Looking over the rules, it still seems like the billboard business would qualify though we are lacking detail about how the seed money may be allocated. Clearly some of it could go toward salaries. That makes the shoe shine business viable.

Hey Joe Parking-Lot-Owner, I will pay you $5000 for exclusive rights to park my billboard trailer in your lot for one day if you agree to rent my billboard for $4900 (wink wink).

Presto, $4900 in revenue and all I have to do is sit around with a sign on my trailer for a day.

Are there published rules other than what Donald said on the show? I saw rules for each task in season one but nothing since then.

Looking at the show again, it sounds like Donald specifically says “a service” business. That probably disqualifies reselling electronics, but moving furniture and transporting people is certainly a service. A hot dog cart is arguably a food prep service.

How about a shoe shine business? This is what Craig does for a living so I’m surprised it didn’t come up. Using my $5000, I’d hire 50 guys at $10/hour to shine shoes at $1/pair (an easy sell). Each shiner only needs to average 1 customer every 20 minutes to gross $1200 over 8 hours and win the task handily even though I’d be losing money by the minute.

How about “Shine & Dine”? Sell a $5 shoe shine and provide complimentary bagel & coffee or pizza & soda while they wait. Park the trailer in front of a deli and get permission to give away a shine with every bagel purchase as long as they process the sale through your business. What deli wouldn’t love that? Their customers get free shines (if they want them) and you get credit for every one of their sales.