Ruslan Kogan, the CEO of ASX 300 retail share Kogan.com Ltd (ASX: KGN), has just added one million shares to his personal portfolio in his first share purchase since July 2020.

According to an ASX disclosure, Kogan purchased the shares through a trust on 25 and 26 February on-market at an average price of $4.77 each.

The $4.77 million purchase raised his stake in the online empire he founded in 2006 from 15.01% to 16.86%.

What makes this purchase particularly interesting is that, apart from participating in a Share Purchase Plan in July 2020, Kogan hasn't bought shares since the year that the company was floated in 2016.

His purchase follows the company's return to profitability in FY24 after several hard post-COVID years.

Why does this bode well for the ASX 300 retail share?

Any time a senior manager purchases shares in the business they help run, it indicates their personal confidence in the company's future.

They are essentially 'putting their money where their mouth is' and investing their own savings into the business, obviously with the expectation of a future gain.

When Kogan released its 1H FY25 results last month, Ruslan Kogan sure sounded optimistic.

He referred to the company's return to profitability in FY24 and said they had since built on that momentum and "returned the business to strong sales growth in 1HFY25".

Kogan commented:

This was achieved through disciplined execution, operational efficiencies, and strategic initiatives that we expect will continue to drive sustainable growth into the future.

As our customers continue to navigate the ongoing cost-of-living crisis, we are committed to easing the burden by offering market-leading prices on the most in-demand products and essential services.

By leveraging our scale and strong supplier relationships, we deliver remarkable value.

When was the last time Ruslan Kogan bought shares?

Kogan purchased 5,240 Kogan shares through a Share Purchase Plan in July 2020.

The capital raising's issue price was $11.45 per share.

Apart from this, the last time Kogan bought shares in his company was in December 2016.

That was the year Kogan began trading on the ASX.

At the time of its listing in July 2016, Ruslan Kogan owned 69.5% of the company.

Since then, most of Ruslan Kogan's transactions have involved selling the ASX retail share.

This is not uncommon in rising companies where senior executives — usually the founders — hold a substantial stake.

Over time, shareholders put pressure on the company's major stakeholders to sell down some of their holdings to enable other shareholders to raise theirs.

This is considered prudent as listed companies grow in size and popularity with investors.

What about other CEO transactions in this ASX retail share?

This is one of Kogan's biggest personal sales since the float occurred in August 2020.

By that time, Kogan had reduced his personal stake in Kogan.com to 20.41%.

He sold 5,284,441 shares off-market for $21.60 per share, reducing his stake to 15.01%.

That proved to be a very shrewd move.

As the chart below shows, 2020 was an absolute banner year for the ASX retail share.

It was the first year of the pandemic, and locked-down customers were shopping up a storm online.

The Kogan share price experienced an astronomical 562% rise in just seven months that year.

Kogan shares lifted from a closing value of $3.79 per share on 16 March 2020 to what remains the company's all-time record-high share price of $25.10 on 20 October 2020.

It was a rough road from there, with the ASX retail share tumbling over the next few years.

In December 2021, Kogan dropped out of the S&P/ASX 200 Index (ASX: XJO) and into the S&P/ASX 300 Index (ASX: XKO).

Only two transactions between August 2020 and January 2025

Since that sale in August 2020, Kogan has retained his 15.01% stake and disclosed only two other transactions in the ASX retail share before last month's purchase.

The first was an options exercise in April last year. Kogan exercised 3.6 million options due to expire on 30 June this year at $5.29 per share for a cash settlement.

Exercising an option for a cash settlement means Kogan was paid the difference between the strike price of $5.29 and the market share price at the time of the transaction.

On the day of the transaction, Kogan shares traded between $7.76 and $7.99 per share.

The second transaction was the awarding of 348,195 performance rights in December last year.

Kogan share price snapshot

The ASX 300 retail share closed at $4.68 per share on Friday, down 3.31% for the day.

The Kogan share price is down 43% over the past 12 months.

This compares to a 2% lift in the ASX 300 over the same period.