The fail state is triggered when the following is true:

• you have less than or equal to $2 left in your account
  
• you have zero cards to sell (neither in the store nor the inventory)
  
• there's no incoming mail, no matter what's inside

No other conditions are relevant.

To have the shop fail around turn 11 I have devised a strategy that should more or less work every time, but as some parts of it are random you might end up being a day or so late. In the end this doesn't matter as all that changes is the dialogue.

First of all you'll have to click through all the dialogue again, of course. Once you can actually sell cards only put up those that are either scratched or a duplicate of another card in your collection.

You'll want to end up with only mint cards and only exactly one of each.

Now go on GBay and buy mint cards you don't already have. Your goal is to reach a balance of either between $12 and $14 or $7 and $9.

Don't put any of the mint, non-duplicate cards up for sale!

Once Declan (the union rep) comes along and unlocks decorations go to GBay again and buy a decoration for either $10 (if you have between $12 and $14) or $5 (if you have between $7 and $9). The $5 decoration isn't always there so check back the next day if needed. This should bring you to $2 or lower.

Just skip through the days without selling anything. Brush off any customers wanting to buy cards from you directly and don't sell anything over the phone either.

On day 10 you'll unlock the card binder. Put all cards you still own into the binder. You now should have $2 or less and no cards left to sell.

Finish the day and the next day pick up the phone to unlock the achievement.

If you've followed my little guide so far you should now have unlocked the "The Big Bogan" achievement. As said, since some elements of the game are random you might not make it on day 11 as I did but you should come close.

Thanks for reading!

Here's an uncut video of a full run until the achievement would unlock (I already got it so it's obviously not unlocking again):