From Marine to Entrepreneur: Nathan Dobbins' Journey in Real Estate and Hospitality

Episode Summary

In this inaugural episode of "Neil on Business," host Neil Darling sits down with Nathan Dobbins, a Marine veteran turned successful entrepreneur in Fredericksburg, Virginia. Nate shares his winding journey from studying forestry at Virginia Tech to serving as a heavy equipment mechanic in Afghanistan, then pivoting through various careers before finding his calling in real estate investing and the restaurant business. Now a key player with the Riffing restaurant group and a respected real estate investor, Nate reveals how Marine Corps values of integrity and perseverance have guided his entrepreneurial success. He discusses the challenges of transitioning from military to civilian life, the importance of strategic networking, and how failure can be a stepping stone to success. This conversation offers valuable insights for veterans considering entrepreneurship and anyone looking to understand the mindset required to build lasting business relationships.

About Nathan Dobbins:

Nathan Dobbins is a Marine Corps veteran who served eight years as a reservist, including a seven-month deployment to Afghanistan in 2011 as a heavy equipment mechanic with the 4th Combat Engineer Battalion. After trying his hand at various careers post-military—from maintenance supervision to cybersecurity—Nate found his passion in real estate investing, specializing in vacant land wholesaling. He currently works with the Riffing restaurant group, helping manage their portfolio of four restaurant concepts including Rebellion, Castiglia's, and Port Osteria & Brewery. Nate is also a prominent networker in the Fredericksburg business community, hosting monthly real estate investing meetups and serving on the board of directors for the local builders association. A father of three and devoted family man, he exemplifies how military values translate into entrepreneurial success.

Key Topics Discussed:

• Military Service and Deployment: Nate's experience as a 1341 heavy equipment mechanic in Afghanistan and the challenges of IED threats
• The Difficult Military-to-Civilian Transition: Why veterans struggle adapting to civilian careers and the importance of being a self-starter
• Career Pivots and Failures: From forestry to cybersecurity (82 applications, 1 interview) to finding success in real estate
• Real Estate Investing Strategies: Wholesaling vacant land, working with hard money lenders, and building a reputation in the industry
• Restaurant Business Insights: The 75-80% failure rate, the importance of business operations over just cooking skills
• The Riffing Restaurant Group: Managing multiple concepts (Rebellion, Castiglia's, Port Osteria) to serve different market segments
• Investment Opportunities: How investors can participate in restaurant ventures through fractional ownership
• Strategic Networking: The difference between "networking" and "not working" - being intentional about relationship building
• Ethics in Business: Why integrity is the last thing you have when everything else fails
• Entrepreneurial Advice: The importance of perseverance, knowing your numbers, and helping others first

Powerful Quotes from the Episode

"Perseverance is probably the most important thing that an entrepreneur can have to be successful. And I think the Marine Corps does a good job of instilling that in people and drawing the best out of people that they have inside them."

"If you're an entrepreneur or whatever you're doing in business or if you have a job, if you fail your job or your business fails, your integrity is really the last thing that you can have and hold on to."

"It's important to remember that if you're failing, that means you're trying. And there are plenty of people out there that aren't trying. So as long as you keep trying, you're doing the ethical thing, you're staying knowledgeable in your industry, just keep trying."

"The way I go into it is I honestly, I really just sit down, I ask how I can help. Typically when... if I go in, I talk to someone like, hey, how can I help you? What are you looking for right now?"

"Real estate investing is crazy. You know, there's tons of different avenues inside of real estate investing. Most people's experience is HGTV, right? So they think flipping is what a lot of people come to the industry thinking they're going to do. Flipping is risky."

"You really, it's called networking, right? You have to work at it. You have to be intentional."

"Find a mentor, find someone that's doing what you want to be doing and find a way to provide value to them or just try to find a way to get around them, just to learn from them."

Resources

• Nate's Real Estate Meetup: Last Tuesday of every month, 6 PM, 9-11 Charles Street, Fredericksburg
• Ring Spaces: Host location - use free day pass at freedaypass.ringspaces.com
• Riffing Restaurant Group: Rebellion, Castiglia's, Port Osteria & Brewery
• Business Resources Mentioned: BiggerPockets.com for real estate investing education
• Networking Opportunities: Various Fredericksburg business networking groups
• SBA Office at Mary Washington: Resource for new business establishment

Connect with the Show

• Ring Spaces Studio: Check out the co-working and podcast facilities in Fredericksburg 
• Neil on Business Podcast: More episodes featuring Marine entrepreneurs coming soon
• Host: Neil Darling, owner of Ring Spaces

Loved this episode? This is just the beginning of Neil on Business - stay tuned for more conversations with Marine veterans who've traded uniforms for boardrooms and built successful businesses through discipline, integrity, and entrepreneurial spirit.

Podcast Produced and edited by the team at ResilientVoiceMedia.com

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