Insights / Startups
Startups
On startup funding stages and the antifragile-systems thinking that separates startups that bend from ones that break.
17 essays
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How Outcome Pricing Changes the Scope of an Engagement
Outcome pricing moves every failure and every argument about what counts as done onto your margin. What to agree first, and when it's too early to …
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How to Scope a Forward Deployed Engineering Engagement
How to scope a forward deployed engineering engagement: when to refuse, who has to be in the room, and the one page to agree before anyone builds.
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How to Write an Exit Criterion for a Forward-Deployed Engagement
An exit criterion names the number, the baseline, the date and the person who reads it. How to write one before anyone on the team writes code.
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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.