Dec. 6, 2022

Best Books & Authors in 2022 – Jacob Helberg (My Favorite Books, Tools, Habits, and More)

We deconstruct Jacob Helberg's peak performance playbook—from his favorite book to the tiny habit that's had the biggest impact on his life. Jacob is the author of The Wires of War: Technology and the Global Struggle for Power. We cover trend spotting, the wisdom of Winston Churchill, and avoiding procrastination.


We deconstruct Jacob Helberg's peak performance playbook—from his favorite book to the tiny habit that's had the biggest impact on his life. Jacob is the author of The Wires of War: Technology and the Global Struggle for Power. We cover trend spotting, the wisdom of Winston Churchill, and avoiding procrastination.

“If you know in your heart of hearts that something just doesn't feel right with the current path that you're on, I think being open and willing to take some pretty drastic changes, for me, has worked out pretty well.” – Jacob Helberg

EPISODE GUIDE (LINKS, QUOTES, NOTES, AND BOOKS MENTIONED)

https://www.danielscrivner.com/notes/jacob-helberg2-outlier-academy-show-notes 

FULL TEXT TRANSCRIPT

https://www.danielscrivner.com/notes/jacob-helberg-outlier-academy-transcript 

CHAPTERS

In this episode, we deconstruct Jacob Helberg's peak performance playbook—from his favorite book to the tiny habit that's had the biggest impact on his life. In it we cover:

  • 00:00:00 – Introduction
  • 00:01:42 – Investing in technology that advances national security
  • 00:02:39 – Trend spotting and forming deep-seated convictions
  • 00:06:17 – Avoiding procrastination and the importance of exercise
  • 00:09:07 – On Henry Kissinger and Winston Churchill
  • 00:14:35 – Dropping out of law school and trusting your gut

 

ABOUT JACOB HELBERG

Jacob Helberg is the author of the incredible new book, The Wires of War, which details the technical battle that's being waged that will determine the future of the internet and, in many ways, the future of global society. It's a battle that's being waged on both the front and back end of the internet, on the front end in the apps we use every single day from Google to Facebook to TikTok and Twitter, it's stuff like misinformation campaigns, fake followers, and fake news, and on the back end, in the hardware, routers, protocols, and even the undersea cables that travel hundreds of thousands of miles crisscrossing and connecting the entire world.

I loved reading The Wires of War because it's deeply compelling, it's really expansive, and it's an incredibly detailed picture that it paints of where we're at and what we face. It's out now and available on amazon.com.

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ABOUT DANIEL SCRIVNER

Outlier Academy is hosted by Daniel Scrivner. Over the last 15 years, Daniel has led design teams at Square and Apple, turned around a $3M+ ARR SaaS business, and invested in more than 100 companies. He launched Outlier Academy in 2020 to learn from the world’s best founders, investors, authors, and peak performance experts.

Website: https://www.danielscrivner.com

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Transcript

Daniel Scrivner (00:06):
Welcome to a brand new episode of 20 Minute Playbook, a show about how the misfits, rebels, and idealists shaping our world stay at the top of their game, where each week I sit down with an elite performer, from iconic founders and CEOs to world renowned investors and best selling authors to dive into everything from their favorite habits, tools, and books to a favorite failure and their definition of success all in less than 20 minutes.

Daniel Scrivner (00:29):
Jacob Helberg, author of the incredible new book, The Wires of War, is my guest on the show today. That book is all about the technical battle that's being waged that will determine the future of the internet and, in many ways, the future of global society. It's a battle that's being waged on both the front and back end of the internet, on the front end in the apps we use every single day from Google to Facebook to TikTok and Twitter, it's stuff like misinformation campaigns, fake followers, and fake news, and on the back end, in the hardware, routers, protocols, and even the undersea cables that travel hundreds of thousands of miles crisscrossing and connecting the entire world.

Daniel Scrivner (01:05):
I loved reading The Wires of War because it's deeply compelling, it's really expansive, and it's an incredibly detailed picture that it paints of where we're at and what we face. It's out now and available on amazon.com. You could find Jacob Helberg on Twitter @jacobhelberg. That's H-E-L-B-E-R-G. For links to everything we cover in this episode as well as our favorite lessons and takeaways from Jacob, visit outlieracademy.com/68. Now let's jump in with Jacob Helberg, author of The Wires of War. Jacob, thank you so much for coming on 20 Minute Playbook. It's wonderful to have you.

Jacob Helberg (01:41):
Wonderful to be here.

Daniel Scrivner (01:42):
This should be a lot of fun. This show is a little bit faster pace, and I'll ask you the same 10 questions that we ask every guest. So let's go ahead and jump in. One of the first places we like to start is just by asking if there's anything that you've been fascinated about or excited about, obsessed with recently, just something that's top of mind.

Jacob Helberg (02:00):
I've been fascinated by founders in the US building technologies that solve hard engineering challenges that ultimately can play a small part in helping advance the national security of the country.

Daniel Scrivner (02:13):
I have to ask a follow-up question, which is, can you talk about some of those? Because I know some of the investments you've made and I think they're really interesting companies.

Jacob Helberg (02:20):
So I angel invest, and some of the companies that I invested in recently include VARDA and Saildrone. Those are relatively earlier stage in the grand scheme of things. But other companies that are later stage that I have not personally invested in, but I'm very admired of, include, obviously, Palantir, and Anduril.

Daniel Scrivner (02:39):
One of the questions we like to ask everyone is what their superpower is. I think some of the context there is a lot of us go through life, I think, at least the first year, is feeling like we don't have a clue what we're good at. Luckily, at some point in time, you can pick up on that if you're lucky. So I'm curious, what do you think of as your superpowers, and how do you harness those?

Jacob Helberg (02:58):
I think my superpower is, without being braggadocios, but I do think that understanding yourself and what your skills and weaknesses are are ultimately incredibly important throughout the course of your professional life and throughout the course of anyone's professional life. I think that one of the things that has served me fairly well is I tend to be pretty good at trend spotting and picking up on trends relatively early. There's a whole host of things that I have worked on over the years to try to improve myself. But I think that has tend to serve me very well, especially in the space of foreign policy where understanding trends is actually pretty important, because there's a famous French philosopher that once said that governing is anticipating, and being able to anticipate big changes when they're taking place early is actually really useful.

Daniel Scrivner (03:50):
It's fascinating. Do you have any tricks that you use or rules of thumb? Because I feel like the most challenging thing I struggle with there is when something is a true trend versus something that's just a little blip or a spike.

Jacob Helberg (04:04):
Well, for the better and for the worst, I think one of the things that helps me quite a bit to spot trends is that I tend to replay the tape of various conversations I have several times in my head, which, sometimes is a curse, but sometimes it's also a blessing. It basically helps me... My husband jokes that when I use my computer, I always have a million tabs open, and I think that that's just a pretty accurate reflection of the way that my brain works as well. I have a lot of different tabs open at any given point in time. Sometimes that means that I could probably close a few tabs and be just fine, but one of the positive externalities of that is that I think it helps me spot trends.

Daniel Scrivner (04:41):
Well, I'm glad to hear that I'm not alone in having like a thousand tabs and 20 different browser windows that I'm going to close and reopen every time I do my computer. On the flip side, what have you struggled with? What have you butted your head up against, and how have you gotten better at that over time? That can be professionally, personally, wherever you want to take that.

Jacob Helberg (04:59):
I think one of the things that I've struggled with is, as I think is evident throughout the book and any article that I write, I'm someone that tends to form fairly deep-seated convictions about things. I think one of the skills that I've had to work on and that I have come to appreciate as being very important for life is being able to balance having convictions and making the case for your ideas in a work setting, and also being able to hear, appreciate, and balance other competing ideas.

Jacob Helberg (05:36):
Sometimes when you work in a larger organization, but I think it's like this at an organization or outside of an organization, it's like this in life generally, it's being able to really listen to other ideas and even ideas that you disagree with and that you think are incorrect, but understanding the intention behind the idea of the person that you're interacting with. Because sometimes a lot of people just want to be heard. It's not even about the idea itself, but it's about, where are they getting at? Where is their sentiment coming from? Understanding where people are coming from is ultimately a really important skill that I think is incredibly useful for life in general. I think that's something that I've really come to appreciate over the years.

Daniel Scrivner (06:17):
I think that's really well said. You can take this question in terms of what your average day looks like, what the things you've experimented with historically. One question we like to ask everyone is just around habits and routines. The question, the way we typically ask it is, what have you experimented with that have had a positive impact on your life and performance? So it can be things you do today religiously. It can be things you're like, "I'd love to do this again, had been a while."

Jacob Helberg (06:40):
Something that I try to do is, in order to be as methodical as I can about being efficient and allocating my time, I try to avoid putting anything off. Because a lot of the times when I put something off, it sometimes ends up getting deprioritized and never gets done. So when I have to do something, I just try to do it right away on a regular basis for work reasons. Another thing that I try to do just for mental health and sanity, especially since the beginning of the pandemic, is my husband and I are very intent on trying to maintain a physical exercise regimen for health reasons. During the pandemic, we were all locked indoors, so I think being able to find a way of exercising is just a way of expending energy to stay sane. Doing that when having two younger kids and obviously a fairly busy professional schedule can sometimes be challenging. But finding an hour in the day that you can carve out to yourself to be able to do things that you really love and enjoy, I think, is so important.

Daniel Scrivner (07:47):
Especially for parents, when a big part of how you show up interacts a bunch of other humans-

Jacob Helberg (07:53):
[inaudible 00:07:53].

Daniel Scrivner (07:53):
... developing humans. Well, on the fitness side, you talked a little bit about that, just trying to make sure that you set aside that time to take care of yourself and work out each day. Is there anything else that you do, and this can be around the way that you eat, habits, routines you have around sleep, it can be products or tools you use, but anything interesting or anything that you're loving on the health and fitness side?

Jacob Helberg (08:14):
My eating patterns tend to be a little bit erratic. I'll go through phases when I'm eating extremely clean and phases when, if you're really stressed and you're traveling a lot for work where you just want to eat a lot of junk food because it's easy, it tastes great, and when you're stressed out, it really is satisfying. I do think that food is actually quite important for health. Diet and sleep are two things that contribute, to an enormous degree, to people's overall state of health. So I do think that being able to maintain a lifestyle where you sleep enough, which I think a lot of people underestimate how important that is, and also eat decently healthy is important. Ultimately, we're humans. There are things that we like. Sometimes it's chocolate ice cream or whatever it is. Some things aren't always the healthiest. Being able to indulge yourself and treat yourself, I think, is important.

Daniel Scrivner (09:05):
You have to sustain your soul sometimes.

Jacob Helberg (09:07):
[inaudible 00:09:07].

Daniel Scrivner (09:07):
Usually, that's chocolate or some sort of sweet, I feel like. We just spent quite a while talking about the book that you just wrote, The Wires of War, so this would be kind of related. A question we ask everyone is, what books and podcasts have had the biggest impact on the way you work and think? So for you, maybe a different way of saying it would be like, is there anything you're reading recently or that you really are recommending to others? This can be research you did for the book. It can just be totally separate.

Jacob Helberg (09:33):
The way that my brain works is I actually tend to derive an enormous amount of value in reading groups of books, and then comparing in my mind different arguments made by different thinkers and synthesizing what I agree with, what I disagree with. I really enjoyed Michael Pillsbury's book, The Hundred-year Marathon. I find Henry Kissinger's books very interesting, World Order, on China. They're very dense. They are very wonky, and, to be honest, a little bit hard to get through at times, but really interesting, full of really interesting insights.

Jacob Helberg (10:08):
One of my favorite all-time authors that I actually quote multiple times in my book is Winston Churchill. I think he was an extraordinary writer. His command of the English language is hard to match, and he expresses himself with eloquence and humor. This is an example of someone that also had incredibly deep-seated convictions on just about everything, but he's so funny about the way that he expresses himself. A lot of the times, there was such an incredible cardinal of truth in so many of his observations. I find myself enjoying reading almost anything that he writes, whether it's his speeches or A History of the English-Speaking Peoples, his accounts of World War I. He's an incredible writer.

Jacob Helberg (10:57):
The last point that I would make is another type of reading that I tend to enjoy quite a bit are books that are written about the future, so a lot of tech books basically are forward-looking about trends in the future, and then books about the past. I think ultimately one of the intellectual exercises that I enjoy is comparing in what ways... In my book I talk about, technology is obviously new, but ultimately a lot of it is about systems and configurations of power. So there are certain dynamics that have been present throughout history, and there is a real through-line, so being able to see what the through-line is, I find really interesting. So reading books about the past and books that are backward-looking and forward-looking, I find to enjoy quite a bit.

Daniel Scrivner (11:46):
It's amazing. It's probably the best answer I've gotten to that question to date. On the Winston Churchill piece, if you had to read just one speech, one book that he wrote, one piece of content produced by him for the rest of your life, you couldn't read anything else by Winston Churchill, what would you pick?

Jacob Helberg (12:02):
There is a great book that I bought on Amazon that basically is a compilation of his speeches. He wrote a lot of things, but I think his speeches are so fascinating, especially speeches in the tail end of the inner-war period and in the early days of World War II, because these were speeches that he wrote at a time when he was fired up. He's super passionate about what he's talking about. He's very concerned for the future of his country. He is constantly trying to find ways of persuading Parliament and, by the time, the Chamberlain government to do more, warning about this looming danger that he saw in continental Europe, convincing Franklin Roosevelt to be more active. You really feel his energy when you read the speeches and how much he cared about what was going on. I find myself overtaken by a lot of adrenaline every time I read his speeches because they're so galvanizing.

Daniel Scrivner (13:02):
And he has such a clear voice. I feel like in that, there's just something about it that still feels alive, and, to your point, it has that energy. We'll find that book and add it to the show notes, because, one, I want to buy that book.

Jacob Helberg (13:13):
If I could add actually one speech in particular that I especially like, it's called The Lights are Going Out. It's one of his speeches where he essentially talks about how the lights are going out on democracy around the world, where he basically talks about this trend that he was seeing at the time when autocracies were on the advance, democracy was in retreat, and this was obviously a cause of great consternation and should ultimately be a cause of action by Britain as well as the US government. That speech is written so beautifully.

Daniel Scrivner (13:50):
Amazing. We'll link to that as well. I love the title. On software and tools, do you have any software that you use to manage your work, your emails, tasks, and any tools that you use? I see you're wearing these amazing Apple Air headphones. Any other physical tools that you use, you rely on?

Jacob Helberg (14:08):
I just subscribed to Affinity, so I'll be able to tell you in a few weeks if I've ended up becoming addicted to it. I also like the To Do app by Microsoft, although I use it on and off. I'm a little bit old-school. I like taking a lot of notes. So I find that actually a combination of digital tools and manual ones is what I tend to gravitate to the most.

Daniel Scrivner (14:35):
That's super interesting. One question that we always ask every guest, it's my favorite question that we ask, is just if they could share a favorite failure. I think what we're trying to get at there is, while we're all trying to pursue these ambitious, interesting, exciting ideas, a lot of times in life stuff doesn't work out, and oftentimes that's for the better. You can look back and see that, yes, this thing didn't work out and didn't achieve this goal, but it sent me in a better direction and I learned something really valuable. Do you have a favorite failure?

Jacob Helberg (15:03):
Yeah. I actually talk about it in the book. I dropped out of law school. At the time, it was a terrifying decision because my entire life I knew that I was passionate about politics and foreign policy. I had this view that I was on this track and that everyone in this profession, everyone that wants to go into this profession has to go through law school. It's a rite of passage. It's what everyone does. So when I got to law school, I did the program for a whole host of reasons that I talk about in the book. I actually enrolled in a graduate school in France called Sciences Po, and I went back to Paris for about a year. Basically, as the first semester was coming to a close, I was applying for a bunch of summer associate-ships that top-tier law firms based in Paris, like international law firms based in Paris. I got an offer from a white-shoe law firm called Shearman Sterling, which is a very, very good law firm. As I was getting the office walkthrough, I remember looking around thinking, "Wow, if this is the best that my life is going to look like for the next 10 years, I don't know that this is cut out for me."

Jacob Helberg (16:12):
I went to law school because I was passionate about public interest law, but realized after getting into law school, that everyone that has the best jobs in public interest law, namely in the government, all come from, quote/unquote, big law firms. In order to get to a big law firm, you basically have to spend like 10 years at a big law firm in order to make partner, in order to get the best jobs in the government. It's an incredibly long cycle where the cost/benefit equation for me just did not really pan out because the cost was just so high. You basically have to give up every aspect of your life to do something that, to me, felt incredibly dry and boring, which was proofreading contracts as a junior associate for the first few years. That's not really the theory of life. I've always also found fascinating the practice of working at a law firm morbidly boring.

Jacob Helberg (17:05):
So I dropped out, nearly gave my parents a heart attack, moved to California, which is where I ultimately ended up getting involved in the whole startup ecosystem. It was a terrifying experience because all of a sudden this cleanly drawn out plan that I was on for so many years was completely thrown out the window overnight. But ultimately it was for the better.

Jacob Helberg (17:27):
A funny irony, actually, is that a couple years after moving to California, I met my now-husband, Keith, who himself went to law school, joined a law firm. He actually graduated from law school, did a law firm, but he pulled out of the field of law, and jokes how it was one of the best decisions he's ever made. His partner at Founders Fund, Peter Thiel, jokes about how he's also a former practicing attorney, and he jokes how he worked at a law firm where from the outside everyone wanted to get in, and from the inside, everyone wanted to get out. I had a very similar experience. So that gave me some level of comfort that I had made the right decision.

Jacob Helberg (18:04):
Ultimately, one of the things that I really loved about Silicon Valley is that it's an ecosystem of incredibly interesting, bright, self-starting people that all have slightly unconventional backgrounds. I mean, I have a lot of friends that are very successful that are high school dropouts. So I think believing, trusting your gut sometimes and taking that leap so long as you've been really thoughtful about it, I think sometimes can end up serving you quite well. If you know in your heart of hearts that something just doesn't feel right with the current path that you're on, I think being open and willing to take some pretty drastic changes, I think for me, has worked out pretty well.

Daniel Scrivner (18:45):
That's such a great story. Last two questions. The first one is, what is your definition of success? This can be as big, as small as you want it to be. What is that for you?

Jacob Helberg (18:57):
Well, in the context of my book, my definition of success is helping promote a viewpoint that I find really important for the public policy debate. To the extent that this book can contribute to that broader public policy debate, that's ultimately one of the main goals of the book. That would be my definition of success is encouraging a conversation about this because it's on an issue that I find so dear to my heart, but also that I find so important for the country. I think that's how I would define success.

Daniel Scrivner (19:28):
I love it. Last question. What are you most grateful for in this phase of your life?

Jacob Helberg (19:33):
In this phase of my life, I would have to be grateful, at the risk of sounding a little bit cheesy, for my family. My husband and I are incredibly blessed to have two adorable kids. It's been an incredible experience seeing them change almost every day and evolve so quickly. I think that's a blessing that we've been able to experience that has been incredibly fun.

Daniel Scrivner (19:56):
That's fun. Jacob, this has been an incredible conversation. For people listening, you can buy Jacob Helberg's new book, The Wires of War, on Amazon. The audio book's fantastic. I've read the physical book. The physical book's beautiful. I would say get the physical book because mine's filled with tons of underlines, notes in the margins, and all sorts of stuff. Jacob, where can people find you online, follow you on Twitter?

Jacob Helberg (20:16):
They can follow me on Twitter @jacobhelberg. If they haven't already, I encourage everyone to buy the book on Amazon, The Wires of War: Technology and the Global Struggle for Power.

Daniel Scrivner (20:27):
Thank you so much. It's been a lot of fun.

Jacob Helberg (20:29):
Thank you.

Daniel Scrivner (20:32):
Thank you so much for listening. You can find links to everything that we discussed as well as the show notes and transcript for this episode at outlieracademy.com/68. For more from Jacob, listen to our in-depth conversation all about his new book, The Wires of War, in Episode 67. You can also visit outlieracademy.com to explore more incredible interviews with the founders of Rally, Titan, Superhuman, Primal Kitchen, and so many other great companies, as well as bestselling authors and many of the world's smartest investors. From our entire team at Outlier Academy, we hope you enjoyed the show. I hope to see you right here next week on 20 Minute Playbook.