What Happens When You Feed Insider Filings Into ChatGPT?

You get fast, data-rich insights like this.

Using ChatGPT to analyze recent Form 4 filings, we uncovered the top insider buying activity across public markets—highlighting where CEOs, chairs, and directors are putting real money to work.

From clustered buys in tech to conviction plays in REITs and regional banks, these signals often precede medium- to long-term gains.

Here’s what smart capital is telling us this week.

🧐 Recent Insider Purchases

A good summary from recent filings shows the top issuers with net insider buying over the past seven days (through July 7, 2025):

Net Buying Leaders (Value ≥ ~$1M):

• Asana (ASAN) – ~$6.09 M

• Welltower (WELL) – ~$3.03 M

• Sprott Focus Trust (FUND) – ~$1.45 M

• First Guaranty Bancshares (FGBI) – ~$1.06 M

• Freedom Holding (FRHC) – ~$1.00 M

These clearly represent large insider purchases in this week’s data.

🔍 Sector Breakdown & Notable Examples

I then manually looked up sectors for those tickers:

1. Technology / Software

• Asana (ASAN)

  • Sector: Technology – Software (collaboration tools)

  • Insider: Dustin Moskovitz (President, CEO & Chair)

  • Buys: ~225,000 shares ($3.06M and $3.05M, total ~$6.09M)

  • Structure: Two successive days by same insider (clustered).

2. Real Estate / REIT

• Welltower (WELL)

  • Sector: Real Estate Investment Trust – Healthcare REIT

  • Insiders: (multiple officers/directors likely)

  • Net buying: ~$3.03M aggregated

  • Clustered across insiders (multiple filings).

3. Financial / Banking

• First Guaranty Bancshares (FGBI)

  • Sector: Financial – Regional Bank

  • Net buying: ~$1.06M insider purchases aggregated

  • Likely director/officer cluster.

4. Closed‑End Trust / Asset Management

• Sprott Focus Trust (FUND)

  • Sector: Financial – Asset Management / Closed-End Fund

  • Insider: Officers/directors; ~$1.45M net buys

5. Financial / Financial Services

• Freedom Holding (FRHC)

  • Sector: Financial – Diversified Financial Services

  • ~ $1.0M net insider buys

📊 Sector Representation

Top 3 sectors by representation in this week’s large insider buying:

1. Technology / Software – led by Asana's heavy insider purchases

2. Financials – investors in regional banking and asset/trust vehicles

3. Real Estate / REIT (healthcare) – with Welltower

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📌 Summary & Possible Implications

• Technology / Software (Asana): The CEO’s multi‑day, high‑value purchases suggest strong confidence in growth prospects—perhaps upcoming product announcements or enterprise adoption momentum.

• Financials: Insider buying in a regional bank and asset management trust indicates comfort with financial sector fundamentals or company‑specific strength.

• Healthcare REIT: Directors/officers buying Welltower shares may believe in resilient income streams and favorable healthcare real estate trends (e.g. aging demographics, growing demand).

For medium‑term investors, clustered insider purchases—especially by CEOs and directors—can be interpreted as meaningful bullish signals.

While there’s no overwhelming sector dominance, Technology (software) clearly stands out, followed by Financials and Healthcare REITs. Together, these suggest selective optimism from insiders in those areas.

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Disclaimer: This newsletter is for informational purposes only and does not constitute financial advice. Always conduct your own research before making investment decisions.