Jamie Rossi | American Entrepreneur

I Created A Six-Figure Digital Marketing Agency

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Business

Jamie Rossi

Founder, Jamie Rossi | American Entrepreneur

$100K

revenue/mo

Founders

Employees

Jamie Rossi | Ame...

jamierossi.com

from Columbus, OH, USA

started November 2021

$100,000

revenue/mo

Founders

Employees

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Want more updates on Jamie Rossi | American Entrepreneur ? Check out these stories:

Who are you and what business did you start?

I started my career in financial services, but I quickly realized there were no consistent, high-quality marketing solutions for financial professionals. Most companies only sold cold leads, which meant spending hours on the phone getting hung up on. I hated it.

Since I couldn’t find a solution, I decided to learn the marketing game myself to generate leads for my own practice. But one thing led to another, and soon other agents in my office were asking me to help them book appointments too. That’s how The Appointment Setter was born—an appointment-setting service built specifically for financial professionals.

What makes us different? We don’t just sell leads. We put qualified, high-intent appointments directly on our clients’ calendars, so they can focus on closing deals instead of chasing prospects. The service is so valuable that, to this day, we haven’t spent a dollar on paid advertising—our entire growth has been through word of mouth.

Today, we book over a thousand appointments per week and consistently generate multi six-figure months.

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How do you come up with the idea for Jamie Rossi | American Entrepreneur ?

I knew this was the right idea because my only other option was to go back to working for someone else—and that was never going to happen.

At the time, I realized that other agents in the financial services industry were struggling with the same problem, especially during COVID. The industry had always relied on in-person meetings, but the shift to virtual made appointment setting more critical than ever. There was a massive gap in the market, and I knew I could fill it.

I’ve always had an entrepreneurial mindset, even back in my days as a Marine. On weekends, I would go to garage sales around the military base and flip items on eBay, running no-reserve auctions before PayPal or Gary V-style flipping was even a thing.

But this venture was different. It solved a real problem, provided massive value, and was highly scalable. It wasn’t just another hustle—it was a business that could grow exponentially while helping financial professionals focus on what they do best.

How did you build the initial version of Jamie Rossi | American Entrepreneur ?

– Cold Email & Retargeting

I started with a simple approach: cold email marketing. I created a lead database, pulled lists of financial advisors, and set up an email outreach system to start conversations.

Once people engaged with the emails, I used retargeting ads on Facebook and Google. This multi-channel approach ensured that even if someone ignored the email, they’d still see our ads later, driving more bookings.

– Automating the Process

To streamline everything, I built a simple but powerful booking flow: Cold email outreach → Funnels prospects into a lead form Social media retargeting (Meta & Google) → Keeps them engaged Booking page (Calendly routing form) → Automatically schedules appointments Email & SMS follow-ups → Ensures show-up rates Follow up to collect GMB feedback.

I didn’t start with a huge budget. My biggest investment was time, figuring out what worked. Initial costs: • Email software & domain setup – <$100 • Ad spend for retargeting – Around $500 to test • Calendly & automation tools – <$50/month

Tools used: • GoHighLevel (CRM & automation) • Calendly (scheduling system) • Google Sheets (lead and appointment tracking) • Meta & Google Ads (for retargeting & audience building) • Zapier (automations)

The first version of this system only took a few days to build. But it took several months to iterate and start to get decent results.

Starting out on this journey I didn't consider it work. It was like a game that I was in control of. It was a lot of fun to implement things and watch them work (or not). The best part is I didnt need a bit team to do it. Initially I built everything out myself and eventually hired some support staff to run the day to day.

How did you launch Jamie Rossi | American Entrepreneur and get initial traction?

The business didn’t start with a formal launch—I was simply booking appointments for myself, but I ended up with more than I could handle. So, I started handing off extra appointments to other agents in my office.

Once those agents started closing deals from my appointments, word spread fast. Their upline noticed, and before long, demand grew across the industry.

By month three, we hit $30K in revenue, and by month seven, we had already crossed $200K.

I definitely didn’t build this to scale from the start. In the beginning, it was basically a patched-together system that could route appointments, but it wasn’t fully optimized. Over time, I figured out how to scale properly, learning what’s important, what’s not, what’s essential, and what’s just noise.

What was the growth strategy for Jamie Rossi | American Entrepreneur and how did you scale?

While our first-year revenue numbers set the foundation, our real growth has come from understanding exactly what our customers need and delivering it better than anyone else. Instead of just focusing on raw numbers, we’ve refined our processes, systems, and customer experience, which has led to strong client retention and referrals.

We occasionally incentivize referrals when we have extra inventory to sell, but for the most part, growth has come organically through word of mouth and consistent high-value delivery. The system has evolved over time, and below is Version 2 of the booking system that I implemented in the second year to streamline operations even further.

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What were the biggest lessons learned from building Jamie Rossi | American Entrepreneur ?

One of the biggest mistakes I see people make when starting out is getting caught up in the little things—the website, the domain name, the perfect logo, business cards. Those things matter eventually, but they’re nowhere near as important as people think. You can always change them later. Focusing too much on these details stalls progress and keeps people from ever getting started.

Persistence is key. It may be cliche but you have to stick with it, even when things don’t go as planned. (and they wont go as you planned) Finding good people to work with and building strong partnerships can double or even triple your business in a very short time. The right team and relationships can make or break you.

Another major lesson: listen to your customers. Having a solid feedback loop is critical. You don’t have to implement every request, but if you actually pay attention to what people are asking for, you’ll always find ways to improve and grow.

At the end of the day, I approach business like a game—I stay lighthearted and adaptable. Taking things too seriously kills creativity, and frankly, it’s just no fun.

Jamie Rossi | American Entrepreneur Acquisition: How much did Jamie Rossi | American Entrepreneur sell for and what was the acquisition price?

No exit! Still running the day to day .

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More about Jamie Rossi | American Entrepreneur :

Who is the owner of Jamie Rossi | American Entrepreneur ?

Jamie Rossi is the founder of Jamie Rossi | American Entrepreneur .

When did Jamie Rossi start Jamie Rossi | American Entrepreneur ?

2021

How much money has Jamie Rossi made from Jamie Rossi | American Entrepreneur ?

Jamie Rossi started the business in 2021, and currently makes an average of $1.2M/year.