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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.

Toxic vs. Diva
Featured Post

StartUp Founders: Toxic vs. Diva

Hey Reader, Toxic employees kill companies.Nope.Mediocre employees do. If you truly, deeply, obsessively care about what you're building… you’ve probably been called toxic, probably even felt a little toxics. But there’s a world of difference between destructive behavior (toxic) and productive intensity (diva energy). If caring too much, pushing too hard, and refusing to lower your standards makes someone a diva? Then yeah. Hire more of them. intensity ≠ toxicity What people really mean when...

Possible. Probable. Inevitable.

Hey Reader, You can only believe in what you don’t know. That’s why you started. Right? Every great startup begins as an act of defiance against the existing reality.Not always to change the world. Sometimes, just to make something a bit better. You see a gap in the market, an edge, a better way. You imagine the future. The users, the traction, the growth, the impact. You see your life on the other side. Ugh. The seduction of possibility. Every founder starts at zero. Just the idea, a vision...

Big Doors, Small Hinges

Hey Reader, The biggest inflection points in your startup won't feel big when they happen. It's the smallest shifts that change everything. Big Doors Swing on Small Hinges is tied to decisions, actions, and communication. 🚀 The decision that kills your startup won't feel big when you make it. That's what makes it dangerous.🚀 The decision that changes everything won't feel big either. That's why most founders miss it. This is the counter-balance to the entropy newsletter. The thousand tiny...

Procrastinate

Hey Reader, The quicker you realize your brain has two sides, and they love to compete, the more fun everything gets. One side wants to grind. To push through. To brute-force a solution. Startup culture punishes inaction... It worships speed. The other needs you to step aside so it can actually do the work. The quicker you realize procrastination also has two sides and they feel exactly the same, the more dangerous it gets. One side is destructive. Avoidance, fear, resistance. The other is...

Buying PMF

Hey Reader, You can't spend your way into product-market fit. Early days you only have one job. Get people to need what you built. That's it. Move from experiment to business. Anything else is a distraction. 🚀 Early stage? Money buys time.🚀 Some traction? Money buys growth.💀 No demand? Money buys nothing. Almost every founder finds out too late they wasted money chasing fit, either because they run out of money or the grave yard of features no one uses. Yes, one killer feature can unlock...

Monopsony Trap

Hey Reader, There's a trap founders love walking into (and often have to & should). Chasing the dream customer, perfect partnership, frictionless growth channel. The massive logo that will change everything. You know you'll do anything to win it, despite the risks. And you probably should.... Founders don't care. Because the upside is real, and the belief that you can out execute the risk is what makes you a founder. Right? But now you have to win it, at all costs. It's been the opening...

AI Wrappers

Hey Reader, "That’s just an AI wrapper." "A lazy UI on GPT with some marketing fluff." "A thin interface that adds nothing.""A business that could disappear overnight." Okay. And? Postmates was kinda a wrapper on top of restaurants?Uber was kinda a wrapper on top of car services?Shopify was kinda a wrapper on top of selling stuff? Confusing? They started by aggregating existing supply, layered on a simple UI that connected users to a service. Isn't that what a wrapper is? Until they weren’t....

Anti-Patterns

Hey Reader, The founder is always the protagonist. It's the most epic, terrifying, and brutal part of starting a startup. Until you confuse protagonist with savior. "We need to build everything in-house. It's the only way to ensure quality." This founder's Series A startup had burned through $8M building their own infrastructure. They shut down last month. That's not you, you don't have $8m and not building your own infra, but the underlying mistake. That's you. It wasn't stupidity that...

Entropy

Hey Reader, Startups rarely fail with a bang. Most fail with a thousand tiny compromises. But the ones that get a little traction? The rare combo of relentless founder and a validated idea (the jockey and the horse). So many of them die because they can’t convert that early traction into something bigger. Often because entropy wins. You’re doing the work. Motivated. Excited. Probably working harder than ever. Momentum definitely feels real. And yet... Things are slipping. Entropy isn’t...

Motivation

Hey Reader, That motivation you felt on January 1st? Dead? We all entered January high on motivation. New year, new me, new strategy, new momentum - this is MY year. Then reality hits... The fires burned, TikTok turned off, political uncertainty loomed... Your prospects ghosted. Your ads didn't convert. Your dev team just cannot finish that feature. New Year. New Me. Got you to mid January! It's not even February, and the cracks are already showing, for everyone, not just you. Motivation is...