Alex Caslow of Red Beard Sailing: “People shouldn’t expect to get rich or make a fortune”

In my industry, people shouldn’t expect to get rich or make a fortune. This business is a way to make a good living while enjoying the line of work. You will have the freedom to enjoy sailing on a weekday. You will also become a Subject Matter Expert (SME) for the brands of boats you […]

The Thrive Global Community welcomes voices from many spheres on our open platform. We publish pieces as written by outside contributors with a wide range of opinions, which don’t necessarily reflect our own. Community stories are not commissioned by our editorial team and must meet our guidelines prior to being published.

In my industry, people shouldn’t expect to get rich or make a fortune. This business is a way to make a good living while enjoying the line of work. You will have the freedom to enjoy sailing on a weekday. You will also become a Subject Matter Expert (SME) for the brands of boats you represent. The best piece of advice I can give is, you need passion. Passion is the best salesman in the world.

As part of my series about the leadership lessons of accomplished business leaders, I had the pleasure of interviewing Alex Caslow.

Alex was born and raised in Baltimore, Maryland. He earned an AA from a local community college and has had a job since he was 13 years old. He worked in a drive-in movie theater and then IKEA, where he learned marketing and retail practices. He then got a job working in the automotive industry where he learned operations and inventory management. In 2015 Alex started Red Beard Sailing, a portable boat dealer and online retailer based in Baltimore. It started with humble beginnings, but 5 years later he has carved out a new niche in the US sailboat market.

Thank you so much for joining us! Can you tell us a story about what brought you to this specific career path?

I have always wanted to own my own business, and work for myself. I always found myself frustrated at work by inefficient processes I had no power to change. I have always struggled with doing things for the sake of “because that is the way we have always done it.”

I wasn’t actively looking to start a business when I found our first product. I wanted to buy a portable sailboat. I did my research and picked the perfect fit for me, but I hit a wall when I found I it wasn’t being sold in the USA. I quickly realized that there might be a market for this type of product and if it was successful, I would be finally able to do what I love as a profession and work for myself.

Can you tell us a story about the hard times that you faced when you first started your journey?

After starting in August 2015 and getting only a couple sales under our belts, we attended the Baltimore Boat Show. It had recently snowed but foot traffic was up over the previous year (so they told me).

We couldn’t afford a booth big enough to set up a whole boat, so we built a PVC rig that held the boat at an angle (but without a mast).

We had some brochures, business cards and a picture collage of the boats in action. We nearly had someone on the hook for a discounted boat but ultimately, we ended the show having made zero sales.

We were crushed.

My wife and I talked about if this was just a bad idea and not worth putting more money or effort into, but we stuck it out until the Annapolis Spring Sailboat Show.

We killed it at the Annapolis show. With this proof of concept, we signed a local marketing firm with a plan of attack and things took off from there.

Where did you get the drive to continue even though things were so hard?

Because I am a passionate sailor at heart, and one that has owned larger boats, I knew that this was a product that would solve a pain point. I had to realize that the products I was trying to sell didn’t really have an existing market in the US. I needed to curb my expectations and try and think from the customer’s perspective and how to educate them on the options my products offered.

So, how are things going today? How did grit and resilience lead to your eventual success?

Things are going really well today. We finished 2020 with 150% higher sales than we had the year before. We’ve always been able to start a second related company to capture even more of the market. I have worked through months where we didn’t make enough profit to pay myself and I have taken minimal salary in months where we have had record profits. Seeing the larger picture and working towards long term goals help me keep a focus on what comes next. Owning a business is all about what is next, if you aren’t moving, you’re sinking.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

It is really tough to laugh about mistakes that I make as an entrepreneur, at least in the moment. The funniest one would probably be the time I mistook a journalist for a customer at a boat show. I’m not sure how I missed his badge, but I knew right away he was an enthusiast. I was really doing my best to sell him a boat. It turned out he was an editor of SAIL Magazine looking for new products to feature. I spoke to him just like I would a customer at a boat show (we were at a boat show). It is hard to tell if that was the reason, but against all odds, the boat we were discussing won Best Daysailor of 2017!

The lesson I derived from that is: Be passionate and genuine, always. Had I known he was a journalist, I probably would have stuck to the spec sheet and talking points. My customer conversations tend to be more candid and usually include a number of my sailing stories. This experience taught me that whether I am talking to a customer or writing copy for the website, I need to be genuine and keep the marketing jargon to a minimum. Customers can read the spec sheet without me. They appreciate that they are talking to not just a salesman, but a fellow enthusiast, so don’t be afraid to be personal.

What do you think makes your company stand out? Can you share a story?

My company stands out by offering niche products that allow people greater access to the sport of sailing. Before we started our business, you needed to have a trailer or a slip (or both) to have a sailboat, but that’s ancient history now. We sell sailboats that fit under your bed or in your hall closet and that mean pretty much anyone can have one. We love sailing and we personally use all of our boats. We can provide specific experience to the customers for nearly any question and we do so with an apparent passion. That gives customers the confidence to buy from us and trust our recommendations.

I competed in the 2018 Everglades Challenge (EC) in one of our products, the XCAT. The XCAT is a 16ft boat that you can disassemble and strap to the roof of a sedan. The EC is a 300 mile unassisted expedition style race from Tampa Bay to Key Largo. It has a 60% drop out rate and is known as one of the most difficult small boat races in the US. I was willing to put my money where my mouth was and make a bid at the EC in one of our products to prove the durability and performance capability. I did end up dropping out of the race, but not until after travelling 130 miles from the start line, and in weather than even had Olympic medalist sailors needing a coast guard rescue!

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

In my industry, people shouldn’t expect to get rich or make a fortune. This business is a way to make a good living while enjoying the line of work. You will have the freedom to enjoy sailing on a weekday. You will also become a Subject Matter Expert (SME) for the brands of boats you represent. The best piece of advice I can give is, you need passion. Passion is the best salesman in the world.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

My wife has made all of this possible. She had a “real” job through the first 4 years of our business. In addition to her duties there, she also worked boat shows and helped me ship boats out when we got busy. I am very fortunate to have had the perfect conditions for my business to thrive in its early years.

How have you used your success to bring goodness to the world?

I have been able to donate boats to programs and charities that bring underprivileged children and people to the water. Sailing is widely thought of as an elitist sport, but with a partnership with ChesX Sailing Center, we have been able to help people who struggle with substance abuse by teaching them to sail and then equating those skills to real world skills. Through the same sailing center we have also been able to get hundreds of underprivileged kids on the water with no cost to them.

My mom always taught me the joy of helping others, and I intend to never stop paying it forward.

What are your “5 things I wish someone told me before I started leading my company” and why. Please share a story or example for each.

  1. If you are selling a physical product, then logistics will be your new least favorite thing in the world. Learn logistics, even take a class or read a book on supply chain logistics because it is a bear.
  2. Stay at your job. Your business is not going to grow as fast as you think and you will want to avoid taking any money out of your business in the first year. I actually held to this one pretty good, but my company could have used 6 more months of not paying my salary.
  3. If you do get overrun with opportunity and sell out, don’t overreact. Stay the course and work your plan for the year. You can get yourself into big trouble by spending funds to “keep riding the wave”.
  4. Ask your accountant about SEP IRA contributions. This is your 401k. Just because you are self-employed, doesn’t mean you don’t need to think about retirement. You can contribute to a SEP IRA and reduce your tax exposure all while saving for later in life.
  5. This one is a bit niche but… Keep an eye on that exchange rate. Because we buy most of our goods from Europe, we pay in Euro. The price of the Euro went from 1.03 dollars to 1.30 dollars in only a few months and it ended up costing us a bunch of money.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

I have always believed that education is the key to our success as a society and our society is largely missing the mark. My wife and I intend to start a non-profit trade school that specifically offers education in the different trades to underprivileged people at little to no charge.

How can our readers follow you on social media?

You can follow me on social media by following:

FB: @redbeardsailing

IG: @redbeardsailing


This was very inspiring. Thank you so much for joining us!

Share your comments below. Please read our commenting guidelines before posting. If you have a concern about a comment, report it here.

You might also like...


Terysa Vanderloo and Nick Fabbri of Sailing Ruby Rose: “This isn’t COVID related, but it’s equally important”

by Candice Georgiadis

Regatta de Catamarans

by Susan Jacobs

The New American Dream: From A Greek Immigrant Family to 7-Figure Entrepreneur

by Victoria Kennedy
We use cookies on our site to give you the best experience possible. By continuing to browse the site, you agree to this use. For more information on how we use cookies, see our Privacy Policy.