Episode 217: Canva’s AI Crisis, Karl Stefanovic’s Podcast Genius, Labor’s CGT Shambles, and Claude Design Changes Everything
The guys break down whether Canva has missed its golden window, why Karl’s split with Nine might be a brilliant move, and how the government’s startup tax carve-outs could smash founders & their teams
H3: The Contrarians catchup
Will Hayward gave a one-month business update for The Contrarians. The pod is growing fast, live events are in planning, and advertising revenue has been “surprisingly strong” from the start. His three asks: subscribe on all platforms, follow on YouTube and Instagram, and reach out if you want to advertise. Adam’s pitch to potential partners: “If you want to hit The Contrarians audience, you’re getting the decision makers, the founders, the CEOs, the CMOs, the CFOs. It’s the most premium audience in the country.”
Adam described Luxury Escapes’ journey from a sprawling multi-brand e-commerce business to a pure-play travel company. At peak complexity they ran Luxury Escapes, Scoopon, Kudo, Deals.com, a fashion business called Brands Exclusive, and a homewares business competing with Temple & Webster. The rule learned the hard way: every time you merge customer bases, “you lose 50% of the audience literally overnight.”
Adir on what to say to founders being threatened by a competitor: “If you hear someone on the other side of your deal telling you they’re going to crush you if you don’t sell, you should ask for more. That is a good sign for you.” The Luxury Escapes team heard exactly this from a rival five or six years ago. “This business has just continued to sort of fade away.”
Adir on Socceroos coach Tony Popovic choosing a different lineup in game two of the FIFA World Cup: “He was up against a team where clearly he felt if he played the game that he played in the first match, they would be able to adapt to it. Everybody judged him based on the output metric. Nobody talked about the input metric.”
Claude Design is, according to Adir, revolutionary. He used it to rebuild the entire front end of his brand equity analytics tool from a single screenshot and five lines of prompts. “It basically crafted 80% of what I thought I wanted without me even realising that’s precisely how I wanted it to look.” Listen for his verdict on Canva versus Claude Design.
Karl Stefanovic: the genius business move hidden inside a scandal
Karl Stefanovic parted ways with Nine Network after publishing and then retracting an interview with UK firebrand Tommy Robinson. The video was immediately uploaded to Pauline Hanson’s YouTube account and received 167,000 views. Stefanovic’s contract was already in its final year. Adam and Adir argued the whole episode was a win for almost everyone involved.
Adam: “He’s got a podcast business probably worth $20-30M today. Could be worth $100M. This is a genius business move by him. Whether it was intended or not, he’s played it brilliantly. I think Nine have probably gotten away with it pretty well as well. This is to me a great win-win.”
Adir: “This is literally $10-20M of free publicity he’s had. You can’t buy this kind of publicity. Money can buy you talking about your own stuff. It can’t buy other people talking about your own stuff because they think it’s good for them to talk about it.”
Adam: “I think Karl is really smartly picked up on that rightward trend. You can see the One Nation support is off the charts now. It’s the number one most popular party in the country. And Karl’s just, I think it’s just a really savvy guy who’s picked this up and he’s created the number one podcast in Australia in the space of four months.”
Labor is in a secret coalition with the Greens
The CGT legislation passed the Senate last week, pushed through by Labor and the Greens. In the same sitting, the government’s industrial relations bill, the one economic policy area where Adam and Adir gave Labor some credit, was pushed back. The broader political landscape has shifted dramatically in Adam’s view.
Adam: “You’ve got effectively the Greens calling the shots, the far-left, the ultra-far-left Greens, the socialists, potentially communist Greens, calling the shots in a coalition government with Labor.”
Adir: “I think if you would have asked me this six months ago I would have said you can’t compare. Like I might disagree with this government, but there’s still a trustworthy government. I think this government is totally untrustworthy today, and you can’t believe a word that they say.”
Adir: “I want to bring Tony Burke onto the podcast just to ask him one question, which is, will you commit on this podcast to not claiming negative gearing on your six investment properties, given you’ve stopped young people with no properties from ever being able to use it? Because if you believe it’s right to wipe out negative gearing, then walk the talk.”
Adam: “The core of the policy was right, but they executed it so badly that you can’t possibly give them a positive mark for it. They should have removed it for everyone, but they should have given people warning and maybe given a phase-in period of three or four years. And it should have been for everybody, not grandfathering older rich people.”
The CGT carve-outs: fake exemptions to a lie of a policy
Adam did a deep technical breakdown of the two “carve-outs” the government announced alongside the CGT changes. The first raises the small business CGT concession threshold from $2M to $10M turnover but applies a 30% minimum tax rate that was never disclosed. The second, the so-called innovative company carve-out, is more complex and, in Adam’s view, almost entirely unusable.
On the small business carve-out:
Adam: “The 30% minimum tax rate still applies for all this now. So previously you used to be able to stack these two discounts. Now you can index it, but you have this minimum 30% tax rate. This so-called $10M thing really isn’t that generous. The 30% minimum is 30% secret, 30% that they neglect to tell people about.”
Adam: “People that start their own businesses, they have sweat equity by virtue of the work they do and no cost base. That’s the group with no cost base. Self-started, motivated job creators, the backbone of Australian society. If you want your hair cut, if you want your toilet fixed, you need someone like this. So that’s who the 30% minimum tax really smashes.”
On the innovative company carve-out, which requires a company to be under $50M turnover, under 10 years old, unlisted, qualify for the ESIC framework, and employees must hold shares for at least five years:
Adam: “We were a $50M revenue business within two years of our business. We were a valueless business then, with virtually no profit and nobody was valuing us much. So we had really risk-taking early stage employees who would absolutely not qualify. And we’re just one out of thousands and thousands of companies.”
Adam: “If you’re an employee and it’s going to be fully acquired, there is no way the acquirer is going to let you as an employee hold those shares for another two years. Your shares are going to be compulsorily acquired as part of a drag provision, which means the buyer can force me to sell and the buyer will be forcing me to relinquish the tax benefit.”
Adam: “The company that fits into the intersection of all these criteria is a company with all this amazing potential up front, but sold in less than 10 years with a revenue of under $50M. We could call that company a failure. That is the company whose founders get the discount.”
Adir: “I believe this is a Labor government, do they realise how much power they’ve just given the company? If I have an employee and they’re at year four of their holding, do you know how much power I’ve got in firing them? They not only lose their job, but they miss out on the tax benefit.”
Adam: “Nobody has done more to increase the benefit of the wealthy versus the not wealthy than this Labor left government and their latest budget. Unintentionally, but that’s what’s happened.”
Does Canva sell now or be killed by a giant?
Adir’s hands-on experience with Claude Design has significantly sharpened his bear case on Canva.
Adir: “My increasing view is that I was right about this and it’s going to be very hard for Canva to compete. They’ve gone from being the giant killer to being at risk of being killed by a giant. I think it’s sell time. Like that’s my honest view. It’s time to go and find someone.”
Adir: “Canva should not IPO. Canva should basically go to their bankers and say, we want to be bought by Anthropic or OpenAI. It can be an all-stock deal, but the stock has to be non-escrowed and we sell it into their IPO as much as we can.”
Adir: “It’s very hard to build a generational company today with this level of tech change. If you want to build a generational company, build leather handbags, maybe you can build a generational company. But it’s very hard in tech.”
H3: Five other stories worth following:
Chinese AI models are narrowing the gap with leading US rivals, raising concerns that American restrictions may backfire by pushing businesses toward cheaper Chinese tools while limiting access to domestic models for trusted users.
OpenAI and Anthropic are pushing back against government limits after restricted model releases, while Austria is pitching the EU as a safer home for Anthropic, promising legal certainty, market access, capital, and values.
Michael overtook Oppenheimer as the highest-grossing biopic ever, Supergirl underwhelmed despite Krypto’s presence, and Toy Story 5 held the top box office spot, suggesting audiences still have appetite for familiar franchises.
Former Apple designer Julian Hoenig launched Amble, a minimalist street-legal electric buggy startup focused on short trips, with 2027 delivery slots already reserved by hospitality customers ordering roughly 40 vehicles worth $1m.
Former Starlink engineers launched Eclipse Space to help governments and companies build their own satellite constellations, using a fabless model that designs spacecraft while outsourcing manufacturing to make infrastructure cheaper and faster.