Building the Base episode 10: Nick Sinai, Former White House U.S. Deputy Chief Technology Officer, Advisor and Author

Hondo Geurts 00:01
Welcome back, everybody. Welcome to the latest episode of building the bass. I’m here with Lauren Badulla. And as many of you have listened to the show before, no, we really look for interesting guests, especially those who have done lots of different things in private sector, maybe in government. And this episode, we’ve got one of those guys, Nick Simon has been one of these guys that’s been in the White House. He’s been in the FCC. He’s been in academia. He’s been in, in private industry and venture capital, and really has had an intriguing view on how we need to move forward as a nation, particularly in software and it and so we’re super excited to have you Nick. Welcome. Welcome to Building debase.

Nick Sinai 00:44
Oh, thank you Hondo. Good to see you. Good to see Lauren. I really excited to be here.

Lauren Bedula 00:48
Yeah. Nick, thanks so much for joining us today. We’re so excited to have you. And as Hondo said, you’ve had a really incredible career, having been in the private sector, the Deputy Chief Technology Officer in the White House, to the Federal Communications Commission, and an academia and all of these really seemed to have some linkage to national security. So could you tell our listeners what started you on this journey? And what drove you to move to and from such a diverse set of job experiences?

Nick Sinai 01:13
Sure. So my, you know, I had been a White House intern when I was 20. And then actually convinced me to go into business. Like I saw a bunch of smart minds who are worried about how high candles on Bill Clinton’s 50th birthday cake should be. And I just thought that was a waste of brainpower. And so I was like, you know, I’m gonna go into the business and it did management, consulting, business school venture capital, I was on my honeymoon for five years out of business school, I open the newspaper, and it says, Lehman Brothers goes bust problems. I just started at Lehman Brothers, Venture Partners, new partner track roll, I was all excited to help open the Boston office. And so I turned to my wife and said, you know, honey, you thought you married a venture capitalist, not so much. And so, you know, with complete naivete, I was like, Oh, I’m gonna go get a job in the Obama administration, having very little idea what that meant, and how competitive that was. But I think sometimes you need that naivete, and determination. And so I managed to talk my way into the FCC and get hired part of the National Broadband Plan, one of these blue ribbon Commission’s that was looking at the intersection of advanced communications, broadband and certain national areas. And because I had been doing some clean tech investing, as well as traditional software investing at in my prior firm, I guess I was a good fit there. And I done some telecom earlier in my career. So I was at the FCC got to know the first US CTO, and he’s Chopra. And he hired me into the Office of Science and Technology Policy. And I ended up staying there for years, I was, became the US Deputy Chief Technology Officer, which impressed my mother to no end. But again, not my wife. And after that, I came out and signed up with insight partners, one of the largest software investors in startups and scaleups. I’m based in the Boston area. But But New York is headquartered in New York. And I also signed up with Harvard Kennedy School. And so I’ve been an adjunct there for a number of years. And so you guys are both very kind because I feel like I’ve managed to fail across venture capital and academia and government throughout the course, my career.

Hondo Geurts 03:19
Well, we all succeed by failing, I’m certainly in that realm. So let’s take take me back to the time in the White House. So you’re there. You know, it’s a little bit of a daunting thought in charge of understanding technology, while saddled with a bureaucracy that seems to be more and more challenged dealing with technology. What what did you learn? Or what was that experience? Like, you know, and how did you square the speed at which technology seemed to be accelerating and the challenges it seems to get any policy in place? Due to all sorts of different factors? We seem to be on Divergent Paths?

Nick Sinai 03:54
Yeah. And the the CTS office in the White House, is really a technology and innovation office, which is focused not just on federal IT, and technology for federal and defense missions, but also how do we harness the power of technology and healthcare and education and public safety and so forth? And so one of the things we learned pretty quickly was how do we harness the power of folks working outside of government? And in fact, one of my responsibilities was President Obama’s open data initiatives. So how do we take data and continue to make it a public asset and have private sector entrepreneurs and innovators, build on it, use it create apps and services that help the American public? So to give some examples, weather data, you know, you have a multibillion dollar weather economy, but that is built on weather data that the federal government collects through satellites and buoys, etc. Same thing with GPS right here. We have a military system that has been opened up for civilian use, and you have all kinds of private sector use cases, businesses and verticals built on top of that. And so one of the things We did was, you know, how can we get the federal government to make data more open while protecting privacy, of course, but there’s plenty of data like geospatial data or climate data that you could make more available with API’s around, clean it up, etc. And yes, we did it from a policy perspective of how do you partner with Office of Management Budget and the Federal CIO, in partnership with the USPTO? Like, so how do we write memos to the Federal bureaucracy, but you learned pretty quickly that, you know, a, a memo can be slow, often ignored by by the vast bureaucracy, especially the Department of Defense, which was very good at ignoring those kinds of things. And so like, how do you build that enthusiasm from inside and outside of government to help create the conditions in which policy is not only grudgingly accepted, but celebrate. And so that’s where we did things like data jams, and hackathons and and we call them data Palooza is and we’d have Cabinet Secretaries celebrating private sector innovation, celebrating private sector entrepreneurs who are creating apps to help farmers. But it was also celebrating that that federal worker who had been opening up and making that data more available to researchers or to to innovators. And so if you held up the internal champion, and the and the external entrepreneur, and we weren’t giving money away, and you don’t do that from the White House anyway, but if you’re finding, you’re creating a climate to celebrate this, that makes the policy pieces, which is typically a lot more dry, more receptive, and you actually generate more momentum. Nick, this

Lauren Bedula 06:38
idea of data as a public asset is a really interesting one, because so many companies that we talk to who are trying to do business in the national security or defense markets, have trouble accessing data, and almost acts as a barrier to entry. And you might see this with some of the companies you invest in now or boards you sit in now. And so you’ve looked at this holistically from the White House, do you have any thoughts about national security specifically, or advice to companies who are looking for these datasets like geospatial data, and how they can start stretching the legs of their tech accessing data, rather than seen as a barrier to entry?

Nick Sinai 07:15
Oh, well, Lauren, I would totally agree with you that that we have a ton of data that is locked up in proprietary systems that, you know, primes are building weapons systems and national security, and the ability for not just new entrants, but for the for the Department of Defense to get access to the data. And to be able to, to clean it up to understand it, to use machine learning to think about readiness and predictive maintenance, to think about cyber protection, whatever the the the use cases are, I think that is, is a tremendous challenge. But I also think it’s it’s an opportunity, I mean, that’s, that’s part of the investment thesis behind shift five, you know, while I’m on the board of this really exciting company that that comes out of, you know, some of the founding entrepreneurs come out of our Army Cyber Command, but it also has the commercial DNA, some of the other founding executives and early executives come out of titanium, you know, cybersecurity company. And so that’s just just one example of a company that is, is working to get the get the data and protect the data from planes, and tanks, and so forth. And so this question of, of access to data, I think, is a really big one, because the next generation of entrepreneur, especially venture backed entrepreneur, helping the national security mission has got to get access to that kind of data. So you have to be thinking about, you know, interoperability, and application programming interfaces and all of those kinds of things. And I’m glad to see the Department of Defense move in that direction. You saw a Catholics came out with some some data decrees, I think they’ve sparked lead a lot of that. So that’s, that’s really encouraging to see the department kind of push on on greater interoperability and access to data, but it will remain a opportunity in my mind.

Lauren Bedula 09:14
I’m glad to hear Nick, that’s your take. And it does seem like there’s there’s improvement in the space. And so hopefully, we just keep that momentum up a topic we wanted to hit on it really, from your perspective as a venture capitalist, and you’ve had the time in government as well. But venture capital is starting to become a bit of a buzzword in the department and in the national security space. So, could you tell us a little bit about what the goals of venture capital are when it comes to DOD specifically, and where you see the goals between your community and DOD aligning, and maybe where do you see potential gaps?

Nick Sinai 09:50
Yeah, I see it in a couple of ways. So, one, there is most of venture capital, which sees The Federal Government, the national security enterprise, the Department of Defense, is simply another sales territory, right? And actually, a quite small sales territory compared to the rest of the world. And I, I once got yelled at by actually, a three star. And I just said like, look, you know, you’re the NT E, he was he was talking about nontraditional entities, I was like, no, you don’t understand the army is actually the entity here. And so, for a lot of companies, whether they’re enterprise software or cybersecurity, I realized the department defense is a good-sized market, but it’s actually smaller than financial services, or healthcare, or all of the, you know, fortune 500, big tech, etc. Especially when you put all those things good-sized together, then there’s a set of companies that tend to focus in part or in part or in full on the national security space, which we tend to call defense or dual use. And those types of companies have some national security or DOD DNA. And so, you know, I’m on the board of rebellion, defense, shift, five, Hawkeye 360, in legal lab, and all four of those companies fall into that category where the Department of Defense Intelligence Community, the national security, set of agencies are either a primary or a major customer base for them. And they see the world a little bit differently, because they just have a different sales motion. What is similar across all of these companies, is that they tend to be product companies, and they tend to want to sell the same product again, and again. And I think this is where the Department of Defense and where the national security ecosystem sometimes misses out and doesn’t understand is that these companies fundamentally are trying to sell the same thing over and over again. And so maybe it’s some sort of

Nick Sinai 12:04
scheduling thing, that scheduling thing has got to work for the different services for the different co coms for the for the DOD, and the MO D. And yes, there may be some modest customization, but you’re fundamentally trying to sell a thing. And the way that we know I should not we, but the arm defense, I should say, tends to think about things is not in terms of buying products, right, in terms it thinks in terms of requirements, right, and rights requirements. And so, and even when it goes to buy technology, it is very hardware focused and very people focused, and yet the role of software, whether it’s cyber, whether it’s autonomy, whether know it’s even conventional weapons systems, I mean, look at the lines of code on modern aircraft, right? We’re software is going to be increasingly critical. And we have to be thinking about what’s the role of venture backed software companies and software enabled companies in this ecosystem. And that means that they are fundamentally product-based companies. And this is just something that the Department defense doesn’t really get. And I watch it struggle with, you know, a bunch of valleys of death, a lot of funding of FFR DCS and systems integrators to, you know, and research labs to kind of study the problem and so forth. And I think I can boil it down if you’d let me attempt this into valleys two kind of major problems here. The first one is what I like to call the bureaucratic cruft. Right. So that is the challenge of getting an authority to operate ATO. The accreditation on network is getting the facilities clearance, getting access to classified data, getting valleys a facilities clearance and valleys skiff and, and if you’re going through State Department, getting ITAR, right, so like all of this stuff, makes sense, in theory, but in practice, it all adds up. And it all becomes very manual, very paper based. And so, it just becomes this huge tax. So, for those kinds of conventional venture backed companies that see the DoD as simply, you know, one territory sales territory, it almost becomes insurmountable. They’re like, what’s FedRAMP? What’s, what’s il four, il five? What’s, what’s FCL? What’s, what’s mil cloud, like? It just goes on, and on and on. And they just say, you know what, I’m going to wait a couple years, and I will do I will enter, you know, instead of being $50 million, I’ll wait till I’m $100 million company before I even try and tackle this territory, because it’s so expensive. Then there are the defense and dual US companies that have to endure that tax. And, you know, your big primes are set up to navigate it and understand it, and they, I mean, that’s part of their lifeblood, but these next generation of companies, you know, that is a significant cost, but it’s surmountable. I just think we need to find ways to streamline and modernize it, you know, do it concurrently rather than sequential, automated so forth, so that bureaucratic cruft would be my big problem. Number one, the big problem number two would be the lack of operational buying. And I fundamentally do not think that we buy enough software, from the program executive offices from the programs, we tend to still give requirements to the hardware, hardware-based primes who read software. And we don’t, we don’t buy enough software at scale. So, a lot of the conversation around OTAs, and servers and innovation, all that stuff. That’s, that’s great. And there’s lots of ways that we can do to improve that. But if we fundamentally don’t have the operational buying, I think we’re just we’re just we, the venture community, and the growth community can find ways to fund these companies. And we’ll fund these companies massively if there is a real market. But if there is not a market on the mission side, because we keep giving requirements back to the prime, then I think we’re shooting ourselves in the foot, and we’re not and we’re, these companies will either dry up or they’ll go elsewhere. And that’s, that’s not what we want. So, forgive me, I kind of went on a little rant there.

Hondo Geurts 16:07
Yeah, really thoughtful things. I mean, I think this year, the DOD has the largest r&d budget in its history, I almost think that’s a failure. Because there’s plenty of r&d money around, as you say, within the department within the venture community elsewhere, what there’s not enough is buying and buying red products as they’re used, not buying them and then tailor him to death. The fact we have to develop so much unique stuff, to your point really, really hinders us. I want to go back a little bit to your comment on open data, which I think is really thoughtful. And in my view in a lot of us in Ben’s here been talking about this future industrial base are we contended to future industrial network, and I think two things have to happen. One is this idea of open data, data visibility, transparency, and fluidness. And the second is networking. And if I look at what commercial did, right, it opened up data, and then it massively networked. And that’s what allowed the tremendous efficiencies and new products, do you think that’s a good analogy of where, where we need to take our industrial capacity to, to get what we need out of it to be both secure and prosperous for the next 50 years?

Nick Sinai 17:24
I love this idea of Sinai 17:24 network. And I think it’s a fantastic analogy. The friendly amendment I would make is that there are different types of networks. Right. And so, you can have a very plant, you can have a very planned hierarchical top-down network. And then you can have networks like the internet, where, you know, the standards were loose, the top-down ability to iterate on those standards, the ability, and there’s top-down, there’s lots of problematic pieces to the internet, right? It wasn’t designed with security. And people said, hey, if we knew that it was gonna turn into this, maybe we would build a little bit more security into some of the protocols and those kinds of things. So, I, the internet is not perfect as an analogy. But I think that, that that ability to So, be loosely coupled and loosely connected, and to very quickly, you know, things that are working, continue to get more users and rapidly scale, right and get to billions of users. And we don’t necessarily have billions of soldiers or billions of Airmen or what have you. But we may end up with, you know, billions of autonomous devices in you know, as sensors, right. And so, that kind of hyperscale, but also to kind of reward things that are working and to deprecate those things that aren’t and, and we’d like to fail very slowly, at kind of massive scale. Or rather than then being able to kind of provide money and resources and training and all those things to things that are working. Right. So, it is it is there’s some really great analogies to the to the network one, I just want to think of it more as a bottom out standard based where, where more So, people can plug into that network.

Hondo Geurts 19:21
Yeah, you wouldn’t want to take on a competitor who’s centrally planned by trying to centrally plan them, right. You want to leverage the inherent strengths of capitalism and free markets and partners and allies. I like that I will accept your friendly amendment of a loosely coupled future industrial network. I think that’s a that’s a great addition to the to the thought piece.

Lauren Bedula 19:47
So, Nick, I want to pivot and talk about a book that you recently co-authored, and it’s called Hack Your bureaucracy get things done, no matter what your role on any team and it seems to apply to but we’re talking about today too, which is really solving hard problems or figuring out how to get different communities to work together, effectively. And so, wondering if you could tell our listeners a little bit about what inspired you to write this book and what they can expect to learn from it.

Nick Sinai 20:16
So, my coauthor, Marina NITSA, and I, I spent four years in the White House, she was in the White House working with me, and then went on to be the CTO, the Chief Technology Officer of the VA, which is a fortune 10 enterprise right now, it’s got 400,000 employees at a little less than but at the age of 28, should never finished college, probably the youngest federal civilian SCS that I know. And, and, you know, she couldn’t get anyone to meet with her, she couldn’t get anything done initially. And so, part of this is Marina story about how do you when you’re underestimated, start to make progress. And if you, if you look where the VA is, now, trust in the VA to do the right thing has actually gone up 25 percentage points. And you may, you may remember that the VA used to be, you know, front page news, The Daily Show was making fun of the floors were actually falling because of the weight of the paper. And so that, of course, there were 1000s of people who were involved in the improvement of VA, but part of it is some of some of her stories and some of my, my personal stories, but more importantly, those of our friends and people that we admire, not just in government, but in in, in big tech and startups in Amazon, Google and all kinds of places. And so, you know, we’re really wondering, like what makes people effective in organization. And, you know, we so, start the book with so, two things, one, with Marina, getting yelled at by President Obama and a Cabinet meeting, for not shipping software fast enough at the VA. And she explains to him about the bureaucracy taking so, some time to adopt a new methodology to ship software. And he offers to help he actually offers to record a video for VA employees. And she’s she says very respectfully, you know, I’ll come back to Mr. President as necessary. But it’s that epiphany of the leader of the free world is not going to be able to solve the VA, she had to figure out how this thing really works, how decisions really get made, how change really happens. And so, part of that that opening story is her determination and her epiphany to kind of go back and, and figure out how this thing works. And then how to start chipping away at it. And so, we have a bunch of, of tactics and techniques, about you know, how to start small and build momentum, how to work on the right thing. You know, how to how to build an informal team, too many people will get focused on all the people that formally report you or all the formal resources. But both Marina and I have been in situations in our careers, where we’ve had zero people reporting to us. And yet we were told, I mean, in her case, she was told to go fix the VA. Right. And I was I was, I was told to lead President Obama’s open data initiatives, but with zero resources. And so, this question of how do you get started? How do you get people to scrub in? How do you give credit liberally. There’s just a bunch of a bunch of things like that. The other thing that you might appreciate is we start the book with the sabotage manual of the OSS, the precursor to the CIA. And you may have you may have seen this, it’s kind of infamous, but there’s a bunch of things like referring things to a committee of five or more. And, you know, reopening the minutes of the last meeting and starting to question the, you know, whether those that was a good decision. And so, ultimately, we’re all in bureaucracies or adjacent to that, whether it’s your homeowner’s association, whether its parent, teacher, association, city, local city government, your organization, probably, if it’s of any size has a series of rules and specialization and so forth. And yeah, a lot of that is it can be outdated, but it’s not all, by definition can be bad, right? So, the question is, how do you understand how that works? And how can you start to show progress, and ultimately, you know, use jujitsu or judo, but you want to use the strength of the organization against itself. And so, we tell some stories about that. And, you know, one national security one, we tell the story of the founding of, of Kessel Run, but now the premier Software Factory in the Air Force. So, it’s a good book, hacky bureaucracy. It’s available for preorder, and I hope the listeners go out and buy it. Thank you for letting me plug it.

Hondo Geurts 24:49
So, I love that, Nick. So, September 13, I think is released eight for all of you listening out there. So, you know we were talking earlier before we got going about it. had a campaign that special ops about blowing up bureaucracy and everybody thought the you know, the speed there was because of unique at the word ease and it was more about mindset, right? And how does each person take individual accountability? What’s your show give us the what’s the favorite Nick hack that if you had to pick one out of that, what’s your, what’s your favorite go to move?

Nick Sinai 25:22
Oh, there’s a lot of them in the book, we have over 50 of them, I

Hondo Geurts 25:24
don’t want to everyone I want the favorite; I want the favorite one.

Nick Sinai 25:27
It’s not, it’s among my favorite. And it’s it’s act as if it’s essentially the stone soup. A story I don’t know if you’re familiar with stone soup, but it’s this, this idea of a, of a villager or of a traveler coming to a village and asking for food and being denied. But then setting up the soup. And, and essentially with a stone and hot water, getting tricking the villagers into putting in carrots and salt and meat etc. And, and so some people see that, you know, as a metaphor for for sharing. But I really see that as a metaphor for entrepreneurship and entrepreneurship inside of large organizations. Right? Where, you know, very rarely do people have authority to say no, globally, right? Maybe when when you were the acting Undersecretary of the Navy, you could say we’re not going to do this anywhere in the Navy, but your ability to enforce it on there probably wasn’t that great, right? So if you act as if you can go around, and you can ask for advice, rather than permission. And you start to get people who who give you say, well, this would work if you did it this way or that way. And you start to kind of, you’re socializing an idea, but you’re also getting feedback. And maybe you find someone who’s willing to let you try it with a little bit of resources, a little bit of money, or a little bit of space, or what have you. And in the course of of social that’s akin to that first villager, putting in the the first carrot. And then once you have the carrot, like well, I got the carrot, but now I need the salt, right. And because the the the first one is put the carrot, and you’re more likely to get the salt, it’s the same thing of if there’s some small research lab or PTO inside the Navy that maybe started, maybe I can have a little bit more credibility, and, um, that credibility is going to build. And so it gets to this idea of how do you start small and build momentum. And so stone soup or acting as if inside a large organization, that is one of my favorite tactics. And I use that in the White House to get a bunch of electric utilities, which the White House and the federal government has very little authority over, because they’re mostly regulated the state, we got a bunch of them to commit to make energy data available back to consumers of all types. And we call it the green button initiative. And essentially, we celebrated utilities, were willing to commit to make that available via an open standard so that third party apps with consumer consent could be built on it. Right. And so that was, it was a classic example of, we had to, you know, convince colleagues in the White House that this was a good idea. And we had to, we had to convince the Department of Energy and myths, that was a good idea. But we had to convince a bunch of electric electric utilities that this was, this was a good idea. And they’re, of course, very wary of anything federal as it relates to retail electricity. So sorry for the long story, but act as if we’re stone soup would be kind of one of my favorites there.

Hondo Geurts 28:23
I’m going to I’m gonna also shamelessly plug a book by a mutual friend of ours, Mitch wise, and we the possibility which in reading that has a lot of those tactics applied within within public service entrepreneurship. Yeah.

Nick Sinai 28:40
Mentioned book is fantastic. I highly, highly recommend it. It’s available now.

Lauren Bedula 28:45
Two things really stood out to me, Nick from that, and one was from a few minutes ago, but when you talk about using the strength of an organization against itself, I think that’s such a great idea. And then we talk about on our show a lot cultural barriers, where there’s this interest on all sides of the problem, to solve it. And we’ve spent time admiring the problem, but want to act now. So to just start acting as if, wherever we can, and kind of those grassroots efforts to see how we can make change. And a huge part of that is the people, right? And so as we think about this issue we’re trying to solve in terms of an evolving industrial base and the needs to meet national security, threat priorities. The people are so key. And I know you see that neck to when you’re investing in companies, that tech can be fantastic. But if you don’t have the leadership and the people to lead the companies, it’s probably less appealing. So I’d love to get your thoughts on talent. And you have a really interesting use case too, with your experience with USDS. The United States Digital Service and bringing in tech talent trying to attract them. What do you think the national security community can do to continue to generate interest in serving or working together or maybe from the outside to, but collaborating for national security, any thoughts on really increasing that interest in talent?

Nick Sinai 30:07
This is a fantastic topic, Laura. So I’m a big fan in what I like to call people flow. And so how can we bring people into and out of organizations, and that can be interns and fellows, executives and residents, I was really excited to see the defense ventures Fellows Program, and insight partners has participated in that. And so we’ve we’ve hosted airmen, and sailors and soldiers, who spend six weeks their active duty spent six weeks inside of insight helping us and then they go back to their service. And they bring what they’ve learned about the innovation economy, about venture capital, about startups and scale ups. And so I love that just one small example of, of people flow. So I do think we have to find ways for private sector, tech talent, to serve in government, not just tech talent, but it’s the area that I’m the most passionate and knowledgeable about. And so, you know, we had been calling this idea, essentially civic leave, which is, you know, how do you take a year or two, and, and take leave of whether you’re in big tech, or in big finance, doing tech in big finance, or corporate America or in startups? How do you how do you take that leave, and go serve in the national security space for for a few years, I think tech and service is probably a better rebranding than, than Civic leave. But whatever we call it, this idea of how can civilians bring their cybersecurity, their their, their digital, their product, their design skill sets to the national security community. And so that’s one important way, because not only are they bringing their skill sets, but they’re also learning a ton, and gaining appreciation for the mission and the complexity and for the culture, right, because they’re able to start speaking some of that, that culture. So I think that’s one, one piece where where I really want to see us do more as a defense industrial base, is, is having non traditional companies send people to serve for, you know, a period of time, in, in, directly in, in government, and mostly as a civilian, although there’s a few services that are explored direct commissioning, and those kinds of things, I think we should do it conversely to is find ways to serve in in, especially the startup and scale, community. And, and, and so like I’m passionate about, about those kinds of things, we also have really great talent inside of, of the national security base. And so the question of how do we, how do we keep and upskill is something that I’m really fascinated by, you know, part of the problem is, we don’t have enough trajectory, for product for design for data scientists, etc. Right? Especially if you’re, you know, if you’re, you know, a major or a captain or, you know, you’re kind of coming up, and it’s okay, well, we’ll let you be a data scientist for now. But then you have to go be an executive officer out in the field for for a couple years, etc. And people who, who are technical and hands on keyboard, you know, they want to keep refining their technical skills, they may not want to be the generalist that the military often often promotes, you know, people don’t usually leave just because of money. It is because of the opportunity to have an impact their boss, and all those kinds of things. So I think these these conversations about talent are too often focused on on on just pay, which I think is important. And we want to try and improve public sector pay 10s pay all the those kinds of things. But I think it’s more about how do we find ways for them to really have the opportunities to have impact to work in more modern environments. I mean, you know, it’s so frustrating to try and do something and it takes you minutes for your computer to load. And it’s, and you’re not able to use kind of modern development tools, you know, you get frustrated, right. And so I think that’s another piece that I’m passionate about is how do we kind of improve the environment, both physical and the virtual environment that the National Security Security space works in?

Nick Sinai 34:53
And so to that end, I am very excited about the there’s a new US digital core, which is about early career technologists serving in public sector, we just got this launched. This is actually a federal program that the Biden administration is championing and is one of their initiatives. Right now. It’s 40. Federal civilian, early career technologists for two year fellowships. But I’m hopeful it expands to the Department of Defense. You know, traditionally, the intelligence community has done a really nice job of, of going early. And, and spending time identifying talent. Part of it is the classification challenges have been so challenging that they have made sure that they went early. But I think it’s something that we could do in in defense better, especially on the civilian side, where traditionally, we have not paid enough attention to the Federal civilian workforce in defense.

Hondo Geurts 35:52
Yeah, that’s, that’s really, it’s a key point. And I think it’s only accentuated with current conflict in the Ukraine. And what I would contend is the first time we’re pure commercial, and some of the companies you’re familiar with Hawkeye, 360, whatever, are having profound impacts on the battlefield, in a commercial sense, not just in a traditional dual use sense. Do you see that as the as a trend continuing? And? And how do you think about this? I think for a while, we tried to separate you know, national prosperity and national security are two kind of completely different things. And almost by trade wanted to keep away from each other. And you know, it, there’s far less DoD only tech or commercial only tech, there’s tech, and it’s just how you’re using it. What’s your, you’re kind of in a unique position to see that. What’s your thought on that, Nick?

Nick Sinai 36:48
Yeah. So I mean, starting with the the Ukraine part of the question, it’s my, my impression from my limited vantage point of, you know, being on the board of of a few companies, that commercial technologies and commercial data have a really important role to play. And you can see that in, in in public ways. I mean, a company like Hawkeye 360, has been public about the GPS jamming that they’ve been able to show and they put this on their on their website about look at the GPS jamming, you see that when you watch CNN, and you see the the maxar pictures, right. And so I think that the Department of Defense has done a really nice job of declassifying and making available commercial data, to the American public into the world, to show the atrocities to show to show the troop movements to show show, whatever, I, I think we still like to build exquisite systems for exquisite people in government, a little too much. And, but I also see that not just as a problem, but as an opportunity. And that’s why we’re funding some of the companies that we’re funding. And I’m excited about some of the other venture capital firms that are also funding, sometimes with us, and sometimes in other companies. But we have a collection of companies that are providing commercial capabilities, again, that these are things that they’re also serving either other militaries, or the commercial space industry or the maritime and fishing industry, right? You know, the, the that same, that same data that Hawkeye 360s Collecting can also help with, with poaching and smuggling, right. And so there’s a lot of use cases for for, you know, a lot of this information. And so, I think that we need to make sure that we continue as a Defense Department as the national security apparatus, to to find ways to try by and scale commercial capabilities. And we’re still in the early days of that. And, you know, if we don’t, we’re going to be in a situation where our ability to deter in great power conflict, in strategic competition is going to be diminished. And that’s not going to be good for our national security for our values. Right? It’s going to be better for the authoritarian values, you know, our, our economy will continue to hum along just fine. But But ultimately, it’s, it’s, I think it’s going to be to the detriment of our way of life long term. And so I think it’s a mistake to say, hey, we can all ignore the national security market because it’s just custom and bureaucratic and those those kinds of things and So it does have some some friction, it does have a culture. And, you know, what part of the the point of the book was, was to write that you really have to understand stuff before you try and disrupt it. Right. And so I’ve, I’ve observed, I’m sure both of you have to people coming in to the Defense Department at fashion themselves as disruptors. Right. And, and, and then, you know, been unable to have the impact that they wanted to have. And part of that is because they, they may not have recognized that, you know, the more that you partner and give credit away, and build things, so that, you know, if you get hit by a bus, it actually will continue. Right. So it’s the the no heroes, kind of philosophy.

Nick Sinai 40:53
Finding all the people who have failed at something, we talked about this in the book about it was on the 19th try, that Marina was able to get something done, only because when she proposed an idea, someone was nice enough to show her, they actually had a binder of the 18 previous proposals, and this was like, you know, how do you how do you basically update data once for a veteran, a veteran changes his or her address, and everyone been having this idea, everyone thought this was a new idea, every new, you know, political administration that came in was like, Oh, we’re going to just fix the VA, and you’re gonna be able to update your data once as a veteran, and it’s gonna populate across all the all the systems. And Marina were quite, quite smart, and my co author from hacker bureaucracy, she quite smartly, went and talked to people who had tried in the past and figured out why. And so knowing the Department of Defense and understanding kind of how it makes decisions, what the culture is, we’re going to need a number of of descriptors that are homegrown from the system, as well as, as outside people flowing in, who have the full respect, and you know, is that balance between respecting the mission and the people and the processes and the rules, while you seem to disrupt it, right. And it’s that balance of if you don’t understand them, then your ability to disrupt them, and to actually improve them and make, you know, impacted at massive scale is going to be that much harder.

Lauren Bedula 42:24
I think that is such an important point, Nick. And it also makes me think of this trend that you’re part of which is more and more investors looking at the national security community to not only invest, but become an interlocutor between the communities and help translate things like use cases, or processes bureaucratic crust, as you say, so that it is easier to navigate and disrupt. And so you’re acting as in many ways, a mentor to these companies, you’re sitting on the boards and helping them not just by writing a check, but through market development and use cases in the like, because you sat on the US government side and have that experience. I’m wondering, Nick, if you’ve have had any mentors around along the way that have really influenced your path and trajectory or ability to disrupt?

Nick Sinai 43:14
Yeah, a lot have been very, very fortunate to have have great mentors, and great bosses. You know, all three of the Chief Technology Officers of of the US and Obama ministration were friends and mentors and great bosses. And, and I learned a lot from them, watching, you know, how to treat other people how to celebrate ideas, wherever they come from, right how to how to not be afraid to ask stupid questions. And you know, I think, I think when leaders admit they don’t know something or ask people to explain because they’re confused. I think that just sets the right tone, psychological safety. So, you know, I’d have to put it a niche Chopra, Todd Park and Megan Smith, those those first, I guess the CTOs in the Obama ministration up there as mentors. I’ve had a lot of mentors in my career, I’ve been fortunate to maybe just because I keep asking dumb questions, and people sometimes give me answers. And so I really liked that part of teaching. And that’s, that’s what I like doing at the Kennedy School. Truth be told, I’m actually a pretty mediocre instructor. But I enjoy listening to the students and helping them and what’s great is a number of them are coming from public service or going into public service. I’ve been fortunate enough to also teach students from the college and the business school, and the engineering school and the design school. And so I really liked that kind of interdisciplinary piece to it wherever, wherever I can kind of draw from those different disciplines. And, you know, I, I encourage them to be more ambitious. I think too often times, you know, we, we get trapped by our constraints. And this is true if you’re in an organization for a long time, like you get trapped by those constraints. And there’s this question of like, what’s a, what’s a fixed constraint versus something that actually could change. And I’ve been guilty of this too, where you’re working in organization long enough, and you something that someone else may come in and say, hey, that’s variable, we could change it. If we did X, Y, and Z, you start to assume it as a fixed constraint. And so, you know, I like to remind the students that I have the privilege of teaching and mentoring. And, you know, truth be told, I learned more from them than they learned from me. But, you know, for them to aim high and, and, and, you know, that nobody was born knowing knowing anything. And that, you know, we’re going to, as long as you’re, you’re working hard, you know, you have your integrity, you know, you’re and you’re kind to people, you know, things will go, you’ll go far right? And so a little little bit of hustle and elbow grease and kindness will get you there.

Hondo Geurts 46:14
Nick, it’s been awesome having you here on the show. We we kind of went all over the place. But I think for any of our listeners out there who heard now here’s the guy who has been all over the place but still wants to give back. And so I can’t wait to read your book when it comes out. September 13. I think it is a hacking your bureaucracy, how anybody can have a role in that and not not be a victim but be an advocate for positive change. Thanks so much for joining us, Nick.

Nick Sinai 46:41
Thank you, Lauren. It was a pleasure.

Lauren Bedula 46:42
Thanks, Nick.