Mastering Business with Technology: Insights from Jamie Gilleland

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Welcome back to the Daily Mastermind. This is your daily dose of inspiration, motivation, and education.

I’m joined by an amazing guest today. This interview is going to be a little different—we’re going to dig into some strategies as well as background. I want to introduce you to Jamie and give you a little bit of her background before we dive in.

She’s a world-class business leader—a speaker, coach, and elite business development expert. Jamie has two decades of experience driving business innovation. She’s been the co-founder of Market Area Real Estate Services Franchise, one of Market Magazine’s Top 100 Franchise Concepts.

Between her elite knowledge of Infusionsoft (now Keap) and her ability to partner with industry giants, she has a wealth of expertise. Currently, she’s the CEO of Riff Social, helping clients harness the power of automation and social media ads for sales and marketing. Jamie, I’m thrilled to have you here today.

I am doing marvelous. Thank you so much for having me. I love what you’re doing with this podcast and how you’re helping people. I’m honored to be here.

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The Journey to Business and Marketing

I know we’ve crossed paths over the years, and it’s clear to me that you know your stuff when it comes to business. For those who might not know your background, what got you into the business and marketing world? Were you always an entrepreneur, or did you gradually find your way into it?

I gradually got into it. I started out in the late eighties, early nineties—yeah, I’ve been around for a while. Actually, prior to that, I got my bachelor’s degree in Information Technology, which today would be called programming.

And I earned my master’s degree in Marketing.

That’s an incredible combination.

I always tease, if Al Gore invented the internet, I invented digital marketing.

There you go. Well, that’s amazing. Let’s talk about your early career. What were you doing before starting your own business?

Before the internet even existed, I was in Washington, DC, selling hardware and software. I sold IBMs and Compaq computers to government contractors. We called them the Beltway Bandits.

I was handling deals worth $2 million, $5 million for 386s, 486s, and Compaq portables. Remember those massive machines?

Oh, I remember them! We’re so spoiled now with the computers we carry in our pockets. So, you had a successful career, but at what point did you decide to start your own business? What led to that transition?

After 9/11, I was in the DC area, and my daughter’s school started planning for potential attacks. They were asking for supplies to quarantine the kids in case of emergencies. I thought, “No way. I want out of this rat race.”

We moved to Hilton Head, South Carolina, and I began consulting. That’s when I met a gentleman who had started Market Area Real Estate Services—a unique real estate concept.

He brought me on as a consultant and later made me COO, and eventually, CEO of the franchise corporation. I wrote the franchise documents, built the business, and we even had a $3 million IPO on Wall Street.

But in January 2007, I was diagnosed with a massive brain tumor. I had to step away from the business for six months to focus on my health.

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Overcoming Challenges

Wow. That must have been an incredibly difficult time. How did you process that diagnosis? You were on a successful trajectory, and then suddenly, your life changed. What was your mindset during that period?

The doctor told me I had less than six months to live. My daughter was ten, and my twins were six. I said to the doctor, “I have kids. I’m not abandoning them. That’s not an option. What are my choices?”

He told me surgery was my only option, but with the size of my tumor, I had less than a 20% chance of surviving. He suggested I get my affairs in order and enjoy my last months.

I looked at him and said, “Nope. I’ll take option C.”

Option C? What do you mean by that?

He said, “There is no option C.” And I replied, “Sure there is. You’re going to do the surgery, I’m going to survive, and I’m going to see my kids grow up and get married.”

One of my twins got married last March.

That is absolutely inspiring. It sounds like you created your own path forward when the odds were stacked against you. I imagine that experience shaped your approach to business and life. Did that situation lead you to focus on systems and automation?

Absolutely. When I had to step away from the business, even though I’d written the franchise manual, we hadn’t put systems in place for running the corporate headquarters. It was 2007, and real estate was crashing. The business failed while I was out.

That experience got me laser-focused on creating systems and automating processes. I wanted to build a business that supported my life—not the other way around.

That’s such a powerful insight. Most people build their lives around their businesses, but you flipped the script. So, is that when you started diving into automation and eventually worked with Infusionsoft (now Keap)?

Yes, exactly. I started in web design and building systems. Infusionsoft kept trying to recruit me to promote their product, but at the time, it was $400 a month. I thought, “My small-business clients won’t spend that.”

One day, I sat down with someone from their team, saw what it could do, and realized it made sense. I built my own system first, so I could start going to soccer games, take vacations, and enjoy holidays without stressing over deadlines.

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Selling Results, Not Products

It sounds like that was a turning point for you. You started creating systems not just for yourself but also for your clients. What did you find was the biggest struggle for entrepreneurs when it came to adopting automation tools like Keap?

One of the founders of Keap, Scott Martineau, once interviewed me after I became one of their top salespeople. He asked, “How do you sell Keap?”

I looked at him and said, “Scott, I don’t sell Keap.” His face dropped—he probably thought, “Why am I interviewing her?”

Then I explained, “I sell the results they get with Keap.”

That’s brilliant. Selling the result instead of the product itself—it’s such a simple yet powerful shift.

Exactly. People don’t buy products; they buy outcomes. They don’t care if it’s Keap, Salesforce, or something else. As long as it delivers the result they’re looking for, that’s what matters.

That’s a great philosophy. Let’s pivot to what you’re doing now. You’ve had incredible success with automation and Keap, but you’ve recently taken on the role of CEO at Riff Social. What led you to make that move?

I’ve always focused on email marketing, funnels, and content creation, but I stayed away from paid social media ads because they were complicated, expensive, and often didn’t deliver results.

When I met Bill Hillestad, Riff Social’s visionary founder, he showed me how we could use automation and AI to make social media ads accessible and effective.

We help businesses get thousands of real views on their content for a fixed monthly price—no surprise charges, no wasted ad spend. It’s about using the tools to build authority and reach the right audience.

That sounds incredible. Many entrepreneurs struggle with organic reach or navigating paid ads. How does Riff Social bridge that gap?

We use AI in conjunction with Meta’s algorithm to find the perfect audience. Instead of telling Facebook who we think should see your content, we let the content itself attract the right people.

We run two types of ads for every post:

1. Video Validation Ads – These drive 5,000–10,000 views to your post immediately, building credibility and authority.
2. Targeted Ads – These show your post to the ideal audience, ensuring you’re reaching people who are likely to engage.

When someone engages with your post—whether they watch, like, comment, or share—we tag them as part of your audience. Then, we retarget them with future posts, keeping your brand in front of them consistently.

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Building Authority Through Consistency

That’s such a smart strategy—focusing on validation and targeting. How quickly can businesses start seeing results with Riff Social? Is it a long-term process like traditional organic growth?

Not at all. From the moment you sign up, your first post will start getting 5,000–10,000 real views. It’s immediate.

Of course, building trust and authority takes multiple touches. In today’s noisy market, you need 15–30 interactions to really connect with your audience. That’s why we retarget engaged users, ensuring they see your content consistently.

For example, if you’re a real estate agent, someone might not be ready to buy a house today. But after seeing your posts over several weeks, they’ll remember you when they—or someone they know—needs your services.

It sounds like video plays a big role in your strategy. Why is video so important?

Video content generates more engagement than static posts. When people see a video with thousands of views, it validates your authority and makes them more likely to watch.

For instance, if you see a video with only two views, you might scroll past it. But if it has 5,000 views, you think, “This must be important.”

By using our system, your posts gain immediate credibility, and that drives more engagement from your target audience.

This approach seems like a game changer for small businesses. Many entrepreneurs struggle with time and resources. How does automation help them overcome these challenges?

Automation is essential for freeing up your time and ensuring consistency. Most business owners are so busy running their businesses that they don’t have time to manage social media effectively.

With Riff Social, you just create your content, and we handle the rest. We automate the ads, audience targeting, and retargeting so you can focus on what you do best—running your business.

For someone new to social media marketing, where should they start? Should they focus on creating content, learning about ads, or diving straight into automation?

The first step is to start creating content. Focus on sharing videos that showcase your expertise or tell your story. Don’t overthink it—just start.

Once you’ve got a few posts, schedule a call with us. We’ll help you build a strategy and show you how Riff Social can amplify your reach.

We also offer free weekly training sessions where you can learn the basics and get tips from our team.

That’s incredibly helpful. I know you mentioned a special offer for our listeners. Can you share more about that?

Absolutely! If you’ve already been posting, especially videos, we’ll run a free campaign for one of your posts. We’ll drive 5,000–10,000 views so you can see the power of Riff Social in action.

Afterward, we can discuss how to incorporate this strategy into your overall marketing plan.

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Final Thoughts

That’s such a generous offer, Jamie. Before we wrap up, do you have any final advice for our listeners?

Consistency is key. Whether it’s your health, your business, or building an audience, progress comes from showing up consistently and taking small steps every day.

As Bill Hillestad likes to say, “Shut up and post. We’ll take care of the rest.”

Jamie, thank you so much for joining us today. Your insights have been invaluable, and I know our listeners will get so much value from this episode. For everyone tuning in, don’t miss out on this opportunity to transform your business. Check out the show notes for links to Riff Social and Jamie’s free campaign offer.

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About Jamie Gilleland:

Jamie Gilleland is a seasoned entrepreneur, renowned speaker, and business strategist with over two decades of experience in business innovation and development. As the CEO of Riff Social, she specializes in helping businesses harness the power of automation and social media advertising to drive growth and scale operations efficiently.

Jamie's impressive track record includes co-founding top franchise concepts, leading IPOs, and mastering cutting-edge marketing technologies like Keap (formerly Infusionsoft). Her passion lies in empowering entrepreneurs to create systems that enable them to focus on what matters most—building a business that supports their ideal lifestyle.

Jamie's journey is an inspiring testament to resilience, having overcome significant personal challenges, including a life-threatening health diagnosis, to achieve incredible professional success. Her mission is to help others achieve clarity, consistency, and authority in their industries.

When she’s not revolutionizing businesses, Jamie is dedicated to sharing her story, mentoring others, and staying ahead in the ever-evolving digital landscape.

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Guest Resources:

BOOK with JAMIE: CLICK HERE

Website: https://www.rifsocial.com/

Youtube: https://www.youtube.com/@rifsocial

Facebook: https://www.facebook.com/rif.social/

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