Brandon Webb

Be open to change and avoid ‘the temptation of certainty’. Nothing in life is certain, the sooner we make peace with that idea the better off we’ll be as entrepreneurs.


After leaving home at 16 Brandon finished high school and joined the US Navy. In 1997 his SEAL training package was approved, and he joined over 200 students in class 215 and went on to complete the training as 1 of 23 originals.

As a SEAL he served with SEAL Team 3, Naval Special Warfare Group One (NSWG-1) Training Detachment sniper cell, and the Naval Special Warfare Center (NSWC) sniper course; where he served as sniper Course Manager. Throughout his career, he completed four deployments to the Middle East, one to Afghanistan and deployed to Iraq in 2006-7 as an OGA contractor.

Brandon was meritoriously promoted to First Class Petty Officer, ranked #1 in the Command, while assigned to Training Detachment sniper cell. Shortly after, he was promoted to the rank of Chief Petty Officer (E-7). He has received numerous service awards including, Top Frog at Team 3, the Presidential Unit Citation (personally awarded by President George W. Bush), and the Navy and Marine Corps Commendation Medal with “V” device for valor in combat. Webb ended his Navy career early to spend more time with his children and focus on new entrepreneurial endeavors.

Brandon lost his first business, and entire life savings, but went on to found the Hurricane Group, a men’s lifestyle company with digital publishing and eCommerce brands that reach over 50M monthly. Brandon also co-founded GSD Logistics, a third party fulfillment (3PL) company focused on global fulfillment for eCommerce companies.

Brandon is regularly featured in the media as a military and business subject matter expert. He has contributed to ABC’s Good Morning America, NBC’s Today Show, CNN, the BBC, SIRIUS XM, MSNBC, Fox, The New York Post, and The New York Times.

Webb is a multiple New York Times bestselling author. His books include The Red Circle (St. Martin’s Press), The Killing School (St. Martin’s Press), The Power of Thought (Self-published), and Mastering Fear, a Navy SEAL’s Guide (Penguin-Random House). Several additional titles have been released within the young adult category.

In 2012, after losing his best friend, Navy SEAL Glen Doherty, in Benghazi, Libya, he founded The Red Circle Foundation (RCF), a non-profit with a 100% pass-through model; every dollar donated goes to the mission and business partner donors pick up the Foundation’s overhead. RCF is focused on supporting families of the Special Operations community through emergency memorial, medical, and child enrichment programs (camps & scholarships). In a short period of time, RCF has donated just under a million dollars in grants to Special Operations families.

Brandon attended night school on active duty at Embry Riddle Aeronautical University and post navy at Harvard Business School’s OPM program. He is a member of the New York YPO (Young Presidents Organization) chapter and served as a board member on the veterans advisory committee to the U.S. Small Business Administration.

Where did the idea for your company come from?

I modeled the company after my platoon in the SEAL Teams. We are fast and nimble and just get stuff done. Recently, one of my team members said we’re like a storm, hence why we chose the name Hurricane Group…”Business by Storm”.

What does your typical day look like and how do you make it productive?

I actually don’t have a typical day, which is why I like our business so much. We are a digital content and e-commerce product-focused business, so on any given day, I get to jump from product design to digital marketing to content and back again.

Last year we made a documentary that I helped direct and produce called, Big Mountain Heroes. It’s about combat veterans using nature and the outdoors (skiing and snowboarding) as a therapeutic outlet.

The motto was, “Thrills before Pills”.

How do you bring ideas to life?

This is a great question because good ideas are everywhere but very few people can execute them the way my team does.

We had an idea to test a new subscription box category for our existing Crate Club Box (tactical and survival gear handpicked by former Navy SEALs, Army Rangers, etc.) in December. We had product sourced, packaging was designed, and we launched one month later.

I don’t know too many teams that could execute and bring this idea to life so fast but our team is amazing and incredibly quick. One of our business mottos is, “You dream it we make it happen!”. We stand by that promise.

What’s one trend that excites you?

VR is super exciting and a growing trend.

I think it will be the next ‘Internet revolution’, just like in Steven Spielberg’s movie, Ready Player One.

In the near future, content and commerce will be experienced in VR in ways that are incredibly exciting and will certainly disrupt, the same way digital has displaced traditional cable and entertainment companies.

What is one habit of yours that makes you more productive as an entrepreneur?

If I had to pick one thing… it’s my To-Do List and OKRs that keep me most productive. We are an ‘Objectives and Key Results’ driven business.

What advice would you give your younger self?

To be more kind to people.

Tell us something that’s true that almost nobody agrees with you on.

Today, America isn’t the best place to start an online business. People are better off starting it in the EU and applying for e-residency in Estonia. Better tax optimization, you can still access US markets, better freedom of movement (fewer restrictions), and ZERO bullshit litigation risk (e.g. Getting sued because your website isn’t ADA compliant, etc…).

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Execute, execute, execute.

What is one strategy that has helped you grow your business?

To be open to change and avoid ‘the temptation of certainty’. Nothing in life is certain, the sooner we make peace with that idea the better off we’ll be as entrepreneurs. The head of CBS told one of my board members years ago that nobody would read their news on the Internet.

We all know how that worked out.

What is one failure you had as an entrepreneur, and how did you overcome it?

I lost my first business, got a divorce right after, my entire life savings was wiped out and to top it all off… I owed people a lot of money. It was incredibly terrible but incredibly humbling. I realized, by drawing on my experience training SEAL snipers in positive psychology, that I had to take from my own teachings and focus on the positives.

I had to let go of the missed shot and focus on my next target.

I realized I had lived through what was an incredible life learning experience, and in the same breathe had acquired the skills and ability to start another business.

“So I did the one thing I knew I had to do… I got started.”

What is one business idea that you’re willing to give away to our readers?

There’s so many!

This one idea was borne out of the constant consumption of materials and the growing excess of waste in consumer packaging.

There are easy ways of creating beautiful packaging that will wow the customer while staying environmentally-friendly and keeping your brand’s carbon footprint close to invisible.

Imagine telling Nike you’re going to save them over a $100M a year by creating better quality and more efficient packaging and that they’ll be able to relay that story to consumers. It’s a great business model, a marketing department’s dream, and extremely Earth-conscious. Sign me up!

What is the best $100 you recently spent? What and why?

Hamilton tickets for my daughter’s birthday. When it comes to experiences like this, it’s money well spent. She’ll remember that show for the rest of her life.

What is one piece of software or a web service that helps you be productive?

We use Google Sheets as an easy way for our team to share company-wide Objectives & Key Results (OKRs). It’s simple and extremely effective.

What is the one book that you recommend our community should read and why?

The Tree of Knowledge: The Biological Roots of Human Understanding by Humberto R. Maturana, Francisco J. Varela, J. Z. Young.

That book rocked my life in so many good ways. Incredible lessons in there that can be applied to life and business. Read it.

What is your favorite quote?

I like Churchill’s quote about enemies, we all have them if we’re standing up for what we believe in and making things happen.

“You have enemies? Good. That means you’ve stood up for something, sometime in your life.”
-Winston Churchill

Key Learnings:

  • Let go of past failures and focus your energy on what to do next.
  • We can all find ways in our business to help save the earth.
  • Nature and the outdoors can be a very therapeutic outlet. Thrills before Pills!
  • Execute. Execute. Execute.
  • Be more kind to people


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