Scott Kupor on Building a16z and Rebuilding the Federal Workforce
- 01Disaggregating the Star Investor: The CAA Model Applied to Venture
- 02Marketing as a Wedge When You Lack a Track Record
- 03Counter-Cyclical Timing and Momentum Compounding
- 04Founders Subsidizing the Platform
- 05Centralize, Then Federate as the Firm Scales
- 06Organizations Are Objectives, People, and Incentives
1. Key Themes
Disaggregating the Star Investor: The CAA Model Applied to Venture
The core structural innovation of a16z was borrowing Michael Ovitz's CAA playbook and applying it to the general partner role. Instead of one star investor who personally holds every relationship, the firm built specialist teams around each GP. Scott explains the original pitch: "we were basically trying to institutionalize John Doerr... could we basically uh effectively disaggregate that from the GP job, and hire professionals who could do talent networks, who could do political networks, who could do sales and marketing, and all the other things that ultimately like came to be the platform for a16z." 00:05:26 He frames the logic as a scaling problem: "at some point John has so many board seats that you time out from a GP perspective cuz you can only take so many board seats on." 00:06:57 The entrepreneur-facing version was the "reverse pitch": "you get this entire table of people whose job it is day in and day out to figure out how do we institutionalize a set of relationships and networks that'll make you successful?" 00:06:57
Marketing as a Wedge When You Lack a Track Record
Venture historically treated marketing as taboo because capital was scarce and the VCs held all the power. a16z had no portfolio history to compete on, so it changed the basis of competition. Scott: "if we can't compete on what people are competing on today, we have to change the rules of the road and go compete on something else. And so, they created this category was, 'Okay, the new venture capital firm is going to be not just capital, but it's going to be capital plus plus.'" 00:17:43 He contrasts this with incumbents: "if you go to their conference rooms, you'll see Cisco in the, you know, a poster of Cisco, and Apple, and Google... we had none of that." 00:17:43 Competitors attacked them for it ("these guys talk a big game, and they tell people stuff before they've done it"), and Scott's answer was "we're doing exactly what any entrepreneur would do, which is like we were trying to create a category." 00:20:32
Counter-Cyclical Timing and Momentum Compounding
a16z launched in the worst possible market and turned that into an advantage. Scott: "we were this shiny gold, you know, like object in 2009, when everyone else was hunkered down and worried about their portfolio companies." 00:16:08 The early wins (Skype, Nicira) funded the service model: "in order to do the Michael Ovitz business model, we had to have a enough of a fee stream to be able to hire all these other non-investing people." 00:13:30 The second fund then compounded the effect: "the second fund gave us a stacking fee stream that allowed us then to say, 'Okay, now we can actually double down on this strategy.'" 00:15:28
Founders Subsidizing the Platform
The service organization was funded by founder sacrifice at the start. Scott: "the two of them... took no salary, right, at the beginning of the company, because they wanted to basically take as much of the fees as they could to give it to me to go hire other people, you know, to build this thing out." 00:03:01 The result was scale: "we went from three of us to probably close to 100 in the first year, and then today, I think we have like 700 people." 00:04:18
Centralize, Then Federate as the Firm Scales
After roughly 10 years and about 500 people, the firm reorganized. Scott: "we started with a centralized firm, right? So, everything reported to me... What they realized over time, which was brilliant, was you can't scale a venture firm in that fashion." 00:21:02 The new structure: "we're going to have smaller investing teams that are going to be domain-specific... a crypto fund that Chris Dixon runs, and... an American Dynamism fund that David Ulevitch runs, and... an AI infrastructure that this guy Martin runs." 00:21:02 Only functions that benefit from consistency stayed central: "legal and finance... core compliance functions... investor relations, right, from an LP's perspective, their view is, 'I want to interact with Andreessen Horowitz as a firm.'" 00:21:02
Organizations Are Objectives, People, and Incentives
Scott's transferable thesis from venture to government is a simple three-part diagnostic. "all an organization is, it's a collection of people who are just aligned around a similar set of objectives... do you have the right set of objectives, do you have the right people, and then do you have a set of incentives that track to those objectives, so that when people do the things you want them to do, they get rewarded and recognized." 00:27:32 His diagnosis of government is that the third element is broken: "the incentive structure is completely screwed up, from my perspective." 00:27:32
Permissioned Risk: Fixing Government's Asymmetric Incentives
Government punishes downside and ignores upside. Scott recounts the advice he was given: "our job is to keep you out of the news." 00:28:36 His reframing: "I've been using this term 'permissioned risk,' which is deliberately different from the 'permissionless risk' that I think exists in Silicon Valley... that risk needs to be appropriately sized for the organization." 00:29:24 The sizing logic: "if you are in the Department of War, and the risk is people die, okay, like maybe we ought to have a really like low tolerance for that. But... what I do and what most people in government do, it's not life or death." 00:29:24
Merit Over Tenure: Performance Management Reform
Government rating systems provide no signal. Scott: "Historically, in government, 99.7% of people are a 3 or above, meaning literally 0.3% fall below expectations." 00:31:13 At the senior level: "something like 90% of people get ranked a 4 or a 5, meaning like literally everybody's awesome." 00:31:55 The fixes include forced differentiation ("no more than 40% of the population can be at that top ranking, and 60-plus percent of the compensation pool needs to go to those 40%") 00:32:41, eliminating "time-in-grade" promotion gating 00:33:55, and replacing self-rated questionnaires with third-party technical assessments 00:34:52.
The Demographic Cliff in the Federal Workforce
The government is badly under-indexed on young people. Scott: "7%... of the federal workforce is under the age of 30... 23% of the total US workforce is under the age of 30." 00:36:24 On the other end: "44% in government is over the age of 50. That compares with about 33% in the total US workforce." 00:36:50 The implication: "half of our workforce will retire over the next 5 or 10 years, and we are stuck with nobody to actually do the work." 00:37:12
Recruit on Self-Interest, Not Duty: The Tour-of-Duty Model
Scott rejects the "job for life" pitch. "there's not a single person under the age of 30 today who is thinking about lifetime employment." 00:38:23 The replacement pitch: "do something that's actually good for yourself, which is come spend two or three years, work on like some of the most complex, hardest problems that are out there." 00:38:23 The Tech Force program makes this concrete: "bring in a 1,000 software engineers, AI experts, data scientists to serve 2-year terms in government," with "40 private companies" doing training, and "a massive job fair" at the end. 00:38:23 The model is explicitly borrowed from the IDF cyber corps.
2. Contrarian Perspectives
Venture's Marketing Taboo Was Historical Accident, Not Wisdom
Most investors assumed marketing was beneath a serious venture firm. Scott argues it was only a byproduct of capital scarcity: "it was considered verboten to market in the venture capital business. I don't know why that was... I think it's mostly historical reason, which was you didn't need to market because... capital was scarce." 00:17:43 He adds that this applies even to the best firms: "all these guys lived in that era, right, where nobody marketed, I believe, just in part because they didn't have to market." 00:17:43 The implication is that any moat built on a scarcity that has since disappeared is vulnerable.
Silicon Valley Doesn't Love Failure: It Tolerates It
The popular narrative is that the Valley celebrates failure. Scott: "there's a whole meme in Silicon Valley, right, that Silicon Valley like loves failure, right? Like, nothing could be farther from the truth, nobody fucking likes failure, but what Silicon Valley does recognize is, look, if we're going to innovate, we're not going to get it right all the time." 00:53:07 The point is that tolerance for failure is the actual mechanism, and it must be deliberately designed into incentives.
A Self-Interested Pitch Beats a Patriotic One for Recruiting Government Talent
The natural instinct is to recruit with "serve your country." Scott's view is the reverse: "do something, you know, not just that's good for your country, uh that's fine, but like do something that's actually good for yourself." 00:38:23 David Senra endorses it: "your appealing to interest is way smarter than saying, 'Hey, here's the government. You're a citizen. Come try to do something good for the government.'" 00:40:07 And he warns that a lifetime-employment pitch actively selects the wrong people: "that's not the kind of self-motivated, driven person that we want in the government." 00:38:23
The Government's Problem Is Incentives More Than Talent
Reformers often assume government is staffed with mediocre people. Scott pushes back: "there's a lot of very good people in the federal government, so... I think a lot of this is a systems incentive problem versus necessarily a talent problem." 00:36:05 The 99.7% performance-rating statistic shows a system that cannot see its own talent.
Big-Bang Disruption Was Necessary Before Institutionalization
Against the view that government change must be incremental, Scott argues: "to change the direction of a 2.3 million person like oil tanker, you can't do gradual, incremental stuff. Like, you have to have a big bang approach." 00:44:36 Headcount fell from "roughly 2.3 million" to "just about 2 million," the lowest "as a percentage of the workforce since like 1960." His role is the follow-on: "Elon, Steve Davis, all these guys did an amazing job of like breaking glass... Now, we have to like do the long-term institutionalization of it." 00:44:36
3. Companies Identified
Skype
Communications platform, then neglected inside eBay. a16z, Silver Lake, and others bought it in an early-fund buyout. Mentioned as the early win that changed a16z's trajectory. Scott: "Skype had been bought by eBay and it was like completely neglected inside of eBay, and yet, amazingly, it had this incredible network effect." 00:12:21 The outcome: "literally 18 months later, we sold to Microsoft for four times what we paid." 00:13:30
Silver Lake
Large technology private equity firm run by Egon Durban. Partner with a16z on Skype and solved the IP-ownership impasse. Scott: "Egon's genius uh was let's actually figure out a way to work with these guys, so we actually... worked collaboratively with... these guys as a way to moderate this IP question." 00:13:30
Nicira
Software-defined networking company; Martin Casado's company, sold to Cisco early in a16z's first fund. Cited as a second early win. Scott: "his company got sold to Cisco early on in the first fund, so we had these like very quick early wins." 00:13:30
CAA (Creative Artists Agency)
Talent agency founded in 1975 by Michael Ovitz, whose team-based "phalanx" model was the template for a16z's platform. Scott: "when you would go like show up for a pitch at CAA in like 1990, where I think they had like 90% market share, they would sit around a table, and Michael would introduce you... 'meet my colleague who does nothing other than radio deals.'" 00:06:57
Kleiner Perkins
Venture firm co-founded by John Doerr, the archetype of the uber-connector GP. Mentioned as the model a16z tried to institutionalize. Scott: "John was like this ultimate uber-connector for entrepreneurs, and our basic idea was, look, could we basically institutionalize that." 00:05:26
Sequoia, Accel, Greylock, Benchmark
Incumbent top-tier venture firms that came of age when capital was scarce and marketing unnecessary. Scott on Sequoia: "an amazing, you know, player in the space." 00:17:43 Sequoia also authored the "R.I.P. Good Times" presentation in the 2009 downturn. 00:16:07
Loudcloud / Opsware
Marc and Ben's earlier company, where Ovitz sat on the board; later sold to Hewlett-Packard. Scott: "Michael had been on our board, actually, at Loudcloud and Opsware, so that's how obviously Marc and Ben knew him." 00:05:26
General Atlantic
Growth investment firm; source of David George, who built a16z's later-stage fund. Scott: "We brought in a guy named David George from GA, uh General Atlantic, who had been doing this, who was great." 00:21:02
OPM (Office of Personnel Management)
The federal HR and talent agency for roughly 2 million employees, now led by Scott. Mentioned as the institution being rebuilt. Scott: "we are the HR/talent agency for the 2.something million federal employees." 00:25:13
Tech Force (OPM program)
An elite two-year-term program to bring 1,000 software engineers, AI experts, and data scientists into government at GS-14, with 40 private-company partners. Scott: "we partnered with 40 private companies... Alphabet, and Meta, and Databricks, and all these guys." 00:38:23
National Design Studio
Gebbia-led effort to redesign government websites and a partner on automating retirement processing. Scott: "he works for Joe Gebbia now as part of this National Design Studio, which is like redesigning all the like web uh sites for the government." 00:41:03
NASA
Cited as an example of a mission-driven agency under strong leadership. Scott: "If you're interested in space, like go work at NASA. What like Jared Isaacman and NASA is doing is fucking awesome." 00:38:23
Department of Energy
Pitched as a destination for ambitious technical people. Scott: "if you want energy stuff, go to the Department of Energy, there's all kinds of cool like supercomputer stuff." 00:38:23
DOGE
The Elon Musk-led efficiency initiative. Scott credits it with breaking the system's inertia and using his office as its base. Scott: "they were executing it literally out of my office, so it turns out like my office was like the Ground Zero for like everything that was happening." 00:44:15
Airbnb
Joe Gebbia's co-founded company, mentioned as his credential. Scott: "Joe is a co-founder of Airbnb who's now running this National Design Studio." 00:47:23
NIH
National Institutes of Health, now run by Jay Bhattacharya. Mentioned in Scott's biography. Scott: "Jay Bhattacharya, who now runs the NIH." 00:25:13
IDF Cyber Corps
Israeli Defense Forces program that pulls top high-school graduates into cyber roles. It is the explicit model for Tech Force. Scott: "when they come out, every like venture capital firm is falling all over themselves to fund these guys, every like cyber company wants to hire them." 00:38:23
Hewlett-Packard
Acquirer of Scott's prior company (Opsware), referenced as his employer before a16z. Scott: "we had sold our last company to uh Hewlett-Packard." 00:01:29
Michael Dell's investment firm / Dell
Michael Dell was part of the Skype investor group. Scott: "Michael Dell was uh was part of that, too." 00:13:30
Cisco, Apple, Google
Cited as the iconic portfolio logos on Sequoia's conference-room walls, representing the track record a16z lacked. Scott: "you'll see Cisco in the, you know, a poster of Cisco, and Apple, and, you know, Google." 00:17:43
Microsoft
Acquirer of Skype 18 months after the buyout. Scott: "we sold to Microsoft for four times what we paid." 00:13:30
Databricks, Alphabet, Meta
Named Tech Force training partners. Scott: "all the names you would know, right, you know, Alphabet, and Meta, and Databricks." 00:38:23
4. People Identified
Marc Andreessen
Co-founder of a16z. Described by Scott and David as a deep business-history obsessive. Scott: "the guy is encyclopedic on so many things." 00:17:43 He also picked up on his obsessive tendencies: "if he gets excited about sushi, quite frankly, he'll eat sushi for like every meal for like a 6-month period of time." 00:10:04
Ben Horowitz
Co-founder of a16z. Described by Scott as generous and instrumental in structuring the firm's evolution. On the founders' decision to forgo salary: "they were very very magnanimous, the two of them... took no salary." 00:15:28
Michael Ovitz
Founder of CAA; former board member at Loudcloud and Opsware; informal adviser to a16z. Why mentioned: "he was very, very influential... I would call in him a lot." 00:05:26 His phalanx model is the foundation of the a16z platform.
John Doerr
Legendary Kleiner Perkins investor, the "ultimate uber-connector." Scott: "he knew every salesperson, he knew every CFO, he knew every political stuff." 00:05:26
Egon Durban
Silver Lake leader who engineered the Skype deal structure. Scott: "Egon's genius uh was let's actually figure out a way to work with these guys." 00:13:30
Martin Casado
a16z partner whose company Nicira was sold to Cisco; now runs AI infrastructure investing. Scott: "his company got sold to Cisco early on in the first fund." 00:13:30 and "an AI infrastructure that this guy Martin runs." 00:21:02
Chris Dixon
Runs a16z's crypto fund. Scott: "a crypto fund that Chris Dixon runs." 00:21:02
David Ulevitch
Runs a16z's American Dynamism fund. Scott: "an American Dynamism fund that David Ulevitch runs." 00:21:02
David George
Former General Atlantic investor who built a16z's later-stage fund. Scott: "We brought in a guy named David George from GA... who was great." 00:21:02
Chris Dixon, David Ulevitch, Martin Casado as federated domain leaders
Together they illustrate the shift from centralized to vertical structure. See individual entries above.
Alan Garber
Stanford professor Scott worked for on prostate-cancer screening research; now president of Harvard. Scott: "this guy named Alan Garber, who's actually now the president of Harvard." 00:25:13
Jay Bhattacharya
Stanford researcher and Scott's former boss; now runs the NIH. Scott: "Jay was a researcher at Stanford, I was his grunt... who now runs the NIH." 00:25:13
Elon Musk
Led DOGE and identified the retirement-paper problem. Scott: "Elon identified this and rightly so, he's like, 'This is insane.'" 00:47:23 On method: "to change the direction of a 2.3 million person like oil tanker, you can't do gradual, incremental stuff." 00:44:36
Steve Davis
Day-to-day leader of DOGE. Scott: "Steve Davis was kind of the day-to-day person running it." 00:43:33
Joe Gebbia
Airbnb co-founder; leads the National Design Studio and partnered on retirement digitization. Scott: "Joe is a co-founder of Airbnb who's now running this National Design Studio." 00:47:23
Edward "Big Balls" Coristine
Young DOGE engineer used as the emblem of merit-versus-credentials. Scott: "He's one of like the most brilliant software developers around." 00:41:03 The quote that frustrated Scott: "'We would never hire Ed in government, because he didn't have a college degree, and he didn't have 5 years of work experience.'" 00:41:03
Jared Isaacman
NASA leader. Scott: "What like Jared Isaacman and NASA is doing is fucking awesome." 00:38:23
Robert Redford
Used as the illustrative actor in the CAA pitch. Scott: "you're Robert Redford, right, and you have an agent." 00:06:57
Janus and Niklas
Skype's original founders whose potential IP claim complicated the deal. Scott: "what if Janus and Niklas come out of the woodwork and say they own it." 00:13:30
Arsho
Marc's assistant. Scott: "Arsho, who's his assistant, was incredibly generous with us." 00:10:04
Michael Dell
Skype investor group member and admirer of Egon Durban. David: "Michael Dell, I just saw him a few days a few nights ago, he speaks very highly of him." 00:13:26
David Senra
Host of Founders; interviewer in this episode. Scott acknowledges the Marc episode he did: "the amount of business history that's in that guy's head." 00:16:57
Scott Kupor
Former a16z first employee, now OPM Director. His own record: "16 and 1/2 years" at a16z 00:09:34, with about "15 companies that I invested in, about 10 of which that I was sitting on the board of." 00:21:02
5. Operating Insights
Hire the Operating Layer Before You Know the Job Description
Scott's job description was "There was no job description!... 'we're going to invest, and you need to figure out everything else we need to do to build the firm.'" 00:03:01 The structural lesson is to delegate the entire non-core surface area to a single accountable builder, and let them hire domain experts. The resulting hiring pace was "three of us to probably close to 100 in the first year." 00:04:18
Run a Reverse Pitch to Show, Not Tell, Your Platform
When an entrepreneur pitched a16z, "we would bring the team in, and we would do the reverse pitch to them." 00:06:57 This converted an abstract value proposition into an immediate demonstration of the whole table of specialists, which is a tactic any service-heavy firm can use in sales.
Time Reorganizations to Business Needs and Acknowledge the Ego Cost
Scott describes his own resistance to the decentralization and how Marc and Ben handled it: "Marc and Ben, to their credit, were like, 'Look, we're not saying you're not doing a good job. We're saying like the needs of the business have changed... let's go find other ways in which you can add value to the business.'" 00:21:02 The tactic is to separate the person's performance from the structural change and give them a new arena (Scott moved into later-stage investing).
Know Your Edge Before Choosing Your Role
Scott stayed out of early-stage investing because "if you don't understand databases, for example, you can hear 10 pitches about database companies, and unless you have that depth of knowledge, the honest answer is, you have no fucking clue like which one is the right one to invest in." 00:21:02 He instead took on later-stage, where "the evaluation of the company was more about the operational successes... from like 1 to infinity." 00:21:02
Run Compensation Pools With Forced Differentiation
Scott's policy: "no more than 40% of the population can be at that top ranking, and 60-plus percent of the compensation pool needs to go to those 40% of the people." 00:32:42 He notes that a flat bonus has no incentive value: "I give you a $1,000, and it has no incentive value, it has no retentive value." 00:32:42 The principle applies to any organization where ratings have inflated.
6. Overlooked Insights
Government Has No Canonical Employee Record Until Retirement
Buried in the retirement-mine story is a structural flaw: "we do not have the canonical history of your government service until you literally decide to retire... Literally, part of the retirement process is we have to create that record." 00:47:23 Scott's fix is consolidating "120 different systems into a single system" and cutting spend "from $2 billion a year to $40 million a year." 00:47:23 That is a roughly 95% cost reduction, signaling a large addressable market for HR, payroll, and identity-record modernization in public-sector software.
The Skype Deal Was an LP-Narrative Risk That Worked
Scott mentions in passing that the buyout contradicted the firm's pitch: "we had just gone on the road and told all of our investors we're doing early-stage venture investing... it was clearly very different than the strategy we had laid out." 00:13:30 The overlooked point is that a16z took on style-drift risk in its first fund and won, then used the narrative momentum to raise Fund II "well ahead of what we had planned." 00:13:30