M&M 47: Entrepreneurship after the Military

What’s it like going from side hustler to full-time entrepreneur? When it comes to buying and selling websites, were you a flipper or did you have a buy-and-hold strategy? In Episode 47 of The Money and Media Podcast, PT Money interviews Curtez Riggs, founder of the Military Influencer Conference, about entrepreneurship after the military.

Curtez has several high-traffic websites and has quickly become an innovator and digital entrepreneur helping veterans establish online brands. He has also recently created a dynamic event that brings together hundreds of entrepreneurs, influencers, community leaders, and spouses united by a passion for the military.


Intro Curtez Riggs – veteran, entrepreneur, founder
3:50 Who is Curtez Riggs?
5:40 The switch from side hustler to full-time entrepreneur
6:55 Buying and selling websites as a business model
10:50 Does Curtez recommend that others follow the buy/sell approach?
13:45 Trends in entrepreneurship for 2018
16:55 How influencers, brands, and small businesses come together to benefit each other at the Military Influencer Conference
19:26 What to expect if you attend the Military Influencer Conference 2018

Meet Serial Entrepreneur Curtez Riggs

Curtez Riggs served 21 years in the Army before his retirement in April of 2018. He calls himself a “serial entrepreneur.” He has done a wide variety of things like freelancing, running a credit repair company, buying and selling websites, and launching a conference.

His current mission is to help others in the veteran and military spouse space find their way to successful entrepreneurship.

Making the Switch from Side Hustler to Full-time Entrepreneur

Since retiring from the military, Curtez says he feels like a kid who just graduated from high school and has been given a pass to take a break for a while. Freedom is feeling really great to him these days. His desire to give back is stronger than ever, though. While he isn’t punching the Army clock anymore, you can bet he isn’t kicking back on the couch either.

Curtez has always been busy with side hustles. Now that he isn’t devoted to a day job anymore, he can focus on the entrepreneurship full-time. The main difference has been the time required. When he was still employed full-time, his days looked very different than they do now.

There was very little time for family when he was trying to build up his side hustles while also working a regular job. He is now better able to manage his time and his load has been lightened tremendously.

Buying and Selling Websites

A few years ago, Curtez started a blog called Life After the Army. He intended to use that site to walk folks through how to prepare for retirement from the military and how he was doing it. After 7 months of writing in that space, he was contacted by USAA to be an influencer for them. It was at that point that he began to see the need for diversity in his business.

He eventually set up a site based on a struggle the Army was having. There was a huge struggle going on over boots. That’s right, boots. Curtez saw an opportunity and jumped on it. He set up a website that had every boot on it that the Army approved. He ranked them from first to last and wrote content about each one, what features made them preferable, and links to each pair of boots.

It took him 120 days to get the site profitable and when a move for his family became imminent, he sold the site in order to finance the move. And that opened his eyes to the possibilities of buying and selling websites.

Over the next several years, Curtez bought and sold many sites. In early 2016, he owned over 40 websites and he made the decision to start selling them off. He could sell a website for 15-20 times the most recent 90-day average sales. It was a lucrative business model for Curtez, but he was ready to move on to something new.

Should You Buy and Sell Websites?

I was curious if Curtez would recommend that others with some amount of internet savvy follow this approach of buying a website, loading it up with content, and then selling it. And he emphatically says yes.

“Why do something from the ground up when there’s already a market out there for you to step into and acquire?”

Curtez works with a nonprofit that specializes in working with those leaving the military. Many of these people are leaving military life with their entire life savings, and they want to get into some type of entrepreneurship. Instead of starting at ground zero or buying a franchise, Curtez wants them to look for companies to acquire.

Websites are companies, and if you have the resources to buy one and then manage it, why would you try to start something new? Whether you have just a couple thousand dollars to invest or six figures, there are opportunities to purchase websites and build them up into money makers.

Entrepreneurship Trends for 2018

Curtez is a huge fan of the blockchain and the cryptocurrency market. There are many different mindsets around these topics but Curtez believes that the blockchain represents disruptive technology.

With so many people coming out of the military and transitioning to online business, the opportunity there can’t be minimized. These people are leveraging the blockchain to create new ideas and new ways of doing business.

If you aren’t sure what we mean by disruptive technology, just think about these examples:

  • AirB&B and hotel chains
  • Uber and traditional taxis
  • Amazon and traditional bookstores
  • Netflix and cable television

Disruptive tech can be a risky venture but if you find a good fit, the rewards can be great. Think about startups. Ten years ago, if you had a start-up, you could bet that the founder and co-founder had offices in the same building. Now, more people than ever work online and the world is a lot smaller. The way we do business is no longer about sitting around a table in some boardroom somewhere. We rely on the internet to bring us together even if we are geographically far apart.

The Interaction of Brands and Military Influencers

At Curtez’s conference, there are bloggers, freelancers, podcasters, YouTubers, and content creators that just so happen to come from the military community. These creatives are looking for ways to leverage their skills to work with brands and small businesses.

Unfortunately, there are not a lot of options to bridge that gap between brands and the military. What Curtez has done is bring the brands to the conference that want to work with these creatives and that are already a good fit. Aside from the brands, there are small businesses and services that want to get their products and services in front of the military community. At the conference, they have an audience of creatives right there that are willing to work with them to do just that.

At the end of the day, the influencers are happy because they are finding work; the brands are happy because the primary people they want to extend their reach through are all right there; and the small business owners are happy because they can learn how to develop their content marketing and social channels.

If you are a military financial blogger or podcaster, you are retired or current military, or you are a military spouse, please be sure to check out the Military Influencer Conference. It’s a great community to get involved with if you have any interest in becoming an influencer or working with brands in the online space.

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About Our Hosts

Philip Taylor owns and operates FinCon as well at the personal finance website PT Money.

Joe Saul-Sehy is the co-host of the Stacking Benjamins personal finance podcast and operates the Stacking Benjamins blog.

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