The Reboot Podcast

A few weeks ago Jerry Colonna and I got on Skype and had a 40min chat about startups and what goes on in them. As most of you know, Jerry and I started a venture capital business together in the mid 90s and have been close friends since then. So this is a public conversation between friends, which is usually a recipe for a good discussion.

The first five minutes is some stuff about Jerry’s new business, It’s worth listening to, but if you want to skip it, click on the soundwave at 5mins in and you will get to the start of our conversation.

#entrepreneurship#VC & Technology

Comments (Archived):

  1. pointsnfigures

    Ironic. I found this last night on Soundcloud and blogged about the same podcast today. I think that so many people in the entrepreneurial community are not “real”. What I mean is there is an ethic of “fake it till you make it”-and on the investor side, instead of having tough conversations-or instead of just rejecting entrepreneurs, they deflect using obtuse language.When someone like me that doesn’t hide behind language comes into the picture, they don’t believe me. But, when I meet someone like that it’s refreshing. I guess it sort of the reason I come to this blog.I look forward to listening to Jerry’s whole series. A friend of mine in Chicago, Raman Chadha is doing something similar with The Junto Institute.

    1. LE

      Fake it till you make it works [1] because of what I call the “assumption of legitimacy”. Same “assumption of legitimacy” allowed me to start perhaps 3 businesses that I knew nothing about and be taken seriously as if I knew something right from the start. Nobody asked any questions at all. Imagine going up against Xerox with all their experience (and salesman in suits) and actually getting the contract instead of them (and it was 250k in early 80’s dollars). Didn’t lie either. Need to point that out. Just was never asked anything that I couldn’t answer truthfully. It all worked out kept the contract for 6 years (until the hospital system went belly up). [2]Ditto for some PR stunts that I did. Nobody ever asked any real questions if they did they would have flushed out enough info to know what was probably going on. (Of course there is always a shred of truth so it’s not like it’s that easy.)One of the reasons I ask so many questions and that I am so cynical. Because I know that other people aren’t. Not unusual at all for people to say to me “wow I’ve never been asked that before”.[1] One of those concepts that probably confounds the asperger crowd since you can’t really pin your hopes on something so nuanced that isn’t easily defined in a digital way.[2] If you aren’t smart enough to say and do the right things, be confident, and make the correct decisions you won’t be able to last faking it for very long. So the system is self selecting. It takes a certain amount of drive and intelligence to even go down this road and pull it off.

      1. Joe Cardillo

        Fake it til you make it is also carries potential risk of causing depression, isolation, and a split from reality (the Reboot episode w/Rand Fishkin is great, as is this recent post:

    2. bsoist

      I made a note to catch this podcast a short time ago ( I think Brad Feld linked to an episode ). I listened to the first two episodes over the weekend and thought it was great stuff. In episode one, they dove into some fairly deep stuff right away. I have episode three queued up for later today.RE: fake it till you make itI will never forget the first time I heard that phrase. I was a pre-teen or early teen and a classmate of mine said he learned that from his father. Since his father was our pastor, that really churned my stomach, but I did learn later that it can be a legitimate strategy as long as it’s not just an excuse for dishonesty.It’s unfortunate that some have taken an idea that might make sense in context, and carried it too far. Fake it till you make it, as I learned it, doesn’t mean pretending to be something you’re not or conning people.

  2. JimHirshfield

    “You don’t know jack shit about the business” Hahahaha. Love it.

  3. JimHirshfield

    “Managing up is a complete and total waste of time” – F.Wilsonre: CEOs managing their board and investors.

    1. Matt A. Myers

      “… take your seat. It’s your life. It’s your job. Do that.” – J. Colonna

  4. JimHirshfield

    I like Jerry. So Zen Mastery.

    1. pointsnfigures

      Me too.

    2. jerrycolonna

      I like him too.

      1. JimHirshfield

        Relieved to hear it.

  5. John Revay

    I did not realize that Jerry had morphed / re branded his coaching biz….I did know that he was doing the boot camps out in CO…..I checked out his site this AM, it had some great content that I will go back to and consume…

    1. jerrycolonna

      Thanks. The morphing began officially over the summer.

  6. Twain Twain

    Thanks for sharing. The best part was about Jonathan Levy and Ron Schreiber. Theirs is a masterclass for founders to get investors to gain a direct, proactive, hands-on FEELING about their business and establishing the relationship onto a more pragmatic and trusting rather than theoretical and detached footing.Some investors read the PPM, do cursory due diligence, wire the money and then just rest on their laurels to earn mgmt fees from the LPs. Likewise, some founders pitch via a slick video, do cursory due diligence, take the money and start burning it and then just rest on their laurels believing they can always raise more money.Meanwhile, other investors and founders actually engage each other to be proactive, educate+learn+improve, eat and share the dog food, make tough decisions and DO everything possible to make the product(s) and company a success.

    1. Matt A. Myers

      I overheard a conversation the other day on public transit of two enthusiastic business students who had a meeting to pitch something to an investor. From what they were wanting to highlight, to me I was thinking there was no real substance to what they were sharing; it didn’t sound like they had a product yet to be able to show proof of concept or traction. From my time around business students, for whatever reason many of them seem to have unrealistic expectations – maybe we all do until we get run into the ground and learn to push ourselves back up from the gravity of the scenario.

      1. JimHirshfield

        Realistic expectations never deliver surprising results.

        1. Twain Twain

          Only the audacious and brave, who don’t know they’re supposed to follow the rules and do the same things like everyone else, change the world.

          1. JimHirshfield


        2. LE

          First let me compliment you on a great saying. (Really it’s Fake Grimlock quality).Now let me “opine” that that’s one of those aphorism’s that is formed solely from observation of success and not those that have fallen flat on their face.Reminds me of that Springsteen live concert where he talks about how his father wanted him to be a lawyer and stop playing guitar. And everyone cheers like “wow how fucked up!!!”. And then some 17 year old chick in the audience cheers him on even more (you can hear her) as in “good that you didn’t listen to your dad what an idiot he is”. Never listen to parents. What do they know? Meanwhile the other guys who are playing guitar that didn’t become lawyers (this was back when that was actually a good career not like now) are in the factory making your pancake batter.

          1. Matt A. Myers


          2. JimHirshfield


          3. JimHirshfield

            Thanks for the fake compliment. I mean the Fake Grimlock compliment.As for your second paragraph, not sure if that’s a ding or what.

          4. LE

            The compliment is toward you for a great saying (sentence one).The “ding” is for people who believe such aphorisms.Same people that buy into being called a hero for risking their life (for a complete stranger) without considering the effect on their own family by taking such a risk. Like I’m glad my dad was around for a long time and didn’t jump down on the train tracks and all of that to save a stranger and be called “a hero”.And in contrast to what I said in the above paragraph it always amazes me how people cheer and egg other people on to take chances when they themselves have no skin in the game at all.

      2. Twain Twain

        Haha, Matt. I was going to comment on the super-ambitious, super-confident “Young Turk” business types who are off the conveyor belt of the Ivy League/Russell19 schools, have limited experience at the coal-face but have read plenty of neat little case study models of how companies “should work” and then proceed to TELL/ORDER the CEOs on how to make decisions and run businesses when the YT may literally know zip about the realities of making products and successful businesses.It’s not just investor-types, it’s management consultants in their mid-20s who haven’t got practical experience to back up their theories and neat little slides.When Fred said he was really ambitious in his mid-20s I found myself nodding in recognition. That was me too.Today, people send mid-20s “Young Turks” my way so I can help them interview those YTs. I’m a decade on and have a reasonable gauge on where YTs are coming from and where they want to go.The difference between me as a “Young Turk” and other YTs I meet nowadays is that I spent 4 years of my teens at the coal-face in the chemical industry making products for global scale, followed by a few years in startups BEFORE I joined the Strategic Investments team at UBS and then got promoted into CEO-Chairman’s Office to do corporate strategy.After that, I worked for a year as a VC. That was an independent boutique so I had a frame of reference when Fred talked about how it’s a form of entrepreneurship too and carries risk.There’s nothing wrong with “Young Turk” business students per se.Just that I know from personal experience that the knowhow gained from hands-on practical experience in a business, at the coal-front, is very different from the genteel abstract theories of business school and institutional investment.

        1. Matt A. Myers

          It reminds me of how in highschool, Grade 10 or 11 business class, the teacher told us – first stating that he could probably get fired for telling us this – that if we have good ideas, know we have good ideas, then to not go to university and go into $40k debt (Canada) but instead spend 4 years working on a business to learn what we need; in the end we’d have 4 years of experience on top of those who went to school, and we’d not have $40k debt but perhaps actually be earning a sustainable income. This resonated with me a lot, though I still was under pressure from parents, one who’s a professor in academia, and both who are highly educated.Luckily my parents are finally understanding and accepting of my path that doesn’t provide me a piece of paper saying I know what I am doing – though whatever paper you get when you IPO would be a neat graduation-like thing to get someday.

          1. Rick

            A person educated only in a school isn’t educated at all..A small amount of actionable knowledge is infinitely more valuable than a large amount of inactionable knowledge.

  7. JimHirshfield

    Feels like Saturday around here. Where are my banana pancakes to go with this Video of the Week?

    1. Matt A. Myers

      I thought you were making them for us all? No?

      1. JimHirshfield

        Nope. But many of my jokes flop like flapjacks.

        1. Matt A. Myers

          Sometimes they’re a bit too saucey.

          1. JimHirshfield

            Likely you meant syrupy. But I appreciate you playing along.

          2. pointsnfigures

            you might need to put some more baking powder in them so they are lighter and rise a bit more

          3. JimHirshfield

            I prefer to boost the whole wheat flour. The higher fiber content delivers a more moving experience.

          4. LE

            Nobody has better transit than I do.

          5. JimHirshfield

            Braggin’ ’bout your chunnel? Please don’t go there.

          6. JimHirshfield

            Jerry: “French impressionist paintings?”George: “I find the soothing pastoral images very conducive…”Jerry: “–ThankYou”

          7. Kirsten Lambertsen


  8. Matt A. Myers

    Just reminded me of a show I used to watch, early teenage years … Tron-like idea.

  9. reece

    great conversation…nice to hear the stories and examples that have led you guys to your approach in investing

  10. Matt A. Myers

    Really cool to hear about the very start of Geocities.I was at Bruce Croxon’s Entrepreneurs 101 talk last week – Bruce being one of the founders of Lavalife. He shared how Lavalife started, and it was another great story to hear; video found at the bottom of

  11. Kirsten Lambertsen

    It’s all about the Zen, baby.

  12. William Mougayar

    Wow, you do open up more than ever with Jerry. And the insights are equal from both of you. Different dynamic than with Brad.

    1. jerrycolonna

      I know how to make Fred cry.

      1. William Mougayar

        Oy…That’s powerful.

        1. jerrycolonna

          With great power comes great responsibility. I use my powers carefully.

  13. ed

    Can you put this on youtube? Soundcloud is just horrible.

  14. Rick

    That was well scripted Fred. Next time you should pretend that someone knocked on your office door while taping. They could mention polly-wally-mulligan detergent or whatever. You know. Kinda’ like that old radio show Prairie Companion or something..The world wide web of deceit has become so lame and boring that having an internet connection is becoming basically useless. But that was some good clean entertainment. Thanks Fred.

    1. Underwhelmed

      Sounds lke your soul needs a colonic cleansing. Its depths must be fouler than 3 day old sewage for you to be trolling this a convo between friends.

      1. Rick


  15. Alex Wolf

    Ambition + doing what you love = scary.Scary to love so deeply, be so invested.@jerrycolonna:disqus If attachment is the root of all suffering, then we are doomed from the start by our passions? Yet we chase them more fiercely every day. #dilemma for the coach.

  16. Steven Kane

    What a treat! 🙂