What makes a board member genuinely valuable to a startup?

Martín Escobari · Nov 11, 2022

Very few boards actually add value; the ones that do are small, diverse groups where the CEO opens up about what genuinely matters to them

40:51 20VC: Why Market Size is Everything | Three Signs of a Bull Market and How To Remain Disciplined | Why Investing is a Young Person's Game | The Secret to Negotiation | Missing a $200M Opportunity in Nubank and more with Martín Escobari, Co-President @ Ge

Trae Stephens · Apr 3, 2024

Gathering a bunch of investors onto your board is a stupid way to get advice; founders should instead seek wisdom informally from trusted people with relevant experience

Good advice is available from founders and VCs, but the board structure isn't the right vehicle for it

29:16 20VC: Founders Fund's Trae Stephens on Why The Most Competitive Deals are the Worst, Why No Company is Successful Because of their VC, Why We are Making ZIRP Mistakes Again Today, Why Loss Ratio is BS and Upside Maximisation is Everything

Harry Stebbings · Apr 4, 2026

Most boards today are mostly useless

He finds sitting on them exhausting, and AI is a top agenda item everywhere without adding insight

10:30 20VC: Hims & Hers: $4.3BN Market Cap on $2.3BN of Revenue: The Comeback | Why Being Public is 10x Better | The Death of the "Strategy" Hire | Why Performance Marketing is Worse than Brand Marketing with Andrew Dudum

David Schneider · Sep 11, 2024

When interviewing potential board members, select for hands-on operating experience rather than a record of sitting on other SaaS boards

There are now enough people in venture and growth with real operating experience that you can demand it; you want a mix

Scope: some board issues do belong in the meeting itself; you want a nice mix

51:05 20VC: Scaling ServiceNow to $5BN in ARR | Leadership Lessons from Doug Leone, Frank Slootman and Bill McDermott | VC Value Add: Is it Real and Why the Worst VCs are "Seagull VCs"

Alex Bouaziz · Oct 22, 2025

Alfred Lin is one of the best investors in the world and the board member Alex would most want to add

He cares about founders in a rare way, understands businesses more deeply than most board members want to, was an operator himself, and Alex saw his significant impact firsthand at Cursor and DoorDash

66:49 20VC: Deel CEO Alex Bouaziz on Raising $300M+ at a $17BN Valuation | Deel vs Rippling: WTF is Going On | Management Lessons from Ben Horowitz and Nik Storonsky | Deel's M&A Playbook: Lessons from 13 Acquisitions: What Works & What Doesn't

Amjad Masad · Apr 25, 2026

Replit's board needs an operator who has taken a company public and scaled far beyond his current stage, because it is currently all VCs

The board has many excellent VCs but no one who has actually operated and built a company from scratch through to public markets

Scope: about a board seat he does not yet have filled

39:53 20Product: Replit CEO on Why Coding Models Are Plateauing | Why the SaaS Apocalypse is Justified: Will Incumbents Be Replaced? | Why IDEs Are Dead and Do PMs Survive the Next 3-5 Years with Amjad Masad

Jeff Jordan · Jan 16, 2023

Boards should stay off topics like product design and board members should opine surgically and empathetically rather than talk for airtime

He had an OpenTable board member who wanted to design the product, which was unproductive; having sat in the founder's chair he knows it's a hard chair, so you pick only the topics where you have something new to say

36:17 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

David Schneider · Sep 11, 2024

A board member's job is to identify their own single spike or superpower and leverage that on behalf of the companies they work with

Everyone has a superpower, so value comes from applying it rather than trying to be generally useful

53:13 20VC: Scaling ServiceNow to $5BN in ARR | Leadership Lessons from Doug Leone, Frank Slootman and Bill McDermott | VC Value Add: Is it Real and Why the Worst VCs are "Seagull VCs"

Chad Peets · May 23, 2026

The best board members have deep expertise in one specific area, engage with the company between board meetings, and stay in their swim lanes rather than opining on domains they don't know

Combining real knowledge of the business with genuine expertise is what creates value; VCs who know nothing about sales chiming in on sales adds nothing

40:36 20Sales: The $100M CRO Bubble: Why Anthropic Are Causing a Comp Crisis | Why You Should Never Hire From Salesforce or Service Now | How to Hire, Train and Forecase in a World of AI with Chad Peets and Chris Degnan

Jake Gibson · Jul 14, 2023

Boards are generally not very helpful; real support happens in the weekly one-on-one founder relationship, not the structured board meeting

Boards are a different, structured beast, though they do let founders sit back and reflect on the business once a quarter

Scope: boards are effective for quarterly reflection

36:01 20VC: Why Fund Sizes Should Be Smaller, Should Founders Also Have Their Own Funds, Is Emerging Markets Investing Gone, Is Fintech Investing Dead & Who Will Be The Winners and Losers in VC in the Next 10 Years with Sheel Mohnot, Co-Founder @ BTV

Akshay Kothari · Sep 18, 2024

A board should be designed like an executive team — roughly five seats (CEO whisperer/coach, audit chair for the CFO, a go-to-market operator, a governance/compensation person paired with head of people, and an investor for macro perspective) so each board member is effectively a one-to-one coach for an executive

Designed this way, board members invest in the executives' growth through each phase of their careers; it comes from first-principles thinking

Scope: acknowledges this is probably rare and he knows no other company doing it

35:22 20VC: Notion's Founder on "Founder Mode": When it Works & When it Doesn't | Why The Way Startups Fundraise & Construct Boards is Broken | Raising at a $10BN Valuation in Peak Bubble Times and How Notion Has More Money Than Ever Before with Akshay Kothari

Chris Degnan · May 23, 2026

John McMahon's value as a board member comes from one-on-one time telling operators they're screwing up before the board meeting, not from talking in the meeting

He spends time understanding the business so you don't walk into the board meeting and look like an idiot

42:00 20Sales: The $100M CRO Bubble: Why Anthropic Are Causing a Comp Crisis | Why You Should Never Hire From Salesforce or Service Now | How to Hire, Train and Forecase in a World of AI with Chad Peets and Chris Degnan

Tony Fadell · Mar 15, 2021

Randy Komisar is the best board member he has worked with, because a great board member is straight with you, sees what others don't, backs you up, tells you when you're screwing up, and lets you make mistakes

Randy did all of those things and remains there for him

45:06 20VC: Tony Fadell "The Father of The iPod" on Mentors, Self-Doubt, Vulnerability, His Relationship To Money, Why Entrepreneurs Need to Be Coachable, Why VCs Need To Be More Direct & Why The First Trillionaire Will Innovate Around Climate Change

Sarah Tavel · May 6, 2024

A board member should not be a founder's cheerleader but should be truth-seeking and push on hard questions, because marginal improvements in decisions, speed and hires compound

Each push can yield a 5% better decision, a 5% faster decision, or a 5% better candidate, and those small differences compound; the goal is helping the CEO become the best version of themselves and pulling future scaling problems into the present

42:44 20VC: Benchmark's Sarah Tavel on Are Foundation Models Commoditising | Why Frontier Models Will Be Closed Source | Why the Value is in the Application Layer | The Future of AI is "Selling the Work" Not the Tools

Dan Siroker · May 15, 2024

The board member worth having is one who is honest and candid and won't shy away from the hard truth to spare your ego

Founders need someone who says what they need to hear rather than protecting them; Elad Gil in particular has done this for him

65:53 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless

Cem Sertoglu · Nov 20, 2024

VCs should be quiet on boards and reserve strong opinions for very carefully chosen moments, rather than generalising aphorisms about how a company's story should look.

Venture is the only asset class where the asset chooses the investor, creating enormous pressure to demonstrate value add — compounded by social media — while every company is unique with its own pace and trajectory; the board member's job is to understand the company and be obsessively prepared.

22:01 20VC: Turning $16.5M into $2.1BN; Lessons from the Greatest Venture Investment in European History: UiPath | Why VC is Not Being Commoditised | Why Price Does Not Matter | Lessons on Loss Ratio, Selling and Signalling with Cem Sertoglu

Oren Zeev · Feb 2, 2026 · hedged

Investors are better served by letting go emotionally when founders mishandle a crisis, staying constructive in board meetings rather than manifesting frustration

He finds it easier than most to detach, which keeps him from getting worked up over things he cannot control

Scope: framed as his own temperament relative to other investors

24:05 20VC: 50% of Funds Will Go Out of Business | Why Growth Expectations Today are BS and Will Not Last | Why Oren Zeev Takes $0 Management Fees But 30% Carry | Why GPs Should Not Tell LPs Their Strategy

Andrew Feldman · May 26, 2026

The kindest and most useful thing investors can do is have empathy for how hard the founder's job is; a board does not need to add pressure, because if the pressure doesn't come from within the founder, the board backed the wrong people

Cerebras had an eighteen-month period burning $8M a month unable to solve the technical problem, and a board that understood not to pile on was what made that survivable

Scope: framed around hardware and unsolved technical problems

56:18 20VC: Cerebras CEO on the Future of Data Centres, Token Costs and Memory | We are Not in an Infra Bubble & Dario Got a Bad Deal with Elon for Compute | Should US Companies Sell to China & Why Most Layoffs are AI Washed with Andrew Feldman

Chris Dixon · Mar 27, 2024

It is relatively easy to be a top-quartile board member simply by not being bad — good governance, showing up in downturns, and not micromanaging

Bad board behavior is common because incentives diverge in downturns — junior investors panicking about a company they championed, funds needing to recover money, late investors with big preference stacks who profit from a quick sale — and board members without relevant expertise give granular product advice

Scope: requires separating the board-member hat from the investor hat

42:14 20VC: a16z's Chris Dixon on Who Will Win the Next Generation of Venture, The Two Ways to Make Great Venture Investments and Find the Best Entrepreneurs & Why AI Will Strengthen the Position of the Incumbents Moving Forward

Shardul Shah · Sep 16, 2024

The best board members do less, because very few things a board does actually matter

New board members are driven by ego, power and the desire to help everywhere, but value comes from a handful of interventions — holding up a mirror to what the founder already said, being the weekend first call, and helping hire (not just fire) executives

36:46 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

Ryan Petersen · Jun 20, 2026

A passive, supportive board that doesn't help much but never hurts is preferable to a highly active, 'really helpful' board

The board's job is mainly to represent investor interests; an active director who is smart and thinks they're smarter than the founder might fire him, whereas his current board poses no such risk

Scope: stated about Flexport's own situation

72:38 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport

Martín Escobari · Nov 11, 2022

Investors should not sit in board meetings nitpicking operational metrics like quarterly working capital targets without understanding the complexity founders are managing

As an operator he found it maddening to be criticised by a 23-year-old investor who did not grasp the difficulty of what the team was doing; life on the operator side is really hard

Scope: framed as advice he gives his own teams

8:35 20VC: Why Market Size is Everything | Three Signs of a Bull Market and How To Remain Disciplined | Why Investing is a Young Person's Game | The Secret to Negotiation | Missing a $200M Opportunity in Nubank and more with Martín Escobari, Co-President @ Ge

Miles Grimshaw · Sep 18, 2023

Investors who don't understand the product or strategy do active harm by imposing procedures and checklists, turning the board into a reporting structure and management burden

He has sat in board meetings where this happened — generic procedures replace instance-specific strategy and become a distraction for the founder

22:49 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

Julio Vasconcellos · Sep 23, 2022

The mark of a good investor partner is how they lean in when the company is in trouble, not how they behave during hypergrowth

Benchmark, General Atlantic and T. Rowe Price supported Peixe Urbano most when it was on the rocks — GA lent analysts to fix the finance function and Henry Ellenbogen opened his Rolodex for M&A and fundraising even when the investment was small and troubled

14:26 20VC: Why Greed is the #1 Enemy of Venture Returns, Why Not Enough VCs Play to Win and Lessons from Scaling to $100M and 1,200 Employees and Then Cratering with Julio Vasconcellos, Founder @ Atlantico

Alex Bouaziz · Feb 1, 2023

A board's value depends on stage and performance: it is most valuable when the company is struggling, and least useful when the company is doing well and moving fast

People who sit with the company once a quarter can't form strong opinions on a fast-moving business, whereas a board with your best interests at heart can navigate you through trouble

Scope: assumes the board actually has the founders' best interest at heart, which isn't always the case

39:25 20VC: From $57M in ARR to $297M in Just 12 Months; Why Speed of Execution is the Most Important Factor to Success, Hiring 2,000 People in 3 Years Remotely & Secondaries; Why, When and How Much To Take Out with Alex Bouaziz, Co-Founder & CEO @ Deel

Pat Grady · Jul 8, 2024

The operators who add most value to founders are those who see their job as being in service to the founder — they listen, ask questions and give direct but loving feedback rather than pontificating about their own operating record.

It is the lack of ego, humility, curiosity, genuine care and genuine desire to help that makes them effective with founders

45:09 20VC: The Sequoia Investment Process | Investing Lessons from Doug Leone, Roelof Botha & Alfred Lin | Sequoia's Framework for Analysing Founders | The True Benefit of Having Sequoia on a Cap Table & Sequoia's Biggest Threat with Pat Grady

Miles Clements · Mar 9, 2026

Ravi at Sequoia is the best board member he has seen in action, and what makes a great board member is demeanour and humility rather than resume

Ravi frames feedback as a polite observation the founder can accept or reject, communicating with wisdom and humility

50:05 20VC: Inside Accel's $4BN Growth Investing Machine | Cursor is Dead is Total BS: Here is Why | What Missing Rippling and ElevenLabs Taught Us | Are $2BN-$10BN IPOs Dead | Why Now is a Great Time to be Thoma Bravo with Miles Clements

Cem Sertoglu · Nov 20, 2024

Board members who are overly eager to demonstrate value add damage board dynamics; the founder always knows the business better, is often smarter, works harder and has more skin in the game, so the investor's job is simply to support them when needed.

Pressure to demonstrate value add makes some board members iterate repeatedly over topics that don't warrant it.

24:45 20VC: Turning $16.5M into $2.1BN; Lessons from the Greatest Venture Investment in European History: UiPath | Why VC is Not Being Commoditised | Why Price Does Not Matter | Lessons on Loss Ratio, Selling and Signalling with Cem Sertoglu

Miles Clements · Mar 9, 2026

There is generally an inverse correlation between how vocal a board member is and how helpful they actually are

The board member who insists on the first and last word and needs to teach the founder something they didn't already know isn't operating from wisdom

Scope: stated as a general tendency, not a rule

50:46 20VC: Inside Accel's $4BN Growth Investing Machine | Cursor is Dead is Total BS: Here is Why | What Missing Rippling and ElevenLabs Taught Us | Are $2BN-$10BN IPOs Dead | Why Now is a Great Time to be Thoma Bravo with Miles Clements

Matan Bar · Feb 11, 2021

The primary value of a board is an external perspective on what to focus on, since founders find it hard to identify the key priority among many competing things

Everyone talks about all the right things all the time; investors not in the day-to-day can say there's too little focus on X or too much on Y, which starts the right conversations

Scope: requires having the right board members

22:26 20VC: Scaling to a $1.3Bn Valuation While in Stealth, The Power of Different Network Effects Within Payment Platforms & How To Leverage Your Board and Investor Base for the Most Value with Matan Bar, Founder & CEO @ Melio

Sebastian Siemiatkowski · Feb 16, 2026

Michael Moritz's distinctive skill is instantly identifying what matters from a huge mass of information, rather than mastery of every detail

Unlike others he interacts with, Moritz can look at everything and immediately isolate the important thing

44:15 20VC: SaaS is Dead: Why Systems of Record Will Die in an Agentic World | What Revenue Multiple Will Software Companies Trade At? | From 7,000 to 3,000: We Need Less People Than Ever with Sebastian Siemiatkowski

Jake Gibson · Jul 14, 2023

The pattern recognition of highly experienced board members is incredibly valuable and younger investors tend to discount it

The best board members he's sat with spoke rarely but were always right, drawing on twenty years of seeing the same situations repeat

36:55 20VC: Why Fund Sizes Should Be Smaller, Should Founders Also Have Their Own Funds, Is Emerging Markets Investing Gone, Is Fintech Investing Dead & Who Will Be The Winners and Losers in VC in the Next 10 Years with Sheel Mohnot, Co-Founder @ BTV

Aidan Gomez · Aug 19, 2024

Mike Volpe is an exceptional board member because he has encountered virtually every problem a founder brings him multiple times before and can say how each instance played out

Depth of repeated pattern experience makes his advice unusually actionable

51:33 20VC: Chips, Models or Applications; Where is the Value in AI | Is Compute the Answer to All Model Performance Questions | Why Open AI Shelved AGI & Is There Any Value in Models with OpenAI Price Dumping with Aidan, Gomez, Co-Founder @ Cohere

Mike Salguero · Apr 5, 2023

The main value of VCs is the external knowledge and adversarial challenge they bring to founders who otherwise operate alone

He keeps a board he doesn't need because he misses investors interrogating him and forcing him to defend his thinking

70:40 20VC: The Memo: Scaling to $600M Revenues with No Venture Funding, The Most In Detail Breakdown of Consumer Subscription Unit Economics & Why D2C and Consumer Subscription is Not a VC Backable Model with Mike Salguero, Founder @ ButcherBox

Davis Smith · Dec 15, 2023

VCs add tremendous value beyond capital — having brilliant minds around the table leads to better decisions

He has built companies both with and without investors and found the value-add of investors to be a game changer

33:10 20VC: Cotopaxi: From Selling $6M of Pool Tables to Scaling $150M in Revenues and Challenging Patagonia, Fundraising Lessons from 100+ Rejections & What Founders Do Not Understand About VC with Davis Smith, Founder @ Cotopaxi

Akshay Kothari · Sep 18, 2024

Charlie Munger would have been the ideal board member because of his long-term thinking about business building

Munger and Buffett exemplify long-term thinking and long-term business building

39:12 20VC: Notion's Founder on "Founder Mode": When it Works & When it Doesn't | Why The Way Startups Fundraise & Construct Boards is Broken | Raising at a $10BN Valuation in Peak Bubble Times and How Notion Has More Money Than Ever Before with Akshay Kothari

Eiso Kant · Oct 7, 2024

Mark Zuckerberg would be the ideal board member for an AGI company because he has demonstrated rare long-horizon conviction, most visibly by sustaining AR/VR investment while the world wanted him to stop

Getting to AGI requires conviction in a technology that will change the world despite disagreement, and Zuckerberg has done exactly that from buying Oculus onward — a profile very different from Poolside's current board

59:09 20VC: Raising $500M To Compete in the Race for AGI | Will Scaling Laws Continue: Is Access to Compute Everything | Will Nvidia Continue To Dominate | The Biggest Bottlenecks in the Race for AGI with Eiso Kant, CTO @ Poolside

Harry Stebbings · Nov 21, 2022

Board member utility is barbelled: elite Series A investors and pre-IPO investors add real value, while in the middle a founder is better served by great operators and functional leads than by a Series C or D investor

Early board members like Fenton, Gurley, Alfred Lin or Pat Grady add value at the A, and pre-IPO investors set you up for public markets; the middle stage adds less

45:57 Board value is barbelled early a round and pre ipo investors add most value middle stage adds least

Jason Fried · Jan 6, 2023

The ideal third board member would be someone with a radically different but convincing perspective who pushes back, not someone similar who encourages you to do what you already want

He and David mostly agree, so the value lies in hearing a viable alternative they never would have seen; insights are the most interesting things in the world

38:28 Board member should offer a different convincing perspective not agreement

Michael Eisenberg · Feb 8, 2021

A board member's main job is to bring a network and a forest-level view the founder can't access, not to cite what other portfolio companies did

The founder is focused inside their own business; a network gives repeat iterations of the game applied to this specific entrepreneur, while 'I saw another company do this' is annoying to founders

28:06 Board members value is network and outside perspective not citing other portfolio companies

Brad Feld · Sep 30, 2019

A new early-stage board member should look for ways to work with founders and be useful to them, rather than adopt a one-up/one-down posture of being responsible for an abstract set of governance duties.

That approach makes you a contributor to the company's growth instead of someone who either free-rides on success or becomes part of the problem.

31:32 Avoid governance only posture and instead contribute to founder and company growth

Reid Hoffman · Dec 7, 2020

A board member mistake to avoid is giving casual feedback to employees that gets taken as operational direction; board members should explicitly disclaim operational authority and tell people to coordinate with the company

Knowledge is a spectrum — sometimes you know more than anyone in the room, sometimes nothing, often you know one part but not another — and the board seat's importance tempts people to speak past their knowledge

8:47 Board members should disclaim operational authority when giving casual feedback to avoid being misread as directives

Reid Hoffman · Dec 7, 2020

The best board members combine depth of domain knowledge with depth of self-knowledge — clarity about what they know versus what they're merely speculating about

Michael Volpi signals when something is a default case you must follow versus when he's throwing a dart at the board, and in the former case he is reliably right

40:58 Combining domain expertise with clarity about certainty level of advice defines valuable board members

Brian Halligan · Jan 15, 2024

If your VCs haven't built companies or have thin pattern matching, a strong independent board member with relevant operating experience is worth its weight in gold

HubSpot's first independent, Gail Goodman of Constant Contact, gave timely operational guidance and could back off VCs who were grinding the CEO too aggressively because they were intimidated by her

60:37 Independent operator board member offsets vcs lack of operating experience and shields the ceo

Fabien Pinckaers · Feb 12, 2025

His board is worthwhile because the investors are good, even though preparing presentations is a poor use of his time

He would rather work on product, marketing or salespeople than write PowerPoint

57:15 Board is worthwhile despite heavy personal prep time cost because the investors themselves are good

Fabien Pinckaers · Feb 12, 2025

The board matters far less than the executive committee and team leaders

The people actually doing the work challenge him even more than the board does

66:40 Executive team and leaders challenge the founder more than the board does

Martin Casado · Dec 5, 2022

Board members fall into three types: the average investor board member who is net neutral, the frustrated operator who is disruptive by backseat-driving, and the rare phenomenal board member who has had a big exit and worked the operating urge out of their system

Average investors aren't close enough to product-market fit to add much value; frustrated operators don't realize it's not their company

5:01 Board members fall into three types average neutral frustrated operator and rare phenomenal ones who worked out the operating urge

Martin Casado · Dec 5, 2022

The best junior board members help by doing what only VCs can do — deep market and competitor research synthesized into data for decisions — rather than by giving advice on how to run the company

Founders don't have time to research the space, competitors and people the way a VC who takes meetings all day does; running the company is the founder's job

31:42 Junior board members add value through deep market and competitor research not operational advice

Harry Stebbings · Nov 20, 2024

Venture is a marketing business because capital is the most obvious commodity of all — every fund's money is identical, so each has to make theirs look greener.

If the product is undifferentiated cash, the loud value-add signalling investors do is understandable rather than a lost skill.

24:25 Capital commoditization forces visible value add signalling by investors

Jeff Jordan · Jan 16, 2023

Alfred Lin is an excellent board member because he is thoughtful, does his homework, and brings unique insights

Direct experience partnering with him on the Airbnb board

38:58 Diligent preparation and unique insight define a valuable board member

Mike Salguero · Apr 5, 2023

Creative off-the-cuff ideas like Harry's are exactly what VCs drop into board meetings, creating work for founders already buried in operational problems

The VC may not even have read the deck, but the founder still has to write the idea down and come back on it

44:49 Board members toss out untested ideas creating busywork for founders

Chris Paik · May 8, 2023

A great board's job is to mirror clear thinking back to the founders and leadership, not to give prescriptive advice or introduce net new information.

Like trusted advisors who mostly ask questions, a board helps operators build confidence that they are making the right decision; done well, the role is half therapist, half coach.

61:41 Board mirrors clear thinking back to founders rather than giving prescriptive advice

George Zachary · Oct 12, 2020

A later-stage investor joining a board should not try to replicate the primary founder relationship held by the earliest investors, and should instead add value in an emotional support role

The first or second investor on-site builds the primary relationship and high-bandwidth exchange with the founder; a new investor trying to do the same becomes intrusive on those earlier relationships

30:15 Later stage board investors should add emotional support not replicate the earliest investors primary relationship

Sarah Tavel · May 6, 2024

Board quality is a self-fulfilling prophecy on both sides: founders who believe a great partner matters set a high bar and get one, and investors who believe boards don't matter won't do the work

Founders who have experienced a great (or terrible) investor relationship know it makes a difference and therefore demand it; firms that didn't believe board work mattered would abandon a non-scaling, focused model like Benchmark's

44:21 Board quality is a self fulfilling prophecy for both founders and investors

Sarah Tavel · May 6, 2024

The cliche that you should be embarrassed by who you were six months ago applies to board members as much as to CEOs — a good board member should be visibly improving with every board meeting

She learns how to better partner with founders through every interaction, and long-tenured board seats let you learn from the company's successive stages of scaling

52:09 Board member should visibly improve with every meeting

Nabeel Hyatt · Apr 4, 2025

Board members today need to actually use their portfolio's products and be natively curious about other AI products, rather than watching Twitter and tracking markups

Founders now call about unknowables like what user experience to build as models go multimodal; they want a sounding board, not answers

8:40 Hands on product use and native ai curiosity not market tracking

Davis Smith · Dec 15, 2023

Having credible investors on the board is a game changer beyond capital: it improves founder decision-making and materially helps close and retain top talent

A board member with credibility can jump on a call to close a candidate, and brilliant minds around the table lead to better decisions

33:27 Credible board members help close and retain top talent beyond capital

Davis Smith · Dec 15, 2023

One of the main advantages of a great board is that it surfaces founder blind spots, including whether the founder is still the right person to lead

His board, while proud of his brand-building, told him he would benefit from a president who had scaled a business from $150M to $1.5B — something he had never done

40:22 Great boards surface blind spots including whether the founder is still the right leader

Harry Stebbings · Jan 22, 2024

Part of a board member's and investor's job is to tell founders which people they should not hire

32:58 Warning against bad hires is a core board value add

Bret Taylor · Oct 2, 2024

The core skill of board membership is being involved enough to add value without stepping into operations, and delivering advice in a form the CEO and management team will actually hear

You need an operating cadence that gets you the information required to know where you add value and when something is actually wrong

62:50 Involvement calibrated short of operations plus advice delivered in a form leadership will hear is the core board skill

Shardul Shah · Sep 16, 2024

Boards are invaluable to businesses that want to dominate categories, even though great bootstrapped outcomes exist

In a few strategic moments a valuable board — whether an investor or an independent — is terrific; but companies like Mailchimp show a phenomenal founder can build a beautiful business on no outside dollars

35:57 Boards are valuable for companies aiming to dominate categories though bootstrapped outcomes can succeed without them

Shardul Shah · Sep 16, 2024

Investors become damaging on boards when they put their own interests ahead of the entrepreneur's

An investor seeking near-term liquidity will push overly conservative capital allocation, or push a company into an M&A strategy of buying fallen seed companies that is antithetical to the right strategy — both of which he has seen torpedo businesses

38:45 Investors become damaging board members when they prioritize their own liquidity or ma interests over the founders

David Frankel · Oct 14, 2024

Incumbent attacks follow the same repeatable playbook across sectors, so VCs at any stage can add real value by pre-briefing founders on it and on how to deploy capital against lobbyists, lawyers and PR

The recording industry's attack on Suno mirrors what PillPack faced; because the playbook is identical, it can be taught in advance — like fighting a war across air, land and sea

43:28 Anticipating and teaching incumbent counterattack playbooks is real investor value add

David Frankel · Oct 14, 2024

Jake Saper is the ideal later-stage board member because he takes on very few companies and then involves himself completely through thick and thin.

On Regal he has driven hiring and advice and reversed the company's trajectory, and he sourced Zoom for Emergence.

77:53 Few companies with full involvement defines the ideal later stage board member

Emil Michael · Oct 24, 2022

David Weiden of Khosla Ventures is the best board member he has worked with and is badly underrated

He is a 'polite contrarian' who pushes thinking to the edges with Socratic what-if scenarios rather than to scare, which repeatedly makes founders reconsider and prepare better; he was central to wins like Okta, RingCentral and Square

43:03 Polite contrarian socratic questioning not reassurance makes a board member valuable