Should leaders and investors openly disclose their own weaknesses and confusion to counterparties?

Matt Mochary · Mar 9, 2020

Sharing your vulnerability and true feelings makes people feel more connected and closer to you, rather than damaging their perception of your competence.

In his experience with himself and the people he coaches, disclosure of real weakness has consistently increased connection; Peter Fenton names a genuine weakness within five minutes of any conversation and is universally loved for it.

Scope: based on his own experience and that of clients

11:20 20VC: Matt Mochary, Coach To Silicon Valley's Leading VCs & Founders on How To Deal with Imposter Syndrome and Self-Doubt, How To Manage Fear and Anger & Why Board Seats Are The Death of Investors

Harry Stebbings · Jul 13, 2020

Vulnerability is a source of strength

He says he has observed it over time

33:40 20VC: Chamath Palihapitiya on Why IPOs and Direct Listings Are Broken, Turning Social Capital Into A Combination of Berkshire Hathaway, Koch Industries and The Red Cross, Why Forecasts Are Worthless, What Creates True Defensibility & Why You Have To Be Pr

Tracy Lawrence · Jul 27, 2020

Feelings like sadness are real and should be expressed rather than suppressed, contrary to how many people are raised

Her co-founder telling her it was okay to cry opened up the possibility that these things were real rather than something to suck in and ignore

4:34 20VC: Brad Feld, Jerry Colonna and Tracy Lawrence on Depression and Mental Health, The Dangers of Tying Happiness To Milestones & Why Fear, Anxiety and Guilt Are Useless Emotions

Jerry Colonna · Jul 27, 2020

Fear of failure is a near-universal experience that could be a basis for empathetic connection, but shame leads founders to isolate instead, turning a normal rollercoaster struggle into depression

Because the phenomenon is shame-producing, people use it to isolate rather than connect

12:57 20VC: Brad Feld, Jerry Colonna and Tracy Lawrence on Depression and Mental Health, The Dangers of Tying Happiness To Milestones & Why Fear, Anxiety and Guilt Are Useless Emotions

Tracy Lawrence · Jul 27, 2020

If there is light and shadow in you, you have to own the shadow — naming it openly to people you feel safe with is what defuses it

When she hid her guilt about taking time off or going to therapy, her mind warped the perception into something shameful; when she said it out loud, people were supportive

Scope: start with the people you feel safest with

38:04 20VC: Brad Feld, Jerry Colonna and Tracy Lawrence on Depression and Mental Health, The Dangers of Tying Happiness To Milestones & Why Fear, Anxiety and Guilt Are Useless Emotions

Harry Stebbings · Jun 28, 2021

A leader showing humanity is infectious and draws more humanity out of their team

33:52 20VC: Twilio's Jeff Lawson on What It Takes To Create a Tribe, How To Create Anti-Fragile Organisations Through Decentralised Decision-Making and Why Values Are Nice But Principles Are Better

Jordan Van Horn · Aug 17, 2022

Leaders create psychological safety by openly sharing their own failures, and a rep who claims to have nothing to work on should be viewed with suspicion

Sharing mistakes is a sign of strength not weakness, and most rep mistakes are ones he made himself figuring out the sales motion two years ago

44:50 20 Sales: Three Reasons Why Sales People Fail | The Two Things That Matter When Hiring Sales Leaders | Why Revenue, Discounting and Price Do Not Matter in the Early Days with Jordan Van Horn, Revenue Leader @ Monte Carlo

Christian Lanng · Sep 27, 2023

Leaders should show vulnerability — naming what they're bad at builds more trust than projecting perfection

American business culture demands you always have the perfect answer, but people trust you more when you admit weaknesses, and it builds real relationships

Scope: applies equally to investors

35:38 20VC: "How Being a Founder Almost Killed Me"; We Have Lied to a Generation of Founders | The Hardest Truths About Being a Founder Revealed | Why AI Co-Pilot is BS, Seat Pricing is Over & User Interfaces are Stupid with Christian Lanng

David Meyer · Nov 1, 2023

The fix for being misread as a leader is to be direct, honest and vulnerable about what's actually going on with you, after which people assume best intent

Every one-on-one relationship is different, so sharing context is what lets people interpret your communication charitably

54:03 20Product: Why You Should Not Go Into Product Management, Why the CEO is Always the CPO, How to Build the Best Product Teams & Why You Should Hire People Who Aren't In Product Already with Databricks SVP Product, David Meyer

Ben Fiechtner · Aug 2, 2024

Performative selling — acting out what you think a salesperson should be — rarely works; authenticity and vulnerability are what let buyers connect and buy

He has seen many performative salespeople fail, while even money-driven or abrasive sellers succeed if they own who they are; openness makes connection easier

45:43 20Sales: 12-Week Step-by-Step Framework to Crush Every Sales Quarter | Moving from SMB to Enterprise: How and When | Verticalised Sales Teams: Why They are a Gamechanger and How to Build Them with Ben Fiechtner, CRO @ Clari

Eran Zinman · Mar 2, 2026

Openness and vulnerability — sharing how you feel, the good and the bad — is the single best relationship practice, with a spouse and with work partners alike

The more you open up and are vulnerable, the more intimacy you create and the better the relationship becomes

Scope: applies to both marriage and work partnerships

63:44 20VC: Monday.com CEO on Is SaaS Dead: Will Everything Be Vibe Coded | Will Systems of Record Become Valueless Databases in an Agentic World | Will LLMs Own the Value in the Application Layer with Eran Zinman

Tracy Lawrence · Jul 27, 2020

Courage exists only as a response to fear; leaders who appear literally fearless are a false mental model

You do feel fear, and the noble thing is overcoming it and still moving toward the goal, not the absence of fear

11:24 20VC: Brad Feld, Jerry Colonna and Tracy Lawrence on Depression and Mental Health, The Dangers of Tying Happiness To Milestones & Why Fear, Anxiety and Guilt Are Useless Emotions

Christian Lanng · Sep 27, 2023 · hedged

The compulsion to be the strong one who carries everyone else is ego-driven male conditioning rather than something actually required of you

His partner told him she doesn't need him to carry her, which reset how he approaches things and freed him to do things for himself

Scope: framed as his personal realization, still adjusting to it

11:07 20VC: "How Being a Founder Almost Killed Me"; We Have Lied to a Generation of Founders | The Hardest Truths About Being a Founder Revealed | Why AI Co-Pilot is BS, Seat Pricing is Over & User Interfaces are Stupid with Christian Lanng

Fernando Fanton · Jul 27, 2025

Leaders should be openly honest about their flaws rather than hiding them

There is no value in hiding things — when people don't know about something like ADHD they take forgetfulness personally and assume you're lying; being open removes that; and confidence with age makes hiding unnecessary

Scope: drawn from his own experience with ADHD

46:34 20Product: Should We Kill the PM Role Entirely | How Does Product Design Change Most in a World of AI | How Do Monzo Build Product Today: What Works, What Does Not | Why Most Product Sucks and What Makes Truly Great Product

Brad Feld · Jul 27, 2020

The stigma around mental health, which is especially strong in entrepreneurship, actively makes depression worse for the person experiencing it

It creates a negative reinforcing loop that becomes a personal doom loop for someone depressed while trying to lead a company

Scope: stigma exists broadly in society but is especially acute in entrepreneurship

8:23 20VC: Brad Feld, Jerry Colonna and Tracy Lawrence on Depression and Mental Health, The Dangers of Tying Happiness To Milestones & Why Fear, Anxiety and Guilt Are Useless Emotions

Harry Stebbings · Jul 27, 2020

Having open conversations like this one is key to removing the stigma around mental health in the startup ecosystem

10:33 20VC: Brad Feld, Jerry Colonna and Tracy Lawrence on Depression and Mental Health, The Dangers of Tying Happiness To Milestones & Why Fear, Anxiety and Guilt Are Useless Emotions

Brad Feld · Jul 27, 2020

Performing a persona because everyone else is performing produces a recurring loop of loneliness and disconnection, since you know your true self while imitating others who are also pretending

Everyone is behaving to look like everyone else who is also not being their true self, so disconnection compounds

14:32 20VC: Brad Feld, Jerry Colonna and Tracy Lawrence on Depression and Mental Health, The Dangers of Tying Happiness To Milestones & Why Fear, Anxiety and Guilt Are Useless Emotions

Marc Andreessen · Mar 30, 2026

Founders have a very hard time finding anyone they can confide in

In practice everybody is tense, nervous and fearful but pretending otherwise, so the pretense is mutually misread as genuine confidence

22:10 20VC: Marc Andreessen on The Future of Venture Capital: Will a16z Go Public | Why Labour Displacement with AI is Wrong | Why Introspection is Dangerous | Why "Diamonds in the Rough" is BS in VC | Why a16z Invested $300M into Adam Neumann

Brad Feld · Sep 30, 2019

The first step for a VC in creating safety for founders is modeling openness through your own behavior and doing the internal work to be authentically yourself, rather than labeling behavior with words like empathy and transparency

He has blogged openly for years about his own depression and anxiety and how he works through it, which models the behavior rather than just naming it

Scope: you don't have to be like him or anyone else

34:29 20VC: Brad Feld on Why Market Size At Early Stage Is Not Helpful, His Biggest Learnings From The Boom & Bust of The Dot Com and How The Best VCs Work For Their CEOs

Jeff Lawson · Jun 28, 2021

Leaders should publicly acknowledge and apologize for their own mistakes inside the company, because that models the behavior the organization needs and buys credibility

Acknowledging mistakes sets the tone that making mistakes is okay so long as they are owned, apologized for, and moved past

32:16 20VC: Twilio's Jeff Lawson on What It Takes To Create a Tribe, How To Create Anti-Fragile Organisations Through Decentralised Decision-Making and Why Values Are Nice But Principles Are Better

Harry Stebbings · Nov 1, 2023

All the great leaders are vulnerable, but past a certain level of prominence you have to embrace being a politician

54:16 20Product: Why You Should Not Go Into Product Management, Why the CEO is Always the CPO, How to Build the Best Product Teams & Why You Should Hire People Who Aren't In Product Already with Databricks SVP Product, David Meyer

Matt Pohlson · Jun 6, 2025

Vulnerability in leadership means picking your moments and being candid about uncertainty, not being totally open every time you feel fear — and leaders sometimes do need to project reassurance

People clue off a leader's energy, so you must be able to work past your own concerns even while being candid about them

Scope: not total openness at every moment of fear

71:25 20VC: The Science of Storytelling: Three Steps to Master the Perfect Story | From Near Death Experience to Unicorn Startup: The Untold Story of Omaze with Matt Pohlson

Christian Lanng · Sep 27, 2023 · hedged

A CEO cannot tell the whole company in a town hall that they are depressed and burned out and unsure they can go the distance

The leader is a symbol; during layoffs and a shift from growth to profitability, everyone else was struggling too, and such an admission would have caused a large chunk of the company to leave

9:52 Confide in a small circle not the whole company

Christian Lanng · Sep 27, 2023

You cannot have a real mental health conversation with investors and board members at a late-stage growth startup

The type of funds, capital managers and people you deal with at late stage leave about as much space for that conversation as Wall Street does, which is not a lot

11:57 Late stage investors leave no space for the conversation

Harry Stebbings · Sep 27, 2023

Founders don't bring their struggles to investors because they don't feel they are allowed to

The structure of the relationship makes founders feel they can't; he does vulnerable public shows partly to signal that they can

35:24 The barrier is perceived permission not reality

Christian Lanng · Sep 27, 2023

It is better to keep showing vulnerability and occasionally get exploited than to protect yourself by becoming a cynic

Losing who you are is a worse outcome than being taken advantage of; people see money and opportunity and will exploit openness

36:24 Openness worth the risk of being exploited

Eléonore Crespo · May 9, 2025

What founders most need is someone who will tell them the truth without fear — a role that can be filled by a sibling or friend, not necessarily a spouse

Honest feedback becomes very rare as your company grows

17:52 Founders need a truth teller who can be a sibling or friend not necessarily a spouse

Matt Mochary · Mar 9, 2020

An investor who doesn't understand complex deal terms should tell the founder directly that they feel fear, don't understand the terms, and would like to invest on terms they do understand.

10:54 Admit confusion directly to the counterparty