Gary Benitt
InvestorGeneral Partner at Social Leverage
San Diego, California, United States
Writes $100K – $500K checks
About
Gary Benitt is a serial founder‑operator and VC with two SaaS exits (Goowy Media to AOL; Assistly to Salesforce), known for strict price discipline and hands‑on boardwork in B2B/AI-enabled SaaS.
Gary Benitt @garybenitt
So much fun building this, or more accurately orchestrating @claudeai to do the heavy lifting. Shows me that pretty much anyone could do anything that they want. It's a whole new world. https://t.co/wI2Kxil1Oi
Feb 22, 2026 · ♥ 3 · ⇄ 2
Gary Benitt @garybenitt
Every AI company pitching "enterprise copilot" is going to lose to the ones building for a single job function. AI PM. AI SDR. AI recruiter. Depth beats breadth. The workflow is the moat.
Feb 2, 2026 · ♥ 3 · ⇄ 1
Gary Benitt @garybenitt
Nobody breaks down the world of financial speculation quite like my biz partner @howardlindzon. The degenerate economy is global, inevitable…and a lot more fun than you think. https://t.co/3C29m9ZcJB
Sep 23, 2025 · ♥ 1
Invests in
ConsumerCrypto & Web3Enterprise SoftwareFintechSaaS
Experience
- Social Leverage LLCManaging Partnercurrent2014 — presentSan Diego
- BirdwatchBoard Membercurrent2023 — present
- SurfboardBoard Membercurrent2022 — present
- Sequel.ioBoard Observercurrent2021 — present
- WallaBoard Membercurrent2021 — present
- FlareBoard Membercurrent2020 — present
- CarpayBoard Membercurrent2020 — present
- LogixboardBoard Membercurrent2019 — presentGreater Seattle Area
- Robin HealthcareBoard Observercurrent2021 — presentSan Francisco Bay Area
- Robin HealthcareBoard Member2017 — 2021San Francisco Bay Area
- B Squared Ventures LLCManaging Partnercurrent2011 — presentSan Francisco
- HelioseBoard Observer2023 — 2024
- StocktwitsBoard Member2020 — 2024
- Beyond PricingBoard Member2015 — 2022San Francisco Bay Area
- KustomerAdvisor2015 — 2022Greater New York City Area
- Civic TechnologiesBoard Observer2021
- Civic TechnologiesBoard Member2016 — 2021
- 1upHealth, Inc.Board Observer2018 — 2021
- ProducePayBoard Observer2016 — 2021
- San Diego Venture GroupBoard Member2018 — 2019Greater San Diego Area
Education
- NYU Stern School of BusinessBS, Finance, Information Systems1992 — 1996
Skills & more
+12 more
AnalyticsMobile ApplicationsOnline AdvertisingVenture CapitalMergersE-commerceUser ExperienceSEOSaaSSalesforce.comEnterprise SoftwareLeadershipLanguages English · Russian
From Gary's professional profile.
Same school
Also attended NYU Stern School of Business367
+ 361 more
Shared employers
Also worked at Kustomer9
+ 3 more
Also worked at 1upHealth, Inc.2
Also worked at AOL LLC91
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+ 85 more
Also worked at Goowy Media, Inc.1
Deals · 2
Robin HealthcareBoard seat
via Social Leverage · filed Dec 2017 · $3.4M raise
StocktwitsBoard seat
via Social Leverage · filed Jun 2016 · $1.2M raise
Attribution from SEC filings, press coverage, and firm rosters.
Colleagues at Social Leverage
Network9
Investors connected to Gary in public investor directories — a warm-intro map.