Scott Weiss

Background

Scott Weiss is an American venture capitalist who joined Andreessen Horowitz (a16z) in March 2011 as the firm’s fourth general partner ¹². A native of Sarasota, Florida, Weiss received a Bachelor of Arts from the University of Florida and an M.B.A. from Harvard Business School ³⁴.

Weiss began his career at Electronic Data Systems, where he spent five years ³⁴. He then worked as an associate at McKinsey & Company ³⁴. In the mid-1990s, he joined Hotmail as employee number 13, where he was responsible for partnership and revenue-generating business development efforts ³⁴. Hotmail was acquired by Microsoft in December 1997 ³. After the acquisition, Weiss headed MSN business development at Microsoft ³⁴.

Weiss subsequently started an e-commerce company, which he shut down during the 1999 dot-com downturn ⁵. He then joined Idealab, the business incubator founded by Bill Gross, as managing director and entrepreneur in residence, where he helped shut down or sell several consumer companies ⁴⁵. It was at Idealab that he met Scott Banister, with whom he co-founded IronPort Systems in 2001 ⁴⁵.

IronPort Systems, based in San Bruno, California, was a provider of messaging security appliances specializing in enterprise spam and spyware protection ⁶. Under Weiss’s leadership as CEO, IronPort grew from two people to 450 employees and a $200 million annual run rate ⁵⁷. On January 4, 2007, Cisco announced a definitive agreement to acquire IronPort for approximately $830 million in cash and stock ⁶. Following the acquisition, Weiss served as Vice President and General Manager of Cisco’s Security Technology Group until June 2009 ⁴⁸.

After leaving Cisco, Weiss joined Andreessen Horowitz in March 2011 ¹². He is credited with introducing 360-degree feedback performance reviews of partners by other partners, venture firms, and entrepreneurs at portfolio companies – an unusual practice for venture capital firms that he proposed during his interview process ³⁴.

In January 2016, Weiss announced he would no longer invest in new companies on behalf of a16z, choosing instead to focus on his existing board seats and spend more time with his family ²⁹. He currently serves as a board member at unitQ ⁷.

Stated Thesis

Weiss has publicly articulated a preference for enterprise investments at the earliest stages. He stated that a16z will “often do an enterprise series A when it is at the idea stage or an unproven prototype” because “enterprise opportunities usually include a unique technology advantage or business insight borne out of the entrepreneur’s deep understanding of the subject area” ¹⁰.

For consumer investments, Weiss described a higher bar: the firm is “more likely to become a seed investor or wait until the business has caught ‘lightning in a bottle’ at the B round” since “many of the consumer ideas are primarily business model innovations” that require proof of product-market fit ¹⁰.

Weiss has emphasized the importance of recruiting and team-building for startups, coining the concept of being “too hungry to eat” at a16z: “We often see startups that are so entrenched in the product that the founders forget they need muscle to grow” ¹¹.

On board governance, Weiss has advocated for selecting board members who have operating experience, stating that board members “need to respond to texts within hours and emails or phone calls within 24 hours – no excuses” and must “materially contribute to the success of the business” through introductions, candidate interviews, and management coaching ¹².

Inferred Thesis

Based on 14 verified investments in the portfolio table below, the following patterns emerge. Note: this is a limited sample relative to Weiss’s likely total deal involvement at a16z from 2011-2016, so percentages should be treated as directional rather than definitive.

Sector allocation (14 verified investments): - Enterprise/SaaS/DevOps: 5 companies (36%) – Optimizely, Platfora, Distelli, Return Path, unitQ - Security/fraud: 4 companies (29%) – Silver Tail Systems, Bluebox, Pindrop, Jumio - Consumer/social/mobile: 3 companies (21%) – Lyft, Skout, App.net - Fintech/payments: 2 companies (14%) – Dwolla, Quirky (hardware/consumer invention platform)

Stage distribution: - Predominantly Series A and Series B investments, consistent with a16z’s typical entry points during 2011-2016

Key patterns: - Strong security focus reflecting Weiss’s IronPort/Cisco background (4 of 14 verified investments, 29%) - Enterprise investments made at earlier stages (idea/prototype) vs. consumer investments requiring traction, consistent with his stated thesis - Board-heavy approach: Weiss took board seats at nearly every company he led, a distinctive practice reflecting his belief in active board governance - Mixed outcomes: several successful exits (Silver Tail to EMC/RSA in 2012, Lyft IPO 2019) alongside shutdowns (App.net, Quirky bankruptcy)

Notable gap: Despite his stated preference for enterprise, 3 of 14 verified investments (21%) were consumer/social companies (Lyft, Skout, App.net), suggesting broader deal scope than his public positioning implies.

Portfolio

This table represents a partial view of Weiss’s deal involvement at a16z from 2011 to 2016. Weiss held board seats at all listed companies except where noted ⁴⁸.

In Their Own Words

“Integrating IronPort’s messaging security technology with Cisco’s Self-Defending Network will enable a new level of defense for our customers.” – Scott Weiss, IronPort CEO, Cisco acquisition announcement, January 2007 ⁶

“At Andreessen Horowitz, we talk about the notion of being ‘too hungry to eat.’ That’s to say, we often see startups that are so entrenched in the product that the founders forget they need muscle to grow.” – Scott Weiss, a16z blog, “Building Your Recruiting Muscle” ¹¹

“We will often do an enterprise series A when it is at the idea stage or an unproven prototype… in contrast to many of the consumer ideas that are primarily business model innovations.” – Scott Weiss, a16z blog, “A Clarification and an Apology,” October 2013 ¹⁰

“The founders have taken a core Google competency and are making it their life’s work to extend it to the rest of the world, big or small.” – Scott Weiss on Optimizely investment, a16z blog, May 2014 ²⁰

“Optimizely is the clear leader in a huge and new must-have SaaS category.” – Scott Weiss, a16z blog, May 2014 ²⁰

“Right now, nobody is doing quite what Dwolla has figured out.” – Scott Weiss on Dwolla investment, 2013 ¹⁸

“There is an indomitable appetite for good security technology. This is not a bandaid, this saves real money for users immediately.” – Scott Weiss on Pindrop investment, 2013 ¹⁹

“I have so much respect for people who fought online criminals for eBay and PayPal.” – Scott Weiss on Silver Tail Systems team, a16z blog ¹³

“I’ve now reached a point where I’ve decided to shift the equation… The time with them is very precious, and it doesn’t escape me how lucky I am to be able to choose to be with them while I can.” – Scott Weiss, a16z blog, “An Update,” January 2016 ⁹

What Founders Say

No independently sourced founder testimonials found. Weiss’s blog posts reference positive founder relationships but no independent third-party founder quotes about working with him could be verified through public sources.

Connections

• Co-founder, IronPort Systems (2001-2007) – alongside Scott Banister ⁴⁵
• Board member, Lyft – replaced by Ben Horowitz on board in 2016 ¹⁷²¹
• Board member, App.net/Mixed Media Labs – replaced Marc Andreessen on board to avoid conflict of interest (Andreessen sat on Facebook’s board) ¹⁶
• Board member, unitQ – current board seat ⁷
• VP & GM, Cisco Security Technology Group (2007-2009) – following IronPort acquisition ⁴⁶
• Employee #13, Hotmail (1996-1998) – pre-Microsoft acquisition ³⁴
• Managing Director/EIR, Idealab (~2000-2001) – where he met IronPort co-founder Scott Banister ⁴⁵

Sources