Jul 27, 2020 · 47m · 20vc
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 · 14m spoken Jerry Colonna · 10m spoken Harry Stebbings · 10m spoken Tracy Lawrence · 9m spoken
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of TwentyVC, host Harry Stebbings leads a candid panel discussion with Brad Feld, Jerry Colonna, and Tracy Lawrence on founder mental health, depression, and psychological well-being. The guests examine childhood trauma, the trap of milestone-driven happiness, and strategies for dismantling tech culture's toxic perfectionism through radical transparency.
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 23.8% of the talking time here. How this is scored →
Harry as informed peer 1.9 Guest teaching 3.6 Guest disagreement 1.0 Harry pushing back 0.9
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 31:51 Jerry challenges Harry's claim of knowing best
Jerry dryly calls out Harry's claim that he knows best for his mother by asking how long he has been a parent, directly confronting his rationalizations.
Hardest push from Harry ▶ 31:26 Harry refuses Jerry's coaching premiseHarry explicitly rejects Jerry's prompt to let go of control, arguing that realism requires him to override his mother's wishes because he knows best.
Biggest teaching moment ▶ 30:57 Jerry forces Harry into a perspective shiftJerry guides Harry through a psychological exercise, demonstrating that Harry's self-sacrificing behavior directly opposes what his mother actually wants for him.
Harry holds his own ▶ 28:30 Harry articulates the logic behind work justificationHarry demonstrates keen analytical insight by articulating how high achievers construct logical justifications around family care to sustain overwork.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Tracy Lawrence on Founder Isolation and Emotional Breakthroughs | 1 | 1 | 0 | 0 | Harry opens by sharing his personal struggle with bulimia before inviting Tracy to discuss her emotional breakdown during fundraising and learning to express feelings. | |
| Jerry Colonna on Childhood Trauma and Early-Onset Adulthood | 2 | 4 | 1 | 1 | Jerry addresses Harry's question about childhood caretaking by introducing psychological concepts like early promotion and early-onset adulthood, validating Harry's personal story. | |
| Brad Feld on Depressive Episodes and Eradicating Tech Stigma | 0 | 2 | 0 | 0 | Harry prompts Brad for context, and Brad delivers a monologue on his major depressive episodes and his personal mission to eradicate mental health stigma in tech. | |
| Dismantling the Crushing It Culture and Vulnerability in Leadership | 1 | 3 | 1 | 0 | Harry asks about the crushing it myth, and Jerry redirects the prompt to Tracy before deconstructing how the fear of failure creates artificial isolation. | |
| Investor Expectations, Personal Identity, and Flawed Human Leadership | 2 | 3 | 0 | 0 | Harry asks how founders can manage transparency with LPs and VCs, and Brad responds by emphasizing human flawfulness and explaining how idealization creates destructive feedback loops. | |
| The Illusion of Milestones and the Trap of External Validation | 2 | 5 | 1 | 0 | Harry admits to attaching happiness to upcoming milestones, which Brad flatly refutes before Jerry expands using psychological theory and Buddhist principles of non-attachment. | |
| Disentangling Identity from Work and the Cost of Overcommitment | 2 | 4 | 1 | 0 | Harry notes he hasn't taken a holiday in five years due to company identification, prompting Brad to recount how naming his company after himself and overidentifying with work nearly destroyed his marriage. | |
| Reframing Familial Responsibility and Testing New Behavioral Patterns | 4 | 8 | 4 | 6 | Harry defends overworking as necessary care for his ill mother, prompting Jerry and Brad to conduct an active coaching intervention where Jerry challenges Harry's defense mechanisms. | |
| Unconscious Behaviors, Professional Armor, and Owning the Shadow | 2 | 4 | 1 | 1 | Harry brings up drinking as a mechanism for escaping striving, which Brad and Jerry address by encouraging conscious awareness of personal programming and owning one's shadow. | |
| Quick-Fire Insights on Mentorship, Hustle, and Mental Health Realities | 3 | 2 | 1 | 1 | Harry leads a rapid quick-fire round on mentorship, hustle, and mental health myths, with the guests providing brief advice on disrupting constant work habits. |
Statements from this episode (20)
Harry Stebbings: Feelings of inadequacy manifested as severe bulimia
“I think for me, in personal story, it was years of kind of not feeling good enough that manifested itself in a very bad form of bulimia for me.”
Tracy Lawrence: Believing non-founders cannot understand founder struggles is shame-driven
“I sort of felt like I retreated into a shell, and that was a self-created and self-declared shell of, oh, other people can't understand me outside of me building a company because this is uniquely difficult or challenging. Which also isn't true, as I know now,…”
Jerry Colonna: Survived age-18 suicide attempt and late-thirties depression resurgence
“First, after a suicide attempt at 18, I entered therapy, and then later again, as I've shared a number of times in my late thirties, when the depression came back.”
Jerry Colonna: Premature caregiving and early adulthood contribute to mental illness
“At a much earlier age, perhaps, than you were prepared for, you were thrust into a position of being a parent, taking care, being a caregiver. And that's an important statement that you just made, because while it's not the only root cause of mental illnesses,…”
Brad Feld: First major depressive episode lasted two years in mid-twenties
“I had my first major depressive episode when I was running my first company in my mid-twenties, and it was triggered by three things happening at the same time. The first was I ended up getting divorced from my first wife. Our relationship blew up. The second …”
Brad Feld: Mental health stigma creates a personal doom loop for founders
“Realized that there was an incredible stigma around issues of mental health in our society broadly, but especially in the context of entrepreneurship. And that stigma that existed actually made things much, much worse for somebody who was Depressed, and that o…”
Jerry Colonna: Nobody in the tech startup ecosystem is actually crushing it
“What I often say is nobody's crushing it. What's important about that isn't just the sort of deflating of the stultifying and crucifying image that we're all supposed to be crushing it, but it's also the notion that we're not alone.”
Jerry Colonna: Isolating fear of failure converts normal struggle into depression
“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 ourselve…”
Brad Feld: Pressure to present perfection inhibits personal effectiveness and success
“And this idealized state that our culture Has created where you have to carry yourself and present yourself in a certain way is actually a massive inhibitor of people being effective and successful.”
Brad Feld: Processing emotional issues comfortably makes him a more effective investor
“I think the ability to process that stuff in a way that is comfortable for me makes me a much more effective investor.”
Brad Feld: There is zero correlation between achieving milestones and happiness
“There is no correlation. Zero. Between happiness and achieving a milestone.”
Jerry Colonna: Achieving goals often causes anxiety to return even larger
“The problem is that we achieve that goal and then all of a sudden the anxieties come back larger.”
Tracy Lawrence: Hyper-achiever mindset persists even after selling her startup
“To be very real and transparent, I just sold my company earlier this year, and my inner hyper-achiever is is still searching for the next thing.”
Brad Feld: Tying your entire identity to your work is unhealthy
“Linking some of my identity, my work, totally healthy. But my entire identity, not healthy for me at all.”
Brad Feld: Constant entrepreneurial striving is bullshit and causes struggle
“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. What a load of bullshit. And the words themselves kind of make me sh…”
Brad Feld: Tech industry has long suffered from systemic substance abuse
“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, acknowledging it and then understanding what's at the root cause of it, and then some set of people deciding to change, change the…”
Jerry Colonna: Genuine choice in work behavior requires full awareness of trade-offs
“And once you have consciousness, then you have choice. And if you choose to never take a vacation, Harry, do so consciously. If you choose to derive all of your self-worth and meaning from your job, do so consciously and fully conscious of the cost and benefit…”
Tracy Lawrence: Transparently owning personal struggles gives teams permission to seek help
“So I think owning the shadow, whatever it may be, and talking about it with people, starting at least with the people that we feel the most safe with, and then realizing it's totally ok. In fact, it's wonderful, and it gives other people around you permission …”
Tracy Lawrence: Daily hustle culture is unhealthy and must be actively disrupted
“I would say that we should disrupt the hustle, and the way I've been thinking about it now, that I'm on contracts and a little distanced from what I was doing at Choose, is I try to take five minute meditations three times a day. And five pushups and five sit-…”