Obsessive One-Liners

Obsession and meticulousness in communication & product

TLDR: Most founders fail to communicate their startup clearly. A strong one-liner makes investors lean in, customers buy, and employees rally around the mission.

The One-Liner

If you can’t describe your startup in a single, clear sentence, you have a problem.

Founders often use buzzwords and jargon to sound impressive, but the best companies communicate in a way that’s simple, compelling, and instantly understandable.

A great one-liner is the foundation of everything—your pitch, your sales strategy, and ultimately, your leadership. In this guide, we’ll cover why most founders get this wrong, how to craft a powerful one-liner, and how to refine it until it unlocks real results.

Why Most Founders Get This Wrong (And How It’s Costing Them Money)

Most founders think they’re explaining their startup well—but they’re actually losing investors, employees, and customers because their messaging is confusing, vague, or forgettable.

🚫 Weak communication is the most corrosive and compounding force in all of business.

In your investors meetings, it’s probably resulting in the inevitable soft pass: “you’re great, but we’re going to wait for now”

And in hiring, selling, and inspiring your team, it’s probably having a drag on your business that you can hardly detect let alone measure—but trust me, it’s bigger than you think it is.

When it comes to the one-liner, founders underestimate it’s importance, and overestimate it’s effectiveness. They default to big, impressive language—but that’s exactly what makes them forgettable. They use vague, overhyped buzzwords instead of stating the actual value they create.

Here’s a soft example to start, can you tell the difference"?

❌ “We’re a paradigm-shifting AI-driven platform redefining the future of commerce.”
✅ “We help brands sell more online by predicting which products will go viral.”

Investors don’t invest in fluff. Employees don’t join visions they can’t understand. Customers don’t buy what they can’t explain to a friend.

Your one-liner isn’t a tagline—it’s the foundation of how you fundraise, hire, sell, and lead. Get it right, and everything gets easier. Get it wrong, and you’re fighting uphill in every conversation.

The Founder's Communication Problem

The problem isn't just the words you use—it's the way you think about communicating. Most founders:

🔴 Try to sound bigger than they are. They say things like “paradigm-shifting” instead of just explaining what they do.
🔴 Overcomplicate their messaging. If your one-liner requires a follow-up explanation, it’s failing.
🔴 Aren’t learning from feedback. Instead of iterating based on investor reactions, they keep saying the same ineffective thing.
🔴 Lack consistency. They change how they describe their company every time they pitch, making it impossible for anyone to remember them.

Lessons from the Best: One-Liners that Work vs. Ones That Don’t

The best fundraising one-liners are clear, specific, and immediately compelling. Here’s how strong one-liners differ from weak ones:

Biggest One-Liner Mistakes Founders Make

🚫 Too vague: “A cutting-edge AI solution for commerce.” (What does it actually do?)
🚫 Too long: “We’re an AI-powered predictive analytics engine that helps retailers forecast demand and optimize inventory management to increase profitability.” (Too much!)
🚫 Too generic: “A platform that connects businesses with customers.” (No differentiation.)
🚫 Too complex: “A proprietary ML-driven algorithmic ecosystem for dynamic personalization in B2B commerce.” (What?)
🚫 Too hype-y: “Revolutionizing the way people experience the internet.” (Sounds impressive but means nothing.)

Avoiding these mistakes will set you up for success when crafting your one-liner.

How to Build a One-Liner That Cuts Through the Noise

1️⃣ Start with the Caveman Test – If a five-year-old can’t understand it, it’s too complex.

• ❌ “AI-powered growth engine for SMBs.”

• ✅ “We help «big market» get more «more value» by «unique value proposition or insight».”

2️⃣ Test It in Four Key Conversations – The best founders refine their one-liner through real-world feedback. Use this framework:

3️⃣ Refine Until It Spreads – A great one-liner is one people can repeat back to you.

• Employees should use it in hiring conversations.

• Customers should use it when referring you.

• Investors should use it when introducing you to others.

• If people aren’t repeating it, it’s not resonating yet.

You’ll Still Get Objections

Even with the perfect one-liner, you’ll still get objections.

Most founders go into defense when this happens. They start spewing facts and opinions rather than navigating the conversation in tandem with their counterpart.

This is the mastery of sales. Most have never been taught it, and when they’ve been exposed to it, they didn’t appreciate it.

As you pitch to investors, it’s not enough to simply get them interested with a one-liner, but your pitch needs to be packed with storytelling density and cold hard facts, and those ideals need to be woven through conversation, not through brute force.

Handling Investor Objections Like a Pro

This four-step objection handling framework originates from Xerox’s legendary sales training program, one of the most effective corporate sales training programs ever developed. It’s designed to help salespeople—and now founders—turn objections into opportunities by methodically understanding and addressing concerns.

Mastering this will make you better not just at fundraising, but also at hiring, selling, and closing high-value deals. Here is the four-step framework the best sellers use—whether they realize it or not:

1️⃣ Clarify the Objection – Ask open-ended questions to make sure you fully understand the concern. Example: “Can you tell me more?” or, you can mirror a customer by repeating back the last thing they said with inflection as though it were a question, “Scalability of the platform?”

2️⃣ Paraphrase the Concern as a Need – Reframe the objection as a need and as a question to confirm understanding before moving forward. If the investor corrects you, go back to Step 1 and clarify further. Example: “It sounds like you need confidence that our platform can scale as we grow. Is that correct?”

3️⃣ Respond with Facts, Value, and Proof – Provide real data, show the value, and offer evidence.

4️⃣ Test for Reaction – Confirm that your answer addressed their concern.

Common Investor Objections & How to Handle Them

Personally, I prefer one of two methods to clarify an objection.

The first is simply the open-ended, “can you tell me more about that?”

This version allows the customer to tell you exactly what is important to them by going deeper on what they meant in the few sentences prior. In other words, help me really understand what you care about. This works great for investors because they’re often moving the ball on founders, and this allows you to get deep on the intention of the question before responding.

The second one is something I like to think of as “the illusion of control.”

This one is simply a choice between to things the investor or customer might have meant, but they are both things that you have incredible answers for. This way, they have the illusion they are in control by picking chicken or fish, but in reality, both chicken and fish are things you very ready to handle.

This works best when you have battle tested your FAQ and you know that either question path is a homerun for you and your pitch.

Here are some examples:

How This Ties into Your Pitch, Fundraising, Hiring, and Sales

A great one-liner isn’t just a catchy phrase—it’s the core of your entire company narrative. Everything flows from it:

✅ Fundraising: Investors need to understand, repeat, and believe in your vision within seconds. If they don’t grasp it, they move on.

✅ Hiring: The best talent joins companies with a clear, compelling mission. If candidates don’t instantly understand what you’re building, they won’t feel inspired to join.

✅ Sales: Customers don’t buy confusion. If prospects don’t immediately get what you do and why it matters, they won’t engage.

✅ Marketing: Your one-liner is the foundation of all messaging—website copy, ads, emails, and social media should reinforce it.

The 100-Meeting Crucible

Most founders don’t truly refine their pitch until they’ve pitched 100 times. Investors, like great editors, cut through the fluff—they force you to distill your business down to its most essential, compelling form.

💡 Every pitch is a stress test. Watch where investors lean in and when they check out. If you’re getting the same objections over and over, your one-liner—and overall pitch—need work.

The One-Liner Mindset

Obsessing over your one-liner isn’t just about fundraising—it’s about how you communicate, execute, and lead. The same level of clarity should extend to:

✅ Your Pitch Deck – Every slide should reinforce your core message, eliminating confusion and preempting objections.
✅ Your Storytelling – Whether you're speaking at an event, on a podcast, or to a journalist, the way you articulate your business should always tie back to your crisp one-liner.
✅ Your Product Execution – A clear, well-articulated value proposition should drive product decisions, ensuring what you build aligns with what you say.
✅ Your Marketing & Sales – Your messaging should be so clear and repeatable that customers, employees, and even investors start selling for you.
✅ Your Hiring & Culture – The best talent joins companies with a mission they can instantly grasp and believe in.

A great one-liner isn’t just a phrase—it’s the foundation of your company’s entire identity. When your messaging is clear, your entire business becomes sharper.

When to Iterate Your One-Liner

🔄 If people keep asking, “So what does that mean?” → It’s too vague.

🔄 If customers don’t instantly understand the value. → It’s not clear enough.

🔄 If investors don’t get excited or ask follow-ups. → It’s not compelling.

🔄 If employees struggle to repeat it. → It’s not sticking internally.

🔄 If your business evolves (new focus, new customers, or new value prop). → Time to update!

Obsession Separates the Best Founders

Just look at Jerry Seinfeld and Ivan Zhao, the founder of Notion.

Jerry Seinfeld is of course one of the most successful comedians of all time, so it’s no wonder he is obsessive about refining his jokes—down to the exact word choice, timing, hand gestures, and audience reaction. He doesn’t just write a joke and assume it’s good. He tests it relentlessly, performing it in small clubs, tweaking a single word, adjusting his inflection, and observing when the audience leans in or tunes out.

He meticulously analyzes every beat of a joke, eliminating anything that doesn’t land. The result? A precision-crafted joke that feels effortless but is actually the product of relentless iteration.

This is exactly how founders should approach their one-liner. Every pitch, every conversation, every investor meeting is a test.

The best founders don’t just refine their one-liner—they obsess over it. Every interaction, every conversation, and every investor meeting is an opportunity to sharpen it.

The same needs to apply to all parts your business—especially the product.

Take Ivan Zhao, founder of Notion for example—he obsessed over building the perfect product. Notion struggled early on, forcing Zhao and his team to scrap everything and rebuild from scratch.

Zhao famously spent two years in “monk mode” obsessing over consumer behavior and design principles, refining the product in Kyoto, ensuring it was intuitive, flexible, and resonated deeply. That relentless focus on quality led Notion to break through with organic and viral growth that seemed to most everyone else to be an “overnight success,” but far from it — it was a labor of love.

This level of meticulousness isn’t optional—it’s the difference between a company that thrives and one that never gets traction.

At inception, your one-liner isn’t just a pitch—it’s the DNA of your company.

Obsess over it like your company depends on it—because it does.

See you Monday.