Tools for progress #56
First we shape our social graph; then it shapes us, Venture capital unbundled, Your dreams demand your best hours
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. This week’s issue is a blast from the past so we’ve compiled some of our favorite reads over the last year.
Better thinking
The 100 best bits of advice from 10 years of First Round Review (22 minute read)
100 snappy snippets of some of the very best advice that First Round has shared on their digital pages over the past decade, which wouldn’t have been possible without the incredible entrepreneurs who shared their insights and expertise so that the next generation of builders may succeed. Read on if you’re seeking high signal-to-noise advice to grow as a leader, manage your team, start up, and improve your business or product.
Proof you can do hard things (2 minute read)
For entrepreneurs, mastering difficult challenges creates your greatest competitive advantage. Successfully navigating funding rounds, pivots, or market crashes builds concrete proof of your capabilities, reshaping your professional identity. This explains why some founders with average academic backgrounds outperform brilliant theorists who haven't pushed beyond comfort zones. The most valuable skill isn't domain expertise but developing a ‘figure-it-out’ mindset that makes each future obstacle seem surmountable and opens possibilities that would intimidate others, even your former self.
First we shape our social graph; then it shapes us (9 minute read)
A milieu is the culture contained in your unique set of connections, an ever-evolving graph of information flows between ‘nodes’, people, objects, and ideas that send you input and you send output to. The X or LinkedIn feed you’ve curated is a milieu. Your friend group is a milieu. The startup that you’ve just joined is a milieu. It is by changing your milieu(s) that you change yourself. That’s why it shouldn’t come as a surprise that top performers in many domains spend a great deal of thought on structuring their milieu: whom to interact with, and what work to study and learn from. By assembling a set of influences you can observe and imitate, and peers and mentors that can give you feedback, you’re effectively creating a distributed apprenticeship in the art of being authentically you.
Operational tactics
The future of SaaS is a hybrid of agent, platform, vertical AI (12 minute read)
Despite buzz about AI killing traditional SaaS, the reality looks more like a strategic evolution than a revolution. Enterprise software won’t disappear but transform into hybrid systems where AI agents enhance rather than replace platforms. Big companies still need structured data systems and standardized workflows that DIY solutions can’t match. The most exciting opportunities now exist in vertical AI applications that solve specific industry problems with deep expertise and focused solutions (ahem, Linear).
Too detailed in the wrong ways, not detailed enough in the right ways (10 minute read)
Being "too detailed" isn't about avoiding details, but about providing the right ones for your audience and context. Wes Kao explains how to avoid common pitfalls like overwhelming stakeholders with numbers, neglecting context, or misreading the task. Remember that the goal is to help your audience make sense of information, not just relay data.
How to provide feedback on documents (2 minute read)
Most people need to read this one. At Carta, teams avoided sharing documents widely because processing feedback was too time-consuming. That’s a state of failure, people just need to get better at giving feedback in docs. Here’s a framework. Optimize for helping the author (not your goals), skim first for structure, then go back and add comments with specific details about what, why, and importance level. If the doc is way off, grab time.
Refer and we’ll send you our favorite books as a “thank you” for spreading the word.
Venture investing
Venture capital unbundled (11 minute read)
A deep dive into venture capital's evolving landscape as firms split between two distinct paths: massive asset management operations and smaller, founder-focused "adventure capitalists." As traditional VC firms chase bigger funds and higher deployment velocity, a new wave of investors is breaking away to return to venture capital's roots - focusing on hands-on company building rather than pure asset management.
The Mike Speiser incubation playbook (23 minute read)
Kevin Kwok, a new addition to Sutter Hill Ventures, describes his boss’ approach to VC. Mike Speiser’s VC approach focuses on incubating companies rather than traditional investing, often taking on the interim CEO role. His strategy involves betting on major market shifts, attracting technical co-founders, and providing hands-on support throughout the company-building process. This model has led to notable successes like Snowflake and Pure Storage. According to Kevin, Speiser’s approach is a better way to drive innovation faster, rather than merely being a tollbooth on innovation.
Early-stage VC in the age of vertical AI (8 minute read)
Vertical AI startups are flipping the VC playbook by hitting serious revenue with minimal funding and time. Unlike traditional software, these industry-specific tools slot right into existing workflows, creating consumer-app growth rates in B2B markets. Smart investors are ditching old funding patterns and getting in at company formation instead of waiting for traction signals. Investors have to adapt to this new J-curve capital model and invest earlier and earlier.
Managing your career
Your dreams demand your best hours (2 minute read)
There are hours in a day, and then there are your best hours. Your best hours are the ones where you feel most alive, most energized, most inspired, and most creative. They’re when your focus is sharp, your confidence is high, and your heart is fully in it. And yet too often, we give away our best hours. We give them to tasks that don’t matter to us, habits that don’t serve us, and people who don’t appreciate us. Too often, we treat our best hours like they’re infinite. But they’re a gift - rare, finite, and not to be wasted. So what deserves them? Your dreams demand your best hours. Realizing this is easy but the hard part is still not wasting them.
Our digital feeds showcase endless success stories, creating an illusion that extraordinary achievement is commonplace. In general, society benefits from mass competition where most participants lose, celebrating rare successes to encourage collective hustle. This drives innovation benefiting society but comes at the cost of individuals sacrificing their wellbeing pursuing nearly impossible outcomes. Instead, opt out of this rigged competition by rejecting social approval as your metric and enjoy what others produce, be it books, movies, or technology, while pursuing genuine fulfillment. Greatness will always emerge naturally from people following their curiosity rather than chasing status.
Generalist disease (5 minute read)
Elite professionals often fall prey to the generalist disease, an incorrect model for how to build a successful career. The hallmark symptom is optimizing for optionality, which means chasing breadth and prestige. But they both rapidly turn counterproductive, and people with generalist disease don’t seem to notice. Instead of running after breath and prestige, pursue aptitude and enjoyment. It’s a hard pill to swallow and initially unsettling to take a job you’re not sure is right, or to put your head down and refine the craft rather than continuing to explore options. But it will certainly make you happier to work hard at something you love and are good at.