Sydney entrepreneur Joseph Daoud says he never expected to be playing tennis with the Prime Minister.
But frustration with Labor’s “Ambition Tax” became too difficult to ignore — prompting the founder of It’s Simple Finance to put $16,500 of his own money on the line to win a charity auction for a tennis match against Anthony Albanese at The Lodge this spring.
Mr Daoud has been training three times a week with a local coach, and while he intends to give the PM a run for his money between the white lines, his real target is the tax changes he believes will punish Australians trying to get ahead.
“I’ve been told the PM is a very, very good tennis player, and my prior tennis experience was mostly on Wii Sports,” Mr Daoud told News24.com.au.
“It’s not every day you get to play tennis at The Lodge, so I want to put my best foot forward. But let’s be honest, I’m the underdog.
“He’s got the home court advantage. I’ve got thousands of Australians in my corner.”
Mr Daoud bought the charity tennis match at the Parliament House Midwinter Ball charity auction in order to raise his concerns about tax changes with the PM.
He argues the Albanese government’s negative gearing and capital gains tax changes will discourage investment and entrepreneurship.
Mr Albanese and Treasurer Jim Chalmers had promised not to touch the tax settings before the federal election but broke their commitment in the 2026 federal budget.
Under the new rules, the government will scrap the 50 per cent CGT discount and introduce a cost base indexation and a 30 per cent minimum tax rate.
It will also limit negative gearing to new builds, while grandfathering the system for landlords who already benefit from the scheme as of 7.30pm May 12, 2026.
The legislation passed Parliament in June, with the government arguing it would create a fairer tax system and “level the playing field” for workers and first home buyers.
For Mr Daoud, however, the issue is less about political philosophy on taxation and more about what he sees happening to people trying to build something.
“I don’t have a grand philosophy about taxation,” he said.
“I’ve got a pretty simple view that if you get up early, take a risk and build something, the reward shouldn’t be a bigger bill.
“That view was shaped by the people I talk to every day, not by a textbook or a party.”
Mr Daoud said after the budget he received hundreds of phone calls from people who were angry, confused and deflated.
“The government hit small business with the CGT (capital gains tax) discount changes and called it levelling the playing field. Levelling it for who?” he said.
“The only people who ever built anything on that field were the ones about to get taxed for it. People built something on the rules they had, and all of a sudden the rules were gone.”
That frustration led to Mr Daoud’s Canberra Airport campaign, where he spent $17,500 on 18 billboards carrying the message “Stop the Ambition Tax”.
The billboards were deliberately timed to put the campaign in front of MPs, staffers and journalists arriving in the capital.
But when that didn’t stop the government, he dropped another $16,500 on the Parliament House Midwinter Ball charity auction tennis match with Mr Albanese.
The unlikely tennis contest will be one-on-one, with no guests courtside – but Mr Daoud has the chance to invite three people after the game ends.
He is searching for three Australians to join him and the PM for refreshments, with each guest given the opportunity to put a question directly to the Prime Minister.
“This match was never about me. It’s about the thousands of everyday Australians who’ve backed (the Stop the Ambition Tax) campaign,” he said.
“I’m running a national search for three everyday Australians to join me for a chat with the PM after the match, and each of them gets to put a question directly to him.
“The local kebab shop owner, the barista, the tradie who’s just gone out on his own, the single mum working two jobs.
“The people who are the engine room of this country and almost never get a seat at the table. We cover their travel.
“No everyday Australian should have to pay to ask the PM a question he should be answering anyway. All they need to bring is their question.”
Nominations are open now at stoptheambitiontax.com/tennis and close 30 August, with the three announced the following day.
While Mr Daoud has been an increasingly vocal critic of the government, he rejects the suggestion that he is simply a partisan commentator.
“I’ve voted Labor in the past, and I’ve voted the other way too. I’m a swing voter. I vote for policy, not party, and I always have,” he said.
“This campaign isn’t about politics. It doesn’t matter whether you vote Labor, Liberal or Greens, ambition is worth standing up for.”
“The fact the government has already had to carve out exemptions shows they know it too.
“If Labor went back to backing the people who back themselves, they’d have my vote again. Right now, they don’t.”
Asked about his motivations, Mr Daoud also insists he has no intention of turning his campaign into a bid for Parliament.
“I unashamedly hate Canberra and can’t see myself ever running for Parliament,” he said.
“But a year ago I couldn’t see myself playing tennis with the Prime Minister either, so who knows what’s around the corner.”
For now, the next step is The Lodge, where Mr Daoud expects to lose the tennis — but hopes to win something more important.
“If I take a game off him I’ll be happy. If I win, I’ll be asking for a rematch on the tax changes too,” he said.
“What I want from the afternoon is answers. How does taxing a young person’s share portfolio help a first home buyer?
“How does taxing someone’s Pokemon card collection help a first home buyer? Nobody’s answered that without a staffer in the room.”