Boomerang Boss: Altman, Jobs, Dorsey and the other CEOs who came back for seconds

Sam Altman’s sacking as CEO of OpenAI came completely out of the blue – but his return to the role just days later was equally unexpected.

However, while he may be unique in terms of the short timeframe between stints as CEO, he’s far from the first to ‘boomerang’ back into the top spot.

Steve Jobs at Apple, Jack Dorsey at Twitter, Michael Dell of Dell, Howard Schultz at Starbucks and Bob Iger at Disney are some of the best-known examples of boomerang CEOs

What happened with Steve Jobs?

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Probably one of the best know CEOs in the world – and the man who helped shape so much of our modern technology.

He co-founded Apple with Steve Wozniak back in 1976, and it quickly became one of the big players of the burgeoning personal computer market – going toe to toe with big players like IBM.

But by the early 1980s, Jobs felt that he needed an experienced businessman running and marketing the company.

So he lured a man called John Sculley, who was president of Pepsi Co at the time, with the legendary (and typically over-the-top) line of "do you want to spend the rest of your life selling sugared water, or do you want a chance to change the world?"

It worked, and Sculley came on board as CEO, freeing Jobs up to focus on the development of new Macintosh computers.

But while the relationship started well things soured quite quickly.

Jobs’ odd management style butted up against Sculley’s more traditional approach. Meanwhile the next PC Jobs led the development of – the Lisa – ended up a flop.

When Sculley tried to get Jobs and his Macintosh division under control, Jobs moved to have the CEO he brought in fired. But the board instead backed Sculley, and Jobs was shown the door instead.

But it didn’t take too long for things to turn for Sculley too, and he was fired in 1993 due to the company’s flagging performance.

Apple then spent the next few years losing ground to its rivals – with its software and hardware falling behind rivals. And by the mid-90s it was really on the verge of bankruptcy.

Its only hope was to bring out new software that would catch up with everyone else, but it was unable to do that in-house.

So it made a Hail Mary pass of buying up another company with better software – and in 1997 snapped up a firm called NeXT.

That happened to have been founded and headed up by none other than Steve Jobs.

The deal was finalised in February 1997, bringing Jobs back into Apple once more.

And within months he became the defacto CEO once again – and set about reviving the ailing business.

That software he made at NeXT became the basis for pretty much all of the software that Apple became known for in the following years – like iTunes and the App Store.

And, of course, the revived Apple went on to produce massive hits like the iPod, iPhone and iPad.

By August 2011, just two months before Jobs died, Apple became the most valuable company on the global stock market for the first time.

Jack Dorsey’s return to Twitter probably won’t be as fondly remembered as that, will it?

We’re still getting to grips with the consequences of Dorsey’s second term as Twitter CEO.

Dorsey was one of four founders of Twitter, which debuted in March 2006.

And he was CEO for it initial period of staggering growth, but stepped aside in late 2008.

He was still heavily involved in the company, though, acting as chairman while still being involved in the development of the service and its promotion worldwide.

And he was instrumental in focusing it on the quality of the service – and on growing users – rather than trying to make money from it.

But profitability has remained a problem for Twitter to this day.

Fast forward to 2015, and Twitter CEO Dick Costello stepped down, opening the door for Dorsey to return as interim CEO.

But he ended up staying there until late 2021 – when he stepped down once again.

And he later claimed that one of the reasons for his departure that time was a failed attempt at getting Elon Musk added to the Twitter board.

But even when he was no longer CEO, Dorsey remained an important figure at Twitter – not least because he had a sizable shareholding.

That meant that, when Musk did start making moves at buying the social media site, Dorsey remained pivotal.

At once stage he said Musk ‘cares deeply about our world and Twitter's role in it’.

And of course, we know Musk ultimately acquired Twitter at a very inflated price of $44 billion – which valued Dorsey’s stake at $1 billion.

Interestingly, though, he didn’t cash it in – instead he rolled it into the new Twitter holding company, meaning he still has a stake in the business.

That also suggests that he sees value in the approach Musk has with the app.

Though at the same time, Dorsey is also behind BlueSky – which many see as the best alternative to Twitter (though it’s still invite-only).

So he seems to be hedging his bets about the future of the social media site.

What about Disney?

Yes, that’s still going through the second coming of its boomerang CEO – Bob Iger.

He first became CEO of Disney in 2005 – and he set about completely revolutionising the company.

He was the one responsible for acquiring Toy Story-maker Pixar, before going on to acquire LucasFilm (and, as a result, the Star Wars franchise) as well as Marvel (bringing characters like Iron Man, Thor and Captain America to the Disney fold).

And eventually Iger paid Rupert Murdoch $71 billion to take over Fox – which saw The Simpsons, Avatar and many other properties move to Disney.

And while it’s generally believed that Iger overspent – especially for Fox – buying up those franchises and that big library from Fox proved crucial when Disney+ was launched in late 2019.

And that was essentially Iger’s crowing achievement – he retired as CEO in early 2020, being replaced by another Bob – Bob Chapek, who had been in charge of parks.

But Chapek was a bit of an unlucky general – because he took over just as the pandemic took hold, which saw all of their parks revenue dry up, as well as the money they made from cinema releases.

But he also made some of his own mis-steps, restructuring the company in a way that didn’t sit well with creatives in Disney.

He also seemed to have a hard time managing talent, with a very public spat with Scarlett Johansson being a good example of that.

Some also feel he was given a poison chalice by Iger – because not only was Iger seen as a Disney legend, he also left behind a bloated company with huge costs, and lots of debt.

And in the end Chapek was ousted just two years into his term as CEO – with Iger coming out of retirement to take the reigns once again.

What was handy for him, though, was that Chapek had done a lot of the dirtier work, like cutting staffing numbers back to try to reign in costs.

Iger has done more of that, though, and significantly scaled back its streaming plans too.

Has anyone done more than two stints as CEO of a firm?

Yes – Howard Schultz has served three separate terms as CEO of Starbucks.

The first was in 1986 – and while he wasn’t a founder of the company, he was responsible for creating the Starbucks people know today.

Because the original Starbucks was focused on selling coffee beans – not making coffee.

Schultz tried to convince the owners to move in that direction but they felt it was too expensive and risky, so he left, set up his own café with Starbucks as an investor.

Shortly after that he moved to buy the Starbucks brand from the founders and began to build the chain that we know today.

By the time he ended his first stint as CEO in 2000, Starbucks had more than 3,000 outlets worldwide.

But Schultz was brought back in in 2008 – during the height of the financial crisis – to help steady the business once again.

And he was fairly ruthless in doing that – in 2008 he announced he was closing 600 unprofitable outlets, with up to 12,000 people losing their jobs.

Just six months later he closed another 300 stores – with more than 6,000 being laid off as a result.

But investors loved him – with the value of the company sky-rocketing during his second term.

And despite the cuts he did continue to build the business.

By the time he stood down for a second time in 2016, Starbucks had more than 25,000 outlets worldwide.

And he completed his CEO hat-trick last year – this time as interim CEO – a position he held for a year, ending in March of this year.

Are there no female boomerang CEOs?

They’re few and far between.

One example of a female boomerang CEO at a big company is Susan Cameron of Reynolds American.

Neither she nor the company would be a household name, but they’re a big US tobacco firm that makes brands like Camel.

The lack of female Boomerang CEOs is in large part due to the lack of female CEOs in general – particularly at larger firms.

According to Fortune, just over 10% of the current Fortune 500 companies (that’s the largest US companies by revenue) are led by a female.

And about a quarter of those only became CEO in the past year.

Which is really a remarkable statistic in this day and age.

So why do we have so many boomerang CEOs?

It’s worth noting that in most cases of boomerang CEOs, you’re looking at founders.

Of the ones listed here, Bob Iger is the only non-founder to return. (Schultz technically wasn’t a founder of Starbucks, but he did effectively found the Starbucks café chain business).

What seems to happen when a company is struggling is that investors get a bit misty eyed about the good old days when the brains behind the business was calling the shots.

There’s an impression – reasonable or not – that founders have some innate understanding of the business that others do not.

But perhaps there’s also a degree of ego there – they don’t want to see their ‘baby’ fail, or others succeed in making it better.

And maybe, when a firm is in real trouble, they’re the only people willing to put the work in to turn it around, rather than sell it off or liquidate it altogether.