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Two guys leave a company to start their own thing

One is a brilliant Sr. engineer
Built products for 10 years
Never had to sell anything in his life

The other is a sales rep
Spent his career talking to buyers
Never built a product in his life

Fast forward 6 months....

The engineer has an insanely great product
Real inbound demand
But now he needs to learn how to close it

The sales rep has a solid product-
It's not as technically sharp
But he knows how to promote and sell

The barrier to building has never been lower

The barrier to selling is still just as high

Learn to sell

A study of 8,000 workers found employees at companies founded after 2015 work from home nearly twice as often as those at pre-1990 firms. As Boomer and Gen X bosses retire, researchers say today's RTO mandates are just a temporary blip.

My take: Shoutout to science for confirming what we all already knew. Tech and AI companies are going remote. Blue-collar and boomer businesses aren't. That's it. That's the whole debate. Pick your lane.

Monaco is an AI-native CRM that bundles prospecting, outreach, and deal management into one platform. They pair AI agents with real salespeople to save time and improve win rates.

My take: The best seller will use AI to handle the routine stuff - then reinvest that time into trust, influence, and negotiation. The gap between real sellers and order-takers is about to get a lot more obvious.

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Stop cold calling people who don't want to hear from you. Start interviewing people who are dying to talk about themselves.

Here's the play: reach out to prospects and offer to feature them in a marketing asset. A blog post, "State of [Industry]" report, even a newsletter. You're not pitching - you're offering free marketing. Executives who'd never take a cold call will happily give you 30 minutes when you're asking for their expertise.

That 30-minute conversation does three things:

1. It builds your ICP in real-time. You'll hear the same problems repeated across 10+ conversations. A founder I worked with interviewed VP Marketing at venture backed startups. After 15 conversations, 80% mentioned the same pain - attribution across multiple touchpoints. He didn't guess his ICP. His prospects told him.

2. It hands you messaging that actually resonates. Their exact words become your outbound copy. Not what you THINK the problem is. What they told you the problem is, in their own language. That's the difference between a cold email that gets deleted and one that gets a reply.

3. It generates pipeline without a single pitch. A healthcare dev services company I advised ran this play with medical device leaders (offered to feature them on their blog). They built pipeline AND a referral network. At the end of every call they asked for a referral.

Make it easy — "content asset" doesn’t mean launching a podcast. Record the call in Fathom. Let AI pull out the insights. Turn it into a 5-page PDF with your branding.

The beautiful thing about this play is what it ISN'T. It's not a pitch disguised as a conversation. It's a real conversation that happens to build everything you need…. your ICP, your messaging, your pipeline, and your content - all at once.

30 minutes. One conversation. Four outcomes.

Most reps chase ghosted prospects with desperation. Flip it — empower the no.

Kodak asks Don Draper to sell a slide projector they call "The Wheel." He's supposed to demo the technology.

Instead, he dims the lights, loads his own family photos, and talks about nostalgia. By the time he's done, one exec is crying. The product hasn't been mentioned once.

Draper didn't pitch features. He made the room FEEL something using a story (we covered storytelling last week). That feeling is what closed the deal.

The sales move: Start with the problem. Tell the story of a customer who felt exactly what your prospect feels right now. Make them see themselves in it before you ever show a feature.

The Outbound OS — a system for founders, sales leaders and channel builders who want predictable pipeline. I've spent the last few months interviewing people to refine the outline — I think you’ll like it. More to come. Reply "OS" if you want early access.

Until next week,

TG

P.S. I reply to all emails.