Walkabout Ventures

Walkabout Ventures Research Investment Thesis Walkabout Ventures is a specialized seed-stage venture capital fund focused exclusively on financial services and fintech startups. Founded in 2019 by Josh Diamond and Jordy Albert, the firm was created to fill an underfunded gap in very-early-stage financial services investment in the United States. The firm believes that the best opportunities exist in technical "picks-and-shovels" businesses that modernize the infrastructure and back-office operations of financial and insurance services, rather than consumer-facing fintech. Walkabout's investment thesis centers on supporting technical founders building modernized financial infrastructure, with a particular focus on: Back-office fintech solutions for financial and insurance firms Payment processing and settlement infrastructure Retirement and wealth management technology Insurance technology (InsurTech) Financial data infrastructure and APIs Compliance and regulatory technology Sector Focus Walkabout focuses exclusively on the fintech and financial services sector , with particular emphasis on: B2B Financial Services SaaS - Solutions for banks, credit unions, and financial institutions InsurTech - Technology modernizing insurance operations Payments & Settlement - Payment processing, clearing, and settlement infrastructure Wealth & Retirement Tech - Tools for retirement planning and wealth management Financial Data Infrastructure - APIs, data platforms, and infrastructure for financial services Stage Focus Walkabout primarily invests in pre-seed and seed rounds: Pre-Seed : $250K-$500K for early-stage teams with MVP Seed : $100K-$500K for companies with product-market traction Selective Series A follow-ons : Occasionally participates in Series A rounds for promising portfolio companies The firm explicitly positions itself as a lead investor and has demonstrated strong ability to anchor rounds, attracting follow-on institutional capital from larger fintech VCs. Check Size and Fund Details Check Size Range : $100K-$500K Pre-seed typical: $250K-$500K Seed typical: $100K-$500K Can write up to $500K in select cases AUM : Approximately $193 million across multiple funds Fund I (raised ~$10M in 2019) Multiple subsequent SPVs and fund vehicles Actively deploying capital Lead Tendency : Frequently leads rounds; has become a signal investor whose early validation helps attract marquee institutional fintech investors Recent Activity & Portfolio Walkabout has maintained consistent deal flow with 27 total investments and 3 new investments in the last 12 months as of November 2025. Recent Lead Investments: Advisor.com (October 2025): Led $9M seed round for financial advisor platform Barker (November 2025): Led $3.5M seed round for AI valuation platform for illiquid assets Functional Finance (September 2024): Led $20M Series A for premium payments infrastructure (portfolio follow-on) Notable Portfolio Companies: Functional Finance - Premium payment processing for financial services (led Series A) Lithic - Payment infrastructure APIs Clair - Consumer credit and lending platform Capitalize - Retirement account rollover platform (Series A: $12.5M with Canapi Ventures) Retirable - Retirement savings platform ($4.7M seed) HM Bradley - Banking and financial services platform Sensible Weather - Insurance-related financial services Odie Pet Insurance - Pet insurance fintech Themis - Business/productivity software for financial services Co-Investment Partners: Walkabout frequently invests alongside: New Enterprise Associates (NEA) Altai Ventures Canapi Ventures Bling Capital Greycroft RRE Ventures Munich Re Ventures Marin Sonoma Impact Ventures TTV Capital Team Founders & GPs: Josh Diamond - Founder & General Partner Education: UCLA School of Law Background: Early fintech investor and operator Focus: Fintech thesis development and deal sourcing Location: Los Angeles, California Email: [email protected] Jordy Albert - Co-Founder & General Partner Background: Operations experience in fintech; co-founded Measured Expertise: Operational support for early-stage founders, fintech operations Currently: Splits time between Walkabout and Measured (CEO) Location: Phoenix, Arizona The partnership brings complementary skills: Diamond's investment thesis and deal sourcing combined with Albert's operational expertise and founder empathy. Geographic Focus Primarily US-focused : Strong Los Angeles presence (home base) Active in major fintech hubs: New York, San Francisco Bay Area, Austin Selective investments in other US markets Investment Process & Philosophy Decision Process : Partnership-based (both co-founders actively involved in due diligence and decisions) Decision Timeline : Relatively fast for seed-stage (typically 2-4 weeks from first meeting to term sheet for strong candidates) Warm Intros : Preferred but not required; will respond to strong inbound pitches Board Involvement : Typically takes observer seat or light board involvement; focuses on operational support rather than governance Involvement Level : Hands-on operational support; Albert frequently advises on scaling operations and go-to-market Founder Preferences Walkabout seeks: Technical founders with deep fintech domain expertise Repeat founders or operators from scale-up companies Mission-driven teams solving real pain points in financial services Scrappy operators who can move fast with limited capital Teams that value operational support and mentorship Co-Investment Strategy Walkabout frequently co-invests with larger institutional fintech VCs, demonstrating strong ability to: Anchor rounds and establish valuation Attract follow-on institutional capital Bridge from pre-seed to seed-level institutional investors The firm has become a "signal investor" in fintech - their investment indicates strong early validation. Notable Exits & Achievements While specific exit data is limited, the firm's portfolio includes: Multiple companies that have raised Series A and beyond Strong track record with companies in payments, insurance, and wealth tech sectors Early investor in companies that have achieved significant scale Strengths & Reputation Sector Specialization : Deep focus on fintech/financial services (vs. generalist approach) Lead Capability : Demonstrated ability to lead rounds and anchor valuations Signal Value : Portfolio companies use Walkabout's investment as validation Operational Support : Albert's background provides founder support beyond capital Founder-Friendly : Reputation for fast decisions and flexible terms Strategic Co-Investors : Strong relationships with institutional fintech VCs (NEA, etc.) Decision Factors & Rejection Criteria What They DON'T Fund : Consumer-facing fintech without institutional B2B angle Non-fintech sectors Companies not addressing real financial services pain points Teams lacking domain expertise in finance What They DO Fund : B2B financial services infrastructure Technical solutions to financial services problems Companies with regulatory clarity Founders with financial services background Fund Status Current Status : Actively deploying capital from existing funds Recent Activity : 3 new investments in last 12 months (as of November 2025) Latest Investment : Barker, November 2025 The firm appears to be in steady-state deployment mode with consistent deal flow in their core fintech focus area.