“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

Jacob Helberg (@jacobhelberg) is the author of the recently published book, The Wires of War: Technology and the Global Struggle for Power. He is also Co-Chair of the China Strategy Initiative Working Group at The Brookings Institution, Senior Advisor of the Program on Geopolitics & Technology at the Cyber Policy Center and an adjunct fellow at the Center for Strategic and International Studies. 

To hear Jacob’s author interview on his book The Wires of War, click here.‍

Chapters

  • 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

Jacob Helberg's Favorite Books

Transcript

Daniel Scrivner:

Jacob, thank you so much for coming on 20 Minute Playbook. It's wonderful to have you.

Jacob Helberg:

Wonderful to be here.

Daniel Scrivner:

So 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:

I've been fascinated by founders in the U.S. 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:

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 in really interesting companies.

Jacob Helberg:

Yeah. So I angel invest. And some of the companies that I invested in recently include Varda and Saildrone, and 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:

One of the questions we like to ask everyone is what their superpower is. And 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. And 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:

I think my superpowers without being braggadocious, but I do think that understanding yourself and what your skills and weaknesses are ultimately incredibly important throughout the course of your professional life and throughout the course of anyone's professional life. And 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:

It's fascinating. Do you have any tricks that you use or rule of thumbs? 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:

Well, for the better and for the worse, I think one of the things that helps me quite a bit spot trends is that I tend to replay the tape of various conversations I have several times in my head. Which sometimes is ac 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. And sometimes, that means that I could probably close a few tabs and be just fine. But one of the positive external of that is that I think it helps me spot trends.

Daniel Scrivner:

Well, I'm glad to hear that I'm not alone in having 1,000 tabs in 20 different browser windows that can 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? And that can be professionally, personally, wherever you want to take that.

Jacob Helberg:

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. And 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. And 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.

Jacob Helberg:

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. And I think that's something that I've really come to appreciate over the years.

Daniel Scrivner:

I think that's really well said. Thinking about, and you can take this question in terms of what your average day looks like, what things you've experimented with historically. But one question we like to ask everyone is just around habits and routines. And I think 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, can be things you're like, "I'd love to do this again. Hasn't happened in a while."

Jacob Helberg:

Something that I try to do is I try 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.

Jacob Helberg:

Another thing that I try to do just for mental health insanity, 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 doors. So I think being able to find a way of exercising is just a way of expending energy to stay sane. And that's doing that when and 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:

Especially for parents. When a big part of how you show up interacts a bunch of other humans, developing humans. 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:

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, and 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.

Jacob Helberg:

So I do think that food is actually quite important for health. So 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. But I mean ultimately, we're humans. And there are things that we like, and sometimes a 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:

Yeah. You have to sustain your soul sometimes. Especially if it's chocolate or some sort of sweet, I feel like. So 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, but 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 is there anything you're reading recently or that you really are recommending to others? So this can be book you researched for the book. It can just be totally separate.

Jacob Helberg:

So 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:

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. I mean his command of the English language is hard to match. And he expresses himself with eloquence and humor. And I think so often, 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. And a lot of the times, there was such an incredible cardinal of truth and 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 people, his accounts of World War I. He's an incredible writer.

Jacob Helberg:

And the last point that I would make is another type of reading that I tend to enjoy quite 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. And 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 it quite a bit.

Daniel Scrivner:

It's amazing. It's probably the best answer I've gotten to that question to date. So 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:

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 because especially speeches in the tail end of the Interwar 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, to warning about this looming danger that he saw in continental Europe, convincing Franklin Roosevelt to be more active. So you really feel his energy when you read the speeches and how much he cared about was going on. And I find myself overtaken by a lot of adrenaline every time I read his speeches, because they're so galvanizing.

Daniel Scrivner:

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:

If I could add actually one speech in particular that I especially like, it's called the lights are going out. And it's one of his speeches where he essentially talks about how the lights are going out on democracy around the world, and 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 U.S. government. And that speech is written so beautifully.

Daniel Scrivner:

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:

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, but 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:

Super interesting. So 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. And 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. And 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. I learned something really valuable. Do you have a favorite failure?

Jacob Helberg:

Yeah. And I actually talk about it in the book. I dropped out of law school. And at the time, it was a terrifying decision because my entire life, I knew that I was passionate about politics and foreign policy. And 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.

Jacob Helberg:

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. And basically, as the first semester was coming to a close, I was applying for a bunch of summer associateships at 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.

Jacob Helberg:

And 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." I mean, 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 and namely in the government all come from 'big' law firms. And in order to get to a big law firm, you basically have to spend 10 years at a big law firm in order to make partner, in order to get the best jobs in the government. And 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. I mean, 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.

Jacob Helberg:

The theory of law I've also found fascinating, the practice of working at a law firm, morbidly boring. 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. And 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. And 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. And 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. And I had a very similar experience. So that gave me some level of comfort that I had made the right decision.

Jacob Helberg:

And 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.

Jacob Helberg:

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. I mean, 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 that pretty well.

Daniel Scrivner:

That's such a great story. Okay. Last two questions. The first one is what is your definition of success? And this can be as big, as small as you want it to be. What is it for you?

Jacob Helberg:

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. So 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. And 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:

I love it. Last question. What are you most grateful for in this phase of your life?

Jacob Helberg:

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. So it's been an incredible experience seeing them change almost every day and evolve so quickly. And I think it's a blessing that we've been able to experience that has been incredibly fun.

Daniel Scrivner:

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 is beautiful. And 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:

So they can follow me on Twitter @jacobhelberg. And if they haven't already, I'd encourage everyone to buy the book on Amazon The Wires of War: Technology and the Global Struggle for Power.

Daniel Scrivner:

Thank you so much. It's been a lot of fun.

Jacob Helberg:

Thank you.