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StartUp To ScaleUp

Where 140k+ founders read my weekly newsletter offering tactical insights to start, scale, and fund their startup. Real advice from a 3x exited founder.

Quietly Freaking Out
Featured Post

StartUp Founders: Quietly Freaking Out

Hey Reader, You're probably quietly freaking out. It's a common theme I am hearing from founders at every stage of maturity. Every other LinkedIn post screaming with ridiculousness. I raised $30m in three minutes with AI, solo founders running businesses with 40 AI agents, MVPs vibe coded in a weekend with 100 customers and $22k MRR, the AI Marketing agency getting 82% conversion rates from emailing 3% of the world. AI video doubles auto-posting across founder socials while they sleep driving...

The Moat

Hey Reader, What stops someone from stealing your idea? Not much. In most cases, I can find, hire, or outsource to a team that gets to basic parity with your tech. I’m not talking about stealing your vision, that’s what makes you unique. I’m talking about stealing your traction. Your customers. Your edge. That’s what a "moat" protects. Your competitive advantage, your defensible edge. And if you don’t have one yet, be very clear what’s holding your position... likely by a thread. In the early...

SCARF Empathy

Hey Reader, We need gamification!! We need a checklist at signup, because users don’t like leaving jobs unfinished. That’s certainty. They want a clear path, closure, and to know what's next. We need badges and progress markers, because users like feeling recognized. That’s status. They need to feel like they’re getting somewhere and that it matters. We need customizable flows and smart defaults, because users don’t like being forced into decisions. That’s autonomy. Give them agency, or...

Unreasonable

Hey Reader, Have you met the threshold for earned inevitability? As in, have you done such relentless, uncomfortable, comprehensive work that it would actually be unreasonable for this not to work?Only you know. There’s a difference between working hard and working so hard it breaks the logic of failure. Which is the goal. To manufacture the default outcome. ....And to do that, you have to find that level, that gear, that moment when your effort becomes so complete, so relentless, so...

Borrowed Words

Hey Reader, One of the most epic truths about being a founder is knowing the real world exists, but you’re no longer living in it. You still do all the muggle things. Grocery store. Family group chat. Kid’s soccer game. Grandmas wifi. But your mind now lives in a parallel reality. The universe of “burn” “MVP” “PMF” “conversion” “CAC”... This is a follow-on from Reality ≠ Consensus: How people perceive your startup. This is about how you label it, and how those labels shape what you do next....

Pressure is a Privilege

Hey Reader, You're tired. You're poorer. You're late. You're a shit friend. You're overwhelmed. High fives. Congrats. You asked for this. 😉 Do you know how incredible that is? The fact that you're even stressed means something's actually happening. Your dev team is slow. A user churned. A customer wants a security review. Your upwork engineer is awful. A partner's dragging their feet. Someone quit. The demo went dead. Those aren't random problems.They're the problems you get when you're...

Incompetence or Ignorance?

Hey Reader, I’m about to say something brutal. It might sting. That’s the point. I only ever say these words when you can see my face, so you know how much love is behind them. But honestly. I want you to be moderately offended. Not because I’m trying to provoke you, but because I need this to land. I have danced around this for a while, you have to trust how founder-first I am. How in your corner, I truly am. Last week I said it softly. Maybe you didn’t fail, maybe you just never actually...

Cheer Squad

Hey Reader, The most founder thing you’ll ever do is clap for yourself in the dark. The everyday battle to carry something heavy that no one even knows you’re holding, and yet, everyday, you choose to lift it anyway. With all the founder myths, the hustle porn, and the startup optics, motivation gets fragile. Not because you’re weak but because you’re bombarded by stories that make it feel that if you’re struggling, you must be failing. But it’s not real. It’s curated. Calm down. I’m not...

The Kill Chain, Download the template

Hey Reader, Right now, in the thick of the hard work, it’s easy to confuse effort with progress. It's hard to separate exploration work from completion work. Both matter. But only one completes the job. That confusion usually starts with drift. Half-loops. Half-commits. All noise. It feels like action. It’s not. Let’s fix that. You half-execute. Test instead of commit. Cold email campaign with no replies? Failed channel. Fumbled pitch? Market doesn't work. Meanwhile, that unanswered email in...

Reality ? Consensus

Hey Reader, Your startup exists in multiple realities simultaneously.You see a unicorn. They see a horse with an ice cream cone stuck to its head. Same startup. Different realities. That gap between perceptions is where founders live every day... the space between what is and what's perceived. The investor who squints at your deck and diagnoses the wrong problem. The advisor who actually knows what's holding you back. The prospect who can't see why your solution matters. The team member who's...