By Christa Fletcher, a contributor of The Underground Group
⏰ 7-min read

In short:

  • How do you grow into a formidable e-commerce brand when you launched before e-commerce was even a thing? Nautical retailer Sailrite has a story that offers answers.

  • The family-run business has expanded into avenues both lucrative and not-so-profitable over its 50-year history.

  • Through it all, a carefully-crafted leadership dynamic keeps the team winning.

The Grant family knows what it’s like to sail into success, literally. Their business Sailrite has produced boat sails--and taught others how to make them--for 50 years. Today, the Indiana-based e-commerce company ships between 500 and 700 product orders daily while running a branded YouTube channel with 188,000 followers.

The Grants cite tech-savvy marketing, a customer-first philosophy and three generations at the mast as critical to their company’s continued success.

Like many great startups, Sailrite started out of necessity.

Sailrite’s story began in 1969, when married founders Jim and Connie Grant started making their own sails for Jim’s boat. Jim was a college professor and competitive sailor. He needed new sails before a national regatta, but he couldn’t get them made in time. So he bought fabric and taught himself to make sails on his own.

When Jim won second place in the regatta, fellow sailors inquired about making their own sails too. So Jim and Connie published the “Sailmaker’s Library,” a series of five books that each detailed a singular type of sail. (Jim wrote and printed the series on his own A.B. Dick printing press.) The duo also wrote one-off newsletters about sailmaking and started selling supplies for the task, including sailcloth. In 1976, they launched a correspondence course on how to make sails from start to finish.

In 1969, Sailrite co-founder Jim Grant taught himself to make his own boat sails.


It nailed one product category before expanding to others.

After creating his curriculum for DIY sails, Jim identified a market for DIY canvas sewing, another skill of interest to sailors. In 1985, he wrote and self-published a book called “The Complete Canvasworker’s Guide.” A publisher eventually picked it up, and it’s still in print today.

Product offerings proliferated from there: Sailrite now sells over 7,000 products and DIY kits to help customers maintain and repair sailboats, powerboats, pontoons and even outdoor furniture. Customers can purchase fabrics, tools, hardware and more to complete projects like making a canvas cover for their boat or a tote bag for the beach. Corresponding how-to videos on YouTube show customers how to use the kits and products they’ve purchased.

Sailrite beat many other retailers to the e-commerce punch.

When Jim and Connie retired in 2004, their son Matt Grant took over the family business with his wife Hallie. As Sailrite’s current vice president, Matt credits much of the brand’s growth to the fact that it launched an e-commerce site before most other retailers.

Matt and Hallie began working at Sailrite in the late ‘80s. By 1997, most sales were coming from catalogs and mailers, and Hallie urged the family to create a website for Sailrite to expand its customer base. The Grants paid a web developer $20,000 to build Sailrite.com as the company’s online presence. About a year later, they listed their entire catalog--then several hundred items--online.

“The internet was fairly new [at the time],” Matt recalled. “We spent a lot of time on our website, and I remember looking at Walmart’s website to get ideas.”

Sailrite's site sells some 7,000 materials and tools for sailmaking.


Its YouTube channel is core to its brand.

Around the same time, Matt and Hallie began producing videos to help customers use the DIY kits they’d purchased online. They hosted their videos using a web browser plug-in called Silverlight--many viewers expressed their appreciation, but sales didn’t grow significantly as a result of the media.

By 2010, Sailrite had a large volume of videos running on Silverlight. Hallie thought YouTube--which had launched five years earlier--would make a better home for the brand’s video library.

“Eric [Matt’s brother] and I were trying to convince Matt about YouTube,” she recalled. “And I remember thinking we just need to jump on that bandwagon.”

She launched Sailrite’s YouTube channel, which now includes more than 1,700 videos covering everything from boat flooring application to upholstering outdoor furniture to sail repair. Video descriptions spell out every tool needed and step required, and they provide links to corresponding supplies on the Sailrite site.

Sailrite's YouTube videos show customers how to use its products to make sailboat accessories.

The videos stream for free and are designed to drive sales, said Matt.

“We do it so you can start from the beginning and complete a project, buy into the lifestyle, buy a sewing machine and our supplies,” he said.

“We [make our YouTube videos] so you can ... buy into the lifestyle, buy a sewing machine and our supplies.”


The channel has more than 48 million video views in total and gets between 25,000 and 30,000 new views every day. The Sailrite team estimates the channel brings 60,000 visitors to the site annually.

The videos, along with an expanded product offering and tech advances like Sailrite’s website, have contributed to 10 percent year-over-year growth for the last 15 years, Matt said.

Sailrite’s team started a spin-off business that did not go well.

For all their success, the Grants have weathered a few storms. At one point, they started a separate e-commerce business called Fabric Geek. The site offered offered inexpensive fabric “that didn’t follow our normal model of customer service and high-quality products,” said Matt.

“We wasted a very large amount of money to discover we just can’t manage a low-service entity,” he added. “Margins were set way too low since the idea was price over service. It just was a bad concept from a group that has always concentrated on service and product quality.”


The Grants invested $1 million in getting Fabric Geek off the ground with a top-of-the-line website and software. However, their “million-dollar idea didn’t work out” because the cost of customer acquisition was too high, Matt said.

“We also invested too much too quickly,” he added. “I think success is partially due to the grind. It almost felt like we tried to skip the hard work and just thought the customers would be there.”

“I think success is partially due to the grind. It almost felt like we tried to skip the hard work and just thought the customers would be there.”


Matt said Hallie helped him realize Sailrite was the right business model to stick with and that it was okay to pull the plug on the new project. Fabric Geek folded in 2016, two years after the project started.

The company has been family-run for 50 years, providing priceless leadership lessons.

Both family and individuality are core to Sailrite’s leadership dynamic. Each family member has taken ownership of a separate corner of the business ever since Matt and Hallie started working side-by-side with Matt’s parents 30 years ago.

Back then, “The four of us ran the business together,” said Matt. “The dynamic worked well because we all managed our separate areas of the business, which allowed us to really bring our unique approach and knowledge to the table for the company.”

Matt and Hallie maintain the same dynamic with their current team of about 65 employees, which includes their children.

“We each found something we fell in love with to put our own mark into,” said their son Zach, who’s been working on Sailrite’s product development for five years. “It’s a choice that makes you want to follow through, because it’s yours.”

“We each found something we fell in love with to put our own mark into. It’s a choice that makes you want to follow through, because it’s yours.”


Zach’s brother Tanner oversees the website’s Google Ads and search engine optimization (SEO) strategy.

“I started in customer service, and I’ve been given more responsibility here,” Tanner said. “It’s about trying to take things off of [my parents’] plates and become a key factor to help grow the business.”

Sailrite's related team members include (from L to R) Eric, Seth, Matt and Tanner Grant.


As in many successful multi-generational businesses, there’s no preferential treatment for family members at Sailrite.

“Coming in as a Grant, you’re almost perceived to be knowledgeable from the first day, but that’s not always the case,” said Zach. “One of the things that makes us so successful is when we are brought into the business as a third-gen employee, we have to learn everything from the ground up.”

Testing--of products and processes--is central to Sailrite’s strategy.

The Sailrite team prioritizes testing. It has meetings in which everyone is invited to present new ideas for the group to vote on.

“When we make a big decision, like how to ship a product, we like to test it out and make sure there are no errors,” Tanner said. “We give it a chance and go from there.”

Successful tests have led to the creation of branded upholstery lines and the invention of new tools for canvas sewing. They’ve also led to registered trademarks including the SnapRite System, a set of accessories for rivet guns, and patents including Sailrite’s Posi-Pin Clutching System for sewing machines.

Sailrite holds many patents for sailmaking accessories, including the Posi-Pin Clutching System.


And it always keeps an eye on the horizon.

Constant innovation is the goal at Sailrite, Hallie said. In 2019, the brand will continue focusing on its outdoor furniture line: It recently partnered with fabrics company Sunbrella on a collection of indoor-outdoor furniture fabrics, and more is on the way.

“We made smart and lucky decisions, but we also don’t rest on our laurels,” Hallie said. “We look for the next thing. For example, we sell a lot of fabrics, so now we are mapping fabrics on furniture so you can see what you’re getting before you order it.”

“We made smart and lucky decisions, but we also don’t rest on our laurels.”


No matter what comes next, the Grant’s future will continue to be a family affair. If Matt and Hallie’s careers are any indication, their children--and maybe even their children’s children--will be in business for a long time.

“I like coming to work because it’s my family,” said Matt.

Sounds like smooth sailing.

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