Podcast

White House Experience Informs Venture Capital

Posted: 1st February 2021

By: CAITLIN MATTINGLY

White House Experience Informs Venture Capital

Our guest is Nick Sinai, Senior Advisor at Insight Partners, a global venture capital and private equity firm investing in high-growth software companies.

Before joining Insight in 2014, Nick served in the White House, where he was U.S. Deputy Chief Technology Officer. At the White House, Nick led President Obama’s Open Data Initiatives and helped start and grow the Presidential Innovation Fellows program, which brings entrepreneurs, innovators, and technologists into government.

Nick is a senior fellow and former adjunct faculty at the Harvard Kennedy School, where he taught a class on technology and innovation in government fields. Nick is also an advisor to Coding It Forward, a nonprofit that places computer science, data science, and design students in federal agencies.

This podcast was produced in partnership with the CyberWire.

For those of you who’d prefer to read, here’s the transcript:

This is Recorded Future, inside threat intelligence for cybersecurity.

Dave Bittner:

Hello everyone, and welcome to episode 194 of the Recorded Future podcast. I'm Dave Bittner from the CyberWire.

Our guest is Nick Sinai, Senior Advisor at Insight Partners, a global venture capital and private equity firm investing in high-growth software companies.

Nick Sinai:

I always wanted to be a venture capitalist, or at least I had started as a management consultant coming out of college and had gone to business school with the eye of getting into venture capital. And so I did just that and talked my way into a venture capital firm here in the Boston area called Polaris Venture Partners. Worked on a number of investments for Polaris, and then eventually got hired at a second firm. The only challenge was I was on my honeymoon when Lehman Brothers went bust.

I had just joined Lehman Brothers Venture Partners to help build a new Boston office of a Silicon Valley headquartered venture firm. And so I turned to my wife and said, "You thought you married a venture capitalist." This was in Italy the very first day of our honeymoon. And I said, "Look, let's enjoy our honeymoon, and we'll figure it out when we get back." And sure enough, there wasn't opportunity for me going forward. The venture firm was able to be spun out and is now Tenaya Capital. But I was in my early thirties and decided to do a bit of a career pivot. I'd been in venture capital almost five years, post MBA, and decided to do this pivot to go into the public sector.

Dave Bittner:

Yeah, that's interesting. And can you share some insights? I mean, is there a typical career path for those looking to get into venture capital? I mean, is the business degree the most common way to go in that direction?

Nick Sinai:

No, that's actually pretty atypical these days. So there are some folks from business school, principly HBS and Stanford that make their way into venture capital and more so on the private equity side. But I'd say a more conventional path is being in the tech economy, being at a startup or being at big tech doing something on the engineering or product management side and then coming into one of these firms. And so I essentially had to talk my way into it where, at the time, Polaris had said, "Look, we're not really hiring MBAs. And there isn't a long term career trajectory for you. And by the way, you've been doing mostly telecom strategy consulting, and we're more interested in internet and enterprise software." And I said, "No worries. I can learn enterprise software and internet, and I'm excited to be in the industry. We don't have to worry about a long term career track kind of thing. And just pay me like I don't have an MBA."

And having surmounted all of those objections, I hit it off with them. I got hired there. And then the Lehman Brothers Venture Partners was a career track opportunity. And so I was very excited about that. I was nine months into that, when Lehman Brothers went bust. In retrospect, I'm really excited that Lehman went bust because it opened the door for me to do a public sector career, or at least a stint in government. And I managed to start talking to the transition team of the Obama administration and eventually got hired as part of the National Broadband Plan, which was one of these blue ribbon task forces. And in this case, we were looking at how broadband in advanced communication can help the national good.

And so I was assigned to lead a small team, doing energy and environment and intersection with communications. And so I recruited a small team, and we worked on a series of recommendations that we presented to the administration and to Congress. And I was asked to testify to Congress. And so that was tremendous fun and gave me a chance to get into the policymaking side of things. And from there, I got hired at the White House into the chief technology officer's office working for Aneesh Chopra. And I spent four years in the White House. Ultimately, I became one of the U.S. deputy chief technology officers. And it was such a rewarding experience. I had a chance to lead President Obama's Open Data Initiatives. So how do we take data and make it a public good? I had a chance to help start and grow the Presidential Innovation Fellows program, and helped with the start in the U.S. Digital Services.

And this was an exciting time. And increasingly an administration that was recognizing how central technology was to service delivery. Healthcare.gov had its infamous challenges. And my boss at the time, U.S. CTO Todd Park, helped lead the rescue. And that really solidified the need to have a whole set of technologists in governance. That led to the creation of the U.S. Digital Service, which was just getting stood up as I was leaving at the end of 2014. And so I joined Insight Partners headquartered in New York, but I live up here in the Massachusetts area, at the very end of 2014. And I also joined Harvard Kennedy School where I'm a senior fellow at the Belfer Center. But I've served as adjunct faculty and designed and taught a class, tech and innovation in government for the last five years.

Dave Bittner:

Well, let's dig into some of your time in public service, specifically at the White House. First of all, what prompted your decision to shift to the public sector?

Nick Sinai:

Well, it's something I'd always been really excited about. I guess I grew up in a family where my mother was very much a news junkie. My grandfather had served in the Army. And so I'd always been interested in politics and in government and had the fortune of being a White House intern when I was in college. And so I'd always been interested, and I just didn't know in what capacity I would have the opportunity to serve. It took something like the Lehman bankruptcy to really force my hand and think about doing a stint. And at the time, I thought it would just be a year or two. And the more I got into it, the more I really appreciated the scale, the complexity of the chance to have impact at massive scale. And the people that I met who were so bright and hardworking and mission oriented. And so what was going to be one-to-two years turned into five and a half years.

Dave Bittner:

Describe for us, what was the lay of the land when you got started there? Things change so quickly in tech. Thinking back to the early 2010s, it was a different world when it comes to things like broadband and communication.

Nick Sinai:

Yeah. It was definitely a different world. So the most jarring thing was just how behind government IT was. So when you think about the laptop or personal computer, the software applications that you could use, those things are always a little bit jarring and frustrating. From a broadband perspective, the FCC is involved in classifying what is the speed of broadband and thinking about how to support broadband subsidies through the Universal Service Fund. And so it was a different time in many respects, but we still have a digital divide today. So for all of the good work that I think has been done, and certainly technology has changed, I think the biggest difference in a decade is just how mobile first we are. And the internet really is at our fingertips because everyone has smartphones.

Yes, we had smartphones back in 2010, but when you think about just the rise of social media and the rise of mobile first in that decade, I think, is ... The other thing I'd say, is that there was still this presumption of good for tech. And this is a bit of a broad brush because we certainly recognized that there are downsides to technology. But I think generally speaking, the Obama administration saw the potential for all that technology can do. And that you had a lot of idealism coming into government and that included idealism about technology and idealism about the technology industry.

And if there's anything that the last 10 years have shown, is that there's a lot of downsides to technology, to technology companies. And we see that in the cybersecurity space. And just in terms of all the challenges we're having from adversaries and breaches, and so forth. We see that in the threats to our democracy. Foreign states and their affiliates using our own social networks to sow misinformation and disinformation. And so it's not that we didn't think about some of the downsides of technology, but it is fair to say that there was more enthusiasm and presumption of good certainly than there is now.

Dave Bittner:

One of the things that you played a key role in was starting the Presidential Innovation Fellows program. Can you describe to us what was that about, and how did it come to be? What caused it to come to pass?

Nick Sinai:

Yeah. So this was the brainchild of my boss at the time who was U.S. Chief Technology Officer Todd Park. Todd is a serial entrepreneur, and has created multiple multi-billion dollar market cap companies. He came in and really was inspired by Code for America and their fellowship model. And for those of you not familiar with Code for America, they started by putting fellows in local government, usually mid-career technologists, or earlier-career technologists into government. Inspired by that, adapting that model, Todd went about the White House and convinced senior leaders that this would be a good injection of talent, and it worked. John Farmer was the lead of it in the Office of Science and Technology Policy, in the CTO's office, with Arianne Gallagher and myself and others. So we convinced some agencies to put forward some problem statements and have some internal teams.

And then they went out, I think it was a TechCrunch Disrupt that Todd was the U.S. CTO and Steve VanRoekel, who was the U.S. CIO, went out and did a call for applications and got several hundred folks to apply. And I think it was north of a dozen, but not quite 20, I forget. It was 17 maybe or 18, that first class, people who were taking a real chance on us. And we embedded them in the agencies, and they were working on things like making data more open and machine readable, or making it easier to get your own medical data, for example, at the VA, the Blue Button Initiative. They took a chance on us, and it ended up being a real injection of great entrepreneurial and technical talent. And some of the folks stuck around and got so inspired by the mission problems that they were working on and the teams that they were working on, that they stayed in government.

And that actually led to the creation of tech units like 18F at the General Services Administration and the Digital Services, the USDS. And so that was fantastic that some would stick around. And if you look now, like the chief technology officer of the VA. This is a Fortune 10 size enterprise with over 400,000 employees. Charles Worthington is a former PIF, Presidential Innovation Fellows. So it became an on-ramp for technical and entrepreneurial talent. And the exciting thing about it is it became a bi-partisan idea.

It's something that President Obama wrote in the executive order, but then bi-partisan legislation was entered in Congress. And in fact, the very last bill that President Obama signed near minutes before he handed over power. So he was actually in the capital, and they were running around trying to find him so they could get his signature to make it a law. The PIF program continues today, and over a hundred fellows have served in government. And many have gone back to work in startups and big tech and civic tech and nonprofits, but many have stayed in government. And it's something that I'm really excited to have played a small part in.

Dave Bittner:

Having gone back to the private sector now, how does the time that you spent in the public sector inform the work that you do today?

Nick Sinai:

What I do at Insight is helping private sector software companies, who are winning in the private sector, I help them enter and grow in the public sector market. So it's very relevant because I have a better sense of what the public sector is thinking and how to navigate that mission orientation. So for me, it was a natural thing to try and bring two parts of my earlier venture capital experiences. And then my experiences in government and trying to find a way to marry them. At the Kennedy School, I have been passionate about the next generation finding ways to serve directly in government. And so it's been a lot of fun to create this class and mentor a number of students and student clubs.

Dave Bittner:

I know you're involved with an organization called Coding it Forward, that's a non-profit organization. What sort of work do they do?

Nick Sinai:

It started with a couple of students, one of which was in my class and a few others that I had become friendly with. And these were Harvard college students. Most of my class is graduate students, but I also have a couple undergraduates that take the class as well. And one of them had spent a previous summer interning at Uber Engineering. And so they came to me, and they were looking for summer internships in the federal government. And they went on to usajobs.gov, which is the primary website for federal hiring. And all they could find was a SharePoint implementation and no disrespect to SharePoint, but they're not exactly cutting edge or that interesting for young computer science students at Harvard. And so being entrepreneurial students, they formed a non-profit called Coding it Forward focused on the next generation of technical talent.

And the first thing that they have focused on is an internship, which they call the Civic Digital Fellowship. And so they've recruited from hundreds of colleges and universities across the country and placed those in a half dozen federal agencies with mentorship and support working on technical products. And so these could be computer scientists or computer science students, data scientists and data engineers, as well as designers, folks focused on human-centered design. And so I think this is the fourth summer that they've run it. And they had over 60 fellows placed in the summer across a half dozen federal agencies. Some of these fellows have gone on to full-time employment. They have a very popular demo day at the end of the summer. And so it's a great proof point that the next generation does want to serve in government and feels that they want to bring their technical skills to do a stint.

And many of these students want to make it a part of their career, at least a stint, and some of them wanted to make it their entire career. So it's really inspiring to me to see what, I guess we're calling it generation Z, how they want to serve. And we have this whole idea of public interest lawyers and public interest law, where the lawyers have a pro bono expectation. And the top lawyers from top law schools go and clerk at Supreme Court or Federal Court of Appeals.

And so there's a public service piece to elite law school. But every lawyer is trained with this idea of pro bono work. And so we should be thinking about this in the context of technologists. And when I say technologists, I mean broadly speaking. Those in product management and design and all of the folks in the broader technology community. And so I'm super excited about Coding it Forward as a non-profit that I mentor and advise, what they've been able to show about the next generation, their desire to serve and help with some of the tech skills gap that we have in government.

Dave Bittner:

Our thanks to Nick Sinai from Insight Partners for joining us.

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We hope you've enjoyed the show and that you'll subscribe and help spread the word among your colleagues and online. The Recorded Future podcast production team includes Coordinating Producer Caitlin Mattingly. The show is produced by the CyberWire, with Executive Editor Peter Kilpe, and I'm Dave Bittner.

Thanks for listening.