Sep 7, 2026 · 1h 30m
Expert360 sale and Corporate Travel Management ASX return signal market shifts
Expert360 Heartbreak, CTM is Back, Iran Stalemate gets less Stale and The Athlete Rich List
This episode provides an unvarnished look at the compounding pressures facing modern businesses, from startup exit realities and public market volatility to geopolitical threats and executive turnover.
- 1The sale of Expert360 highlights the harsh lessons of founder sell-downs and the critical importance of sustained board alignment.
- 2Corporate Travel Management faces a turbulent ASX return marked by massive value drops and looming class action threats.
- 3High-profile executive departures require public honesty and strategic management to protect organizational brand equity.
Don't miss
The detailed breakdown of how founder sell-downs and board dynamics led to the fire sale of Expert360.
The brief
Hosts Adam Schwab and Adir Shiffman unpack the brutal realities of business building, analyzing the painful fire sale of Australian startup Expert360 to SwipeJobs and what it reveals about founder sell-downs and board commitments.
The hosts dissect the turbulent return of Corporate Travel Management to the ASX, exploring the mechanics of its massive drop in value, potential class actions, and the high-stakes trading maneuvers that occurred during its suspension.
In a shift to sports and corporate culture, they analyze the unusually public dismissal of North Melbourne AFL coach Alastair Clarkson, using it as a case study for how modern organizations should navigate high-profile executive departures.
The discussion also tracks how elite athletes leverage personal brands for equity, the value of brand advocates who return products, and the rising geopolitical tensions in the Strait of Hormuz affecting global oil markets.
What was said on this episode
54 statements · 21 positive · 26 negative · 7 neutral
Modern entrepreneurship has different challenges rather than being simply easier.
“I'm not sure it's easier now than it ever was. Like, there's just different challenges.”
Listen at 5:02
About half of products use some variation of emotional blackmail to generate sales.
“Half of the products that are sold in the world are just some variation of emotional blackmail.”
Listen at 8:41
Entertainment workers are likely to be dismissed once they stop attracting audiences or winning.
“if you're in the entertainment industry, the minute you're not performing, getting an audience, etc., winning, making viewers excited, you know, and like fans are just viewers in another guise really, then, um, you're going to be brutally shown the exit.”
Listen at 13:18
A chair’s primary responsibility is protecting the organization.
“Your number one job is to protect the organization.”
Listen at 15:16
Separation agreements can exchange compensation for orderly departure and nondisparagement.
“we'll give you money if you do A, B, C, D, one of which is leave like nicely, and one of which is not disparage us publicly.”
Listen at 19:03
How companies treat ordinary departing employees matters more than treatment of executives.
“it's more of a big deal how you treat the non-CEO or the non-C-suite, how you treat regular people that leave an organization.”
Listen at 21:29
Strong brands are necessary for great consumer businesses or high-margin businesses.
“you can't build great businesses in the, in the consumer space without a really strong brand perspective or from a high margin perspective.”
Listen at 22:50
Loud customers with negative experiences pose the greatest reputational risk.
“The group that has the most potential to drag you down, uh, like loud people that have had negative experiences with the company, obviously.”
Listen at 23:29
People of student age are currently the main source of societal upheaval.
“if you look at where the societal upheaval is coming from right now, number one, it's coming from people of student age.”
Listen at 26:14
Student views today will probably become society’s views tomorrow.
“the views that students hold today, they are the views that society is probably going to hold tomorrow.”
Listen at 26:30
Student politics is where many people begin learning how to become politicians.
“this is where politics starts, okay? And I think like this is where people learn how to be politicians.”
Listen at 31:35
Mainstream parties’ absence from campuses signals poor future prospects.
“If the, if the Liberal Party and the Labor, even the Labor right, yeah, can't get a foot in here, personally I think it bodes badly.”
Listen at 31:42
Far-left radicalism creates openings that can help far-right movements take power.
“the far left just creates an opportunity for the far right to say, we'll save you. And then they end up generally taking power historically in democracies”
Listen at 33:52
Compulsory voting helps keep political outcomes near the center.
“you realize how important compulsory voting is to keep, to keep things in the middle, as close to the middle as you can get.”
Listen at 35:44
The Jordan–Nike deal created more value than any other brand-athlete deal.
“that is the greatest value by any brand and by any athlete in history.”
Listen at 38:48
The Jordan–Nike deal was essential to Nike becoming a mainstream brand.
“There would have been no Nike brand without that deal. Is my guess in the mainstream.”
Listen at 38:56
Social media has increased athletes’ ownership of their personal brands.
“in the social media era, athletes are taking ownership of their personal brands much more than happened previously”
Listen at 41:54
Athlete equity deals generate substantial wealth for athletes.
“that is how they're generating massive amounts of wealth.”
Listen at 42:12
Athletes are increasingly significant early-stage investors in technology companies.
“increasingly we're seeing it tech companies where athletes are a significant part of the early stage cap table.”
Listen at 48:10
An athlete will eventually become a billionaire through a startup exit.
“I suspect there'll be a billionaire that gets minted, an athlete billionaire will get minted from an exit at some point.”
Listen at 48:17
Athlete appeal in Australia is strongly geographically segmented.
“in Australia appeal is very geographically specific.”
Listen at 48:47
Athlete-brand marketing is harder to execute successfully in Australia than America.
“getting an athlete, smacking them together with a brand and driving that in Australia, it's just more difficult than doing it in the US.”
Listen at 49:38
Iran can achieve victory simply by keeping its regime in power.
“the Iranian regime just has to stay alive to win.”
Listen at 55:01
A prolonged US blockade of Iran will increase suffering among ordinary Iranians.
“the more that the US blockades Iran, the more that regular people will suffer.”
Listen at 55:04
Iran’s attempted attacks on US warships have worsened its strategic position.
“it's getting worse for the Iranians just by virtue of the fact that they tried to attack US warships.”
Listen at 55:19
Escalating geopolitical conflict can unintentionally produce a much larger crisis.
“when you play with fire, sometimes, you know, you create an inferno by accident.”
Listen at 56:48
Purging senior generals can suppress military initiative and endanger battlefield performance.
“that is the lesson of the danger of purging top generals and making an army feel scared to demonstrate initiative on the battlefield.”
Listen at 58:12
The Strait of Hormuz is steadily losing strategic value.
“the Strait of Hormuz is becoming less and less valuable every day.”
Listen at 58:34
The Strait of Hormuz blockade is weakening Iran’s position.
“the whole blockade's really weakening their position.”
Listen at 59:03
Trump would quickly accept Iran allowing Hormuz transit and freezing its nuclear program.
“I think Trump would do that deal in a second.”
Listen at 59:36
Founders should sell some shares during unusually favorable financing windows.
“when there's a golden window, which means everyone thinks the only way is up, including you as the founder, sell some stock.”
Listen at 1:05:42
Investors generally tolerate limited founder share sales during strong market conditions.
“investors are generally tolerant of some founder sell-down when the stock is very hot.”
Listen at 1:06:45
Bridget’s Telstra board appointment was Expert360’s only significant misstep.
“I thought that the only real misstep was was that Telstra board appointment?”
Listen at 1:10:27
CEOs should never accept external board appointments.
“I don't think any CEO should take an external board appointment ever.”
Listen at 1:10:38
Expert360’s sale returned roughly 30 cents per dollar invested.
“It's basically raising a dollar to get 30 cents back.”
Listen at 1:11:41
Expert360’s outcome was still positive despite returning less than invested.
“it still was a positive outcome.”
Listen at 1:11:52
Founder self-interest ultimately drives persistence during difficult periods.
“I do not want to be involved in a founder that does not have self-interest because ultimately on dark and lonely nights that is what's going to drive.”
Listen at 1:13:39
Insufficient growth and profitability prevent companies from raising more capital.
“If you're not growing enough and you're not profitable, no one's going to give you more money.”
Listen at 1:14:21
Companies lacking sufficient growth and profitability eventually shut down.
“And so eventually you're going to have to shut.”
Listen at 1:14:25
For investors, business failure without a realizable tax loss is the worst outcome.
“But the worst result is when the business goes zero and you can't get a tax loss.”
Listen at 1:15:15
Steve Johnson was somewhat wrong about Corporate Travel Management’s valuation.
“I think he maybe was a bit wrong in this one.”
Listen at 1:17:02
Corporate Travel Management remains significantly overvalued.
“this still appears significantly overvalued”
Listen at 1:18:01
Corporate Travel Management generated only $3 million in adjusted operating cash flow.
“its operating cash flow was only $3 million last year after you account for the intangibles payment.”
Listen at 1:18:40
Corporate Travel Management’s modest revenue decline was surprisingly good.
“I think it's amazingly good.”
Listen at 1:19:14
Corporate travel contracts typically last at least three to five years, limiting immediate customer losses.
“they tend to be 3, 5-plus-year contracts, so like worst case you lose everybody, you lose 20%.”
Listen at 1:19:33
Corporate Travel Management retained roughly 80% of renewing customers during the crisis.
“So they got an 80%, like, um, renewable churn rate.”
Listen at 1:20:49
Corporate Travel Management may report good results in its next reporting period.
“I think there's a good chance they might report a good next period if this is as bad as it got in the worst time.”
Listen at 1:22:08
Corporate Travel Management is likely to face extensive shareholder class-action lawsuits.
“it's about to be a nightmare of class action lawsuits coming its way.”
Listen at 1:22:34
Corporate Travel Management may need rescue capital that dilutes shareholders by 50–80%.
“you might end up with a rescue capital raising to pay this one-off cost that dilutes shareholders another 50% or 80%”
Listen at 1:23:12
Jamie Ferris apparently sold his entire stake in Corporate Travel Management.
“apparently Morgans last week did 2 block trades for an amount that equaled Jamie Ferris's stake in the business. So my mail is that Jamie, the founder, has sold his entire stake.”
Listen at 1:23:40
Corporate Travel Management made $48 million in adjusted net profit last year.
“Well, literally made $48 million net profit last year before the one-off.”
Listen at 1:24:42
Investors who bought suspended CTM shares made roughly 15 times their money.
“whoever bought that stock while it was suspended, they, um, made 15x their money today”
Listen at 1:25:59
Successful trading involves asymmetric upside with manageable downside.
“the trick is to have huge— have an asymmetric trade where there's huge amounts of upside, and but you can manage the downside.”
Listen at 1:26:28
Corporate frauds can remain concealed for extended periods.
“frauds can be hidden for a long time.”
Listen at 1:28:48
Statements are attributed to the speaker as said on the episode and reflect their view at the time, not PodLume's. They are not advice.