Jim Stallings

General Partner, PS27 Ventures
Jim Stallings makes leadership 90% of his investment decision—preferring strong leaders with flawed plans—asks how much of the product is AI-built, and is known for Bentley, the talking dog mascot.
How to contact Jim Stallings
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Avg Check
$250K–$1M
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Does their fund Lead?
No
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Jim Stallings
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Sectors their fund invests in
SaaS
Fintech
Health
Ecommerce
Climate
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$250K–$1M
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No
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About Jim Stallings

Jim Stallings named his fund PS27 after Psalm 27, a passage he and fellow Marines used to read before dangerous missions, and he judges founders mainly by their leadership, saying it makes up 90% of his investment decision and that he’d rather back a strong leader with a flawed plan than a weak leader with a polished one. He now asks founders how much of their product is being built by AI, hopes to help turn Jacksonville into a major tech hub after choosing to return there following his time at IBM, and is known around PS27 for Bentley, the talking dog who serves as the firm’s mascot.

About their Fund

PS27 Ventures

Sectors
SaaS, Fintech, Health, Ecommerce, Climate
Rounds
Avg Check Size
$250K–$1M

PS27 Ventures was started by Jim Stallings after his 25+ year IBM career, and it invests in enterprise and financial services companies building "sticky plumbing software" like payments, compliance, and security systems, usually only after they already have paying customers. The fund backs this with a network it calls the "Ring of Fire" connecting founders to customers, partners, and investors, and it operates under the philosophy of "either disrupt or be disrupted."

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