Isaacman Jared

10% Owner Isaacman buys 388,500 shares ($15.9M) across 2 transactions at FOUR, raising stake to 1.79M shares

Isaacman, a 10% owner of Shift4 Payments, executed 2 separate purchases totaling 388,500 shares for $15,943,101.70 at a blended average price of $41.04 on May 11-12, 2026, expanding his holdings by 27.8% to 1,787,455 shares. This represents a material accumulation by a significant shareholder at a time when FOUR trades at $40.87, down 61.7% from its 52-week high of $106.81 and declining 10.1% over the prior 30 days. His prior 5 trades at this ticker have yielded mixed timing outcomes—only 1 of his prior FOUR purchases has yet shown a measurable 90-day return (down 20.9%), while his cross-ticker track record shows 66.67% 90-day win rate—suggesting varied execution at this specific holding. The company remains fundamentally sound, with $1.1B in quarterly revenue, 25.5% annual revenue growth, and a 27.61 P/E ratio, though the sharp recent decline from peak valuation warrants attention to what may be driving the pullback.

Isaacman (10% owner) bought 43.8K shares of Shift4 Payments at $45.75, accumulating to 1.41M shares amid 55.8% decline from 52-week high.

Isaacman, a 10% owner, purchased 43,827 shares at $45.75 on 2026-03-10, bringing total holdings to 1.41M shares—a 3.2% increase from pre-transaction levels. The purchase occurs in a difficult market environment: the stock trades at $47.23, down 55.8% from its 52-week high of $106.81 and down 19.4% over the past 30 days. At the same ticker, Isaacman's prior buy on 2025-08-11 achieved a 30-day return of +2.4% but a 90-day return of -20.9%; his 2025-08-08 purchase showed +6.9% at 30 days but -18.4% at 90 days—neither trade was well-timed on the 90-day metric. Three more recent purchases (2026-02-26, 2026-02-27, and 2026-03-02) have no measurable outcomes yet. The company itself shows solid fundamentals with $1.2B in quarterly revenue, +25.5% annual growth, and a P/E of 45.41, though the market cap of $3.8B suggests investors have priced in significant headwinds. This filing marks a continuation of near-daily accumulation at depressed price levels, but the lack of well-timed outcomes in his same-ticker history indicates prior purchases at similar points have not produced near-term gains.

10% owner Jared Isaacman buys 45,693 shares at $43.83; stock down 55.6% from 52-week high and 31.6% in 90 days.

Jared Isaacman, holding 1.37M shares (1,366,900 shares post-transaction), purchased 45,693 shares at $43.83 on 2026-03-02 for $2.0M in an open-market transaction. This buy occurs as FOUR trades at $47.46, down 55.6% from its 52-week high of $106.81 and down 31.6% over the prior 90 days, signaling a material pullback in the stock. Isaacman's same-ticker history shows mixed outcomes: of 5 prior trades at FOUR (including two recent buys on 2026-02-27 and 2026-02-26 whose results are not yet measurable), only 1 of 3 measurable buys achieved a positive 90-day return, suggesting limited success timing reversals at this ticker. His cross-ticker track record shows a 66.67% 90-day win rate with an average 90-day return of 3.4%, indicating moderate but not exceptional timing precision across his broader portfolio. The acquisition occurs amid solid fundamentals—$1.2B quarterly revenue with 25.5% annual growth and a 45.63 P/E—but the stock's recent sharp decline and his mixed historical accuracy at this specific ticker present competing signals that warrant monitoring.

10% owner Jared Isaacman buys 296,237 shares for $13,658,260.21 across 2 Feb 26–27 transactions at FOUR (blended $46.11)

Isaacman, a 10% shareholder, executed 2 separate purchases totaling 296,237 shares for $13,658,260.21, increasing his holdings by 28.9% from 1,024,970 to 1,321,207 shares. The blended average purchase price of $46.11 sits 1.8% below the current price of $46.94, but notably the stock is -56.0% from its 52-week high and down -20.5% over the past 30 days. At the same ticker FOUR, Isaacman's prior 4 measurable buys show mixed outcomes: 2 of 4 yielded positive 90-day returns (2024-06-14 at +15.8%, 2024-06-06 at +11.7%), while 2 showed declines (2025-08-11 at -20.9%, 2025-08-08 at -18.4%). His cross-ticker buy history averages +5.7% at 30 days and +3.4% at 90 days with a 66.67% win rate, though this provides limited bearing on FOUR-specific outcomes. The magnitude of this $13.7M stake increase and the recent steep price decline form the salient context for investor attention.

Isaacman purchases 196,426 shares ($16.3M) in two tranches, raising stake to 939,715 shares (+26.4%)

Isaacman, Executive Chairman of Shift4 Payments, executed 2 separate purchases totaling 196,426 shares for $16,266,182.03 at blended average price $82.81 on August 8–11, 2025. The purchase increased his holdings by 26.4% from 743,289 to 939,715 shares. His prior trades at FOUR show a strong pattern: 4 of 4 prior buys (May–June 2024) generated positive 90-day returns (+8.8% to +23.2%), indicating well-timed entry points. The company's fundamentals are solid—$966.2M quarterly revenue with +29.9% annual growth and $34.0M net income—though the stock is currently -34.0% from its 52-week high and down -17.8% over the past 30 days. This large, multi-transaction insider accumulation into recent weakness, combined with the insider's consistent 90-day timing success at this ticker, merit investor attention.

Shift4 CEO Isaacman buys 14,486 shares for $1.0M; stock down 18.8% from 52-week high; $5.8B company growing revenue +28.6%

Isaacman, Chairman & CEO of Shift4 Payments, purchased 14,486 shares at $69.40 on 2024-06-14, expanding his holdings to 666,117 shares (+2.2%). The purchase occurs within a context of recent weakness: the stock has declined 18.8% from its 52-week high of $85.90 and is down 10.0% over the prior 90 days. This buy is the third consecutive open-market purchase by Isaacman at Shift4 within a 22-day window (purchases on 2024-05-14, 2024-05-23, and 2024-06-06 preceded this transaction). While Isaacman's cross-ticker buying track record shows an average 30-day return of +6.8% across 3 prior buys, his prior trades at Shift4 have not yet demonstrated a 90-day success pattern—the only measurable 90-day outcome from prior trades at this ticker is from the 2024-05-14 buy, which showed a +6.8% 90-day return. The company itself reports strong fundamentals: $707.4M in latest-quarter revenue, +28.6% annual growth, and a P/E of 62.81 on a $5.8B market cap. The pattern of repeated purchases during a period of stock weakness, combined with Shift4's solid growth trajectory, warrants monitoring for signals about management's near-term conviction, though the high valuation multiples suggest elevated near-term price risk regardless of insider sentiment.