I agree. If they are buying in small amounts it doesn't mean much. It's all about how much they are putting on the line.

If a few members of the board buy $10k each when the share price is tanking it just looks like they had an idea during a board meeting to try and fix the share price. Directors don't want to give up the money from director fees easily. That could be more of the motivation than actually helping shareholders.

On the other hand if the CEO is buying significant amounts compared to their salary/net wealth, usually a very positive sign. However, you need to check they aren't trying to hid that the company is going under and they are just pumping the share price for easy capital?

I think the more important factor is just the general level of skin in the game and that they have held it for a long amount of time. That is a more positive sign to me. Doesn't matter if they are buying or even selling smaller amounts. If most of their net wealth is in the company you know they are working for you.

As Charlie Munger has said "show me the incentive, I'll show you the outcome"....

Hi @loshell - I think it was me that said that - it might have been an oversimplification but generally it’s true. Having said that it’s only a small factor to consider and I don’t think it would really sway me either way all else being equal.

Ideally you'd want to know the % of individual net wealth tied up in the company's shares to be able to gauge the true commitment and conviction, but alas that is not readily disclosed.

% of salary seems like an imperfect, but plausible and knowable proxy though.

I do pay attention to Director and other Inside share dealing, however, context is everything. (As @Strawman often says!) Some examples.

Sometimes, an Insider will sell down simply to reduce the concentration of their wealth in a single security. I don't blame them and don't see it as a lack of confidence in the company. I have personally been in the position as an insider earlier in my career when I sold down significantly because around 50% of my net wealth was in one company (due to share awards and the company itself being a 4-bagger over 5+ years). My holding broke my portfolio concentration rules, and I explained it as such in my notification to the Remco of my decision to sell. Curiously, you don't often see that as the reason given. Rather, there are references to meeting "tax obligations". I do wish there was more transparency/honesty in business!

Alternatively, a founder may have an orderly program of divestment over time. Take Richard White of $WTC. Over recent years he has been offloading small amounts of stock on an almost daily/weekly basis. He's spent a lifetime building the company and delivering a lot of shareholder wealth, with potentially a long road ahead. Surely, it is right that he monetises some so he can enjoy the fruits of his labour? When he started this, I recall he talked about "increasing liquidity". But I think this was long after liquidity was an issue. How about "I've worked bloody hard to build this business, and I want to enjoy it while I can." I don't think you need to be as explicity as David Dicker who said he wanted to buy a jet or a yacht or something like that. Good on him, though.

Conversely, I pay little attention when Directors buys shares as part of their regular Director remuneration. These purchases usually reflect little in terms of their total wealth and the purchases are almost an unwritten contract. So if one or more Directors aren't participating, I sometimes do a little digging.

I thought it was interesting when a large group of insiders at $AMS ploughed in their own funds at what was at the time seen to be SP weakness. This was clearly a concerted and deliberate effort to send a signal to investors of confidence. Given everything that is unfolding there, time will tell if their investments were wise or an act of collective self-sacrifice!

I do pay attention to insiders making significant, on-market purchases. For example, I saw David Williams on market purchases of $PNV earlier this year as very significant. He is a shrewd investor, the sums were significant and they aligned with my view that the company is undervalued (partly due to being a shorters' and traders' favourite, and partly due to the risk-off market sentiment and it being seen by some as having a biotech-type risk profile - it doesn't). OK, so perhaps some undue confirmation bias there on my part.

I kick myself for not paying attention to sales earlier this year by the $EML Chairman. It was significant, and it pressaged the unfolding of signficant bad news and shareholder value destruction. Those are facts and I am not ascribing foreknoweldge. But I just missed it, as I wasn't paying attention.

I do expect insiders to have some skin in the game. So, for example, with Swami Roate, new CEO of $PNV, I am patiently waiting for him to put some money in, and not just rely on his share grants. And in the case of $M7T, I am concerned that there isn't a stronger insider holding and this weighs on my assessment of risk, which means that IRL I will probably hold only 50% of what I might otherwise hold, as otherwise it looks like an emerging good business.

I' m not100% rigorous or consistent, but these examples demonstrate my current thought process and practice. Room for improvement for sure, and so I am very interested in what others are writing on this Forum. (This reply probably better sits on another Forum ... Insider Holdings and Dealings)