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Insider Cluster (2 insiders) ·Filed Oct 16, 2026

HIPO

Hippo Holdings Inc.
NEUTRAL
Impact 3/10
Horizonweeks Processed10d 17h ago
Insider cluster: 2 insiders, $212K total
Actionable Insight • Neutral

Monitor next 10-Q for any deterioration in underwriting metrics or cash flow to assess if these sales were liquidity-driven. The CEO's sale is modest and does not warrant immediate concern.

DirectionNeutral
Confidencemedium
Horizonweeks
Latest settled — T+5d
HIPO ▲ +8.59% at T+5d
NEUTRAL call +8.59% · α vs SPY +8.74% · entry $35.50 → $38.55
Next anchor: T+20d in 17d
Entry = T+0 close
Oct 16, 2026
via day close
T+1d
+5.15%
call +5.15% · α +4.82%
$37.33
settled 8d ago
T+5d
+8.59%
call +8.59% · α +8.74%
$38.55
settled 4d ago
T+20d
Pending
in 17d
T+60d
Pending
in 3mo

Price Chart

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Executive Summary

Two Hippo Holdings insiders, including CEO Richard McCathron, sold a combined $212K in open-market sales over a one-week window. The CEO's $171K sale is the largest, but the total is modest relative to the company's market cap, suggesting routine portfolio diversification rather than a negative signal.

Key Financial Metrics

Direction
selling
Total Value
$212.0K
Insiders
2

Key Facts

  • CEO Richard McCathron sold 5,000 shares for $171K on 2026-10-09 at $34.18.
  • CEO of Spinnaker Torben Ostergaard sold 1,200 shares for $41K on 2026-10-15 at $35.03.
  • Total cluster value is $212K, representing approximately 0.07% of market cap (market cap not provided).
  • Both sales are open-market sales (code S) with no 10b5-1 plan indication in the data.
  • No insider buying activity in the cluster.

Financial Impact

$212K in insider sales, approximately 0.07% of market cap (market cap not provided).

Risk Factors

  • CEO selling could be misinterpreted by the market as a negative signal.
  • No insider buying to offset the selling cluster.

Investment Themes

Traditional Finance

Documents Analyzed

This report is based on 1 SEC document filed with EDGAR.

DocumentAccession Number
CLUSTER Data (Synthetic)cluster-HIPO-1792182339092
9 reports for HIPO
Performance horizon

Track record builds as more directional reports settle.

Filters
Rows
Reports for HIPO — sortable, filterable
TypeNow
Oct 16, 2026
10d ago
Insider Cluster
NEUTRAL ★ 3/10
$35.50awaiting T+20—$38.02 (+7.10%)
Oct 14, 2026
13d ago
Press Release
NEUTRAL ★ 1/10
$34.39awaiting T+20—$38.02 (+10.56%)
Oct 9, 2026
17d ago
144
NEUTRAL ★ 3/10
$33.97awaiting T+20—$38.02 (+11.92%)
Aug 27, 2026
8w ago
Press Release
BULLISH ★ 7/10
$32.61 $30.24▼ −7.27%▼ −6.76%$38.02 (+16.59%)
Aug 18, 2026
9w ago
Insider Cluster
NEUTRAL ★ 2/10
$32.64 $32.00▼ −1.96%▼ −0.01%$38.02 (+16.48%)
Aug 10, 2026
11w ago
144
NEUTRAL ★ 2/10
$32.43 $32.12▼ −0.96%▲ +0.10%$38.02 (+17.24%)
Jun 15, 2026
19w ago
8-K
NEUTRAL ★ 2/10
$25.86 $28.52▲ +10.29%▲ +10.09%$38.02 (+47.02%)
May 19, 2026
22w ago
Insider Cluster
NEUTRAL ★ 3/10
$25.99 $25.96▼ −0.12%▼ −0.86%$38.02 (+46.29%)
Feb 24, 2026
34w ago
8-K
BULLISH ★ 7/10
$27.44 $25.86▼ −5.76%▼ −0.52%$38.02 (+38.56%)
Showing 9 of 9

US Market Status

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Report published Oct 16, 2026