What Does A CEO Coach Do?

Jerry Colonna, who should need no introduction to this community, did an interview with TechBerlin in anticipation of his workshop there next month. The first part of the interview is a bit of background on Jerry, but the part of this interview that really grabbed my attention is the middle part (about five minutes in) where he starts to talk about what a coach is, how coaching works, and why it works. If you’ve often wondered if you could/should work with a coach, watch this interview.

SKYPE A FOUNDER #6: Jerry Colonna, Professional Coach from TechBerlin on Vimeo.

#VC & Technology

Comments (Archived):

  1. jason wright

    I watched this only yesterday. Small world. I liked the Nietzsche pathway reference. How old is Jerry by the way? His Wiki entry is not saying too much – reputation management perhaps ha ha :-). I’m thinking of going to his Berlin talk, although I missed out on the ‘early bird’ discounted price of Euro 169 – a pity, but sleep is important and Jerry recommends it. 

    1. jerrycolonna

      He’s like 90. Can’t you tell that from the dark circles under his eyes?;-)Actually…47.  I don’t spend much time on wikipedia, facebook, linkedin, et al.  

    2. fredwilson

      he is in his mid/late 40s

    3. Steven Kane

      that colonna is a youthful bastard with an old soul

      1. jerrycolonna

        and handsome. You forgot to add that.

      2. fredwilson

        Nice description steve

  2. Joe Yevoli

    I wish every entrepreneur had a chance to sit down and talk with Jerry.  He’s definitely one of, if not the most influential person I’ve met since starting a company.

    1. jerrycolonna

      You da bomb, Joe.

      1. Joe Yevoli

        Ha, and clearly Jerry is up on the current lingo 😉

        1. jerrycolonna

          Despite being 90.

  3. Kasi Viswanathan Agilandam

    As an entrepreneur does everyone need a coach. Is it not the dream and passion which drives the entrepreneur? Larry Page may need a coach NOW but not when google was becoming GOOGLE. Now it is all about managing the money he and google got … being more smart with the  cash handling THAN being a entrepreneur.Do we need a coach to make our dream come true? Unless it is about how to make smart money out of your dream … any entrepreneur does not need a coach. Follow your heart and your passion “COACH” will be born inside you.I may be wrong … 

    1. jason wright

      Perhaps it’s just the word ‘coach’ that throws you. Mentor? 

      1. Kasi Viswanathan Agilandam

        Yes. The word Coach is the issue for me i think.  It does not suit this operation IMHO… there is this word called “CEO at residence” … i got totally confused when i first heard about it and then got pissed off when i knew the meaning of it. .. some lingo irritates and i expressed that in my own words.Guide would be a better word…. as in thesis guide and tour guide … where he helps you when you ask for help … or he guides you when you are entering a uncharted territory …  not like a coach who train you how to maximize your goal scoring (home-run) ability on a day-to-day basis.Kevin: I am a strong believer of ” what we know is just a handful of sand and what we don’t know is the entire land mass of earth”.  I did not mean to offend anybody’s profession … it is just the in-appropriate word… 

    2. Kevin Friedman

      Yes, I agree with jason that perhaps the word “coach” might rub some people the wrong way. Kasi, you said, “follow your heart and your passion and “COACH” will be born inside you.” This question seems to imply that we can can deal with all problems on our own. Do you believe this?I would argue that a good coach will actually bring to life the “inner coach” that you speak of in your comment. Unfortunately, many of us, need a little help on this journey… whether it be from a life coach like Jerry, or a “mentor” like jason mentioned, in order to truly follow our hearts and our passion.

  4. leigh

    My business partner and I included a piece in our company agreement (while we are all getting along) about an agreed upon coach as a means of mediating conflict.  We were lucky enough to be introduced to one of the best in Canada who is absolutely incredible and has become a huge support to us in our early stage.  She’s helping us set up HR, various org policies, has made introductions for us with like minded executives/people and is a coach to us as a team and as individuals.  It is the best thing we’ve ever done.  

    1. jerrycolonna

      What a brilliant idea. I wish all business partners would anticipate such challenges before going into business together and craft agreements about how to handle things when disagreements arise.Fred and I did a little of that when back when my hair was black.

    2. Matt A. Myers

      Care to share who? 🙂

      1. leigh

        Karen Wright 🙂 

        1. Matt A. Myers

          Thanks much. 🙂

  5. Kevin Friedman

    Wow, what a treat to watch this morning! Fred, thank you for sharing this! If Jerry speaks to you, you have to check out his blog The Monster in Your Head to learn more about Jerry and read many thought-provoking and inspirational thoughts and stories.Jerry really understands the unique creature we call an “entrepreneur.” And, sometimes just being “understood” is extremely helpful and healing. I attended his NYC workshop in May and it really was life-changing for me to hear Jerry speaking about the issues I have struggled with in the company of fellow entrepreneurs. What an amazing shared experience! If you live in Europe, you have to attend his upcoming workshop in Berlin.

    1. jerrycolonna

      Thanks Kevin.

  6. Fernando Gutierrez

    That’s a great video, thanks!With coaches I have a question I’m not capable of answering myself: can someone be a good coach to a person in a position the coach has never been in, or at least something related?My instict –and I think that most people’s– says no, but when I try to rationalize why, I’m not so sure. Many of the things Jerry mentions are not aquired doing what the coachee does, so unexperience in the specific job should not be a deal killer… But then choosing becomes almost impossible with so many people out there calling themselves coaches!

    1. jerrycolonna

      You raise a really interesting point, Fernando. I do think that one ought to have some core life experiences, relevant to the endemic group you’re trying to work with, in order to be of maximum help.That said, the most powerful tool a coach has is the question. Coaching is NOT advising or mentoring (although sometimes advice and mentoring is used)…coaching is really about helping the client get to the next level through inquiry. And smart questions can come from someone who may not have had direct experience.And those with direct experience may not necessarily make good coaches.

      1. Fernando Gutierrez

        Good points. Socrates must be really happy in his grave!

    2. fredwilson

      i think the coach doesn’t need to have done what you are doing. he or she just needs to help you figure out what you are struggling with and why



      1. jerrycolonna

        EXACTLY. One client said to me, “Oh I get it. You do pattern recognition.” 

        1. FAKE GRIMLOCK


          1. panterosa,

            Like biomimicry, no?

          2. FAKE GRIMLOCK


          3. panterosa,

            I am designing a games and toys series for exactly that – pattern recognition to decode evolution (life). From infant on up, using botany and zoology as visuals, and reading about complexity to simplify it into small bites. I address pattern recognition in visual and other modalities to lead to quick connections and solutions.Do giant robot dinosaurs like games?

          4. FAKE GRIMLOCK


  7. markslater

    talking with jerry for people in the stage of entrepreneurship where i find myself today, would be a privilege. I am not sure how the economics would work.i have found that the advisory board approach is extremely useful. for what its worth here is what i have done: I have appointed 7 advisors – each one of which is an expert in a particular discipline (think – finance, strategy, tech, customer, etc). As and when issues come up – i tap the appropriate advisor for help. Its a bench of expertise that the company does not explicitely “pay for” or need to hire full time. We have just closed our first real seed financing and i am being pulled in a bunch of different directions – but my focus is on achieving 3 specific goals – anything else right now is nice to have – and i bring an advisor in to discussions that fall in to this category (we are participating in discussions on an emerging concept called VRM at harvard – and two of the company’s advisors are active in these discussions)We are close on our CTO hire – the final hurdle will be several of the advisors spending time with  each individual and providing opinionSo – coaches are great – i am not sure at our stage how this would work for us. But i do know that the advisory board approach has been extremely successful for us and continues to be my source of ad-hoc – “coaching”.

    1. jerrycolonna

      Mark…you may be getting all you need from your advisors. In some of my talks, what I say is that we all need our “Elders”–advisors, good board members, allies, peers…folks who can help us separate ourselves from our own craziness and see things a little more clearly. As I said in the video…the real opportunity is to make certain one is asking oneself the right questions.

      1. markslater

        well i feel like i am on a bit of a speed boat heading in to a stiff wind at times not sure what the weather is like ahead!if you are ever in Boston Jerry it would be my privilege to buy you a coffee.

        1. Matt A. Myers

          Dense excitement from the unknown? Just set intelligent milestones and as you reach each one allow yourself to feel reassured you know what you’re doing.

          1. markslater

            its 1130 at night and i am replying to you! – i have chicane on my headphones and i am enjoying reading and responding to the discussion. i enjoy doing this, its calming.

        2. jerrycolonna

          I’ll keep that in mind. And ping me when you’re in NY. I’m too often too busy but always love connecting with folks.

    2. Kevin Friedman

      Hi Mark… It sounds like you have a great advisory board with experts in many fields. It makes me wonder… do you have an “expert” in, for lack of a better word, “personal” issues? Where would you go if you (or your partners) were, say, feeling burned out… overwhelmed… or maybe just wanted to check-in and share how you are feeling? I don’t think there is usually an advisory board member for these purposes as they are not usually valued in the start-up world.

      1. markslater

        i grab my daughter and walk her around castle island twice with cafe del mar on my ipod. I do it as often as i can

      2. JamesHRH

        Kevin – I may not be 100% bang onhere, but Brad Feld suggests a People Executive. Not just HR, but a person that does what you are asking about, as well as checking / ironing out / tuning senior team dynamics. It makes a ton of sense to take it off the CEO’s desk, as that person is too close to the trees…..



        1. Donna Brewington White

          I like that — Startup Gandalf.  We could also use a Fake Gandalf around here.  Same initials as Fake Grimlock.  I bet you could pull it off. Use all small letters. BTW, were you “mass man”?

          1. FAKE GRIMLOCK


          2. Matt A. Myers

            “Use all small letters. “*bursts out laughing*

        2. Donna Brewington White

          …and also, that’s an intriguing analogy — Gandalf as VC.

          1. FAKE GRIMLOCK


    3. awaldstein

      Seven seems like a lot really. I’m presuming these are equity based?

      1. markslater

        its not that many to be honest. i looked at it very simply.there are 7 disciplines i have to cover. I am not an expert in 5 of them and i cant afford to hire. But i’m sitting on a monster opportunity in VRM and i need help.they all invested as well.

        1. awaldstein

          Advisers as investors…good plan.

          1. markslater

            no such thing as advisors for hire.founding advisors are fierce believers that happen to have a (day) another job

    4. Dave W Baldwin

      Congratulations Mark!

    5. Matt A. Myers

      Firstly congrats!Secondly, 7 advisors seems like a lot of advisors. I can see they could full quite a broad spectrum, however I’m not sure they’d all be able to be kept enough in-the-know to have more relevant responses?

      1. markslater

        i’ve seen some start ups with over 20 – no kiddingits up to us to keep them involved, engaged, and effective.

        1. Matt A. Myers

          I’m curious about how advisors lead to being investors; Maybe if you want to chat sometime about it? Just curious how that looks/looked in your case – if you strategically planned who you picked for advisors with hope to getting involved people (who you don’t have to explain further what you’re doing) before asking them if they want to invest?

          1. markslater

            hey there matthew – if you want to ping me at mark at getabl dot com = we can take the chat over there.

  8. Jedd Wright

    Yike! Jerry really seems to hate being a banker/VC. Hopefully he is in a better place. But…the subtext is do what you LOVE. Don’t just go after $$$.Teaching is great, and fulfilling.

    1. jerrycolonna

      Actually I loved being a VC (was never a banker and probably would have loved that). But the reasons why I stopped had little to do with whether I like it. It was just time. And I needed to listen more deeply to my own soul. I’ve also been a journalist and a teacher and a writer and I ran my own Internet based business. Someday, I’ll do something else and won’t have hated a single moment of being a coach.

      1. Jedd Wright

        Good to see you teaching. The problem with coaching is that it’s hard to measure the success of brining on a coach.If you can come up with a measurement platform with coaching, then I am in.I run a small biz with 8 people. Need CEO help, but consultants just pitch bullshit, so we pass.

        1. Fernando Gutierrez

          Talk to people who also run businesses of similar size. Problems are comparable many times and it feels great.

          1. jerrycolonna

            Great advice, Fernando.Jedd, I think coming up with a measurement tool for services like coaching would be the Holy Grail. Wish it were possible.In the end, the only real metric is how people end up feeling. That’s one reason why I’m a pay-by-the-hour and pay-as-you go kinda guy.

          2. Kevin Friedman

            Jerry… when you first meet with your clients do you define coaching goals together? Is there a way to quantify a person’s progress towards and, hopefully, their achievement of these goals?I guess it might be hard if the goal is more of an emotional goal and then somewhat unquantifiable.Just thinking…

      2. ShanaC

        Do you ever have moments where that experience helps CEOs pivot?

        1. jerrycolonna

          All the time. But it tends to be more relevant for people who are scared about making a career shift (Despite the intensity of the focus on them, CEOs make up only about 40% of my clients. There are many folks who are just struggling with the everyday challenges of sorting out what they want to be when they grow up.)For those folks, I’m living proof that you can re-brand and re-ignite (time and time again). There was a time when people couldn’t see me as anything but a journalist. And then a VC. And now coach.

        2. Matt A. Myers

          Top 5 — Look at you go girl!!

          1. ShanaC

            I rather just be more helpful to people who are new….

      3. Matt A. Myers

        Just curious – do you invest at all now?

        1. jerrycolonna

          a little. rarely. I stopped entirely for a few years and did some angel investing just recently. but it’s very hard for me as I don’t like to NOT be engaged and it’s very hard for me to BE engaged.

          1. Matt A. Myers

            That’ll cause some cognitive dissonance / frustration for ya. 😉

  9. jerrycolonna

    Thanks for the link Fred. The audio-synching problems aside, it felt good to explain in some detail what coaching all about.

    1. nikolas woischnik

      Hi Jerry, I am just uploading a new version of the video to Vimeo where the synch is fixed. I wish I could have finished that yesterday night, but Murphy’s law seems to have been at play :-). 

      1. nikolas woischnik

        Here the fixed version: http://vimeo.com/27817121

    2. David Noël

      Loved it, Jerry! Thanks for doing this interview and thanks Fred for sharing it with Fredland. 

  10. Shawn Cohen

    Our company has taken coaching to the student level by helping them to take on an entrepreneurial mindset while still in high school and college. Our staff is not tutors but people who are there to keep the student accountable to meet the goals they set for themselves.The goal for our students is two-fold and it closely parallels Jim’s answer to the interviewer’s late question: Is it the path or the goal? Our students do a lot of assessments that help them become self-aware and learn how to set goals. Over time we see them becoming more aware of opportunities that are worthy of goal setting.It’s encouraging to see some validation for this concept from someone like Jim.

    1. jerrycolonna

      Jim? Did you mean me?Love the concept of your company.

      1. Shawn Cohen

        Haha, I apologize, Jerry. Yes, I was totally talking about you. Thanks again for your thoughts on coaching–there’s such a big need for coaching on many levels today.It’s great to hear more voices joining the chorus.

  11. Terry Ratchet

    Cool interview, lots of insightful info

  12. reece

    Jerry’s the manwe worked with him a bit during TechStars and it was really helpful for us as a teami feel very lucky to know him

    1. jerrycolonna

      Yeah but Joe is Da Bomb. 😉

      1. reece


  13. David Noël

    Loving the 1/3 balance: 1/3 for the inner, 1/3 for the outer, 1/3 for the other. 

    1. David Noël

      Here’s another one: asked what Jerry thinks is more important; the path or the goal, he replied with: “Stay mindful of the goal and focused on the path is probably the right combination.” Nice.

      1. jerrycolonna

        🙂 Thanks. But THAT bit of wisdom also comes from my Buddhist training. I’m just channeling much, much wiser souls. 

    2. Kasi Viswanathan Agilandam

      I love it.  … 1/3 …. it never works. 1/3 > 1

    3. jerrycolonna

      That came courtesy of one of my teachers. I am just as susceptible as the next guy to losing my footing, losing my way. Maybe the only difference is that I admit it. 😉

  14. Adrian Bye

    jerry rocks and is a critical leader in the NYC tech community

  15. BusinessPartners

    This is a very insight-rich interview. In decades to come, I expect CEO-coaching to be a much more talked about and used service among the executive community.

    1. Tereza

      Smart companies may not talk about it, but they all do it.  Above a certain level, all the people on that trajectory are coached.  It’s essential, to achieve a certain level of play.  But a lot of startups don’t really know about it and that’s too bad because they need it the most.My husband is with one of the major professional services firms. It’s pretty much a requirement that every partner has a coach.  In that environment where everyone’s in the same boat for the long haul, you have to work out your shit otherwise it goes projectile in all directions in about five minutes.  The financial investment they’ve made into coaching on this scale is breathtaking (imagine a master svces agreement covering a few thousand partners with a large number of top-tier coaches).  But they’ve run the numbers and apparently it pays off big in terms of business performance.So my husband was recommended for coaching a year ago — which at first he viewed as a punishment.  They explained with the numbers described above that it’s a huge investment and they only do it if/when they think you’re worthy of getting to the next level (otherwise they cut you loose).  The person he got matched with is a former olympic-level gymnast.  He was skeptical at first. But boy has she done great things for him.Coincidentally, I started working with Jerry a year ago.  It’s benefited me and the business — I’m sure of that.  But more importantly, this convergence has done really good things for my marriage.

      1. fredwilson

        You have to work out your shit otherwise it goes projectile in all directionsYou have a way with words Tereza

        1. Tereza

          I aim to please, Fred.I figure every comment should either: provide insight, piss someone off, or get a laugh.  Preferably all three.That’s my goal.

          1. fredwilson

            that’s why you are a top ten commenter at AVC

          2. Matt A. Myers

            Full agreement here 🙂

          3. Tereza

            awww shit I dropped.  Used to be top 3, not that i’m counting or anything.  Been distracted with all this start-uppy stuff.I take my Disqus performance very, very seriously.

          4. Matt A. Myers

            You’re still top 3 AVC’er in my heart Tereza. 😉

          5. Tereza

            Good.  Cuz “Top Ten” ain’t good enough.  😉

          6. fredwilson

            just checked. you are #3JLM #1FAKE GRIMLOCK #2Tereza #3the awesome Arnold Waldstein #4Shana and William tied for #5i don’t like ranking my friends but disqus does it so i figured i’d share the results

          7. Tereza

            Awww.  I love ’em all!  {warm fuzzy hug}But, uh….no offense Fake G — when I have more time, your days are sooo numbered. GRRRRR.  And JLM — I’m willing to look the other way on your complete Disqus Domination because you suck so bad on Twitter.  Just sayin’.(Can’t have a pickup game without a little trash talk)

          8. Donna Brewington White

            Based on your comment below, I’m wondering why this doesn’t this show up in the “community box”?  FG doesn’t even appear there and he is a #3 commenter.Also, I wish I didn’t appear there since most of my comments are actually replies.  Doesn’t seem like replies should carry the same weight as initial comments.  

          9. fredwilson

            i think this whole rating system is about to get rolled out more holistically

          10. FAKE GRIMLOCK


          11. Guest

            @Tereza:disqus had to find a post that allowed me to make a reply to your @JLM:disqus Twitter comment because it totally made me smile.

          12. Robert Thuston

            This discussion with Tereza turned out to be timely with the roll out of the individual Disqus rankings……as well as Leigh’s comment on the “Skillshare” post about creating a reputation across the internet, similar to “badges” created on Stack Exchange…The discussion Leigh opened, I think, is one of the most interesting on the internet.

          13. Donna Brewington White

            I think you succeed very well in this goal, my dear. I always love when you show up in the comments because I know it’s going to be more interesting and more fun — and I’m gonna learn something new — every time!You haven’t personally pissed me off yet, but I have a high tolerance level.  😉  

          14. FAKE GRIMLOCK


      2. ShanaC


      3. panterosa,

        Tereza,I am fascinated by an olympic level gymnast in coaching. It makes so much sense, even if a very unlikely progression. Is there more back story on this? I was a gymnast years ago, and actually could have benefited from more coaching then. Not that I was olympic bound, due to age, nor encouraged (see intellectual parents).

        1. Tereza

          Well when my hub was assigned her he was like — WTF? But the point is that, like Jerry, she worked under extremely strenuous circumstances and achieved the highest levels of performance in her field. She trained under Bela and Marta Karolyi — Nadia Comaneci’s coaches — at the US olympic training center. Obviously you can’t be a gymnast forever so this is what she picked next and is excellent. They spend a lot of time talking about personal styles and motivators, such as management via fear, via encouragement, intrinsic and extrinsic motivators. What are the nuances of each, what works and what DOES NOT. Essentially how to get the most out of specific people that you work with given their own style, and what kinds of buttons they may be pushing in you based on your own style. And how are people perceiving you. Also when you have trouble with a certain person, deconstructing why it’s not working and coming up with an action path, or sometimes, it’s validation that the other person has big issues so stay away. 🙂

          1. panterosa,

            Tereza,Thanks for fleshing out the gymnast coach. A very interesting approach. She sounds fascinating.

    2. jerrycolonna

      As biased as it may sound, I agree. I wish I had had a coach myself way back when I had hair.

      1. Tereza

        Honestly, now, Jerry — if you want, I can set you up with the top follicular dermatologist in the country.But you don’t need it.

  16. Josh Liu

    Sorry if I should not ask Jerry questions here. It seems Jerry is here responding to the comments. I am a London based entrepreneur, and I am sure a lot of entrepreneurs would be interested in your workshop. Since you are flying all the way to Europe, will be you interested in running another workshop in London?I can help to make it happen. CheersJosh

    1. TanyaMonteiro

      Hi Josh, I’m also based in London and travelling to the workshop. Here’s a meet-up site that I set up to get the word out. If you know more people that might want to go please forward details, make changes etc. http://www.meetup.com/Start

      1. jerrycolonna

        Josh, Tanya…Mike Butcher of TechCrunch and TechHub is also keen on doing something in London. In our experience planning the workshop in Berlin, it really helps to have a group focused on making it happen. It’s not a TON of work…but it is work.And as I said in the video…Happiness is a passport filled with Visa stamps. 

        1. Josh Liu

          Thanks a lot for your response, Jerry. I am contacting Tanya, and will talk to other entrepreneurs/TechHub in London. Hopefully we can make it happen. 🙂

          1. jerrycolonna

            terrific Josh.

  17. Gregg Freishtat

    Jerry was on two of my venture backed boards – while he was at CMGI and then when he was at Flatiron.  He is far and away one of the best board members I have ever worked with and I am sure he is fantastic coach.  If I could only find the time to get coached, I would be all set…..Gregg FreishtatVertical Acuity

    1. jerrycolonna

      You were easy Gregg. As the CEO of the first company I ever backed as a VC, you were easy to work with (and easy in other ways but this is a family-oriented blog and I won’t go into details here). You taught me a ton. And you made me money. What more can a guy ask for?

  18. Michael Vagnetti

    This is fantastic. Coaching is totally valuable and often underrated.

    1. jerrycolonna

      I agree Michael. But I suspect you may have guessed that.

  19. Joaquín R. Kierce

    Jerry,I moved from Spain to the US ten years ago and I’ve noticed what you say in minute 12 about the tolerance to failure. I can’t explain the tension you feel in my country in all aspects of life with regards to failure.I think that’s at the core of the matter here. Totally agree with you.From coach to coach, thanks for your words, they are a good reminder of how cool this job is.

    1. jerrycolonna

      Hey there…so glad to hear from another coach. It’s remarkable how tough it can be. I’m not saying that folks here in the States don’t deal with an intolerance for failure but part of our collective mythology is the rags-to-riches story (usually of an entrepreneur–even if we didn’t call them such things back in the 19th Century).Perhaps it’s the influence of the Dutch who participated in the colonization of the country (at least that area which became New York) for commercial reasons  or the French fur-trappers…but this focus on making it to the States in order to make it big…well, it’s part of the story we tell ourselves about ourselves.Of course, we can turn on those successes just as quickly. We’re  a fickle people. 

      1. jerrycolonna

        Also, I wonder what, if any, influence a history of socialism has on a peoples’ collective tolerance for business risk. It will be interesting to see, for example, what happens to the next few generations of entrepreneurs in China and India.

        1. Tereza

          I’ve observed that communism plus culture yielded very different outcomes in each place.  So hard to generalize.  For example where I spent time (Prague ’90s) the people had been so skeptical of the socialist structure for so many years, and had compartmentalized their inner and outer realities … this primed them to call BS on anything.  But when I visited other countries I was surprised to see how differently socialism (and post-communism) manifested.I visited Vietnam and concluded that there was no political system on the planet that could possibly zap their entrepreneurial spirit. It inhabits them at the atomic level.The legal structure plays in as well.  Case law, code law, etc.  When I was in Czech it was code and they were literally writing the laws and the judges were learning said laws at the same time while we were doing stuff around those parameters.  Crrrazy!  When I studied business in Germany (in the paleolithic era), it was *illegal* to lead a company to bankruptcy.  What a great way to squash that risk-taking spirit.  Curious whether anyone here knows if that’s changed?

          1. jerrycolonna

            Very interesting perspective. Thanks Tereza

        2. nikolas woischnik

          Jerry, that is a very interesting point and something that you can explore further when you come to Berlin. There are some very successful internet entrepreneurs from the former DDR here in Berlin and they are said to be be very, very hard working. 

          1. jerrycolonna

            Sounds like a great topic for our breakfast discussion on 9 September.

          2. nikolas woischnik

            Damn, still in India on the 9th, but hope to see you before you leave on the 11th! 

  20. Nik Souris

    Thanks for the post Fred! Think Therapist is a pseudonym for Advisor?  I see coaching as a key resource if you can get one to execution! developing and staying on game plan / making adjustments / winning duh! vs. Therapist – who seem more like fans with access / Monday morning quarterbacks. It’s often a bummer when I ask startup CEOs about their Advisers and how they are invested.  Many many more times than not – there is nothing financial at risk – Time may be money – but talk is cheap!

  21. nikolas woischnik

    Hi everyone, I fixed the video/audio synch and you can find the new version of the video here: http://vimeo.com/27817121 

  22. Jeff

    Jerry was a fantastic VC. I think he was once rated a top 5 VC in the Red Herring, a popular pub in the early 00’s. More than that, he is a friend, and great human being that takes a sincere and heartfelt interest his peeps and his pursuits. Kudos to Fred for sharing Jerry on AVC

    1. jerrycolonna

      Top 15 but who was counting? 😉 Thanks Jeff.

      1. AshleyMckenzy


    2. Tereza

      Whoah whoah wait hold on people.  If we’re gonna throw some love around, then listen up.I’ve met a massive amount of really awesome people in the past year.  Jeff Finkle is at the top of the list. (Jerry you came in just over a year ago so didn’t make the cut.  Sorry.  It was a timing thingy.)Folks — trust me — if you have a chance to meet Jeff, take the meeting.  #SuperMensch

  23. ShanaC

    @jerrycolonna:disqus Can you go more in depth about the differences between coaching and therapy – because some of your description sounds like an intense bout of CBT by a guy who did business.Actually, I could see that as a fourth career for you (therapy)

    1. Matt A. Myers

      CEO coaches IMHO are therapists who happen to have specific experiences.I contacted Jerry awhile ago, though realized at that point I wasn’t ready – I had some pre-business coaching therapy to attend to firstly; And my therapist has been well worth it. She’s actually a pretty good at ‘business coaching’ too in regards to certain things she’s helping me figure out.P.S. Just writing this because I think it’s healthy to help destigmatize therapy, etc..

      1. Tereza

        There definitely is a stigma in our society about therapy and it’s healthy for people to know that it’s not only OK but really the right thing to do, to ask for help.  It’s not a weakness.And whether a therapist or a coach (or a psychiatrist or a member of clergy or a friend), some are better matches for you than others based experience and where you want to go.But there are certain areas that a licensed therapist is trained to deal with that a coach is not.  I’m talking pathologies.  A therapist is helping you heal.  A coach is working with you to reach your goals. There’s overlap.  But to send someone to a coach who, say, has PTSD or Borderline Personality Disorder or addiction, doesn’t do either any favors.  They need special training and clinical experience.

    2. jerrycolonna

      Cognitive Behavioral Therapy (CBT) techniques are definitely one of the tools a good coach will use (like “re-framing” and “mirroring” so the client can see things from a different perspective) but it’s not CBT (it can be more inquisitive, more present-moment focused, more tactical). There are some coaches who will use NLP techniques or others who use the personality instruments. I try to follow something my supervisor says all the time: “Does it work?” If it helps the client, I use it. I don’t worry so much about labels.

      1. JamesHRH

        Jerry – I am with you on labels. But I think therapy is a loaded label, in some places. it gets some people’s back up…Is it fair to say that the goal is to have a CEO know themselves, know the situation & get some perspectives from a trusted, outside the fire but experienced source?

        1. FAKE GRIMLOCK


          1. jerrycolonna

            “PSYCHOLOGY IS MATH FOR HUMAN BRAIN.”I want to make that a bumper sticker.

          2. FAKE GRIMLOCK

            DO IT.

          3. JamesHRH

            Grim baby, I’m a B. Sc. (Math). Math has a lot of parts, but they all model reality for science types.Psychology does not have the same hold on all the parts of the brain that math has on science.Some people call it maturity. Some people call it not being an a$$hole. There a lot of ways to get there without using the words therapy and psychology. I’ve seen colors as a framework for personality, brain quadrant assessments, who hasn’t seen Meyer-Briggs, etc. We won’t even go into the stuff that undermines people’s view of social sciences (regression therapy, etc.). I use the enneagram. Its a good tool. Works for me. Not sure it is part of psychology (is it Jerry?).You are not wrong (you’re never wrong, let’s be clear here, as its not #noeatfriday), but you are not quite right here either.But I can get with Jerry on the bumper sticker – close enough!

          4. ShanaC

            That’s true of all the social sciences though….Econ suffers when correlative becomes causative, for example.

          5. FAKE GRIMLOCK


        2. jerrycolonna

          Exactly James. I often say that the essence of emotional intelligence is a combination of self-awareness and empathy (and it can be argued that true empathy–as opposed to sympathy–is based on self-connection, self-understanding).Radical, non-narcissistic self-inquiry is a powerful tool (and something else available mostly to human brains).

      2. ShanaC

        I like the idea of “does it work?”  Both may work, it seems the focus on the present may be the most useful distiguisher (though not completely, a happy person could seek therapy as a replacement for coaching for some life situation, like having a baby….)

  24. ShanaC

    Also – I found it to be very true about keeping your eyes on the path and the goal at the same time, as well as your comments about balance.

  25. Donna Brewington White

    Very inspiring interview.  I am already an ardent fan of CEO coaching based on the vantage point provided by my work in executive search.  I have witnessed numerous situations in which it could have possibly made the difference in a company’s excellence vs. mediocrity or even its success or failure. (Not to mention the well-being of the CEO.)I even wonder if CEO coaching should be a requirement by VCs and PEs for funding?  Was grateful to hear @jerrycolonna:disqus affirm that people outside of the top roles could benefit from coaching.  The fact that he pretty much nailed me during this interview reinforces that I would be a good candidate.  Besides, sometimes I wonder if this may be a career direction I move in some day.  Another way to exercise the deep empathy with founders/CEOs that is currently a driving force in my work.  But I do believe in “Physician, heal thyself.”  which Jerry models so well and this makes him even more believable.I can understand why Fred is a fan, Jerry. You are amazing!

    1. jerrycolonna

      Donna, what a breathtakingly lovely response. Thank you. Two core reactions:the first is thank you. Yes, I do try to heal thyself as much as I help others heal themselves. Yes. I’m open and clear and direct about my challenges in part because I think it gives permission for others to speak about their challenges.Second, the world needs more of “us” folks so when you’re ready, explore the work of coaching. It’s such a mutual gift.

  26. Robert Thuston

    “If you are going to work your ass off for two weeks, then let your family and friends know you are going to do that, and if you are still missing after two weeks tell them to come find you.”  Great quote.  Tina Seelig (ED Stanford Entr Center) once gave a great perspective on how work-life balance doesn’t exist (as you mention)… except in the long term (it can’t be done short term successfully).  She went on to say that sometimes when you miss something, you can just catch it before it hits the ground (that’s balance).

    1. jerrycolonna

      Thanks Robert. And I LOVE Tina’s metaphor.

  27. panterosa,

    I have worked with Jerry over the course of 3 years. It has added incredible dimension and intention to my journey. Not sure anyone else could have had such an incredible impact.Besides the quantum question of the path or the goal, and can you see both at once, I am struck by the role model for your 5 year old test. My goal is to give my 10 year old a view of passion in work which feeds your soul, and to control the craziness of the work life balance in pursuing that. I drew a graphic of the three 1/3’s when Jerry posted it. I’d like to animate it to show it in motion, and I constantly refer to the graphic to realign. The good news is that my kid knows I am in good hands in trying to sort this balance out – her hero list includes Jerry. She really gets what he does since she sees his work through me in action, and considers that his work is of the higher calling. Not sure how she’d look as Jerry for Halloween though….

  28. William Mougayar

    I watched this during an “other” 1/3 & picked up lots of self-actualization tidbits that made a lot of sense.Jerry- I wonder how do you go from the general to the specific when personalizing a coaching program for an individual?

    1. jerrycolonna

      Mostly over time. That is, working regularly—frequently at first for example–allows both coach and client to develop that deeper awareness which then leads the insights necessary for real growth and change.But the sort answer is lots of one on one conversations.

      1. William Mougayar

        Thanks..So it is a bit like Therapy, but with action and follow-up.

  29. Dave Pinsen


  30. rohandey


  31. Alex Murphy

    “Great ideas come when the mind is quite.”The thing that makes humans Human is the ability to think about our thinking.There was a TED talk about the willingness to fail in the US, that in essence the US economy is on a much faster evolution cycle because companies fail faster and the people involved learn and adapt for the next time, the net result is that the collective economy moves faster. 

    1. fredwilson

      ooh. i like that bit about what makes humans human. nice

    2. jerrycolonna

      Thinking about thinking. Worrying about the future. Ruminating on the past. Worrying about ruminating. Ruminating about worrying. All are part of making us human. 🙂

  32. Jan Schultink

    Too many people call themselves “CEO coach”. It is the specific individual that matters. This post should be renamed: “What Jerry Colonna does”.

    1. jerrycolonna

      Well thanks Jan. I do think that, as Mike Myatt pointed out in the blog post he linked to in his comment on this, the experiences your bring into the client session do make a difference. It took me a while to learn that I would do best to simply be me first, and coach second.It took me a while, too, when I was a VC to learn to be me first and a VC second. And, when I relaxed and did that, I was a better investor.Hmmm…there may be a pattern here.

  33. Mike Myatt

    Jerry, I enjoyed your video and listening to some of your insights. I happen to make my living advising chief executives and boards, but also find myself not so enamored with the profession of coaching. I authored a bit of a rant on this topic which you might find of interest: http://www.n2growth.com/blo… Thanks Jerry…

    1. jerrycolonna

      You’re welcome Mike. I clicked through to your blog post. It’s terrific. Really enjoyed the many of the other pieces you wrote. Thanks for sharing it.

      1. Mike Myatt

        Thanks Jerry – glad you enjoyed the reading. Feel free to stop by anytime.Best,Mike

  34. Cameron

    Great post – thanks -I’m actually more of a paid mentor than coach.  I mentor/coach the CEOs of Media Temple, iContact, and 8 others outside of the tech space. I think there needs to be a lot more clarity when people say they are a coach.  From where I sit, entrepreneurs don’t like the Socratic method of coaching at all – they hate being asked tons of questions, and they’d rather receive some focused mentoring / specific advice tied to what they are working on.

  35. Eliza

    Great interview — thanks for the “1/3rd rule”, I think we all need to repeat this to ourselves.I read again and again American entrepreneurs and in general people who understand the start-up scene comparing Berlin (and I think Europe in general) with the spirit of New York of the 90ies…it hurts to hear Europe is 20 years behind, although I am sure they are right. Any chance we can catch up anytime soon? I guess the lack of failure acceptance will hinder us for at least more 20 years to come….

  36. Stephen Baum

    Implied: self-discovery is crucial — coaches are not consultants. And homework must include “field experiments” with a physical component as well as “thought experiments.”  

  37. Rohan

    A little late.. but thanks for sharing this Fred. And I also found this – http://www.youtube.com/watc….. Was very nice to see! 

    1. fredwilson

      a mutual fan club 🙂

      1. Rohan

        My mom calls them MAS – Mutual Admiration Societies. Key to any great relationship I think.. 😀

  38. jerrycolonna

    Thanks for the kind comments. I think we all have a responsibility to see it, name it, and call it out when we see it.