In this episode of the AlchemistX Innovators Inside Podcast, host Ian Bergman sits down with John Rossman—former Amazon leader, strategic advisor, and author of Big Bet Leadership. Drawing on experiences at Amazon, T-Mobile, and as an advisor to top companies, John shares how leaders can build the second playbook necessary for transformational change in the hyper-digital era.
Here are the five key takeaways from their conversation:
John describes the hyper-digital era as a convergence of three massive forces:
Everyday operations and incremental innovation require one set of tools. Big bets—high-potential initiatives with significant risk—require another. John’s research highlights three habits of big bet leaders like Jeff Bezos, Elon Musk, Satya Nadella, and John Legere:
Drawing from Amazon’s “working backwards” process, John advocates writing and debating over endless presentations. Detailed narrative documents force teams to articulate their thinking clearly, challenge assumptions, and spot weaknesses early—critical steps for avoiding groupthink and stalled decision-making.
Transformational initiatives fail when they’re underpowered. Assigning a single-threaded leader—a senior executive fully committed to the exploration and de-risking of a big bet—ensures accountability, focus, and political capital within the organization.
The final recommendation in Big Bet Leadership is to become an active skeptic:
This mindset positions leaders to ride the momentum of disruption rather than be crushed by it.
If you’re a senior leader navigating rapid change, these takeaways from John Rossman’s Big Bet Leadership offer a roadmap for identifying, testing, and scaling transformational opportunities—before your competitors do.
Have a question for a future guest? Email us at innovators@alchemistaccelerator.com to get in touch!
Timestamps
📢 Introduction to John Rossman & Big Bet Leadership (00:00:00)
🌟 John’s Journey: From Amazon to Big Bet Leadership (00:02:14)
⚡ The Hyper-Digital Era & Why Transformation Fails (00:04:27)
📚 Case Study: T-Mobile’s Un-Carrier Strategy (00:15:59)
💡 Avoiding Groupthink & Creating Clarity (00:19:25)
🔒 Setting the Right Environment for Transformation (00:25:04)
💰 Cost Model Innovation & Applying Big Bets Beyond Tech (00:28:27)
📏 Continue, Kill, Pivot — Executive Oversight (00:33:37)
🎙 Rapid Fire & Personal Insights (00:39:38)
💥 Best Failure & Lessons Learned (00:41:50)
🎬 Closing Thoughts & Where to Connect (00:43:26)
00;00;17;27 - 00;00;40;07
Ian Bergman
Welcome to season six of Alchemist x Innovators Inside the podcast, where we explore the world of corporate innovation and dive deep into the minds and stories of innovation. Thought leaders crafting the future. I am your host, Ian Bergmann, and if you're an innovation agitator like me, then this is where you want to be. John, how are you doing today?
00;00;40;10 - 00;00;42;13
John Rossman
Ian, thanks for having me. Yeah.
00;00;42;13 - 00;00;54;08
Ian Bergman
I'm so I'm so thrilled you're joining us on Innovators Inside. I've been looking forward to this conversation, actually, and I, I feel bad because I don't think the audience is going to ever know this, but I think I accidentally rescheduled on you over the holidays. Is that right?
00;00;54;12 - 00;01;02;19
John Rossman
Oh, you know, as long as it's like, not at the last minute, but even then, like, you know, stuff happens. So it's a it's good innovators mindset.
00;01;02;19 - 00;01;13;23
Ian Bergman
We roll with it and we get going. Well. Well thanks for joining us for folks that don't know you you know let me maybe a brief introduction. John, you are in California right now. Is that right?
00;01;13;24 - 00;01;17;08
John Rossman
I'm in California. I'm kind of split time between Washington and California.
00;01;17;14 - 00;01;43;19
Ian Bergman
Awesome. Well, John, you are a distinguished author, strategic advisor, and keynote speaker. And your career, you know, a lot of the launchpad of your career was in the early days of Amazon, when I think some of the innovation principles and leadership principles were getting formulated. But you have, you know, translated some of that into practical advice, playbooks and tools for driving innovation inside a wide variety of corporate contexts.
00;01;43;26 - 00;01;47;27
Ian Bergman
And you've written on this and your latest book is Big Bet Leadership.
00;01;47;27 - 00;01;52;11
John Rossman
Is that right? That's right. Tell me about that book. So I always.
00;01;52;11 - 00;02;11;21
Ian Bergman
Like to start these conversations by getting to know my guests a little more. And I'd love to know a little bit about how you came to be sitting in the seat across from me, how you came to be, you know, thinking about this hard problem of corporate innovation. Yeah. And so, you know, maybe we start with the question of why this book and why now?
00;02;11;21 - 00;02;14;05
Ian Bergman
And we can weave in a little of your background along the way.
00;02;14;07 - 00;02;38;15
John Rossman
Yeah. Perfect. Perfect. So I was an early leader at Amazon. I got to play a key role in kind of launching and scaling the marketplace. Left Amazon in 2005. I was a partner at a firm called Alvarez and Marcel for 12 years. Great firm, a lot of great clients. One of them, the Gates Foundation, came to me. It's like, man, you do a nice job of delicately kind of taking their thinking and applying it into ours.
00;02;38;15 - 00;02;59;01
John Rossman
And my client, they're yours to write a book. So I wrote the Amazon way and kind of life changed, you know, and everything. One of the things I got to do along the way was to be the senior innovation advisor at T-Mobile. And my client there, Kevin McCaffery, who's the coauthor for big about leadership. He got to run new business incubation for T-Mobile.
00;02;59;01 - 00;03;36;28
John Rossman
So think of kind of new concepts, new value proposition, new customer use cases beyond the core wireless business. And what we did was we rewired and reworked a lot of the things from the Amazon playbook, the Amazon way, think like Amazon and some others specifically for the purpose of T-Mobile, which didn't want to be in the sun and wanted to go about developing kind of key concepts that had big potential, but we knew that they had lots of risks and unknown unknowns to them.
00;03;37;00 - 00;04;02;13
John Rossman
Sure. So we fundamentally built was kind of a an experimental based approach for how to approach these very different types of new value propositions, new go to market opportunities. We learned a lot along the way with that. And so big that leadership is, on one hand, kind of everything I've learned since I've left Amazon. On another hand, it's really baked around.
00;04;02;13 - 00;04;27;02
John Rossman
Some of the things we learned at T-Mobile. But why I think it's important now is. And so the subtitle of the book is Your Transformation Playbook for winning in the Hyper Digital ERA. Well, the preface of the book is like, what's the hyper digital era? Right? And so the premises and it can be agreed to or not agreed to, which is Netscape went public in November of 1998.
00;04;27;03 - 00;04;58;10
John Rossman
And really that's seen as like the starting gun for this digital era digital disruption and digital transformation and all that. And if you think that that era of almost 30 years now is been exciting and has had new winners or losers, it will be nothing like the next 25 years. And so I think we will look back at November of 2022, when ChatGPT was released as the next starting gun of a new era.
00;04;58;15 - 00;05;32;17
John Rossman
Right? And there will be a whole new round of winners and losers. And so the premise of the book is that we know we need to dramatically transform and change, but yet we're really bad at it. Yeah. But we've had 25 years of practicing it. Like, why aren't we getting better? And I think the premises fundamentally you need a different management style, a different management approach, a different operating system for these things that we call big bets.
00;05;32;20 - 00;05;58;05
John Rossman
Then you do your normal kind of everyday operations and kind of your incremental innovation and everything. Right. So fundamentally, a big bet is a something that has sizable opportunity to it. But you know that there are critical risks to it. And so this is a playbook on how to approach those unique opportunities for companies, which is fundamental transformation.
00;05;58;06 - 00;06;18;16
Ian Bergman
And I want to I want to get to more of the lessons in your book in a second, but I want to pick up on something that you just said, right. You kind of asked this question, this hypothetical or that why or rhetorical question really? Like, why aren't we better at this? We've had 25 years of practice, but we haven't really have we like that was the starting gun for an era that everybody just settled into.
00;06;18;17 - 00;06;33;14
Ian Bergman
And what you're identifying is that actually, you know, maybe we're entering a new era of change, or maybe the idea that disruptive, pervasive digital change may be coming more frequently in more directions now. And so we need to practice a bit more. Is that a fair statement?
00;06;33;17 - 00;06;56;10
John Rossman
Yeah. I mean essentially like competitive advantage is short in getting shorter. Yes. We know that we need to be able to to change and change, like for our customers, for our operating model, for our cost model, like in every way, we need to be able to change. But what we've proven is that very few companies are really systematic about how they do that.
00;06;56;12 - 00;07;21;17
John Rossman
And so we modeled the book off of four big Bet legends for leaders that we either worked for, had pretty good lens into how they operate, that we think have a fundamental, different M.O. about how they approach their transformation versus their everyday operations. And so those four big Bet legends are Jeff Bezos, who I worked for. Elon Musk.
00;07;21;24 - 00;07;47;29
John Rossman
Satya Nadella of Microsoft and John Legere of T-Mobile. And the central premise of the book is that there's three critical habits that these big that legends have relative to transformation, right? So everything is relative to kind of this concept of a major transformation. And those three critical habits that make them systematically success what it is, they create clarity, they maintain velocity and they accelerate risk and value.
00;07;48;01 - 00;08;08;12
John Rossman
And so the book is essentially a set of a playbook, a set of frameworks and actions to take to put those three critical habits in place so that you can both have high ambition, but approach them for what they are, which is fundamentally a bunch of risk that you need to test away early. And that's how we approach it.
00;08;08;15 - 00;08;09;18
John Rossman
Do you have to take.
00;08;09;25 - 00;08;20;24
Ian Bergman
Leaders or even just, you know, whoever readers or people that you're working with might be? Do you have to take them through a journey of getting them into a mindset to even be able to accept that there needs to be a behavior change?
00;08;20;26 - 00;08;27;24
John Rossman
What a great question. You know, I always say like, I'm I'm an engineer by background. Like, I really should have been a psychologist, you know, and everything, right?
00;08;27;25 - 00;08;29;23
Ian Bergman
Like, because I think there might be some overlap, by the way.
00;08;29;23 - 00;08;57;01
John Rossman
Exactly. But I always have to figure out, like, who's the person that I need to not just buy in, but to like to be the leader for this. Because if I can get, you know, there's an unlock there, right? And it really is about creating small patterns and awareness within a team, working that out and then working with them to replicate that.
00;08;57;01 - 00;09;23;24
John Rossman
Right. That that's that's fractal theory of change in motion. And and so the answer is yes. And to some degree that's back to why I wrote this book. I wrote this book so that in on one hand, people that I'm working with, teams that I'm working with, they I can bring them quickly into an at depth conversation. I'm like, oh, so this is the journey.
00;09;23;29 - 00;09;46;24
John Rossman
Here's how we're going to go about it. Here's both principles and tactics for how we do it. We can agree or disagree relative to those, but at least we're clear about it, right? And so I can fundamentally understand the things that I am expert in as an operational leader aren't just inadequate, they're likely wrong and cause harm when it comes to major transformation.
00;09;47;01 - 00;10;07;09
John Rossman
And if I can get them to agree on that to your point, then it's like, okay, now we've identified the enemy here in everything, right? Which is everything we've learned. We're going to go through a set of practices in order to step down the staircase into how to actually be a transformational leader.
00;10;07;14 - 00;10;26;16
Ian Bergman
Yeah, and I love that you said that because I think I think that is it is incredibly important the notion, right, that there the incentives, the efficiencies, the processes that create, you know, value at scale and enterprises run counter to innovation. Like, I think we can all wrap our head around that, right? We can all read Innovator's Dilemma.
00;10;26;16 - 00;10;29;17
Ian Bergman
We've all worked or lived in large companies and, you know, blah, blah, blah.
00;10;29;18 - 00;10;35;22
John Rossman
And we know all know the short term incentives and and mindset that's in place, right?
00;10;35;24 - 00;10;51;22
Ian Bergman
Absolutely. But that is a very different thing than what you just said, which is an acceptance, a level of acceptance that actually what I am doing as a person, as a human, as a leader, might be counterproductive to the risk taking and the risk portfolio that I want to build.
00;10;51;28 - 00;11;23;17
John Rossman
Yeah, we wrote this book specifically for senior leaders and the teams that support senior leaders in building you know, whether it's their new business incubation team or their strategy team or their digital transformation team or their AI team, like whatever team it is and the senior leaders, this book is written for that job right there. There's lots that was has been written about kind of the individual contributor and kind of the methodology of agile and lean and everything.
00;11;23;17 - 00;11;34;21
John Rossman
Right. But but we couldn't really identify anything. That's like as a senior leader, what do I need to do differently in my job relative to major transformation?
00;11;34;21 - 00;11;43;13
Ian Bergman
And it's one of the hardest things to answer with precision, because it's easy to hand wave, you know, and say, like, oh, like enable learning from failure. You know, but like.
00;11;43;15 - 00;12;25;20
John Rossman
And and that is exactly it. And so not that we nailed it completely, but at least we give fundamentally identify the problem, have a stated principle and then a set of tactics that that put that principle into place. That's how we fundamentally approach the book. For those senior leaders and the teams that support them on what they need to personally do different, because as I mentioned, like, I'm an engineer, not a psychologist, but I need senior leaders to actually understand the power of their individual mindset behaviors and where they spend their time as it comes to why this happens, because I think we kind of glad hand.
00;12;25;20 - 00;12;53;24
John Rossman
It's like, oh yeah, leadership matters in like no senior leadership matters the most, you know, and everything. Right? And they fundamentally do need to understand the situation. But you know, we talk about wicked problems in the book. It's a wicked problem in that, you know, that these these transformation actions and innovations have an extremely high failure rate. But yet we know we have to do something different.
00;12;53;24 - 00;12;59;27
John Rossman
We know we have to transform or we are living on a on a melting iceberg here.
00;12;59;29 - 00;13;14;29
Ian Bergman
Burning platform, whatever you want to say. I think one of the most interesting things that I have come to realize is how many very, very smart senior leaders take their organizations off the cliff with the with their eyes wide open. They know what's happening.
00;13;14;29 - 00;13;16;04
John Rossman
Nobody's like you.
00;13;16;05 - 00;13;19;01
Ian Bergman
If you're a if you're a leader of an organization, you are not a stupid person.
00;13;19;06 - 00;13;45;00
John Rossman
Yeah. I mean, a great story. You know, Howard Schultz, kind of founder, a long time CEO, recently did an extended interview and, you know, about kind of what happened at Starbucks and everything. And, and what he said was, was a clinical diagnosis for most enterprises. And what he said was that, you know, we stop playing offense and we just went into risk mitigation mode.
00;13;45;02 - 00;14;14;24
John Rossman
And that's the worst thing that a company could do. And it got blended with hubris, right. We started to think we're better. I think the innovator's dilemma won't happen to us. We know what we're doing, you know, and everything. Right. And and it's as simple as that, which is they don't invest enough resources or their own personal time and attention to inventing the future, substantially new future as they do run in today's business.
00;14;14;24 - 00;14;37;04
John Rossman
And that's a real simple choice that you need to make as a leader. And one of the things that I've gotten to see in firsthand from Bezos and other senior leaders who are really good at this is their personal time and attention. And the way that they operate in inventing the future is significant, and it's different than how they approach operations.
00;14;37;08 - 00;14;47;03
John Rossman
Yeah, and that gets back to the two playbooks you need. And most companies, most leaders don't really understand that second playbook kind of that reinvention playbook.
00;14;47;06 - 00;14;57;12
Ian Bergman
And there's so many such easy traps to fall into there in terms of, you know, the, the, the urgent versus the important, the responsibility to stakeholders.
00;14;57;15 - 00;15;15;17
John Rossman
It tends to be death by a thousand cuts. And there's always a postmortem. And they, you know, they try to boil it down to like one thing that went wrong. And it's typically it's like, yes, that's true, but there's a bunch of other things that were also not in place to be supportive for this. And so it is a playbook.
00;15;15;17 - 00;15;28;26
John Rossman
You can't have just one simplistic notion of like, well, okay, this is what I need to do. I need to have an agile methodology to, to, to be successful at this important but not enough. Well, so.
00;15;29;04 - 00;15;49;24
Ian Bergman
I want to get into some of the playbook in a second. But first, you mentioned that a lot of these lessons are derived from for pretty amazing leaders. I suspect most of the audience is familiar with Nadella, Bezos, Musk, John, there is a little bit more under the radar. I, you know, I love absolutely. I'm obsessed with what he did at T-Mobile and some of the era you were working with them.
00;15;50;01 - 00;15;50;22
John Rossman
But can you.
00;15;50;22 - 00;15;59;11
Ian Bergman
Share a little bit about what you saw and maybe some of the more unique or colorful things that he brought to the table in how he set up his leadership and focus on the future?
00;15;59;18 - 00;16;24;26
John Rossman
Yeah. So just to be clear, John had left the business when Kevin and I were working there, but you still lived under the umbrella of of his impact and, and how we operated. But we opened the book honestly with, with the 2013 Consumer Electronics Show, where he announced a war against the legacy cell phone carriers. Right. And the Uncarrier.
00;16;24;26 - 00;17;07;20
John Rossman
Right. The Uncarrier moves. And so over the next eight years, they made a series of, I think it's 12 branded Uncarrier moves to reinvent their value proposition. And they went from a laggard fourth place, suffering inconsequential telecommunications cell phone telecommunications firm to the market leader and the perceived leader, and then the perceived brand leader for a company that loves its customers and is at the forefront of innovation and in cellular communications and so they created an enormous amount of enterprise value in doing that.
00;17;07;20 - 00;17;41;10
John Rossman
And really, you know, they went from, again, the fourth place carrier to, you know, the first place carrier. And so that is a fundamental repositioning style big bet that he did. And and that's why he's he's not just in the book, but he leads the book because that took bold communication. So the book is based off of kind of the framework to put across this whole life cycle is what we call the big that factor, which is name the problem and your hypothesis for the future state.
00;17;41;11 - 00;17;52;12
John Rossman
And that's what John Leger did was he named the problem and he framed, here's where I am taking you. And then he drove that big bet vector across the organization. Yeah.
00;17;52;18 - 00;18;17;23
Ian Bergman
And he also, boy, we're going to come back to this because like the problem hypothesis iterate like yes. But you know, he named a problem that kind of pointed back to himself in a mirror or, you know, he named he named us. He named us as the telecom industry, as a problem. That must have been very hard. Do you have a sense of, you know, could could he have actually gotten the buy in?
00;18;17;23 - 00;18;24;12
Ian Bergman
Could he have actually shown that leadership if they hadn't been in this distant fourth place position, if they had been where AT&T or Verizon, where.
00;18;24;15 - 00;18;54;04
John Rossman
I doubt it. You know, their strong shareholder was Deutsche Telekom, and everything and a pretty conservative group. And they, they really saw this as just part of their investment portfolio. And so I doubt that if they had been kind of winning per se, that that he would have had the ability to kind of go for a, you know, burning platform strategy relative to this.
00;18;54;04 - 00;19;06;17
John Rossman
So, you know, that's that's conjecture in everything. But I think having nothing to lose, maybe more or less to lose, played a role in his ability to do that. I mean, I.
00;19;06;19 - 00;19;25;01
Ian Bergman
I think like that rings true there. I think there has to be some truth to it. And the fact that, you know, crisis actually brings out willingness to change. But I want to connect to this. And this might not be the most elegant of Segways, but I'm going to try anyway. Like, I want to connect this to one of the pitfalls that you discuss in the book.
00;19;25;01 - 00;19;45;20
Ian Bergman
And these are pitfalls about groupthink and analysis paralysis. Right? Like all of our tendency as leaders to try and build a certain amount of consensus and also, you know, to think through the problem and I think, you know, I think that's a natural state of affairs when you are a leader in your category and you are considering a change.
00;19;45;27 - 00;19;54;07
Ian Bergman
So, you know, how do you think about that trap? And what are some things that leaders who are not in crisis might want to keep in mind?
00;19;54;10 - 00;20;22;29
John Rossman
So these things fail for lots of reasons, like they fail because we don't think critically enough. They fail because we we think too long and we all think alike and everything. But I think the biggest reason they fail is because we see the outline of a fuzzy outline of an early opportunity, and we all just go, yeah, we're going for it, you know?
00;20;22;29 - 00;20;53;21
John Rossman
And everything. Right? This kind of describes the GE predicts, you know, digital transformation that that they went after. And what we encourage teams to do like it's it's rarely the lack of having a good idea. The problem is you typically have way too many ideas. Yeah. Or different subtle versions of the same idea. But we get kind of lazy and we, we tend to like, yeah, that's the idea.
00;20;53;21 - 00;21;21;05
John Rossman
And we go and we commit to it upfront. Right. And what you should commit to is we're going to experiment on this idea like we think this is the the high value problem. We think this is the killer feature and the future state. What we commit to is de-risking this thing. And then we can allow it to do what it should do, which is either change, adjust, pull back, continue, experiment, or go big.
00;21;21;05 - 00;21;51;17
John Rossman
You know, like one of those things, right. And so these things start off fundamentally with a fuzziness that actually is is tremendously harming, throughout the entire life cycle. So if we can create clarity, that's why the first critical happened is create clear if we can create clarity and kind of test this thing out just by writing and debating, writing and debating on it, you start with a tremendous advantage of speed and clarity of thought.
00;21;51;18 - 00;22;16;13
John Rossman
We want both of those things. And so this is modeled after Amazon's working backwards approach. We we got really specific for for teams and companies that aren't familiar with how to write a narrative six pager or an FAQ. You we we gave give you specific templates and memos to write that help elicit out like what you need to do.
00;22;16;15 - 00;22;36;03
John Rossman
But writing and debating, writing and debating, writing and debating like that is the fundamental principle of how we tackle both a lack of critical thinking and analysis paralysis and groupthink as part of all of that. And do you.
00;22;36;05 - 00;22;59;25
Ian Bergman
Believe that the convicted innovation leader, the convicted leader who believes that we need to do something different, has to put that first stake in the ground on what to write like? How do you start that cycle and maybe, maybe ask it a little bit more specifically, who is accountable for first defining the problem in such a way that the team can start to grapple with it and can start to iterate?
00;23;00;04 - 00;23;26;24
John Rossman
Yeah. So clearly, like a small focus team to drive this effort. But then syndicate that conversation against a broader group is is kind of the critical pairing that has to be made. So we talk about the concept of a dry or directly responsible individual who leads this effort within an organization. Kevin McCaffrey was that individual at T-Mobile, right?
00;23;26;27 - 00;24;03;17
John Rossman
Amazon uses the language of single threaded leader, a senior leader who is senior enough to actually have sway and and know how within the organization and ecosystem. And so, you know, typically what happens is these these initiatives, they get way underpowered. They get like you have mid-level project managers that are leading the effort, and nobody is truly accountable at a senior level for deeply paying attention to this precious little baby that we're trying to bring along.
00;24;03;17 - 00;24;24;11
John Rossman
Or, you know, right, and debate about and everything. And so having a senior enough leader who is ostensibly fully committed to the exploration of an idea or portfolio of ideas, I think is one of the most controllable factors you have and whether you're going to be successful at this game or not.
00;24;24;13 - 00;24;29;10
Ian Bergman
And is that a title? Is that a job description? Is that a, you know.
00;24;29;14 - 00;24;37;16
John Rossman
Framing of discussions? It can come in many titles, but it should be part of the job description. Yeah, it's really easy.
00;24;37;16 - 00;24;56;03
Ian Bergman
In my experience, for people who have some of the titles or might be talking about, it could be a chief innovation officer, could be a director of new business incubation, whatever to get sidelined a little bit and maybe castigated a bit as the people who get to have fun and play with shiny objects, you know, at the cost of the rest of the business.
00;24;56;04 - 00;24;58;12
John Rossman
Absolutely. What?
00;24;58;14 - 00;25;04;14
Ian Bergman
Like what? What do we do about that? That feels like only the leader can control it. But it's a it seems to be a pattern that repeats itself.
00;25;04;15 - 00;25;26;25
John Rossman
Yeah. There's a bunch of, I think, kind of constraints. And you know, the the second section of the book is big but environment and it's really about how to set up a team and the conditions under which they can succeed. And then the third section of the book is big, that management, which is about like what you need to do to maintain governance and keep the tension in the wire relative to.
00;25;26;26 - 00;25;53;01
John Rossman
So there's aspects of both of those sections that address this question. But I think at the end of the day, you just have to have good hygiene, good disciplines around your portfolio and how you debate, approve and kind of make the the stage gate, the steps towards progressing against a specific idea because they fail for so many different types of reasons.
00;25;53;01 - 00;26;24;15
John Rossman
But that's why, you know, the second principle is maintain velocity. You have to maintain kind of the crispness of pace plus critical thinking and action relative to it. So the team has to be empowered. They have to have enough tools at their at their fast beck and call that they, they aren't always running into, you know, an 18 month roadmap for somebody to do or, you know, a procedure or a process or rule that really slows it down.
00;26;24;15 - 00;26;49;27
John Rossman
Like you really have to create a cocoon that allows them to do this fast job of kind of testing and iterating big concepts in their business. And, you know, that's what allows a team to do the job, is having both that sense of urgency and constraints put on them and giving them a chance to be successful at it.
00;26;49;27 - 00;27;11;07
John Rossman
Like so many times, we we tie an arm behind them and tie a brick to them and tell them to to swim really fast. It takes a combination and it's and again, it's like it's it's too simplistic to say like, oh, we need to have just a senior leader. No. Like you need all of these things in place in order to be successful at that.
00;27;11;09 - 00;27;33;27
John Rossman
And that's why most, you know, the mistake that most companies make is they start off with a grand ambition, but then they just naturally, because we're humans, they start de-risking it by pulling back on the ambition of it. And that that allows us to say like, yeah, the system, the system, the technology got implemented. But it's like it.
00;27;33;27 - 00;27;34;26
Ian Bergman
Didn't change anything.
00;27;34;26 - 00;27;37;24
John Rossman
Didn't make it. Did the universe notice, you know, and everything.
00;27;37;29 - 00;27;53;21
Ian Bergman
Right. You know, okay. I actually love that. Like did the universe notice should be a heuristic for, you know, a lot more people I think than than it really is like you may love or hate them, but that feels like a heuristic that is in the back of Elon Musk's mind every day.
00;27;53;23 - 00;28;27;17
John Rossman
Amen. Amen. And so I agree completely. Like you can love him or hate him and you can also be worried about him, but what all of his companies do, one of the things that I think is most interesting that they do is they always look at cost model innovation to pair with a killer customer value proposition. So that's one of the things we tease out here is you have to have both a great customer value proposition and a cost model advantage for a truly transformational market to develop.
00;28;27;23 - 00;28;53;03
John Rossman
Because if you can have a cost model innovation at some point, these things consume a lot of resources and you and converting customers is very different than delighting current customers, right? If you actually want to get customers to convert, it has to be you have to be thinking of has to be ten x better? Yes. Well, it's easier to be ten x better if your product is better and it is substantial less.
00;28;53;03 - 00;29;17;24
John Rossman
So you look at what SpaceX or Tesla or The Boring Company. All of those have a fundamental focus on unit cost innovation at a significant cost. And so they put a target cost model out there to start with. And then that really drives their experimentation. How do we get how do we prove out that we can get to this target cost model.
00;29;17;26 - 00;29;20;00
John Rossman
So let's let's move away.
00;29;20;00 - 00;29;50;14
Ian Bergman
From kind of the tech sector or tech adjacent sector for a second, because I think that's such an interesting it's an interesting point. And let's, you know, I don't know, let's go to something boring. Let's go to manufacture actually professional services like I think there's a lot of professional services leaders that are looking at their input cost model, which is maybe a lot of very expensive labor, and saying this doesn't feel right and sustainable, but my entire business is built on the funnel of Wharton grads, whatever it might be.
00;29;50;16 - 00;30;08;26
Ian Bergman
How do you break out of this deadlock where, you know, you know, in your head, okay, tech is capable of magical things and it'll be more magical tomorrow and I can do anything, blah, blah, blah. And you know that there's going to be a competitive disadvantage that's coming, but you feel locked into your cost structure for good reason.
00;30;08;28 - 00;30;31;28
John Rossman
Like how do you get out of that? Yeah, yeah, it gets even more complex in that. So I was a partner at Arthur Andersen before Amazon was a partner and a really good partnership. Alvarez and Marcel for 12 years after Amazon. So I know the consulting and partnership model and and the challenges are more than just the the young pipeline challenge.
00;30;31;28 - 00;31;01;01
John Rossman
It's it's also the partnership model itself. Yeah. Is fundamentally like most things, both its strengths and its potentially fatal flaw relative to it. And, you know, a real transformation takes us fundamentally rethinking from the market standpoint, like what's the problem your customers are trying to solve for. And if you could zero based design how to help them solve that problem.
00;31;01;01 - 00;31;36;23
John Rossman
Like how would you do it without constraints, without the burden of your legacy business. So just have that unconscious, drained thinking exercise to do. Now start applying the constraints maybe of kind of your organization, your brand, where you're at, and then you start testing out. Well, am I, am I fundamentally up for like if I believe that this is the future of, you know, professional services or whatever kind of your expertise is, what's the best way to a test that out?
00;31;36;23 - 00;32;22;02
John Rossman
Because I think it's that. But I'm not sure yet. You know, in everything. Right. And what are the real risks relative to getting there? Is it my ability to deliver it? Is it the limitations of my brand? Is it the limitation of my of my talent pipeline? Like what are the real risks relative? And in a lot of cases, I think that a situation like that is going to take, you know, doing some type of skunkworks like off brand trial to test and learn something out, evaluate, and then and then understand like, well, how do I transition that into my current stakeholders and shareholders and, and my current brand and business model.
00;32;22;02 - 00;32;33;24
John Rossman
And I think what a lot of them are going to find is like, yeah, we we maybe need to launch a whole new model because the legacy model has too much along with it. Well, and that.
00;32;33;26 - 00;32;52;27
Ian Bergman
You know, I, I think for any of us, we, you know, we can kind of count on however many fingers and toes we have, the number of really transformational enterprise level kind of success stories. Right? But a lot of the ones that I feel like I have seen, that's been the model, as in they have launched an adjacency business.
00;32;52;27 - 00;33;02;26
Ian Bergman
They have let it compete with the core business. And at some point you just wind down the core business. But that's an incredibly hard thing. I've seen that in insurance, for instance.
00;33;02;26 - 00;33;23;15
John Rossman
It is incredibly hard. Absolutely like that. That is the point of these is that they are hard. They are complex. But if the way you manage it is by pulling back on the ambition, like you're you're just, you know, maybe pushing out the melt a little bit, but it's still melting here.
00;33;23;18 - 00;33;37;20
Ian Bergman
So let's talk about this executive oversight to keep things going. What are some of the principles of kind of really good innovation leadership to keep. You know what I'm talking about C-suite or CEO level leadership to keep a project like this on track.
00;33;37;20 - 00;34;04;23
John Rossman
Yeah. So we kind of talk about three key things. And the first is a chapter called continue Kill Pivot or Confusion. And it's it's about the high stakes moments where you're making, you know, you're down the path on some concept here. And so you're making a decision relative to I kill, do I pivot, do I continue, do I scale.
00;34;04;25 - 00;34;35;15
John Rossman
But what typically happens is there's actually confusion that falls out of that. And it's because we don't have good hygiene about how we run that meeting and the job to be done at that meeting. It's not an audit. It's not anything other than here's what we've learned, here's where we're at. What do we think the next best move is relative to this proposition and declaring and defining that out loud repeated.
00;34;35;18 - 00;34;42;25
John Rossman
Make sure that there's no confusion about the decision. So that's that is about what that chapter is about.
00;34;42;25 - 00;34;45;02
Ian Bergman
Are you allowed to defer a decision?
00;34;45;04 - 00;35;05;17
John Rossman
Yes. If it has good hygiene and specific next steps to like, well, what we want is more information on this point, you know in everything. Right. And so so that's a nuance of kind of continue which is like go get me this point, answer this question and test this concept out as a deferral point and everything.
00;35;05;20 - 00;35;24;16
Ian Bergman
So I want to step back for a second because obviously the, you know, the topic of innovation and the topic of R&D has been around for a very, very long time and in many forms. It feels to me more important now. And I want to see feel free to agree or disagree, but it feels to me.
00;35;24;16 - 00;35;53;00
John Rossman
That's kind of the premise of the book to some degree. Is is in a monumental manner, and it's not driven just by AI. There's change everywhere. We think that there are three mega forces that are really going to drive this hyper digital era. One is technology, AI in particular. The second is the aging of our population, and the third is the is the competition for capital driven by the indebtedness and the committed spend of our countries.
00;35;53;02 - 00;36;28;01
John Rossman
And if you put those three mega forces, each one a Significa inside clone, but together it's going to create this vortex of both opportunity and disruption. So I frame named and claimed that problem, which we call the hyper digital era, which is going to make that the the change ten x and and the premise my belief is, is that you are going to see companies that are fundamentally engineered for 10 to 100 X levels of productivity.
00;36;28;03 - 00;37;01;21
John Rossman
Then a similar company, well-run company, is today. And I think that is happening now. And that set of mega forces are tied together, but with a fuze. And that fuzes capital that to at play to invest in those companies with aggressive playbooks to take down the incumbents. And so that is why I agree and magnify your observation, which is this is a dramatically more important conversation now and going forward.
00;37;01;23 - 00;37;02;05
John Rossman
You know.
00;37;02;06 - 00;37;26;09
Ian Bergman
Those of us in the startup world have been waiting for what feels like the inevitable solo unicorn, right? That small team or solo individual whose productivity is so amplified that they build that billion dollar plus business. Right. And I think writ large, I think there's a lot of that disruption coming. But what what strikes me is that it's not just that this is important because there's more challengers.
00;37;26;11 - 00;37;44;18
Ian Bergman
It's important because the future is actually murkier. You can see these forces, but the impact of the forces, like we we don't know, we nobody can actually tell you what OpenAI, Deep Seek anthropic or anyone else are going to be capable of in 12 months, not even in those teams. Nobody knows what the downstream, second, third, fourth order impacts of those are going to be.
00;37;44;18 - 00;37;52;16
Ian Bergman
So, you know, as corporate leaders, it strikes me that part of this conversation is about setting your organization up.
00;37;52;16 - 00;37;53;15
John Rossman
To prepare.
00;37;53;15 - 00;37;59;02
Ian Bergman
For whatever the uncertain future might be, rather than planning for what you believe it will be. Does that ring true?
00;37;59;09 - 00;38;27;17
John Rossman
Yeah, absolutely. So we the last recommendation in the book is to be an active skeptic. So active meaning you can't just watch this stuff happening. But skeptic meaning don't just believe that either. Like you actually have to test these things out. So you need to appropriate the right amount of resource and the right technique. You need to be an active skeptic in order to be successful at this, and to take advantage.
00;38;27;25 - 00;38;35;03
John Rossman
Like your goal is to ride the momentum of these forces versus being buried by the momentum of these forces.
00;38;35;05 - 00;38;54;13
Ian Bergman
I love, I love that, and I think that's a really interesting kind of metaphor to to end this segment on, we want to be able to ride those. So kind of to close out this little, this little piece of the podcast. One question for you. And it's maybe a hard question, maybe a really simple one.
00;38;54;16 - 00;38;55;06
John Rossman
What do I as.
00;38;55;06 - 00;38;59;11
Ian Bergman
A leader do first, if I have listened to this and I am correct.
00;38;59;14 - 00;39;21;12
John Rossman
We think about leadership. There it is. Here's what I would do. First is come up with 3 to 5 really difficult problems that either your customer faces or your operating model faces. Put a name and write out one paragraph on those three really hard problems. That's the.
00;39;21;12 - 00;39;22;28
Ian Bergman
Start. Love it.
00;39;23;00 - 00;39;23;23
John Rossman
Well.
00;39;23;25 - 00;39;38;28
Ian Bergman
John, I'm going to take us in a very different direction for just a few minutes here, if that's okay, because I want to get to know you a little bit more. And sometimes this pulls out some really interesting stories. So I'm gonna ask you two to bear with me for a little bit of a game. I'm going to ask you some rapid fire questions.
00;39;38;28 - 00;39;40;04
John Rossman
Answer quickly.
00;39;40;05 - 00;39;41;29
Ian Bergman
No thinking, and then we'll see where it takes.
00;39;42;03 - 00;39;46;06
John Rossman
So I'm good. I'm a professional thinker. Like, okay, I'll try to turn off the bat.
00;39;46;07 - 00;39;53;08
Ian Bergman
Right. It's trust me, it's tough. We're all a little too cerebral. But let's start with the easy one. You're an Apple or Android guy?
00;39;53;11 - 00;39;54;05
John Rossman
Apple.
00;39;54;08 - 00;39;58;19
Ian Bergman
And are you a remote or in-person work person? Remote?
00;39;58;19 - 00;40;04;05
John Rossman
I work for myself. I'm either flying to see my client or do a keynote, or I'm working from home.
00;40;04;07 - 00;40;11;02
Ian Bergman
Well, let's talk about that. So you do you collaborate with clients, with partners, with people all the time. You know, how does that work? Remote.
00;40;11;04 - 00;40;31;09
John Rossman
Well, I do a lot of workshops. And so what we tend to do is get together for a couple of days, really attack something with focus, and then we have a couple of weeks of individual work and some meetings, and then come back together for a workshop to kind of wrap it up. And that balances out kind of that analysis paralysis, keeping speed, keeping focus and everything.
00;40;31;11 - 00;40;44;14
Ian Bergman
Yeah, that makes sense. I, I feel the desperate need to get out of the basement that some of my listeners who are watchers, I should say, are a little familiar with. And it is really important. How do you celebrate wins?
00;40;44;17 - 00;40;45;25
John Rossman
Personally for you.
00;40;45;25 - 00;40;47;05
Ian Bergman
Yeah. Or with your clients?
00;40;47;09 - 00;41;11;24
John Rossman
Well, yeah, with my client, it's all about communication, right? And so, like, communicating. Not just what was accomplished, but why we were successful at this and everything. Right. And so the kind of that, like, what lesson do we learn relative this. But personally, like, how do I celebrate a win? Like I just like to have dinner with my family, you know?
00;41;11;24 - 00;41;15;21
John Rossman
And that may sound trivial, but it just means everything to me.
00;41;15;24 - 00;41;24;10
Ian Bergman
There's no such thing as trivial time with your family. But also, I think there's no such thing as trivializing, you know, a moment of celebration.
00;41;24;10 - 00;41;31;14
John Rossman
I agree, I agree, and I'm probably not very good at that. Like that's a fair observation.
00;41;31;17 - 00;41;44;24
Ian Bergman
Well, I yeah, I'm not here to critique you, but look like hypercritical skepticism seems to go with hyper self-critical skepticism seems to go with kind of some of the most innovative and hardest pushing people. And I do think it's important to take that moment to celebrate.
00;41;44;24 - 00;41;45;17
John Rossman
Okay, great.
00;41;45;19 - 00;41;50;22
Ian Bergman
But okay, so I got two more for you. What's your best failure?
00;41;50;25 - 00;42;30;17
John Rossman
So my best failure. So I and I write about it in big Bet leadership, which was I got to be part of a big bet driven from the Gates Foundation. It was about a a movement, a platform, a capability to reinvent classroom education through individual cohort delivery capability. And we had all the best architecture, all the best technology, but the communication plan and the community engagement plan and the teacher union engagement plan was underplayed.
00;42;30;20 - 00;42;49;10
John Rossman
And that's when I really saw the power of PR, the power of really thinking through incentive systems and how critical that is when you're really thinking about ecosystem changes with bought in stakeholders.
00;42;49;13 - 00;43;05;28
Ian Bergman
Yeah. And people and, you know, remembering that people are people and that this is not a just an engineering function. I actually love that. Okay. Well then I've got one more question for you, John, and then we'll we'll get to close. Can you define innovation in one sentence?
00;43;06;00 - 00;43;11;09
John Rossman
Yeah. It's the ability to think and deliver something that is better than today.
00;43;11;11 - 00;43;26;23
Ian Bergman
That's the most concise answer I've ever gotten. I love that, John. It's been an absolute pleasure having you on innovators inside for folks who want to keep in touch, you want to get Ahold of the book, but maybe also some of the tools and the frameworks from the book, like where should they go? Where should they follow you?
00;43;26;29 - 00;43;46;18
John Rossman
Yeah. So LinkedIn by far the easiest way to get in touch with me. Big bet leadership.com is where you can get kind of all the frameworks directly from the book and then the books, you know, gorgeous hardcover book, Kindle and a really delightful audiobook. So get that at Amazon or your other bookstore.
00;43;46;20 - 00;43;58;13
Ian Bergman
Amazing big bat leadership.com. It's all going to be in the show notes John Rosman, author, advisor, and Experienced operator and innovation, thank you for joining us on Innovators Inside.
00;43;58;15 - 00;44;00;03
John Rossman
And great to get to know you.
00;44;00;06 - 00;44;22;20
Ian Bergman
Cheers. And that's a wrap for today's episode of Alchemist x Innovators Inside. Thanks for listening. If you found value in today's discussion, be sure to subscribe to our podcast and check out our segments on YouTube. Links and follow ups are in the show notes, and if you have questions you want us to feature in future episodes, email innovators at Alchemist accelerator.com.
00;44;22;23 - 00;44;27;14
Ian Bergman
Stay tuned for more insider stories and practical insights from leaders crafting our future.