Long Way Ventures Research
Overview
Long Way Ventures (formerly Cascade Seed Fund) is an early-stage venture capital firm headquartered in Bend, Oregon. The firm officially rebranded from Cascade Seed Fund to Long Way Ventures on May 1, 2026, reflecting a strategic shift from a regionally-branded fund to a nationally-focused early-stage investor. Managing Partner Robert Pease launched the predecessor Cascade Seed Fund in 2019, building on more than a decade of angel investing experience dating back to 2011 through the Cascade Angels Funds.
Investment Thesis
Long Way Ventures backs great founders building category-defining technology companies at the earliest stages. The firm focuses specifically on founders tackling complex business problems in ways once considered too hard to scale. A key differentiator in their approach is a focus on solving difficult operational or technical challenges, particularly leveraging AI and modern software to unlock markets or business models that were previously impractical.
The firm's operating philosophy centers on four pillars: streamlined and efficient institutional due diligence, fair investments on standard terms, assistance when needed and stepping back when not required, and remaining calm in the face of market volatility. This founder-friendly, low-friction approach reflects a preference for being a value-added but non-intrusive partner.
Stage Focus
Long Way Ventures primarily invests at the pre-seed and seed stages, with a stated intent to be the first institutional money into companies. The firm has explicitly moved earlier than the "seed" label implied, as the industry has shifted seed definitions toward later-stage companies with larger rounds. They frequently participate in pre-seed rounds and provide foundational capital before companies have full product-market fit.
Check Size
The firm does not publicly disclose check size ranges. Based on fund size context (Cascade Seed Fund I closed at $10M, with subsequent funds growing the AUM), estimated typical checks are $250K–$2M for pre-seed and seed rounds. The firm has invested across more than 70 companies over three fund generations.
Geographic Focus
Long Way Ventures operates across more than 20 cities in the US and Canada. The portfolio is approximately 40% Pacific Northwest (anchored by Portland, Oregon and Seattle, Washington) and 60% from across the rest of the United States and Canada. This distribution reflects an intentional expansion beyond the Cascade region—the primary reason for the rebrand—as the firm recognized that the best founders tackling their thesis problems are not confined to the Pacific Northwest.
Sector Focus
Long Way Ventures is broadly sector-agnostic at the stage at which they invest, consistent with a pre-seed and seed mandate where category creation is part of the pitch. That said, the portfolio shows clear concentration in several areas:
- Fintech & Payments: Upward (fintech infrastructure), FlexPoint (payments automation for MSPs), Tab (commerce payments), Nectarine Credit, Safe Digit, FundMiner, Rock Paper Coin
- Enterprise Software & B2B SaaS: Talin AI (AI-powered HR/talent), Tiga AI (signal-based B2B sales prospecting), Platformr (CloudOps), Kickplan (pricing and packaging), Toolbelt (skilled trades workforce), Groopit (employee intelligence)
- Consumer Apps: A Kids Book About (children's media), Slumberkins (children's emotional learning), Rumpl (outdoor consumer goods), Sizzle (gaming/entertainment), Wildfang (fashion)
- Healthcare Digital: Enable Sleep (digital health, sleep), Kivo (healthcare technology systems), n2uitive (healthcare workflow)
- PropTech: Digs (homebuilder software), Roost
- Climate / Clean Energy: CarbonBright, Green T
- EdTech: ClassHero, Lumen Learning
The firm is increasingly investing in AI-enabled companies that use the technology to tackle previously unscalable business models.
Recent Activity
Long Way Ventures has been actively deploying from its current fund (Long Way Ventures Fund I, previously Cascade Seed Fund III):
- December 2025: Invested in Kivo (healthcare technology systems)
- November 2025: Participated in Upward's (formerly Upwardli) $8M Series Seed+ round, co-led by Dundee Venture Capital and Breakwater Ventures, with Techstars and others
- November 2025: Joined Oregon Venture Fund, Portland Seed Fund, Flying Fish, and SPLY Capital in a $5M pre-Series A for Digs, proptech for homebuilders
- March 2025: Invested in Tiga AI's $2M growth round alongside Bull City Venture Partners and Virginia Venture Partners
- March 2024: Participated in FlexPoint's $35M debt-and-equity round (as follow-on from Cascade Seed Fund II)
The fund has maintained active deal velocity with 3+ new investments per year in recent periods.
Portfolio Highlights
Notable portfolio companies include:
- Upward (formerly Upwardli): Fintech infrastructure with $8M Seed+ raised and Mastercard partnership
- FlexPoint: Payments automation for MSPs, raised $35M in 2024
- A Kids Book About: Children's publishing brand with broad distribution
- Slumberkins: Children's emotional learning brand, received national attention
- Rumpl: Consumer outdoor brand (blankets/apparel)
- Digs: Homebuilder software startup, $5M pre-Series A 2025
Exits include: Hubly (acquisition), Sync Floor (acquisition), DryPowder, Talkoot, DeepSurface, LegUp, Solace, Zipcan, Edj Sports, and multiple Cascade Angels companies.
Team
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Robert Pease, Managing Partner: Over 25 years of experience as a software executive, founder, and investor. Led 70+ investments since 2011. Previously member of the executive team and product lead across six venture-backed startups. Began career at Accenture's Global Communications and Technology practice. Deep operational background before transitioning to investing.
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Milena Morris, Venture Partner: Brings investment experience and startup operations expertise. Previously Venture Partner at Cascade Seed Fund. LinkedIn: linkedin.com/in/milenamorris.
Decision Process
With Robert Pease as Managing Partner and Milena Morris as Venture Partner, Long Way Ventures operates with a lean team. Investment decisions are likely made on a partnership basis between the two, with Pease as the primary decision-maker given his role. The firm emphasizes efficiency in diligence, suggesting a streamlined decision process.
Founder Preferences
Long Way Ventures has a stated preference for repeat founders and those with deep domain expertise in the problems they are solving. They are particularly interested in founders using AI to unlock scale in industries where operational complexity was previously a barrier. The firm values coachability and seeks partnerships where their operational experience adds value.
Historical Context
The firm evolved through several phases: Cascade Angels Funds (angel-stage investing starting 2011), Cascade Seed Fund I ($10M, 2019), Cascade Seed Fund II, and now Long Way Ventures Fund I. The rebrand was prompted by the fund's national expansion and the evolution of industry terminology around "seed" investing toward later stages.