13F Insight

LendingTree Founder Douglas Lebda Holds Just 7,500 Shares While TREE Sits Near Multi-Year Lows

Alex Rivera

Douglas Lebda, who founded LendingTree and sold $272.8M in career insider transactions, now holds only 7,500 directly-held shares worth roughly $257K as TREE trades near $34 — a fraction of the $70+ levels where his RSUs vested months earlier.

Douglas Lebda, who co-founded LendingTree (TREE) more than two decades ago, now directly holds just 7,500 shares of the company he built — worth roughly $257,000 at recent prices near $34. That is the residual position after a series of RSU vestings and mandatory tax withholdings steadily whittled his directly-held stake through 2025.

Lebda’s career Form 4 record spans 1,059 transactions totaling $272.8 million in sales and $8.7 million in purchases. But his most recent activity tells a different story than the headline numbers suggest: no open-market sales in at least a year. Instead, the filings show a pattern of restricted stock awards, vestings, and tax-related dispositions that reduced his share count from over 134,000 in March 2025 to 7,500 by September 2025.

What Happened: RSU Vesting and Tax Withholding

In March 2025, Lebda received three large equity awards: 70,000 shares, 60,000 shares, and 3,500 shares of TREE common stock. These grants — totaling 133,500 shares — were part of his compensation as chairman of the board.

As those awards vested in tranches through 2025, LendingTree withheld shares to cover Lebda’s tax obligations (reported as F-code transactions on Form 4). Here is how the vesting and withholding played out:

DateEventShares VestedTax WithheldShares After
Mar 1, 2025RSU vest (3 tranches)12,6653,704134,525
Mar 2, 2025RSU vest (2 tranches)2,0994625,902
Apr 23, 2025RSU vest332485,856
May 16, 2025RSU vest (2 tranches)15,0003,270138,660
Sep 24, 2025RSU vest (2 tranches)15,0003,27045,204
Sep 30, 2025RSU vest (2 tranches)15,0003,1287,500

Each vesting event triggered a mandatory tax withholding that consumed 30–45% of the shares. By the final vesting in September 2025, Lebda was left with exactly 7,500 directly-held shares — approximately one RSU tranche’s worth.

The CEO Transition

Lebda stepped back from the CEO role in 2022, handing day-to-day leadership to Scott Peyree. He remains chairman and is listed as a 10% beneficial owner in SEC filings, though Form 4 directly-held shares show only 7,500. The gap between “10% owner” status and the minimal direct holdings likely reflects shares held via trusts, LLCs, or other indirect vehicles not detailed in the most recent Form 4 filings.

LendingTree’s Record Quarter at $34

The timing adds context. LendingTree reported record Q4 2025 revenue of $319.7 million, up 22% year-over-year. Insurance segment revenue hit $214.6 million (+25%). The company posted GAAP net income of $144.7 million, though $146.4 million of that was a one-time tax benefit from releasing a valuation allowance against deferred tax assets.

Adjusted EBITDA was $36.7 million (+14% YoY), and management guided for full-year 2026 revenue of $1.275–$1.33 billion. Despite the improving fundamentals, TREE stock has dropped roughly 50% from the $65–$70 range where Lebda’s RSUs vested in September 2025 to approximately $34 today.

Other insiders have been active too. COO Ian Malcolm Smith sold 10,000 shares in January 2026 at $54.16. Multiple directors purchased 5,000-share blocks in June 2025 at $36.52 — prices near the current level.

Career Transaction Profile

MetricValue
Total Transactions1,059
Career Sell Value$272.8M
Career Buy Value$8.7M
Current Direct Holdings7,500 shares (~$257K)
Latest Form 4 ActivitySep 30, 2025 (RSU vest)
RoleChairman, Co-Founder
Full ProfileView on 13F Insight

Institutional Context

BlackRock holds an 8.3% beneficial ownership stake in LendingTree per Schedule 13G/A filings. Vanguard Group holds approximately 4.99% (680,685 shares). Millennium Management had also filed a 13G for TREE, though the current status is unclear.

LendingTree itself reported 13.77 million shares outstanding as of December 2025, meaning Lebda’s 7,500 directly-held shares represent less than 0.1% of the float. His 10% beneficial ownership designation likely reflects shares held through indirect structures that are not captured in the directly-held Form 4 total.

What to Watch

  • TREE stock price vs. insider buying levels — multiple directors bought at $36.52 in June 2025, near the current $34 range. Whether they add more would signal conviction.
  • Lebda’s next Form 4 filing — with only 7,500 directly-held shares, any open-market purchase or additional RSU grant would materially change the picture.
  • Insurance segment growth trajectory — LendingTree guided for continued insurance carrier spend in 2026, which drove the Q4 beat. If that segment re-accelerates, TREE could retest the vesting-era $65+ range.
  • New CEO execution — Scott Peyree is now driving the “#1 Destination to Shop for Financial Products” strategy. Whether the AI-enhanced customer funnel delivers measurable conversion gains will define 2026.
  • Debt reduction — net leverage fell to 2.4x from 3.5x at year-end 2024. Continued deleveraging gives the equity more room to re-rate.

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