20VC's Therapist Thursday We Are Not All Crushing It All The Time So Let's Stop Pretending, Working Through Challenges of SelfWorth and SelfDoubt & How To Find Joy in the Striving with Nick Mehta, CEO @ Gainsight



In this episode of 20 VC, host Harry Stebbings discusses the often-overlooked topic of mental health in the venture capital and entrepreneurial space with Nick Mehta, CEO of Gainsight. Delving into themes of vulnerability, the pressure of success, and the stigma surrounding mental health, Nick shares personal anecdotes about growing up feeling like an outsider, his journey with self-development, and the challenges of balancing a high-achieving mindset with personal contentment. They also touch on the importance of instilling work ethic in privileged children and the complexities of identity tied to professional achievements. Harry and Nick's conversation serves as a candid exploration of the emotional landscape that many leaders navigate, highlighting the need for more openness and vulnerability within the tech ecosystem.

Summary Notes

Mental Health Awareness

  • Mental health and awareness are important priorities for the host, Harry.
  • The show 20 VC will focus on discussing mental health, insecurities, and depression within leadership once a month.
  • The importance of acknowledging everyone's hidden struggles is highlighted.

"A friend once told me everyone is fighting a battle you know nothing about and I always think to that one very often."

This quote emphasizes the often invisible personal struggles individuals face, reinforcing the need for mental health awareness.

Nick Mater's Background and Achievements

  • Nick Mater is the CEO of Gainsight, a company focused on customer success.
  • Gainsight was acquired by Vista for $1.1 billion after raising over $156 million from top investors.
  • Nick has been recognized as one of the top SaaS CEOs and has a high approval rating on Glassdoor.
  • Prior to Gainsight, Nick was the CEO of LiveOffice, which was sold to Symantec.

"Last year, as a result of their incredible success, Gainsight was acquired by Vista for a reported $1.1 billion."

This quote highlights the significant achievement of Gainsight under Nick Mater's leadership, showcasing the company's success and impact in its industry.

Equity and Compliance Solutions

  • Carter helps companies issue equity to employees easily.
  • Secureframe streamlines compliance processes for companies, making it quicker to achieve.
  • Cooley is a global law firm that specializes in startups and venture capital.

"More than 16,000 companies issue equity to their employees through Carter."

This quote demonstrates the widespread adoption of Carter's services, indicating its value proposition in the equity management space for companies.

Personal Development and Mental Health Realization

  • Nick realized the importance of mental health through self-development and joining CEO peer groups.
  • Personal development groups can lead to vulnerability and a deeper understanding of oneself.
  • Nick's wife is passionate about mental health, further bringing the topic to the forefront of his life.

"I joined a CEO peer group, international group called YPO Young Presidents Organization... And so I just kind of unearthed a lot of stuff."

This quote reveals how joining a peer group led to personal growth and a greater awareness of mental health for Nick.

Childhood Experiences and Impact on Identity

  • Nick was an introvert and felt unpopular during his childhood.
  • He experienced loneliness and struggled with fitting in at school.
  • Nick's attempts to fit in included trying to adopt the popular trends of the time.
  • His experiences have influenced his adult personality, including his drive to be liked and accepted.

"I ate alone at lunch, which kind of lunch is like the litmus test... It's the litmus test. Like, are you with all the friends around you laughing, or are you on your own?"

This quote conveys the profound impact of childhood isolation on Nick's sense of belonging and social interactions.

The Desire to be Liked and People Pleasing

  • Both Nick and Harry share a tendency to be people pleasers, stemming from a desire to be liked.
  • Nick relates to the concept of being a "mirror ball" from a Taylor Swift song, reflecting what others want to see.
  • The challenge of balancing the desire to be liked with the responsibilities of leadership is acknowledged.

"I absolutely want people to like me and constantly am not sure whether people really like me or not."

This quote captures Nick's internal struggle with self-doubt and the need for external validation.

Real Self vs. Brand Image

  • Nick and Harry discuss the difference between their authentic selves and their public personas.
  • Nick identifies with being an "enneagram three," which characterizes someone who seeks achievement and approval.
  • The conversation touches on the complexity of identity and the difficulty in distinguishing between one's true self and the performed self.

"I'm a three. Like, I'm the most hardcore three you could possibly imagine."

This quote suggests that Nick's personality is strongly aligned with the traits of an enneagram three, which includes a focus on performance and approval-seeking.

Existential Curiosity and Intellectual Interests

  • Nick expresses a deep interest in existential topics, such as consciousness and the nature of the universe.
  • His fascination with physics and the bigger questions of life is a part of his identity that is not always socially engaging.

"I have this part of me that's deeply inquisitive about existentialism... And I'm a big into physics, too, so, like, what the universe is and what time is."

This quote reveals an intellectual side of Nick that is passionate about understanding the fundamental aspects of reality and existence.## Identity and Authenticity

  • Nick Mater discusses the importance of having outlets for different versions of oneself, not just a public persona.
  • Harry expresses concern about losing his own identity to his public brand, "brand Harry," and questions if Nick faces similar challenges.
  • Nick confirms that he does lose himself in his brand and finds genuine moments when with his kids, reading, or exercising, where he's not self-conscious or performing.

"Yeah, I do. And I think that there's a part of my day or my week, where I feel like I have no external self judgment or wondering what people think or thinking about whether I'm successful or not."

This quote highlights Nick's experience of feeling authentic and free from external judgment during certain parts of his day, particularly when with his children.

The Concept of Legacy

  • Nick dislikes the term "exit" when it comes to business, preferring to see new investments as a continuation rather than an end.
  • He discusses how his identity is deeply intertwined with his company, Gainsight, and the difficulty in imagining life without it.
  • Nick references the poem "Ozymandias" by Shelley to illustrate the ephemeral nature of all things, including companies and identities.

"Like, they don't. Do you know Ozzy Medais? Have you heard of Ozzy Medais? Oh, my gosh. You got. Okay, so another. I'm dropping a lot of knowledge here."

This quote introduces the poem "Ozymandias" as a metaphor for the impermanence of achievements and legacies.

The Weight of Responsibility

  • Nick feels a strong sense of responsibility as the leader of Gainsight, likening himself to a train conductor handcuffed to the wheel.
  • He discusses the emotional challenge of seeing long-term colleagues leave the company and the loneliness that accompanies such transitions.
  • Nick acknowledges the pressure and fear of failure that persists even after financial success and investor confidence.

"But I feel like the metaphor I have is it's a train, and I'm the conductor in the front and handcuff myself. To the steering wheel."

The metaphor of being handcuffed to the steering wheel of a train conveys Nick's sense of obligation and inescapability regarding his leadership role at Gainsight.

Loneliness in Success

  • Despite being surrounded by people and activity, Nick experiences loneliness, questioning whether relationships are genuine or based on his position.
  • He feels disconnected when conversations lack authenticity and yearns for more open discussions about shared feelings of loneliness.
  • Nick references the musical "Dear Evan Hansen" as an example of the universal experience of loneliness and the desire for genuine connection.

"But not everyone seems to emote that. And actually, what I've figured out is, actually, those people under the covers do care about it, but they don't always feel open to talking about it."

Nick observes that while many people care about deeper issues, there is often a reluctance to discuss them openly, contributing to a sense of loneliness.

Coping with Mental Health

  • Nick shares his feelings of loneliness with his wife, who is deeply involved in mental health advocacy.
  • He recognizes the importance of not overburdening her and considers therapy as a means to cope with his emotions.
  • The conversation touches on the balance of being open and vulnerable while also managing the emotional load within personal relationships.

"So short answer is yes, but I've learned that I can't do it all because I don't think any partner, it's not like their job to take every single thing you're dealing with."

Nick acknowledges the need to share his struggles but also the importance of not relying solely on his partner for emotional support.

Strength and Vulnerability

  • Harry and Nick discuss the pressure to appear strong for their families while dealing with personal challenges.
  • They explore the balance between being vulnerable and protective of their loved ones, especially when it comes to sharing their own struggles.

"I do feel like that. So I do feel, not that I have to be strong because we're big into vulnerability as a family, but that I probably can't share everything because I don't know if they're ready for it."

Nick expresses his commitment to vulnerability within his family, but also his caution in sharing everything, considering their readiness to handle it.## Vulnerability in Leadership

  • Harry and Nick Mater discuss the importance of vulnerability in leadership and its reception among audiences.
  • Vulnerability is seen as a strength at Gainsight, and Nick has spoken publicly about personal topics such as loneliness.
  • Despite the positive reception, a small percentage of negative feedback can have a significant impact on one's self-perception.
  • Leaders may feel the need to appear confident and strong, but integrating vulnerability can positively influence corporate culture and team dynamics.

"But where what you said makes total sense is at work, I do feel like there is an element of leadership that's about confidence."

This quote emphasizes the traditional view that leaders need to exude confidence to inspire their teams and ensure successful outcomes.

"We're big on it at Gainsight. And a lot of Gainsight people have heard me talk about all these topics, but there's still some veneer of needing to have the story still end up with a positive note."

Nick Mater highlights Gainsight's company culture, which encourages vulnerability in leadership, but also acknowledges the lingering expectation for leaders to maintain a positive outlook.

The Impact of Criticism

  • Leaders, like Nick, can be affected by a small percentage of criticism despite overwhelming support, indicating the human tendency to focus on negative feedback.
  • The discussion touches on the psychological impact of not being universally accepted or praised, particularly when being vulnerable in a professional setting.
  • The challenge of embracing vulnerability is ongoing, and leaders like Nick have to navigate the balance between being open and maintaining an image of strength.

"I always remember those 3% of people or the 1% of people now."

Nick Mater reflects on how a small amount of criticism can overshadow the majority of positive feedback, highlighting the disproportionate weight negative comments can carry.

The Pressure to Be Enough

  • Nick Mater discusses the deep-seated feeling of never being "enough," influenced by his upbringing and immigrant parents' expectations.
  • He shares personal anecdotes about his parents' high standards and the pressure to achieve exceptional success.
  • The conversation delves into the psychological effects of constant comparison and the pursuit of ambitious goals.

"Do I feel like I'm enough? Absolutely not. Not at all."

Nick Mater candidly expresses his persistent feelings of inadequacy despite his achievements, illustrating a common struggle with self-worth.

Parental Expectations and Self-Judgment

  • The discussion explores how parental expectations can shape one's self-perception and the internalization of the need to achieve.
  • Nick Mater recounts stories of his parents comparing him to successful individuals and their direct communication style.
  • The conversation emphasizes the importance of managing one's emotions and judgments in response to external pressures.

"It's my problem. I always feel like, in general, whenever I externalize something and say, oh, that person's not doing enough, or they're telling me to do something, or it's my parents. It's. No, it's me judging myself."

Nick Mater acknowledges that the issue of feeling inadequate is rooted in his own self-judgment rather than external factors like his parents' comments.

The Pursuit of Satisfaction and Happiness

  • The speakers discuss whether achieving milestones and success brings lasting satisfaction and happiness.
  • Nick Mater shares his experiences of transient happiness following achievements and the recurring realization that there is always more to strive for.
  • The conversation touches on the idea that a certain level of dissatisfaction can drive ambition and progress.

"It feels good. So it's actually not like I always feel bad. It's more like I'm always reminded of, like, there's always more."

Nick Mater describes the fleeting nature of satisfaction after reaching goals, suggesting that the feeling of accomplishment is often quickly replaced by new aspirations.

Self-Acceptance and Personal Identity

  • The podcast delves into the concept of self-acceptance and embracing one's unique identity, including perceived flaws and ambitions.
  • Nick Mater discusses the importance of knowing and loving oneself instead of trying to change or hate oneself.
  • He emphasizes the ability to manage and observe one's feelings of inadequacy as a form of personal development.

"I can either know who I am and love who I am or I can hate who I am and try to be something different."

Nick Mater advocates for self-awareness and self-love as the preferable approach to dealing with personal challenges and the pressure to be enough.## Self-Acceptance and Personal Development

  • Embracing oneself is crucial for personal development.
  • The journey of self-improvement leads to becoming the best version of oneself.
  • Acceptance of one's identity without the desire to change is a sign of self-love.

"But I know that I'm not going to change it. And I don't really want to. I love myself. That's the thing. That's the bottom line of this is, as much as all these things sound sad, the development has been for myself. I'm the best version of myself I can be and that's what I want. I don't want anyone else."

The quote emphasizes the speaker's realization that they do not wish to change themselves, highlighting a deep sense of self-acceptance and the culmination of personal growth.

The Role of Money in Happiness

  • The relationship with money is complex and varies from person to person.
  • Money can provide a level of comfort and security, which is a privilege.
  • True happiness often comes from experiences that are free or inexpensive.
  • Empathy for those who struggle financially is essential.

"And so I think there's definitely like a level of comfort that money brings. And I think that's a big privilege for people to have it."

The quote reflects the speaker's understanding that while money can bring comfort and alleviate worries about basic needs, it is a privilege that not everyone has.

Instilling Work Ethic in Privileged Children

  • The challenge of imparting work ethic and ambition in children who are in a privileged position.
  • The desire for children to succeed without feeling undue pressure or inheriting negative traits.
  • Acknowledging that parents have limited control over their children's development.
  • Striking a balance between fostering ambition and allowing children to find their own paths.

"I do think that what I don't want is our kids to just kind of fail to launch in society, meaning they just can't get started. And so we want them to feel that hunger, because I do think the hunger... I think there's some healthiness to it, right?"

The quote discusses the speaker's hope that their children will have the drive to succeed on their own, recognizing that a certain level of ambition is healthy and necessary for personal fulfillment.

Vulnerability in Professional Ecosystems

  • The importance of vulnerability and openness in professional environments.
  • The lack of vulnerability can lead to a sense of loneliness and isolation.
  • Encouraging vulnerability can foster stronger connections and support among colleagues.
  • Vulnerability is seen as a strength, not a weakness, and is key to authentic human connection.

"Vulnerability is infectious. If we all do it, everyone will do it, and then we'll be more real and we'll feel less lonely."

This quote captures the speaker's belief that by sharing vulnerabilities, people can create a more supportive and genuine community, reducing feelings of isolation.

Advice and Self-Reflection

  • The difficulty of following one's own advice, particularly regarding hiring based on values.
  • Self-awareness of the challenges in applying personal beliefs in a professional context.

"The number one thing I say and try to do, but it's so hard, is hiring people based on values and really assessing that mine's being vulnerable."

The speaker acknowledges the challenge of consistently applying the value of vulnerability, both in personal behavior and in hiring practices, despite advocating for it.

Misconceptions of Wealth

  • Wealthy individuals may falsely attribute their success solely to their own efforts.
  • Recognizing the various factors that contribute to success is essential.

"That's a really good one. I would say you made it all happen, that you yourself are the one that made it all happen versus lots of other things that contributed to that."

The quote addresses the common misconception among the wealthy that their success is entirely self-made, ignoring other contributing factors.

Mental Health Stigma in Tech

  • The stigma surrounding mental health discussions in the tech industry needs to be changed.
  • Promoting the idea that discussing mental health is a sign of strength, not weakness.

"It's that talking about this is not a sign of weakness. It's a sign of strength."

The speaker emphasizes the need to reframe conversations about mental health as a demonstration of strength, challenging existing stigmas in the tech industry.

Future Aspirations and Goals

  • The speaker's personal goals include taking their company public and coping with their children growing up.
  • A desire to promote authenticity and a human-first approach in business.
  • Contemplating authorship on topics of vulnerability and authenticity.

"I would love to take gainsight public and I have no idea if it will happen or not, but because certainly there's an ego part of it, there's part that I really believe in our business and I want to do it part about pleasing my parents."

The speaker shares their aspiration to take their company public, motivated by a mix of personal belief in the business, ego, and a desire to make their parents proud.

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