Insights / Startups
Startups
On startup funding stages and the antifragile-systems thinking that separates startups that bend from ones that break.
14 essays
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Early-stage startup CEO 2020 learned lessons
Five lessons from leading a startup through 2020: hire A+ people, let the team own problems, tell one clear story, match your velocity to the market.
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Entrepreneurs, Don’t Start Without a Strategy
Strategy is getting desirable ends with available means. Why founders need one before day one, and why it doesn't conflict with moving fast.
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The Art of War and Strategy for Entrepreneurs – Situational Awareness
Using Sun Tzu's five factors to build situational awareness: how founders read macro trends and micro signals before committing to a strategy.
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8 Pitch Deck Slides Must Have In Your Startup Fundraising
The eight slides every fundraising deck needs, from opportunity to ask — drawn from my own pitches and the many NOs before the YES.
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Top 3 Critical Slides in Your Startup Pitch Deck
Traction, team, and market are the three slides that actually land funding. What belongs in each and the metrics VCs want to see.
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On Building Anti-Fragile Startups – Part 3 – Robust Startups
Part 3 of the antifragile series: what makes a startup robust — the right team, PMF as north star, repeatability, brand, and resources to experiment.
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4 Essential Questions To Ask Yourself Before Fundraising As A Startup
Four questions to answer before pitching VCs: why raise at all, how much you need, what you'd do without the money, and whether VC funding even fits.
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6 Stages of Startup Funding Every Entrepreneur Must Know
A founder's map of the stages of startup funding, pre-seed through Series D-F: what each round funds and what investors expect before writing a check.
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Six Sources Entrepreneurs Must Consider for Their Startup Funding
Six sources of startup funding — friends and family, crowdfunding, accelerators, and more — and how to pick the source that fits your stage and goals.
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2023 Startup Funding Checklist
A practical startup funding checklist: know your target market, sharpen the pitch deck, build a warm network, and shortlist the right investors.
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Towards Building AntiFragile Startups – Part 2 – Fragile Startups
Part 2 of the antifragile series: the five failure patterns of fragile startups, from building what no one wants to slow experimentation.
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On Building Antifragile Startup – Part 1
Part 1: what an antifragile startup is, applying Taleb's fragile-robust-antifragile spectrum — why merely surviving stress isn't enough for founders.
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Avoid these 3 Startup Fundraising Mistakes in 2023
The fundraising mistakes I made as a founder — muddled decks, pitching the wrong investors, unrealistic asks — and how to avoid repeating them.
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Pitching Your Startup? Don’t Confuse Solution and Product Slides
Your solution slide is the strategy; your product slide is how you deliver it. Mixing the two muddies your pitch and costs investor confidence.