Insights
Leadership, decision-making, and the isolation that comes with it.
Notes from Leo Judkins on running the iGaming Leader Mastermind, and the patterns he sees in senior operators across the industry.
Start here · The complete guide
Peer advisory groups for iGaming executives: a buyer’s guide
What actually makes a peer advisory group worth your time, and what you should be sceptical of before you commit.
Read the guide →Isolation & decision-making
The anticlimax of the exit: why selling your company doesn’t feel like you think it will
Not devastating. Not a disaster. Just hollow.
The Dark Passenger: why the thing that makes you a great founder makes you a bad one to step back
The persona that got you here doesn’t get a graceful exit just because the org chart changed.
The neutral board of directors you don’t have
The air is thin at the top.
The hidden cost of making every decision alone
The gap between good and great, sitting there, permanently uncollected.
Why your leadership team can’t be your sounding board
Your team can be excellent and this gap still exists. It’s not about their ability, it’s about their stake.
How to get honest feedback when you’re the boss
The problem is structural, and no amount of warmth fixes it on its own.
Why iGaming founders have no one to talk to
Who do you call when the ground moves under a market you’ve built your business on?
7 signs you’ve outgrown your current network
Not “who do you know.” Who do you actually talk to.
Leadership & delegation
Why your best people keep becoming your bottleneck (and so do you)
Every time you fix someone else’s work for them, you become their crutch.
The industry’s deadly cocktail: travel, alcohol, pressure, and the habits that break under it
On their own, any one of them is manageable. Together, they’re a deadly cocktail.
From firefighting to strategy: a framework for iGaming leaders buried in ops
You’re not failing at your job. You’re doing a different job than the one you actually need to be doing.
What separates iGaming executives who scale from those who stall
Talent isn’t the difference. What separates them is smaller, harder to see, and rarely about intelligence at all.
Fit & what members say
Who this isn’t for: an honest look at fit
If a peer advisory group is genuinely vetted, it should say no as often, and as honestly, as it says yes.
Confirmation, not advice: what members actually say the group gives them
By the second session, something had shifted, and it wasn’t the advice. It was the questions.
Inside a vetted iGaming mastermind: what actually happens in the room
No performance, no pitching. Structured, rotating focus on whatever’s actually sitting on each person’s desk that week.
Mastermind vs executive coaching: what senior iGaming leaders actually need
Not a competing product. Two different problems, and conflating them is why some leaders think this base is covered when it isn’t.
Earlier notes
Only do the things that only you can do
The things that made you good at your job become the things that hold you back.
You rise to the level of your environment
Our kids didn't get worse. They got better.
80 redundancies, and I couldn't tell a soul
The most devastating experience of my professional life.
I froze on stage. Ten years apart.
The fear doesn't go away. It never does.
The day I resigned as Director
Not because the job was bad. Because I'd become someone I didn't recognise.
Knowing what you can't say
70% of what's going on, there's nobody I can talk to about it.
The $1,100 that changed everything
Three months earlier, I couldn't get out of bed.
The 3.5-hour drive that changed everything
I had no plan beyond the interview. No idea Gibraltar even existed.
"I lost confidence in myself."
Said like he was commenting on the weather.
The pressure becomes invisible the moment you're congratulated
They're not celebrating writing the check. They're nervous.
"Daddy. Daddy."
The problem was never the pressure. It was having nowhere to put it down.
I forgot how to speak Dutch
What has your career cost you that you didn't notice until it was gone?
The decision that sat for six months
Lack of information was never the problem.
Read →The person running the room doesn't get their turn
A pattern that's been bothering me for months.
Read →Nobody tells you about the lonely part
You're not the only one.
Read →You can't fake it for too long
The problem with "fake it till you make it."
Read →The question nobody at this level asks out loud
It's not a confidence problem. It's a structural one.
Read →Most leaders test everyone except themselves
He tested his whole leadership team. Then he took it himself.
Read →What actually happens at the end of an Inner Circles cycle
The honesty is the hard part.
Read →Why giving feedback teaches you more than receiving it
Most people think the hot seat is the product. It's not.
Read →What we learned running a NED event for 40 iGaming leaders
Board-seat pathways in iGaming operate like a black box. We tried to open it up.
Read →