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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.

Customer Hostage
Featured Post

StartUp Founders: 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...

Love the fight

Hey Reader, The worst thing that can happen to you isn't rejection, runway, co-founder walking, or even building a product no one wants. It's resenting the hits. Believing they shouldn't have happened. A lot of our conversation is that shitty moments are part of the process, a view that you should be grateful for the stress. But there's another way of looking at it... love of the fight. If you can broadly accept my thesis: Everything that happens is your fault, because ownership is the...

Nerves

Hey Reader, Do you have a pipeline problem or do you have a nerve problem? More specifically, are you more comfortable emailing 20k cold leads via some LinkedIn automation than asking your network for help? The answer to almost all of your early-stage questions - maybe late-stage too - is likely in your contacts. And before you start trying to find more cold imaginary leads that kinda match your ICP and put them in some sort of doom funnel, why wouldn't you text your contacts? All of them....

Quit

Hey Reader, The word quit tastes like metal in the mouth. It sounds like failure, but really it’s a dirty word for allocation. This is not a pep talk or a eulogy, that’s not my job. Mine is just to ask you to hold up a mirror if you’ve stalled, and consider three honest paths: Keep Going (Beast Mode): The loops are kinda working. The smoke signals are kinda forming. You are confident this isn’t a delusion issue, the issue is it’s just not fast enough. (the dip) Redeploy (New Vehicle): You...

No one cares

Hey Reader, Who cares. Hurry up. That's it. That's the whole message. As in stop doing random acts of nothingness that don’t drive the outcome.Do the thing that matters. Do it again. It's not about being perfect. It's about moving. And violently ignoring everything else that doesn't align with your goal for today. Go do that. Also, if you happen to enjoy my content, would be hugely appreciative if you could pre-order my book. Starting A Startup: Build Something People Want Every founder...

Build The Toy

Hey Reader, Focus. Relentlessly. With precision. Insane Discipline. Unreasonable levels of work. Just you. Heads down. Do the work. Ship the roadmap. Hit the milestones. But also? Build the toy.... Starting A Startup: Build Something People Want Every founder starts at zero. No one starts with a product, customers, revenue, or a real clue how it will all play out. Failure is the result of not doing everything in your power to turn your nothing into something. It's that simple. Buy Now Want to...

Homicide Detective

Hey Reader, The wannabe founders can talk about their idea, the market, the problem statement, all 11 slides on the YC deck template and sound fab. Good founders can go deeper. The players, the mechanics, the moving parts. The network, the sales plays, the - wow this founder really knows their shit kinda founder. Great founders? They know it all. They've lived in the problem so long (enough), gone so deep (enough), it's part of their DNA. They know shit that we don't even think to ask....

Early Days

Hey Reader, The early days f’n suck. The super-early stage actually lasts way past when you thought you’d be through it. It’s deeply embarrassing. And any sane outsider would believe you shouldn’t even be in business. Your product is held together with duct tape and prayer. Your team is three people working for equity in a company worth 0. Your runway is some black magic of squeezing 6 months out of 2 months of cash. Your biggest customer is your friend, and she doesn't actually use it. The...