I Went to Prison for Good

On March 26th, 2019 I went to the California Correctional Institute, a supermax state prison north of Los Angeles.  I was there for cause – a good cause.  I was volunteering as part of a “Prison Entrepreneurship Program” that is an employment, entrepreneurship, and personal development training program that helps the incarcerated and formerly incarcerated to become successful, legal entrepreneurs and employees.  The program has been around for over 15 years with at least three different organizations in different parts of the country operating.  Graduates have an exceptionally low 7.5% three-year recidivism rate (compared to the national average of nearly 50%).

I was there for the entire day with about 50 other business leaders in a room with 65 inmates, or “Mavericks” as the program calls them.  In order to attend the event, the Mavericks had to apply to the program and complete all the coursework and attend all the classes.  Nobody who applies is turned down, but they must do the work in order to continue through the program.

Because I was just there for a single day I don’t know what all is involved in the coursework, but the Mavericks had spent months preparing for the day by learning interpersonal skills, public speaking, basic business concepts, writing a resume, doing practice job interviews, creating a business plan, writing their life story, and learning how to approach everything and everyone with a positive attitude and energy.

Continue reading “I Went to Prison for Good”

Why my Jeep needs to be in the Blockchain

Today I attended “Day For Crypto” in Cincinnati. It was an event focused on blockchain technology, cryptocurrencies like Bitcoin, and startups involved in Initial Coin Offerings (ICOs). There was a lot of interesting speakers from all over the world discussing the many ways blockchain technology can be used in business. I heard many speakers describe how blockchain is going to change or even disrupt different industries, but the most compelling reason for me personally came after the event was over.

Continue reading “Why my Jeep needs to be in the Blockchain”

I was a DEF CON Virgin

Last week I got to experience the DEF CON hacker’s conference in Las Vegas for the first time.  If you aren’t familiar with the conference, it is one of the world’s largest hacker conventions, and this year was its 25th annual convention.  DEF CON is considered an “underground” event because it is community driven and doesn’t have any major corporate sponsors, yet it attracts roughly 30,000 people such as computer security professionals, journalists, lawyers, federal government employees, security researchers, and students from all over the world.  You can read more about the event here:



I’ve attended over a hundred IT focused conferences in my life, but for some reason DEF CON never made my list.  I don’t know why I hadn’t attended before – I guess I never really “got” the community.  But this past year I read “Ghost in the Wires” by Kevin Mitnick and gained a much better understanding of what makes this community unique, so I decided to add DEF CON to my list. Continue reading “I was a DEF CON Virgin”

Tracking Holacracy Work Items in GlassFrog

In a couple Holacracy meetings last week there were some questions about where to keep track of what everyone should be doing, so I thought I would share a portion of an e-mail I sent out to our team explaining how we should be tracking our individual tasks.

Basically, there are 4 different types of activities in Holacracy, and only two of those are actually tracked within the GlassFrog application, which is why there is some confusion.  It breaks down like this: Continue reading “Tracking Holacracy Work Items in GlassFrog”

Holacracy Meeting Fatigue

At this point we are almost two months into our rollout of Holacracy across our entire organization.  About 75% of our employees have at least one role assigned to them and are attending at least one circle meeting.  There are a few employees, me included, that are in multiple circles and therefore have many meetings to attend.  Currently I’m in three circles, so I have six hours of meetings scheduled per week.  That’s a tactical meeting and a governance meeting for each circle. Continue reading “Holacracy Meeting Fatigue”

Our First Holacracy Tactical Meeting

We are about a month and a half into our implementation of Holacracy and this past week we had our first Holacracy Tactical meeting.  Because the governance meeting is a core requirement of Holacracy it almost goes without saying that we’ve been having governance meetings since we rolled out Holacracy.  The Holacracy tactical meeting, on the other hand, is an optional meeting.  After having just one tactical meeting in my company I can see how valuable they are and it will be something we will be implementing throughout our entire organization.

Put simply, the governance meeting is for working ON the business, whereas the tactical meeting is for working IN the business.  The governance meeting is the only way for employees to propose changes to the structure of the company and for those proposals to be accepted and incorporated into the company’s governance documentation.  Without that process, there is no approved way for anyone to make any changes, so it is paramount that those meetings be held.

In a Holacracy organization, to communicate and get work done, employees don’t necessarily need to use the Holacracy tactical meeting. If a company has a current tactical meeting system they are using that is working, then by all means, they should continue to use it.  That is not the case with us.  We, like many companies, haven’t been holding the most efficient tactical meetings.  The meetings haven’t been time-efficient or structured and the output of the meetings hasn’t always been captured very well.

Like everything in Holacracy, the tactical meeting is very structured and well-documented.  It creates accountability by reviewing a check list and metric list each meeting, and capturing action items and projects in the meeting minutes that are distributed to everyone, even those that miss the meeting.  All the items are tied to roles and/or circles in Holacracy, so it just dovetails perfectly with governance.  In fact, when you assign a task to a person instead of a role it highlights it in red to remind you that you should probably have a role that is responsible for that work, not a person.

We currently have three circles that have been created, and only our Operations Circle is using the Holacracy tactical meeting.  This coming week our General Company Circle will start as well.

An Awkward Holacracy Meeting

We’re about month into implementing Holacracy here at Intrust IT, and today we had our first awkward governance meeting. The good news is we learned our lesson so it doesn’t happen again to us, and hopefully after reading this it won’t happen to you, either.  What made it awkward was halfway through processing our tension list, one of the tensions resulted in creating a new Operations Circle.  The creation of the circle wasn’t necessarily the awkward part, it was what happened right after that. Continue reading “An Awkward Holacracy Meeting”

Missing a Holacracy Meeting

Today I missed my first Holacracy governance meeting due to a board meeting I was required to attend.  Being the company champion of Holacracy I worried a bit that without me present the meeting wouldn’t happen, or worse yet something would happen in the meeting to cause everyone to become disenfranchised with Holacracy.  I think it’s a common fear that entrepreneurs have about anything they are involved with, and common among parents leaving their kids somewhere for the first time.  We all imagine the worst.


Anyway, I was very happy to find out that it was quite the opposite.  The meeting happened right on schedule, and afterwards I received an e-mail from Glassfrog reporting that five new roles had been created and one existing role had been modified.  I spoke to our facilitator and he said it was a great meeting and that everyone is starting to get into the flow and understand and appreciate the process.  Continue reading “Missing a Holacracy Meeting”

Assigning a Role to a Person in Holacracy

After a role has been created in a governance meeting, then that role needs to be assigned to someone.  By default, all unassigned roles are the responsibility of the Lead Link until they are assigned to someone else, which is handled by the Lead Link.  It’s in the Lead Link’s best interest to assign a role to someone else as soon as possible, especially in the early phases of an implementation of Holacracy because a lot of new roles are created.

Today I got to assign my first role to someone.  Continue reading “Assigning a Role to a Person in Holacracy”