Chief Shit Disturber

My friend Howard Gwin (LinkedIn) has said the perfect role for me would be one of “Chief Shit Disturber”.

“an individual who creates unnecessary conflict and unhappiness where it is especially not required” –ย Urban Dictionary

I’m not sure that this is quite what Howard intended. But that I live in the creative tension between product, marketing, development, customers and growth. It’s a chaotic place where the demands change instantaneously and often change due to forces unrelated to the company or the team. (Or at least that is what I hope Howard means, and not that he thinks I stir up trouble unnecessarily.)

I have often thought that the perfect role for me would be one like James Higa, who Steve Jobs picked as “his right hand man”.

“One was an ability to be frank, honest, and able to go toe-to-toe with him on any question. The other was wide peripheral vision. Heโ€™s always wanted that in the people around him. The ability to connect dots is really important. Aย Renaissance perspective on the world. Because it was always about the intersection of technology and liberal arts. BusinessInsider

Not to say, I won’t do the founder thing again. Founding Influitive was exciting/fun/stressful. Leaving wasn’t easy, but it was the right thing to do for me, for my cofounder and for the company. It gave Mark the room he needed to operate more effectively. I have enjoyed going toe-to-toe with Mark on everything from product design, to customer acquisition, to fundraising, to hiring, to company culture. I think Mark appreciated the candor and insight, as he has a Chief of Staff role that sounds strangely familiar to me.

But it has me on a new career path. I am back in a world as a consultant. I’m not sure that this consulting thing is going to be a permanent thing (see Teehan+Lax: A Happy Accident), but I will try it, at least part-time. I am spending part of time at OMERS Ventures, where I get to see how the sausage is made. But I’m trying to figure out what to do with the rest of my time.

I have worked with startups for a very long time. Some have been successful. Some haven’t. But I know I add value. The challenge with early-stage companies (pre-Series A) is that they can’t afford to pay me (for more reasons why this is important). I am looking for models that work and don’t work for a consulting practice. Yes, yes beware the consultant. And consulting math versus software math. And you can read my thoughts on being/using a funding broker, ain’t happening.

It would be easy to pay for bits or bit development. But we’re talking advice. Kind of like a lawyer. I can’t figure out how to make this work. Any thoughts?


7 thoughts on “Chief Shit Disturber”

  1. David,

    A couple of quick thoughts:

    Consulting to start-ups is a tough business. They usually don’t have the money to pay a market rate. Compensation based on outcomes is hard, since how are those outcomes measured? If you are selling advice, like a lawyer, and maybe aiding in the implementation of that advice, then the client should have no problem with paying for that advice. They don’t stiff their lawyers. If the client does not want to pay, then they have not seen the value in the advice you are providing.

    As for the role of a funding broker, how do you capitalize on the network of investors (people, groups etc.) that you have built over-time and the mutual trust? Rather than charging a commission / fee based on the funds received, maybe if you have some capital, be part of the investment round?


    1. Agreed on all points.

      I think the challenge is that over the years I have focused on helping early stage, pre-product/market fit companies with a variety of things. And that this market is a terrible market unless you are a founder of these companies. It’s part of the reason that I decided to join OMERS Ventures. An opportunity to change the game I am playing, i.e., to see later stage companies.

      My fear is that for a lot of founders, it’s scary/difficult to have a guy like me helping/calling bullshit and engaged. I should ask Mark Organ or Marc Castel. Because I can be relentless. Maybe I need to change.

      1. No, you don’t need to change ๐Ÿ™‚ Focusing all of that intent on just one company is a little relentless — and there is the balance of letting them learn to run their own business.

        Too many engagements at once can be draining.

        There is something about being a funding broker. Except broker is not the right word. Some of the old school programs have names like “Investor Ready”. If they can get past the fire breathing David Crow, a company is investment ready. And many would be happy to pay to go to that kind of boot camp.

        We have to kill pay-to-pitch, but someone still has to prep companies on one side, curate them in the middle, and bring the check writers to the table on the other. I’m convinced we need to burn down the non-existent networks that exist around this now (at least, those that are pay-to-pitch) and create new ones.

        1. The part that concerns me is how much the access relies on personal reputation and not necessarily the quality of the company/idea/pitch. Not that is fair in love and war (or fundraising), the educational practice for most founders is pretty straightforward, i.e., winning is 90% preparation and 10% execution (maybe 5% tiger blood). I have often thought that this is the benefit of an incubator. Look at the YCombinator folks, it was the pedigree and the editing along with the extremely selective input process that guaranteed better output.

          The second concern is the “fire breathing”, sounds too much like a Dragon or possibly a Shark ๐Ÿ˜‰

          I think there are some basic economics that change with scale, i.e., capital allows you to “invest” in these companies and take a larger percentage. I’m wonder how @seanellis charged before Qualaroo. I should ask.

  2. Another approach is to offer some of this help for “free”. Offer the help, have them pay you what they think it is worth, in whatever currency makes the most sense for them – equity, cash, etc. If you don’t need the money in the short term, this may be a good way to build some currency with people who will recommend you. When you settle on the “right” way to be compensated, you’ll have a list of referrals to back up your value.

    Yet another way is to offer the advice, and let it lead you to investments. There are a few folks who appear to do that in Austin. This assumes you have enough $ to be involved in angel investing I suppose… But it is definitely an interesting way to see more companies and pattern match and challenge them.

    Thanks for the cross-link, btw. Wondered why I was suddenly getting traffic from the chief shit distributor ๐Ÿ™‚ er, Disturber ๐Ÿ™‚

    Good luck, David!

    1. @sfrancis:disqus unfortunately, I am able to make some investments, i.e., according to my AngelList profile I target 2-3 investments/year @ $10k each.

      I haven’t seriously done the consulting game since I lived in Austin. Part of the challenge is that my offering has changed in the past >10 years. I’m not longer the most effective bit pusher. I think revisiting the product/offering and trying to iterate along with the perceived value.

      1. is that fortunately or unfortunately? ๐Ÿ™‚ I think it isn’t about necessarily bigger stake, just puts some skin in the game – which some startups will really appreciate. depends on the relationship, i suppose ๐Ÿ™‚

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