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Nov 4, 2016 · 25m · 20vc

20VC: CEO Whisperer Jerry Colonna on How Investors Mimic Aggressive Behaviour To Cover Insecurity and Why Vulnerability is Key To Success In VC

Jerry Colonna · 15m spoken Harry Stebbings · 8m spoken
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 former venture capitalist and executive coach Jerry Colonna on the psychological challenges of leadership, the hidden insecurities behind aggressive VC behavior, and how radical self-inquiry and vulnerability drive authentic personal and professional success.

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 34.1% of the talking time here. How this is scored →

Harry as informed peer 2.0 Guest teaching 4.2 Guest disagreement 2.2 Harry pushing back 0.7
05100:0010:0020:002:04–5:05 · Harry as informed peer 1/10 Jerry Colonna's Early Career and Entry into Venture Capital Harry asks a broad opening question about Jerry's entry into VC. The tone is relaxed and humorous, particularly when Harry mentions he was born in 1996 while Jerry discusses 1994, leading to playful banter.5:05–8:09 · Harry as informed peer 1/10 Struggle with Depression and Transition to Executive Coaching Jerry shares a deeply personal narrative regarding his struggle with depression and his transition to executive coaching. Harry acts purely as a receptive listener while Jerry elaborates on discovering his coaching superpower.8:09–14:26 · Harry as informed peer 4/10 Psychological Integration, Vulnerability, and Insecurity in VC Harry demonstrates good preparation by quoting Jerry's past interviews and pushes back on how vulnerability fits into aggressive VC term-sheet culture. Jerry passionately reframes compartmentalization and forcefully criticizes VCs who act like bullies out of fear.14:26–18:03 · Harry as informed peer 3/10 The Reboot VC Bootcamp and Radical Self-Inquiry Harry integrates questions provided by Brad Feld regarding VC behavior. Jerry explains the philosophy behind his VC bootcamps, urging investors to examine their own complicity and anxiety.18:04–20:47 · Harry as informed peer 2/10 Quick Fire Round: Books, Mentorship, and Psychoanalysis Harry leads a standard rapid-fire round covering books, mentorship, and personal habits. Jerry remains open and agreeable, sharing that he has worked with the same psychoanalyst for 24 years.20:47–23:20 · Harry as informed peer 1/10 Live Coaching Session: Harry Stebbings on Work-Life Integration Jerry completely turns the interview dynamic around by putting Harry on the spot regarding his own workaholic tendencies. Harry yields entirely, candidly admitting his isolation while Jerry analyzes his defense mechanisms.2:04–5:05 · Guest teaching 2/10 Jerry Colonna's Early Career and Entry into Venture Capital Harry asks a broad opening question about Jerry's entry into VC. The tone is relaxed and humorous, particularly when Harry mentions he was born in 1996 while Jerry discusses 1994, leading to playful banter.5:05–8:09 · Guest teaching 3/10 Struggle with Depression and Transition to Executive Coaching Jerry shares a deeply personal narrative regarding his struggle with depression and his transition to executive coaching. Harry acts purely as a receptive listener while Jerry elaborates on discovering his coaching superpower.8:09–14:26 · Guest teaching 6/10 Psychological Integration, Vulnerability, and Insecurity in VC Harry demonstrates good preparation by quoting Jerry's past interviews and pushes back on how vulnerability fits into aggressive VC term-sheet culture. Jerry passionately reframes compartmentalization and forcefully criticizes VCs who act like bullies out of fear.14:26–18:03 · Guest teaching 4/10 The Reboot VC Bootcamp and Radical Self-Inquiry Harry integrates questions provided by Brad Feld regarding VC behavior. Jerry explains the philosophy behind his VC bootcamps, urging investors to examine their own complicity and anxiety.18:04–20:47 · Guest teaching 2/10 Quick Fire Round: Books, Mentorship, and Psychoanalysis Harry leads a standard rapid-fire round covering books, mentorship, and personal habits. Jerry remains open and agreeable, sharing that he has worked with the same psychoanalyst for 24 years.20:47–23:20 · Guest teaching 8/10 Live Coaching Session: Harry Stebbings on Work-Life Integration Jerry completely turns the interview dynamic around by putting Harry on the spot regarding his own workaholic tendencies. Harry yields entirely, candidly admitting his isolation while Jerry analyzes his defense mechanisms.2:04–5:05 · Guest disagreement 1/10 Jerry Colonna's Early Career and Entry into Venture Capital Harry asks a broad opening question about Jerry's entry into VC. The tone is relaxed and humorous, particularly when Harry mentions he was born in 1996 while Jerry discusses 1994, leading to playful banter.5:05–8:09 · Guest disagreement 1/10 Struggle with Depression and Transition to Executive Coaching Jerry shares a deeply personal narrative regarding his struggle with depression and his transition to executive coaching. Harry acts purely as a receptive listener while Jerry elaborates on discovering his coaching superpower.8:09–14:26 · Guest disagreement 4/10 Psychological Integration, Vulnerability, and Insecurity in VC Harry demonstrates good preparation by quoting Jerry's past interviews and pushes back on how vulnerability fits into aggressive VC term-sheet culture. Jerry passionately reframes compartmentalization and forcefully criticizes VCs who act like bullies out of fear.14:26–18:03 · Guest disagreement 1/10 The Reboot VC Bootcamp and Radical Self-Inquiry Harry integrates questions provided by Brad Feld regarding VC behavior. Jerry explains the philosophy behind his VC bootcamps, urging investors to examine their own complicity and anxiety.18:04–20:47 · Guest disagreement 1/10 Quick Fire Round: Books, Mentorship, and Psychoanalysis Harry leads a standard rapid-fire round covering books, mentorship, and personal habits. Jerry remains open and agreeable, sharing that he has worked with the same psychoanalyst for 24 years.20:47–23:20 · Guest disagreement 5/10 Live Coaching Session: Harry Stebbings on Work-Life Integration Jerry completely turns the interview dynamic around by putting Harry on the spot regarding his own workaholic tendencies. Harry yields entirely, candidly admitting his isolation while Jerry analyzes his defense mechanisms.2:04–5:05 · Harry pushing back 0/10 Jerry Colonna's Early Career and Entry into Venture Capital Harry asks a broad opening question about Jerry's entry into VC. The tone is relaxed and humorous, particularly when Harry mentions he was born in 1996 while Jerry discusses 1994, leading to playful banter.5:05–8:09 · Harry pushing back 0/10 Struggle with Depression and Transition to Executive Coaching Jerry shares a deeply personal narrative regarding his struggle with depression and his transition to executive coaching. Harry acts purely as a receptive listener while Jerry elaborates on discovering his coaching superpower.8:09–14:26 · Harry pushing back 3/10 Psychological Integration, Vulnerability, and Insecurity in VC Harry demonstrates good preparation by quoting Jerry's past interviews and pushes back on how vulnerability fits into aggressive VC term-sheet culture. Jerry passionately reframes compartmentalization and forcefully criticizes VCs who act like bullies out of fear.14:26–18:03 · Harry pushing back 1/10 The Reboot VC Bootcamp and Radical Self-Inquiry Harry integrates questions provided by Brad Feld regarding VC behavior. Jerry explains the philosophy behind his VC bootcamps, urging investors to examine their own complicity and anxiety.18:04–20:47 · Harry pushing back 0/10 Quick Fire Round: Books, Mentorship, and Psychoanalysis Harry leads a standard rapid-fire round covering books, mentorship, and personal habits. Jerry remains open and agreeable, sharing that he has worked with the same psychoanalyst for 24 years.20:47–23:20 · Harry pushing back 0/10 Live Coaching Session: Harry Stebbings on Work-Life Integration Jerry completely turns the interview dynamic around by putting Harry on the spot regarding his own workaholic tendencies. Harry yields entirely, candidly admitting his isolation while Jerry analyzes his defense mechanisms.

speaking balance: gold is Harry, purple is the guest (3 minute bins)

0:00 · Harry 75.9% · guest 24.1%0:00 · Harry 75.9% · guest 24.1%3:00 · Harry 13.8% · guest 86.2%3:00 · Harry 13.8% · guest 86.2%6:00 · Harry 7% · guest 93%6:00 · Harry 7% · guest 93%9:00 · Harry 16% · guest 84%9:00 · Harry 16% · guest 84%12:00 · Harry 17.2% · guest 82.8%12:00 · Harry 17.2% · guest 82.8%15:00 · Harry 24.8% · guest 75.2%15:00 · Harry 24.8% · guest 75.2%18:00 · Harry 36.9% · guest 63.1%18:00 · Harry 36.9% · guest 63.1%21:00 · Harry 58.9% · guest 41.1%21:00 · Harry 58.9% · guest 41.1%24:00 · Harry 100% · guest 0%24:00 · Harry 100% · guest 0%
Sharpest disagreement ▶ 13:30 Fuck the playbook and VC bullying

Jerry forcefully rejects conventional industry logic with explicit language and argues that VCs mimic aggressive behavior as a mask for their underlying fear of losing money.

 Hardest push from Harry ▶ 11:54 Challenging vulnerability in hard-nosed VC negotiations

Harry pushes back on Jerry's call for emotional openness, arguing that VC culture relies on aggressive tactics like hard term sheets and pushing valuations.

 Biggest teaching moment ▶ 21:07 Live coaching tables turned on the host

Jerry steps directly into his coach persona, challenging Harry's work obsession by asking probing personal questions about his happiness and life outside of work.

 Harry holds his own ▶ 8:09 Referencing Jungian quote from Startup podcast

Harry demonstrates strong knowledge and prep by quoting Jerry's exact line from his Gimlet Startup appearance regarding making the unconscious conscious.
the scores for every segment, with the reasoning behind each
ChapterTopicHarry as informed peerGuest teachingGuest disagreementHarry pushing backWhy
Jerry Colonna's Early Career and Entry into Venture Capital 1210 Harry asks a broad opening question about Jerry's entry into VC. The tone is relaxed and humorous, particularly when Harry mentions he was born in 1996 while Jerry discusses 1994, leading to playful banter.
Struggle with Depression and Transition to Executive Coaching 1310 Jerry shares a deeply personal narrative regarding his struggle with depression and his transition to executive coaching. Harry acts purely as a receptive listener while Jerry elaborates on discovering his coaching superpower.
Psychological Integration, Vulnerability, and Insecurity in VC 4643 Harry demonstrates good preparation by quoting Jerry's past interviews and pushes back on how vulnerability fits into aggressive VC term-sheet culture. Jerry passionately reframes compartmentalization and forcefully criticizes VCs who act like bullies out of fear.
The Reboot VC Bootcamp and Radical Self-Inquiry 3411 Harry integrates questions provided by Brad Feld regarding VC behavior. Jerry explains the philosophy behind his VC bootcamps, urging investors to examine their own complicity and anxiety.
Quick Fire Round: Books, Mentorship, and Psychoanalysis 2210 Harry leads a standard rapid-fire round covering books, mentorship, and personal habits. Jerry remains open and agreeable, sharing that he has worked with the same psychoanalyst for 24 years.
Live Coaching Session: Harry Stebbings on Work-Life Integration 1850 Jerry completely turns the interview dynamic around by putting Harry on the spot regarding his own workaholic tendencies. Harry yields entirely, candidly admitting his isolation while Jerry analyzes his defense mechanisms.

Statements from this episode (10)

Assertion Supported
CMP was the third company to sell web advertising in 1994
“We launched all 18 of our magazines on the web. So we were the only the third company to sell advertising on the web.”
Jerry Colonna Nov 4, 2016 ▶ 3:53
Assertion Supported
CMG@Ventures launched first internet-only VC fund in 1995
“In January, 95, we launched a small 30, thirty-five million dollar fund, and it was the first Fun to focus exclusively on what was then segmented out as the internet”
Jerry Colonna Nov 4, 2016 ▶ 4:34
Disclosure
Jerry Colonna discloses his teenage suicide attempt and hospitalization
“I had been very open about the fact that I had been suicidal in my teenage years having been hospitalized at one point for an attempt.”
Jerry Colonna Nov 4, 2016 ▶ 6:11
Disclosure
Jerry Colonna stepped down from Flatiron Partners in 2001 due to depression
“I went to Fred and I said in the spring of 2001, I said, I can't continue. I can't do this.”
Jerry Colonna Nov 4, 2016 ▶ 6:31
Insight
Jerry Colonna: Sustained emotional compartmentalization leads to depression
“Living with a mask where the outer does not match the inner over a prolonged period of time, that leads to a notion of disassociation. And disassociative states can be, again, can be helpful, right? If I'm experiencing something I don't want to experience, it …”
Jerry Colonna Nov 4, 2016 ▶ 10:13
Opinion
Jerry Colonna: VCs mimic aggressive behavior to cover underlying insecurity
“I think that's the biggest problem in the venture business is that I think that many investors mimic the most aggressive behaviors that as a way to cover their fundamental insecurity.”
Jerry Colonna Nov 4, 2016 ▶ 13:51
Opinion
Colonna: Traditional unreflective VC behavior does not increase fund returns
“The current way of doing things isn't necessary. It Doesn't necessarily lead to better returns, which by the way is what the job is and is painful.”
Jerry Colonna Nov 4, 2016 ▶ 14:54
Insight
Jerry Colonna: VCs are complicit in creating negative founder dynamics
“I think that VCs would benefit from spending more time looking at their own behavior, looking at the ways in which they are complicit in creating the conditions they say they don't want.”
Jerry Colonna Nov 4, 2016 ▶ 16:45
Insight
Colonna: Emotional rapport is the essential criteria when choosing a mentor
“If you can establish that rapport with that person, then the intellectual piece is easy, but the key is to really have that emotional rapport with the person.”
Jerry Colonna Nov 4, 2016 ▶ 19:32
Insight
Colonna: Outside parties cannot prescribe an individual's work-life balance
“It's presumptuous of anyone to say the way you're balancing things is incorrect. What is correct is for you to keep tuning in to yourself, to those voices, to And saying to yourself, how's this feeling right now?”
Jerry Colonna Nov 4, 2016 ▶ 22:29
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