Tools for progress #59
How to finally make something, Shipping fast vs. shipping smart, Sailors and rowers
We (humans) read hundreds of articles on company building, angel investing, and self-management and curate the best ones into a weekly summary—helping founders and operators stay on the top of their game.
Better thinking
Three early strategic decisions about your landlord, investors, and customers determine your entire business trajectory, yet most entrepreneurs accidentally back into these choices instead of making them deliberately.
How to finally make something (5 minute read)
Most people fail to make progress on moonshot pursuits because it means stepping into the unknown and unfortunately, unstructured and ambiguous tasks result in anxiety. Instead, it’s easier to put off the ambition and play fantasy games, substituting the real game of creation with more structured activities. This shows up in several ways like piling up technical books and not actually programming. To disrupt the cycle, you need to play two types of games. The tactical game entails sitting down to actually practice your craft, whereas the long game requires emotionally navigating the turmoil of navigating a project from start to finish. Every day spent absorbed in fantasy games is another day you could have learned how to ride the rollercoaster.
How to practice the skill of agency (3 minute read)
Agency is the ability to get what you want out of life. Thankfully, it’s a learnable skill and the best approach is to practice like a pianist practices scales. Here’s a long list of concrete, actionable ideas for practicing the skill of high agency. Dig in and get started.
Operational tactics
Shipping fast vs. shipping smart (2 minute read)
Founders are obsessed with shipping fast because AI tools make it so easy, but there’s a big difference between shipping to learn something versus shipping just to feel productive. The best teams document why they’re building before they build.
You should be playing with AI agents for marketing (8 minute read)
One founder runs his entire marketing team with 40+ AI agents instead of human hires, handling social media, lead qualification, and complex analysis. What?! This piece walks through how, using relay.app. I’m yet to be convinced that agents produce quality marketing, but they’re getting better. It’s clear that AI agents will offer a massive operational advantage over those still doing everything manually.
Naming software teams (3 minute read)
Software teams often choose overly broad names that create chaos down the line. “Platform Team” gets dumped with everything nobody else wants, while “Blue Team” gets left out of conversations they should own. Strong team names should be specific enough to prevent mission creep and clear enough that 80% of people can route questions correctly without thinking twice.
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Venture investing
20VC’s 24 hour deal (2 minute watch)
Company sourced with AI, term sheet delivered in 24-hours. Are we going to see more of this? Does it all really boil down to speed and capital supply at the end of the day?
Lead investors are taking more of a round (3 minute read)
Lead VCs are taking bigger chunks of funding rounds across all stages. Seed leads went from 52% to 61%, Series A from 54% to 59%, and Series B from 50% to 51% between 2021-2025. This means fewer investors per round and more concentrated power, driven by larger fund sizes and competitive dynamics. Founders need to plan round composition early and understand the trade-offs. And investors, well, game on.
The private market trap edition (2 minute read)
There's $13 trillion trapped in venture capital and private equity funds right now, and it's wrecking America’s system to create new companies. About 70,000 U.S. private companies have received some form of private investment, representing $6.7 trillion of cash from investors. These companies are currently valued at $13.3 trillion. But that value is increasingly trapped, with no way for investors and companies to get liquidity. Funding is now concentrated in a few mega funds writing massive checks to either old unicorns or AI startups.
Managing your career
Don’t be afraid to get dressed (1 minute read)
This is a intriguing one. You don’t have to wear a hoodie and jeans to fit into the startup world. Nor do you have to wear a shirt. What you decide to wear is an expression of you. It’s about having a point of view, a sense of taste, and expressing who you are, authentically.
Sailors and rowers (4 minute read)
There seem to be two distinct models people have for achieving success: sailing and rowing. Sailors follow the wind. Do it right and they can go great distances pretty fast, often without even having to do much work. Rowers don’t care too much about the wind but keep going when it’s easy and when it’s hard. The reality is that most people are sailors because they bounce around from one thing to the next. If you’re a rower and you work with sailors, don’t expect them to keep rowing when the wind shifts. They’ll just sail in another direction when things don’t work out, and if the wind ever brings them back, you’ll see them again.
Super shadows | when strength limits growth (64 minute listen)
Whether you’re navigating subtle shifts or considering a big move, this episode of the Skip podcast hosted by Nikhyl (ex-Meta, Google, Credit Karma) and Carly (ex-Wix, Floodgate) helps you own your superpower and the shadow that comes with it. Tune in.