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

In episode 3210 of 20 VC, host Harry Stebbings discusses the often overlooked but critical issue of mental health in the startup ecosystem with guests Brad Feld, Tracy Lawrence, and Jerry Colonna. Feld, co-founder of venture firm Foundry Group, highlights the stigma around mental health in entrepreneurship and shares his experiences with depression. Lawrence, founder and former CEO of Chewse, reflects on the personal impact of her startup journey and the importance of addressing mental health for sustained success. Colonna, CEO of Reboot IO and a professional coach, emphasizes the universal struggle with mental health and the damaging effects of striving for unattainable happiness. The conversation reveals the deep connection between personal well-being and professional life, the dangers of linking self-worth to business outcomes, and the value of vulnerability and genuine connection in the venture capital world. They advocate for a more humane approach to entrepreneurship that acknowledges mental health challenges and supports founders beyond just business metrics.

• Harry Stebbings discusses the lack of attention given to mental wellbeing in the founder journey.
• He introduces guests who have experienced and dealt with mental health issues in their professional lives.
• The conversation aims to highlight the significance of mental health for entrepreneurs and the stigma surrounding it.

"So I'm always very proud of the shows we do here at 20 VC, but I don't think we necessarily always touch on some of the most important and meaningful topics, and I was very pleased to do the episode on alcohol and drinking last month. And today I have an incredible group of people to discuss depression and mental wellbeing, such a core part of the founder journey that I don't think maybe gets enough airtime and spotlight."

The quote emphasizes the importance of discussing mental health issues, which are often overlooked in the entrepreneurial community.

• Tracy Lawrence opens up about her emotional struggles while fundraising as a founder.
• Jerry Colonna shares his lifelong challenge with mental health and the role his family background played.
• Brad Feld recounts his first major depressive episode during his mid-twenties and subsequent experiences with depression.

"Probably when I was running my second financing... it was just one of the most depressing times that I ever went through... if I continue to not address my mental health, I can't continue doing like living out the big vision that I want in the world."

Tracy's quote highlights the intense emotional toll that fundraising can have on founders and the importance of addressing mental health to achieve their visions.

• Tracy Lawrence talks about the support she received from her co-founder during tough times.
• She emphasizes the cultural barriers to discussing feelings and the relief of being able to express emotions openly.

"Luckily, my co-founder... was kind of my spiritual sage... he was sort of the first person to tell me, oh, you know, it's okay to cry. It's okay to feel sadness."

Tracy's quote underlines the value of having supportive relationships in the workplace that encourage emotional expression and wellbeing.

• Jerry Colonna discusses the impact of "early promotion" to adulthood on mental health.
• Both Jerry and Harry Stebbings reflect on their experiences of being thrust into caregiving roles at a young age.

"You experience this phenomena being thrust into early onset adulthood when your emotional body may not have been prepared for it."

Jerry's quote explains how premature responsibilities can contribute to mental health issues later in life.

• Brad Feld shares his decision to be open about his struggles with depression.
• He aims to eliminate the stigma around mental health, especially within the entrepreneurial community.

"I decided to be very open about my struggles as I was depressed and as I was going through this depression... there was an incredible stigma around issues of mental health in our society broadly, but especially in the context of entrepreneurship."

Brad's quote reflects his commitment to transparency and his belief that openness can help reduce the stigma associated with mental health in entrepreneurship.

• Jerry Colonna challenges the common startup ecosystem statement that founders are "crushing it."
• The discussion aims to deconstruct the pressures of appearing successful and the reality behind the facade.

"Jerry, you've said before that no one is crushing it, so I'd love to start on this crushing it statement."

This quote introduces a critical examination of the phrase "crushing it" and its implications for founders' mental health.

• Tracy Lawrence shared an experience of emotional vulnerability when facing potential failure.
• She expressed fear of failing her team and the company, especially given the high expectations set by being in Silicon Valley.
• Her co-founder encouraged her to share her feelings with the team, challenging the notion that leaders must always appear strong and fearless.
• Tracy learned that courage is a response to fear and that showing vulnerability can be noble.

"And I share with him how devastated I would be not to work with this team and just to be a failure, because we had come to this kind of holy Land of Silicon Valley to start this company, and we would fail before we even felt like we had a running start."

The quote illustrates Tracy's deep emotional investment in her team and the fear of not meeting the expectations of Silicon Valley's startup culture.

"And I think what I've learned from you and from other leaders and living it is that the only reason you have courage is actually as a response to fear, because you actually do feel fear."

This quote emphasizes the lesson Tracy learned about the relationship between fear and courage, and how acknowledging fear can be a part of effective leadership.

• Jerry Colonna comments on Tracy's story, highlighting the importance of recognizing the normality and beauty of emotional vulnerability.
• He criticizes the false narrative that everyone must be "crushing it" and points out that this belief can lead to isolation and depression.
• Jerry suggests that fears of failure are common and should be used to empathetically connect with others rather than to isolate oneself.

"Well, that fear of failure is almost a universal phenomena. And rather than seeing it as a means of actually empathetically connecting with other people in the industry, we inadvertently, and because of the shame producing phenomena, use it to isolate ourselves even further, making what is the typical normal roller coaster struggle into a depression."

The quote reflects on the commonality of the fear of failure and how it can either connect us with others or isolate us, depending on our response to it.

• The discussion turns to the fear of being transparent about personal struggles with stakeholders such as LPs, VCs, and board members.
• Brad Feld argues that everyone is flawed and that the pressure to present oneself in a certain way creates negative feedback loops of loneliness and isolation.
• He advocates for authenticity and believes that entrepreneurs who embrace their true selves tend to be more successful in the long run.

"This notion that you have to present yourself a certain way because everybody else is presenting themselves a certain way, then creates this recurring feedback loop of loneliness, of isolation."

Brad's quote criticizes the pressure to conform to an idealized image of success, which he believes leads to disconnection and loneliness.

• The conversation shifts to the attachment of happiness to milestones and the realization that achieving milestones does not necessarily lead to happiness.
• Jerry Colonna links this to perfectionism and the danger of basing self-worth on external achievements.
• He references William James to explain the detrimental effect of tying self-esteem to the accomplishment of goals.

"It is not failure that annihilates us, but it's when we attach our sense of self worth and self esteem to accomplishment of a goal and then fail to achieve the goal, that we are annihilated."

Jerry's paraphrase of William James underscores the psychological risk of basing one's self-worth on external achievements.

• Tracy Lawrence discusses the challenge of her identity being tied to her company's success and the difficulty in finding happiness outside of professional achievements.
• She emphasizes that milestones do not solve the underlying issues of self-worth and happiness.
• The importance of addressing these issues both before and during the entrepreneurial journey is highlighted.

"And it would destroy me because my identity was in the revenue line."

Tracy's quote reveals the emotional toll of equating personal identity with the company's performance.

"But now, if I have a bad day surfing, all of a sudden, I am no longer worthy or I'm no longer happy."

This quote shows how Tracy's sense of self-worth has transferred from her company's success to her personal hobbies, indicating a deeper issue with self-identity and achievement.

• Tracy Lawrence shares her personal story of being bullied as a child and how it influenced the mission of her company, Chews, which was dedicated to fostering authentic connections over meals in corporate environments.
• Brad Feld reflects on his own experience of his identity being deeply intertwined with his company, Feld Technologies, and the challenges he faced when he sold the company at 28.
• Brad discusses the realization that linking his entire identity to his work was unhealthy and the journey he and his wife, Amy, took to redefine what meaning and identity meant to them.

"So the company was called choose, and my mom is chinese, and my dad is jewish, and my friends called me chewish. And so I called the company chews." This quote explains the origin of Tracy Lawrence's company name, Chews, highlighting the personal connection to her heritage and the playful nature of the name's creation.

"I realized that so much of this company was actually me trying to heal my younger self and anybody that goes through loneliness and bullying." Tracy Lawrence makes a connection between her past experiences with bullying and the mission of her company, demonstrating how personal history can shape professional endeavors.

"My company was named Feld Technologies. How fucked up is that?" Brad Feld shares a moment of self-reflection about how his identity was tied to his company, indicating the complexity and potential issues of such an entanglement.

"I prioritized the next random phone call or one more email or one more meeting over basically everything we did together." Brad Feld recounts a pivotal moment in his marriage that made him realize the negative impact of his work-centric identity on his personal relationships.

• Harry discusses using his mother's illness as a justification to work harder, which Brad Feld challenges by asking if such sacrifices are truly necessary or beneficial.
• Jerry Colonna addresses Harry's childhood programming, suggesting that Harry's pattern of sacrificing for his mother's care may not align with what his mother actually wants for him.

"I'm doing it for you. I'm doing the work to pay the bills." Harry expresses a common rationalization for overworking, believing that it's for the benefit of a loved one, in this case, his mother.

"The more you sacrifice your life, your personal life, and work hard and hard. The more you're going against what your mother wants for you." Jerry Colonna provides insight into the potential misalignment between Harry's actions and his mother's desires, challenging the notion that constant sacrifice is the best way to care for someone.

"There's more to safety than just physical safety. There's mental well being. There's happiness." Jerry Colonna expands on the idea of care to include emotional and psychological well-being, not just physical or financial security.

• Brad Feld and Jerry Colonna discuss the importance of recognizing and breaking free from unhealthy patterns and programming that dictate behavior.
• They encourage experimenting with different approaches to life and work to find a balance that aligns with personal well-being rather than external expectations.

"Try it." Brad Feld's advice to Harry is to experiment with taking time off to be with his mother, challenging his programmed behavior and exploring the impact on both of their lives.

"Stopping striving is pretty enlightening because our programming, as people, as entrepreneurs especially, is that you must constantly be striving to achieve the next goal or the next outcome." Brad Feld discusses the revelation that comes from ceasing the constant pursuit of goals and recognizing the programming that drives such behavior.

• Harry brings up the topic of escapism through drinking as a way to remove oneself from the pressures of work and family, seeking advice on how to handle such tendencies.
• Brad Feld emphasizes the importance of understanding one's emotional responses and the influence of societal and internalized expectations, rather than advocating for or against striving.

"How do you think about that forced removal of yourself from striving and maybe the dangers of it, and how you think about that?" Harry questions the potential risks associated with using escapism as a means to break away from the drive to constantly achieve.

"My last statement is not an advocacy to strive or to not strive. It's to disconnect from the programming." Brad Feld clarifies that his advice is about recognizing and questioning one's ingrained behaviors and motivations, rather than prescribing a specific course of action.

• Recognition of long-standing issues with gender and racial equity in the tech industry.
• The need for acknowledgment and understanding of the root causes.
• Importance of individuals deciding to change their behavior and interactions.

"The last four or five years, have finally come to the fore around gender equity, racial equity."

This quote highlights the recent attention to gender and racial disparities within the tech industry, indicating a shift in awareness and prioritization of these issues.

• Acknowledgment of substance abuse within the tech industry and other business sectors.
• Understanding the underlying causes of substance abuse issues.
• Emphasis on personal change and responsible behavior.

"There has long been a drug and alcohol problem in tech. Not just in tech, but in lots of different parts of business and society."

The quote acknowledges the prevalence of substance abuse problems in tech, suggesting it's a widespread issue that extends beyond the industry.

• Exploration of personal identity separate from professional roles.
• The concept of being 'normal' and its ambiguity.
• The benefits of early life experimentation to find joy and fulfillment.

"I'm going to disconnect from my professional work image now, and I'm going to go be a normal 23 year old."

This quote reflects on the speaker's intention to step away from their professional persona to explore other facets of their identity, suggesting a balance between work and personal life.

• The influence of unconscious factors on life decisions.
• The power of making conscious choices about work and personal value.
• Awareness of the trade-offs between professional success and other aspects of life.

"Until you make the unconscious conscious, it will direct your life and you will call it fate."

Jerry Colonna cites Carl Jung, emphasizing the importance of understanding unconscious drivers to exercise choice in one's life and avoid attributing outcomes to fate.

• Acknowledging and accepting both positive and negative aspects of oneself.
• The role of guilt as a personal motivator and its management.
• Encouragement to share personal struggles and seek support.

"If there is light and shadow in you, you have to own the shadow."

Tracy Lawrence discusses the importance of recognizing and accepting all parts of oneself, including the parts that one might feel guilty about or consider negative.

• The evolving nature of mentor-mentee relationships into peer mentorship.
• The mutual learning and growth that occurs in mentorship.
• The concept of contemporary mentors and shared experiences.

"I would say the essence of the foundation of techstars and how we've evolved it is all around the idea of mentorship."

Brad Feld speaks about the significance of mentorship in his career and the reciprocal learning that occurs in these relationships.

• Questioning the healthiness of the hustle mentality in the workplace.
• Implementing small daily practices to create space and break from constant work.
• The negative impact of hustle culture on daily well-being.

"I would say that we should disrupt the hustle."

Tracy Lawrence challenges the notion that constant busyness is beneficial, proposing intentional breaks to improve mental health.

• Misunderstanding of mental health as a state of constant happiness.
• The harmful pursuit of an unattainable ideal of mental well-being.

"The biggest myth and it actually exacerbates our search for mental well being."

Jerry Colonna addresses the flawed belief that mental health equates to perpetual happiness, which can worsen the quest for mental balance.

• Acceptance of living in unprecedented times.
• Prioritizing self-care amidst external demands.
• Willingness to abandon frameworks that no longer serve personal well-being.

"I'm existing within it."

Brad Feld discusses adapting to the challenges of 2020 by focusing on self-care and reevaluating his organizational frameworks.

• The importance of VCs recognizing the person behind the business pitch.
• The positive impact of vulnerability and personal connection during fundraising.
• The potential for a more human-centered approach in VC interactions.

"I think for VCs, they should check in on the human behind the pitch and probably start by being very vulnerable."

Tracy Lawrence suggests that venture capitalists should engage with founders on a personal level to reduce the mental health toll of fundraising.

• The difficulty of acknowledging one's limitations in helping others.
• The importance of offering presence and empathy over trying to fix problems.
• Managing personal tendencies to overextend oneself in the coaching role.

"I think the hardest thing for me is staying mindful that I can't fix everything or everyone."

Jerry Colonna shares the challenge of remembering that as a coach, his role is to provide support rather than solutions to the struggles of founders.

• Expressions of thanks to the participants for the meaningful discussion.
• Recognition of the effort involved in bringing together the conversation.

"Well, can we say thank you to you, Harry, for pulling the three of us together."

Jerry Colonna appreciates Harry Stebbings for organizing the discussion, highlighting the value of the conversation and the relationships formed.

• Promotion of HelloSign and its acquisition by Dropbox.
• Introduction of Point Card as a valuable tool for everyday spending with rewards.
• Announcement of Pendo's expansion and offerings for startups.

"Hello Sign is an effortless esignature solution used by millions to securely send and request legally valid digital signatures and agreements."

Harry Stebbings endorses HelloSign, emphasizing its ease of use and recent success, which serves as an example of a user-centric product that achieved significant growth and acquisition.