Get the Story Right or Die Trying with J Ryan Williams

J Ryan Williams spent years leading sales at high-growth startups. Then he quit. Not because he lost faith in sales, but because he realized most founders were doing it backwards.

They’d try to “sell” without a story. Ship product without clear positioning. Pitch VCs, customers, and candidates with the same fuzzy language that made everything harder downstream.

The real work, he realized, wasn’t in fixing the funnel. It was upstream, in clarifying the message that drives everything else. 

“Getting the story right is more important than getting the first customer.” 

If your sales motion is struggling, start by rewriting your story.

Skip the Deck. Say What You Actually Do.

Polished decks don’t create clarity. They hide that most founders can’t explain their value in one sentence.

Want a test? Say it out loud, without the buzzwords, without the pitch voice. Can your cofounder repeat it? Can your customers?

If not, that’s the bottleneck.

Stop Trying to Sell a Product No One Understands

Most early-stage sales problems aren’t sales problems. They’re narrative problems.

You’re not converting because people don’t know what you’re discussing. You’re not getting inbound because no one remembers what you do.

Before blaming the SDRs or the CTA, ensure the message isn’t broken.

The Hidden Cost of Growing Too Fast

What happens when your product takes off before it’s ready? Collin Stewart lived that story. Carb.io went from $0 to $1M in three months. But beneath the surface, things were breaking, slowly, then all at once.

The backend was held together with duct tape. Emails were queued for weeks. AWS bills ballooned. Feature requests piled up while foundational issues stayed broken.

And still, the team pushed to close more deals.

“I was chasing growth, not quality. We were scaling pain.”

Founders often think that more revenue will solve the problem. It doesn’t. It magnifies it. Growth compounds, but so do tech debt and churn.

If your product isn’t ready to scale, adding more customers just means more people experience your failure.

Rewrite Sooner. Or Pay Later

Early on, Collin’s CTO proposed a full rewrite. It would’ve slowed things down. Collin said no. In hindsight, that single choice cascaded into lost customers, failed feature launches, and a dev team constantly underwater.

Speed feels right in the moment. But there’s no shortcut around infrastructure that can’t support your roadmap. You’re not saving time if you’re duct-taping features onto a system that can’t handle the next 10 customers, let alone 100. You’re setting a time bomb.

“The rebuild felt too slow. But not rebuilding made everything else slower.”

Customers Don’t Buy Features. They Buy Outcomes

Even when Carb’s product was shaky, its messaging worked. Why? Because it spoke directly to what customers actually cared about.

Hotel GMs didn’t care about lead scoring. They cared about TripAdvisor rankings. So, Carb built campaigns around that, emails that said, “You’re ranked 4th in Napa. Want to be #1?”

That hit where it counted: ego, performance reviews, and revenue.

“We sold the outcome. And it worked.”

This isn’t just a copywriting tip. It’s a product insight. If you know what metric your buyer lives and dies by, you know what your product has to move.

Prospecting Isn’t About Volume. It’s About Context.

The Carb team’s best results came from custom data, not generic lists. They researched each hotel’s ownership group, customer experience score, and competitive position.

That level of context lets them prioritize leads, personalize messaging, and sidestep generic pitches entirely.

That work and its process later became the basis for J. Ryan’s team at LeadGenius.

If you’re still prospecting like it’s 2015, you’re doing it wrong. Personalization isn’t just “first name” tokens. It’s a signal-driven strategy.

Let Your Team Buy Before They Sell

When J. Ryan ran a sales tech evaluation, he didn’t own the process. He let his SDRs run everything from research to demo to recommendation.

That changed how they sold.

When a rep has felt the pain of being sold to, the bad follow-up, the irrelevant pitch, the clunky onboarding, they sell differently.

“A 23-year-old cold caller suddenly knew what it meant to control a $50K budget. That changed everything.”

Founders: After hearing more enablement slides, your team will never improve at selling. Give them ownership of the buyer’s side of the table.

Selling to Startups? You’re Building on Sand

One of the most brutal truths in early-stage SaaS: selling to other startups can feel like traction, but it’s often just noise.

Startups are easy wins. They’re friendly, curious, optimistic, and often desperate for solutions. But they churn just as fast as they buy. Budgets disappear. Priorities shift. Your internal champion changes jobs.

Ryan put it best: “Startups selling to startups are just drunks holding each other up at a party.”

It’s funny because it’s true, and dangerous. Especially if you start making decisions based on this feedback loop. Friendly deals make you think you’ve nailed product-market fit, so you ramp up go-to-market too early. The numbers look good, but the social network effect of your founder circles inflates them.

Collin adds the punch: “If product-market fit is weak, it doesn’t matter how good your go-to-market strategy is. You’re scaling something that doesn’t work.”

Before you hire, spend, or scale, ask: would a stranger buy this at full price, with their own money, without me hand-holding them?

Product-Market Fit Isn’t Binary. It’s a Stack of Proofs.

PMF isn’t a flag you raise when you hit $1M ARR. It’s a body of evidence, built deal by deal, layer by layer.

Founders often chase “PMF” like it’s a one-and-done milestone. But J. Ryan breaks it down like a geometric proof: a series of things that must be true.

• Will anyone buy it, even for $1?
• Will they buy it at the price that makes the business viable?
• Can you repeat that with five customers who look the same?
• Can you win deals without being in the room?
• Can you sell into a new vertical and train someone else to do the same?

Every one of those is a milestone, not a checkbox. The more hands (i.e., consistent buyer configurations) you can identify and sell into, the stronger your foundation gets.

This lens turns PMF into something practical and measurable, not a vague gut feeling.

Want Better Sales Data? Build Better Sales Experiments.

Most “product-market fit” problems are actually experimentation problems. Founders confuse wins with validation. They build on weak signals. Or worse, ignore the sales patterns staring them in the face.

Ryan drops a sharp standard for vetting deals: “If you don’t know the full buying committee, don’t put it in your CRM.” He saw it firsthand in the hotel vertical. Every real deal included three key players:

• The VP of Marketing.
• The Director of Sales.
• The Head of RevOps.

No matter how excited one of them was, the deal wasn’t real without all three. And that insight only came from running clear, replicable sales plays and documenting what worked.

Most founders say they want product-market fit. But what they need first is sales discipline:

• Define your “winning hand.”
• Run the same play 10 times.
• Track every signal that repeats.

Only then can you confidently scale what works or pivot with clarity.

You Don’t Just “Find” Product-Market Fit. You Strengthen It

Founders are often told, “Just get out and sell more.” But blind selling doesn’t help you find product-market fit. It hides how weak it actually is.

Instead of chasing revenue, chase repeatability. As Collin puts it, PMF isn’t binary. It’s a muscle. And the way to strengthen it is by obsessing over the full buying journey:

• Who’s actually involved in the decision?
• What do they value?
• How does your product directly map to those values?

You don’t need a giant market. You need a clear pattern.

If you can consistently close hotel GMs by tying your solution to their TripAdvisor score, you’ve got a strong signal. That’s better than a dozen one-off wins with no common thread.

The test is simple: Can you say out loud, with confidence, “I know how to sell to [X]”? If not, you’re not done yet.

Speak Like an Insider or Get Ignored

Want your message to land? Stop chasing virality. Start speaking your customers’ language.

One of the most underrated unlocks in go-to-market is language fit. Not just knowing your ICP but also sounding like them. Insiders have a shorthand. Outsiders don’t get the callback.

Ryan illustrates this beautifully with a story from the yoga world. When a guy asked his friend about her practice, she immediately recognized him as one of “us.” That single word signaled trust, relevance, and community, more than any polished pitch ever could.

In B2B, the same principle applies. 

If your prospect hears language “for them, by them,” it quickly breaks down resistance. Your cold video doesn’t need 10,000 views. It needs 10 right people to feel like you get them.

So instead of asking, “How do I sell this?” Ask: “What do my best customers already say about this problem. And how can I say it like they do?”

Building Trust with Video Starts with Getting Out of Your Own Way

Most founders overthink video. They assume it’s about gear, scripts, and polish. But the real barrier isn’t technical. It’s internal.

That’s what Collin ran into when trying to distill a chapter of his book into a short-form video with J Ryan. Even with the right tools (teleprompter, ChatGPT, a clear thesis), it was hard, not because the message wasn’t good, but because the format forced clarity. Fluff dies fast on camera. You either hit the point or you don’t.

This is where most founder content breaks: it sounds thoughtful but lands flat. Why? Because the hook is off, the message rambles, or the angle doesn’t connect with the people you’re trying to help.

What Great Founder Content Actually Takes

J Ryan’s approach with ANTEATER isn’t about making “content.” It’s about packaging real founder insight in a valuable and trustworthy way. The bar is high:

• Clarity on your audience’s actual problems.
• Language that makes you sound like one of them (not a keynote speaker).
• A story that ties your credibility to their pain.

You don’t need a viral hit. You need a video that makes 10 people say, “Finally, someone gets it.”

Why Founder-Led Video Beats Branding, Ads, and Even Books

You could wait to get on the conference stage. You could write a book and spend 18 months editing. You could pay an agency to run brand ads with abstract messaging. All of these can work, eventually.

But none of them let you show up in your buyer’s feed tomorrow saying, “Hey, I get your problem. Here’s what to do next.”

That’s what short-form founder video enables. Done right, it’s the fastest way to build trust at scale:

• Show you understand the problem.
• Share a unique perspective.
• Speak your buyer’s language.
• Repeat.

As J Ryan puts it: if you don’t tell your story, your prospects are left guessing. They’ll assume you’re just another no-name brand. And default to the louder one with a logo they recognize.

So, whether it’s an SDR tip, a product insight, or the reason you started the company… say it out loud, on camera, like a human.

If it’s working, keep going. If not, fix the message, not the medium.

Conclusion

If people don’t get what you do, they won’t buy, click, or care.

Fix the story before you hire, scale, or ship another feature. No one else will if you can’t say what you do in one sentence.

Product-market fit starts with message-market fit. Say it simply. Say it like an insider. Say it on camera. Then watch everything else get easier.

Ready to tell your founder story like a pro? Talk to J Ryan and start turning insight into a video that actually lands.

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