Jerry Colonna
Co-Founder and CEO, Reboot.io. On 3 shows, 4 appearances. The Shows tab opens the full record on each.
founderexecutiveinvestorauthorhost@jerrycolonna ↗LinkedIn ↗reboot.io ↗Wikipedia ↗
Before becoming an executive coach, he was an early dot-com venture capitalist who co-founded Flatiron Partners and served as a partner at JPMorgan Partners. He co-founded Reboot.io to work with startup founders and executives, and authored the book Reboot: Leadership and the Art of Growing Up.
3shows
4appearances
45statements
2resolved
2supported
0contradicted
100%fully supported
38said about them ↓ Everything Jerry Colonna said on any show that made the record, most notable first. Each card names its show and opens the statement there.
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.”
Colonna: Founders sabotage successful businesses to avoid unresolved childhood baggage
“If you continue to bypass sorting out your baggage, there's going to come a day where you're going to have to pay that price. It could be in your own depression. It could be in, I've seen this a thousand times, Lenny, entrepreneurs sabotaging their successful …”
Colonna: Unreflective leaders curse their teams to manifest early life dysfunctions
“So if you want to create a high functioning team, do your work. And it starts with the person who has the most power in the group. If that person refuses to do their work, the entire group will become, ah, a manifestation of early dysfunction in the individual…”
Colonna: Escaping founder mode requires tolerating boneheaded decisions by your team
“You want to build a scaled leadership team. You have to be willing to have them make boneheaded decisions. And that's really, really hard, especially if we're quote in founder mode, driving all the decisions.”
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: Believing perpetual happiness is achievable worsens mental health
“It's that somehow that there's this achievable state where everyone feels great and happy all the time, and that is the biggest myth, and it actually exacerbates our search for mental well-being.”
Colonna: Teams without self-inquiry repeat dysfunctions from their families of origin
“Without the individual radical self-inquiry skills. Groups tend to be condemned to repeating patterns, oftentimes of their family of origin.”
Colonna: Generational trauma and immigrant backgrounds drive achievement through constant catastrophizing
“I notice this a lot with the descendants of immigrants, or the descendants of those who might have survived pogroms, or the descendants of those who might have experienced famine, there's a particular attachment To holding on to the possibility of negative out…”
Colonna agrees with Lux Capital's Josh Wolfe: chips on shoulders drive success
“Josh Wolf, who is a VC at Lux Capital, likes to say, chips on shoulders, put chips in pockets. And he is right when he speaks about that.”
Colonna: Breakthrough innovation happens when relaxed, not driven by inadequacy
“In my experience, those real innovative moments actually occur when the brain is relaxed, when the heart is relaxed, ok? When we are not terrified that we are not enough.”
Colonna: Toxic workplaces stem from empowering people who cannot use words
“We wonder why we have toxic workplaces. Well, because we give power to people who don't know how to use their words.”
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…”
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.”
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.”
Colonna: Being complicit is driving the getaway car, not robbing the bank
“So I purposely chose the word complicit, because complicit does not mean responsible. And that's a really important distinction. And as I often say, to understand the word complicit, think of the word accomplice. Right. As I will share, you are driving the get…”
Colonna: Great leadership requires practical skills, self-inquiry, and shared experiences
“And so the equation is practical skills plus radical self-inquiry plus shared experiences. That is the process of actually talking about the craziness that goes on in your head equals greater leadership. Okay. That all makes sense. But then there was this othe…”
Colonna: You don't have to be an asshole to be successful
“And I could not think of a better summation of everything that I'm about than for a 19 year old kid to look up and say, you don't have to be an asshole to be successful. And of course the corollary to that is you don't have to feel miserable just because you'r…”
Colonna: The best self-inquiry questions provoke fear and startle you
“Questions that startle us, questions that may cause us to be a little afraid of the answer. That's where the gold is.”
Colonna: The startup ecosystem socializes founders to constantly bullshit about success
“We too often than not, especially in what I would say the entrepreneurial community. We're socialized to bullshit, not only ourselves, but everybody else, right? All our companies are moving up into the right. Every product is working. We don't really have any…”
Colonna: Celebrating grades on the fridge signals conditional love to children
“When we take that test, that spelling test, and we stick it with magnets on the refrigerator, it's out of pride. The challenging message that we inadvertently can send to our children Is that we only love them because they got an A on the spelling test. And so…”
Colonna: Leadership development is continuous inquiry, not just continuous improvement
“The art of growing up is a practice. It's not a scientific, ah, moment where one day you wake up and you're done. It's an ongoing practice of not continuous improvement, but continuous inquiry. That can feel exhausting when you contemplate it, but enlivening w…”
Colonna: Dogmatically enforcing a growth mindset turns it into a fixed mindset
“When we get too fixed on the proper way to do things, we're setting ourselves up for attachment and therefore suffering. So if you can hold something like a mindset, Loosely with that attachment, go for it. Have a blast. Enjoy it. But the minute you start to n…”
Colonna: Prolonged Disconnect Between Inner and Outer Persona Causes Depression
“And that led to this disconnect between the inner me and the outer me, which on a prolonged period of time leads to depression.”
Colonna: Shape-Shifting for Anxious Parents Creates Generational Behavioral Patterns
“If we grow up in an environment where, where in order to say, make our depressed father Less depressed, or our anxious mother less anxious by shape-shifting. The likelihood is that we will pass that pattern on to our descendants.”
The other half of the tape: Jerry Colonna's own voice is left out of every number here. Other people bring the name up 37 times in 12 episodes across the shows. 1 statement on the record names them. every mention, with the transcript →
Who brings them up most Moisey Uretsky 9Brad Feld 7Harry Stebbings 5Semil Shah 4Lenny Rachitsky 4John Fein 3Jeff Fagnan 3Tristan Handy 1
Statements about Jerry Colonna, by other people (1)
Every mention by year
tap a year for its mentions
20VC 32
Lenny's Podcast 4
the Knowledge Project 1
2025 4 mentions in 3 episodes 1 per episode
- 35 years of product design wisdom from Apple, Disney, Pinterest and beyond | Bob Baxley
- A guide to difficult conversations, building high-trust teams, and designing a life you love
- Inside Devin: The AI engineer that's set to write 50% of its company’s code this year | Scott Wu
- every mention in 2025, scene by scene →
2022 1 mention in 1 episode
2021 1 mention in 1 episode
2020 1 mention in 1 episode
2019 18 mentions in 4 episodes 5 per episode
- 20VC: Brad Feld on Why Market Size At Early Stage Is Not Helpful, His Biggest Learnings From The Boom & Bust of The Dot Com and How The Best VCs Work For Their CEOs
- 20VC: Haystack's Semil Shah on Whether Founders Are Bypassing Seed Funds in Favour Of Less Dilutive Multi-Stage Funds, How Fund Strategy Changes With Fund Scaling & Why The Hardest Challenge is Price Discipline
- 20VC: Buffer's Joel Gascoigne on The Moment The Founder Is No Longer The Boss, The Questions Founders Must Ask Their VCs and Why We Need A Spectrum of Different Financing Mechanisms Other Than VC
- 20VC: The Ultimate Episode For Emerging Managers: How To Determine How Big A Fund To Raise, What Is The Right Closing Strategy With LPs & Why We Will Not See The Eradication of Pre-Seed with John Fein, Founder & Managing Partner @ Firebrand Ventures
- every mention in 2019, scene by scene →
2018 3 mentions in 1 episode
One line per show, most statements first. The link opens Jerry's full record on that show: the calibration, argument clarity, speaking style and every statement made there.
| Show | Role there | Eps | Statements | Record | |
|---|---|---|---|---|---|
| 20VCLEDGER | Co-Founder and CEO, Reboot.io | 2 | 17 | 100% 2/2 | full record on 20VC → |
| KNOWLEDGE PROJECTLEDGER | Co-Founder and CEO, Reboot.io | 1 | 15 | — | full record on the Knowledge Project → |
| LENNY'S PODCASTLEDGER | Co-Founder and CEO, Reboot.io | 1 | 13 | — | full record on Lenny's Podcast → |