Are You Leaving Millions on the Table? 5 Little-Known Negotiation Secrets to Maximize Payday
These five negotiation secrets can help you avoid costly mistakes, strengthen your position and walk away with millions more when selling your first business.
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Key Takeaways
- Understand your BATNA and WATNA to set your negotiation boundaries and retain power during talks.
- Establish and justify a high initial price to anchor the subsequent negotiation discussions in your favor.
- Focus beyond the headline price by negotiating deal structure, using contingent concessions and maintaining emotional control for the best possible terms.
You did it. You turned that wild, half-impossible idea into an actual company. You survived the chaos, the bad coffee, the endless nights and the times when quitting looked easier. And now, someone wants to buy it. Big moment. Selling your first business isn’t just another transaction — it’s probably the biggest financial deal you’ll ever make. It’s thrilling, but also quietly dangerous. Many first-time founders walk away thinking they did great, when in reality, they left a few million sitting on the table.
If you ask me, selling is not luck. It’s a negotiation game. And the buyer likely does this often — they know the playbook. So, you need yours too. Use my five negotiation secrets, and you’ll walk away with profit in your hands.
1. Do your homework: Know your BATNA and WATNA
Before you discuss price, you must know your BATNA and WATNA. But what are these?
BATNA stands for Best Alternative To a Negotiated Agreement.
WATNA is the Worst Alternative To a Negotiated Agreement. These are your safety net and your worst-case scenario.
Your BATNA is your plan B. If this deal falls apart, what will you do? Maybe you have a second-best buyer waiting. Maybe you’ll keep running the business for another year to boost revenue. Having this gives you power. If you know you have a solid Plan B, you won’t accept a bad offer and, of course, stay confident.
Your WATNA is the worst outcome you can live with. It’s your absolute “walk-away” number and terms. You should never, ever accept a deal worse than your WATNA. Knowing these two points is like having a map in a dark forest. It tells you where you can go and where you absolutely cannot. Do the research well and talk clearly to your advisors.
2. Anchor high and justify your number
The first number mentioned in a negotiation acts like an anchor, because every other price discussed will be compared to it. This is a psychological trick. You, the seller, should almost always drop the first number. Why? You want to set the anchor. You want that first, high price to be the starting point in the buyer’s mind.
Don’t be afraid to be ambitious. Throw down a strong, high number. But keep in mind, it needs to be reasonable. An outrageously high number makes you look unserious. But a well-justified high anchor gives you room to negotiate down, for sure. When you present your price, back it up with a clear, compelling story.
Don’t just say, “The price is $X million.”
Say, “Based on our 30% growth forecast, our repeat customer rate and our IP position, the valuation is $8 million.”
If you use a POS (Point of Sale) software for your retail business, you have a goldmine of data. Don’t rely on tax returns only. Use your POS reports — the ones showing daily sales, inventory turnover, customer purchase habits and even employee performance — to back up your financial claims.
Here, you are not just naming a price. You are detailing the value. This makes your high number feel solid. Now the entire discussion is in your favor right from the start.
3. The price isn’t everything: Negotiate the structure
First-time sellers obsess over the total price. That’s a mistake. The deal structure is often where millions are gained or lost. Remember, the buyer is trying to minimize risk. You should think about more than just cash up front.
Look at things like:
- Earn-outs: This means you get a lower amount now, and more later, based on how the company performs after the sale. It’s common. Be careful — the buyer now controls the company. They might make decisions that make your earn-out impossible to hit. Negotiate clear, achievable metrics for any earn-out. Make sure you have some visibility.
- Warranties and indemnities: These are promises you make about the business being clean and healthy. If the buyer finds a problem later, they can claw back part of the purchase price. Limit these as much as possible. Set a cap on how much they can claw back. Shorten the time limit for making claims.
- Rollover equity: Sometimes, the buyer wants you to keep some ownership in the new, merged company. This ties your financial future to theirs. Negotiate a clear exit strategy for this equity.
You can often win big concessions on these terms without changing the headline price. Be flexible on the structure, but make sure you stay strategic about the risk. A slightly lower price with cleaner terms can be worth much more than a high price with massive risk.
4. Trade, don’t give in — use contingent concessions
Every time the buyer asks for a discount, an extra term or a longer indemnity period, you must ask for something in return.
Think of it like this: “I can agree to lower the price by $100,000 if you agree to a 30-day closing period instead of 60 days.”
This is a contingent concession. Your agreement is contingent upon their movement. It protects your value. It shows the buyer you are a serious negotiator. You’re not being difficult — just being fair. You just created a win-win situation, congrats!
5. Manage your emotions and use silence as power
Selling your first company is personal. It’s your baby. The buyer knows this well. Which is why they will use your emotional attachment against you. They might criticize the business. Your job is to stay cool. My best tip for today will be to check your ego and emotions at the door. You should know that this is a business transaction, nothing else.
If a buyer makes an aggressive offer or a harsh comment, your best tactic is often silence. Don’t jump to defend or accept. Let the uncomfortable silence hang in the air. People hate silence. Often, the buyer will rush to fill the void. They might lower their price or give away a crucial piece of information. Silence is a powerful negotiating tool.
Also, never forget the power of the team. You should have an attorney and an M&A advisor. When the buyer pushes hard, you can use your team as a shield.
Say, “That’s an interesting point, but I need to consult with my tax advisor on the implications of that term.” This gives you time to think clearly. It shows you have a professional, objective process and that you are a strategic player.
Following these secrets won’t just get the deal done — they will help you close a deal that truly reflects your incredible success. You earned those millions. Now go get them!
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Key Takeaways
- Understand your BATNA and WATNA to set your negotiation boundaries and retain power during talks.
- Establish and justify a high initial price to anchor the subsequent negotiation discussions in your favor.
- Focus beyond the headline price by negotiating deal structure, using contingent concessions and maintaining emotional control for the best possible terms.
You did it. You turned that wild, half-impossible idea into an actual company. You survived the chaos, the bad coffee, the endless nights and the times when quitting looked easier. And now, someone wants to buy it. Big moment. Selling your first business isn’t just another transaction — it’s probably the biggest financial deal you’ll ever make. It’s thrilling, but also quietly dangerous. Many first-time founders walk away thinking they did great, when in reality, they left a few million sitting on the table.
If you ask me, selling is not luck. It’s a negotiation game. And the buyer likely does this often — they know the playbook. So, you need yours too. Use my five negotiation secrets, and you’ll walk away with profit in your hands.