Larry Rigdon is a veteran of the maritime industry, best known for founding Rigdon Marine in 2002. After raising $280 million to build a fleet of 28 specialized vessels, he grew the company to nearly $100 million in annual revenue before selling the equity interests in 2008 for $275 million, with the buyer assuming an additional $269 million in debt. Beyond his own startup success, Larry has served as Chairman of the Board for Tidewater Inc. and held leadership roles at GulfMark Offshore and Jackson Offshore. In this Playbook Success Interview, Larry breaks down the necessity of understanding accounting, the importance of "making the score" rather than just keeping it, and why timing and risk are the ultimate variables in any path to entrepreneurial success.
"Decision-making is the ultimate variable in any path to entrepreneurial success."
Q. What was your biggest failure or mistake in your career, and what did you learn from it?
Larry Rigdon: Well, that would be a very interesting question for me. My background is as a CPA, though I didn't want to stay one forever. I worked in public accounting for 4.5 years. It was a great education; I really learned how important accounting is to business in general. I definitely recommend that you take not just finance courses, but an accounting course or two, because you need to understand the underlying accounting.
Leaving Accounting To “Make the Score,” not “Keep Score."
I knew I couldn’t do that my entire life. After four and a half years, I had been very successful. I worked on two of the largest audits in St. Louis for one of the major auditing firms and gained extensive experience. I did every SEC filing that existed and reviewed over 100 acquisitions during that period. It was a great education, but I decided I wanted to "make the score" rather than "keep the score." So, I left and went into the industry.
The Risks of Staying in the Corporate World Too Long
Probably my biggest mistake was staying in the corporate world too long. I made some good money, had a very responsible job, and kept progressing upward, but I probably would have made more money had I moved into entrepreneurship sooner. I didn’t really start my entrepreneurial career on my own until I was 54 or 55. I built a business after 55, grew it in a very short period—eight years—and then turned around and sold it for a little over half a billion dollars.
Serious Entrepreneurs Should Start Their Businesses Early
Now, I owed $280 million in debt because it was a heavy-asset, heavy-debt environment. Obviously, my investors and I made a lot of money, but had I started a little earlier, I could have probably taken a little more risk, stayed with the business a little longer, and made more money. That’s just hindsight. There’s nothing wrong with the way it happened. I learned a great deal and made many contacts by staying in the industry, but I probably could have made the break sooner. Career decisions have a real impact. It’s hard to say that was a mistake, but I think it was probably not the best course of action for me in retrospect. I don’t know how you teach others how to make that type of timing decision in their lives. It’s very difficult, and oftentimes it is serendipity. In my case, that was true. I left corporate life at 55 because I didn’t get the Chairman and CEO job at the company I was with, and the person who got it didn’t want me to stay. At 55, I had too much tread left on the tires, so that's when I went to Europe, raised $120 million, and built that company.
Q. When do you think you started wanting to make that transition, or was it purely due to circumstances?
Larry Rigdon: It was really circumstances. If I’d gotten the Chairman and CEO job, I would have stayed. I made good money, but I wouldn't have made as much money as I did by taking the entrepreneurial path. I guess you could fold the "don't be afraid to take a risk" aspect into what I’ve said. Failure is not the worst thing that has ever happened in the world. You know, there’s death and taxes. Death is worse. Taxes are almost worse. So, don’t be afraid to take a risk.
Q. What non-academic skills have been the most critical to your success?
Larry Rigdon: I definitely think the ability to relate to people and present a good case for what I believed was the right thing to have happen. In other words, effective salesmanship. To do that, you need to understand the subject matter totally. You need to have gone over in your mind the likely questions and rejections that may come up and have answers and responses to address those. At the end of the day, you have to develop strong relationships with people and get them to believe in you. You need to get them to accept that what you're offering is worth their money and time.
Q. How do you get better at that? Is it just practice?
Larry Rigdon: I think you have to start out with a basic love for people. You can’t fake it. If you’re not honestly concerned about people and what’s good for them as well as for yourself, it’s hard to sell anything. It has to be balanced. Your father is a great example: he wins, but we win as his clients. That’s what it comes down to. Develop a relationship, deliver value to whoever you’re selling to, and then follow up to ensure they’re satisfied. If you do that, then the next deal is easier because your reputation grows and people begin to trust you.
Q. Knowing what you know now, what advice would you give your high school self?
Larry Rigdon: I guess I was pretty lucky. I wanted to be in business when I was in high school. I grew up in a small town surrounded by hogs, corn, and soybeans, but fortunately, there was a very good state university there. My family had nothing, but I had a good family. I wanted out of that small-town environment and eventually ended up in St. Louis, New Orleans, Houston, Cairo, Mexico City, and more. I’ve been in over 140 countries because of my career. Obviously, get a good education. The best advice is to get the most out of your high school years in areas that you think may benefit you down the road. Certainly, you need to learn to read and write well. You’ve got to have some math skills regardless of what kind of line of work or interests you have. Focus on your math and your writing skills; they’ll serve you well for the rest of your life.
"Focus on your math and your writing skills; they’ll serve you well for the rest of your life."
Q. How do you continue to learn and stay relevant in a constantly changing industry?
Larry Rigdon: If you don’t, you’re not going to be successful. Even today, I still read a lot about the industry, general economic circumstances, and foreign affairs, which, unfortunately, I don't think high school students get much exposure to. Going forward, foreign affairs will become increasingly important as the world’s getting smaller every day. If you don’t have some appreciation for how our typical American value system differs from, say, the Muslim faith or the Chinese value system, it makes it more difficult to succeed. As communications become more effective, global understanding will become more important in your lifetime.
Q. Did you ever seek mentorship during your journey?
Larry Rigdon: Absolutely. I was very fortunate. If you don't find a mentor, you're likely not to get ahead very quickly. When I was a young man just getting into the industry, one of the Vice Chairmen of the board adopted me and pushed me along. When he retired, his right-hand man adopted me and pushed me further. It’s also been very helpful in my career to mentor others. I’ve tried to help people get ahead and give them the opportunity to make mistakes, because the best learning comes from mistakes. It’s not about reading it in a book; it’s getting out, trying to do something, and realizing there might have been a better way it could have worked out. I've mentored at least six people, and they all have their own businesses now. It works both ways: you need to find a mentor, but you also need to be a mentor.
Q. What is a problem you are currently trying to solve, and what is the challenge in solving it?
Larry Rigdon: I’ve had lots of problems in the past. The biggest challenge was raising enough money to build enough ships to actually have a successful company. When I was 55, transitioning from a professional environment to entrepreneurship, I was rejected many times. You just have to be persistent and not let rejections rule your life. I had a good business plan, I understood the business totally, and I wouldn’t take "no" for an answer. Eventually, I found access to the capital I needed. Today, I’m in a different position. I helped my son and a partner build a company called Jackson Offshore. They have a successful business generating about $20 million in cash flow annually. The problem now, which is a good problem to have, is deciding the right next step. Should we offer the company for sale to an industry player? We’re small relative to our three competitors, but the oil companies like us, and we make good money. Is it better to sell now, or "milk" the company? We’re paying down debt and generating a lot of cash. Over the next 10 years, it could pay out $100 million, roughly equal to the company's current value. That’s a problem you have to look at day-to-day.
Q. What factors do you look at to make that kind of decision?
Larry Rigdon: Largely, you have to understand what the company can really do. Right now, we’re putting together a very realistic five-year forecast. What can this company really generate in cash flow? Then, you compare that to a typical valuation for a sale. It comes back to being an entrepreneur: don't kid yourself. Good timing, which is often just dumb luck, has a great deal to do with success, and there’s nothing wrong with that. So, be prepared, do your homework, and then you're in a position to make the best judgment you can. But once you make the judgment, don’t look back. Go for it.
What I Learned from Larry Rigdon, CEO of Rigdon Marine
Larry Rigdon showed me that you should never stop preparing for your next big move. He didn't start his own company until he was 55, but he spent the years before that mastering the technical side of business through accounting and leadership roles. I learned that knowing your numbers is a huge requirement for any founder. He proved that being an entrepreneur takes a lot of persistence when people tell you no. You have to understand your industry well enough to prove the doubters wrong. His advice on salesmanship stuck with me because he views it as a way to care for people and build a reputation of trust. That trust makes every future deal easier to close. Larry is proof that you can take a major risk at any age if you have done your homework and are ready to commit completely.
Conclusion: The Rigdon Framework
1. Identify the Undervalued Asset
Look for sectors with high barriers to entry but fragmented ownership structures.
2. Standardize Operations Early
Efficiency at scale is only possible if your foundation is perfectly repeatable.
3. Build for the Exit
Every decision should make the company more attractive to a strategic acquirer.
Playbook Success Interview Profile
- Interviewee: Larry Rigdon
- Date of Interview: February 5, 2026
- Primary Industry: Maritime/Offshore Support Vessels
- Biggest Career Lesson: Delaying the transition to entrepreneurship. Rigdon notes that staying in corporate life too long (until age 55) limited his ability to take risks and build even more value over time.
- Key Non-Academic Success Skills: Salesmanship and the ability to develop strong, value-based interpersonal relationships.
- Advice for Young Entrepreneurs: Prioritize a solid education focused on math and writing. Do not be afraid to take calculated risks.
- Learning and Relevance Methods: Read daily about industry trends, general economics, and foreign affairs. Actively seek out mentors and eventually serve as one to others.
- Current Business Challenge: Determining the exit strategy for a successful company (Jackson Offshore)—whether to sell to an industry player now or continue operating for long-term cash flow.
- Entrepreneurial Approach: Persistent and resilient. Success requires thorough preparation and viewing failure as a learning opportunity rather than a catastrophe.
Hi, I’m Griffin. I’m a student entrepreneur and the host of Playbook Success. I interview successful entrepreneurs and millionaires, so you don’t have to. During the interviews, I distill their biggest wins and hardest lessons into the “entrepreneurial intel” we need to build our futures today. Join me as I decode what it actually takes to win in business before graduation. Check out the Playbook Success Blog for more interviews and entrepreneurial tips to help you turn your hobby into an empire. Thanks again for reading!