(BNS) You're Not Killing It. Nobody Is Killing It. VC Legend Jerry Colonna
One of the very first VCs of the Internet Era, and especially the NYC tech ecosystem, Jerry Colonna reflects on his journey from growing up in New York to becoming a successful journalist and venture capitalist. Jerry discusses his transition to venture capital, the founding of Flatiron with Fred Wilson, and the challenges faced during the dot-com bubble and 9/11. He emphasizes the importance of curiosity and the human experience in his coaching practice, aiming to alleviate suffering and transform lives.
Learn more about your ad choices. Visit megaphone.fm/adchoices
How have I been complicit in creating the conditions I say I don’t want? | Jerry Colonna (CEO of Reboot, executive coach, former VC)
Jerry Colonna is a world-renowned executive coach, a former venture capitalist, and the co-founder and CEO of Reboot, an executive coaching firm that combines practical leadership development with deeper self-inquiry. With over 27 years of coaching experience, he has guided countless leaders through the challenges of scaling companies, building teams, and navigating the emotional complexities of leadership. Known for his radical-self-inquiry approach, Jerry helps leaders uncover the unconscious patterns that hold them back and empowers them to lead with authenticity, compassion, and clarity.
In our conversation, we cover:
1. A powerful question that unlocks self-awareness: “How have I been complicit in creating the conditions I say I don’t want?”
2. Jerry’s foundational equation for leadership success: practical skills + radical self-inquiry + shared experiences = enhanced leadership and resilience
3. Why teams most often fail (hint: it’s not lack of talent or strategy)
4. How busyness often masks deeper issues of self-worth
5. Why a “growth mindset” can be problematic
6. The importance of legacy and what it means to live a meaningful life
7. The role of AI in self-inquiry and how tools like ChatGPT can help uncover blind spots
8. Jerry’s advice for navigating the unsettling rise of AI and its implications for leadership and humanity
—
Brought to you by:
Eppo—Run reliable, impactful experiments
Contentsquare—Create better digital experiences
OneSchema—Import CSV data 10x faster
—
Where to find Jerry Colonna:
• X: https://x.com/jerrycolonna
• LinkedIn: https://www.linkedin.com/in/jerry-colonna-reboot/
• Website: https://reunion.reboot.io/
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
In this episode, we cover:
(00:00) Introduction to Jerry Colonna
(04:12) Jerry’s key question
(06:55) The equation for great leadership
(09:37) The big lie of success and happiness
(12:12) The consciousness hack
(15:56) Getting over the fear of consequences
(20:23) The problem with bypassing our childhood baggage
(23:22) Radical self-inquiry: asking the tough questions
(27:05) Shared experiences: the power of community
(30:25) The trap of busyness and attachment
(40:45) Understanding our own intentions
(46:58) Legacy and purpose
(55:43) Writing for self-discovery
(57:12) The impact of AI on humanity
(01:05:00) Turning a growth mindset into a fixed mindset
(01:11:30) The role of radical self-inquiry in leadership
(01:19:24) Final thoughts and reflections
—
Referenced:
• Naropa University: https://www.naropa.edu/
• Fitler Club: https://fitlerclub.com
• Chris Fralic on LinkedIn: https://www.linkedin.com/in/chrisfralic/
• Will Smith on the price of fame: ‘I have been deeply humbled and deeply inspired’: https://www.today.com/popculture/news/will-smith-fame-rcna127830
• Seth Godin’s best tactics for building remarkable products, strategies, brands, and more: https://www.lennysnewsletter.com/p/seth-godins-tactics-for-building-remarkable-products
• The life of Buddha: https://www.britannica.com/summary/Buddha-founder-of-Buddhism
• 10% Happier with Dan Harris podcast: https://podcasts.apple.com/us/podcast/10-happier-with-dan-harris/id1087147821
• Simon Sinek’s website: https://simonsinek.com/
• Mike Tyson Gives Morbid Response to Young Interviewer’s Question About His “Legacy”: https://www.vibe.com/news/entertainment/mike-tyson-morbid-response-young-interviewer-legacy-1234944054/
• Dan Shipper’s post on X about asking ChatGPT for blind spots: https://x.com/danshipper/status/1910387987487318318
• Evernote: https://evernote.com/
• Claude: https://claude.ai
• Peter Senge on X: https://x.com/petersenge
• Carl Jung’s quote: https://www.goodreads.com/quotes/44379-until-you-make-the-unconscious-conscious-it-will-direct-your
• Parker Palmer on LinkedIn: https://www.linkedin.com/in/parker-j-palmer-5a92b110/
• The unexamined life is not worth living: https://en.wikipedia.org/wiki/The_unexamined_life_is_not_worth_living
—
Recommended books:
• Reboot: Leadership and the Art of Growing Up: https://www.amazon.com/Reboot-Leadership-Art-Growing-Up/dp/0062749536
• Reunion: Leadership and the Longing to Belong: https://www.amazon.com/Reunion-Leadership-Longing-Jerry-Colonna/dp/0063142139
• Born to Run: https://www.amazon.com/Born-Run-Bruce-Springsteen/dp/1501141511
• 10% Happier: How I Tamed the Voice in My Head, Reduced Stress Without Losing My Edge, and Found Self-Help That Actually Works—A True Story: https://www.amazon.com/10-Happier-Self-Help-Actually-Works/dp/0062265431
• Soldiers and Kings: Survival and Hope in the World of Human Smuggling: https://www.amazon.com/Soldiers-Kings-Survival-World-Smuggling/dp/0593298586
• The Giving Tree: https://www.amazon.com/Giving-Tree-Shel-Silverstein/dp/0060256656/
—
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.
—
Lenny may be an investor in the companies discussed.
This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
Jerry Colonna on 'Reunion': sustaining founder drive, enlightened leadership, and more! | E1864
This Week in Startups is brought to you by…
Corient. Real wealth requires real solutions. Corient provides wealth management services centered around you. For more information, speak with an advisor today at Corient.com
Lemon.io - Hire pre-vetted remote developers, get 15% off your first 4 weeks of developer time at https://Lemon.io/twist
Coda. A new doc that brings words, tables and teams together. All your valuable data, plans, objectives, and strategies in one place. Go to https://coda.io/twist to get a $1,000 credit!
*
Today’s show:
Jerry Colonna joins Jason in person for a philosophical dialogue about the search for meaning as an entrepreneur, drawing on their multi-decade friendship. They explore Jerry's personal journey from venture capitalist to founder coach (11:08), the challenges leaders face as startups evolve (40:03), how Jerry helps entrepreneurs transition from founder to CEO (28:54), and much more!
Timestamps:
(0:00) Jerry Colonna joins Jason
(1:14) Jason's early internet days and first taste of money/power
(10:08) Corient - Speak with one of Corient's wealth management advisors today at http://corient.com
(11:08) Jerry's journey as a venture capitalist during the peak Dot-com era to founder coach
(18:32) What pushed Jerry to his limits, and how did Jerry overcome his depression
(23:36) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist
(24:56) Jerry's Book "Reboot" and what Jerry sees drives founders
(28:54) How to transition from a founder to a CEO
(38:31) Coda - Get started for free at https://coda.io/twist
(40:03) Finding the right motivation and the steps to being an enlightened leader
(57:01) Acute issues that founders contact Jerry about
*
Check out Reboot: https://www.reboot.io/reboot-leadership-and-the-art-of-growing-up/
Check out reunion: https://www.reboot.io/reunion-leadership-and-the-longing-to-belong/
*
Follow Jerry
X: https://twitter.com/jerrycolonna
LinkedIn: https://www.linkedin.com/in/jerry-colonna-reboot
*
Follow Jason:
X: https://twitter.com/jason
Instagram: https://www.instagram.com/jason
LinkedIn: https://www.linkedin.com/in/jasoncalacanis
*
Great 2023 interviews: Steve Huffman, Brian Chesky, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland
*
Check out Jason’s suite of newsletters: https://substack.com/@calacanis
*
Follow TWiST:
Substack: https://twistartups.substack.com
Twitter: https://twitter.com/TWiStartups
YouTube: https://www.youtube.com/thisweekin
*
Subscribe to the Founder University Podcast: https://www.founder.university/podcast
#554: Jerry Colonna — How to Reboot Yourself and Feel Unrushed in the New Year
Jerry Colonna — How to Reboot Yourself and Feel Unrushed in the New Year| Brought to you by Wealthfront automated investing, Headspace easy-to-use app with guided meditations, and Eight Sleep’s Pod Pro Cover sleeping solution for dynamic cooling and heating. More on all three below.
“What benefit do I get from the conditions I say I don’t want?” — Jerry Colonna
Jerry Colonna (@jerrycolonna) is the CEO and co-founder of Reboot.io, an executive coaching and leadership development firm dedicated to the notion that better humans make better leaders. For nearly 20 years, he has used the knowledge gained as an investor, an executive, and a board member for more than 100 organizations to help entrepreneurs and others lead with humanity, resilience, and equanimity.
Prior to his career as a coach, he was a partner with JPMorgan Partners (JPMP), the private equity arm of JPMorgan Chase. Previously, he led New York City-based Flatiron Partners, which he founded in 1996 with partner Fred Wilson. Flatiron became one of the nation’s most successful early-stage investment programs. Jerry’s first leadership position, at age 25, was editor-in-chief of InformationWeek magazine. He is the author of Reboot: Leadership and the Art of Growing Up.
Jerry lives in Boulder, Colorado. This is his second appearance on the podcast. His first can be found at tim.blog/jerrycolonna.
Please enjoy!
This episode is brought to you by Eight Sleep! Eight Sleep’s Pod Pro Cover is the easiest and fastest way to sleep at the perfect temperature. It pairs dynamic cooling and heating with biometric tracking to offer the most advanced (and user-friendly) solution on the market. Simply add the Pod Pro Cover to your current mattress and start sleeping as cool as 55°F or as hot as 110°F. It also splits your bed in half, so your partner can choose a totally different temperature.
And now, my dear listeners—that’s you—can get $250 off the Pod Pro Cover. Simply go to EightSleep.com/Tim or use code TIM at checkout.
This episode is also brought to you by Headspace! Headspace is your daily dose of mindfulness in the form of guided meditations in an easy-to-use app. Whatever the situation, Headspace can help you feel better. Overwhelmed? Headspace has a 3-minute SOS meditation for you. Need some help falling asleep? Headspace has wind-down sessions their members swear by. And for parents, Headspace even has morning meditations you can do with your kids. Headspace’s approach to mindfulness can reduce stress, improve sleep, boost focus, and increase your overall sense of well-being.
Go to Headspace.com/Tim for a FREE one-month trial with access to Headspace’s full library of meditations for every situation.
This episode is also brought to you by Wealthfront! Wealthfront pioneered the automated investing movement, sometimes referred to as ‘robo-advising,’ and they currently oversee $20 billion of assets for their clients. It takes about three minutes to sign up, and then Wealthfront will build you a globally diversified portfolio of ETFs based on your risk appetite and manage it for you at an incredibly low cost.
Smart investing should not feel like a rollercoaster ride. Let the professionals do the work for you. Go to Wealthfront.com/Tim and open a Wealthfront account today, and you’ll get your first $5,000 managed for free, for life. Wealthfront will automate your investments for the long term. Get started today at Wealthfront.com/Tim.
For show notes and past guests, please visit tim.blog/podcast.
Sign up for Tim’s email newsletter (“5-Bullet Friday”) at tim.blog/friday.
For transcripts of episodes, go to tim.blog/transcripts.
Discover Tim’s books: tim.blog/books.
Follow Tim:
Twitter: twitter.com/tferriss
Instagram: instagram.com/timferriss
Facebook: facebook.com/timferriss
YouTube: youtube.com/timferriss
Past guests on The Tim Ferriss Show include Jerry Seinfeld, Hugh Jackman, Dr. Jane Goodall, LeBron James, Kevin Hart, Doris Kearns Goodwin, Jamie Foxx, Matthew McConaughey, Esther Perel, Elizabeth Gilbert, Terry Crews, Sia, Yuval Noah Harari, Malcolm Gladwell, Madeleine Albright, Cheryl Strayed, Jim Collins, Mary Karr, Maria Popova, Sam Harris, Michael Phelps, Bob Iger, Edward Norton, Arnold Schwarzenegger, Neil Strauss, Ken Burns, Maria Sharapova, Marc Andreessen, Neil Gaiman, Neil de Grasse Tyson, Jocko Willink, Daniel Ek, Kelly Slater, Dr. Peter Attia, Seth Godin, Howard Marks, Dr. Brené Brown, Eric Schmidt, Michael Lewis, Joe Gebbia, Michael Pollan, Dr. Jordan Peterson, Vince Vaughn, Brian Koppelman, Ramit Sethi, Dax Shepard, Tony Robbins, Jim Dethmer, Dan Harris, Ray Dalio, Naval Ravikant, Vitalik Buterin, Elizabeth Lesser, Amanda Palmer, Katie Haun, Sir Richard Branson, Chuck Palahniuk, Arianna Huffington, Reid Hoffman, Bill Burr, Whitney Cummings, Rick Rubin, Dr. Vivek Murthy, Darren Aronofsky, and many more.
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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 is a Co-Founder and Managing Director @ Foundry Group, one of the most successful venture firms of the last decade with a portfolio including the likes of Zynga, Fitbit and Sendgrid to name a few. Brad is also a co-founder @ Techstars and prior to Foundry, he co-founded Mobius Venture Capital.
Tracy Lawrence spent the last 8 years as Founder & CEO @ Chewse, the startup that it effortless for office managers to order delicious food for their teams. Tracy grew the team to 300 people across 4 markets, raised millions in venture capital, and ultimately sold the business to Foodee.
Jerry Colonna is the CEO of Reboot.io where he is now the professional coach to some of the world's leading founders. Prior to his work with Reboot, Jerry was an early-stage VC co-founding Flatiron alongside Fred Wilson in 1996.
In Today's Episode You Will Learn:
1.) How did Brad, Jerry and Tracy all experience their first forms of depression? At what stage did it become a more prominent part of their life? Why do they think then was the catalyst?
2.) Why does Jerry believe that despite what people say, no one is crushing it? How can founders present their vulnerability as a strength? At what point did Tracy realise this? How did she convey her vulnerability to her team? Who is to blame for the lack of vulnerability and fear of opening up?
3.) How does Brad think about tying happiness to milestones? What are the biggest dangers of doing so? Does this mean one does not have goals? How does one balance between ambition and appreciating the present? How did Brad learn this when Amy asked for a divorce? How did he respond?
4.) Why does Brad believe fear, guilt and anxiety are useless emotions? What was the result of Tracy tying her mental state to her revenue line? How does Tracy think about the loneliness of being a founder? What does Brad believe is some of the biggest BS in the industry?
As always you can follow Harry and The Twenty Minute VC on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
#373: Jerry Colonna — The Coach With the Spider Tattoo
"You are not alone. And just because you feel like shit doesn't mean you are shit." — Jerry Colonna
Jerry Colonna (@jerrycolonna) is the CEO and cofounder of Reboot.io, an executive coaching and leadership development firm dedicated to the notion that better humans make better leaders.
Prior to his career as a coach, he was a partner with J.P. Morgan Partners (JPMP), the private equity arm of J.P. Morgan Chase. Prior to that, he cofounded New York City-based Flatiron Partners with Fred Wilson, which became one of the nation's most successful early-stage investment programs. His first leadership position, at age 25, was Editor-In-Chief of InformationWeek magazine, and now he has returned to the written word with his first book, Reboot: Leadership and the Art of Growing Up.
Click here for the show notes for this episode.
***
If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts/iTunes? It takes less than 60 seconds, and it really makes a difference in helping to convince hard-to-get guests. I also love reading the reviews!
For show notes and past guests, please visit tim.blog/podcast.
Sign up for Tim’s email newsletter (“5-Bullet Friday”) at tim.blog/friday.
For transcripts of episodes, go to tim.blog/transcripts.
Discover Tim’s books: tim.blog/books.
Follow Tim:
Twitter: twitter.com/tferriss
Instagram: instagram.com/timferriss
Facebook: facebook.com/timferriss
YouTube: youtube.com/timferriss
Past guests on The Tim Ferriss Show include Jerry Seinfeld, Hugh Jackman, Dr. Jane Goodall, LeBron James, Kevin Hart, Doris Kearns Goodwin, Jamie Foxx, Matthew McConaughey, Esther Perel, Elizabeth Gilbert, Terry Crews, Sia, Yuval Noah Harari, Malcolm Gladwell, Madeleine Albright, Cheryl Strayed, Jim Collins, Mary Karr, Maria Popova, Sam Harris, Michael Phelps, Bob Iger, Edward Norton, Arnold Schwarzenegger, Neil Strauss, Ken Burns, Maria Sharapova, Marc Andreessen, Neil Gaiman, Neil de Grasse Tyson, Jocko Willink, Daniel Ek, Kelly Slater, Dr. Peter Attia, Seth Godin, Howard Marks, Dr. Brené Brown, Eric Schmidt, Michael Lewis, Joe Gebbia, Michael Pollan, Dr. Jordan Peterson, Vince Vaughn, Brian Koppelman, Ramit Sethi, Dax Shepard, Tony Robbins, Jim Dethmer, Dan Harris, Ray Dalio, Naval Ravikant, Vitalik Buterin, Elizabeth Lesser, Amanda Palmer, Katie Haun, Sir Richard Branson, Chuck Palahniuk, Arianna Huffington, Reid Hoffman, Bill Burr, Whitney Cummings, Rick Rubin, Dr. Vivek Murthy, Darren Aronofsky, and many more.
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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 is a Founder @ Reboot, the coaching company that helps some of the world's greatest entrepreneurs and investors with the internal ups and downs in their life and support the growth they need to improve their performance. Prior to Reboot, Jerry was a Partner @ JP Morgan. Before that Jerry was a VC, having launched Flatiron partners in 1996 with his partner, Fred Wilson. Flatiron became on the of the most successful early stage investment firms in New York with investments in the likes of Geocities, Gamesville and The New York Times Digital. In Today's Episode You Will Learn: 1.) How did Jerry enter the world of VC and then make the transition to be the ultimate CEO/VC coach, aka, 'The CEO Whisperer'?
2.) What is Jerry's first step for anyone looking to self-evaluate in what Jerry calls, 'radical self-inquiry'?
3.) Once self-evaluated, how can one look to be their true self in a world that is not necessarily accepting of such vulnerability, compassion and emotion, for example, VC and startups?
4.) How does Jerry evaluate the current crop of VCs in terms of them being their inner self to the external world? Why is Jerry so optimistic?
5.) Questions from Brad Feld: 1.) What should VCs be spending more time on? 2.) If Jerry could give one piece of advice to VCs what would it be?
Items Mentioned In Today's Episode:
Jerry's Fave Blog: Fred Wilson: AVC, Brad Feld: Feld Thoughts, The School of Life
Jerry's Fave Book: When Things Fall Apart
As always you can follow The Twenty Minute VC, Harry and Jerry on Twitter here!
Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.
The Twenty Minute VC is proudly sponsored by Luma, Luma is the world's first ever Surround WiFi system that brings speed, security and control to the home network. And Unlike traditional routers, Luma comes in a pack of two or three sleek devices to place in different rooms in your home. Luma then creates a mesh network that work together to create an outrageously-fast, ultra-secure Surround WiFi network. Lastly, Luma's app lets you easily see and control which devices, users and content are on your network. To buy your Luma, simply dead to getluma.com or amazon.com.
