What The Hell Do You Actually Do? A Conversation with Simon Schmitz

Somewhere between "AI-powered" and "revolutionizing the future of," my brain checks out.

And I don't think I'm alone in this. Every startup website sounds identical right now. Every pitch deck hits the same notes. Disrupting. Leveraging. Transforming. It's like the entire SaaS industry went through the same creative writing class and nobody failed.

So when I heard about Simon Schmitz, a guy who's built an entire business helping founders answer the most basic question a stranger asks at a conference, I had to get him on. That question being: so what do you actually do?

From German politics to AI startup positioning

Simon didn't plan this. Nobody plans this.

He picked politics at university because it had the least amount of math. Did some internships at a marketing agency in high school, liked it, filed it away. Ended up working on election campaigns in Germany anyway. Then decided to get his master's in the US and somehow landed on urban planning because he got genuinely interested in why cities are built the way they are. What makes them livable. What makes them walkable.

Worked for government agencies after that. Then COVID hit. Everything slowed down. He started doing content strategy on the side, built some clients, got decent traction. But the feedback kept pointing at the same thing. Clients didn't care about the content. They valued the positioning work he did upstream, the part he wasn't charging for.

So he flipped it. Made positioning the whole offer. Named the company Lemoncore. Named the sprint The Squeeze because he works at a company called Lemoncore and at some point you just have to commit to the bit.

What politics actually teaches you about messaging

My wife figured this out before I even started recording.

I was telling her about Simon on the drive over, his background, the career path, all of it. And she stopped me and said there's a reason someone from politics is good at messaging. Because in politics you don't need to be the best candidate to win. You just need the clearest message.

Keir Starmer. Change. That was it. Trump. Drain the swamp. You can have opinions about both of them but you cannot argue with the clarity. Simple, persistent, memorable. People voted for the thing they could remember, not the thing with the best policy paper.

Simon's take was that startups make the exact same mistake parties do. They focus on what they're proud of instead of what their buyer is actually worried about. Parties lose elections positioning around the issues they're good at when voters care about something completely different. Startups build feature lists when buyers just want to know if the thing solves their specific problem.

The medium is different. The mistake is identical.

How bad does it have to get before someone calls you

Two types of people end up in Simon's workshops.

The first type has a feeling they can't name. They keep having the same meeting about what they want to be known for and they keep leaving without an answer. They might not call it a positioning problem. They call it an existential crisis or a messaging issue or just a thing that won't go away. But they know something is off.

The second type has a more obvious symptom. Sales calls start well. The prospect likes them. Nobody closes. The product team is building something different from what sales is explaining. Marketing can't describe the product to its own audience. And the homepage is somehow packed with words while saying absolutely nothing.

Simon's test is simple. Pull up the homepage. If a stranger can't figure out what the company does in thirty seconds, that's not a writing problem. That's a positioning problem. The writing is just where it shows up.

Why two weeks works when six months doesn't

I pushed him on this because it sounds like a sales pitch. A two-week sprint fixes what six months of internal meetings couldn't?

His answer was the college essay deadline.

If the essay is due in August and it's May, you're starting it the last two weeks of July. And that version is usually better than anything you'd have written in May. Not because you're smarter in July. Because the deadline forces commitment. It stops you from endlessly reconsidering decisions you already made correctly.

The Squeeze is four sequential workshops. Each one builds on the last. The whole structure is designed to not give founders enough time to second-guess themselves between sessions. You go deep, you go fast, and at the end you pick a direction and you give it time to actually work.

Most companies don't have a positioning problem because they can't think clearly. They have a positioning problem because they've been thinking about it for too long with too many people in too many rooms with no deadline forcing anyone to commit.

The unique thing is usually already there

Simon audits websites for fun. His words, not mine. And his observation after doing this more times than any sane person should is that most companies actually do have something genuinely different about them.

It's just buried.

Hidden in a customer review at the bottom of the page. Tucked into the third paragraph of the about section. Nowhere near where anyone who just landed on the homepage would ever see it.

The founders who can't answer "what makes you different" aren't usually wrong about having a differentiator. They've just stopped looking at their own product from the outside. The thing that makes them worth choosing is sitting right there in their best customer's words and they walked right past it.

Key takeaways

Simon comes from a world where the clearest message wins elections. Sitting across from him for an hour you realize how little that principle has made its way into how most startups actually talk about themselves.

A few things from this conversation worth holding onto.

Clarity is not a writing problem. If your homepage confuses people, rewriting the copy doesn't fix it. Repositioning fixes it. Then you rewrite the copy. Most companies try to do it the other way around and wonder why nothing changes.

The clearest message beats the best product. This is uncomfortable and also obviously true. You've seen it. A competitor with an inferior product but a simpler story takes market share from a company with genuinely better technology. Messaging isn't decoration. It's how the product gets chosen.

Your differentiator is probably already in your customer reviews. Not in your founder's vision statement. Not in your product roadmap. In the thing your best customers keep saying about you in their own words. Find it. Move it to the top of the page.

Niching down is not losing revenue. It's choosing which revenue to go after first. You cannot position a five-person startup at the whole market and expect to win. Pick the customers you've served best. Speak directly to them. The rest follows or it doesn't but at least you're building something coherent.

Commit to the position and give it time. Positioning is a long bet. Simon said most companies take six months to a year to see the results of a repositioning. If you change direction every three months because the results haven't shown up yet you'll never know if the original call was right.

Frameworks worth stealing

The Squeeze

A two-week positioning sprint built around four sequential workshops. The structure is deliberate. Each workshop builds on the previous one and the two-week window is tight enough that founders don't have time to second-guess good decisions between sessions.

At the end you get positioning options with the risks and upsides of each laid out clearly. You pick one. You commit to it. You give it at least six months before you evaluate whether it worked.

The sprint doesn't work for everyone. If your founding team can't agree in a room, can't make a decision and stick with it, or is fundamentally unwilling to niche down, the sprint surfaces that problem but it can't fix it. Sometimes the deeper issue is decision-making, not messaging.

The homepage test

Pull up your homepage right now. Read it like you've never heard of your company.

Three questions. What does this product actually do? Who is it for? Why should I pick this over anyone else?

If you can't answer all three in thirty seconds you have a positioning problem not a design problem. Fix the positioning. Then redesign the page.

Feature first, problem second

Lead with what the product does. Immediately follow with the problem it solves. In that order.

The logic is simple. If your buyer already knows they have a problem they're not looking to be reminded of it. They're looking for the capability that fixes it. State the capability clearly. Then show them it solves their specific problem. That sequence makes buying decisions easy. Reversing it makes people feel heard but confused.

Quotes worth keeping

Simon doesn't say a lot of flashy things. He says precise things. These are the ones that stuck.

If you do everything averagely, even though it sounds good on paper and you think you're covering everything, you're setting yourself up for failure.

The unique capabilities are usually hidden in the customer reviews at the bottom of the page. Not where they should be.

Positioning is a bet. You're saying this is what the market wants, this is the problem we solve, and our product solves it competently. If you're completely risk-averse and you want to please everyone, good luck.

This one I keep thinking about because it's the simplest thing he said and also the most honest.

In politics you don't need the best policies. You need the clearest message. Business is no different.

Rapid fire round

Same questions every guest. No prep. No warning. Here's how Simon handled it.

Best advice you've ever received? Don't be afraid to take chances but don't rush toward unnecessary risks. He's naturally risk-averse. Moving countries, starting a company, those were calculated bets that paid off. He didn't flip a coin on either of them. The point isn't to be reckless. It's to not let risk-aversion stop you from doing the things that actually matter.

Advice you wish you'd listened to? Get better at sales by doing more of it earlier. He knew he needed to sell to grow the business. He kept waiting to feel ready. The feedback you get from people who say no to you is more valuable than another month of refining your offer in private. He knows this now. Learned it the hard way like most people do.

What would you tell your younger self? Don't be so rigid about how life is supposed to pan out. He had the whole thing mapped out. Finish school, get a stable job, change it once maybe, retire. Germany likes stability. The plan made sense. Life had completely different ideas and he's considerably better off for it.

Ongoing challenge that keeps you up at night? Closing sales calls. He replays them afterward. Thinks about what he could have done differently. Whether he was too agreeable. Whether he should have pushed harder. The irony of a positioning consultant spending his evenings second-guessing his own sales conversations is real and he's aware of it. Sales is hard. Knowing that doesn't make it easier.

Favorite spot in New York? Kunjib in Koreatown. Korean food. Unfriendly staff. Questionable cleanliness. Always packed. His wife is half Korean so he has opinions on this. By his own logic all of those details are green flags. He's probably right.

Tool you can't live without? Whisper Flow. Voice dictation. Uses it constantly because typing feels too slow now. Once you go voice apparently you don't go back. I'm tagging them. Let's see what happens.

One piece of advice for someone starting out? Get your product in front of people before it's perfect. The feedback from people who don't want to work with you tells you more than another month of internal iteration. Ship the thing. Talk to real people. Fix what's broken. The version in your head is never the version that matters.

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Simon Schmitz is the founder of Lemoncore, a positioning consultancy for B2B AI startups. Find him on LinkedIn.