Josh Diamond

General Partner, Walkabout Ventures
Josh Diamond is a seed-stage fintech investor with hands-on financial services experience and a UCLA J.D., giving him uncommon regulatory expertise for early-stage fintech founders.
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Stages their fund invests in
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Sectors their fund invests in
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Avg Check
$50K - $500K
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Does their fund Lead?
Yes
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Geos their fund invests in
USA
Josh Diamond
Stages their fund invests in
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Sectors their fund invests in
Fintech
SaaS
Insurtech
HR Tech
Enterprise
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$50K - $500K
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Leads?
Yes
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About Josh Diamond

Josh Diamond founded Walkabout Ventures in 2019 as a seed-stage fund focused specifically on financial services and fintech companies, bringing prior hands-on industry experience rather than just investment background. He holds a J.D. from UCLA School of Law, which is uncommon among seed-stage fintech investors and helps him navigate the regulatory complexities of financial services startups.

About their Fund

Walkabout Ventures

Sectors
Fintech, SaaS, Insurtech, HR Tech, Enterprise
Rounds
Seed - Series A
Avg Check Size
$50K - $500K

Walkabout Ventures is a seed fund founded specifically to fill an underfunded gap in very-early-stage financial services and fintech in the U.S., focusing on technical "picks-and-shovels" businesses that modernize the infrastructure and back-office operations of financial and insurance services rather than consumer-facing fintech. Despite being a small, sector-focused fund, Walkabout consistently leads significant rounds and has become a signal investor whose early validation helps attract later-stage institutional capital from marquee fintech investors.

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