Podcast Summary:

Tech Brew Ride Home
Episode Title: (BNS) You're Not Killing It. Nobody Is Killing It. VC Legend Jerry Colonna
Date: September 27, 2025
Host: Adam (Morning Brew)
Guest: Jerry Colonna

Main Theme & Purpose

This episode is a candid conversation with legendary venture capitalist and executive coach Jerry Colonna. The core theme is the myth of “crushing it” in Silicon Valley—why building companies is hugely difficult, how impostor syndrome and depression are common, and why open discussion about struggle is both necessary and humanizing. Colonna walks through his journey: from a working-class Brooklyn childhood, to tech journalism, to founding Flatiron Partners (one of NYC’s first big VC funds), to personal crisis and ultimately coaching startup founders. The episode’s tone is raw, reflective, and inspiring, offering both an insider’s history of the early internet and a meditation on leadership, vulnerability, and resilience.

Key Discussion Points & Insights

1. Debunking the "Crushing It" Myth

• Colonna opens by challenging Silicon Valley’s pressure-cooker mythos.
  • "No one’s crushing it. There’s no such thing as crushing it. There are good days and there are bad days. And let’s stop with the myth making and let’s talk about the reality." — Jerry Colonna [00:32]
• Building anything meaningful is “fucking genius and fucking hard.”
  • "Just because you’re struggling doesn’t mean you’re bad at the job. It just means it’s hard." [00:32]

2. Growing Up in New York

• Childhood in Flatbush, Bensonhurst, then Queens; attended Edward R. Murrow High School—described as a haven for creative misfits. [01:31–03:14]
• Depiction of 1970s–80s NYC: the 1977 blackout, South Bronx fires, subway graffiti, and how old neighborhoods were diverse but challenging.
  • "I land in New York and I feel at home among the diversity, even though I’m whiter than white. And I feel like that diversity gives me hope. Fuck em. This is our country." [06:59]

3. September 11th & Community Resilience

• Recounts being deeply connected to NYC’s Arab-American communities post-9/11, resisting anti-Arab sentiment by organizing dinners in Brooklyn.
• Reflects on New York’s power being in its quilt of cultures and languages.
  • "In New York City with our 1 million plus students, there were 118 languages spoken in our schools, like, fuck you. That’s New York. There’s a power in that." [09:24]

4. Mental Health Struggles

• Attempts suicide after a period of depression in college; credits a scholarship and a supportive advisor for enabling his recovery and future success. [11:10–14:01]
• First semester at Queens College was “massive depression” leading to hospitalization. [13:10]

5. Becoming a Tech Journalist

• Early 1980s: Works at Information Week, covering mainframes and new tech (Big Iron, gallium arsenide chips, Cray supercomputers).
• Admits learning entire industries by autodidactic hustle and on-the-job curiosity as an English major.
  • "Everything is autodidact, everything is self taught. The number one drive…curiosity." [18:33]
• Anecdote: Filing stories via pay phones and a primitive “laptop” with a modem hack. [14:01–16:22]

6. Evolution of Tech Media

• Explains how 1980s–90s tech journalism was the sole route for big names like Bill Gates and Steve Jobs to reach the industry.
  • “Bill Gates would come to my office and sit there and take his shoes and socks off and rock back and forth…” [23:59]
• Describes being at the epicenter as paper-based magazines moved to the web, experimenting with interactive CD-ROMs, trade show dailies, and the first web ad models. [26:11–33:28]
• Grapples with emerging ethical issues: responsibility to correct errors instantly, shifting the culture of publishing. [33:23]

7. Jump to Venture Capital

• Invited into VC world without prior experience, driven by fascination with the internet’s disruptive potential, not by monetary ambition. [40:10–41:06]
  • “I had no idea that I actually might make money. I was just fascinated by what was happening with the way in which we interacted with information.” [41:06]
• Early investments: first web search engines (Lycos), buying 10% for “a couple hundred thousand dollars” and IPO’ing for $200M in months. [42:26–44:26]

8. Founding Flatiron Partners

• Meets Fred Wilson (future Union Square Ventures), co-founds NYC-based Flatiron with a scrappy, “Yankees cap and ripped jeans” ethos, versus the staid, status-driven world of Boston and Silicon Valley VC. [46:33–54:31]
• Early deals include YoYodyne with Seth Godin (permission marketing pioneer), and GeoCities (first homepages/social media).
  • "You get a free PC, but you have to look at ads all over the place." [48:05]
  • GeoCities: major cultural impact as the first place for ordinary people to share their stories online. Sold to Yahoo for $3–4B. [58:05–63:20]

9. The Dot-Com Crash and Personal Reckoning

• Describes the mental toll of the dot-com bubble burst ("From 1996…everything we touched turned to gold. By 2001, it felt like everything we touched turned to shit.") [65:59]
• Linked his worsening depression and dissatisfaction with the external markers of success to an inner mismatch.
  • "The more success I had externally, the shittier I felt." [67:15]

10. Becoming a Coach and Mission to “Alleviate Suffering”

• Leaves VC in 2002, turns to executive coaching as a way to support others facing the same pain and isolation he endured as a founder, investor, and leader. [67:47]
• Founded Reboot, now a renowned coach, podcaster, and author.
• Central message: “You’re not alone. Depression lies.” Suffering is common—especially among founders—but silence perpetuates it.
  • "Depression lies. And one of the lies it tells you is that because you feel like shit, you are shit. That is not true. And you’re not alone." [70:30]
  • "You’re not crushing it. No one’s crushing it. There are good days and there are bad days… Building a company is a magic act. You create something out of nothing and you get people to believe. That is fucking genius and fucking hard. Both are true. And just because you’re struggling doesn’t mean you’re bad at the job. It just means it’s hard." [71:13]

Notable Quotes & Memorable Moments

• On start-up delusions:
  "The bullshit and the spinning stops here. You're not crushing it. No one's crushing it. There are good days and there are bad days." — Jerry Colonna [70:30]
• On diversity as America’s strength:
  "In New York City with our 1 million plus students, there were 118 languages spoken in our schools, like, fuck you. That’s New York. There’s a power in that." [09:24]
• On mental health:
  "Depression lies. And one of the lies it tells you is that because you feel like shit, you are shit. That is not true. And you’re not alone." [70:30]
• On personal mission:
  "All I’m really doing is going back in time to 38 year old Jerry, saving his life again and again and again...I’m in coaching for one purpose only, to alleviate suffering." [68:32]
• On the value of curiosity:
  "The thing that made me a journalist, the thing that made me a really good investor, the thing that makes me a really good coach is curiosity. Curiosity." [18:59]
• On the reality of building:
  "Building a company is a magic act. You create something out of nothing and you get people to believe. That is fucking genius and fucking hard. Both are true. And just because you’re struggling doesn't mean you're bad at the job. It just means it's hard." [71:13]

Timestamps for Key Segments

• [00:32] – The myth of “crushing it”; emotional realities of founders
• [01:23–04:15] – Growing up in Brooklyn and Queens; 70s New York nostalgia
• [06:59–10:04] – After 9/11: New York, Arab-American community, resilience
• [11:10–14:01] – College depression, suicidal ideation, rescued by mentorship
• [14:01–20:26] – Breaking into tech journalism; curiosity as superpower
• [23:00–26:09] – The power, responsibility, and culture of 80s/90s tech media
• [26:11–35:29] – The dawn of the web: inventing ad models and business models
• [40:10–44:26] – Leap to VC; Lycos investment; invention of search and monetization
• [46:33–54:31] – Founding Flatiron; NYC VC culture vs. Silicon Valley/Boston
• [55:14–57:48] – YoYodyne (Seth Godin), invention of permission marketing
• [58:05–63:20] – GeoCities: roots of social media, hosting the world’s first homepages
• [65:08–68:32] – Dot-com crash, depression, transition to coaching
• [70:26–71:13] – Advice to struggling founders: “You’re not alone. Depression lies."

Episode Tone & Takeaways

The conversation is frank, witty, sometimes profane, and deeply humane. Colonna de-romanticizes entrepreneurship and investment — success comes with invisibly high emotional costs, and every “legend” is fighting a private battle. The show isn’t just a tech time capsule; it's a manifesto for honesty in leadership, a call to coaches and founders alike to drop the pretense and care for the human heart.

If you're a founder (or simply alive), Colonna’s central wisdom is this:
Struggle is universal and invisible. Curiosity, connection, and candor matter more than resumes. Resilience isn’t about never falling down, it's about getting back up — and being willing to ask for help.

Recommended Follow-up:
Explore Jerry Colonna’s Reboot podcast, and his books for more on founder mental health and authentic leadership practices.