Should a firm impose one way of operating on its investment team, or let each member work to their own judgment and strengths?

Vince Hankes · May 3, 2023

Investors can't copy another investor's style and expect to win; you have to find what is authentic to you and evoke that emotion in the entrepreneur

What attracts a founder to one investor differs from another; winning deals is emotional and requires real invested time rather than transactional treatment

41:49 20VC: The OpenAI Memo: Why Invest? Is it too Late to Catch OpenAI? Are OpenAI's Models Truly Defensible? Does the Value in AI Accrue to Incumbemts or Startups - Application Layer/Infrastructure? What Happens with Regulation? with Vince Hankes @ Thrive

Miles Grimshaw · Sep 18, 2023

In a firm with no hierarchy or structure, simply being fully yourself is the hardest thing to do — and the most authentic version of you is the best investor you can be

Without levels or structure there is nothing to perform toward, so the only path is unfiltered authenticity

Scope: specific to a flat, structureless partnership

13:09 20VC: Benchmark General Partner, Miles Grimshaw on The Five Pillars of Venture Capital, Why Data Can Be a Trap When Early-Stage Investing, Investing Lessons from Missing Figma and Plaid & The New Business Model for AI & Why Co-Pilot is an Incumbent Strate

Harry Stebbings · Sep 18, 2023

Many investors don't know who they are as investors, and new hires at top firms should keep doing what they were already doing rather than adapting to the firm

The firm hired them for what they had already done

13:37 20VC: Benchmark General Partner, Miles Grimshaw on The Five Pillars of Venture Capital, Why Data Can Be a Trap When Early-Stage Investing, Investing Lessons from Missing Figma and Plaid & The New Business Model for AI & Why Co-Pilot is an Incumbent Strate

Harry Stebbings · Feb 5, 2024

There is no single right way to invest — different investors succeed with fundamentally different styles, so trying to imitate a style that isn't yours is wasted time.

He spent years trying to be a type of investor he wasn't before realizing some do great one way and some another.

13:41 20VC: The Biggest Misconceptions & Hardest Truths About Seed Investing Today; Why The Best Founders Don't Need You, Why Uncapped SAFEs Are Good, Why Reserves Are Bad, Why Signalling is BS, Why Price Doesn't Matter with David Tisch & Terrence Rohan

Shardul Shah · Sep 16, 2024

Junior investors should not assimilate to a firm's norms to get promoted; trying to be someone you're not sets you up for failure

If your goal is to be the best version of yourself and the firm's goal is to be the best firm on the planet, there is no room for conforming — a culture of belonging means people being themselves

5:00 20VC: Index's Shardul Shah on Why Market Size is a Trap | Biggest Lessons on Pricing from Leading Rounds in Wiz & Datadog | Why Benchmarks & Averages in VC are BS | How Index Makes Decisions and Why Growth & Early are the Same Investing Style

Jeff Jordan · Jan 16, 2023

New board members should learn by observing seasoned board members — identifying who adds value and how — and modelling that behaviour, while noting counterexamples like directors who design product in the board meeting

He learned this way on his first board at Hotwire watching very experienced directors operate

39:24 20VC: a16z's Jeff Jordan on The Ultimate Guide to Investing in Marketplaces, Two Core Features to Look for in All Marketplace Investments, Why Fragmented Supply is so Important & Lessons from Airbnb, Pinterest and Instacart on What Makes the Best Cohorts

Ophelia Brown · Mar 17, 2023

Mickey Malka advised that as a fund founder you must follow your own judgment and do things your own way rather than building for one LP or someone else's template

In the beginning you are so unsure what is right or wrong, and he was fixed on the idea that you just do it your way

9:54 20VC: Why Growth Investors Ruined the Venture Market, Why Marketing in Venture Has No Substance, Why Follow-On Investing Can Damage Returns and The Mistakes VCs Made in the Last 18 Months with Ophelia Brown, Founder @ Blossom Capital

Gili Raanan · Mar 28, 2026

Younger investors should learn what they can from prior generations but ultimately make decisions on their own gut, because nobody knows better than they do

40:25 20VC: The Venture Model is Broken | You Need to be Greedy and Selfish to Win Early Stage Investing | Why Margins Do Not Matter for Early-Stage Startups | The Growth Rate that is Required in a World of AI with Gili Raanan, Founder @ Cyberstarts

Steve Jurvetson · Aug 3, 2020

There is no one-size-fits-all model for success in venture; enormously different cognitive frameworks work, and funds should be built around those personality differences

Watching Gracias operate so differently and effectively showed him that the model he happens to embody is not the only one that makes sense, even though most investors assume theirs is

45:00 20VC: Steve Jurvetson on 20 Years of Friendship with Elon Musk, How To Analyse Market Timing, Why Venture Does Not Scale & Why He Has Never Sold A Share in Any Company He Holds

Katherine Boyle · Oct 1, 2020

There is no one right way to practice venture, and the best firms deliberately let different investing strategies and styles coexist among their investors

She worked at two firms (Founders Fund and General Catalyst) that both take pride in allowing divergent styles, and she saw excellent investors within them practicing in opposite ways

10:41 20VC: What Is Founder Narrative Fit and How to Detect and Invest In It, How To Avoid Consensus Thinking When Investing, Price Sensititivity; When To Pay Up vs Stay Disciplined & From New York Times To General Catalyst; Why Venture and Journalism are Not S

Harry Stebbings · Sep 16, 2024

The biggest mistake people make in venture is copying an investing style that isn't authentically theirs instead of leaning into where they are uniquely great across sourcing, selecting and servicing

After 2,700 shows there is no single right way to do venture; success comes from leaning into one pillar over others

3:56 20VC: Index's Shardul Shah on Why Market Size is a Trap | Biggest Lessons on Pricing from Leading Rounds in Wiz & Datadog | Why Benchmarks & Averages in VC are BS | How Index Makes Decisions and Why Growth & Early are the Same Investing Style

Gili Raanan · Mar 28, 2026

Managing partners should let each team member play to their relative strengths rather than push them to fix weaknesses or conform to one mode of operation

On weaknesses the best case is being as good as the market, whereas exceptional strengths create real advantage and real beta

Scope: accepts the team will each operate differently

43:40 20VC: The Venture Model is Broken | You Need to be Greedy and Selfish to Win Early Stage Investing | Why Margins Do Not Matter for Early-Stage Startups | The Growth Rate that is Required in a World of AI with Gili Raanan, Founder @ Cyberstarts

Nabeel Hyatt · Apr 4, 2025

Writing large checks is compatible with subjective, first-principles investing; what destroys judgment is checklists and internal politics, not check size

Time spent building checklists for what can enter a partnership or working the politics of the org is time taken away from testing whether these founders with this idea will become something great

18:49 20VC: Why To Win in AI, Investors Need to Change Their Approach | Why VC is Run by Principals and Associates and is a Broken System | The Bull Case for Anthropic & Whether Deepseek Changes Their Strategy with Nabeel Hyatt @ Spark Capital

Harry Stebbings · Mar 28, 2026

Imposing your own way of thinking as guardrails on team members is a net negative for them even when it worked for you

He did it himself and found it constrained people

45:09 20VC: The Venture Model is Broken | You Need to be Greedy and Selfish to Win Early Stage Investing | Why Margins Do Not Matter for Early-Stage Startups | The Growth Rate that is Required in a World of AI with Gili Raanan, Founder @ Cyberstarts

Miles Grimshaw · Sep 18, 2023

An unstructured partnership meeting with no agenda, memos, or deal-flow lists works better than a formalized process because it creates space for shared learning and trust

The free-flowing time block builds trust in each other and lets partners learn and share together; if something is important it will get through without being put on an agenda

14:02 Unstructured free flowing partnership meetings build more trust than formal agendas

Everett Randle · Nov 10, 2025

Venture firms should not organize partners by stage or sector; investment decisions should be guided by a small set of north stars (astronomical return potential and being the most meaningful partner to the founder) plus each GP's personal style.

Each Benchmark GP is an equal quarter of the firm with their own preferences, and there are many different paths to 10-30x returns, so rigid stage/sector assignment is unnecessary.

45:48 No stage or sector assignments shared north stars plus personal style

Adam Fisher · Jan 22, 2024

Outsourcing reserve decisions to an independent person on the team is not a good idea, and an investor cannot easily change their style anyway.

It looks obvious only in retrospect over a finite period; changing strategy could erase half his gains and pushes him out of his comfort zone.

51:33 Outsourcing reserve decisions to others is unwise since investors cannot easily change their own style