Equities likely grind higher, but the upside is modest and fragile. Leadership remains narrow — big tech, AI plays, and selective energy/industrial names still carry the torch. Defensive sectors and quality balance sheets should be favored as volatility spikes around macro data and politics.
Bottom line: late-cycle vibes. The rest of 2025 is a trader’s market, not a buy-and-forget playground. Ride the waves, keep stops tight, and focus on insider conviction and strong fundamentals. The wall of worry isn’t coming down — it’s just getting taller.
Name: Claude LeBlanc
Position: Chief Executive Officer
Transaction Date: 10-01-2025 Shares Bought: 25,000 shares an Average Price Paid of $8.54 for Cost: $213,500
Company: Ambac Financial Group Inc. (AMBC):
Ambac Financial Group, Inc., founded in 1971 and headquartered in New York, is a financial services holding company operating through two business segments: Specialty Property and Casualty Insurance and Insurance Distribution. The Specialty Property and Casualty Insurance segment focuses on program insurance for commercial and personal liability risks, while the Insurance Distribution segment provides services through managing general agents, underwriters, brokers, and other underwriting and distribution businesses.
Claude LeBlanc is the President and Chief Executive Officer of Ambac Financial Group, Inc., as well as a member of the board of directors. He joined the company in January 2017 and has since led a transformation of its business strategy. Prior to Ambac, he served as Chief Financial Officer and Chief Restructuring Officer of Syncora, and earlier held senior roles in corporate development and strategy at XL Capital and PricewaterhouseCoopers. Mr. LeBlanc earned a B.A. in Economics from York University, a B.Com. from the University of Windsor, and an MBA from the Schulich School of Business. He is both a Chartered Accountant and a Certified Public Accountant.
Insomniac Hedge Fund Guy Opinion: Ambac’s transformation is bold: shedding its legacy guarantee business and embracing a distributed specialty insurance + MGA model is the kind of surgical reset rarely attempted with this scale. The insider buying demonstrates conviction—LeBlanc and Trick are putting skin in the game. But the needle hasn’t moved enough: profitability remains fragile, execution risk is high, and the valuation assumes near-perfect execution. My DCF suggests the equity is overvalued at today’s multiples unless growth, margin, and cash flows surprise materially to the upside. A successful turnaround could deserve a rerating, but as things stand, Ambac is a speculative restructuring play, not a capital-safe compounder. I’d lean neutral-to-cautious — the upside is outsized if they pull it off, but the downside is sharp if they don’t.
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Insiders sell the stock for many reasons, but they generally buy for just one – to make money. You’ve always heard the best information is inside information. Everyone with any stock market experience pays close attention to what insiders are doing. After all, who knows a business better than the people running it? Officers, directors, and 10% owners are required to inform the public through a Form 4 Filing of any transaction, buy, sell, exercise, or any other within 48 hours of doing so. This info is available for free from the SEC’s Web site, Edgar, although we subscribe to SECForm4 as they provide a way to manage and make sense of the vast realms of data. I’ve tried a lot of vendors. SECForm4 is one of the smaller ones, but I like supporting Frank. He is not arrogant. He’s helpful and has great prices. He also trades on his own data, so I like people that eat what they kill.
The bar is different from selling because the natural state of management is to be a seller. This is because most companies provide significant amounts of management compensation packages as stock and options. Therefore, we analyze unusual patterns with selling, such as insiders selling 25 percent or more of their holdings or multiple insiders selling near 52-week lows. Another red flag is large planned sale programs that start without warning. Unfortunately, the public information disclosure requirements about these programs, referred to as Rule 10b5-1, are horrendously poor. Also, planned sales that pop up out of nowhere are basically sales and are seeking cover under this corporate welfare loophole. I also generally ignore 10 percent shareholders as they tend to be OPM (other people’s money) and perhaps not the smart money on which we are trying to read the tea leaves. I say generally because some 10% shareholders are great investors. Think Warren Buffett and others
Of course, insiders can also be wrong about their Company’s prospects. Don’t let anyone fool you into believing they never make mistakes. Do your own analysis. They can easily be wrong, and in many cases, maybe most cases, have no more idea what the future may hold than you or me. In short, you can lose money following them. We have, and we curse aloud; what were they thinking!
We like Fly on the Wall for keeping up with what events might be happening, analysts’ comments, and whatever else could be moving the stock. Dow Jones news service is an essential tool, but many services pick up their feed like they do Bloomberg. For quick financial analysis, it’s hard to beat Old School Value.
A big callout to my assistant Ambreen who sets up this conversation by listing the notable buys that I’ve identified as soon as practically possible. She probes the 10k for a reasonable description of the business. I’ve found that to be the most accurate and succinct place to find out what a business actually does. When I have time, over the weekend, I’ll add some preliminary analysis to the Opinion at the end. Sometimes I won’t update this for a couple of weeks or more. A good way to use this blog is as I do, it’s a reference point and filing cabinet for various stocks with notable insider buying. It’s one of many tools I use. I regularly live on Chat GPT, Gemini, Claude, and occasionally Microsoft Copilot. I find the footnotes research very helpful in eliminating errors from AI hallucinations but these opinions are likely to contain inaccuracies due to the nature of the LLM’s.