David Weiden
Founding Partner & Managing Director at Khosla Ventures
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Founding Partner at Khosla Ventures since 2006, ranked #95 on 2017 Forbes Midas List. Brings operational expertise (Netscape, AOL, Tellme) to seed/Series A investments. Portfolio 31% fintech (Upstart, Fundbox, OnDeck), 23% enterprise SaaS (Okta, RingCentral). Known for coaching on unit economics and cash payback metrics.
Background
David Weiden is a Founding Partner and Managing Director at Khosla Ventures, where he has worked since 2006 1. He focuses on internet software and services 1. He has been recognized by Fortune and Forbes as one of the top technology investors, ranking #95 on the Forbes Midas List in 2017 2.
Before joining Khosla Ventures, Weiden spent five years at Tellme Networks as VP of Marketing and Business Development, where he used a quantitative decision-making framework called RIFLE to grow revenue to over $100 million; Tellme was ultimately acquired by Microsoft for more than $700 million 1 3. Previously, he led AOL’s communications, community, and instant messaging product divisions as they surpassed 50 million users worldwide 1. Earlier in his career he worked at Netscape, where he learned product management alongside Marc Andreessen and Ben Horowitz 3. He began his career at Morgan Stanley as an analyst and at McCaw Cellular (now AT&T) in door-to-door sales 1 3.
Weiden holds a bachelor’s degree magna cum laude with highest honors in organizational behavior and economics from Harvard University 1.
Stated Thesis
Weiden publicly describes his investment focus as internet software and services 1. According to his firm profile and public talks, he coaches founders on go-to-market metrics and unit economics, emphasizing cash payback, product-market fit, and the dangers of premature scaling 4 3.
In his “Success, Failure & Numbers” presentation at the Khosla Ventures CEO Summit, Weiden articulated his belief that quantitative discipline is the missing ingredient in most startup failures. He has stated that most VC-backed companies achieve working products, customer traction, and positive gross margins, yet still fail because either initial traction is unsustainable or the cost of reaching mainstream customers is too high 3.
He has also expressed a strong preference for ethical founders, and an emphasis on real business economics over vanity metrics 3 4.
Inferred Thesis
Based on 26 verified investments below, Weiden’s actual investment behavior shows the following patterns:
Sector breakdown (of 26 verified investments): - Fintech/financial services: 8 of 26 (31%) — Fundbox, Upstart, OnDeck Capital, Swift Financial, True Link Financial, Azibo, Basis, BOKU - Enterprise/SaaS: 6 of 26 (23%) — Okta, RingCentral, Opsware, LogMeIn, WideOrbit, Yammer - Consumer internet/social: 5 of 26 (19%) — Slide, GroupMe, iLike, Lookout, GoodTrust - Proptech/real estate: 4 of 26 (15%) — Roofstock, Homebound, Lessen, Fernish - Other (hardware, telecom, data): 3 of 26 (12%) — AliphCom/Jawbone, Bitfone, YuMe
Stage distribution: Weiden invests across seed through Series B, though his most notable exits (Okta, RingCentral, Upstart) came from early-stage (Series A/B) investments where he joined the board. His more recent investments include seed-stage bets such as GoodTrust ($5M seed, 2021) and Azibo ($10.5M seed, 2020) 5 11.
Geographic focus: Portfolio is heavily concentrated in the San Francisco Bay Area and broader US, consistent with Khosla Ventures’ overall geographic focus.
Board involvement: Weiden takes an active board role in many investments. He currently serves as a director at Fundbox, Roofstock, and Azibo 6. He previously served as independent director at RingCentral (2006-2015) and YuMe (2009-2015), and as a director at ZocDoc, Lookout, Swift Financial, WideOrbit, AliphCom, AdReady, BOKU, Evolv, and Nirvanix 6.
Notable pattern — operational coaching: Unlike many VCs, Weiden brings deep operating experience (Netscape, AOL, Tellme) and is known for hands-on coaching of founders on go-to-market metrics and unit economics 3 4. This is consistent with Khosla Ventures’ broader “venture assistance” model.
Notable gap: Despite Khosla Ventures’ heavy involvement in climate tech, biotech, and AI, Weiden’s personal portfolio skews toward fintech, enterprise software, and proptech. His investments do not prominently feature deep tech, climate, or biotech companies.
Portfolio
| Company | Year | Stage | Source |
|---|---|---|---|
| Basis | 2026 | Series B (follow-on) | 7 |
| Homebound | 2022 | Series C | 8 |
| GoodTrust | 2021 | Seed | 5 |
| Fundbox | 2021 | Series D (follow-on) | 9 |
| Lessen | 2021 | Series A | 10 |
| Breeze | ~2021 | Seed | 10 |
| True Link Financial | 2020 | Series B | 12 |
| Fernish | 2020 | Series A | 13 |
| Azibo | 2020 | Seed | 11 |
| Fundbox | 2019 | Series C (follow-on) | 9 |
| Swift Financial | ~2015 | Unknown | 6 |
| Fundbox | 2015 | Series B (follow-on) | 9 |
| Roofstock | 2015 | Series A | 14 |
| Fundbox | 2014 | Series A | 9 |
| Upstart | ~2014 | Early stage | 1 |
| OnDeck Capital | ~2013 | Early stage | 2 |
| Nirvanix | ~2012 | Unknown | 6 |
| Okta | 2011 | Series B | 15 |
| GroupMe | 2011 | Series B | 16 |
| Yammer | ~2010 | Early stage | 2 |
| YuMe | ~2009 | Early stage | 6 |
| Climate Corporation | ~2008 | Early stage | 2 |
| Slide | ~2007 | Early stage | 2 |
| iLike | ~2007 | Early stage | 2 |
| RingCentral | 2006 | Series A | 17 |
| Bitfone | ~2006 | Early stage | 2 |
| AliphCom/Jawbone | ~2006 | Early stage | 2 |
| WideOrbit | ~2006 | Early stage | 6 |
| Opsware | ~2006 | Early stage | 2 |
| LogMeIn | ~2006 | Early stage | 2 |
This table represents investments attributable specifically to David Weiden. As a founding partner at Khosla Ventures since 2006, he has been involved in numerous deals; the full count is likely higher than what is publicly documented here.
In Their Own Words
“If you overlay quantitative analysis on your intuition, it is better than your intuition.” — David Weiden, Khosla Ventures CEO Summit, “Success, Failure & Numbers” presentation 3
“Don’t confuse activity with accomplishment.” — David Weiden, Khosla Ventures CEO Summit 3
“All of us have experienced the loss of a loved one. GoodTrust solves the growing issue of what happens to our priceless digital assets, online accounts and assets when we die, protecting our precious memories and legacy for everyone.” — David Weiden, Khosla Ventures, on investing in GoodTrust, December 2021 5
“Construction is massive in terms of financial, societal, and environmental impact with significant opportunity for innovation to disrupt and improve it in a myriad of ways.” — David Weiden, on investing in Homebound’s Series C, TechCrunch, February 2022 8
On the danger of custom metrics: Weiden has cited WeWork’s use of “Community Adjusted EBITDA” as a cautionary tale, noting that founders inventing their own metrics to make numbers look better is a red flag 3.
On founder skills gaps: Weiden has observed that founders excel at vision, storytelling, courage, and building, but often lack comfort with quantitative analysis and financials; success requires either strengthening these skills or elevating team members in these areas 3.
What Founders Say
Jon Chu, a colleague at Khosla Ventures, publicly stated on X: “David Weiden is one of the best and most underrated investors of all time as evidenced by returns.” 18
No independently sourced founder testimonials from portfolio company founders were found through dedicated searching. Weiden is known to be active in CEO summits and founder coaching at Khosla Ventures, where he has conducted onstage conversations with portfolio founders including Okta CEO Todd McKinnon and Upstart CEO Dave Girouard 19, but public founder quotes about the experience of working with Weiden specifically are not widely available.
Connections
- Board member, Fundbox — Director (current) 6
- Board member, Roofstock — Director (current) 6
- Board member, Azibo — Director (current) 6
- Former independent director, RingCentral (2006-2015) 6
- Former independent director, YuMe (2009-2015) 6
- Former director, ZocDoc 6
- Former director, Lookout 6
- Former director, Swift Financial (acquired by PayPal, 2017) 6
- Former VP, Tellme Networks — worked with team that sold to Microsoft for $700M+ 1
- Former employee, Netscape — worked alongside Marc Andreessen and Ben Horowitz 3
- Khosla Ventures CEO Summit host — regular presenter and interviewer alongside portfolio CEOs including Todd McKinnon (Okta) and Dave Girouard (Upstart) 19
- Money20/20 US speaker (2018) 20
Sources
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Khosla Ventures, “David Weiden” team page, accessed March 2026. https://www.khoslaventures.com/team/david-weiden↩↩↩↩↩↩↩↩↩
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Forbes Midas List 2017, #95 David Weiden, accessed March 2026. https://www.mrowl.com/user/araichur/forbes_themida/_95davidweiden↩↩↩↩↩↩↩↩↩↩
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“Letter #209: David Weiden (2024)” by Kevin Gee, A Letter a Day (Substack), accessed March 2026. https://aletteraday.substack.com/p/letter-209-david-weiden-2024↩↩↩↩↩↩↩↩↩↩↩↩
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VCSheet, “David Weiden (Khosla Ventures),” accessed March 2026. https://www.vcsheet.com/who/david-weiden↩↩↩
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PR Newswire, “GoodTrust Closes $5M Seed Round,” December 20, 2021, accessed March 2026. https://www.prnewswire.com/news-releases/goodtrust-closes-5m-seed-round-to-fuel-mission-to-protect-and-organize-everyones-digital-life-and-legacy-301448125.html↩↩↩
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MarketScreener, “David Weiden: Positions, Relations and Network,” accessed March 2026. https://www.marketscreener.com/insider/DAVID-WEIDEN-A07JBB/↩↩↩↩↩↩↩↩↩↩↩↩↩↩
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CPA Practice Advisor, “Basis Raises $100 Million to Deploy AI Agents for Accounting Firms,” February 24, 2026, accessed March 2026. https://www.cpapracticeadvisor.com/2026/02/24/basis-raises-100-million-to-deploy-ai-agents-for-accounting-firms/178759/↩
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TechCrunch, “Tech-enabled homebuilder Homebound raises $75M Series C led by Khosla,” February 15, 2022, accessed March 2026. https://techcrunch.com/2022/02/15/homebound-raises-75m-in-khosla-led-series-c/↩↩
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TechCrunch, “Fundbox, a fintech focused on SMBs, raises $100M at a $1.1B valuation,” November 30, 2021, accessed March 2026. https://techcrunch.com/2021/11/30/fundbox-raises-100m/↩↩↩↩
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Evalyze.ai, “David Weiden Investor Profile,” accessed March 2026. https://www.evalyze.ai/investors/david-weiden↩↩
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Benzinga, “Azibo Secures $19M Series A Led by SVB Capital,” January 11, 2022, accessed March 2026. https://www.benzinga.com/pressreleases/22/01/n24998877/azibo-secures-19m-series-a-led-by-svb-capital↩↩
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Business Wire, “True Link raises $35 million Series B led by Khosla Ventures and Centana Growth Partners,” July 28, 2020, accessed March 2026. https://www.businesswire.com/news/home/20200728005142/en/True-Link-raises-35-million-Series-B-led-by-Khosla-Ventures-and-Centana-Growth-Partners↩
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GeekWire, “Furniture rental startup Fernish raises $15M from Khosla, Jeff Wilke, Spencer Rascoff, others,” May 2020, accessed March 2026. https://www.geekwire.com/2020/furniture-rental-startup-fernish-raises-15m-khosla-ventures-jeff-wilke-spencer-rascoff/↩
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PR Newswire, “Roofstock raises $240M at $1.9B valuation,” accessed March 2026. https://www.prnewswire.com/news-releases/roofstock-raises-240m-at-1-9b-valuation-to-expand-access-to-real-estate-investing-301499833.html↩
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TechCrunch, “Khosla, Greylock, Andreessen Horowitz Put $16.5M In Enterprise Cloud App Management Startup Okta,” August 8, 2011, accessed March 2026. https://techcrunch.com/2011/08/08/khosla-greylock-andreessen-horowitz-put-16-5m-in-enterprise-cloud-app-management-startup-okta/↩
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FinSMEs, “GroupMe Closes $10.6M Series B Financing Round,” January 2011, accessed March 2026. https://www.finsmes.com/2011/01/groupme-closes-10-6m-series-b-financing-round.html↩
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Wikipedia, “RingCentral,” accessed March 2026. https://en.wikipedia.org/wiki/RingCentral↩
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Jon Chu (@heyjchu) on X, August 6, 2024, accessed March 2026. https://x.com/heyjchu/status/1820949360227860485↩
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Khosla Ventures, “CEO Summits,” accessed March 2026. https://www.khoslaventures.com/entrepreneurs/ceo-summits↩↩
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Money20/20 US 2018, “David Weiden schedule,” accessed March 2026. https://money2020us2018.sched.com/speaker/david_weiden.1yd9f959↩