Six for Startups #1

Lifelines // You may want to reconsider how you use product deadlines. James Hawkins, CEO of PostHog, shares why his team doesn’t use deadlines at all for product development, and what they do instead. For what it’s worth, I agree with Hawkins. If the goal is to ship more features quickly, more aggressive deadlines aren’t how you get there. Keep in mind, though, that Hawkins and PostHog are able to operate this way because they’ve very intentionally built a team and culture that supports it. Before making a whole-hog switch to a new model, consider how well your team will operate in it.

Department of Metaphor // One of my favorite startup thinkers, Christina Wodtke, wants you to change how you think about strategy. It’s not war, she says, but instead… “gardening offers a better framework for understanding strategy because it captures the nuance and complexity of building something sustainable over time. Like gardening, strategy isn’t just about fighting off threats—it’s about selecting the right environment, nurturing growth, and harvesting the rewards in a way that keeps the cycle going.”

The Innovator’s Dilemma // Citing Chegg and StackOverflow’s recent nosedives, Brian Balfour writes on the Reforge Blog about how AI is causing what he calls “product-market fit collapse.” He argues this rapid unspooling of a company’s market position is due to AI products that increase user expectations by orders of magnitude overnight. Whether this is worthy of a new phrase or could just be described as rapid disruption is up for debate, but take a look at Balfour’s guidance on how to tell if your company is at heightened risk (or poised to capitalize on it).

Communications Shakedown // Whether you want to think about it or not, communication matters. Having a deliberate comms policy can make a huge difference in overall productivity for a team (even a team of 2). Abhik Pramanik, Co-founder of Ashby, writes about how their small team does big things without working more than 40 hours a week by focusing on deliberate communications. Since this post in 2021, Ashby has raised their Series’ B and C and is gobbling up market share.

Exit Strategies // Ever wondered what happens to all that stuff when a startup shuts its doors? SFGate writer Stephen Council profiles Silicon Valley Disposition, a bay area company that has auctioned off the planes, cranes, and bioreactors shuttered companies no longer need.

Thanks for reading. See you next week.