Stop Giving Sh*t Away for Free

Founders Who Make Money Make Great Founders

Author

Gregory Kennedy
July 07, 2025

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Live Presentation and Q&A with Gregory Kennedy and Alexander Shartsis, Entrepreneur and early-stage Startup Advisor.

Broadcasting live on July 30th from 9:00 AM to 10:30 AM Pacific Time.

Stop Giving Sh*t Away for Free

Someone asked me to recommend a Google Analytics alternative, and I suggested a low-cost MMM or incrementality platform, such as Haus.io, for advertising measurement. And maybe Heap or Mixpannel for link tracking.

They then qualified their request, stating that they were looking for free options. To which I replied, “The freemium era of the internet is over.”

How do I know this? Well, I now pay:

575.88/year for LinkedIn.

$395/year for X.

$240/year for ChatGPT.

$420.69/year for Memelord Technology, and when I find out what it does, Jason Levin will have to kill me.

Plus, I pay for a ton of other apps like Claude, Canva, Google Workspace, Squarespace, Slack, and I am still in the free tier for Beehiiv, but not for long.

I have been recommending for a while that founders should avoid freemium and wanted to spell this out in my newsletter: Startups need to stop giving away free sh*t.

Everyone is charging now, and you should too.

Free Trials Beat Freemium Every Time, Here's Why

Free trials, of course, are the only “free” that pull their weight.

Freemium is expensive, and many never convert. It increases support costs and steers your feature set in a direction that may not align with the needs of paying users.

But free trials give them an opportunity to try before they buy.

I sign up for free trials all the time, and if they expire before I get a chance to test it. Many times, I go back and pay for a month of service. If I don’t like it, I cancel.

The decision-making math of free trials:

  • 7 to 14 days = creates urgency

  • Full product access = you get better feedback

  • Clear deadline = get them to make a decision

Users try it, see the value, and either pay or bounce. There is no ambiguity. You learn who’s serious and who just wanted to kick tires and waste your time.

Now compare that to freemium:

  • Unlimited time = no urgency

  • Gated features = value prop is unclear

  • No end date = “I’m busy bro, maybe later”

Freemium invites indecision, and you end up optimizing for user count, not revenue. But the real challenge is when you finally ask them to pay, they’re like, “Wait, this wasn’t free forever?”

Don’t trick people into loving the free version and resenting the paid one. Make it clear: you’re running a business, not a public sandbox.

This applies to consulting services or any other internet business.

The Only Times "Free" Actually Works

Sure, not everything should be locked behind a paywall. There are cases where “free” works. But only when it serves the paid version.

Free makes sense when:

  • You’re building lead magnet apps (apps are the new content)

  • You’re building an audience that you’ll monetize later, like a newsletter

  • You’re ChatGPT and have access to unlimited funding

But even in those cases. Free is a means to an end. Paid is the product. The moment “free” becomes your value prop, you’ve lost. You're doing charity work and pretending it's strategy.

Freemium is Also Killing Enterprise Pilots

You don’t want pilots to drag on for months. It’s the kiss of death.

A 30-day free trial to help create urgency.

You can also use paid POCs as a filter. Not to block deals, but to force seriousness. If they can’t commit $5K to validate a product, will they spend six figures?

I prefer a tightly managed free trial period, followed by negotiation of the price at the end. This gives the startup maximum leverage in the contract negotiation because no price anchor has been set.

(Negotiation strategy is out of scope for this post, but it’s my all-time favorite topic. I will revisit this at another time.)

Whatever you do, you want to avoid at all costs is the endless POC where:

  • The decision-maker leaving

  • Your budget vanishing

  • The timeline slipping

  • And you get ghosted by some other VP with zero authority

Utilizing a free trial to expedite deal closure is crucial in enterprise sales.

Founders Who Make Money Make Great Founders

Founders often claim they’re “optimizing for growth,” but more often than not, they’re avoiding the tough stuff: pricing, positioning, and prioritization.

Freemium delays those decisions. It gives you users, sure. But not urgency, not revenue, and definitely not focus.

Free trials? They work.

They create a moment of truth. A defined window where users either see the value or move on. You get feedback that matters, not feature requests from people who treat your product like a hobby. And in enterprise, a tightly scoped trial beats a never-ending pilot every time. It keeps deals moving, forces clarity, and gives you leverage when it’s time to talk money.

You can give things away, but only when there’s a clear path to getting paid.

Free should be a strategy, not a default.

No Gregory and Paul Show on July 4th

On the Gregory and Paul Show, we break down the latest in startups, SaaS, AI, and whatever the internet is debating this week. But not this time. No live stream. We took a well-deserved break.

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But it’s still significantly less than you’ll spend on a failed Google or Facebook ad campaign.

The rumors are all true. I’m on a mission to help as many founders as I can monetize and grow their startups. I created Vibe Corps for bootstrappers and pre-seed startups who need expert-level support without the expert-level price tag.

Ok, so what do you get?

  • My standard 3-month marketing playbook for SaaS startups, plus all my battle-tested templates and frameworks.

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Together, we will define your ICP (Ideal Customer Profile). Build your first real marketing plan, and launch a campaign that actually drives leads.

Stop wasting months “planning” without results. If you’re serious about growing your startup, join the Vibe Corps.

The People’s VBMRKTR

I'm Gregory Kennedy, former creative director, 3x head of marketing, and founder of Vibe Your SaaS. I help early-stage startups build real momentum with strategic clarity, AI-driven execution, and zero BS.

Greogry Kennedy // Vibe Your SaaS // www.vbmrktr.com