen here.



Book: Scrappy: A Little Book about Choosing to Play Big
Bio: She is one of America’s most highly sought after female speakers and has trained and motivated thousands of people from all over the world. Her unique specialization is advancing the persuasive presentation skills of professionals. She is the author of the national bestselling book, Small Message, Big Impact (Penguin/Portfolio), which hit the New York Times Hardcover Advice & Misc. bestseller list, Wall Street Journal Hardcover Business bestseller list, and USA Today Money bestseller list.

She is also the author of the highly acclaimed book, Scrappy: A Little Book About Choosing to Play Big (Penguin Random House/Portfolio) which was just released in the Fall of 2016 and New Sales Speak – The 9 Biggest Sales Presentation Mistakes and How to Avoid Them (John Wiley & Sons).


Peter: Welcome to the Bregman Leadership Podcast. I’m Peter Bregman, your host, and CEO of Bregman partners. This podcast is part of my mission to help you get massive traction on the things that matter most.

With us today is Terri Sjodin. She wrote the book, most recently, Scrappy, a little book about choosing to play big. It’s a really fun book with lots of great examples of scrappiness. Terri, welcome to the Bregman Leadership Podcast.

Terri: Thank you Peter for having me. It’s a pleasure to be here.

Peter: Terri, what is scrappy?

Terri: I think of scrappy as being defined as full of fighting spirit. It’s synonymous with having moxie, being feisty, enthusiastic, gutsy, spunky. Probably one of my favorite definitions comes from the urban dictionary, which describes a scrappy person as someone who’s little, but can still really kick some ass, so I like that one too, but when you’re scrappy, you have this determination of a street fighter. You work smarter, you’re willing to work harder when you need to, and you’re willing to take some risks and to play big no matter what the obstacles are, so the word scrappy kind of embodies the mix of all of these traits plus what I call the gumption to actually take action.

Peter: You have this great quote at the beginning of the book, which is the impetus of the book, and also answers the question, in part, why this is an important book, why we need to be scrappy. You write, “We are not entitled to a person’s time and attention. More often than not, we must earn the right to be heard.”

Terri: Absolutely. I think that in today’s competitive market, and let’s be honest, it’s not going to get any better. I don’t think we can say, “Let’s all take a break until the competition isn’t as tough.” We really have to kind of gear up by just the mathematical volume of humans that exponentially is growing, and we have to consider, all right, where are we in this kind of competitive link, and then how do you set yourself apart from the masses, and I think Scrappy is about finding a clever workaround. Maybe not going through the front door, but rather really kind of using your internal analytics, and coming up with a fun way to find a workaround to make things happen for yourself in a shorter period of time.

Peter: You have a million great examples, in the book, of scrappiness. Can you share some of them? The one that’s standing out for me most is the girl scout cookies in front of the pot dispensary, but I’m sure there’s others.

Terri: Right. When we’re talking about the scrappiness, I kind of almost want to go back and create this set point before we get the the girl scout, if that’s okay with you.

Peter: Sure.

Terri: While I can’t really remember when I first heard the word scrappy, I do recall becoming aware of this notion to do something to stand out from other people, and maybe your listeners are kind of feeling the same way. I was kind of struggling at my very first sales job. I was trying to make things happen, and I kind of kept getting blocked at every turn, and I was getting frustrated, and feeling a bit hemmed in, and I thought, “How am I going to change my circumstances?”

Like I said, it was a Friday night, I’d gone to the movies with some friends, and we went and saw that classic old school film called Wall Street where Bud Fox is played by Charlie Sheen, and he’s trying to “bag an elephant,” which in this case was the character Gordon Gekko, who was a big corporate writer, and that character was played by Michael Douglas. There’s this sequence of scenes where Bud Fox basically cold calls his office 59 days in a row. He can’t get in so he kind of comes up with this clever plan to find out when Gordon Gekko’s birthday is, show up on his doorstep with a box of cigars, and then hopefully earn the right to be heard.

When I saw this sequence of events, ultimately as the story unfolds, he gets the shot, but I got the lesson. I thought to myself, “Shoot, that’s a great awakening. What am I doing? What am I doing to really create opportunities for myself so that I can then make that play.” That really was just part of my philosophy, and that started over 20 years ago, and so since then, over the years, I’ve done lots of little scrappy things to get in the door, but I’ve always been intrigued by, as you mentioned, the stories of other scrappy people who did things that I couldn’t even begin to start thinking about, but then when I hear what they did, or how they executed, I’m like, “Oh my gosh, I may not replicate that, but it sure is a great trigger to give me some ideas that might work in my situation, or my scenario, or in my environment.

Peter: Now give us the story of the pot dispensary.

Terri: Okay, so again, here’s this beautiful example of scrappiness. I was a girl scout, I’m sure you weren’t, but many of your listeners were probably girl scouts, and if you participated in the annual girl scout cookie drive, then you know even though people probably think it’s easy to sell girl scout cookies, it’s not. The goal is to sell at least 100 boxes so that you get the patches, and the treats, and the money for your troop, and all that good stuff. You’ll go door to door, and then you take all these orders, you turn the form into your troop leader, then the cookies come in, you have to sort the cookies, and then you have to deliver them, and then sometimes people don’t want the cookies. Sometimes they don’t have any money, you have to go back. Moving a hundred boxes is just not easy.

Fast forward to two years ago. I’m reading this article in the Los Angeles times about a young lady named Daniel [Lay 00:05:40], and she and her mom decided to bypass that entire process. What they did, is they actually just setup a girl scout cookie stand in front of a legal marijuana pot dispensary, and they moved 117 boxes in two hours. I thought to myself, “Now that was scrappy.” Right? She saved herself a ton of time, a ton of anxiety, she didn’t have to deal with the same old rigmarole, and that is just a beautiful illustration of just a clever workaround to help you get somewhere faster. While I’m sympathetic, and I understand that’s probably not the girl scout’s position that they want young ladies standing in front of pot shops, I think you get the idea here of what we’re trying to accomplish with the scrappy workaround.
Peter: What I like about this story also is on the one hand, it’s brilliant, and on the other hand – we’re going to have several hands here – On the other hand, it works. Right? They moved over a hundred boxes of cookies, and on the third hand, if you’re going to take the risk of being scrappy, you’re also going to take the risk of offending people to some degree. By definition you’re doing something that’s different than everybody else is doing, you’re breaking rules.

You quote the former director of Google Ideas, who says, “Scrappy means not playing by rules, and that means that not everybody’s going to like you, and it also means you’re probably going to go too far at times, and you are going to anger people.”

How do you manage – and I think there’s two elements to manage here – one is yourself, your own courage in the face of going a route that’s very different than other people go, and maybe being misunderstood, which is very hard for us often, and then the second is how do you manage other people’s responses, which we can’t control, but actually may be very negative and may backfire.

Terri: The way that I would approach that question is really starting at a 20,000 foot view. I think on some level, people understand that this kind of notion of having a fighting spirit speaks to persistence, and so there’s a part of us that goes, “Well yeah, of course I want to, I’m persistent, I try hard, I try to come up with clever ideas,” and what I would say to someone is, “Yes, scrappiness lives on the persistence spectrum, but nothing irritates a persistent person more than the scrappy person who comes up with the clever idea and flies right by them.”

Peter: Let me interrupt you because I just want to make this distinction between scrappy and persistence as I see it, which is that there’s the clever idea, which has to happen before the action, and then there’s the persistence, which happens during and after the action, and they’re two mutually exclusive elements to being effective. Am I thinking about this correctly?

Terri: I don’t know if they’re exclusive. I think they’re partners. I think they just have different jobs on the continuum, if that makes sense. For example, you might start out initially with a small play that just gets you in the door, but then once you’re in the door, you might have to come up with a medium play that takes it a little bit further, and then, of course throughout the book we find that there are people that after a small play, a medium play, things were moving forward, but they still hadn’t completed their goal. Then they might have a big play just to kind of push it over the edge. My notion of scrappiness ties in with persistence based on the principal that you don’t have to score on every play, just advance the ball. That’s kind of how it all ties together and works.

I’m not a high risk person, and we talk about this in the book. My scrappy plays tend to be a little bit more conservative, and I have a personal philosophy, which is, let’s keep it scrappy and classy. That classy momentum really serves me with my brand. There are other people who do really crazy over the top things, so I wanted to be able to share stories that show all of that range. I think a small play can have a pretty significant impact, but medium plays work, and big plays work, and it depends on your risk tolerance. Some people are willing to do some pretty risky, edgy things that quite frankly, I wouldn’t be able to do, but they did them, and they worked, so God bless them. I think that there are the Davids in the world of Goliaths that are able to take that risk and make something big happen.

That irritation piece, just to kind of go full circle, I’m sure that in any competitive environment when somebody’s a true competitor, and they are, let’s just say that they are a qualified competitor. If you come up with a scrappy idea and you beat them, of course they’re going to be irritated. They lost. Right? That’s how it works. I don’t apologize for that. I think that that’s the beauty of living in a free enterprise system. We work hard, you come up with a classy, clever idea that gets you the deal, you’re the winner, yay you.

Peter: I think that’s absolutely right, and I’m less worried about the competitors than I am about the targets. There’s this great example that you give in the story about diapers. I think it was Randy Gage.

Terri: Randy Gage, right, mm-hmm (affirmative).

Peter: Randy Gage. Why don’t you share that example? Then we can talk about it.

Terri: Yeah. I’m really glad you brought up this chapter, because we have this whole chapter that’s based on risk and reward. I call it the crash and burn chapter, because there’s a lot of things that people do in the name of trying to be clever and get in the door, and they’re just off putting, or they’re irritating, or they’re annoying, and the recipient does not like the idea. Again, that’s not scrappy, that’s not smart. We jokingly say about screepy if you do something that’s kind of creepy, off putting, or annoying, or make somebody feel like they’re being stalked, that’s not a scrappy clever plan. Now what works for one audience is going to be very different from what works for another audience, so you cannot go into this whole concept of thinking that you can use a one size fits all strategy and think it’s going to work.

For example, on a small scale, I had the opportunity to see a gal, or to see a gentleman from Mattel speak on the significance of Barbie, the evolution of Barbie, and I thought it was so cool that they came up with an entrepreneur Barbie, so I sent entrepreneur Barbies to a couple of my key contact power business women colleagues, and they loved the doll, and they thought it was amazing. I’m probably not going to send you, Peter, an entrepreneur Barbie. That’s going to be a strategy that’s not going to work for you. You’re probably not going to think that’s cool and clever. How does that tie into Randy Gage?

Randy Gage is known as a very kind of in your face, aggressive, marketing strategist, and he likes to do things that are super disruptive. I’m not, that’s not my style. I might send entrepreneur Barbie. He, as one of his marketing strategies, decided to send out a mailer that included a Depends diaper, and the premise of his marketing letter was basically, if you attended his boot camp on marketing strategies, that the ideas were going to be so big that you were basically going to kind of, quote/unquote, I’m going to say it gracefully, kind of poop your pants. People received that letter. His market thought it was hilarious. They responded to it. He sold out the conference, and kudos to him.

If I tried that same strategy with my audience base, they would be completely offended. It would be completely off putting, and it wouldn’t work. His scrappy strategy worked for his audience. It would not work for mine. That risk tolerance for him was low because he knows his base, so I think that again, you can see kind of the range. What works for you is not going to work for other people, and that’s kind of the Randy Gage story.

Peter: I think what you’re saying is you have to understand your brand, that if you understand your brand, and you understand your audience, then what you want to do is come just to the edge of what they’ve seen before. You want to go beyond what they’ve seen before, but not so far that you end up offending your audience or disrupting your brand, in a sense. In order to do that, you have to really understand who you are and who you’re speaking to.

Terri: Absolutely. Again, there’s a continuum. If you think of kind of the scrappy range as being on a pendulum. Some people are going to do things that are more kind of scrappy and cute. Some people are going to do things that are more edgy and daring. It kind of goes all over the board. I would only recommend that you kind of take the time to really think through the strategy, number one, and what’s in alignment with you and your brand, but number two, really take into consideration the wants, needs, and expectations of the recipient that you’re targeting. We talk about this a lot in the book. If you’re going to put forth the scrappy strategy, you better know who your target is.

A simple example of that is my mom and dad at Christmas. I love my parents. They have their own little habits within their relationship, and one of the cute little thing that happens is my dad always gets my mom See’s marzipan chocolates every Christmas, and she is just as excited every Christmas when she opens it as she would be as if it was a brand new surprise that she’d never received before. I, on the other hand, do not like marzipan chocolates. I think they’re gross, so if my dad gave me marzipan chocolates, I would be like, “Gross dad. I can’t believe you got me marzipan.” My mom is thrilled by it.

Again, make sure that the gift that you’re sharing is appropriate to the recipient so that they will have a lovely positive response. I call it a clever awakening. That’s really the goal of a scrappy effort, to create an awakening in the mind of a recipient, where they go, “Oh that was cool,” or That was really clever. Okay, I appreciate the fact that you’ve gone this extra step, so now I’m going to give you an opportunity to kind of share your message with me, whatever that message is.”

Some people are selling themselves to get a new account. Some people are selling themselves to get a new job opportunity. Some people are trying to sell themselves to earn a promotion at work. Sometimes it could be a scrappy effort just because you want to experiment in some totally different direction in your life, but the beauty of scrappiness is about helping you to get there just a little bit faster without having to go through the kind of day to day drudgery of trying to get through the front door, which can really be a long tedious life.

Peter: I love that phrase, “A clever awakening.” Is that what you said?

Terri: Yeah.

Peter: Yeah. I love it because it goes right to the heart of what you’re trying to do, which is that we get millions of emails every day, we get millions of people making the same kinds of requests over and over again. There’s lots of people trying to get our attention, and the goal is to pause, to get someone to pause, in relation to you, in a positive way, and to be able to stand out from the crowd of everybody else in a way that makes them say, “Not only has this person stood out, but I kind of like what they do. It was clever what they did, and that makes me want to pay a little more attention.”

Terri: Absolutely. Right? That’s why I say, “Look I don’t have a problem with what I call positive disruption.” There’s a big difference between coming up with a positive disruption that makes people go, “Wow that was really clever. That was cool,” versus doing like, “Oh my gosh. That person’s completely annoying me.” There’s a couple of really great examples at the back of the book, and they come in all different forms.

Sometimes people are at the beginning of their career. Sometimes people are in the middle of their career. Some of them are towards the end of their career. Sometimes people are working on a philanthropic effort, and they’re trying to get a donor to invest time, or money, or resources into a philanthropic project. There’s so many beautiful ways that people have executed scrappy strategies that just got them where they wanted to go faster.

I think that’s the fun part of the book is that you go, “Oh my gosh. How did they come up with that?” I don’t think it’s possible to read all these stories and not feel like, “Oh my gosh. I’m a little bit inspired.” These are really normal, everyday people who pulled off some pretty cool scrappy efforts and made things happen, so I think it’s relatable, I think it’s fun, and quite frankly, I was inspired by ever single interview that we conducted putting the book together.

Peter: Part of me feels like in this day and age, everything’s been tried, so nothing can really be a clever awakening. On the other hand, I think we’ve all gotten into such a rut that we do the normal things, we send the normal emails, we’re moving so fast, everything we do becomes more transactional than it was maybe 15 years ago. By definition, transactional will not lead to an awakening, so it requires, in the actor, in the person who’s going to try to be scrappy, in you and me, it requires that we slow down, and that we pause, and that we think for a moment, “Who am I trying to connect with? How do I connect with them in a way that gets them to stop, take a breath, and listen, and be awake, actually to what I’m trying to speak to them about?”

Are scrappy people born, or are they made? I know a lot of scrappy people, and I also know a lot of people who are not scrappy, who can’t stand to stand out from a crowd. They get embarrassed, they get even shamed by it. Can you teach someone to be scrappy, or is it something that some people are just born with?

Terri: I think teach is an interesting word. Great question. What we’ve found is that it wasn’t necessarily a personality type that executed a scrappy strategy. What usually was the through line, or the consistent thing with all of these scrappy efforts was that there was some sort of irritation, that people felt hemmed in, or they felt like they were frustrated, or annoyed, or angry, or just quite frankly, ready for some change. They were like, “I know I need to do something to create change. I just don’t know what that looks like.” They started getting frustrated enough, and I liken it to that little piece of sand in the bed of an oyster. Without that irritation, you get no pearl. There’s usually a bit of irritation that kind of elicits a scrappy desire, and a scrappy effort.

Peter: Let me ask you a question about the irritation. An irritation has a negative connotation, like I’m annoyed about something. I’m wondering if the irritation can also be positive, like I really want something, I long for something that I don’t have, and I’ve got to do something different. Do you find that that kind of positive drive is as effective, or does it really have to be a frustration?

Terri: Yes, absolutely. Again, that positive drive is really, by your kind of forecasting, I know I’m capable of having been doing something different than the situation I’m currently in, and there’s usually a gap between where you are and where you want to be. What is that motivator? Sometimes it’s positive, sometimes it’s frustration, sometimes it’s just a yearning, a goal. One of my favorite stories is personal, and I think it’s really important that we kind of reference here that it’s not always a money play.

There’s certainly lots of examples of people that did things to get a new deal, or get a new job, or do whatever, but one of my favorites is the story of Jennifer [Matthew 00:22:37] [Rieker 00:22:37]. She had a really great job. She basically worked from home. She didn’t have a ton of interaction with people. She was in her thirties and she said that she kind of felt like, these are her words, not mine, that her biological time clock was ticking, and she really wanted to get married and have kids, it was just a desire in her heart. She wasn’t the kind of girl who would hang out at bars, she wasn’t going to go on, she tried online dating, it wasn’t for her, she wasn’t going to lurk around at gyms, and she was starting to feel frustrated like, “Where am I going to meet a really great guy?” She had this visual picture in her head of the kind of guy who would wear a nice suit, and wear the kinds of clothes that would be maybe at Nordstrom.

She gets this idea, “You know what? I don’t need the job, but what if I got a job working two nights a week at Nordstrom in the men’s department store so that I could organically meet guys who are shopping?” She does it. She doesn’t need the job, but she wanted to put herself in an environment where she could organically have conversations. Sure enough, two weeks after she gets the job, she meets this guy, and he had happened to be walking through the mall. He actually wasn’t even going through that specific store, but their eyes kind of crossed. She tells the story in the book. It’s so cute. They started dating.

Fast forward 13 years later, she’s married to this gentleman, they have two beautiful kids, and I thought that was a really beautiful scrappy story. It was classy, and scrappy, and moved her intention forward, and she was just irritated enough, but with a positive intention to come up with a positive workaround, a scrappy, positive workaround to change her circumstances. That’s what I think the message is of the book.

Peter: What that story demonstrates also is the lengths to which people are willing to go. Meaning it’s a big commitment to say, “All right, I’m going to take this job I don’t need in a place that I may or may not enjoy being in, but I’m going to do it, because I’ve got a commitment and this is different than what anyone else is doing. If I join a dating website, I’m going to be with another million people,” and it’s a way of saying, “How do I step away from the race? How do I step out of the competition?” Ultimately there’s so much competition for whatever it is that we want in life that we have to think of creative ways to step outside the realm of the competition and succeed in a different way, and that’s what you’re saying I think.

Terri: Yeah. She wasn’t sitting on the couch going, “Oh I wonder what’s going to happen?” She’s like, “I’m just going to get in the game,” and she did it in a way that was going back to what we originally were talking about, in alignment with her personality and style, she wanted to be able to have organic conversations, just kind of feel that experience, and so she was able to kind of craft this scenario. I think there were no guarantees, right, nobody was going to say, “We’re your guarantee to meet someone.”

People will often give me push back. They’ll be like, “Well you could do a scrappy thing and nothing will happen,” and I will say, “Yeah, that happens, sometimes that does happen.” You execute some scrappy effort, nothing happens, but then, or people say, “I tried it and nothing happened.” Maybe it just didn’t happen right away. Maybe you got to give it a couple weeks. Maybe you got to give it a little bit of time, let it smolder. One of the things we talk about in the book is how a scrappy effort, it has to be allowed to have a little bit of room for serendipity, because you never know how the efforts that you execute may spin out opportunities that you never even knew could happen. Sometimes they happen right away, sometimes they happen a little bit later, sometimes it could be two years later, and you look back and you go, “Wow, if I hadn’t done that scrappy effort two years ago, I wouldn’t be where I am today.”

You got to leave a little room for what I say God of the universe to do their magic. We all have wishes, we all have dreams, we all have hopes for the future, but as the old African proverb suggests, you can wish, you can dream, you can hope, and you can pray, but when you pray, move your feet. I think getting scrappy is about moving your feet.

Peter: There’s a quote in your book that I really love, and I’ll end on that quote, which is Jim Carrey, “You can fail at what you don’t want, so you might as well take a chance on doing what you love.” Just going along with the crowd is not a guarantee that you’re going to succeed either, and so you might as well take some chances at what you really want and see if you can achieve it. The book is Scrappy, a little book about choosing to play big. Terri Sjodin, thank you so much for being on the Bregman Leadership Podcast.

Terri: Thank you Peter for having me. You are a joy. Loved being here. Thanks.

Peter: If you enjoyed this episode of the Bregman Leadership Podcast, please subscribe and leave a review on iTunes. For more information about the Bregman Leadership Training, as well as access to my articles, videos, and podcasts, visit Thank you to Clare Marshall for producing this episode, and to Brian Wood, who created our music. Thanks for listening, and stay tuned for the next great conversation.