(in thousands)

Three months ended September 30,

Nine months ended September 30,

2023

2022

2023

2022

Segment operating income:

Extended Warranty

$

1,778

$

2,461

$

4,602

$

7,120

Kingsway Search Xcelerator

1,003

723

4,196

2,422

Total segment operating income

2,781

3,184

8,798

9,542

Net investment income

351

463

1,419

1,547

Net realized gains

206

797

539

1,035

Net gain (loss) on equity investments

592

(5

)

3,374

(53

)

Gain on change in fair value of limited liability investments, at fair value

320

195

194

368

Net change in unrealized gain on private company investments

63

—

63

—

Gain on change in fair value of real estate investments

—

1,488

—

1,488

Impairment losses

(71

)

—

(166

)

—

Gain (loss) on change in fair value of derivative asset option contracts

—

13,498

(1,366

)

13,498

Interest expense

(1,061

)

(2,139

)

(5,119

)

(5,207

)

Other revenue and expenses not allocated to segments, net

(2,833

)

(7,242

)

(9,279

)

(13,488

)

Amortization of intangible assets

(1,424

)

(1,358

)

(4,252

)

(4,242

)

Loss on change in fair value of debt

(165

)

(1,794

)

(195

)

(4,992

)

Gain on disposal of subsidiary

342

37,917

342

37,917

Gain on extinguishment of debt

—

31,616

—

(Loss) income from continuing operations before income tax (benefit) expense

(899

)

45,004

25,968

37,413

Income tax (benefit) expense

(102

)

6,061

810

5,620

(Loss) income from continuing operations

$

(797

)

$

38,943

$

25,158

$

31,793