Scott Kupor on Building a16z and Rebuilding the Federal Workforce
Scott Kupor on Building a16z and Rebuilding the Federal Workforce
Podcast56 min 46 sec
Listen to Episode
Note: AI-generated summary based on third-party content. Not financial advice. Read more.
Quick Insights

The Skype transaction is a historical example, not a current public-stock opportunity: investors reportedly sold it to Microsoft (MSFT) about 18 months later for four times their purchase price. The discussion provides no current investment thesis or price target for MSFT, eBay (EBAY), or Cisco (CSCO), so it does not support a buy recommendation for those stocks.

Detailed Analysis

Skype (Private company; no current public ticker)

  • A16Z invested in Skype shortly after closing its first fund, alongside Silver Lake and Michael Dell.
  • Skype was then part of eBay and was described as neglected despite strong subscriber growth and network effects.
  • The deal faced uncertainty over whether Skype’s original founders owned key intellectual property. The investors worked with them to address that issue.
  • The investment was sold to Microsoft about 18 months later for four times the purchase price, according to the transcript. That was the deal’s reported return, not a return available from buying a public Skype stock.

Takeaways

  • The story highlights how growing network effects can make an overlooked business attractive, but the transcript also describes a material IP-ownership risk that investors had to resolve.
  • Treat this as a historical deal example, not a current investment opportunity: Skype is not presented as a standalone public stock, and no current valuation or recommendation is discussed.

eBay (EBAY)

  • Skype was part of eBay before the investor group bought it. The transcript says Skype was “completely neglected” inside eBay while its subscriber base continued to grow.
  • No view is offered on eBay’s current business, stock, or valuation.

Takeaways

  • The account suggests that a larger company’s handling of a business can differ from that business’s underlying growth prospects. It does not, by itself, establish an investment case for eBay.

Microsoft (MSFT)

  • Microsoft bought Skype from the investor group about 18 months after the investment, at a price described as four times what the group paid.
  • The transcript gives no further assessment of Microsoft’s investment merits or current prospects.

Takeaways

  • The transaction illustrates how a strategic buyer can provide an exit for investors in a private company. It is not a price target or a recommendation to buy Microsoft shares.

Cisco (CSCO)

  • The speakers mention an early A16Z investment in a networking company transcribed as “Nasira.” They say the company was sold to Cisco.
  • The company name and deal details are unclear in the transcript. No investment thesis or current view of Cisco is provided.

Takeaways

  • The anecdote points to early networking-sector activity at A16Z, but it does not support a specific conclusion about Cisco stock.

Silver Lake (Private investment firm)

  • Silver Lake partnered with A16Z on the Skype transaction. The discussion describes the deal as a buyout and says Michael Dell also participated.
  • No information is given about Silver Lake’s current investments, performance, or terms of participation.

Takeaways

  • The deal shows how venture firms may sometimes participate in transactions outside traditional early-stage investing. Silver Lake is not presented as a publicly traded investment.

Alphabet (GOOGL, GOOG), Meta (META), and Databricks (Private company)

  • These companies are named as among roughly 40 private-sector partners in the federal government’s TechForce program.
  • The partners are expected to provide training and career development to technical employees serving two-year government terms, with the aim of preparing them for later private-sector jobs.
  • They are mentioned as program partners, not as A16Z portfolio investments or as stock recommendations.

Takeaways

  • The discussion points to a potential talent pipeline connecting government technology work with private-sector employers. It offers no company-specific financial outlook or investment recommendation.

Venture capital platform model and technology themes

  • A16Z’s model combines capital with services such as talent, sales and marketing, business development, and government relations.
  • The speakers say early deal successes, including Skype and the networking investment, helped A16Z raise its next fund and expand those services.
  • The firm later organized investing teams around areas including crypto, healthcare, bio, infrastructure, and American Dynamism.
  • The transcript mentions a crypto-focused fund but names no cryptocurrency or token. It also discusses software, AI, data science, space, energy, and government modernization without naming a specific publicly traded investment tied to those themes.

Takeaways

  • A potential investment theme raised by the discussion is that specialized expertise and operational support may help technology companies as they grow. The transcript provides no fund terms, performance figures, valuations, or specific current investment opportunities.
  • No cryptocurrency investment, token, price target, or timeline is discussed.

Ask about this postAnswers are grounded in this post's content.
Episode Description
Scott Kupor helped build a16z from three people into a firm with hundreds of employees. Now, as Director of the U.S. Office of Personnel Management, he’s applying some of the same lessons about talent, incentives, and organizational design to a workforce of roughly two million federal employees. Scott joins Founders host David Senra to tell the story of a16z’s earliest days, from joining Marc Andreessen and Ben Horowitz during the 2008 financial crisis to borrowing Michael Ovitz’s CAA model to build a venture firm around specialized networks and services for founders. He explains why a16z chose to market itself when venture firms traditionally didn’t, how early wins like Skype accelerated the firm’s growth, and why it eventually reorganized around specialized investing teams. Then they turn to Scott’s move into government. He lays out his effort to build a more merit-based federal workforce, attract younger technical talent, and create what he calls “permissioned risk” so government employees can actually try new things. That includes everything from changing how performance and promotions work to replacing a retirement process that still relied on hundreds of millions of pieces of paper stored in an underground Pennsylvania mine. Resources: U.S. Office of Personnel Management: https://www.opm.gov/ Federal early-career opportunities: https://earlycareers.gov/ Follow Scott Kupor on X: https://x.com/skupor Follow David Senra on X: https://x.com/davidsenra  Stay Updated: Find a16z on YouTube: YouTube Find a16z on X Find a16z on LinkedIn Listen to the a16z Show on Spotify Listen to the a16z Show on Apple Podcasts Follow our host: https://twitter.com/eriktorenberg Please note that the content here is for informational purposes only; should NOT be taken as legal, business, tax, or investment advice or be used to evaluate any investment or security; and is not directed at any investors or potential investors in any a16z fund. a16z and its affiliates may maintain investments in the companies discussed. For more details please see a16z.com/disclosures. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.
About The a16z Show
The a16z Show

The a16z Show

By Andreessen Horowitz

The a16z Podcast discusses tech and culture trends, news, and the future – especially as ‘software eats the world’. It features industry experts, business leaders, and other interesting thinkers and voices from around the world. This podcast is produced by Andreessen Horowitz (aka “a16z”), a Silicon Valley-based venture capital firm. Multiple episodes are released every week; visit a16z.com for more details and to sign up for our newsletters and other content as well!