Top 8 Moments at risk3sixty to Celebrate 8 Years in Business

Eight years. Eight. Years.

Like they say: "The days are long, but the years are short."

In some ways it feels like it has been closer to eighty years than eight. In other ways, I feel like we just started the business yesterday.

But goodness, I am truly loving the journey.

I am so thankful to be a part of this team. This thing that we are building together. I might be biased, but I wouldn't want to be doing anything else. I think what we are doing over here at risk3sixty is meaningful. Meaningful to the industry - and more importantly - meaningful to the lives of the people who work here.

And an important part of any milestone - like an 8-year anniversary - is reflection. So, in this newsletter I want to do a little reflecting. To show a little gratitude and enjoy a bit of nostalgia. About things come to pass, and about things in the future.

So here we go.

Here are the top 8 moments at risk3sixty to celebrate 8 years in business:

#8: The Evolution of Risk3sixty's Office Space

My wife is a wonderful woman. So wonderful, that she helped me assemble the furniture and paint the mural at our first office in a small shopping center in the North Atlanta suburbs. Before becoming risk3sixty's first headquarters, it had been a tennis racquet repair shop for 20 years. But darn it, our team was proud of that little space and we made it feel like home.

Fast forward 8 years and a lot has changed. We have upgraded offices - my wife and I didn't have to paint any wall this time around - but that same spark still exists and is evident all around us. If our physical space is any reflection of risk3sixty's journey - and I think it is - I am proud of where we've come from and where we are today.

#7: Doing Hard Things Together

In the "War of Art" Stephen Pressfield says that "The more scared we are of a work or calling, the more sure we can be that we have to do it." Why? Because the most valuable things in life are right on the other side of what most people resist.

And the major problem for most people is that we can't conquer our fear. We haven't built that habit of doing hard things. We haven't experienced first hand the joy of doing something hard and coming out the other side. We haven't given ourselves the opportunity to earn that type of confidence.

Many people never do.

So, in the early days of risk3sixty, almost as a joke, we decided to run a 100-mile relay race. I guess you can afford to do reckless things like that when you are a small start-up of only a few people. The fact that we did it at all was a fluke.

But what we learned during that (awful, but great) adventure is that shared adversity has the unique ability to do two things for a team: One, it fast tracks trust, and two, it is the fastest way I know of to prove to a team that there are huge rewards for doing hard things. (I wrote a lot about that here.)

As a result, doing hard things has become a cultural artifact unique to risk3sixty and our core values. And while "Grit events" aren't something I would recommend to most companies, it works for us. Many of my favorite memories include doing hard things shoulder-to-shoulder with a group of strange renegades.

If you're curious, here are a few of our "annual grit events":

• Two 100-mile relay races
• One 200-mile relay race
• A Spartan Race (pictured below)
• A 24-hour ruck

#6: Trying to Tell the World About Risk3sixty

At risk3sixty, our marketing philosophy is that if you give first, sometimes you get a little in return. To that end, we have made it core to our strategy to produce an endless stream of quality content.

Here are just a few examples:

• 221 Blog Posts
• 54 Whitepapers, eBooks, and guides
• 186 Videos
• 2 Courses
• 160 Conference Talks
• 1 Stand Up Comedy Set
• 1 Best Selling Book

The result of all of that hard work has been amazing both personally and professionally. For example, millions of people have viewed our content and we frequently get messages from people saying how it helped people accomplish their mission to get certified or get a job.

Heck, I went to Rocky Mountain Information Security Conference (RMISC) last month and a few strangers asked me to sign a copy of "Security Team Operating System". Little moments like that are surreal, but help remind me that our cumulative efforts are making a positive impact on the industry.

Side Note: Almost all of our results have come from the last 2 years. That makes me excited about things to come. We really are at the beginning of this grand journey.

#5: 32 Consecutive Quarterly Team On-Site Meetings

My experience at risk3sixty has been that every quarter feels like a year. As a result, one of the most important things we can do is help keep people focused, enthusiastic, and energized. And the way we have chosen to do that is a disciplined cadence of quarterly on-site meetings.

The purpose of these meetings is to reflect on performance over the last 3 months, recalibrate our goals and objectives for the next 3 months, and create an opportunity for the whole team enjoy time together.

As we have grown our team the logistics of flying a whole team to Atlanta has steadily become more complex. I mean, we have team members in 13 states. But man, let me tell you, the energy we get from spending time together - the clarity of how we should focus our energy - is well worth the effort.

#4: Publishing a Best Selling Book

On June 3rd 2024, I published my first book "Security Team Operating System". The book provides a 5-part system for security leaders to run their team: Purpose, Values, Roles Rhythms, and Goals. The system is exactly how we run risk3sixty and is based on lessons learned from 250 interviews with security leaders and over 2000 cybersecurity assessments.

Publishing a book has been a long time goal and was the result of 18-months of concentrated effort. I wrote all about it here and here.

#3: Passing $10M in Revenue

Amara's Law says that we often "Over-estimate what we can do in the short-term, but under-estimate what we can do in the long-term." I have found that to be true for us at risk3sixty. When we first started risk3sixty we set a goal to hit $10M in revenue by 2027. $10M represented an important maturity milestone for risk3sixty, but also seemed so far away.

We hit and passed $10M much faster than we expected and it was validation that we were headed in the right direction. Validation that all that talk about vision and values was true. Validation that the market appreciates our products and services.

$10M was not the end of a journey - but much closer to the beginning.

#2: A Month-Long Sabbatical

At risk3sixty, we have a sabbatical program where all team members earn a month off for every 5 years of service.

• 1 month off after 5 years
• 2 months off after 10 years
• 3 months off after 15 years

As employee #1 was the first person to enjoy this company benefit. I had to take it to make it real. My family and I spend most of the month in Wyoming and Montana visiting Yellowstone and towns like Livingston and Bozeman. That experience gave my family time and space to connect - a rare gift not often afforded in life. Now, 8-years in, many other folks on the team have enjoyed a sabbatical of their own - or are gearing up to enjoy it very soon.

#1: Babies, Houses, Families, and More Babies

Over the last 8 years I have had the amazing opportunity to watch people launch careers, buy homes, get married, and start families. It is fulfilling to watch risk3sixty grow into a business capable of supporting so many excellent people and their families.

One of my favorite benefits at risk3sixty is that new Dad's get 6 weeks off and new Mom's get 3 months off. This one hits home for me because I didn't take much time of when I had my first two kids. We were neck deep in start-up mode at risk3sixty. But when we had our third child, Sonora May, back in August I took the full 6 weeks. It was life changing. I'm proud our company can offer this experience to our team. It's just a small way our company tries to put family first.

Side Note: I don't know what's in the water here at risk3sixty, but by my last count our team is having 13 babies this year. We've had so many kids that we decided to make a risk3sixty onesie that comes in either pink or yellow.

What's Next

I am so excited and optimistic about the future of risk3sixty. Not because of some aspiration of explosive growth and not even because of the products and services we offer. Of course, I believe in both of those things, but that's not why I am excited.

I am excited because I am confident in the principles and people that make up the foundation of risk3sixty. When I look back over the last 8 years those are the things that prove out to be what makes the difference. Those are the things that make up my highlight reel.

Join Us

So, if you are looking for a place to call home - I hope you consider risk3sixty. Whether you are looking for a vendor to partner with or a place to launch a career we would welcome the opportunity to be a part of your journey.