Startups

Operating mechanics, capital, and the decisions that compound over time.

#197 — The doorman fallacy for founders
StartupsJul 23, 2026

#197 The doorman fallacy for founders

Startups are falling for what is known as the doorman fallacy: reducing rich and complex human roles to a single task and replacing people with AI.

#178 — The art of the investor update
StartupsFeb 23, 2026

#178 The art of the investor update

Sending world-class investor updates is one of the highest-value rituals you can learn. It matters more than most founders realize in good times and especially in bad.

#177 — Pitching to angel investors
StartupsFeb 21, 2026

#177 Pitching to angel investors

Securing angel investment can be a pivotal moment for any startup yet, the process of pitching to angel investors requires more than just a compelling idea.

#176 — How to build an investor map for startups
StartupsFeb 19, 2026

#176 How to build an investor map for startups

Securing the right investors can be a game-changer for any startup but how do you ensure youre targeting the right people?

#175 — Types of startup investors
StartupsFeb 17, 2026

#175 Types of startup investors

Startup funding is not one-size-fits-all. Different investors care about different things. The better you understand who youre pitching, the better your chances.

#174 — Post-money SAFEs for founders
StartupsFeb 15, 2026

#174 Post-money SAFEs for founders

SAFEs have become the go-to investment vehicle for pre-seed and seed rounds, but they're not without their complexities.

#173 — Canada vs. US incorporation
StartupsFeb 13, 2026

#173 Canada vs. US incorporation

Choosing between Canadian and U.S. incorporation is a critical decision. Changing course after incorporation is costly and complex. You must choose wisely.

#171 — Consumer 2.0: The return of consumer software
StartupsFeb 1, 2026

#171 Consumer 2.0: The return of consumer software

With the emergence of AI, the consumer software window has reopened after 11 years of drought.

#167 — How to grant equity in a Delaware LLC
StartupsJan 24, 2026

#167 How to grant equity in a Delaware LLC

Many non-US founders launch their startups as LLCs but that initial choice can make granting equity more complex.

#165 — Legal structures for LatAm startups
StartupsJan 20, 2026

#165 Legal structures for LatAm startups

Theres confusion around what legal structures make sense for Latin American startups and mistakes can cost millions.

#164 — Board reporting for founders: The essential guide
StartupsJan 18, 2026

#164 Board reporting for founders: The essential guide

Reporting to your board is a critical aspect of running a startup. It's important to understand the reporting process and the best practices for effective communication.

#161 — The fundraising calendar
StartupsJan 12, 2026

#161 The fundraising calendar

There is a seasonality to fundraising. When you raise your next round can have as much an impact as vision, product, and team. Don't leave it as an afterthought.

#143 — How to start an open-source startup
StartupsNov 23, 2025

#143 How to start an open-source startup

While fraught with tensions, OSS remains a positive force and a viable way to create and distribute software.

#73 — Best practices: When should you raise your Series A funding?
StartupsMay 28, 2025

#73 Best practices: When should you raise your Series A funding?

Timing is everything when it comes to raising Series A funding for your startup. Heres how to know if the timing is right.

#72 — Alternatives to venture capital
StartupsMay 26, 2025

#72 Alternatives to venture capital

VC isnt the only path strategically choose funding that matches your timeline, model, and long-term vision to retain control and maximize success.

#70 — Best practices: How to raise seed money for your startup
StartupsMay 22, 2025

#70 Best practices: How to raise seed money for your startup

Turn your startup idea into a fundable reality with a well-prepared fundraising strategy to secure seed funding.

#69 — How to raise capital for your startup
StartupsMay 20, 2025

#69 How to raise capital for your startup

Secure your startup's future by mastering the complete funding process, from bootstrapping to IPO and beyond.

#60 — Cap tables for startups explained (+ free cap table template)
StartupsApr 30, 2025

#60 Cap tables for startups explained (+ free cap table template)

A well-managed capitalization table (cap table) is essential for fundraising and strategic decision-making.

#38 — Best funding options for startups (2025)
StartupsJan 5, 2025

#38 Best funding options for startups (2025)

Explore funding sources, tips on preparing for funding conversations, and common mistakes to avoid.

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