Tools for progress #62

Don’t drop out of college to launch a startup, The craft of early-stage venture, Career advice worth reading

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.

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Better thinking

Founder mode (18 minute read)

This is a beautiful piece about Kevin Kelly’s approach to work. Known for his writing and future thinking, Kevin likes to work “Hollywood style”. That is, following interests across diverse projects rather than following a sort of linear journey like we’re often told to. He’s also staunchly against this idea that you have to grind the joy out of everything in order to be successful. You can pursue ambitious things without it consuming your happiness. This is a great weekend read.

Don’t drop out of college to launch a startup (2 minute read)

Paul Graham surprised young YC founders by arguing college matters more than the current VC trend of funding dropouts suggests. He believes college offers three irreplaceable benefits: unstructured time for deep thinking, freedom to explore diverse subjects without startup pressure, and relationships beyond tech that spark unexpected insights. How do people feel about that?

Five levels of communication (7 minute read)

Richard Francisco’s Five Levels of Communication is one of the most useful models of human engagement. The model asks “In what ways do we communicate?” and then answers that question by mapping out five ‘levels’ that represent increasing levels of difficulty, risk, and potential learning in our interactions. Although emotions are critically important factors in how we think, communicate, and make decisions, we frequently leave them out of professional conversations because it’s risky and socially taxing. But avoiding touchy feely dialogues about the interaction’s content or even each other means that many issues often go unresolved, or worse, become resolved in a superficial way. To communicate effectively, you need to embrace emotions. Bookmark this read and review every now and then.

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Operational tactics

Skip to the end (2 minute read)

Developers who grew up building traditional software are stuck thinking in databases and forms, but AI changes everything. Instead of creating tools that make users learn complex systems like folder structures or templating languages, smart developers now focus on delivering direct outcomes where users just describe what they want in plain language while AI handles all the messy complexity behind the scenes.

Talking to investors about GTM in 2025 (2 minute read)

Traditional go-to-market playbooks have become investor red flags as channels saturate and costs rise. Smart founders now win by proving they can learn rather than scale, showing scrappy experiments that don't scale and mastering tiny micro-funnels with surgical precision. Your early GTM should be a lab notebook of weird wins, not a polished plan copying someone else's strategy.

To build trust in complexity, offer small choices and fast feedback (2 minute read)

Product simplicity and predictability are a superpower because they give the user a sense of control, a gift in a complicated world. When some things are complex like completing a regulated banking registration, allowing the user to participate in the process by laying out the steps and offering clear feedback after each action can turn their helplessness into relief. This applies to people too. When building a new relationship, with a peer or manager, outline what you’re doing and why. Give them an opportunity to participate and redirect. They’ll soon understand your working style without explanation of each action, leading to a feeling of ownership and greater trust.

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Refer and we’ll send you our favorite books as a “thank you” for spreading the word.

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Venture investing

The consumer manifesto (19 minute read)

Consumer startups are getting unfairly ignored by VCs despite driving venture's best historical returns, with only 7% of seed funding going their way. “Consumer” is really “culture”. The best companies drive or ride the wave of cultural trends. Copycat consumer brands likely won’t be big companies, correct. But the next generation of truly huge companies will probably be consumer. Post also includes a list of 100 angels and VCs backing consumer.

The craft of early-stage venture (77 minute listen)

Peter Fenton is the longest-serving full-time partner at Benchmark, a renowned venture firm known for its artisanal approach and deep alignment with founders. Over the last two decades, Peter led investments in Twitter, Yelp, Elastic, Docker, Zuora, and many others. He sits down with Jack Altman to talk everything early-stage investing.

The beginner’s guide to angel investing (5 minute read)

Now, many of our readers here aren’t beginners, but this is a worthwhile refresher on the basics. When you’re starting out, angel investing works best when you think of it as community building rather than pure financial returns. Small checks function like an expensive MBA, giving you direct learning about business operations and social capital. One of the most important things is to simply not get in the way of the founders.

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Managing your career

Never lose your confidence (4 minute read)

Confidence works like an early warning system for life's major problems. When it starts eroding, everything else follows weeks or months later, from job performance to relationships. Modern consumer culture deliberately undermines confidence to sell solutions, so protecting it means monitoring those subtle shifts and avoiding the endless cycle of manufactured insecurity that keeps you buying fixes.

Career advice worth reading (1 minute read)

Being the very best at something is difficult to do. Being in the top 5-25% in something is much more achievable. When you combine together those disciplines you’re in the top, say, 10% in, you end up creating a combinatorial outcome where you might well be the only (or at least, a member of few) who is uniquely skilled across those combined disciplines. That’s where things get interesting.

How to deliver difficult news (2 minute read)

From Dan Webb, founder of Existent. “Your job is to deliver the message, not to make them feel better in the moment.” Deliver the message concisely, own the decision, answer practical questions about next steps, then end the meeting quickly. Let people process privately rather than drawing out conversations with unnecessary commentary or platitudes.

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