We recently connected with Cindy Gordon and have shared our conversation below.

Cindy, appreciate you joining us today. What was it like going from idea to execution? Can you share some of the backstory and some of the major steps or milestones?

Honestly, it all started as a hobby. I’ve always loved food and storytelling, so I started a food blog just for fun, somewhere to share recipes, tips, and the little moments that happen in the kitchen. At the time, I didn’t have a grand business plan, I just enjoyed creating content and connecting with others who loved cooking too.

But the more I blogged, the more I learned about SEO, content creation, building traffic, and even a bit about monetization. I didn’t realize it then, but I was slowly building a skill set that could become something much bigger.

One day, while scrolling through social media, I noticed how popular air fryer recipes were becoming. Everyone was talking about them, but when I looked deeper, I realized there weren’t many solid resources or blogs fully dedicated to that niche. That’s when it clicked: what if I took everything I had learned from my first blog and applied it to this rising trend?

That idea lit a fire in me. The next day, I started mapping out the concept for an air fryer-specific site. I researched domain names, checked what keywords people were searching for, and brainstormed how to organize the content in a way that would be really helpful for readers.

Over the next month, I bought the domain, set up the website, and started creating posts—recipe testing during the day and writing content at night. I had to figure out the tech side again from scratch, but this time I had a blueprint. I knew how to use what worked, and avoid what didn’t, from my first blog.

It wasn’t just about cooking anymore, it was about creating a sustainable online brand. Looking back, the transition from idea to execution wasn’t one big leap, it was a series of small, intentional steps. But each one brought me closer to building something I could grow, scale, and eventually turn into my full-time business.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

I’m the founder behind a collection of digital brands that started with a single food blog and grew into five websites running simultaneously, each with its own niche, audience, and content strategy. At one point, I was managing a team of 11 contractors, overseeing everything from content creation to SEO, marketing, and monetization. That experience taught me how to master time management, streamline systems, and maybe most importantly, how to stay motivated without burning out.

During that time, people kept asking me for help. Friends, fellow bloggers, and aspiring entrepreneurs would reach out with questions like how do you get started, how do you make it profitable, and how do you keep going when you’re overwhelmed. After successfully exiting (selling) four of those businesses, I made the decision to build the type of mentorship platform I wish I had when I was starting out.

My current business is focused on coaching and empowering female entrepreneurs, especially those navigating the online business space. Whether they’re just getting started or trying to scale, I help them go from scattered to structured by simplifying their strategy, clarifying their priorities, and building systems that support growth.

What I offer now includes 1:1 coaching, a digital membership that provides ongoing mentorship and accountability, and a growing suite of digital products and workshops. Everything is designed to make business feel doable, even in the middle of real life. My mission is to help women take action on their ideas, organize their thoughts into executable plans, and build businesses that truly support the lives they want to live.

What sets my work apart is that I’ve been in the trenches. I’ve started from scratch. I’ve worn every hat. I know what it feels like to second-guess yourself or stare at a to-do list that’s way too long. I combine mindset support with real-world strategy, and my clients tell me it’s that combination that makes the biggest difference for them.

What I’m most proud of is the ripple effect. Seeing women step into their business with confidence, build something they’re proud of, and know that they’re not doing it alone. My work isn’t about a flashy highlight reel. It’s about helping people get results, stay focused, and keep going when things get messy.

Can you talk to us about your experience with selling businesses?

Yes, I’ve sold four businesses—two through brokers and two privately. Each sale taught me something different, but the overall experience gave me a much deeper understanding of what it means to build a sellable business from day one.

The businesses I sold were all content-based websites that I had grown over time, each with its own niche audience, monetization strategy, and traffic systems in place. Selling through brokers provided a more structured process with clear valuations and a broader pool of buyers, which was helpful, especially when I was newer to the selling side. Private sales, on the other hand, allowed for more flexibility and direct communication, but required a lot more legwork in terms of contracts, negotiation, and due diligence.

Here are a few lessons I’d pass on to anyone hoping to sell their business one day:

Build with systems in mind. Buyers aren’t just buying your brand—they’re buying your processes. The more you can document, automate, and delegate, the more attractive your business becomes.

Diversify your income streams. Businesses with multiple revenue sources (ads, affiliates, products, services) are typically more appealing because they feel more stable and scalable.

Keep clean records. Accurate traffic analytics, financial documentation, and clear SOPs can make or break a deal. You want to make it easy for someone else to step in and understand exactly how the business runs.

Know your value. Understand how your business is appraised, but also trust your gut. Just because someone offers a certain price doesn’t mean you have to take it. If it doesn’t feel aligned, it’s okay to walk away.

Plan your exit early. Even if you have no plans to sell today, running your business like you could sell it tomorrow changes how you prioritize and grow. It helps you focus on long-term value instead of just short-term hustle.

Selling those businesses gave me the freedom and clarity to start something new and now I use everything I’ve learned to help other women build businesses they could sell if they wanted to, even if they don’t plan to.

Let’s move on to buying businesses – can you talk to us about your experience with business acquisitions?

Yes, I’ve purchased one business before an online content site that aligned really well with my skill set and existing portfolio. It was a private acquisition, meaning we didn’t go through a broker. That made the process more hands-on, but also more personal and flexible.

What made me interested in buying the site was its potential. It already had solid content and decent traffic, but I could see exactly where I could improve and scale it using the systems I’d developed from running my other sites. It felt like a strategic shortcut rather than starting from zero, I was stepping into something with a foundation already in place.

Since it was a private sale, I leaned heavily on my network. I had colleagues who had been through multiple acquisitions, and they were incredibly generous in sharing what to look out for, how to structure the deal, and what red flags to avoid. That’s one of my biggest tips for anyone considering a purchase: learn from and lean on your network. Their insight helped me move forward with confidence.

The acquisition process itself included reviewing analytics and income reports, clarifying content ownership, negotiating terms, and setting up a smooth transition period. I also made sure to get clear documentation of any SOPs that were already in place.

Overall, buying a business was a great way to expand without starting from scratch. It was a reminder that growth doesn’t always have to mean building sometimes it means acquiring and improving what’s already there.

Contact Info:

• Website: https://exclusivelycindy.com/
• Instagram: https://www.instagram.com/exclusivelycindy/
• Linkedin: https://www.linkedin.com/in/cindy-gordon/
• Youtube: https://www.youtube.com/@cindygordon
• Other: https://www.thrivein5podcast.com/