Walkabout Ventures
3632 Redwood Avenue, Los Angeles, CA, 90066, United States
Overview
Walkabout Ventures is an investment fund focused on venture funds investing in financial service startups. The firm prefers to invest in the financial services and information technology sectors. It was founded in 2019 and is based in Los Angeles, California, United States.
- Total investments
- 17
- Lead investments
- 8
- Investments · 12mo
- 4
- Active investors
- 1
Sector focus
- Finance
- Financial Services
- FinTech
- Venture Capital
Investment portfolio
- Astraeus
Participated · Equity · Aug 2026
Astraeus provides an AI-native infrastructure platform for wealth management firms that centralizes client, account, product, compliance and operational data and codifies business rules and governance. At the center of the platform is a semantic layer and ontology that models relationships among clients, advisors, accounts, products, fees, policies and regulatory requirements, and the system records changes to create an audit trail for explainability. The platform is model-agnostic, allowing firms to use different AI models without tying their data and governance to a single provider. Astraeus targets RIAs, broker-dealers, private banks, multifamily offices, wealth technology platforms, private equity firms and consulting organizations for use cases including client intelligence, advisor workflows, compliance, investment research, portfolio operations and AI-agent orchestration. The company was founded by Phill Rosen and Jon Stevenson, who previously worked together at MoneyLion, and is based in New York. Astraeus has raised more than $10 million to date from investors including Fintech Collective, F-Prime, Walkabout Ventures and Plug and Play Ventures, and launched its platform after that fundraising.
- Discern
Led · Series A · Jul 2026
Discern provides an automated legal entity management system of record that digitizes U.S. government filings across jurisdictions. Its platform offers automated annual report filings, Secretary of State services, entity payment processing, and digital Service of Process (SOP) delivery. The company serves more than 800 clients across technology, finance, and healthcare, including Vestwell, Accolade Partners, and IA Ventures. Led by CEO Raj Patel and based in Dover, DE, Discern plans to use its Series A proceeds to expand operations and engineering teams and to build new features for its Registered Agent service. Financially, the company has raised $10M in this Series A, bringing total funding to $17.5M.
- Barker
Led · Equity · Nov 2025
Barker offers an agentic valuation system that delivers real-time, warranty-backed prices for hard-to-value collateral such as private jets, art, industrial equipment, and GPUs. Each valuation is insured through Munich Re’s aiSure performance guarantee, so if an asset ultimately sells below the AI-derived price the insurance covers the shortfall, turning subjective appraisals into enforceable financial instruments. Since partnering with Munich Re in Q1 2025, the platform has processed about $2 billion in asset valuations and gained approval from several bulge-bracket banks and private lenders (kept confidential). This insurance layer is designed to unlock greater credit availability by giving lenders confidence in collateral values. The company plans to channel new capital into expanding coverage to additional asset classes and deepening relationships with key market participants. Headquartered in New York, Barker positions itself as the “trust layer” for asset-based finance. Financial details beyond funds raised have not been disclosed.
- Advisor.com
Led · Seed · Sep 2025
Advisor.com operates an online marketplace where proprietary AI-powered matching technology pairs investors with fiduciary financial advisors aligned to their goals and preferences. The platform rigorously screens advisors on regulatory history, assets under management, client ratios, and third-party reviews, and already counts Creative Planning, Edelman Financial Engines, Empower, Pure Financial, United Capital, and Vanguard among its network. Advisor.com primarily targets the large segment of professionals with less than $500,000 in investable assets who are underserved by traditional advisory channels. Beyond the marketplace, the company runs Advisor Wealth Management (AWM), a rapidly growing registered investment adviser that blends automated insights with human guidance. Founder Hunter Stunzi previously built and sold online lending marketplace SnapCap to LendingTree in 2017. Headquartered in Charleston, S.C., the firm aims to scale both customer acquisition and advisor enrollment while continuously enhancing its AI capabilities with the new capital.
- OLarry
Participated · Series A · Aug 2025
OLarry is an AI-powered tax advisory firm that provides flat-fee, year‑round personalized tax planning to high-net-worth individuals, businesses, trusts, and estates. The company automates client onboarding, document preparation, and data extraction with proprietary AI to enable CPAs to focus on proactive tax strategy. Since its 2024 inception, OLarry has pursued a roll-up strategy, having acquired Branton, de Jong & Associates and Byrne, Seligman & Co., and now serves more than 2,000 clients and 700+ businesses across the United States. OLarry is developing tax data classification and extraction models, predictive scenario-planning tools, and an agentic AI client experience to streamline complex financial data ingestion and real-time tax optimization. The company cites market tailwinds including a 17% decline in accountants entering the job market and projected retirements of 75% of partner-level CPAs within 10–15 years. OLarry is pursuing further CPA firm acquisitions and recruiting top-tier CPAs to scale its advisory practice.
Team
Josh Diamond
General Partner
LinkedIn