Saying Goodbye to CoconutHeadsets

Posted on September 16, 2015
Filed Under Critical Thinking | Leave a Comment

I like new beginnings, so, it is time to put this blog to rest and begin again.

In 2003 I started blogging at Businesspundit. It was a great experience and I met a lot of great early bloggers because of it. While I was at it, I started one of the first crowdsourced businesses, which you can read about here. It crashed and burned, but, that’s part of the process. I sold Businesspundit in 2008 and moved to this site.

I chose the name Coconut Headsets to reflect on the cargo cult types of experiences I was seeing in the business world. But, while blogging here over the last 7 years, I was building a business, Backupify. That probably explains why in 5 years at Businesspundit I wrote over 3700 posts, and in 7 years at Coconut Headsets I wrote 62 posts.

I will keep this site up, because there are some good old posts that still get a bit of traffic. But I won’t write here any more. Going forward, I’m putting all my industry stuff, particularly writing related to Machine Learning and Machine Intelligence, on Technically Sentient. There is also a newsletter I send out from that site that is a curated set of links, not just my posts, so you should sign up. For anything that doesn’t fit that site, I plan to post that on Medium. You can follow me here .

Introducing Technically Sentient - A Newsletter on the Tech and Business of A.I.

Posted on July 13, 2015
Filed Under About | Leave a Comment

The short version is, I have started a newsletter than you don’t want to miss. Go here to sign up.

Now for the longer explanation…

Back in 2002 I started work on a graduate degree in Computer Science, with a focus on Artificial Intelligence. I stopped after 18 months because I didn’t agree with the underlying philosophy of how they taught A.I. It was all top down, command and control stuff, at a time when bottoms up emergent models were just starting to show promise. But for the past 13 years, I have continued to follow the space, read papers, watch companies, etc.

Now that I’ve sold Backupify and have some time, I decided to make A.I. the primary focus of what I do going forward. I just made my first angel investment in Netra, which brings an interesting machine learning approach to video analytics, and I hope to make 20+ angel investments a year in this space. I think that over the next 2 years I can become one of the top angel investor in this area, and get really great deal flow as a result. I think I am better positioned than most early stage VCs to understand the technical and early market risk of many of these companies. Most importantly, I think over the next 5 years the focus of A.I. will move from “Machine Learning” to “Machine Thinking”, and as more higher level work becomes automated, providers of capital into these spaces will get disproportionate economic gains.

But my interest in A.I. is about a lot more than investing. What I love about the space is two things. First, it is a multidisciplinary space. People come to A.I. from Computer Science, Linguistics, Electrical Engineering, Robotics, Philosophy of Mind, Cognitive Science, Neurobiology, Medicine, Cognitive Psychology, and all the other fields you can get by combining those branches of study (e.g. Computational NeuroLinguistics). That cross disciplinary nature makes it incredibly interesting, because I get to follow advances in all kinds of areas.

The second thing I love about A.I. is that it is filled with all kinds of moral, legal, political, and ethical challenges as it moves forward. Building sentient machines will challenge many of our the underlying philosophies on which modern civilization is built, and as someone who is attracted to complex multi-dimensional problems, I think it will be exciting to help companies work through those.

To make sure I stay focused and move forward, I decided to start an email newsletter called Technically Sentient. It will be sent out a few times a month, but at my leisure, not on a regular schedule. It will focus on interesting businesses I’m seeing in the A.I. space (with some Robotics and Neurotechnology discussion as well - as these are the follow on areas of the intelligence revolution). I will also interview key people in the space, and write my own thoughts as well. I have found that writing often helps me clarify what I actually think about a topic, and I am excited to do more of it.

If you are in this part of the tech industry, go sign up. You won’t regret it. And if you are starting a company in the A.I. space, please send me a summary of it. That is where I want to focus my investing.

If you are raising capital for an early stage company that somehow incorporates artificial intelligence, please reach out to me. If you have cool stuff that you think I should include in my newsletter, send it to tips@technicallysentientdotcom.

Also, go here to sign up for my email newsletter.

Meetings and Communication Structures

Posted on June 14, 2015
Filed Under Business, Critical Thinking | Leave a Comment

The interesting thing about really small companies is that they like to boast about how much better they are than big companies. I did it too. When Backupify was 8 people and we never had any meetings, I talked about how cool we were and how much smarter we were than all those boring big companies with their meetings and structure and process, and how we would never have that crap. But that’s mainly because I was an idiot.

It turns out, big companies usually work the way they do for a reason. Think of it like a basketball team. If you are playing 2 on 2, you don’t need much of a strategy. One guy has the ball and the other moves around. You can run some simple plays like give-and-go, but mostly its improv. As you add players, it gets more complex. Say you were playing basketball with 10 guys on each side. Now there is no room on the court to move, particularly if everyone is running all over the place improvising. You either need to run coordinated plays, or you need to at least have a general philosophy about how the offense should work and where people should move based on what is happening.

The parallel in business is that only way to get big, really, is to master the processes and structures that make it easy for people to know what to do, and to get the context they need for their work.

It’s usually around 15 employees that you start to realize not everyone knows everything that is going on. Prior to that, you all sit around two or three tables all day, close together, and hear everything that everyone says. Around 15 people, for at least a few key hours a week, someone is always out - sick, vacation, travel, whatever. So you realize you need a way to recap all the key points for people. Most companies start having a weekly or monthly “all hands” meeting about this time. The All Hands Meeting becomes important, so people try not to miss it, and its not too hard to find some time every week or two that everyone can make it.

After 15 people, every time you double, you face this same problem. Your communication architecture breaks down again because the channels you use to communicate no longer reach everyone, so you have to add more channels. But, you don’t want to add so much overhead that it slows everything down. I know some companies that at 50+ employees, still meet every single day for a few minutes in the morning. I think that’s tough.

What I want to share in this post is what Backupify looked like at 80 people. There are probably lots of right ways to do this, so don’t take this as gospel, but this structure worked for us, so I am sharing it in case you find it helpful. This doesn’t include every meeting we had, by any means, but instead, is all the key meetings that I drove, or was deeply involved in as CEO.

Keep in mind that we were highly experimental with meeting and communications structures, and every quarter we tried new meetings (some stuck, some didn’t), new formats for existing meetings, and new configurations of attendees. What you read below is just where we were at exit.

1. Weekly Reports
Each executive emailed the group a weekly report. We had no standard format across teams. Everyone developed a format that worked for them. It was supposed to take no more than 10 minutes to put together. It basically tracked the progress of their group that week. Some execs used their quarterly goals, and tracked progress against them. Others were more detailed. These went out between 3pm Friday and 9am Monday. We never had “status” meetings because I think having a meeting just so people can report on status is inefficient. It’s easier to just read it.

2. Weekly Management Meeting
This was a 90 minute meeting that happened every Monday at 1pm. The first 45 minutes were the senior team, and the second 45 minutes alternated each week between either Sales/Marketing or Product/Engineering/Support. Junior executives and key individual contributors joined in the second half of the meeting if it was relevant.

We shared a Google Doc every Monday morning that had the following headings:

- Questions on Weekly Reports: This was anything that an exec wanted to discuss from someone else’s report.

- Customers: This was anything having to do with getting and keeping customers - things that impacted them.

- Product: This was new releases, problems, changes to scope or schedule, etc

- Team: This covered new hires, demotivated team members, HR issues, etc

- Stakeholders: This covered key partnerships, investors, funding, Board of Directors, etc

- What’s Not Working: I think this is self explanatory

- Other: A catch-all heading

Each week, executives went in before the meeting and put topics under each area, with their initials beside their topics. I would then choose which topics we covered at the meeting, based on what I thought was most important on the list. The format was one we stole from another company, and what I liked about it was that it forced us to look at the business through different lenses in each section. Sometimes issues would bleed across sections, and this forced us to acknowledge that Customers and Team might have different perspectives with a certain issue.

The “What’s Not Working” section was also useful because it encouraged people to bring up broken processes or problems that may have otherwise gone unnoticed.

3. Weekly Coffees
Once a week we had a 15 minute optional meeting in our main open office area where we quickly introduced new hires and covered any key topics that might be of interest to the team. It was mainly announcements.

4. Monthly All Hands Meeting
These meetings started around 4:30pm and ran about an hour. Every month we started by highlighting our goals for the year and our progress against them. We covered key metrics, new hires, product launches, etc. Sometimes an executive would give a 10 minute talk about a key topic. It could be a topic related to the business, or something more general about careers or whatever. For example, our VP of Engineering gave a talk called “Managing Up” which was all about how to make your boss successful, and it was one of the most popular talks we ever had. We usually went out to the bar for an hour after this.

5. Monthly Communications Course
I realized about two years in that many problems arise in companies because people don’t know how to talk to each other. So every month I personally taught a Communications Course that every employee had to take once a year. Usually it was filled with whoever started that month. The focus was on concepts like: how to have difficult conversations, or driving to clarity in your conversations, or how to sell ideas internally, etc.

6. Monthly Management Deep Dives
As the company grew, we inevitably had problems that required more than 45 minutes of management discussion. But, it was very difficult to block out 2-3 hours of time on the calendars of 5-8 busy executives on short notice. So we start putting placeholders in far in advance for monthly deep dives. We would hold 3 hours on a Tues or Wed afternoon. A few days before, we would decide what we would actually talk about at that meeting. Occasionally we would cancel them because we didn’t have any key issues to discuss, but that was rare.

7. Quarter Operating Reviews
We only started these our last year, but I really liked them. We blocked out one and a half days per quarter and had each department come in and present last quarter’s results, progress this quarter, and next quarter’s plan. It was a rolling quarterly thing. The exec team would be in all sections, and then each section also had key individual contributors come in from that team. It was a great meeting to get people in alignment, and helped me a ton as CEO. For example, knowing that once a quarter I got to take a Marketing deep dive and look at things like detailed analysis of PPC campaigns and leads from events we ran and landing page A/B testing results meant that I got to learn, and give my input, without having to nag the marketing team all the time about the details of what they were doing.

8. Twice a year management offsites
We did two offsites a year. The spring offsite in April was 2 days and was focused on whether or not the plan for the year was working, and also on executive development. The executive team would do presentations on areas where they had some expertise, and we talked a lot about team and culture. The fall offsite was 3 days and was focused on strategic planning. We started on the first day with a refresher about “what is strategy” and reviews of the business performance, market changes, and technology changes. Day two was all about taking that analysis and building some ideas for the next year, and Day three was all about finalizing that information into a formal plan.

The only other thing I will add to this is that we had an email address alignment@, and we used it to have important discussions that were far reaching, or send out key information about changes in the market, news, etc. All the execs were on it, as were about 15 key individual contributors. It was a good channel for debate and discussion.

The purpose of all this was to accomplish a few things. First of all, I was always trying to get lots of cross functional discussion going, because it was amazing to me how small a business can be and still have teams in silos. Secondly, I wanted to make sure there was ample opportunity to discuss key issues and problems in the business. One of the hardest things about being CEO is getting people to share bad news, so, you have to create forums where they can do that openly without being punished. Otherwise, problems fester and just get worse.

Over my time running Backupify I became fascinated with organizational structure and communications architecture for companies, and how to use it to get the best performance out of people. I’ve given it a lot of thought, and so, if you are interested in it too, or want to talk more about this, drop me a note and I’m always happy to chat.

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