OpenSky Ventures Research
Investment Thesis
OpenSky Ventures is a seed-stage venture capital firm founded in 2022 and headquartered in Los Angeles, California. The firm was co-founded by Josh Resnick and Josh Payne — two serial entrepreneurs with a combined track record of multiple successful exits — alongside Managing Partner Brian MacMahon. Their stated mission is to back exceptional founders at the earliest stages of their ventures in the future of commerce.
The core thesis centers on the intersection of consumer brands, commerce infrastructure, and technology-enabled commerce experiences. OpenSky invests in ambitious, passionate, gritty, and disruptive founders who want to reshape how products are discovered, purchased, and experienced. The partners bring a uniquely operator-centric lens to early-stage investing: they have personally built and exited companies at scale, and they leverage this experience to provide hands-on support beyond just capital.
Sector Focus
OpenSky's portfolio spans the full commerce spectrum:
Commerce Infrastructure & SaaS:
- AI-powered customer service and automation tools for e-commerce merchants
- Affiliate and creator marketing platforms connecting brands to audiences
- Data intelligence and predictive analytics for retail and commerce
- Email marketing and CRM tools for DTC brands
Consumer Brands (DTC):
- Premium food and beverage brands (tinned seafood, nootropic drinks, natural beverages)
- Home and personal care
- Pet health and pharmacy
- Apparel and lifestyle products
Commerce Platforms:
- Marketplaces and resale platforms
- Commerce + content hybrid platforms
- Creator economy monetization tools
Notable portfolio companies include Siena AI (AI-powered autonomous customer service for e-commerce), Levanta (affiliate marketing platform for Amazon/Shopify sellers), Daash Intelligence (AI predictive commerce intelligence), Fishwife (premium tinned seafood brand), and Magic Mind (mental performance beverage).
Stage Focus
OpenSky is primarily a Seed and Series A investor, with occasional pre-seed checks for exceptional founding teams. They typically aim to be among the first institutional investors in a company, often before traditional metrics-driven funds would engage. Their preferred entry point is when a founder has a compelling vision, early traction, and a product that addresses a clear commerce pain point.
Check Size
OpenSky's individual check sizes are not publicly disclosed, but based on participation in rounds ranging from $1.87M average at Seed to $4.7M at Series A, individual checks are estimated in the $100K–$500K range. The firm has made 26+ investments since launching in 2022, indicating a portfolio-construction approach prioritizing breadth at seed alongside reserve capital for follow-ons.
Lead Tendency
OpenSky takes both lead and follow positions depending on the deal. They co-led the $4.7M seed round for Siena AI alongside Sierra Ventures, demonstrating willingness to lead. In other deals such as Levanta, they participated as a follow investor. Their approach is opportunistic: they will lead when conviction is high and the right co-investors are aligned, but are equally comfortable in a supporting role to maximize deal access.
Recent Activity
Since founding in 2022, OpenSky has deployed capital into 26+ companies, making approximately 12 investments in a particularly active 7-month stretch. Their most notable documented recent deals include:
- Levanta (Dec 2023, Seed) — affiliate marketing for Amazon/Shopify, later raised $20M Series A from Volition Capital
- Siena AI (Nov 2023, $4.7M Seed) — AI autonomous customer service for e-commerce
- Daash Intelligence (Seed, then Series A 2025) — AI predictive commerce intelligence; raised $8.25M total
- Magic Mind (Seed/Series A) — nootropic performance shots; $29.97M raised in total
Portfolio Highlights
Some portfolio companies have shown strong progress:
- Levanta — raised a $20M Series A (Nov 2024) led by Volition Capital; platform connects brands with Amazon sellers and creator affiliates
- Siena AI — raised $4.7M seed; AI customer service agent used by major DTC brands
- Daash Intelligence — $8.25M raised across Seed and Series A; serves retail/e-commerce operators with predictive analytics
- Fishwife — notable premium seafood brand with strong DTC traction
The firm's GPs collectively report 80+ personal investments over a decade with 8x realized gains, providing deep pattern recognition in early-stage commerce companies.
Team
Josh Resnick, Co-Founder & General Partner — Serial entrepreneur with two major exits. Co-founded Pandemic Studios, a game studio sold to Electronic Arts for $860M. Subsequently co-founded Sugarfina, the luxury confections brand recognized by Fast Company as one of the World's 50 Most Innovative Companies. Previously spent 4 years at Activision as a producer and director. Holds a BA from Pomona College and MBA from The Wharton School at University of Pennsylvania.
Josh Payne, General Partner & Co-Founder — Founded and scaled StackCommerce (originally StackSocial), a commerce + content platform that grew to $100M+ in revenue before being acquired by TPG in 2020. Has made 30+ early-stage investments through OpenSky. Also served as Venture Partner at Amplify.LA. Brings deep expertise in marketplace dynamics, commerce media, and founder-to-exit journeys.
Brian MacMahon, Managing Partner — Additional managing partner supporting operations and portfolio.
Geographic Focus
OpenSky is US-focused with a base in Los Angeles, California. Their portfolio skews toward West Coast companies (California, Seattle) but they invest nationally across the United States.
Decision Process
With two co-founding GPs and a Managing Partner, OpenSky operates as a small partnership. Investment decisions are made collaboratively by the founding partners, likely with a relatively quick decision cycle given their seed-stage focus and operator backgrounds.
Founder Preferences
OpenSky explicitly seeks founders who are ambitious, passionate, smart, relentless, gritty, and disruptive. They strongly favor founders with prior operating or industry experience — particularly those building at the frontier of commerce. Their own backgrounds as founders give them a natural affinity for repeat founders and domain experts.