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

Summary Notes


In this episode of "20 minutes VC," host Harry Stebbings interviews Matt Mochary, a renowned coach to top venture capitalists and founders. Mochary shares his journey from an investor at Spectrum Equity Investors to co-founding Totality, which was sold to MCI Verizon, and his transition to coaching after realizing the impact he could have without the operational burdens of running a company. He discusses his coaching philosophy, emphasizing transparency, vulnerability, and the importance of asking for feedback to build trust. Mochary also touches on the concept of fear and anger in decision-making, the significance of joy as a motivator, and the necessity of aligning one's work with what brings energy and fulfillment. The conversation includes insights on board membership and the value of supporting CEOs with introductions rather than strategic guidance. Mochary advises against lifetime commitments to boards, suggesting that investors focus on providing support that aligns with CEOs' needs. Additionally, the episode features endorsements for various products and services, highlighting their contributions to the tech and business communities.

Summary Notes

Introduction to the Podcast

  • Harry Stebbings introduces the show and expresses appreciation for listener feedback.
  • Harry mentions the special and honest nature of the upcoming discussion with Matt Mochary.

"This is the 20 minutes VC with me, Harry Stebbings and I always love to hear your feedback on the show and you can give that on Instagram at htebings 90 96 with two b's."

The quote is Harry Stebbings opening the podcast and inviting listener feedback, indicating the interactive nature of the show.

Guest Introduction: Matt Mochary

  • Matt Mochary is a coach to top venture capitalists and founders.
  • His clientele includes Peter Fenton at Benchmark, partners at Sequoia, Hemont at GC, and Mamoon at Kleiner.
  • Matt has also worked with founders of high-profile companies like Brex, Coinbase, Plaid, Reddit, and Flexport.
  • Before coaching, Matt was an investor with Spectrum Equity Investors and co-founded Totality, which sold to MCI Verizon.
  • He also produced a documentary and started the Mochary Foundation.

"I'm thrilled to welcome Matt Machari. Matt coaches some of the world's leading venture capitalists and founders, helping them to build the best organizations possible."

Harry introduces Matt Mochary, emphasizing his role as a coach to prominent figures in the venture capital and startup world, highlighting his impact on organizational development.


  • Harry thanks Emmett at Twitch, Zach at Plaid, Emily at Coinbase, Alex at Clearbit, and Henrike at Brex for their question suggestions.

"Thank you to Emmett at Twitch for the intro and Zach at Plaid, Emily at Coinbase, Alex at Clearbit and Henrike at Brex for some fantastic questions suggestions today."

Harry is expressing gratitude for the contributions from various individuals, suggesting a community-driven approach to the podcast's content.

  • Harry mentions HelloSign, an e-signature solution acquired by Dropbox, highlighting its user experience focus.
  • Pendo's product performance benchmarks microsite is introduced, offering comparative product analytics.
  • Pilot for bookkeeping is presented as a solution for financial management, allowing founders to focus on their businesses.

"Check out hellosign.com 20 VC to join the thousands of companies and founders, including me, who value fast, secure and simple esignatures."

Harry promotes HelloSign, positioning it as a valuable tool for companies and founders who prioritize efficiency and security in digital transactions.

Matt Mochary's Journey to Coaching

  • Matt details his entry into startups through investment and entrepreneurship during the internet boom of the late '90s.
  • He shares his experience of leaving a secure job to start a company, which despite operational challenges, was financially successful.
  • After various pursuits, Matt returned to Silicon Valley, seeking community involvement without starting a new company, leading to his coaching career.
  • Matt began by coaching Stanford students, then gradually progressed to more established entrepreneurs.

"So I thought, well, maybe I can become a coach. That way I can be involved in all the fun stuff, which is the decision making and the strategic thinking, but I don't actually have to do the work."

Matt explains his rationale for becoming a coach, allowing him to engage in the strategic aspects of business without the operational responsibilities.

Risk Assessment and Decision-Making

  • Matt discusses the challenge of leaving a secure venture path and how fear of missing out (FOMO) influenced his decision.
  • He reflects on the transition from being motivated by fear to being driven by joy in his later years.
  • Matt elaborates on the relationship between fear, anger, and suboptimal decision-making, citing brain physiology and the work of Robert Sapolsky.
  • He describes his approach to managing fear and anger, including relying on others' perspectives and waiting for emotions to dissipate.

"Fear is an incredible motivator and I think that most people, including myself in my earlier days, that was my main motivation."

Matt shares his personal experience with fear as a motivator and implies that it is a common driving force for many individuals, especially in earlier stages of their careers.

Handling Fear and Anger in Business

  • Matt advises on recognizing fear and anger and the importance of not acting on Neanderthal-like thoughts.
  • He suggests outsourcing decision-making to uninvolved parties or waiting until emotions pass.
  • Matt mentions using mental exercises, such as Byron Katie's "The Work," to mitigate unnecessary fear and anger.
  • Once the emotional state is neutral, Matt trusts his thoughts and proceeds with decision-making.

"If anyone around me ever says, matt fear, matt anger, I just go, oops, and I stop, and I wait until that feeling passes, because I know the thoughts associated with it are basically neanderthal thoughts."

Matt describes his practical method of managing his emotional state, emphasizing the need to pause and reassess when alerted to fear or anger by those around him.

Dealing with Lack of Understanding

  • Harry connects the discussion of fear and anger to his own experiences with lack of understanding in complex areas.
  • Matt advises seeking understanding or assistance in areas that cause fear or uncertainty.

"A lot of the fear and anger that I feel today is often correlated actually to a lack of understanding."

Harry relates the topic of fear and anger to his personal challenges with understanding intricate details in his work, suggesting that knowledge gaps can contribute to these emotions.

Fear and Anger in Professional Situations

  • Harry Stebbings experiences fear and anger in a professional context, particularly during complex negotiations.
  • He acknowledges a lack of understanding of granular financial instruments in term sheets, which leads to fear.
  • Matt Mochary emphasizes the importance of internal reflection on how one's actions may have contributed to the situation.

"And it drove a real fear in me in terms of the negotiating stance, because I didn't fully understand bluntly."

This quote highlights Harry's fear due to a lack of understanding of the terms in a negotiation, which affected his confidence and decision-making.

"What did you do to help create that situation?"

Matt Mochary prompts Harry to consider his own role in creating the situation that led to his fear, suggesting that understanding one's contribution can be a step towards resolution.

Strategies to Address Complex Negotiations

  • Harry suggests bringing in external help or trying to understand the complexities as potential solutions.
  • Matt Mochary proposes a more direct approach by being open about one's feelings and lack of understanding to simplify the terms.

"Bring in external help. That's option one. Option two is try and learn and fully come to grips with the granularities..."

Harry lists potential strategies to deal with his lack of understanding in a high-pressure negotiation situation.

"I think in my experience, when I or others that I coach have shared their vulnerability and their true thoughts and their true feelings, that people have become more connected to them and felt closer to them."

Matt Mochary advocates for sharing vulnerability as a means of building stronger connections and potentially simplifying complex negotiations.

The Power of Vulnerability

  • Sharing weaknesses and vulnerabilities can lead to stronger connections with others.
  • Matt Mochary cites Peter Fenton as an example of someone who effectively shares his vulnerabilities to build rapport.

"Within five minutes of any conversation, he will tell you a weakness that he has, and he's not joking about it."

Matt Mochary explains how Peter Fenton's openness about his weaknesses quickly builds trust and likability, which can be a powerful tool in relationships and negotiations.

Provocative Questions and Transparency

  • Matt Mochary believes in encouraging transparency and sharing of negative thoughts within groups to prevent resentment.
  • He suggests that directly expressing negative thoughts can lead to appreciation and resolution.

"I want them to be transparent with each other about their most negative thoughts, because if they withhold those negative thoughts, then they simply just resent each other."

Matt Mochary explains the value of transparency in group dynamics, highlighting that unexpressed negative thoughts can lead to resentment.

The Right Environment for Difficult Conversations

  • Matt Mochary discusses the importance of creating a safe environment for sharing difficult subjects.
  • He references books like "Difficult Conversations" and "Radical Candor" that offer strategies for effective communication.

"The challenge is, of course, is that there's a reason most people don't share negative things."

Matt Mochary acknowledges the challenges people face in sharing negative feedback and the importance of learning how to communicate difficult subjects without triggering defensiveness.

Timing of Transparent Conversations

  • Timing is crucial for radical transparency; it should not be forced upon someone who is stressed or busy.
  • Conversations should be scheduled at a mutually agreed upon time for the best outcome.

"You can't force this upon someone in the middle of them being stressed about another situation or being in the middle of another task."

Matt Mochary stresses the importance of choosing the right moment for difficult conversations to ensure they are productive and not forced.

Handling Negative Reactions

  • Matt Mochary finds resolving conflict enjoyable and suggests naming and expressing the anger to help release it.
  • He believes that making people feel heard about their feelings and thoughts can help them relax and let go of anger.

"I will simply say, hey, I sense that you're feeling a lot of anger right now."

This quote illustrates Matt Mochary's approach to addressing someone's anger by acknowledging and verbalizing it, which can help defuse the situation.

Self-Resolution of Anger

  • Matt Mochary advises on recognizing the cycle of self-criticism and anger, suggesting that these thoughts often originate in childhood.
  • He recommends acknowledging the old pattern and adding a complementary voice that appreciates all parts of oneself.

"What's interesting is you're identifying, you get angry at someone else and then you get angry at yourself."

Matt Mochary points out the cycle of anger and self-criticism that individuals often experience, indicating the need for self-awareness and change.

Impact of Childhood Experiences on Thoughts

  • Matt Mochary posits that most critical thoughts are formed in early childhood, before the age of five.
  • Understanding the origin of these thoughts can help in addressing and changing them.

"So what you'll find is that almost all of these thoughts got created when you were less than five."

Matt Mochary explains that the critical thoughts that affect us as adults often have their roots in early childhood experiences.

Dealing with Self-Doubt and Impostor Syndrome

  • Harry Stebbings shares his feelings of self-doubt and impostor syndrome related to the success of his show.
  • The discussion implies the importance of addressing these feelings, though specific strategies are not outlined in the provided transcript.

Handling and Managing Impostor Syndrome

  • Impostor syndrome is rooted in fear.
  • Overcoming fear involves recognizing where one feels joy.
  • The "energy audit" is a tool to identify activities that energize versus deplete energy.
  • Activities are marked with a red or green marker based on whether they create or drain energy.
  • Patterns emerge from the audit, highlighting energy-draining tasks.
  • Three solutions to handle energy-draining tasks: outsource, eliminate, or redesign the task to be energizing.
  • Repeating the energy audit monthly can lead to a calendar filled with energizing activities, reducing fear and increasing joy.

So again, impostor syndrome is fear. And so you're feeling it. And the way to, I think, overcome fear is to start recognizing where you feel joy and then taking the pieces of the things that you do that you don't enjoy and removing them.

This quote explains that impostor syndrome is a form of fear and suggests that focusing on activities that bring joy and eliminating those that don't is a way to overcome it.

The Energy Audit

  • The energy audit involves reviewing one's calendar and marking each hour with a red or green marker to represent energy levels.
  • Neutral feelings are marked as red, indicating no energy gain.
  • Identifying patterns of reds helps to pinpoint specific energy-draining activities.
  • Three options to handle these activities: outsource, stop doing them, or find ways to make them energizing.
  • It is helpful to have a thought partner during this process.
  • Continuous application of the energy audit over months should result in more energizing activities and less fear.

This is the energy audit. This is where you print out your calendar for the past, let's say, two weeks. And hour by hour, you take a red marker and a green marker and you mark each hour.

This quote describes the energy audit process, which is used to identify whether activities are energizing or draining by marking them with colored markers on a calendar.

Specialization and Division of Labor Among Founders

  • It's not about being good or bad at tasks but about whether one loves them.
  • People typically perform poorly at tasks they dislike because they invest minimal effort into them.
  • A CEO's role includes ensuring all necessary tasks are completed, not necessarily doing them personally.
  • Co-founders can divide responsibilities based on their preferences and strengths, leading to better performance and job satisfaction.
  • A real-life example is given where co-founders, one extroverted and one introverted, split tasks to align with their preferences, resulting in palpable improvements.

So first of all, it's not about whether they're good at something or bad at something, is whether or not they love it.

This quote emphasizes that enjoyment of a task is more critical than proficiency, as love for the task typically leads to better performance.

Being an Effective Board Member

  • Board membership can be career-ending due to the time commitment involved.
  • Boards meet multiple times a year, and attendance can consume a significant portion of an investor's time.
  • Instead of offering board membership, investors should offer support based on what the CEO finds valuable.
  • CEOs value introductions to customers, other investors, and recruits more than strategic thinking due to their deeper knowledge of the company.
  • Asking CEOs how to be most helpful is more effective than assuming what they need.

First of all, know that boards are the death of every great investor.

This quote warns about the potential negative impact of board membership on an investor's career due to the time commitment it entails.

Creating Trust and Intimacy with Founders

  • Trust and intimacy are built through consistently seeking and acting on feedback.
  • Written feedback should be requested after every interaction, focusing on what was liked and what could be improved.
  • Responding positively to brutal feedback and declaring actions to address it builds trust.
  • Trust is established quickly when discomforts are addressed and resolved early in the relationship.

So for me, there's one tool and one tool only, which has brought me this, and it's an easy one. So I'm going to share it with you and everyone listening. And that is in every single interaction that I have, whether it's one on one with someone or in a group at the end, I always ask for written feedback.

This quote highlights the importance of consistently seeking written feedback to build trust and improve relationships.

Discerning Valuable Feedback

  • Feedback should resonate with the recipient for it to be considered valuable.
  • Not all feedback needs to be accepted, but it should be acknowledged and reflected back to show understanding.
  • Co-creating actions for feedback that resonates helps mitigate future issues.
  • The tyranny of the feedback giver is avoided by not accepting all feedback.

It's whatever resonates with you.

This quote advises that feedback should be taken into account based on whether it resonates with the individual's own experiences and perspective.

Selection of CEOs to Work With

  • Matt Mochary no longer takes on new coaching clients.
  • Previously, Matt selected CEOs to work with based on personal introductions and successful trial coaching sessions.
  • He created a list of CEOs he was interested in coaching and used referrals to connect with them.
  • Trust-building was a crucial part of the coaching process before further introductions were made.
  • Approximately half of the CEOs introduced to Matt agreed to be coached by him.

"So right now, I'm not taking on any new coaches, but in the past when I have, it really was just sort of a one-time thing."

The quote explains that Matt is not currently looking to coach new CEOs and that his previous method of selection was based on specific opportunities rather than an ongoing process.

"I made a list of the 20 people that I'd be interested in coaching and I shared it with naval."

This quote demonstrates Matt's strategic approach to selecting CEOs by creating a targeted list of potential clients.

Coaching Approach and Personal Balance

  • Matt Mochary's favorite book is "High Output Management" by Andy Grove.
  • The biggest challenge for Matt is finding balance between his coaching passion and family time.
  • In 2019, Matt overcommitted to coaching, which led to neglecting family time.
  • Coaching sessions are energizing for Matt, not mentally draining.

"Balancing in 2019. I was a glutton. I love coaching so much that I took on more and more and more and more and more."

This quote emphasizes the challenge of overcommitment and the need for balance between professional passion and personal life.

Role of a Chief of Staff

  • Matt believes the role of a Chief of Staff is crucial for extending one's capacity.
  • Once all productivity hacks are exhausted, a Chief of Staff becomes necessary.
  • Training a Chief of Staff involves giving them full access to emails, calendars, and meetings.
  • The training period typically lasts one to two months, which allows the Chief of Staff to understand the executive's thought process.

"It is the answer for extending oneself when no other hack remains."

The quote highlights the Chief of Staff as a solution for executives who have maximized their personal productivity and need additional support.

Time Management and Respect

  • Being on time is a sign of respect for Matt.
  • He believes in communicating any delays as soon as possible to show consideration for others' time.
  • The key is not just punctuality but also transparency when delays occur.

"Well, this is just a signal of respect."

This quote underscores the importance Matt places on punctuality as a form of respect towards others.

Seeking Advice and Coaching

  • Matt receives coaching and advice from the CEOs he has coached.
  • These relationships have evolved into reciprocal support systems.
  • CEOs like Sam Altman and Enrique offer Matt guidance in return for his coaching.

"I become very close friends with the people I coach and so they end up becoming, and they often say, hey, Matt, you've coached me so much and helped me so much, I'd like to coach you a little bit."

The quote reflects the deep, mutual relationships that form between Matt and the CEOs he coaches, leading to a two-way exchange of advice and support.

Changing Tech in Silicon Valley

  • Matt believes the tech industry has not fully shared its benefits with society.
  • He encourages his clients to address social issues and give back to the community.
  • Initiatives like Y Combinator's support for social ventures are a step in the right direction.
  • Matt supports the idea of companies pledging 1% to social causes.

"I think that the tech world has received many benefits, and I don't think that we've yet shared those fully enough with the country that we sit in or the world that we live in."

The quote expresses Matt's view that the tech industry owes more to society and should actively work to solve social problems.

Future Plans and Living in the Moment

  • Matt does not have specific ambitions or goals for the future.
  • He focuses on experiencing joy in the present moment and continues activities that bring him joy.
  • His approach to life and work is based on mindfulness and contentment.

"I have no idea because I don't have ambitions or goals anymore. I simply live in the moment of am I feeling joy?"

This quote illustrates Matt's philosophy of living in the moment and basing his actions on the joy they bring, rather than on long-term goals or ambitions.

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