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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.

Hero Stories
Featured Post

StartUp Founders: Hero Stories

Hey Reader, Startup culture is built on a lie: the myth that other founders are somehow better than you. That they know exactly what they’re doing and execute flawlessly. (𝕏) These hero stories paint a picture where every decision was inevitable, every move was calculated, and the outcomes obvious. Nope. For everyone, it was a whole lot of chaos, guessing, hoping, and praying. Stop holding yourself to impossible standards, stop comparing your behind-the-scenes reality to someone else’s...

The Dip

Hey Reader, There’s a part of the startup journey that’s brutal and rarely mentioned. The Dip. The exact opposite of the adrenaline, excitement & energy of the beginning. The Dip feels like a deep, personal struggle, and yet, it's a universal founder experience. (𝕏) The Dip isn't burnout. That's different. It's also not procrastination. That's avoiding (the right) work. The Dip is the lag between momentum and traction. When your adrenaline has burned out but reality hasn't caught up - the...

How you operate, download the template

Hey Reader, Everyone talks about IQ & EQ, but what about how you instinctively take action and solve problems? Who you are at your core is not really trainable or changeable, but it’s often the hidden reason startups struggle to make progress in the early days. (𝕏) It’s the Conative Index and you care because founders often fight their natural tendencies, believing they need to act a certain “founder” way (move fast & break things). And when that isn't who you really are, you end up battling...

NPC Mode

Hey Reader, Just like that, without realizing it, you go from founder to NPC. From having a clear vision, some moxie, and a bold idea, to being pushed into normalcy as the market never stops telling you that you're doing it wrong. (𝕏) NPC often happens in moments of desperation, where you stop (or are forced to stop) critically evaluating, questioning, investigating, and instead go with the flow, follow the popular, execute the so-called "right" advice. Just like the background characters in...

Price Evolution, Download the template

Hey Reader, There's a whisper we are seeing in SaaS, that improving productivity of your users, or automating functions normally done by users, leads to them buying fewer seats. The irony of building a fab product.... (𝕏) We are seeing the emergence of usage-based pricing expand beyond traditional models (like API & Platform) into new areas, along with the rise of outcome-based pricing. It's not universal, it's not absolute, but it's not not happening. If Salesforce is the bellwether for the...

StartUp Founders: Assumption Detox

Hey Reader, StartUps are built on a foundation of assumptions. Some are spot-on. Others, pure delusion. As a founder, it's hard to tell the difference. Not because you're reckless or ignorant. You're just so deep in your solution that you lost perspective. (𝕏) Whether you're two weeks or two years into your journey, you need the courage to continually return to first principles. Are the assumptions we made yesterday still true today? If you are pre-launch or just launched and hearing...

Hey Reader, The biggest lie, after the diamond industry, greeting cards, and the middle choice at the gas pump, is that you can't have it all; fast, cheap, good - you must pick two. It's a phenomenal sales slogan because it sounds reasonable, but..it's complete bullshit. (𝕏) Turns out, the people most equipped to execute this trifecta are founders, the ones with a to-do list longer than a CVS receipt. There are two types of founders: those who make things happen, and those who wonder what...

Extreme Uncertainty, Download the template

Hey Reader, Extreme uncertainty is literally the MO of StartUp Founders. Make decisions that are hopefully on the righter side of right, praying that when you hit, the impact moves the needle. (𝕏) There's no playbook, no perfect formula. Don't get caught up in finding the right way to do things. Just get out there and build, with a touch of structured intention. TL;DR Even gut decisions need a framework to drive resources towards actions with the potential for high impact and some level of...

StartUp Founders, Beast (Founder) Mode

Hey Reader, The entire journey of trying to get your StartUp off the ground is so you can delegate something to someone else. Right? That's scalability. Wrong. Dead wrong.(𝕏) That thinking often comes from smart, experienced people who think they understand what it takes to manifest something from nothing, but they don't get that founders are a different breed. TL;DR Brian Chesky of AirBnB argues that most scaling advice he received was wrong. Instead of stepping back, he fired middle...

Hey Reader, Remember when you thought building the product was the hard part? Cute. (𝕏) The second your product hits the market, a whole new attack sequence starts. Suddenly, everyone's fighting to steer you off course - including yourself. You're juggling shiny objects, must-have features, demanding customers, and new idea grenades. Straddling sales, product & operations is both your superpower and your kryptonite. TL;DR In-market? Decisions are based on facts AND intuition, not just gut...