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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.

My Fault
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StartUp Founders: My Fault

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...

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,...

Startup Outcomes, Download the template

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...

2025 Strategy, Download the template

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...

Becoming Core, Download the template

Hey Reader, Founders: If I teamed up with your local bookstore to host some meetups - where I buy you a coffee, we share stories, do some founder therapy, and spark new connections - would you come? If so, click here. For every founder building helpful, nice-to-have products that people like and might pay for. Are you essential? Without you, is the pain immediate and undeniable? With you, is the value obvious and compounding? Are you CORE? CORE decides how easy you are to ignore in a sales...

The Golden Rule

Hey Reader, Every founder is driven by the pursuit of advantage. The shortcuts, insights, frameworks, and sparks that, just maybe, ignite the one idea, the one insight, the unlock code that can be leveraged. One goal. Move faster, smarter, better. Last week's newsletter, on founders navigating the space between what was and what will be... resonated... <join in> The great thing about someone else's method is that one of two things will happen: Either you'll embrace it, find that it works for...

Porter's Five Forces, Download the template

Hey Reader, Change is the only constant. Whether it's politics, economy or tech, the forces around us are always evolving. The recent US election? One more example of how quickly the landscape can shift. Change is also the engine of progress. It forces you to adapt, innovate, and become a stronger founder. Ten minutes ago, none of us had “AI” in our pitch decks. Today, it’s transforming everything and likely front & center on your website. Tomorrow? Who knows. Exactly the point. So, if it's...

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...