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...
14 days ago • 4 min read
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....
21 days ago • 4 min read
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...
about 1 month ago • 5 min read
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...
about 1 month ago • 3 min read
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...
about 2 months ago • 4 min read
Hey Reader, First, wishing you and yours a healthy, happy holiday season, and a moment for real reflection. Second, thank you. I started this newsletter 18 months ago to stay connected with people who reached out for assistance. 150k readers later, it’s the best part of my week. I have no saved drafts. Just me, every Friday night, arguing with myself about what I want to say. Feel like leaving a testimonial? I want to share three (of many) mindset shifts that changed how I think and operate...
3 months ago • 2 min read
Hey Reader, Don’t say it. December’s a dead zone. Investors are skiing, customer "out of offices" are already appearing, and you've put your pipeline & outbound on ice. I don't buy it, but let’s pretend I agree. That leaves one option… T-21 days. 504 hours (300 working hours?). To roll into 2025 ready to just f’n explode. Jan 6th. First Monday back. That’s your moment of truth. This isn’t the end of a year. It’s the start of one. While everyone’s mumbling their “New Year, New Start” mantra,...
3 months ago • 4 min read
Hey Reader, Every founder is racing to build a product. Every team calls themselves innovative. Every startup claims to be disruptive. Everyone believes they’re running a growth playbook. Every pitch deck believes itself to be funding ready. Nope. Those are outcomes. You don’t get to say those words. You don’t do product. You don’t do growth. You don’t do innovation. You don’t do funding. You don’t do disruption. You don’t get to self-name these attributes. They are given to you. By the...
3 months ago • 3 min read
Hey Reader, This one’s for all the founders heading into 2025 thinking your strategy will unfold naturally, as a sequence of inevitable events. It won’t. I'm just asking you to clearly articulate your objective and how you intend to hit it, it's a very reasonable question.... There are four types of founders on December 1st: Those winging it with random acts of execution believing they are following a plan. Those carrying a strategy in their head, trusting a brain notoriously bad at managing...
3 months ago • 4 min read