Diligence memo · auto-generated · as of July 2, 2026
Kingsway Financial Services Inc
Kingsway Financial Services Inc looks fair against its niche peers and is quiet on financing cadence.
Businessfiled
Kingsway Financial Services Inc operates in Business Services, based in CHICAGO.
No verified homepage on file yet — operating evidence is limited to the public record.
Capital & rounds (filed)filed
Kingsway Financial Services Inc has raised $6.0M in disclosed capital across 1 recorded round, aggregated from public filings. Its latest round is modeled as Series A (a $4.0M–$15M round).
Largest single filing: $6.0M on 2025-02-12.
Most recent recorded round closed around 2025-02-12.
Valuation (modeled)modeled
Provath models Kingsway Financial Services Inc at approximately $25M (range $8.3M–$46M). This is an algorithmic estimate from round sizes and same-niche peers — not a quoted or reported figure.
Read: Fair. Modeled value is 1.29× the median modeled value of Series A Business Services companies in 2025–2027 (57 peers) — value vs value, same stage and era. Within the normal band (129% of peer median) for its niche.
Financing rhythm & timingmixed
Last raise 17 mo ago; this sector typically re-raises about every 12 months.
Slightly overdue versus sector cadence.
Comparablesmixed
Capital scale ranks ahead of 80% of Business Services peers (2439 compared).
Modeled value ranks above 68% of those peers.
Closest niche peers: Brickell Bay Holding Company, LLC, Housr Holdings 1 LLC, CPE Enterprises, LLC, Panda Group, LLC, Hague Global Holdings, Inc..
Peoplefiled
2 named people on file across officers, directors and signatories.
Risks & flagsmixed
No clearly named CEO/founder/principal in the surfaced records — key-person evidence is thin.