Business stories

TBM 401: Solving Problems the Hard Way

One of the most formative experiences in my career was working for a leader who did the hard work to shape a couple of workstreams, assign owners, and, most importantly, push us hard to build good habits and tempo. It wasn’t easy, by any means. We operated this way for a full year, and the results were incredible (and personally very rewarding).

How Freelance Designers & Developers Can Be Their Own Advocate

On the other hand, no one has your back when things go wrong. There are no team members to ensure that you’re treated fairly or paid for your work. Raise your hand if a client ever skipped town without paying their bill. Yes, we see you!

Solving Problems the Hard Way

One of the most formative experiences in my career was working for a leader who did the hard work to shape a couple of workstreams, assign owners, and, most importantly, push us hard to build good habits and tempo. It wasn’t easy, by any means. We operated this way for a full year, and the results were incredible (and personally very rewarding).

Growth Is Now a Trust Problem

All of us are fighting a war on three fronts (thanks to AI). Customer product expectations are higher than ever. Distribution channels are collapsing. And everyone – big incumbents, new startups, even your own customers with vibecoding – are coming for your value prop.

The Invisible Work

I am generally curious about the concept of legibility of work. Look around in your workplace. You can find documents, messages, presentations, design files. Evidence of people’s work. While it may look like a lot, there is a whole other type of work that is very hard to see. The invisible work.

Strategic Portfolio Management Meets Product-Centricity

For portfolios of assets, we use the terms liquidity and fungibility to describe how easily assets can be converted into cash without materially affecting their price, and how easily investments can be exchanged for one another or rebalanced across the portfolio.  

Why Most Product Teams Aren’t Really Empowered

We’ve all heard the promises. Empowered teams make better products. They’re more engaged, more innovative, and they ship faster. According to Marty Cagan’s definition in his book Empowered, truly empowered product teams are “given problems to solve rather than features to build” and have “the authority to decide the best way to solve those problems.” They’re accountable for outcomes, not outputs.

The Enshittifinancial Crisis

This piece is over 19,000 words, and took me a great deal of writing and research. 

Inside Dribbble’s strategy: From portfolio platform to lead-generating marketplace

We’re nearing the end of a transformative year for Dribbble, during which we reinvented ourselves as a revenue-sharing marketplace and delivered hundreds of thousands of leads – billions of dollars in opportunity – and millions of dollars in payouts to the service providers on our platform.

Why feature roadmaps don’t work for early-stage startups

You are working with a passionate founder. They want to build a product which they are super sure of; they have their pitch deck ready, investors are lined up, and they want to hit market in six months. All they need is a working product: an embodiment of their mission. As a product manager, you do the usual. In a short duration, you conjure up enough details to come up…

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