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E2A 090: From Stuck to Scale: How to Turn Ideas into Breakthrough Businesses with Andrea Kates 

 March 4, 2025

By  Scott A. MacMillan

In this episode of The Entrepreneur to Author Podcast, your host Scott MacMillan is joined by Andrea Kates, author of From Stuck to Scale and former Silicon Valley Tech CEO. Andrea is passionate about ensuring great ideas don’t die on the vine. She shares her expertise in helping corporate leaders, entrepreneurs, and scale-ups harness the tools needed to successfully transform innovative ideas into scalable, breakthrough businesses.

SHOW LINKS

Book andreakates.com/category/all-products

Where are you stuck?  andreakates.com/diagnostic
About Andrea

GUEST BIO

Andrea Kates focuses on taking business from stuck to scale, by addressing critical questions: Why don’t the best ideas become the best businesses? Why do important initiatives die on the vine? She works with entrepreneurs and leaders of large organizations to break through barriers and drive growth.

Andrea is a former Silicon Valley tech CEO, MIT Entrepreneur-in-Residence, Sloan School of Management, and Senior Fellow at The Conference Board. She’s advised companies across 5 continents like Ford, Fujitsu, Intel, KK Wind, Mayo Clinic, and Tata.

Her new book, From Stuck to Scale, integrates insights from working with 13,000 teams and diagnoses exactly what it takes to help corporate teams and ecosystem leaders succeed in bringing new initiatives all the way across the finish line.

A highly sought-after speaker, Andrea has keynoted on the TED main stage, CXO Forum in Tokyo, Edison Awards, Qintess (Brazil), Dubai 2020, Connect Bogota, and RUFORUM Africa. Above all else, Andrea loves to help leaders achieve higher levels of impact.

CONNECT WITH ANDREA

Email: andrea@andreakates.com

Website: andreakates.com

LinkedIn: linkedin.com/in/andreakates

Instagram: instagram.com/andrea.kates

Vimeo: vimeo.com/user157124071


CONNECT WITH SCOTT

entrepreneurtoauthor.com
grammarfactory.com

LinkedIn (@scottmacmillan): linkedin.com/in/scottmacmillan
Instagram (@scottamacmillan) instagram.com/scottamacmillan
Medium (@scottamacmillan): scottamacmillan.medium.com


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Episode Transcript

Please note: The transcript is produced by a third-party company from an audio recording and may include transcription errors.

Scott MacMillan

You're listening to the Entrepreneur to Author podcast. 

Announcer

Welcome to the Entrepreneur to Author podcast, the podcast that brings you practical strategies for building authority and growing your business. And now, here's your host, Scott MacMillan.

Scott

Why is it that the best ideas don't become the best businesses? My guest today is Andrea Cates, author of From Stuck to Scale, and former Silicon Valley Tech CEO, who is obsessed with making sure that great ideas don't die on the vine.

Andrea is an advisor to corporate leaders, entrepreneurs, scale-ups, and global thinkers. She has worked with teams in five continents, from Ford to Fujitsu to RUFORUM Africa, to pinpoint the challenges in bringing important technologies and products across the finish line for breakthrough success. She's spoken on the main stage at TED and at the CXO Forum in Japan. Today as MIT's Entrepreneur-in-Residence at the Sloan School of Management Legatum Center and Senior Fellow with the Conference Board, Andrea has energized teams with the tools they need to figure out how important ideas can create impact with millions of people.

Andrea, welcome. Thank you so much for joining us on Entrepreneur to Author.

Andrea Kates

I am truly excited to be here.

Scott

Listen, I shared a bit about you in the intro, but let's dive in a little. Could you share a bit more detailed overview of your incredible experience, your expertise, and the work that you're doing?

Andrea

Well, Scott, you know that I love four-beat stories, so I'll give you my life of many years in four beats. I think the first beat of the story was when I was really committed to understanding business strategy. I was very lucky to experience many revolutions as I joined the field of strategy.

I started off in healthcare and then ended up in the deregulation of energy, and telecom came into it. Then, of course, from there, we went into e-commerce. The first part of my experience was the accidental tourist in a world of huge change.

That's beat one. Beat two was reflecting on that, and I thought, what have I learned from this? The first thing I learned is that conventional wisdom, what I was taught as an MBA student, was not really applying to the world I was seeing.

I saw that fewer people were doing linear strategy, and more people were doing what I called cross-industry strategy. I decided to turn that into a process that people could really follow and have an alternative to an MBA mindset and still get their businesses forward. That was my first book, Find Your Next.

The third beat of the four-beat story was when I said, okay, let me see if I can start to work differently with companies. I was really lucky to take the book and get, as you said, onto the TED main stage and all over the world and had a lot of great challenges and insights. The third beat of the story was when I said, okay, let me get back to being a practitioner and was lucky to be the CEO of a tech SaaS software company in Silicon Valley slash San Francisco, where I was able to apply what they called the lean startup method to large companies and also the system standard for commercialization for all of the government programs and university programs in the U.S. Then the final beat of the story is where I am today, which is, as you said, I'm very lucky to be working with both the conference board, which is a global group of CEOs really in practitioner mode to say, okay, how do we get our companies to grow at scale? Then the other part of it is at MIT, where I understand that life is a lot more than just Silicon Valley mindsets. There's a lot to a VC model, but the concept of growth and scale also applies very differently to growth economies.

That's why I decided to write From Stuck to Scale, because I feel like we are in urgent need, just desperate need of different mindsets, different tool sets, and different skills to get us where we need to get to, to build our companies bigger and have prosperity.

Scott

Thank you for that. That's a really good, I think, foundation that will be really helpful for our listeners that really underpins the conversation that we're going to be having. You mentioned From Stuck to Scale.

You've recently published this year's second book. Could you talk a little bit, before we dive into a little bit of the content, who did you write From Stuck to Scale for and what is your goal for your reader?

Andrea

The goal for the reader is to finally be able to feel confident that they can lead their teams forward toward growth. Now, everything we were taught assumed that we had a spreadsheet, and the spreadsheet would automatically take us to the next level. Just take what you're doing today and either innovate, do something really innovative, or incrementally grow.

People get really stuck, as you know, when they're told, okay, you have to pivot, or plan A isn't working, you need to come up with plan B, or here you are as a subject matter in something you know really, really well, and then all of a sudden it's like, the world's changed, geopolitics has changed, you're not making margins. People really don't know what to do. They get nervous.

They pray a lot that it will go away. They hope that what they've been taught, like, let me just go back to the spreadsheets and see if I can refigure this, it doesn't work. It's such a relief.

For me, the reader should feel a sense of relief, a sense of confidence, a sense of possibility, and really feel committed to leading their teams forward in a fresh way with the knowledge that they've got great tools designed exactly for that situation of changing course, pivoting. Well, how do you pivot? Now they have tools to actually get them there, and it's very much intended to be do-it-yourself.

Scott

It's such a needed skill set. I spent years in the corporate world, and you see it so often, where teams come up with fantastic ideas, but at the end of the day, for some reason, these ideas just don't go anywhere, right? Innovation's a big buzzword, and everybody wants to innovate.

Why is it that there's such a disconnect between those ideas and the commercialization of those ideas into profitable, successful businesses? You mentioned this. Why is it such an important and urgent issue to address now?

Andrea

Well, first of all, people feel a sense of complete disappointment to the point of almost depression when something they've worked on for a really long time doesn't work. To be honest, it's humiliating, it's embarrassing, it's demotivating, and people really don't like to admit that they've tried everything, and it's just not working. But for me, that's inexcusable, and it's really unacceptable.

First of all, if you put a lot of people to work doing something and it fails, you've got a lot of disgruntled people, a lot of people who are demotivated, so that has to change. But second of all, the biggest problem is that, and I remember this one day watching, I don't know, maybe it was 16 teams of four that had gone through a long process of trying to get their ideas to really work. I had actually bet on which teams were going to work.

I was 100% sure that I could place a bet on the best ideas, and it turns out that the best ideas don't become the best businesses. So people who are great at the ideas aren't necessarily good at troubleshooting as things are going wrong, making them big, and even great pilots don't necessarily become great businesses. So to me, it's really important because we have to do better.

We have to not waste all of this talent that's invested in innovation, and we have to give people a better way out. We have to give them plan B.

Scott

I want to talk a little bit about the production side of the book, how you got from your experience and your wealth of background and expertise in the innovation space, how you got from that to the book that I see behind you and that people are experiencing around the world. How did you find the process of writing from stuck to scale? And you've been through this once before, so to the extent that you can talk about whether this was different, easier, harder, similar to your first book, I'd love a little bit of that color as well.

Andrea

Well, I knew I wanted to have a completely different type of book because I always wanted a completely different type of book. People don't read books the way they used to. Maybe they read them all the way through, but mostly what I do is I like little nano-stories, like something that inspires me, and then kind of like, okay, great, that's enough now.

I've got the nano-story, I need an espresso how-to. So I basically want to go like instant reward, and then another little nibble. You kind of get another story, and it's like, oh yeah, I can really relate to that.

And then the how-to comes right after that. That's how we learn these days. We just are so distracted, and nobody's going to sit down and read a book with the pipe in a rocking chair by the fireplace.

It's not like that. Even on airplanes, I find myself so distracted. So to me, I wanted to write the kind of book that people kept wanting, and that I actually wanted.

I wanted this thing that I call a spotlight story. I've written for a Harvard Business Review, I've written for a lot of research journals, and it can be very dense. So one of my best friends says this line, which is get to the point.

So I wanted to get to the point, tell the story, bada-bing, bada-boom, and somebody goes, yeah, nailed it. Then the second part is, okay, so now I want to do that. I'm really glad that you told me that, but I need some do-it-yourself tools.

So I wanted to write a book that was going to be full of information in the format that people really needed. So first of all, people don't read books like sitting in a rocking chair with a pipe and by the fireplace just all the way through anymore. That's a fantasy.

What we really do is we want nano stories, bada-bing, bada-boom. And then it's like, whoa, nailed it, love that. Okay, how do I do that?

I love the fact that this other group did that, but I would love to be able to do this with my team. I call it like Monday morning, what are you going to do differently? So then I wanted this do-it-yourself toolkit that was easy enough for anyone to apply because we're trying to get people to do things differently.

The third was, and as you know, I've written for Harvard Business Review and a lot of research journals, so I knew that things had to be very much validated. I care a lot about the fact that these things work, not just because of my experience, and luckily I've had 13,000 plus teams of experience, but that's still not everybody's experience. So I wanted to make sure that there were instruments and assessments and diagnostics that were at the root of this so that you could take your pulse, you do triage.

Somebody comes into the emergency room and you're like, okay, I don't feel well. And it was like, great, take him to the orthopedic surgeon. It's like, actually, I have a headache.

Okay, great. So the ability for you to take your pulse at every moment, and it happens in a very constant way as you're trying to make something big, you know, great, where am I? Pulse check, pulse check, pulse check.

And then finally, the through line is something that I loved. Actually, there's a book I loved years ago called Freakonomics, and it had a story that was almost like a cliffhanger. And I have spent the last two years studying everything from the moth to all these storytelling techniques to understand how to develop a story that people want to listen to, how to tell that in a way that is a through line.

And as you know, I was very excited that a four-year project that I worked on that started out as like a disastrous situation, which I know we'll talk about later, became the through line for the book, because it was a situation where my client could not have been in a worse situation of stuck. I mean, the stuckest in the world. The industry was dead, the prospects were grim, and there was no hope.

And at the end, we ended up with 8x revenue growth and scaled and shifted. And I outlined as part of the whole book that through line so that everybody can see, oh, how did this company do it? Oh, and then what happened?

And then, and then, oh, my gosh, cliffhanger and conclusion. So that was the way I wanted to write the book. And I was so pleased, actually, to work with the grammar factory to get it to come out exactly the way readers want to use books these days.

Scott

Oh, it's amazing. It's amazing because you really are a great storyteller. And the way that that story threads throughout the entire book really is sort of the, it's what knits the entirety of the book together.

And you've got these spotlight stories. They're so inspiring. Perhaps you can give a little bit of a sampling of that story that you were talking about to whet our listeners' appetite.

I don't want to give away everything because I want people to pick up the book and experience it themselves. But could you give us a little bit of a sampling of your storytelling?

Andrea

Yeah. So first of all, you know that it took me a while to get my voice. I think a lot of people have a story inside them.

And I love to ask people, what's your story? I love to hear people's stories. And for me, it's about the data.

But it's also about those moments, the moments of emotion. So yeah, this is a true story of how, like, I didn't even know a book was coming when this happened. But I'm standing at a conference about to cross the street.

I remember it was like the day of the World Series because I was on my way, to be honest, to a sports bar to watch the World Series. And some guy stands next to me at the street corner. And as we're crossing the street says, hey, what do you think of the conference?

I said, yeah, it was pretty good. What do you think? You know, chitchat.

We're about to cross the street. It's a big street. It was in San Francisco.

And he says, so what do you do? And I said, well, I help companies get unstuck. And I said, what about you?

He said, oh, my company's like super stuck. I said, I doubt it. He said, what do you mean you doubt it?

I said, well, I've worked with like companies in really rough spots in pretty much every industry. He says, well, we are the largest CD music manufacturer in Latin America. And I said, as I put my foot like on the second curb, oh, God, you really are stuck.

I said, as a matter of fact, it might be hopeless. He said, do you think you can help me? I said, no, no, can't help you.

Sorry. So, you know, he comes in. We were sitting at the sports bar.

I'm trying to avoid him. And then by the end of that meeting, I ended up flash into my flight to Bogota, Colombia, met with his name is Nicolás Cortázar. And it was with a company called Intergráficas, which at the time was really a cool company in the music industry, losing money hand over fist.

Guess why? You know, Spotify, Apple Music, ever heard of that? Yes.

So, you know, unfortunately, it wasn't anybody's fault, but he was not just going to go, oh, well, you know, lost my VC money too bad. It was like, these are people. These are jobs.

This is employment. I can't do this. We've got to find a way out.

I said, I honestly can't help you. Like, I don't know how to do this. So I said, but I'm willing to try.

And because of his leadership and his commitment to really doing something and his patience with tools that didn't work, and, you know, I kept trying like Lean Startup and Theory of Constraints and Cash Cows and Dogs. We tried everything. And I said, I think we're going to have to invent something here.

And so that's what I did. I took the experience I had had from that 13,000 teams, you know, 70% of which failed. It wasn't my fault, but I observed that and thought, why is it people are getting stuck and how can we get them out of this?

The punchline, which is not a spoiler alert, but it is a punchline, is that we tried at first 3D printing. That seemed reasonable. You know, take what you're doing, do a little differently, different industry.

That didn't work for many reasons. We realized we had some internal struggles and we were allowed to tell this story. But, you know, people who are in the music industry are great fun, right?

Like they want, they know all the music groups like Shakira. They, you know, like they have all these cool people coming in their offices. And then you're saying, oh, you're going to be 3D printing of like dentures and they're thinking, yeah, I don't think so.

So they also weren't necessarily enthusiastic about where we ended up, which was food packaging and the story of how they got there and how this great leadership came forward and how they moved from stock to scale. I realized one day, almost like, you know, I ended up actually going to that same street and I almost had this like coup de foudre, you know, like this crazy blinding, this feeling of insight, which is, wait a minute, we're onto something. Like this could help tons of people in similar situations all over the world.

And that's what got me to start writing the book.

Scott

Amazing. And yeah, you're right. Things are moving so quickly these days.

So many trends. With generative AI, you see a lot of businesses that are going through that exact same thing. And so it's hyper important and hyper urgent.

And what I love about the book is it's very practical, yet it's also very inspiring. And I'd love if you could tell us a little bit about the publishing process because the book has tools, it has worksheets, but it also has these incredible stories and leadership spotlights. How were you able to make all of these elements work so well together?

Andrea

The greatest part of this process is that it benefited from the new way that collaboration has entered the publishing world. My first book was more traditional. It was a major publisher.

It was a very traditional book tour and selling of books and becoming a bestseller, which was fantastic. It was wonderful. And I'm not complaining at all.

But the second book was written for a different reason. And so the process for me was that I had the vision of all of the elements, but it really took the right publisher. And I will point fingers very happily at Grammar Factory because the ability for me to say to a publisher, oh, I'd like to actually think about the design of the page first.

That's not how most traditional publishing used to work. But for me, I couldn't visualize what the stories would look like and if these disjointed pieces could come together until I literally saw it as a sketch on the page. And so it was really valuable to have a dialogue and say, this is important and be heard really well.

And then to collaborate, to say, OK, if we tell the story and we give a tool, should that tool be generic or should that tool relate to one story that evolved into saying, let's do it like Freakonomics. Let's take a storyline as a through line, thread all the way through it so that everyone can see how Nicholas made his process from envision to expand, to build, to engage, to activate, to boom. You go from losing money, hand over fist, to 6 to 8x revenue growth, like boom.

Now, at the same time, these spotlight stories were important and I couldn't figure out how to put them in until I collaborated with Grammar Factory because they needed to almost be like a magazine where you have these inset stories that aren't distracting but are illuminating and that allow everyone, not everybody relates to the music industry or the food industry. So what do you do for health care? Well, we have a Mayo Clinic story.

What do you do for people in FinTech? Well, we have Rappi, which is this really cool company. We'll tell another day.

We have Copenhagen FinTech. We have to talk about ecosystems. Great.

We have a great story of AI and the Arthritis Society Canada. We have Innovation. We have Shimizu, a large company in Japan that's in construction.

We have Hilti. I mean, we have lots of, lots of examples. So there's something for everyone, but it's designed so you don't have to read it all.

Like you go, oh, spotlight story. Let me read about like, how did Mayo Clinic do something? And that's how people need tools today.

We want what we want when we want it in the form that we want it. And so the publishing process allowed me to design something that is so user-friendly that people should be able to walk away and go, hey, I've got this.

Scott

Amazing. I remember when you and I first spoke, you know, the nature of the content that you had created was such a different beast than what you see in most books that are published. And so, you know, it really did take a lot of back and forth to figure out what's the right form for this content to take so that it accomplishes what your vision as the author and really serves the reader and the goal that you had for the reader taking them on this journey.

So for us, it was really a wonderful experience working with an author like you who had such a clear vision for the outcome that you wanted for your reader and allowed us to participate in that with you. You spoke a little bit about how your objectives or what you were trying to accomplish with the your experience with your first book. Could you talk a little bit about your goals for your book, you know, from a business perspective, what were your business goals for the book?

And now that it's in the market and it's in the hands of, in your hands and in the hands of your readers, how are you using it to support the work that you do?

Andrea

This time, I wanted the book that would be on the shelf all the time, dog-eared for lots and lots of people. So I use it to teach the course. The course is actually at MIT.

I use it to teach boot camps, both in deep tech, AI technology, commercialization, as well as innovation initiatives all over the place. And it has this universal appeal because it's visually so friendly and so user-friendly. My goal was to be able to have the tools that would be proliferated everywhere.

And so it has a feeling of long shelf life. And I will never forget walking into the office of the CEO of a large insurance company that I worked with years ago when I was first, you know, thinking about From Stuck to Scale. And they had the book Business Model Generation on their shelf.

And it looked so different from like every other business book that was on their shelf. It was like book number one, book number two. And then suddenly there was this book.

It was a different shape. It had graphics, which at that time was like crazy. And I remember thinking, you know, sometimes a bold message requires a different form factor.

And I wanted to be brave enough to do that so that people could literally like pull the book out. And every time I give it to somebody, they hug it. It's a big book.

And it's a friendly book. And it has great people in it. And it's got pictures of people who are real leaders, you know, and including, you know, Bumi Akinyemegu in Africa, including Angela Rosenquist in the US.

You know, like these are people that like literally people hug the book like a teddy bear. To me, that's fantastic. Everybody should feel like, I love this book.

I just want to, you know, like have this book.

Scott

I love that visceral reaction of hugging the book. So safe to say that the reception has been positive.

Andrea

Yeah, it's great because, you know, there's different forms. I'll give you, you know, I'll give you a three beat story on this one. So scene one, I walked into a large company.

It was a great manufacturing company. Lots of challenges right now with geopolitics for manufacturing. I walked in and, you know, it was like a big kind of classroom setting with all of their global leaders.

And they had a book in front of them like every and they knew like, oh, my goodness, like, we're going to do something here. It has that feeling. As I said, there's I was just in Brazil and people were like hugging the book.

They tend to hug a lot anyway. You know, they were hugging the book and like opening the book and writing in the book. And it's got exercises so that they were, you know, they had already done their homework.

You know, they had these. So there was kind of this visceral feeling of like, like the book is like a recipe book of like your favorite recipe that you want to cook every night. And then, of course, at MIT, it has to stand right next to very solid research based books.

And so it has to within that context be news you can use, you know, insights and tools you can take to the bank because these are people trying to make growth economies grow. And it also like I love the fact that like the person who is my boss at MIT, who runs the program I work on, Dina Sharif, she's in the book and she also speaks to the book. And and we we use it as a new foundation for alternative ways to establish growth economies.

So it becomes a form factor for change and for transformation to hold up a book and say there are different ways to grow and different ways to scale. And you can have economic agency by using this book. And so there's so many ways that I feel like the book, it's almost like a friend, like it shows up different places and it and it has different conversations with people.

Scott

Excellent. And we're going to put the link to the book in the show notes so that people can can visit that link and pick up the book if they wish. But beyond that link, what's the best way for people to get in touch with you to learn more about the work that that you do and and perhaps get some help in this area?

Because it's like we talked about. It's such an urgent and important problem about how you get ideas ideas to market in a profitable, effective way.

Andrea

Thank you. I'm in the stage of my life where I actually love to talk to people and love to work with people so they can literally email me at andrea at andreacates.com. And the website is andreacates.com.

And what's great about the way we designed the website is that there's a free diagnostic. So anytime you're feeling like, oh, my gosh, I need to do triage, you can take the diagnostic. It comes out different every time based on where you feel stuck.

And there's also tools that are customized that as soon as you take the diagnostic, you get a quick fix. You know, we send you something immediately like, oh, you're stuck at Build. You're stuck at Envision.

You're stuck. Here's a tool to get you started. And the final part is that we have a piece that's called What's Your Story?

And so what we're starting to do now is gather stories for the next round of From Stuck to Scale so that it's an ongoing process of understanding how success stories from one company and one leader and one individual can help others.

Scott

Andrea, it's been so great speaking with you and learning about your authorship journey, but also the incredible work that you do with some amazing leaders and organizations. It's been really compelling for me. And I know our listeners will have gleaned a lot from this conversation as well.

So thank you so much for being here.

Andrea

This has really been a great relationship. And I love co-creating with you and love being in conversation with you.

Scott

As we wrap up this episode of Entrepreneur to Author, remember this. Now is the time. Time to write.

Time to publish. And time to grow. I'm Scott McMillan.

Until next time.

 

Scott A. MacMillan


Scott A. MacMillan is a speaker, international best-selling author, entrepreneur, and the President and Executive Publisher at Grammar Factory Publishing. He and his team help expert entrepreneurs write and publish books that build their authority and grow their business.

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