Cindy Gordon built five websites, grew a team of 11, and created businesses that could keep running while she traveled. Then, while they were still making money, she sold four of them.
When I asked Cindy Gordon whether people questioned her decision to sell her businesses, she laughed a little and said, “No one really understood.”
I mean…of course they didn’t.
At one point, Cindy was running five websites with a team of 11. One of her Facebook communities had grown to more than 900,000 people, and she had documented the businesses well enough that she could travel for weeks and mostly monitor things from afar.
People around her kept asking why she would sell instead of simply letting the team continue running everything.
“The businesses were making money. Her team could run them. And she still wanted out.”
That’s where I got curious.
It’s easy to understand changing direction when something is obviously falling apart. What happens when the thing you built actually works and you’re still ready to be done with it?
It started with a food blog she didn’t plan to turn into a business
Cindy started Vegetarian Mama in 2009. Her family was vegetarian, so people were always asking what they ate. Then her second son was born in 2010 and developed food allergies, which shifted the site toward gluten-free, dairy-free and nut-free recipes too.
She’d be standing in Whole Foods or Kroger trying to figure out whether something was safe for her son, sometimes calling the company directly. Her thought was basically, if I’m doing this, another mom probably is too. So she started sharing what she found.
There was no big business plan behind it.
Then brands started reaching out. At first they sent products. Later, they paid her to try products and develop recipes, and the hobby started turning into something else.
Cindy told me she didn’t even realize how much money could be made in that kind of business until she found other women in the blogging world who were a few steps ahead of her. She could see what they were doing and what was possible.
That part matters to me because if you don’t know people are making real money from a food blog, why would that even enter your list of options?
Sometimes seeing the example comes first.
The first website took years. The second one moved fast.
Cindy left her job as a special education administrator in 2010 after having her second son. Her husband traveled a lot, she had two young boys, one with a lot of medical appointments, and her job was with an online school where problems could come up at all hours.
She described that season as being a “full-time unpaid mom” while building the website.
Vegetarian Mama took about three or four years before Cindy felt like it was making decent money. Then she built an air fryer website.
By that point, she knew SEO. She knew how to research what people were searching for, how to spot a gap and how to create content that could meet that demand.
The air fryer site started making significant money within a couple of months.
She wasn’t guessing the way she had been with the first website. She was using everything she’d spent years figuring out.
That becomes important later.
Somehow we got to five websites
Over time, Cindy built four food websites and an Ohio travel site. All five were running at the same time.
And because I am me, I needed to know what her actual LIFE looked like while all of this was happening.
Five websites, 11 people, two kids, a husband…girl, when are you sleeping?
Cindy said sometimes she looks back and isn’t exactly sure how she managed it either.
But she was organized.
Very organized.
She built SOPs and checklists. Everything lived in Asana, the team communicated through Slack, and people knew what they were responsible for. There was also crossover between the brands, so the five businesses weren’t operating as five completely separate worlds.
Her business manager eventually took over much of the day-to-day team management, and the way Cindy found her is kind of wild.
When the Facebook group connected to her air fryer business started growing quickly, Cindy asked for volunteer moderators. One of those volunteers turned out to be really good. Her responsibilities grew, Cindy started paying her, and eventually she became Cindy’s business manager and right-hand person.
She lived in Spain, which actually worked beautifully because of the time difference. Cindy could wake up to work that had already been completed, review it and keep things moving.
At a certain point, Cindy had built businesses that didn’t require her to sit there all day. She could travel for weeks. She could spend more time with her family. She could step away.
So again…
Why sell?
She was getting more interested in other people’s businesses
While Cindy was running her websites, people started coming to her with questions. How are you getting this traffic? What are you doing with SEO? How did you build that? Can you help me figure this out?
And she liked it.
She liked looking at somebody else’s business and figuring out what they could change. Meanwhile, running her own sites had started feeling repetitive. The businesses still made money, but Cindy wasn’t getting the same enjoyment from the work anymore.
Eventually she had to admit it.
“This is not fully what I want to do anymore.”
She already had plans to eventually sell the businesses.
Then her business manager suddenly died.
Cindy had been traveling for about three weeks, and the two of them were supposed to catch up on Monday. Her business manager died on Sunday.
She wasn’t only someone Cindy relied on professionally. They had become close. And she was Cindy’s same age.
Cindy had planned to wait about another year before selling. After her friend died, she started asking herself why she was waiting. Why was this future date somehow the correct date?
So she moved the exits up.
The businesses were still making money
At their highest-income periods, Cindy estimates about 90 percent of the revenue came from advertising.
Earlier on, much more of the money came from brand work. Companies would pay her to create recipes and content featuring their products, but eventually she stopped doing most of that.
And I understood why immediately.
Freelancing, which is my world, can create the exact same problem.
“You leave a job because you don’t want one boss, then somehow look up and realize you have five.”
Cindy owned the business, but a brand could still come back asking for changes. There were approvals. There were deadlines. There were still people she had to answer to.
She wanted a different setup, so she leaned much more heavily into advertising revenue. She also created recipe ebooks, and the air fryer website had a membership where people could pay to remove ads and get access to additional recipes.
By then, these weren’t little hobby blogs. They were revenue-producing assets someone else could buy.
Which meant selling them was its own whole thing.
Selling a business was another skill she had to figure out
Cindy sold two of the businesses through brokers and two through private sales.
For the first larger sale, she wanted the broker’s network and access to buyers. Then came the meetings, where potential buyers went through the business looking for anything they could use to question the valuation.
Cindy compared it to buying a house and immediately pointing out that the roof needs replacing.
Except now imagine sitting in a Zoom call while people pick apart a business YOU built because they’re trying to negotiate the price down.
Fun.
She said some of those early meetings were intimidating. She knew the business better than anyone there, but she still found herself leaning heavily on the broker.
She also noticed that many of the brokers and acquisition people in those rooms were men. There were moments when she felt like she didn’t have a seat at her own table.
Eventually, she got more comfortable. She learned how those conversations worked and what buyers were looking for. Once she understood the process better, she was able to handle one of the smaller sales privately.
She had learned another business skill she didn’t have when she started Vegetarian Mama.
Then she bought somebody else’s website
This might be one of my favorite parts of the whole conversation.
Cindy eventually bought an existing online business. She could look at the website and immediately see findability problems she had already spent years solving in her own businesses.
So she bought it, fixed things, improved the site and started making money from it.
Selling it quickly was not part of the plan.
Then someone heard Cindy had been selling businesses and reached out asking if she’d sell this one too. Cindy gave her a price, but the woman didn’t think the current revenue justified it.
Cindy wasn’t worried about it. She knew what she thought the site could do, so she kept working.
She redesigned the website, updated things behind the scenes and continued improving the business. A couple months later, the buyer came back.
This time she paid Cindy’s original asking price in cash.
Cindy had owned the website for 11 months.
And all I could think was…look at how far we’ve gotten from “I started a food blog because people kept asking what vegetarians eat.”
By this point, Cindy could look at an existing website and see problems and opportunities she wouldn’t have known to look for when she started.
That experience didn’t disappear because she was ready to do something else.
She sold the websites. The skills came with her.
Today Cindy runs Exclusively Cindy, where she helps business owners get found online by humans, algorithms and AI.
It sounds like a very different business from running food blogs, until you look at what she had actually spent all those years learning.
SEO. Audience building. Messaging. Systems. Hiring. Looking at a website and figuring out what isn’t working. Understanding how traffic turns into money. Learning what makes an online asset valuable enough for somebody else to want to buy it.
She wasn’t starting with an empty toolbox.
“She sold the websites. She didn’t sell what she knew how to do.”
And I think that’s one of the more interesting parts of changing direction after you’ve been doing something for a long time.
The thing you built can end. You still know what you know.
So…why sell something that works?
Cindy said people in her industry really didn’t understand.
Why not keep the businesses? Why not let the team run them? Why walk away from something profitable?
By then, Cindy wasn’t trying to rescue a failing business. She had built businesses sustainable enough that other people wanted to buy them.
Her interest had moved.
She was more excited by the problems people brought her than she was by continuing to run the sites. She had already planned to sell eventually, and losing her friend made her question why she was treating some future date as the moment she was allowed to do it.
Near the end of our conversation, I asked what she would tell the Cindy who started that first hobby blog.
She said she’d tell her it all worked out bigger and better than she could have imagined.
Then she said:
“Don’t be afraid to take bold moves and shoot your shot.”
Which was very convenient considering I had literally told my husband that morning that I thought I’d been playing some of my own goals too safe.
So…cool.
Apparently I invited Cindy onto my podcast to interview her and got called out in the process. Lol.
The part I keep thinking about, though, is that Cindy didn’t need the businesses to become a disaster before she let herself be done with them.
They worked.
She wanted to know what else she could do.
Yeah. I get that…and I LOVE it.
Watch my full conversation with Cindy on She Chose Again:
CONNECT WITH CINDY
Website: https://exclusivelycindy.com/
Instagram: https://www.instagram.com/exclusivelycindy/
YouTube: https://www.youtube.com/@cindygordon
Cindy Gordon helps female entrepreneurs get found by humans, algorithms and AI. A 6x founder who has built six businesses and sold four, she holds a Masters in Special Education with a focus in Behavior Analysis and brings the discipline of individualized assessment to findability work. She has grown a brand’s following to a million, built a 900,000-person community and a 250,000-person email list, and led a global team of 11. Her work is the boring, specific part: getting painfully clear on what you stand for, your one sentence, and the exact words people are typing into ChatGPT, so you show up when someone asks who the expert is. Cindy is the founder of Exclusively Cindy and the host of The Strategic Entrepreneur podcast, where she explores findability, proof of human, and what it takes to become unmistakable.
Watch her full conversation with Elle Mills on She Chose Again, an Out of Edits interview series about what happens after women decide something needs to change.
