(upbeat music) - All right, moving right along here, Jesse, what do we got next? - All right, next up, we have a question from Joe and he's got a, he talks about little bets, a concept that you introduced in your book, "So Good They Can't Ignore You." - Hi Cal, this is Joe from the Midwest.

I wanted to thank you for answering my previous questions, especially the one about getting, recognizing that we're going through a year of a dumpster fire and to spend the summer really chiseling away at the deep work and get a marine stove while I do it. Didn't get the marine stove, but I did spend the summer working on the big project and it was, it helps keep me sane.

My question is about little bets. You mentioned in "So Good They Can't Ignore You" that you allot time to pursue little bets and you test them out on your blog, as short little blog posts, or you test them out in different ways. I'm wondering, as you get deeper into your career, do you still allot a significant amount of time for these little bets?

For me, I'm very fortunate that I got my first book deal. I'm working really hard on that project and a couple of other really big rocks for my career, but I don't really see, short of Athena bursting out of my skull, how I can allot specific time just to pursue little bets when these other looming deadlines and big projects need my attention now.

So if you could spend some time talking about what role does little bets take as you get deeper into your career, I think it would really help. Thanks. - Well, Joe, congratulations on the book deal. Shame, however, for not buying a marine pellet stove 'cause that is critical. That is critical to any deep work shed space.

For people who don't remember this question, it was Michael Pollan. When Michael Pollan built a writer's shed in the woods behind his house in Kent, Connecticut, he heated it with a marine pellet stove. So it's like a pellet burning stove you put on a boat. So it generates heat, but it's like small, because it's main just for heating a boat.

And so you put a pellet, marine pellet stove in your teeny house, and that's how you heat it while you look out over the snow strewn fields and the snow laden boughs of the birch trees in Kent, Connecticut, and have that warmth as you write in your cabin, wood line cabin.

That's the vision. So yeah, you still need to buy that stove. I actually went out to Kent, Connecticut a few years ago and was doing a speaking gig out there. And it was like at a conference, like one of these conferences they used to do for rich people, basically.

And the rich people come, and then a bunch of speakers and writers come and give talks and stuff. And the speakers and writers come because they want to meet the other speakers and writers. And then the rich people come because they want to hear from the speakers and writers.

It's kind of a weird thing, but kind of a cool thing. And it was in Kent, Connecticut. So Michael Pollan was there because he still kept that house in Kent, Connecticut. And who else was there? Henry Kissinger was there, because he turns out to have a house in Kent, Connecticut.

He's very old now, but he was there as well. But that was interesting. So that's when I learned like, oh, Pollan has the house here. And I can tell you, it's like a beautiful town. It has like this kind of fancy main street, and then it's all hills and trees.

And I get why people flee New York to move to Kent. And so that's my Kent, Connecticut story. All right, but let's get back to Little Bets. So Little Bets was a concept I talked about in So Good They Can't Ignore You. It was coined by, I believe the author's name was Sims.

Maybe Phil Sims? Yeah, I'm not quite sure. Do you have it, Jesse? You could look it up, right? - Well, Phil Sims is definitely a NFL quarterback. So I was just saying- - He's an NFL quarterback who also writes about business strategy in his book, Little Bets. All right, so probably not Phil Sims.

Can you do like a Joe Rogan, Jamie thing here and see if we can find out? No, I feel bad. I feel bad that I'm using the wrong name. Anyways, I think the guy's name was Sims. I mean, this is a decade ago I wrote this book. But it was a self-explanatory concept of in your career, in your business, what you wanna try to do is take steps for which you can get feedback.

And then you can see, and that can direct it. Oh, I get feedback. Like this isn't resonating, this is. So let me go that direction. Let me try a couple more bets. And by making sequential bets and making your future actions based on the feedback from those bets, you can actually have like an evidence-based way of guiding what you do.

And this is better than he would argue coming up with a huge big plan in abstract. And then like, I'm gonna go execute this three-year plan. And I hope it goes well. So Sims was saying, take bets and get feedback. - John Sims? - Is it John Sims? That doesn't sound right.

Can you find the book, Little Bets on? - I'll look for it. - Yeah, like Amazon or something like that. If it is Phil Sims, that'd be awesome. If the quarterback was writing that book. - Phil Sims is on Mad Dog every Friday. I love that spot. - Okay, so Phil Sims is on Mad Dog every Friday talking like Harvard Business Review style career strategy.

Like Mad Dog, let me talk to you about getting feedback from the right market segments on your consulting firm. So Joe, I mean, I think the key thing to take away from Little Bets is- - Peter Sims. - Peter Sims. I was close. - Yeah. - Yeah, Phil Peter.

Peter Sims, little known fact, younger brother of NFL quarterback Phil Sims. I'm just gonna put that out there. Just gonna declare that. So the feedback's what's key. So Joe, the feedback's what's key, right? And so I'm thinking about your situation. Yeah, at some point, as you get feedback and you move along, you get to the place where the steps are pretty big.

But if you're thinking about a book, you're writing a book now, but how did you come to write that book? Hopefully there is a sequence of Little Bets where you are finding these ideas, what resonates, what seems to have an audience. And so you have this clear feedback before you actually go to the stage of writing a book about it.

I think that's a clear example. I mean, take something like my most recent book, "A World Without Email." How many years can you go back and hear me talking about these things? When you can go back and like my first appearance on the Ezra Klein podcast years ago, I'm working through a bunch of the core ideas that became "A World Without Email," right?

Years before. How many articles that I write? There's actually an article I wrote for the Harvard Business Review to promote deep work. So all the way back in 2016, that was about getting rid of email and working through some concepts that made their way into the book. So years of why workout concepts in my Little Bets, or I write about them, or I talk about them on this podcast, or I talk about them on other podcasts, or I write articles about them and I see what the response is.

So like I'm thinking now I might write a book about slow productivity. I've been testing out this idea. I wrote a New Yorker piece about it, got some pretty good feedback that was useful. I did a podcast video about this, a core idea video that was useful. I talked about it on Tim Ferriss' podcast.

And I could see when he split up that interview into segments, he did a clip of the slow productivity discussion, and that's the most viewed clip of all the clips he did from the podcast. That's feedback on this. So those are Little Bets that are helping me put together what I wanna do, and at some point I'm gonna write a book about it.

So Joe, I would say that's the takeaway message is you wanna get real feedback from people, not people like friends, but actual unbiased feedback. Are you buying this? Are you paying for this? Are you giving me money? And allow that to help direct you towards which direction you go.

But I think you're absolutely right to point out that a Little Bet strategy will eventually lead you to really big things that take time. You do a lot of bets on topics, you might then end up spending two years writing a book. Do a bunch of little bets on a product, you might end up at some point taking on investment and going all in on a business.

And that's a multi-year commitment one way or the other. So that's true. Little Bets lead to big commitments, but the key is not to jump right into that big commitment just because you hope or you have a reasonable story about why what you're gonna do would be useful, that you actually have some evidence.

And if you doubt that, talk to NFL quarterback, Phil Sims. He will fill your ear. He will fill your ear with thoughts on Little Bets. - All right, that's a blast for the past. So Good They Can't Ignore You was 2012. So yeah, we're at the 10-year anniversary. Interesting.

That's when I kicked off my writing career as a non-fiction idea book writer. I wrote these three books for students. That's how I got my sea legs, that's how I built up my craft. And So Good They Can't Ignore You was the vision I had all along of, I wanna write idea books, non-fiction books, Table at Barnes & Noble, On NPR, New York Times articles.

That's what I wanted to do. And that's where I kicked off that transition. So it's a really important book for me. It was the first time someone said, "Okay, you're allowed to write a hardcover book "about an idea, it's a crazy thing. "Just an idea you made up. "And you can just put that in a book "and we'll see what happens." So that was definitely a big transition for me.

- That's a cool story. - Yeah. And it was good, that book went to auction. And at the time it seemed like a lot of money. It's how we bought our first, it was the down payment for our first house and how we bought our first car as we came out to Georgetown.

Because that book was really, I wrote it right before I came out here. And it came out right after I got here, it's my memory. My memory is right after I got to Georgetown it came out. But I wrote it as a postdoc. So it was exciting, it was some money and not like life-changing money, but bigger by far, like factor of five bigger than I was getting for the student books or whatever.

And then it didn't do well out of the gates. So there's a story in that. There's a big push, we hired a good PR company and it just kind of disappeared. We're like, "Oh man, I guess." 'Cause I didn't know how publicity, I had no idea how book sales work.

I still don't know how that works. And it's like, "Okay, I guess, "do I get to keep doing this? "I don't know." And so I pitched them deep work finally into like, "Yeah, but we're gonna pay you less money, "but if you wanna write it, go ahead." And it was just a funny thing.

It's just good ideas are good ideas. And it took years, but then it just, it picked up and sold hundreds of thousands of copies. But it was, it seemed like a dud out of the gate. And I'll say the two things that seemed to matter was podcasting came along about two years after I wrote that book.

So I wrote that book, I did a thing for the New York Times and like it got a good, there's a few things I did, it kind of disappeared. And it's some radio, but some stupid radio. And then starting around 2014, podcasting became a thing. And so I became, I was like a very early guest in podcasting circuits, doing a lot of these early podcasts.

And I just did a lot of podcasts, like why not? I thought it was fun. And I think that built the slow burn. If there for like 2014 to 2016, I was on a lot of shows. And that's how I got kind of good at it because I was doing podcasting really early on.

And I sort of learned the medium. And I think that's what really, two years after it came out, started that burn. And then Deep Work did something similar, but its burn was much more intense. Like that book sold a lot of copies. And I think that also just pointed people back towards that original book.

So that's how it all got started for me. I was, got real excited, got this deal, got this book, it disappeared, thought that I'd be done with publishing. And then podcasting came along and Deep Work came along. And that's actually like a, turned out to be a very successful book.

- The other thing too, you talk about and others talk about is, you have, you had another job too. So you weren't relying on that to survive. So I mean, you could like give it some time. - Yeah, exactly. I don't, it would have been harder if I was, well, what happened in the nonfiction space.

- Much more stressful. - And you have to become like a super speaker. That's what was happening back then. If you were trying to make a living off of nonfiction advice books, you had to be doing 30 to 50 speeches a year. And like what a lot of writers would do in that space.

And it's very lucrative by the way, but it's tough. But a lot of writers would just do year on year off. So like 50 speeches, killer. And then a year writing, then 50 speeches a year writing. And you always had to have the book came out. And then your whole life is built around the speaking.

So fortunately I was a professor and so I didn't have to do that. I could just say, I don't know, I guess this book didn't do well. I waited a long time. That book came out in 2012. And then I didn't, Deep Work came out four years later. So I was having kids and trying to get tenure.

And so that was kind of a fun time actually. I mean, there's something innocent to it. I would do, it was entirely homegrown. This is the way I remember it. Is like I would do podcast in my basement and that was it. And then at some point I started writing Deep Work just sort of on my own and that was it.

And then everything else was just organic. And so that's my view. If a book is right, it will eventually sell a lot of copies regardless of what happens early on. I don't know how to make a book sell a lot of copies right up front. I've never been able to do that.

- It's kind of like what the book says. It's so good you can't ignore you. So if like the book is good, it can't be ignored. - Yeah, I don't think anyone knows. Like my editor, I love the editor on that book. He's like, this is a great idea.

Like this, and he was right in the end, we sold a ton of copies of that book. But he was like baffled. He's like, why aren't we early on? Why isn't, why is no one buying this? It's such, I just don't think people understand or they don't understand the degree to which like email lists, these other types of dynamics and cultural, your cultural awareness.

Like this stuff plays a huge role in things like taking off right out of the back. But it's almost like that's orthogonal from whether or not the book is gonna be. So we'll see, we'll see. But it was a cool story. So that started that whole chapter of my life, which was, that was an interesting one.

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