Tech Brew Ride Home (BNS) You're Not Killing It. Nobody Is Killing It. VC Legend Jerry Colonna
46 snips
Sep 27, 2025 
In this engaging discussion, Jerry Colonna, a veteran investor and executive coach, reflects on his journey from journalism to venture capital. He challenges the myth of 'crushing it' in entrepreneurship, emphasizing the emotional struggles founders face. Jerry shares insights on the importance of curiosity, recounts his Brooklyn upbringing, and discusses the impact of 9/11 on his career. He highlights his mission with Reboot to alleviate suffering in leadership and offers mental health advice for entrepreneurs, reminding them that struggle doesn’t equal failure.
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The Myth Of 'Crushing It'
- Building a company is both genius and incredibly hard at the same time.
- Struggling doesn't mean you're bad at the job, it means the work is difficult.
Scholarship That Changed His Path
- Jerry describes arriving at Queens College after skipping college applications and then attempting suicide in his first year.
- A professor saved him with a scholarship and summer job that led to his journalism career.
Ask The Second Question
- Ask the second question and follow unexpected answers instead of reading a checklist.
- Hold your agenda lightly and let the conversation reveal unanticipated gold.
