Weekend Edition / Dear Ohad...

Sam spends $600K a year on cards but his points were just sitting there. What if he could use points to close deals, impress vendors, and accelerate contracts without touching cash? Here’s how businesses turns points into silent negotiation power.

Weekend Edition / Dear Ohad...
📸: Taking your questions during a layover @ Chicago's O'hare (ORD) • where the United ad says “we're going everywhere,” but leaves out whether "we’ll actually leave on time" • Government Shutdown Galore
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Hey Ohad, I’m Sam from Denver.

My partner and I run a small IT consulting firm and we spend about $600K a year on credit cards.

I never thought about it, but someone mentioned that points could be used as negotiation leverage with clients or vendors - like, “we can fly your execs to meet us at no cash cost.”

Is that real? How would you actually do that without just burning points on personal travel?

Thanks!

Dear Sam,

Yes - this isn’t hype. Your points & miles are your silent profit, a lever few business owners even know exists. Most owners treat points like a perk; the smart ones treat them like ROI-driving currency.

Here’s how you actually make it work 👇🏻

Step 1: Identify Strategic Moments

Look for opportunities where a points-funded experience creates outsized value for the other party. The goal isn’t to “buy” them - it’s to accelerate decisions or unlock perks they value highly.

Think: key client meetings, vendor onboarding, or retention incentives.

Step 2: Pick the Right Experiences

  • Flight upgrades or award seats to meet you in person
  • Hotel stays for a client visiting your office
  • Conference passes or high-value travel experiences tied to business outcomes

Step 3: Layer the ROI Math

If a meeting brings $50K in new business and you spend 50K points to fly someone roundtrip in economy or premium economy, your effective ROI is massive - points replace cash that would otherwise come out of your profit line. Even better, if your team can combine points from Chase, Amex, or other programs, you can stack returns without extra cost.

Step 4: Execute Tactically

  • Book award travel well in advance; confirm availability before making promises.
  • Only use points where the upside is clear (new deal, contract renewal, vendor incentive).
  • Track points spent and assign a “revenue equivalent” so you know your real ROI.

Example Play

Sam, say you’re negotiating a $100K contract with a vendor. Offering to fly their execs to your HQ using points costs 40K points per person (~$500 value), they arrive impressed, deal closes. You spent points, saved cash, and gained $100K revenue. That’s leverage in its purest form.

Bottom Line

Points aren’t just for personal travel - they’re strategic currency. SMBs who use them this way increase closing rates, deepen relationships, and turn routine spend into measurable ROI.

-- Ohad