2018
Manufacturing · USD $85m competitor acquisition
The acquisition that never happened
Client wanted to acquire a competitor. On paper it made sense — market share, synergies, defensive move.
Three meetings later we advised against it.
Twelve months later the competitor entered administration.
What I was not sure about: I was not sure we could get the CEO to walk away without losing him. He had already told his team the deal was happening.
What I got wrong or almost got wrong: I almost let the timeline drive the decision. Momentum is seductive even when you know better.
Technology · AUD $40m revenue, family ownership
The founder who could not delegate
Every major decision went through one person. Growth had stalled for eighteen months. The board wanted a restructure.
We named three decisions only the founder could make. Everything else got an owner and a deadline.
Two quarters later things were moving again. Two senior hires stayed who had been packing their offices.
What I was not sure about: Week two I thought the founder would nod and ignore it. He did not. That surprised me.
What I got wrong or almost got wrong: I waited too long to say plainly that he was the bottleneck. Everyone in the room already knew.
Still true for me: Say the obvious thing early. Politeness is expensive at this level.
Manufacturing · USD $120m acquisition in diligence
Partnership deadlock before acquisition
Two equal partners had agreed to sell. Then one wanted to renegotiate the earn-out. The other wanted out. Forty-five days to close.
I wrote down what each partner actually needed versus what they were demanding. We restructured the earn-out so both could claim a win without reopening price.
Deal closed on schedule.
What I was not sure about: I was not confident either partner would sign until the morning of.
What I got wrong or almost got wrong: I underestimated how much of the fight was about pride, not money. The numbers were never the hard part.
Language technology · AUD $8m valuation, eighteen months runway
Raise again or pivot now
Strong IP, weak sales. The AI wave was about to make their product look obsolete whether it was or not.
Raise on a pivot — translation marketing and support — with a straight story about why the team still mattered.
AUD $8m, then AUD $16m a few months later.
What I was not sure about: The pivot might have been wrong. We raised anyway because running out of money was a worse outcome.
What I got wrong or almost got wrong: I should have pushed for the pivot six months earlier. We lost time being polite about a product the market had moved past.
Professional sport · International team operations, no corporate infrastructure
Corporate ICT from zero in two weeks
Personal phones, personal laptops, no central anything. Travel and admin were breaking down mid-season.
One cloud stack. Everyone on it. Fix the rest later.
It worked. Not pretty. It worked.
What I was not sure about: I thought half the staff would refuse to change devices. A few complained. Most were relieved.
What I got wrong or almost got wrong: Nothing major. Rare week.
Private equity · USD $100,000 per month offered
When not to take the mandate
PE-backed CEO wanted me to validate a strategy the board had already rejected twice.
I said no. I would have been expensive confirmation bias.
CEO left. PE brought in an operator chair. They asked me back six months later. I said no again.
Still true for me: Turning down work is part of the job. I still find it uncomfortable.
What I have lived through
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Track record