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Our transcripts are generated by AI. Please excuse any typos and if you have any specific questions please email info@digitalshelfinstitute.org.
Welcome to Unpacking the Digital Shelf, where we explore brand manufacturing in the digital age.
Hey, everyone, Peter Crosby here from the Digital Shelf Institute.
I don't know about you, but I feel like there's a distinct sense out there that we are at the precipice of another era-defining change in commerce, business, and even societies.
A moment where leaders will be called to envision and enable the big transformations necessary to survive and thrive.
In business, we call that making big bets, and getting good at them is more critical than ever.
That's why John Rossman, author of The Amazon Way and Think Like Amazon, has co-authored with Kevin McCaffrey, former strategy head at T-Mobile, a new business playbook called Big Bet Leadership, your transformation playbook in the hyper digital era.
John joined Lauren Livak Gilbert and me to introduce his clear, concise, and actionable treatise for driving the change your organization needs for this next era.
John Rossman, welcome back to the podcast.
Thank you so much for being here with us today, and congratulations on your book.
Well, Peter, Lauren, it's great to be here.
The Digital Shelf is such a great community, and I appreciate the opportunity to come and talk today.
Well, I have to tell you, reading through your remarkable book on how to pull off Big Bets, there are a lot of business books.
You it's the first sentence, I think, of your book, actually.
There are countless books that make the case for digital transformation, etc.
And you know, my thought, because I know you, I knew I would get something fresh and new.
But I was thinking to myself, well, how do you do something fresh and new on here?
And one of the things that really pulled me into the urgency of getting this right was you started off by naming three mega-forces that shape the next period of time that is forcing, I mean, not just businesses, but entire populations to change the way we work, live, create.
And they were generative AI and quantum computing, the aging of America's workforce, and the changes that that rots and the opportunities, hopefully, and then the growth and spending on entitlement programs, which will have to change the way we create value and drive results in.
All three of these are both opportunity and challenge.
And to me, they were a gut punch for, holy crap, we have to get better at Big Bets, and our listeners need to, if their companies are going to survive, and if frankly, our cultures are going to survive.
Is that what you were thinking with that?
It really is.
Each of those mega forces is a cyclone to deal with, but I think that they combine together, and the general premise is, if you think the last 25, 30 years of digital transformation has been exciting, you're not gonna see.
The next phase is really coming at you, and that's what I frame as the hyper digital era.
And what I think is primarily gonna be the big difference is that the customer experience has been really greatly reinvented, a bunch of cool technology.
But if you look at productivity and how work actually gets done in mid to large companies, it really hasn't changed that much, right?
It's been a fairly slow, incremental productivity change and operating model change.
I think that is what's going to be the distinguishing feature.
In 25 years, when we're looking back, it's like, oh man, we reinvented productivity.
And so there are going to be companies that have 10 to 100X productivity.
Like what it takes to get something done is going to be completely transformed and changed.
And that's what we have to prepare for.
And we know we're not good at these things, but we're going to have to get good at it.
And this is what's going to separate out the long-term winners from the long-term losers.
I love that.
And I will call you 25 years from now so we can laugh about it all.
Yeah, I'm going to have the kids pulled off.
Yeah, the great thing is that nobody will be calling me on this prediction in 25 years, right?
Well, no, there'll be a chip in our heads and I'll just beam my thoughts to you.
And that's what's so, for me, bracing about the book is that it really lays out, takes from a bunch of resources, but also your experiences.
You went through a big bet at the Gates Foundation that didn't work.
And I feel like that experience has contributed and all the other companies that you've consulted with and just your own thoughts and those of your co-authors.
But it feels like that experience is what almost drove you to not want other people to have to go through that.
Is that fair?
It is.
We wrote this book both for companies to succeed at their big bets, but also for the people that are involved with them, because there's nothing better to have your career positively impacted by a big bet.
And it can be a real derailment to a career to be associated with a failed big bet.
And so I wrote this book for two specific personas, but then kind of the people around.
The two specific personas are the senior leader who is accountable for pulling off a major transformation and the directly responsible individual that tends to be the fully committed individual leading the transformation.
Those are the two specific personas that we wrote this book to, plus all the people that support or are involved in the effort.
But those are the two kind of target customers for the book.
Yeah, well, I think our listenership is probably a combination of the two, but I would say they're a lot in the second, where in the next couple of years or few years of Big Bets, they'll be that person, but then they will be, because of those Big Bets paying off, they'll be the ones that are deciding what the next bet should be.
So it's an exciting time for this to be discussed.
You know, one thing I like to be really clear about is like what a Big Bet is, and that this book isn't for every situation and everything.
A Big Bet is a strategy initiative, a plan, an objective that has these two key attributes.
One is that it has high ambition, has the potential for truly impacting our business.
And that can be at the enterprise level, that can be at a team or capability level, but it has high ambition.
And the other attribute is that it's multi-sided in risk and complexity and stakeholders, right?
And so those two things are what make a Big Bet unique.
And so incremental straightforward projects, super important, nothing wrong with them, but they're not a Big Bet.
They don't have that type of complexity and that tension between high ambition and multi-sided risk.
Yeah, and the potential to really transform the operating model and the success of the business.
Yeah, exactly.
And John, I was just going to say, I think even if it's not the Big Bet that has the high complexity, I like the way you broke down thinking through it, like the wicked problem, the environment that you're in.
Like I love that way of thinking.
So I think it's also helpful as anything that happens in digital is new and is a test and learn, and we don't necessarily have the end result of what it's going to look like.
So using this way of thinking to just say, what are we trying to solve?
What's the actual problem?
How do we get the rest of our environment?
People process technology on board.
So I really like that aspect too, because you can apply it to just thinking about new things in digital like AI or retail media or anything new, name 17 new things that will come out in the next five years and how to tackle those problems.
Well, I think, so I agree with you.
I think there is some definite aspects of this that can be used in other scenarios.
And in particular, you're absolutely right, which is we don't spend enough time in either the problem space or the solution space before we start getting to the how to do it and everything.
And everybody knows like, oh, we can't approach this as a technology project or technology initiative, but what happens really quickly?
It becomes a technology problem and a technology initiative, right?
And so, really thinking through the multi-sided aspects of a problem, taking the appropriate amount of time, not suffering from analysis paralysis, which can be the counter risk to this, of really understanding the customer and the job they are trying to get done, what the real problem is, what are the multi-sided features of it, and then quickly creating the hypotheses for what we think the future state should be.
I'm skipping over the how, how we get there and everything.
So some unconstrained opportunity to really, like what would be the ideal situation?
And then the hypotheses, what are the three to five assumptions or capabilities that would have to be true for us to deliver that future outcome?
Just taking that effort.
My co-author and I, Kevin McCaffrey, have a situation we're dealing with where it's like, I mean, they just plowed through that and then everybody is so anxious to get to building and deploying and things like that.
ROI.
Just take a little more time and kind of the upfront stage and the kind of go slow to go fast mindset is really true upfront.
And you can redo these things too.
And so, but yeah, I agree.
So there's three main elements of the Big Bet Playbook.
So we're not gonna be able to dive into all of them, but just to kind of set the stage for the audience.
So we have the Big Bet Thinking, which is the wicked problem.
I have to say, I love that, because you're from Boston.
Well, but I moved to Boston in 2020, and I'd never heard anyone use the word wicked, and now it's one of my favorite new words.
So the wicked problem, Big Bet environment, so figuring out your opening moves, and then Big Bet management, how you're actually gonna be managing through that problem.
So we don't have time to dig into all of these, but we thought a great approach for our audience would be to try and solve an actual problem or walk through, not solve, sorry.
Walk through and think through a problem that our audience might be tackling.
So John, let's try.
Okay, real time application.
Let's try this.
All right, here we go.
So a big challenge for our audience, operating as an omni-channel organization.
You said it in the beginning, the ways of working inside most large organizations have not changed, but the industry, the environment, the consumer has changed.
And people are still working with the in-store approach, and then there's the e-commerce approach, and they're siloed and they're not talking to each other.
So if this were a problem, someone came to you with and you wanted to use your big bet playbook, where would you start?
Okay, restate the current problem statement?
Operating as an omni-channel organization and breaking down silos.
Okay, great.
And so where I would really want to start with is understanding how that gets manifested to the customer or to some operator external to us, right?
So what are all the ways that this gets manifested?
How often does this happen?
What do we think the impact to it is, right?
And so really what I'm trying to do is kind of size the prize here and really understand the size and the scope of this issue.
And then really understand by reframing the question, it's like, well, why are we in this situation?
And that is a problem statement would easily get transitioned into solely a technology solution relative to get it.
But in my experience, we live in a, we all have to deal with forces and the things that compel us to do stuff.
Understanding the incentive system, both internally and externally, relative to why are we in this situation and what would we have to unfreeze or change in order to actually start making better decisions around this problem would maybe be a real insight into how do we truly solve the problem that resulted in this problem?
Because you may get to a one-time fix of like, hey, we've got a better data flow here and everything.
Great.
But what we know is that, launch is never the end of the journey.
There's always more work to do.
And if we don't solve the underlying, how do we value this channel?
How do we grow it over time?
What is the right roles and responsibilities and incentive systems and decision-making frameworks that led us to get into the situation again?
We're just putting a bandaid on the problem at that point.
So it really is, if this might fit into the, and tell me if it's true, fit into the category of an operating model big bet, in a way.
Would that be accurate that you're trying to change the way you work?
Absolutely.
And it could also, if I think about a portfolio of good ideas versus the really great idea.
And we all know like the most important decision senior leaders make is resource allocation decisions.
And what tends to happen is we get fractionalized across lots of things, and therefore nothing really moves the needle.
And so I would want to really gain clarity of like, you know, how important is this channel to our perspective on future growth?
And make sure that we're at a senior level aligning against what we think the real prize is.
The biggest issue with Big Bets is that we quickly lose the ambition relative to them, right?
We de-risk them by thinking small, by tunneling, by going about it in a very incremental manner.
And so again, what we're trying to solve for is how to both amplify the ambition, but to de-risk it before we make the big commitments relative to it.
And that's, I think, what's truly unique about the Big Bet leadership approach is how to both increase ambition and de-risk it before, the key risks before we actually proceed on it both internally or externally.
And people get that backwards all the time, all the time.
They have a good idea, they commit big to it, they really haven't de-risked it.
That's, you know, the title of the book is kind of a play on words, right?
People think that big bet is about big bets.
It's not about, there's a chapter called thinking big but betting small.
The big is the ambition.
The bets are intended to be placed very small and de-risked until the point it's just a great investment.
We understand what we are doing well enough that we are proceeding with a much better investment thesis than a big bet.
The goal is not to make big bets.
The goal is to have big ambition and do it through experimentation to de-risk them.
So let's say you go through the things to really arrive at a crisp, clear set of outcomes that everyone now has looked around and said, holy crap, and we want that.
Let's go down this path.
In the big bet environment section, you talk about opening moves.
Can you tell us what an opening move might be to build that team that's going to make this process happen?
Yeah, the whole philosophy is summed up in the quote that I start the chapter with, which is, the greatest victory is that which requires no battle.
And so it's like we know there's, we know there's going to be issues and factors that come into play that slow our big bet down.
There's three critical habits that big bet legends have.
They create clarity.
We've just talked about the aspect of creating clarity.
This is about maintaining velocity.
We all start off with great commitment, great vigor, great energy.
We, you know, ooh rah, we're all in.
But these initiatives quickly just slow down and become paced by other gating factors.
So this chapter, Opening Moves, is all about predicting the predictable things that are going to try to slow down and force our big bet to act like other incremental run-the-business projects.
So you can think through, like, what those types of factors are.
They tend to be around policies, policies that impact how we hire, how we staff, how we make decisions, how resources get allocated.
Those policies are geared towards mature run-the-business situations.
They aren't wired towards the special purposes of what a big bet is.
So what do I do as a big bet leader?
Well, I engage early with my stakeholders to help them understand like, these are what we're going to try to do differently.
I can predict some things that are coming on.
And when you typically engage with those stakeholders and you've got executive commitment to this, then you have the leverage to actually like, oh, okay, we're gonna create a separate path, essentially, for your situation.
Fantastic.
Another big one that comes up is just kind of team commitment.
The most predictable risk factor of why big bets fail is because of a completely fractionalized team.
Nobody is truly committed to the effort.
Having a small, dedicated team with a senior leader who is dedicated to the project, the DRI.
At Amazon, we call it the single threaded leader, right?
That has sway in the organization.
They're senior enough to actually get things done within the organization.
A committed team, from my standpoint, is kind of a starting point, yes or no, on whether we're going to be successful on this.
And then the third one is oftentimes the technology environments.
And I've seen too many situations like, yep, we're going for the big bet.
And then quickly it's like, yeah, but we've got a year long system conversion or replatforming that has to take place before we can even get to it.
So predict the fact that we need a separate, I call it a digital lab environment that allows us to quickly iterate on the technology and not allowing the technology barriers to be the thing that slows us down relative to these big bets.
So John, I've seen this in the CPG world manifest as incubators.
So let's say like a large CPG company who as we've been talking about has operated the same way and might take longer to do things, they decide to come up with an incubation team where they're going to develop a new product, a new innovation.
And so they create the small, nimble team, they have that one executive leader, and they are operating in that team and don't have to really, I'm not going to say apply the same rules, but they get to kind of skip some of the processes and they get to work separately.
Is that what you're talking about from a digital lab perspective?
And then I guess my sub question to that is, in the scenario of an incubator, how do you then thread that through the organization to continue beyond just that one moment?
Yeah, well, you're quickly going to run into my limitations, which is I can only remember one question at a time.
Okay, I'll bring it back.
No, no, no, no, no.
So there can be several ways to solve for the issue.
What's most important is that we understand what issue we're trying to deal with.
And so an incubation team can be a way to solve it.
The thing you have to think through then is just what are the constraints that incubation team operates within?
I've seen too many innovation labs, incubation teams, essentially be the land of no accountability.
100%.
And so that's the counterfact.
That's half of Google right now, isn't it?
No comment.
And so you just have to be really thoughtful about how you integrate it in, because most all Big Bats are kind of across the enterprise.
Like they're rarely siloed in nature.
There probably could be a scenario where it is, but that's rare in nature.
You have to think through how do I integrate it across through the executive teams?
We've got a lot of comments further down in the Big Bet management section about how to gain that true alignment.
But an incubation team can be the way to proceed, as long as you have the right leader and the right constraints relative to it, and you're not allowing it become the land of no accountability.
I'm so glad you said that, because I had some experience with an incubator.
And you're right, they just kind of went and did whatever they wanted to do on specifically Amazon and Target.
And I was like, you can't just do that.
Like, that's not how this works.
But they were operating to be able to be nimble and fast and test and learn.
But there were effects of that through the broader organization that they didn't realize because they sat in that side.
So the reason I'm bringing that up is because I think from a larger company organization, a lot of times when people think of Big Bets, they think of let's create a small little team and then go from there.
But to your point and to the whole point of the playbook is it needs to be integrated more broadly to be successful for more than just a year or more than just a project that you're working on.
The reason we call this a leadership book is because it's a combination of both strategy, what do we do, what problem do we solve, how do we figure out how we compete.
But it's also really a communication and culture book, right?
How we work together through these initiatives is an absolute critical pillar of Big Bet leadership.
And so a lot of these challenges get solved by changing how we work, how we communicate.
We've got some very specific recommendations that are kind of built on top of completely reverse engineered kind of Amazon working backward technique of writing things out, debating them.
You know, I wrote a newsletter just the other day that was about, you know, great documents, messy meetings, and that whole notion of really great writing to clarify the situation, but then allowing kind of great debate and messy meetings so that senior leaders actually understand what you're proposing.
So, John, speaking of messy meetings, one of the anecdotes that stood out to me in the book was really one of, I mean, one of your, I'll just say, one of your career-defining big bets that you personally worked on, you brought the Amazon marketplace to market.
And there was a moment in a boardroom somewhere in Amazon where Jeff Bezos turned to you and asked you a question, which changed, really, you know, put you onto a big bet mode of thinking.
Can you just quickly tell our listeners about that?
Because as someone with imposter syndrome, in that moment, I would have just melted.
And anyway, go.
I probably I probably had some of that, too, and everything.
But yeah, so this was, you know, so I was at Amazon from early 2002 through late 2005.
We launched the marketplace business in late 2003.
This is January 2003 at the S team.
I wasn't on the S team, but I was, you know, at the S team meeting talking about the marketplace.
And yeah, Jeff asked me a question about like, well, how many merchants have we launched this year?
And so I started to explain to him essentially why there were no merchants to launch any any and he goes, the answer to that question begins with a number.
And there's actually a really important lesson to learn, which is senior leaders always have like they're trying to daisy chain something together, create a context, answer the question up front, then if they want an explanation, you can explain it.
But that's really not the lesson here.
The lesson was he wanted us all to think like owners.
And even though you have functional responsibility, a job, and you have to be a master of that job, we also want you, you know, longitudinally across the company, oftentimes across against the bureaucracy, like you got to be thinking about enterprise optimization here, right?
And tackling those bottlenecks.
And he was just setting the tone from the top about like, you know, your title might be Director of Merchant Integration, but you need to act like you run the business.
And it was like, I got the point.
And my willingness to be a much more assertive partner with all my other constituents completely changed that day.
And it was needed, and that was completely on me.
And so it's like, you know, I took it as like, what a great lesson.
And that speaks volumes to who you are and how you behave in organizations.
And I'm assuming what you bring to the clients that you work with.
And one of the things I took away is that that's what led you to create kind of the secondary title for roles like this of Chief Repeating Officer.
I think of I think of all the things that Bezos did so well.
The one that doesn't get highlighted much is what a strategic on point, consistent communicator he he was and is and that ability to be on point.
And we go into a lot of depth about this in the book.
But too often senior leaders, they're inconsistent in their communication about what we're trying to do.
They are vague about either the problem we're solving.
They're especially vague about why we're doing it and what the future path is.
And they don't understand the types of commitments or path that we should be laying out when we do that communication.
So we have a whole playbook within the playbook relative to the communication that's required from senior leaders, which is to be focused less on the burning platform, the problem we're solving, be much more specific about the future of where we're going to and why, and then be accurate and very clear about where we are on that journey.
We are testing this concept out or we are fully committed to it and we are scaling it.
Senior leaders get that wrong all the time.
They actually detract, the communication detracts from the situation, doesn't help the situation, and that is something that Big Bet legends do extremely well is be that chief repeating officer.
So John, you talked a little about this in our conversation, but thinking big and betting small and testing things out and deciding whether it's something that you're just going to try or continue forward with.
So if we're thinking about thinking big, betting small, and if we bring it back to that larger problem of operating differently, whether it's through Omnichannel or just operating to be more agile in the environment, what's a way that you can practice that, especially when you have such a meaty problem and you probably have demands from your leadership to do it quickly and to get it done?
Yeah, so I mentioned up front, there's three critical habits that Big Bet legends have.
They create clarity.
We've talked about that.
They maintain velocity.
We've talked about that.
Now we're talking about the third critical habit, and I think it's the most counterintuitive, which is Big Bet legends accelerate risk and value, deferring as much else until you've de-risked the situation, right?
And so Think Big, But Bet Small is all about that experimentation process of how do you actually identify the critical high-value, high-risk assumptions, risks, things that must be true in order to create this outcome?
How do you find ways to accelerate learning and testing and adapting those assumptions before you invest in other things?
And there's a real skill and art to identifying what those high-value, high-risk things are and then finding ways to test them.
But in most incremental projects, and hence where most good operators come from, you come from a very methodical, like left to right, build the foundation, then we build up, then we build up relative to it.
And so in a lot of ways, we are recommending flipping the script.
It may feel like you're wasting a little bit of time and money on this, but it's the most valuable money and time you can take, which is to de-risk these things before you start really building for them.
And so it's all about actual agility and experimentation and doing it on the right things at the right time.
And I can imagine if I'm a leader reading the book or sitting here and thinking about it, it's the like, what if I fail?
That's a big question, especially when it comes to a big risk like that.
Like, what would your answer be, especially going through your experience?
Yeah, that's why language is so critical.
Just the difference between we have an initiative or we have a bet.
If I use the term, we have a bet, and everybody understands what that means.
Oh, okay, I'm clued in.
This is a high value, high risk situation.
So what I expect that person is doing is that they're experimenting and there's a high degree of potential changes that are going to happen here.
That's the type of thing that makes it safe for everybody to actually want to participate on these versus what happens in too many companies.
It's like, oh, they're part of the special projects and everything.
It's like, oh, man, that's a career limiting move, right?
That's a CLM.
And that's why this is a leadership challenge, right?
Because you set the environment that creates the type of culture where, yeah, we say we're going to be innovative and nimble and experimentation, but really people get punished if something doesn't work out.
Short term and long term, you are going to create an incrementalist, play it safe organization.
When I think of our listeners, the last, I don't know, decade of their work for some of them and certainly several years for the rest of them is all about thinking big and betting small.
Like the Digital Shelf was a big bet.
And particularly so in COVID.
But the COVID as a defining event removed a lot of the resistance to massive change quickly and reordering priorities.
Wasn't it amazing how fast we were able to move during the pandemic and everything, right?
Oh, that's because it was a real priority then.
Right.
And in this moment.
When I think back to your mega-forces, all of humanity only moves in crisis, which is super annoying, particularly right now to me, but that's a different podcast.
So it feels like thinking back in a way to COVID and like, holy crap, and look how we transformed the business, the urgency to take on big bets.
How do you see that happening at the organizations you're engaging with?
Is it always a C-level person that knows if we don't change, we're going to die?
Or where does that energy come from to even...
It can come from a couple of places, but at the end of the day, it has to be at the board and the senior level because they truly are accountable and control the resources and the priorities of the organization.
And so it has to end up there, and that's who we wrote this book for.
But, you know, so I absolutely agree with your point, which is great companies that are going to be durable in nature understand that they have to carve off some aspect of resources, time and priority to inventing the future business instead of just incrementalizing through the next year.
And I believe that that's what's going to create really durable brands and enterprise value is those companies that play the long game and allocate the right time and attention towards the big bets that they need to be taking.
And my premise is that all these failure statistics of digital transformation, those are errors of commission where something, an action was taken but it didn't work out.
But it doesn't measure all the errors of omission where a big bet was needed but wasn't taken.
So every time you see a great brand go to average or an average brand go to irrelevant, well, that's a failure.
A big bet wasn't taken.
And what you want is you want time to be able to figure it out and to do it from a position of strength.
I was a partner at a turnaround and restructuring firm for 12 years after Amazon.
I've seen too many companies who wait until it's too late.
You have far fewer options.
You've got a really short runway in front of you.
Your brand is likely kind of damaged at that point too.
It makes turnarounds difficult.
And so we end up the book with the recommendation of you need to be an active skeptic.
Active meaning you need to take action, you need to allocate, you need to make a priority.
But you want to be a skeptic.
You want to prove these things out before you make big commitments.
And so be an active skeptic is the best way I can sum up the advice.
Yeah, and going back to thinking big and betting small, the verbs that you use to describe the decision points that are made along that are so clear that...
And then so you describe...
The verbs are, do we continue this?
Do we kill this?
Do we pivot this?
And then you say, or kind of dot, dot, dot, confusion.
If you don't make a clear one of those three decisions, then you're risking the whole big bet and the process.
Yeah, so not all decisions, not all meetings are the same, right?
There are these high stakes moments where we're evaluating a big bet, and the hygiene around those tends to be really bad, the setup, how we manage them.
And so that chapter is solely dedicated to how we run these high stakes meetings so that you are clear about, do we continue?
Do we pivot?
Do we scale?
Do we pull back?
And you avoid what typically happens, which is there's confusion out of actually what we decided out of this meeting.
All right, listeners, do you want to be a Big Bet legend?
Well, read the remarkable book by John Rossman and Kevin McCaffrey.
It's fascinating, a great read, and I think is a clarion call, but also an actionable clarion call to the next decade or two or more of your company and your career, which I think it's a cool thing to consider.
The book, of course, is available at Amazon, and if you are a DSI member, you're going to get in your email an exclusive discount for the Kindle version and also a book club event.
John, thank you so much for offering that to our community.
That's amazingly generous.
I really look forward to continuing the conversation and to the book club.
And you have all sorts of resources outside the book as well.
Is that true?
I would say more than any book I've ever seen, we are giving away tools and resources to help a reader put this very readable book into action.
And so we kept the book very tight, didn't suffer from too long, didn't read, but we're giving tools, templates, prompts, a scorecard, a bunch of tools to help people transition it into action for their organization.
And all of those are available where?
At bigbetleadership.com.
And we'll be going through them at the book club, so another reason to come.
Check your email.
John, thank you so much again, and congratulations to you both on this book.
Well, thank you for the venue and the great discussion and preparation.
Thank you, John.
Thanks again to John for sharing the highlights of his book and his super kind offer for the discounted Kindle version and book club events.
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