Jerry Colonna's Workshop

At my meeting with Applicake on Monday, Ela mentioned that Jerry Colonna would be giving a workshop in Krakow on Wednesday that had something to do with entrepreneurship and suggested that I go. This seemed like serendipity, so I did.

Jerry was previously a venture capitalist (VC) so I assumed this would be about seed money, rounds, valuations and things like that which I have mostly avoided in the past. Adrian didn't want to come because he said he "didn't like VCs," which is understandable because you mostly hear terrible stories about how they give you a little money and then pirate your company out from under you, things like that. After studying the topic more I've learned that, while bad things have certainly happened it doesn't have to be that way and if you find the right VC it can be a very good relationship. So people say, anyway.

It surprised me when Jerry's workshop ("Surviving the Startup") turned out to be more like something I might have found at Esalen. The main theme is how to start a company without destroying yourself, and it focused on the personal struggles that people have in startup companies. Even the part at the end, which was people practicing their VC pitches (hearing that this would happen made me think the whole thing would be all hardcore nuts and bolts) was oriented towards personal experience and connection.

The seminar was held in a room that had a glass ceiling so you could see the sky. A very nice effect, and not something I've ever experienced in the US. We signed up for lunch ahead of time; I was feeling over-meated so I chose the vegetarian option, and ended up with a salad; not with things in it, but basically a pile of lettuce. At that moment I realized that I had been warned about this: "vegetarian" seems to mean "salad" in Poland. So, some tummy rumblings later on.

One of the most important slides summarized all the emotional difficulties of starting a business:

• The financing roller coaster
• Loneliness ("Oh hard condition, we must bear all" -- Shakespeare, Henry V)
• Investors and board members (Seagull management where they fly in, drop a bomb and fly away)
• Managing people
• "The Crucible" (Your internal process and struggle which is different for everyone)

Looking at these, only the last one cannot be mitigated in some way. That is, I believe that by changing the structure or by adding supports we could relieve the other issues so that you could go through your own crucible without the extra pressure from the other factors -- and thus produce many more successful startups. (As always, this belief is an act of faith and I have not yet discovered what these structures and supports might be).

I often find that I get the best insights from what I call the "side stories," things that aren't necessarily an intentional part of whatever experience I'm having. In this case, one of these insights came from Jerry's structure. He talked for maybe 1.5 hours (with a break) before lunch, then after lunch he only talked a bit more and opened it up for quite an extended question-and-answer period (and even during the lecture part he seemed to be trying to extemporize and bring in the audience). The Q&A might have even gone as long as the lecture period. It definitely helped break up the pattern of "too much talking" that many speakers tend to fall into (including myself, in the early years).

At the end was a practice pitch session, where people from the audience who had been working on projects they hope to turn into startups try out their one-minute pitches to give to potential investors (hearing about this had originally made me think that the whole day would be all about nuts-and-bolts VC fundraising). The ideal pitch should be roughly structured like this:

• The problem we are solving, and why it's a problem
• Our solution
• Why we are the team to do it
• How much we are raising

The goal of the pitch is not to get the money (which no one is going to give you after one minute, anyway) but to get another meeting.

People were understandably nervous about doing this, but the feel of it was not "hard" at all, but instead Jerry tried to make it supportive and helpful and work with people's feelings and in general reduce the level of anxiety around making a pitch. Much of it just had to do with restructuring the pitch so it became clearer and more direct (for example, because people were typically technical, they often wanted to include technical details which didn't contribute value to the pitch).

As often happens, seeing the different structure that Jerry used made me realize that I've been overly rigid in my own thinking about events. I've gone from pure speaking, eyes-forward events to purely open-spaces style events. But he mixed it up a little, and that has made me think that, if interest develops, I could create a "Reinventing Business Day" that would look like this:

• My evolving "Reinventing Business" presentation, about 1.5 hours
• A Q&A period
• Several open-spaces sessions
• Finally, lightning talks from attendees describing what they are working on

This one-day event wouldn't preclude longer events, but it could be optimal in many situations because often people can justify taking a day more easily than taking several days (or the first day could be the foundation, and further days could be chosen by those with the time and inclination).

The goal would not just be to introduce the project, but more importantly to help form a community in that place. I find that when people see how easy it is to create an open-spaces event, they start doing them on their own (the open spaces after Geecon not only added that day for future conferences, but several people said they plan to start doing them in their cities). The lightning talks are a way for people to learn what others are doing and that tends to start conversations, and possibly even alliances.

For me, the Reinventing Business Day would be a way to get me to different places and in touch with evolving companies that I could then visit once I'm in the area. As I've started visiting companies I've discovered the impact of actually seeing things in action (again, very often because of the "side stories" effect), so more of this is clearly necessary. Books and blogs and podcast lectures have been exceptionally useful, but direct experience cannot be matched. Ideally we'll be able to figure out reasonable fundraising approaches (probably fees and sponsorships) to be able to not only cover costs but to further support the Reinventing Business project.

Books suggested by Jerry:

• Let your life speak
• Let My People Go Surfing
• Venture Deals
• The Lean Startup
• Biographies of Vanderbilt, Rockefeller, Jobs
• You can follow Jerry on Kindle
• He also suggests Chad Dickerson's blog entry on Etsy's financing

Quotes and ideas that I liked from the day:

• "I think I'll be myself today. Everyone else seems to be taken."
• Create a user manual for yourself (what someone else can do when you go astray or get strange)
• Use rituals to contain the day
• Create "accountability groups" to keep yourself on track
• Meet the client where they are (something I've long believed)
• If you're not standing on the edge you're taking up too much space

During the Q&A session the "hiring good people" topic came up, so I asked for better ways to do this. He suggested things which turned it around and challenged the interviewee in a different way:

• Ask the interviewee to create a job description
• Ask the interviewee to create a "user manual" for themselves in that job ("if I do this, you should respond by ... And if I do one of these things, you should fire me.")
• Ask "What are the first three things you'll do in the first two months you're here?"

A couple of months ago I was trying to figure out more revealing ways of interviewing, but unconstrained by the industrial management structure. I thought it would be interesting if the interviewee were to define their own job. If they were filling a previous job where a person had created a job definition, they would start with that and refine it as they learn about the job; the job definition becomes an iterative process based on experience. I think Jerry's first question, in the more traditional context, is a kind of a test to see whether the person paid attention to the published job description but still it's an interesting basic principle: instead of asking canned questions, put the ball in the interviewee's court and see what they think the job is/should be.