Live Oak Says it Made $28 Million Gain on Payrailz Exit

Live Oak Ventures, a wholly owned subsidiary of Live Oak Bancshares (NASDAQ: LOB), is reporting that it made a $28 million gain on its exit of Payrailz which wsa purchased by Jack Henry & Associates – a banking tech provider. Payrailz is a digital payments platform. The exit is subject to closing adjustments so the amount may vary slightly once completed.

Stephanie Mann, Live Oak’s Chief Strategy Officer, commented:

“This is the third investment by Live Oak that has had a greater than 9x return. We are proud of the success we are seeing in our investment strategy – partnering with industry veterans to address challenges in banking, and particularly in small business banking. Fran Duggan and Paul Franko, Payrailz founders, have modernized payment solutions for banking and we look forward to continuing on our product roadmap as they join Jack Henry.”

Live Oak Ventures reports that it realized a $121 million gain when exited Finxact earlier this year, as well as $61 million in cash and noncash gains in Greenlight Financial Technology since Live Oak’s first investment in 2018.

Live Oak currently holds investments in 11 portfolio companies with a total estimated implied market value of approximately $150 million, excluding Payrailz, as of June 30, 2022.



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Disclosure Quest

Reg A - Form 1-A Filings Beta

Beta. Initial Form 1-A only. Target raise is the stated Amount to be Raised, totaled. Compared with the same dates one year earlier.

YTD: Jan 1, 2026 - Nov 4, 2026 vs Jan 1, 2025 - Nov 4, 2025

Share this graph
Number of Filings134Prior 129 +3.9%
Target Raise, Total$3.45BPrior $3.59B -3.8%
This YTDYear priorChange
Filings 134 129 +3.9%
Target raise $3.45B $3.59B -3.8%

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Source: DisclosureQuest. Initial Form 1-A only.

Created by Crowded Media Group

This display counts initial Form 1-A filings only. It does not represent subsequent filings, including Form 1-A/A amendments or Form 1-A POS post-qualification updates filed by the issuer. Amounts are the stated Amount to be Raised on the initial filing, not capital raised and not amounts revised in later filings.

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