Kingsway

KWY on NYSE. Kingsway sells business services and extended warranty products to companies and consumers. Market value $270m.

Watch this stockFree. We tell you when something changes.

Price checks use the past 12 months to June 2026. Some use the latest annual report instead, as marked. Quality checks use five annual reports, the latest for the year to December 2025.

Cash flow or capital spending isn't reported, so free cash flow is unknown.

Should I look at this?

Not a fit for our list right now

See Financial services stocks that passed both tests

This is not advice. Check the numbers below.

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Return on equity
five annual reports to December 2025
28.0%five-year median

Yearly profit per dollar of owners' money: 28 cents. Above 10 is good.

Price to book
quarterly report to June 2026
21.6×

What you pay for each dollar of net assets: $21.56.

Earnings yield
past 12 months to June 2026
-2.2%

Profit per $100 you pay: $-2.21.

Quality score: 63 of 100. Price score: 0 of 100. Our list needs 70 on quality and 60 on price.

$9.56 a share, 14% above its 1-year low

Over the past year the price has ranged from $8.41 to $16.51.

Pays no dividend

Prices from Tuesday’s close (6 October).

Five years of cash, in billions

n/a
n/a
n/a
n/a
n/a
20212022202320242025
Revenue
$78m$93m$103m$109m$135m
Operating margin
n/an/an/an/an/a
Debt to equity
n/an/an/an/an/a
Shares outstanding
0.02bn0.03bn0.03bn0.03bn0.03bn

Health checks

  • Free cash flow positiveDoesn't apply to banks and insurers
  • Accounting checksDoesn't apply to banks and insurers
  • DebtDoesn't apply to banks and insurers
  • Revenue growth, five yearsStrong, 17.2% a year
  • Buying back its own sharesNo, 19% more shares since 2021

The quarter to June 2026

How the business did, compared with the same quarter a year earlier.

  • Sales: $39 million last quarter, up 28% on a year ago.
  • Profit: $157,000, after a loss of $4 million a year ago.
  • 5% more shares than a year ago. Each share owns a bit less of the company.
  • Sales grew on a year ago in each of the last 4 quarters.
Sales by quarter
Sales by quarter
Quarter toAmount
September 2024$27m
December 2024$30m
March 2025$28m
June 2025$31m
September 2025$37m
December 2025$39m
March 2026$39m
June 2026$39m
Profit by quarter
Profit by quarter
Quarter toAmount
September 2024-$3m
December 2024-$2m
March 2025-$3m
June 2025-$4m
September 2025-$3m
December 2025-$2m
March 2026-$3m
June 2026$157,000

From the company's quarterly reports to the SEC.

Dates

Next results (estimated)
n/a
Last annual report (10-K)
12 March 2026
Next quarterly (estimated, 10-Q)
5 November 2026

Who owns it

2 long-term investors we follow own it, unchanged from 2 last quarter. 73 funds in all.

Jun '25
Dec '25
Jun '26
Largest holders overall

From 13F filings for the quarter ended 30 June 2026.

Big holders and activists

7 investors own more than 5%.

  • at least 12.7%−6.1 pts
    (filed with 5 related holders)
    Since 17 December 2025
    What they said

    We are filing this Forty-Ninth Amendment to report that members of the Group have sold shares of Common Stock pursuant to the terms of the Option Agreements dated March 31, 2025, as amended each on December 17, 2025, by the Option Agreement Amendments. The Option Agreements and…

    Read the filing
  • Oakmont Capital Inc.
    at least 10.4%
    (filed with 1 related holder)
    Since 31 March 2025
    What they said

    Item 4 of this Schedule 13D is hereby supplemented as follows: On March 13, 2023, Oakmont converted the previously reported 13,142 Class A Preferred Shares into 82,144 Shares at a conversion price of US$4.00 per Share at the option of Oakmont. On March 22, 2023, Oakmont…

    Read the filing
  • Adam J. Patinkin
    at least 10.3%+1.3 pts
    (filed with 3 related holders)
    Since 18 May 2026
    What they said

    Mr. Patinkin was appointed as Chairman of the Board of Directors of the Company on March 11, 2026. On May 18, 2026, in connection with his appointment as Chairman, the Company granted to Mr. Patinkin a 10-year option to purchase up to 400,000 shares of Common Stock, which will…

    Read the filing
  • Oakmont Capital Inc.
    Passive investor
    at least 8.2%−2.1 pts
    (filed with 4 related holders)
    Since 17 December 2025
    What they said

    Item 4 of this Schedule 13D is hereby supplemented as follows: On December 17, 2025, the option agreement described in Item 6 of this Amendment No. 6 was exercised. Pursuant to such option agreement, Oakmont sold 500,000 Shares to DCP Special (as hereafter defined) at a price of…

    Read the filing
  • Greenhaven Road Capital
    Passive investor
    at least 6.8%
    (filed with 4 related holders)
    Since 30 October 2025
  • Charles Frischer
    Insider or founder
    6.8%
    Since 11 April 2025
  • Joshua S. Horowitz
    Passive investor
    at least 1.5%0.0 pts
    (filed with 3 related holders)
    Since 17 December 2025
    What they said

    On March 31, 2025, certain purchasers, including Palm Global and Mr. Horowitz, entered into option agreements with Stilwell Value LLC, an affiliate of Mr. Stilwell, to acquire an aggregate of 1,750,000 additional shares of Common Stock, at an exercise price of $8.25 per share,…

    Read the filing
  • Sold down below 5%
    Since 30 June 2026
  • Sold down below 5%
    Since 31 March 2026

From Schedule 13D and 13G filings: anyone owning more than 5% must file one.

What insiders did

In the last 12 months, 3 insiders bought $263,170 of shares on the open market. 3 sold $4m.

Cluster buy3 insiders bought within 30 days (31 August 2026 to 30 September 2026).
  • Horowitz Joshua
    Director
    Bought
    Date
    30 September 2026
    Shares
    858
    Price
    $9.23
    Value
    $7,919
  • Fitzgerald John Taylor Maloney
    President and CEO, Director
    Bought
    Date
    30 September 2026
    Shares
    269
    Price
    $9.30
    Value
    $2,502
  • Hansen Kent A
    CFO & EVP
    Bought
    Date
    30 September 2026
    Shares
    169
    Price
    $9.30
    Value
    $1,572
  • Horowitz Joshua
    Director
    Bought
    Date
    28 September 2026
    Shares
    2,717
    Price
    $9.28
    Value
    $25,202
  • Hansen Kent A
    CFO & EVP
    Bought
    Date
    15 September 2026
    Shares
    159
    Price
    $9.82
    Value
    $1,561
  • Fitzgerald John Taylor Maloney
    President and CEO, Director
    Bought
    Date
    15 September 2026
    Shares
    254
    Price
    $9.82
    Value
    $2,494
  • Hansen Kent A
    CFO & EVP
    Bought
    Date
    31 August 2026
    Shares
    149
    Price
    $10.45
    Value
    $1,557
  • Fitzgerald John Taylor Maloney
    President and CEO, Director
    Bought
    Date
    31 August 2026
    Shares
    239
    Price
    $10.45
    Value
    $2,498
  • Horowitz Joshua
    Director
    Bought
    Date
    20 August 2026
    Shares
    769
    Price
    $9.89
    Value
    $7,605
  • Horowitz Joshua
    Director
    Bought
    Date
    19 August 2026
    Shares
    7,034
    Price
    $9.84
    Value
    $69,203

From Form 4 filings: insiders must report trades in their own company's shares within two days.

Warning signs in its filings

Problems the company itself reported to the SEC, in its own words.

None of the warning signs we check for were found.

We look for five warning signs: doubt it can keep going, weak checks on its own accounts, a notice that its past accounts can't be relied on, a change of auditor, and one customer bringing in a big share of sales. We don't check lawsuits, investigations or debt yet.

We checked the auditor's report, internal controls, restatement notices, auditor changes and big customers in the 10-K filed 12 Mar 2026, plus the 10-Q filed 6 Aug 2026 and 6 later 8-Ks.

A 10-K is the yearly report every US company files with the SEC. An 8-K is a short notice of a big event.

What could go wrong

Cheap for a reason is the question the numbers cannot answer.

Whether the price already reflects the risks is what the deep dive is for.

The deep dive

Everything above is arithmetic on public filings. The deep dive reads the last ten years of annual reports, the proxy statements, and the earnings calls, then argues the case the way Buffett, Klarman, and Hohn would, and checks every claim against the source.

  • What the business is worth, as a range, and the margin of safety at today’s price
  • Prices to start buying, buy, and buy hard
  • The three things that would make this a mistake
  • Every number footnoted to the filing it came from
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Not advice. Numbers on this page come from SEC filings and are updated each night; prices are updated again after the US market closes. The five-year figures are rounded.