Billionaire Blues: Zak Calisto Loses R3.6 Billion in Karooooo Share Shake-Up

South Africa’s homegrown tech titan takes a major financial knock after offering discounted shares. But is this a loss, or a long-term play?

South African-born tech mogul Zak Calisto made headlines this week, not for a new tech breakthrough, but for shedding a staggering R3.6 billion from his personal fortune.

The founder of Cartrack and Karooooo, Calisto’s net worth took a major hit after he announced plans to offload 1.5 million of his own Karooooo shares in a move meant to boost market liquidity. But what followed was a sharp decline in share price, a public market correction, and one of the biggest personal financial losses for a South African billionaire this year.

Why Calisto Sold His Shares and What Went Wrong

The sale was structured as a guaranteed public offering, with shares priced at $50 each — well below the $59.53 trading price on the Nasdaq and R1,049.99 on the JSE the day before the announcement on 11 June 2025.

While these shares were sold through underwriters (and not yet directly on public markets), investors reacted swiftly. The result? Karooooo’s share price dropped to $47.34, sending shockwaves through the tech investment space.

Calisto’s losses came from two fronts:

• R252 million lost on the discounted sale of the 1.73 million shares.

• R3.4 billion wiped off the value of his remaining 17.7 million shares due to the declining stock price.

The end result? A drop from R20.4 billion to R16.8 billion in net asset value, all in a matter of days.

Was It Worth It? Analysts Weigh In

While it may seem like a disaster on paper, analysts say there’s a bigger picture at play.

According to Roy Mutooni of Sanlam Investments, the share sale was long overdue and may actually solve a long-standing liquidity issue that’s plagued Karooooo on the Nasdaq.

“The stock’s high valuation was being driven by low liquidity,” Mutooni explained.
“Calisto let the valuation run on the back of a liquidity premium. This placing changed that.”

Shane Watkins from All Weather Capital echoed the sentiment, arguing that a larger free float will give investors a clearer sense of the company’s real market value.

“We’ve never had proper price discovery with Karooooo,” Watkins noted.
“A bigger free float helps fix that.”

Behind the Billionaire: Zak Calisto’s SA Tech Success Story

Calisto’s journey from humble beginnings to global tech CEO is the kind of story South Africa rarely tells enough.

Born in Portugal, raised in Mozambique, and later settled in South Africa, Calisto dropped out of actuarial studies at Wits and entered the workforce via Standard Bank. After cutting his teeth in the telematics industry with Netstar, he launched Cartrack in 2004 — a modest vehicle recovery service that would grow into Karooooo, now a multinational SaaS powerhouse listed on the Nasdaq and JSE.

Today, Karooooo provides data analytics, AI video, fleet tracking, and IoT solutions across multiple continents, with a major footprint in South Africa, Europe, and Southeast Asia.

Strong Financials, Despite the Sell-Off

What’s ironic is that the sell-off comes at a time when Karooooo is actually doing exceptionally well.

In its Q4 2025 results, Karooooo reported:

• Cartrack subscribers up 17% to over 2.3 million

• Annualised recurring revenue up 17% to R4.38 billion

• Operating profit up 30% to R385 million

• Earnings per share up 19% to R8.11

In other words, the company fundamentals remain solid — and Calisto knows it.

“We’re seeing strong growth in Southeast Asia, solid customer acquisition, and exciting innovation,” he said in a recent earnings call.
“We’re optimistic about 2026.”

What This Means for Investors

Despite the initial shock, this may actually mark a maturing moment for Karooooo. By increasing its free float and reducing overreliance on one large shareholder, the stock could attract a broader base of long-term investors.

For Calisto, the loss is more strategic than personal. By loosening his grip, he may have sacrificed R3.6 billion in net value, but potentially gained credibility and transparency in global capital markets.

And for the rest of us? It’s a reminder that in the high-stakes world of tech stocks, wealth can be paper-thin — until the markets say otherwise.

Zak Calisto may have lost billions on paper, but he’s still running one of South Africa’s most successful global tech ventures. The market may have corrected, but the man is far from out of the game.