Advice Aggregated [Perennial Post]

By Alex Mackenzie at

A perpetually evolving doc of the advice I've received or inherited about the craft of investing.

Josh Wolfe was the first person I heard refer to venture as a business of aggregation. In venture we see a lot -- fungal computation to open source contributor models (fan of allcontributors) to gift card breakage state laws.

Below you'll find my ~unique aggregate of learnings about the business of venture - beyond the "usual" / "technical".

  • "People that scare me" - Graham Duncan on hiring Analysts that are capable of being better than you.

  • "Patience is arbitrage" - Mike Maples on the importance of playing long-term games.

  • "In order to make delicious food, you must eat delicious food." - Karri Saarinen on cultivating taste (via Jiro Dreams of Sushi).

  • "Focus on both music making and conducting" - Josh Kushner on how to refine your investment picking whilst management responsibilities scale.

  • "Unique and compelling value proposition" - Pat Grady on gross margins & operating margins.

  • "Suck the oxygen out of the air" - Pat Grady on winning founder mind share. (about Sarah Guo!)

  • "Do good deals" - Anon on becoming a great investor. "Obvious" - but very easy to climb the wrong hill.

  • "Look at the steepness of the slope" - Geoff Lewis on assessing talent.

  • "Rock, sand & water" - Sarah Tavel with a framework on consumers' time allocation.

  • "Not all revenue is created equal" - Bill Gurley on meta financial analysis.

  • "You can still improve an axe" - Jeff Bezos on invention.

  • "Work with life's work entrepreneurs" - Geoff Lewis on investing in upside & resiliency.

  • "What's the last step" - Palmer Luckey on how to avoid working on (or investing in!) incremental ideas.

  • "10**9" - Roelof Botha on investing exceptionally vs. incrementally.

  • "World's most important companies" - Bryan Singerman. "Obvious" - but useful way to keep incremental bias/adverse selection in check.

  • "Study Burning Man" - Jess Lee on building / appraising communities.

  • "Builder & Persuader" - Mike Maples on profiles of co-founders to look out for.

  • "Failure to imagine failure" - Josh Wolfe on company failure being ok as long as the cause of failure was anticipated.

  • "Bat-signal" - Marc Andreessen on Peter Thiel optimizing for the type of founders, colleagues, peers he wants to work with.

  • "There are big markets, large markets and infinite markets" - Josh Kushner on pursuing the grandest investment opportunities.

  • "Sell what LPs know how to buy" - Paul Martino on fundraising narratives for emerging managers.

  • "N-of-1 vs. 1-of-N" - Arjun Sethi on investing in companies capable of generating persistent differential returns.

  • "There are operate to win companies or outright innovation companies" - Henry Ward's taxonomy of companies to build / invest in.

  • "Chips on shoulders put chips in pockets" - Josh Wolfe on identifying founder tenacity.

  • "The power of defaults" - Julien Digital on atom-based network effects.

  • "We're very change-aware" - Miles Grimshaw on where to look as abrupt technical / industrial change occurs.

  • "N+1>N" - Eugenio Pace on building depth into a product/company.

  • "Technical logistics companies" - Alex Wang on the value of investing in / building intangible complexity.

  • "An emerging market leader" - Pat Grady on picking.

  • "Their time is already allocated" - Marc Andreessen on the difficulty of capturing consumer attention.

  • "The half-life (t½) of data" - Miles Grimshaw on how to evaluate the relative stickiness of various systems of record.

  • "Look for what sucks" - Josh Wolfe on investing in what matters.

  • "Multi product companies" - Bedrock Capital on assessing the feasibility of second / third acts by companies.

  • "Truth seeking" - Benchmark on due diligence.

  • "Ask the same question, 10 different ways" - Wes Chan on seeking the truth.

  • "Tell me why this can't work" - Keith Rabois on dd in technical areas.

  • "Look for abrupt change" - Bucky Moore on the urgency of demand for a solution (making an interesting investment).

  • "You should build in the hidden layers" - Nir Zicherman on where to look as abrupt technical / industrial change occurs.

  • "The Toothbrush Test" - Robert Playter on Sergey Brin's want for products that can be used daily.

  • "The most important thing is who is the user, and why do they care" - Miles Grimshaw.

  • "What do you uniquely provide that your customer desperately needs?" - Andy Rachleff on product market fit.

  • "Look for products where you can both do your work and talk about your work" - Jake Saper on products capable of becoming platforms.

  • "Your pref stack is both a liability and an asset" - Eric Paley.

  • "Companies that suffer from indigestion" - Miles Grimshaw on the importance of seeking out companies that can compound via 2nd / 3rd acts.

  • "Pay attention to directional arrows of progress" - Josh Wolfe.

  • "Make something people want, before they can buy it" - Palmer Luckey on VR.

  • "Pick one technical moat/differntiator & build a religion around it" - Anon re. technical marketing.

  • "Find out what works and do it" - Charlie Munger on Lee Kuan Yew.

  • "Power to the People" - Rich Barton on building marketplaces.

Pull requests encouraged if you have a learning to share!