When negotiating, play the long game.
When it comes to deal-making and negotiating, setting the price on a service or product that hasn’t been priced in the market can be challenging. Usually, I advise against making the first offer.
As grandpa used to say, “Never negotiate against yourself.” Let the other side sweat it out and show their cards. However, sometimes you have to make the first offer to get the negotiation going.
Some people might believe that setting the price is a data science project. Except science and data will only get you so far when you’re looking someone in the eye across the table. Negotiating is more of an art.
As a talent agent, media attorney, and professor at USC Gould School of Law, I teach my students and clients strategies how to price their deals in negotiations. My new book, TILT the Room, is also coming out in 2026, which explains how you can use timing, influence,
Here are four strategies I use when negotiating a price.
1. Do the biggest possible deal that you can.
The reality about deals is that it takes the same amount of time to negotiate small ones as it takes to negotiate big ones. So negotiate the biggest deal possible when the other side is in the room. Otherwise, you’ll have to keep coming back to negotiate, causing yourself and your customer or client more work.
2. The biggest number isn’t always the best deal.
When negotiating, play the long game. Avoid the urge to get the largest number on one deal when the real win is more money over the long term.
I learned this while working in Hollywood as a teenager. I worked for producers including Eric Bruckner, Peter Davis, and Peter Guber. They let me tag along as long as I dressed nicely and didn’t make a fool of myself.
For them, the biggest number wasn’t always the best deal. It was about revenue streams down the line. Profit sharing. In the venture capital world, they call this “smart money—not just a check.”
3. Negotiate a better offer by playing the field.
A while back, I was involved in selling Element to Billabong. The problem was that the negotiated offer price from Billabong was too low.
If you want to get a better offer, sometimes you need to play the field. After my group got Vans interested, Vans made a great offer. Once Billabong heard about it, it came to the table quickly and increased its offer.
4. Keep your sense of humor in the negotiation process.
Sometimes pricing can come back to bite you in the butt, despite your best efforts. One time, my business partner, Jeff Montgomery, and I looked at purchasing a publicly listed company that had underperforming assets. Together, we scoured the underperforming companies on the Pink Sheet OTC market. The goal was a “respectable” stock price over 10 cents, a company with some real estate holdings, and some upside on annual revenue growth.
The best company turned out to be an old magazine, Girls’ Life. At the time, Girls’ Life was a public company, had a subscriber base, and owned a themed restaurant property. It was looking for something in the region of $7 million. My partner and I negotiated for a while, letting it know the offer was pending. Then, we sent our offer package at $2 million with all the justifications and reasons why the offer was reasonable.
I guarantee the reasons sounded really good. Apparently, they weren’t good enough for Girls’ Life. Their board sent my partner and me a letter via FedEx that said simply:
Dear Messrs. Montgomery and Sterling,
The Board of Directors of Girls’ Life, Inc. will not be proceeding with further negotiations with your firm.
Sincerely, Girls’ Life, Inc.
P.S. We don’t know what you’re smoking out there in California. It must be good.
When negotiating, remember setting a price is often more art than science. Think about the long-term and have a sense of humor about the process.
This article was originally published by Inc. March 14, 2026.