As an entrepreneur, your most valuable asset isn’t your product, your office, or even your team. It’s your time.

And yet, we’ve been conditioned to waste it. We stand in security lines, wait at crowded gates, and lose entire days to travel all in the name of saving money. We look at private aviation as the ultimate symbol of making it,  a luxury reserved for billionaires and rock stars.

We see it as an expense.

But what if we’re wrong? What if it’s a tool? What if the most successful, efficient leaders aren’t using it for luxury, but for leverage? And what if there was a way to access this tool the ability to be in three cities in one day for 50, 60, or even 75 percent off the retail price?

This isn’t a gimmick. It’s the single biggest insider secret in the aviation industry. It’s a strategy built on information, not just wealth. And for the agile entrepreneur, it’s a game-changer.

The $10 Billion Dollar Secret: What ‘Empty Leg’ Actually Means

To understand the opportunity, you first have to understand the industry’s biggest inefficiency.

Private jets are chartered for one-way trips all the time. A CEO in Toronto needs to fly to a meeting in Miami. A family flies from New York to Aspen for a ski trip. The jet flies its passengers, drops them off… and now it’s stuck in Miami or Aspen.

But the jet’s home base, where its crew lives, and where its hangar is might be back in Toronto or Teterboro. The operator must fly that multi-million dollar aircraft back to its home base, and they have to do it without any passengers.

This is called a ferry flight or, more commonly, an empty leg flights.

For the operator, this is a pure loss. They are burning thousands of dollars in fuel, paying crew salaries, and putting flight hours on the engines, all for zero revenue.

And this is where the smart entrepreneur comes in.

The operator would rather sell that empty flight for something than nothing. They will offer these flights at a massive discount, often 50% to 75% off the standard charter rate just to cover their costs.

You aren’t just buying a cheap flight. You are solving the operator’s high-stakes financial problem. In return, you get to fly on some of the best executive jets in the world, for a price that is often competitive with last-minute, first-class commercial tickets.

The Myth of ‘Cost’ vs. The Reality of ‘Value’

Let’s be clear: this strategy still isn’t cheap.  But for a business owner,  cheap is the wrong metric. The right metric is value. 

A $15,000 charter flight for a team of four looks expensive on a spreadsheet. But let’s break down the real cost of the cheaper commercial alternative.

The ‘Commercial’ Cost (A Case Study in Lost Time)

Let’s say you and three of your top executives from Mississauga need to visit key partners in Chicago, Nashville, and then New York.

• Day 1: Morning travel to Chicago. 2 PM meeting. Hotel.
• Day 2: Morning flight to Nashville. 3 PM meeting. Hotel.
• Day 3: Morning flight to NYC. 2 PM meeting. Hotel.
• Day 4: Morning flight back to Toronto.

The Hard Costs:

• 4 x $1,500 (multi-city, last-minute business class) = $6,000
• 3 x 4 hotel rooms ($300/night) = $3,600
• Meals, Ubers, expenses = $2,000
• Total Cash Outlay: $11,600

The Real Cost:

• You lost four full business days for three meetings.
• Your four highest-value employees (including you) were out of the office, unable to do deep work, manage their teams, or close other deals. The opportunity cost is staggering.

The ‘Empty Leg’ Value

Now, you find an empty leg on a midsize jet (like a Citation or Challenger) flying from Toronto to Chicago. You book it for your team. From there, you find another empty leg to Nashville, and a third to Teterboro (NYC).

• Day 1:
  • 7 AM: Arrive at the private terminal (15 mins before flight).
  • 8 AM: Wheels up to Chicago. You hold your pre-meeting on the plane.
  • 10 AM: Land in Chicago. Meeting at 11 AM.
  • 2 PM: Wheels up to Nashville. You debrief and prep for the next meeting on the plane.
  • 4 PM: Land in Nashville. Meeting at 5 PM.
  • 8 PM: Wheels up to Teterboro.
  • 10:30 PM: Land in Teterboro. Hotel.

The Hard Costs:

• 3 x Empty Leg Flights (Total) = ~$20,000 – $25,000
• 1 Night Hotel = $1,200
• Total Cash Outlay: ~$26,200

It looks more expensive. But you just bought back three full business days for your four most valuable people. You turned four days of chaos into one hyper-productive surgical strike. 

The $14,600 difference wasn’t an expense; it was an investment in speed, efficiency, and productivity. That is a strategic weapon.

This Isn’t a Shortcut, It’s a System: The 4 Rules of Empty Leg Hunting

This massive opportunity comes with one major trade-off, and it’s the reason this isn’t for everyone.

You must be flexible.

With a normal charter, you set the schedule, the destination, and the aircraft. With an empty leg, the aircraft sets the terms. You are simply filling a seat that would otherwise be empty.

This strategy only works if you follow these four rules.

Rule 1: You Can’t Control the Schedule

The flight leaves when the operator needs it to leave. It might be at 8:15 AM on a Tuesday or 9:43 PM on a Saturday. If you have a must-not-be-late 9 AM board meeting, this is not the strategy for you. This is for the opportunity the client you’ve been meaning to visit, the team retreat you’ve been planning.

Rule 2: You Cannot Control the Destination

Empty legs are fixed, one-way routes. You can’t book an empty leg from Toronto to Miami if the plane is flying from Toronto to Teterboro. You have to be looking for flights to Teterboro. This requires an opportunity mindset (e.g.,  Where can I go this week? ) rather than a demand mindset ( I must go to Miami ).

Rule 3: It Is (Almost Always) a One-Way Trip

The $10,000 deal gets you to your destination. It does not get you back. You are responsible for your return flight, which could be another empty leg (if you’re lucky), a standard charter, or a commercial flight.

Rule 4: You Must Be Ready to Move

The best deals are often last-minute. An operator may not know a flight will be empty until 24-48 hours beforehand. This is a strategy for agile entrepreneurs who can pack a bag and seize an opportunity, not for those who need to plan a month in advance.

How to Find and Book These  Off-Market  Flights

You won’t find these on Google Flights or Expedia. You have to know where to look.

• Charter Broker Relationships: This is, by far, the most effective way. Build a relationship with a reputable charter broker. Tell them your home airport (e.g., Pearson or Billy Bishop) and the destinations you’re interested in. They have the inside fleet knowledge. When a flight matching your profile pops up, they will call you first. They do the hunting for you.
• Subscription Apps & Marketplaces: There are several apps and fly-by-the-seat marketplaces dedicated to listing public empty legs. These are great for seeing what’s out there, but be aware that the best deals are often sourced through brokers before they ever hit a public app.
• Operator  Mailing Lists: Many charter operators maintain a private email list for their available empty legs. You can sign up, and you’ll often get a daily or weekly list of available flights.

This isn’t about luxury; it’s about intelligence. It’s about understanding that for those rigid, must-be-there meetings, you still need to book one of the best executive jets on your own schedule. But for everything else, this is your unfair advantage.

Conclusion: The Real Definition of ‘Affordable’

For decades, we’ve been taught that success means buying luxury. But the new generation of entrepreneurs knows that success means buying time.

The empty leg flight is the ultimate tool for this. It reframes private aviation from an unattainable status symbol into a smart, accessible productivity tool. It proves that the best choice isn’t always the most expensive one, but the most strategic one.

It’s not about being a billionaire. It’s about thinking like one and using your agility and information to beat them at their own game.

Explore how you can apply these insights.