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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 & author of the #1 Best Seller "Starting A StartUp | Build Something People Want."

December Decides
Featured Post

StartUp Founders: December Decides

Hey Reader, Every founder has an imaginary list called “I’ll get to that in December.” It follows you all year while you're in the trenches, this dumping ground for everything you don’t have time for but swear you’ll handle when things “calm down.” Do I need to list them, or are we on the same page... So. Funny story. December is here. Four weeks to do nine weeks of work... The stuff you pushed off, the stuff you forgot, the stuff you should’ve done already, and the stuff you promised...

First Belief

Hey Reader, The very first thing every founder says before the product exists, a single customer or dollar shows up, before any proof of any kind is some version of: I can do this. It's rarely evidence led, something inside you decides it's worth believing. It's not fraud. It's not delusion. It's simply the starting point. And this is really important. Founding rarely begins with real data. It begins with a belief you have no business holding yet and then spending years trying to earn it -...

Am I Better

Hey Reader, Early days, I’m not sold MRR is THE metric. Or lack of churn. Or customer adoption. Or usage over time cohort analysis. Or some performative PMF metric. Because I think, generally, these positive market signals are reflective of a different metric. The YOU metric… AIB. Am I Better. What proof do I have to show that. MRR is a lagging indicator of what you’ve already built. AIB is a leading indicator of what you’re capable of building. If the founder hasn’t evolved, they’ll...

The Third Variable

Hey Reader, That moment when something isn't working and you have an immediate explanation? The lead ghosted, they're just not ready. The feature flopped, they're using it wrong. The hire isn't crushing it, they don't understand our hustle. Fast. Confident. Wrong.Causation. Correlation. The other thing you ignored. Your brain is working overtime to make you happy, to connect dots, to "close the file" and in doing so, it often generates plausible sounding bullshit. You do/see X, then Y...

Until Friday

Hey Reader, You don’t have infinite time. You have until Friday. I hope I sound repetitive. I’d say it every week, because little else matters. No one cares about your horizontal fluff work. What matters is whether the business is moving exponentially forward in the right direction. Right now. Clock speed. The speed at which you release, get feedback, learn, iterate, release again. Clock speed. The fastest team to learn wins. Clock speed. Getting in traffic and proving what you believe to be...

Forward Deployed

Hey Reader, At some point, whether you've been tracking Palantir, been in startup, software, or product circles, B2B, B2C, or anywhere in between, you've heard the term forward-deployed engineer. Sounds expensive. Sounds technical. But it's really about something universal. Making your customer’s success inevitable. Many founders stay busy doing horizontal fluff. Universally applicable work that looks productive but helps no one specifically. Forward-deployed founders do the opposite. The...

Hard No

Hey Reader, Implicitly or explicitly, the most common word a founder ever hears is no. And just to be clear. There’s a difference in no. There’s “no” as a boundary. The kind that protects, that ends the conversation. And there’s “no” as a negotiation. The kind that starts it. I have a six-year-old.“No, you can’t have your iPad” is a negotiation.“No, you can’t climb inside the fireplace and up the chimney” is a boundary. What we’re talking about here is the negotiation kind. The no that shows...

Customer Hostage

Hey Reader, The line between early traction and early captivity is razor thin. No matter who you are, frictionless B2C to heavy B2B, your first customers are, by design, total mayhem at best. They expose the sh*t that's broken. The sh*t you forgot. The support doc you never wrote. The button in the wrong place. The button missing. All of it. Go deeper, the infrastructure that cannot handle the load, the observability missing so you have no idea what's happening. All of it. The great thing...

The Memo

Hey Reader, Thanks for supporting my book launch the last two weeks, I am incredibly thankful for your support. This week isn’t a newsletter. It’s a memo. The market looks better than ever and worse than ever. Multiples make no sense. AI is rewriting the rules. Money’s flying, but not always toward you. The default triple, triple, double, double that used to guarantee venture investment is gone. Churn is brutal. Pricing models are delusional. Breathing room is non-existent. The market is...

The Ask

Hey Reader, For two years I've written this newsletter every week. Said no to the shitty sponsors. Pretty much the only newsletter without a paid tier and without a crypto sponsor. I answered your emails, engaged on social, and shipped something I thought was of extraordinary value. Now it's my turn, for the first (and last) time.... My book goes into general release this Tuesday. I'm asking you to buy the book: Starting a Startup: Build Something People Want. If you've ever gotten value from...