Reboot: Leadership and the Art of Growing Up

Jerry Colonna‘s book, Reboot, came out this week.

He had given me the manuscript to read so many months ago that I had to go back and read it again before I could write about it.

So I bought the book yesterday and read it again over the last twenty four hours.

AVC regulars don’t need any introduction to Jerry. I’ve been writing about him, citing him, and telling stories about him since the very start of this blog.

Jerry is my friend, my former partner and co-founder of the first business I ever started, Flatiron Partners, and one of the best people on planet earth.

Jerry’s book is about two things that are really the same thing, himself and his work to help people, mostly entrepreneurs, discover themselves.

Jerry describes this work as “radical self inquiry”:

But the most challenging piece of the formula—indeed, the most important—is the notion of radically inquiring within. I define it as the process by which self-deception becomes so skillfully and compassionately exposed that no mask can hide us anymore. The notion is to recognize that, if things are not okay, if you’re struggling, you stop pretending and allow yourself to get help. Even more, it’s the process by which you work hard to know yourself—your strengths, your struggles, your true intentions, your true motivations, the characteristics of the character known as “you.” The you behind the masks, the stories, the protective but no longer useful belief systems that have been presented for so long as the “you” that you would like everyone to see.

Invariably such inquiry involves getting to know, as the poet Adrienne Rich says, “not the story of the wreck but the wreck itself.” With help, patience, courage, and guidance, we explore the wreck and retrieve the treasure. Knowing how to survive and understanding what it takes to thrive are skills that come from our childhood. Take any random group of entrepreneurs, for example, and do a quick unscientific survey by asking them to raise their hands if they grew up in an environment where at least one parent had disappeared or left or was never present. Most hands will shoot up. Early promotion into adulthood is often painful and equally often a sign of an early promotion into leadership. Probe a bit further and you may find that leaders who have built their company may have unconsciously stacked the team with other folks who experienced such early promotion.

Radically inquiring within allows us to step back and see the patterns of our lives not as random acts of a willful or even vengeful God but as forces that shape who we are. It’s this understanding that will make us not only better leaders but better, happier, more resilient people.

Reboot, the book, is about Jerry’s radical self inquiry to discover who he is and then his work to help others do the same.

He tells his own personal story over the course of the book and also weaves in the stories of others who he has worked with along the way to explain what the work of radical self inquiry is and why it must be done and the rewards that come from doing it. He is teaching by example.

Jerry started his career as a writer and he is a wonderful one. It is a joy to see him go back to those roots and exercise those muscles again.

Let me put it to you this way. You are reading AVC for a reason. Maybe you are an entrepreneur. Maybe you want to be one. Maybe you work for one. Maybe you are investing in entrepreneurs. Or maybe you are married to one. Or maybe your daughter is one. No matter what the reason, you are here at least in part because you are interested in entrepreneurs and the work they do. And so as part of that interest, I would recommend you pick up Jerry’s book and get inside the head of one. It will flip some switches on for you.

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Comments (Archived):

  1. jason wright

    à l’aise dans votre peau.

    1. fredwilson

      exactement

  2. LIAD

    Too funny. What a coincidence.Was listening to him giving a podcast interview on the book as the avc post notification came through.https://uploads.disquscdn.c

    1. Matt A. Myers

      108 – to infinity and beyond!

  3. awaldstein

    Haven’t read but did a listen to him on Tim Ferris’s podcast.So brutally honest–elevating and gratingly painful at times.He leads with his honesty and self. Wonderful, unabashed narrative.

    1. bsoist

      I listened to that on the way home from the Mets game on Sunday. Great stuff!

  4. William Mougayar

    The world needs more Jerrys. He is a gifted person, and he does get into your head in a positive way. I’ve been waiting for his book to come out. It will be my week-end read.I think I met Jerry 7-8 years ago in his office near USV’s. I asked him back then, why don’t you write a book? I remember back then he wasn’t too keen on it, but I’m glad he finally did. He does have a message.

  5. Charlie Crystle

    Definitely get it for the leaders in your life.Jerry was my coach for several years right around when he first started, I think, and still is in some ways; I hear his voice sometimes when I’m working through something difficult. And so when he released the book on Audible I was thrilled to learn he’s also the narrator. He’s so insightful… he helps you discover your own wisdom, in a sense. Good to hear his voice again.

  6. Matt Zagaja

    When I’m having a tough time I always find myself going back to a post on Brad Feld’s blog: https://feld.com/archives/2… With a nod to a story Jerry shared here on AVC. I will definitely pick up the book.

  7. Matt A. Myers

    Radically inquiry within: I’m curious if Jerry actually dives into the practices that lead to this – and hopefully more than generally stating yoga, meditation? The ego mind is very powerful and constantly active in most people due to unhealed childhood trauma they never healed, starting the path of indoctrination intertwined with coping mechanisms that add to a skew of bias, perfectionism that flattens developing nuanced and more holistic understanding, and most often a disconnect from emotion, empathy, compassion. There are silent meditation retreats as one option to start to crack open the ego, however not being lead there properly – or too rigid of an environment during – or not adequate support following can be a dangerous path as a person could be left in a circumstance where they lost the ego mind coping mechanism that has been allowing them to survive – only to be in the trauma, perhaps not even being connected to understanding what the trauma is, and without the coping mechanism (unhealthy as it may be) to help them cope. Similarly psychedelics/psychotropics like psilocybin mushrooms (the magic variety), DMT/5-MeO-DMT, Ayahuasca, Iboga, Kambo, LSD, MDMA, marijuana – all have different abilities, strengths, and potential of breaking through ego mind layers – where some of them you’re able to take and learn more from the experience than others; and unfortunately they are rapidly becoming mainstream without adequate knowledge or support before, during, and after – and they are extremely easy to get access to. The problem is simply cracking open the ego mind – ego death, ego dissolution – doesn’t necessarily heal any underlying trauma. They do seem to have the benefit of reducing rigidity in thinking, such rigidity will add to the baseline stress of the body and mind – as there’s a biofeedback loop, stressful thinking stresses the body, a stressed body causes stressful thinking – and so people generally feel a level of relief afterward, however there are pros and cons. A con to be aware of that is contrary to the commonly perpetuated belief that these psychedelics/psychotropics aren’t addictive: they do have the ability to break addiction to physical dependency – though a reminder for awareness sake that they are coping mechanisms for a reason – whether that is to sex, food, alcohol, tobacco, heroine, and so on, however they are in fact addictive to the ego mind. You can go to an Ayahuasca ceremony and drink the brew, drink 5+ cups of it, and have no reaction – there is underlying work unfolding on layers of the brain and mind, however you’re not yet open enough – mind and body doesn’t trust enough to allow you to feel vulnerable enough, to be fragile, to allow your ego mind to let go enough – for the energy and experience of being conscious in/experiencing a place where time and space doesn’t exist, where present moment construct doesn’t exist. Others may immediately be open to this experience and experience pure vividness of bliss as an innocent happy baby, to pure ecstasy, to processing childhood trauma that was too overwhelming for your nervous system, to edging on or being in pure terror for a period of time – an experience you may have to come to terms with, darkness, in order to understand the greater picture and balance between light and the absent of light – darkness. For some the trauma is so deep, so early in childhood, especially for those who are more intelligent and more sensitive – they are more fragile and susceptible to trauma and stress in their environment – including simply a lack of love, that it could take 10+ years of silent meditation to maybe break through to those layers – allowing your ego mind to disengage for long enough and not reenforce itself with distractions like active learning, business ventures, sex, food, and so on. These mostly plant based medicines I speak of, they should be allowed, however a caution to include is that there isn’t anyone I have met – shaman or otherwise – who properly and adequately supports and teaches how ; I should note there are treatment centres of longer programs in places like Peru for treating heroin addictions and such, using Ayahuasca and/or Iboga – how efficient they are I’m not sure, and how well the people integrate back into the place where they reached such an imbalanced and dis-eased point is also unknown to me. I’m lining up the ideal stem cell treatment at a clinic in the Cayman Islands where they will be able to treat the majority of injuries I have leading to central sensitization, chronic pain that causes severe holistic disruption to the nervous system, and once I am healed enough I will develop the platforms to educate people, guide them safely through a funnel, protocol, to develop their self-awareness, to gain and maintain their health. I’ll write a book along the way to share my story, the challenges I encountered with the healthcare system, my proposed solutions for the foundational issues I see, and the online platforms I’ll develop providing practical tools to people. For myself, part of my healing journey – and journey of learning through suffering, the greatest teacher – was Ayahuasca ceremonies breaking down my ego mind coping mechanism that protected me at an early age from an injury, blocking my proper perception of pain and emotional reaction – that continued to abnormally develop, allowing me to injure myself throughout my life more than I realized, and until the pain became uncovered and I became exposed again to an intolerable level of pain; the majority of people’s ego mind being slowly dissolved, usually by a series of ceremonies, uncovers and reconnects them to suppressed/repressed emotional trauma, which then as an adult with more knowledge and coping skills as an adult – more language to process and understand, allows the emotion to come up and then be processed and settle, allowing the ego mind’s activation to diminish, towards dissolving, as well.I’ll leave whoever read this with something lighter, a hilarious video “Using Ayahuasca – Ultra Spiritual Life episode 5 – with JP Sears” – https://www.youtube.com/wat… – most of his other videos are hilarious too.

    1. Richard

      You comment “lining up the ideal stem cell treatment at a clinic in the Cayman Islands where they will be able to treat the majority of injuries I have leading to central sensitization, chronic pain that causes severe holistic disruption to the nervous system, and once I am healed enough I will develop the platforms to educate people, guide them safely through a funnel, protocol, to develop their self-awareness, to gain and maintain their health.”No matter the result, the sample size n=1 to use stem cells to a vague outcome is simply not possible. Before you spend $$ on this think about the trial with a bit more scientific vigor.I’m sure Jerry’s book – like the others before him – will add value to someone’s life, but always keep Survivorship bias in mind – as in how many people read a self help book and get nothing from it.

      1. Matt A. Myers

        I appreciate your caution. I’ve spent ~$100,000 CAD on stem cell treatments over the past 3 years – they work, and more potent once you find a doctor/clinic who actually knows what they are doing; this is the crux of the problem at the moment, a lot of positive news and new demand for stem cell treatments – people in pain being the most desperate and willing to spend money, along with people who want to jump on the money train and learn a little bit because their doctor title allows them to fit into the equation just enough, along with a lot of misinformation out there. I know more about stem cells and the state of current knowledge than most, the difficult part is getting access to the most ideal treatments – not just from the monetary aspect, but because I am a unique complex case and regenerative medicine is relatively new, doctors and clinics offering the less common treatments want to stick to specific protocol they’ve developed.I wouldn’t have spent more than the initial $4,000 CAD the first treatment 3 years ago cost me if it didn’t have significant positive benefit, actual healing that occurred – I would of instead ended my life then because I was too desperate and in too much pain. I’m still in a lot of pain however as treatments have been able to target more tissues to heal more areas, my irritability and the executive function disruptions the pain caused have diminished each time – allowing me to focus longer, recover faster from agitating the physical pain, and allowing the central sensitization – my nervous system to recover faster, and more detail that I won’t outline here of how the benefits of reducing the pain cascades positively.The problem as to why I need the Cayman Island protocol created from the same clinic I have already been to twice in the US, who definitely know what they are dong, is because there’s limited stem cell concentrated fluid available (bone marrow aspirated, bone marrow sucked out of bone from both sides of Iliac crest – along with some post-processing) and therefore limited areas they can treat at once, then generally requiring 6 month wait between treatments. The ideal solution, assuming they accept me for the protocol and unknown what areas or how many they can treat at once, is to take your own bone marrow and culture it for 2 weeks – so instead of say having 500mm stem cells available, there would be 100B stem cells – so more stem cells and more fluid to inject in more places; plus the work and energy use of the stem cells duplicating happens outside of your body, so the healing/regeneration can happen faster as well. Alternatively I wait 6 months between each minor improvement, only targeting up to 5% of tissues in pain – and stem cell injections are very site specific, so if you miss the tissues in pain then you’re shit out of luck until the next treatment – and slowly going crazy knowing you have another 6 months of just waiting in still a high level of pain; the bone marrow aspiration/extraction isn’t the most fun on its own either, so if I can avoid doing more than necessary then that’s another positive.Good point about Survivorship bias. People are only ready to hear and learn what they are ready to hear and learn. This is why with my approach I believe diagnostics, actual concrete evidence that something is going on that can be treated following specific practices or treatments – with followup diagnosis showing improvement-to-elimination of dis-ease/symptoms is the best way to lead. Placebo effect can have value as well, however people can also delude themselves – the ego mind is great at giving itself a pat on the back to make one feel better – perhaps making them believe they’ve been doing deeper worker. I also believe keeping the knowledge behind a paywall or being a gatekeeper of sorts is immoral – it also does nothing to build trust with the individuals researching potential solutions.

  8. sigmaalgebra

    Gee, all that from Paris!You are reading AVC for a reason. Yup, here is why came to and stayed with AVC:My career is applied math and associated computing, and early in my career around DC, for work in US national security, that career was good — at one time my annual salary was 6 times the cost of a new, high end Camaro. Today that would be $250,000+ a year.Once early in my career, I was in GE where I learned a LOT, actually still relevant, really, with the progress in computing, more relevant than then, drinking from a fire hose (numerically exact matrix inversion, numerical linear algebra with double precision inner product accumulation and iterative improvement, numerical linear algebra with interval arithmetic, orthogonal polynomials for numerically stable curve fitting, Gauss-Seidel, Kolmogorov-Smirnov, the fast Fourier transform, Kalman filtering, etc.) but where they were no longer doing well as a business. So I sent some resume copies and in two weeks went on 7 interviews and got 5 offers. Since then I learned that for someone in technology and over 45, and the most capable of their career, can send 1000+ resumes and get back a great silence. Age discrimination in technology is severe.So, with good capabilities, I should quit trying to have someone else create a job for me and, instead, create my own job — be an entrepreneur, start a business.Lots of people do that, with only a small fraction with venture funding. So, e.g., can run a big truck-little truck business where buy in large quantities with a big truck and sell in small quantities via little trucks. At times, for a while, could do well with that, as I grew up, beer (a guy down the street who a little later did well in much of NW TN), candy (my brother’s family), liquor (a guy in the next house to the NE). For more, there was rebuilt auto parts (a guy next door to the east — with his family built a significant business), a guy two doors to the west (scrap metal, later relocated to Birmingham, AL), a guy on the other side of the street about 8 houses to the west (a magazine for the trucking industry, and with a daughter 4 years younger than me), family of a guy my age in school (built lots of affordable houses, with a partner started some seafood family restaurants, got into the motel business, i.e., started Holiday Inns), a guy four houses to the west (cotton business, out in the sticks in TN, buy cheap from the farmers and back in the office sell to the cotton mills), a guy I knew when I was a B-school prof (kill 5000 hogs a day and ship boxes of cuts to grocery stores in NYC), another Memphis guy I knew (started FedEx that I saved for him twice with some computing and applied math), etc.So, what business was I going to start, say, with math and computing?(1) I’d been doing expert systems artificial intelligence for monitoring servers and networks and cooked up some math, algorithms, and software for a much better solution. Looked good on some real data and really good on some really challenging synthetic data. So, sell that. Gave a talk at the main NASDAQ shop in CT. So, contact some VCs, get some funding, and go for it. Nope. No VCs interested. So, I published it in Information Sciences.Okay, Dean of Science at MIT gave a lecture on optimization of the design of the larger parts of the Internet. The lecture he gave was in a series named after the prof who chaired the committee for my Ph.D. orals. I knew quite a lot about such optimization, looked for VC funding, and got back only silence. I got an interview at a startup in Dallas trying to do that, but they were falling apart and soon closed.So, trying to understand what VCs wanted, I discovered AVC.Eventually, if only via massive trials contacting VCs and process of elimination, I concluded that I had nearly everything VCs wanted except traction. Okay. Now I understand.It took me a while to understand so clearly: Lots of VCs on their Web sites passed out lots of advice, presumably from what they wanted in investments: Eventually I had to conclude that the advice was deceptive and just a form of bait to get technology business tutorials but that the real “Secret of Silicon Valley” was that for writing a check the key word was just traction. Okay. Now I understand.It also took me a while to understand because in my work in US national security and in research projects are approved and funded just from proposals on paper and long before anything like traction.But at AVC I started to learn more, maybe not about VC funding but about entrepreneurship. Okay.And occasionally I got some feedback on my guesses at topics in business.But once I learned about VCs and traction, I cooked up a business I could fund myself. The main reasons the business is cheap to start are (i) I’m a sole, solo founder and (ii) the computing and data communications for my business idea are now shockingly cheap. Moreover, since I have a background deep enough in each of math, computing, and business I should able to get the key traction by myself.Then if I do get the traction VCs want, I will also have a nice life style business I want. If people like my work enough for the business to grow to something big, even better. But nowhere in there do I anticipate a need for equity funding, a need big enough for me to report to a BoD that could fire me. Apparently that was the situation for the guy who started Plenty of Fish.Or, the businesses I mentioned I saw growing up, none of them got equity funding, and my business, if don’t value my time, is much cheaper to start than theirs, e.g., the capital expense, capex, I need is just a computer from $2000 in parts, and the operating expense, opex, is just a routine Internet connection (with a static IP address) and some electric power, about that of 3 old light bulbs.Am I making a mistake and should quit? (1) Well, common advice is quite generally, no, don’t quit. (2) In particular, I’ve got the software apparently ready for significant production, if people like it, good enough for ballpark $250,000 revenue a month — life style business. In general, what I’ve got looks closer to passing the KFC Test, “finger lick’n good”, than any of the examples I mentioned above. So, I should keep at it.The AVC content helps in those judgment calls.And so as part of that interest, I would recommend you pick up Jerry’s book and get inside the head of one. It will flip some switches on for you. So, that’s more background work, to get ready to work. Counting my Ph.D., time in businesses, as a B-school prof, doing applied math and computing, I’m awash in background and need to get on to traction.As in the movie In Harm’s Way, at some point have to quit getting ready for the big fight and get on with the big fight.For“radical self inquiry”: withBut the most challenging piece of the formula — indeed, the most important — is the notion of radically inquiring within. I define it as the process by which self-deception becomes so skillfully and compassionately exposed that no mask can hide us anymore. I’m trying to be successful in business, e.g., ASAP to traction.As we know well, on the Web it’s tough for the users to know much of anything about me personally. So, to be successful, basically, necessary and sufficient is that I need to please some hundreds and then, ASAP, some thousands, millions, and billions of users.Yes, maybe I am blocked by “self deception” and, thus, need to expose and correct that. Maybe. But, several times in my career I’ve done good work, with all the intended success, on directions that looked risky at the start. My current project looks no more risky than those. Moreover the software does appear to run as intended — no surprise since I’ve been successful writing software, just from routine effort, for all my career. Also, in simple terms, the work is just a Web site; millions of people have brought up Web sites, and I should be able to do so also. Then why should my site please users? The site is to help people find, say, 2/3rds of the Internet content (safe for work, families, children) currently served as best poorly by Google, Bing, etc. So, fully successful it should be worth $1 T; for now and soon, I’ll be happy as a clam with just $250,000 a month. So, I’m hoping to get $250,000 a month from a business that, ballpark, should be worth $1 T. So, to me this doesn’t look like I’m being blocked from success by “self-deception”. Okay; okay; the $1 T is too big by a factor of 1000. Fine. I’ll settle for $1 B. Still $250,000 a month doesn’t look absurd.More generally, since most successful new businesses looked risky when they were started, I should expect that in part my new business would look risky.The notion is to recognize that, if things are not okay, if you’re struggling, you stop pretending and allow yourself to get help. All the work unique to my startup has been fast, fun, and easy for me.Problems:(1) There was learning Microsoft’s .NET software tools; that was find, download, read, index, and abstract 5000+ Web pages. That took a while. I also have a few cubic feet of supposedly relevant books — one of them was helpful as a start.(2) There was get around computer system management problems from bad software and/or bad documentation. It was mud wrestling.(3) A pill some doctors gave me that put me to sleep for 16 hours a day. I figured out that the problem was not me but just a pill, what pill that was, quit taking it, and have done fine.With these problems, I don’t believe I’m “pretending”.Even more, it’s the process by which you work hard to know yourself — your strengths, your struggles, your true intentions, your true motivations, the characteristics of the character known as “you.” Dirt simple: Get some business success, i.e., lot of after-tax income, necessary and sufficient.The you behind the masks, the stories, the protective but no longer useful belief systems that have been presented for so long as the “you” that you would like everyone to see. Yes, there can be a point here: In trying to understand my late wife’s “struggles”, I did learn about “belief systems” and “presented … like everyone to see.” Generally she, her mother and sisters, were all determined and consummate actresses even beyond the approaches in E. Goffman, The Presentation of Self in Everyday Life, an obscure book but fast and easy for her and all of which was foreign to me. She knew more about that than Goffman!Invariably such inquiry involves getting to know, as the poet Adrienne Rich says, “not the story of the wreck but the wreck itself.” With help, patience, courage, and guidance, we explore the wreck and retrieve the treasure. This likely qualifies as intervention which, generally, is uncertain in the results and can do harm.Knowing how to survive and understanding what it takes to thrive are skills that come from our childhood. Only in part, and much more can and, thus, should be learned along the way.Take any random group of entrepreneurs, for example, and do a quick unscientific survey by asking them to raise their hands if they grew up in an environment where at least one parent had disappeared or left or was never present. Most hands will shoot up. Yes, it is “unscientific.” And first cut, even if take that claim at face value, is the fraction unusual for the population or for more relevant parts of the population? That is, is there anything different?Early promotion into adulthood is often painful and equally often a sign of an early promotion into leadership. That is a conjecture in sociology or the theory of that field. My wife’s Ph.D. was in mathematical sociology, that is, addressing such questions with mathematical models and in particular with statistics on such models, as in the work of two of her profs, J. Coleman (as in Brown v Board of Education) and P. Rossi, both with terms as President, American Sociological Association.Generally such statements in sociological theory are NOT easy to confirm with statistical significance.E.g., my wife’s Ph.D. dissertation was on the theory that executives in organizations became more conservative in their decision making as they gained in responsibility. She had some survey data and addressed the question. The theory looked obvious; showing it was NOT easy.We know; we know; Trump as POTUS is much more careful in making decisions than AOC as a newly elected Congressperson. But that little observation is a long way from confirming the claim.Probe a bit further and you may find that leaders who have built their company may have unconsciously stacked the team with other folks who experienced such early promotion. This is another guess in sociological theory likely difficult to confirm. To take this seriously, we should not have just “may find” but some actual tests with data.Radically inquiring within allows us to step back and see the patterns of our lives not as random acts of a willful or even vengeful God but as forces that shape who we are. Not so promising: It does appear that life is heavily influenced by strong, unpredictable, exogenous influences. And, super tough to prove that God (there must be one; I didn’t build this universe; if I had, I’d remember it!) is “willful or vengeful”. Building all this universe does look like a LOT of work for what the heck reason?Jerry started his career as a writer and he is a wonderful one. My problems with “writers” as in belle lettre is that (i) they rarely made very clear, nowhere nearly as clear as in math or physical science, what was significant they were claiming was true and (ii) gave meager or no good evidence about anything being true.Ah, back to work!

  9. Donna Brewington White

    You had me at “Jerry Colonna”Of course I will read this.Of course I will share it.

  10. bsoist

    one of the best people on planet earth.Indeed!Many people have shaped the way I think drastically but I believe Jerry holds the record for “impact per word spoken.”