Mar 9, 2020 · 37m · 20vc
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
0:00 / 0:00
gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of The 20 Minute VC, host Harry Stebbings interviews premier Silicon Valley executive coach Matt Mochary on managing fear, anger, and imposter syndrome. Matt shares actionable frameworks for radical transparency, role alignment based on energy audits, and why traditional board seats degrade investor effectiveness.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 39.2% of the talking time here. How this is scored →
Harry as informed peer 2.0 Guest teaching 4.6 Guest disagreement 1.4 Harry pushing back 1.6
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 25:36 Board seats are the death of investors
Matt forcefully argues that board seats destroy investor careers and explicitly advises Harry not to take board seats at all, directly attacking conventional VC practices.
Hardest push from Harry ▶ 25:50 Direct pushback on anti-board modelHarry flatly rejects Matt's anti-board seat thesis by pointing out that taking board seats is fundamental to their firm's business model.
Biggest teaching moment ▶ 17:17 Psychoanalyzing self-critical cyclesMatt educates Harry on how internal self-criticism originates in early childhood before age five, leaving Harry thoroughly impressed and admitting he had no idea.
Harry holds his own ▶ 11:10 Challenging vulnerability risk in dealsHarry pushes back on Matt's recommendation to reveal fear and ignorance to founders, arguing that it risks projecting a lack of experience and weakening authority.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Matt Mochary's Path to Executive Coaching | 1 | 2 | 0 | 0 | Harry welcomes Matt and asks a standard background question about his transition from investing and founding into CEO coaching. Matt warmly describes his career path and how coaching Stanford founders led him up the ladder. | |
| Managing Fear and Anger in Business Decisions | 2 | 5 | 1 | 1 | Matt educates Harry on brain physiology, contrasting the creative prefrontal cortex with the fight-or-flight amygdala using Sapolsky's research. Harry asks operational follow-up questions about how to manage fear and anger once identified. | |
| Navigating Uncertainty and Embracing Vulnerability | 3 | 6 | 2 | 5 | Harry brings up a personal recap deal where unfamiliar legal instruments caused fear. Matt turns the interview into a live coaching session, advising radical vulnerability. Harry challenges this, asking if admitting ignorance reduces perceived authority. | |
| Provocative Questions and Radical Transparency | 2 | 4 | 1 | 1 | Harry asks how Matt gets away with asking provocative questions. Matt outlines his exercise where participants think of their most hurtful thought about another before voicing it to break resentment. | |
| Timing Hard Conversations and De-escalating Conflict | 2 | 4 | 1 | 1 | Harry inquires about the optimal timing and handling of negative reactions during tough feedback conversations. Matt explains how to schedule hard talks and de-escalate anger by voicing exaggerated expletive-laden self-criticism on their behalf. | |
| Understanding Self-Critical Cycles and Early Conditioning | 1 | 7 | 1 | 1 | Harry seeks personal advice on dealing with cyclical anger at himself. Matt psychoanalyzes Harry, reframing the inner critic as a mechanism formed before age five, leaving Harry amazed by the insight. | |
| Tackling Imposter Syndrome with Energy Audits | 1 | 5 | 0 | 0 | Harry admits feeling severe imposter syndrome across his podcasting and fund operations. Matt prescribes his red-and-green calendar energy audit process to eliminate draining tasks. | |
| Aligning Leadership Roles with Personal Passions | 2 | 4 | 2 | 1 | Harry asks whether leaders should fix weaknesses or double down on strengths. Matt reframes the premise, arguing that performance stems from passion and joy rather than technical skill, illustrating with a co-founder role split. | |
| The Strategic Downside of Board Seats | 4 | 7 | 6 | 7 | Matt boldly claims that board seats are the death of every great investor and advises against taking them. Harry directly pushes back, pointing out that this advice completely contradicts the core VC business model. | |
| Building Founder Trust Through Written Feedback | 2 | 4 | 1 | 1 | Harry asks about building deep trust and filtering advice overload. Matt explains his practice of obtaining written feedback after every meeting and separating resonant feedback from feedback to disregard. | |
| How Matt Mochary Selects CEO Clients | 2 | 3 | 1 | 0 | Matt recounts how Naval Ravikant kickstarted his client pipeline through peer recommendations. Harry shifts into a rapid-fire round covering books, chief of staff integration, punctuality, and Valley culture. |
Statements from this episode (16)
Matt Mochary's coaching client list includes partners at Benchmark, Sequoia, and Kleiner
“On the VC side, Matt has worked with the likes of Peter Fenton at Benchmark, Several Sequoia partners, Hemond at GC, and Mamoon at Kleiner, to name a few. As for founders, Matt's worked with the founders of Brex, Coinbase, Plaid, Reddit, Flexport, and many mor…”
Y Combinator historically refused to accept enrolled Stanford students into its accelerator
“They were students, and YC wouldn't even accept them into their class.”
Mochary: Joy is a far greater motivator for founders than fear
“Fear is an incredible motivator, and I think that most people, including myself in my earlier days, that was my main motivation. Now, in my later years, I've learned to replace that with joy, which is an even greater motivator and certainly much more pleasant,…”
Outsource immediate business decisions to uninvolved parties when experiencing fear or anger
“If I have to act immediately, I outsource my thinking to someone else. Someone who's not in fear or anger. So I share the situation with someone who's not part of the situation, and their brain, therefore, is not triggered because it doesn't matter to them, an…”
Benchmark's Peter Fenton discloses a genuine personal weakness within five minutes
“The master of this is Peter Fenton at Benchmark. He, within five minutes of any conversation, he will tell you a weakness that he has, and it's not, he's not joking about it. He tells you a real weakness, and my God, it makes me love him, but I'm not unique in…”
Mochary: Never force transparent feedback on stressed employees without agreed timing
“There has to be, 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. So the key is to simply reach out and say, Hey, I'd like to clear something with you is now an okay time for…”
De-escalate angry colleagues by voicing exaggerated, expletive-laden criticisms of yourself
“And one of the easiest ways is to simply have their anger named and their thoughts named. So I will simply say, hey, I sense that you're feeling a lot of anger right now, and my guess is that some of the thoughts you're having are blank, and then I'll really g…”
Harry Stebbings discloses experiencing imposter syndrome around 20VC and investing
“I have a lot of self-doubt and often feel this kind of intense imposter syndrome, be it through the show and kind of the size of the show, and then also kind of through the fund and investing.”
Conducting monthly calendar energy audits dissipates executive fear within three months
“What you'll find is usually by month three, once you've done this three times, your calendar will be mostly green, mostly energy raising, and you will find yourself, I believe, feeling tremendous amounts of joy, and that fear will likely have dissipated a lot,…”
Mochary: Poor performance stems from disliking tasks rather than lacking skill
“Now, typically, if they're bad at something, it's because they hate it, and therefore it They don't want to do it. They don't want to invest in studying how to do it. They don't want to practice it. So they do it just the bare minimum required, which of course…”
Permanent board seats are the death of every great venture investor
“First of all, know that boards are the death of every great investor. So Be wary. If you sell to founders that when they take your money, you will join their board and be on their board forever. Know that you have just ended your career eventually.”
Startup CEOs need warm network introductions from investors, not strategic advice
“And usually it's not strategic thinking because you have very little information about the company. They're at the company, 30 days a month, 12 hours a day. They have so much more information than you do. But what you have that they don't is you have a network…”
Mochary solicits written feedback on a document after every single interaction
“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, not just verbal feedback, ask everyone to write down on a doc.”
Mochary: Leaders Should Only Accept Feedback That Resonates With Them
“If the feedback is something that does not resonate with you, Then no, you do not need to accept it. I think you do need to say thank you, and you do need to reflect back what it is that they said so that they know that you've heard them, but you don't then ne…”
Train a Chief of Staff by granting total email and calendar access
“The best way to train chief of staff is to give them full access. They have complete access to your email, to your calendar, to every meeting that you're in. So they literally sit beside you, listen in on every call and sit in every meeting. And that lasts for…”