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How Matt Overcame Fear To Make Over $250,000 Annually

It took a while and a few bumps along the way for Matt Ainsworth to finally get on the road to success as a digital marketing agency owner.

Despite launching his New Orleans-based company, Giving Tree Media in 2015, in the immediate years that followed he couldn’t convert his passion for marketing into a full-time occupation. Ainsworth says he struggled to recruit clients and lacked the confidence to bill them for the actual value of his services.

So Ainsworth initially took a less direct route by designing and optimizing websites for small and medium businesses (SMB) between other jobs like selling photos at local markets and showing tourists the city’s famed French Quarter.

Opportunity came knocking unexpectedly when the pandemic hit and shut down much of the small business economy, including most of his own sidelines. Out of necessity, Ainsworth invested all his time into Giving Tree Media, an agency that specializes in search engine optimization (SEO) and online marketing.

After hitting US$10,000 in monthly recurring revenue during 2020, Ainsworth’s agency now earns double that amount, and word is quickly spreading in the local community about the quality of Giving Tree Media’s website design and SEO services.

Below, is a condensed version of a recent Vendasta interview with Ainsworth where he talks about:


  • What got him interested in marketing
  • How he overcame challenges along his journey
  • The reporting tool he uses when dealing with SMBs
  • Advice for current and aspiring agency owners seeking similar success


Watch the recorded video and read the edited Q&A below.

Edited Q&A


Giving Tree Media Founder Matt Ainsworth

What got you interested in digital marketing?

My dad was a software entrepreneur, so when I was eight, nine and 10 years old I attended business meetings with him and we built custom databases for companies in small towns.

It’s different from what I do now, but just seeing my dad talk to business owners inspired me to make digital marketing my career. It gives me a way to help entrepreneurs be successful.

How did the pandemic affect your livelihood and business?

They say it takes a long time to become an overnight success. For me, that’s definitely true. If I take a step back to before 2020, I was struggling to make Giving Tree Media a viable and profitable business for about five years.

I was a freelance web developer; I went door-to-door asking for business but I didn’t have the confidence to ask for much money for my services. To make ends meet I had several side hustles such as conducting private history tours in New Orleans. I also sold photography at a local art market.

Because of the pandemic those side hustles stopped, so I was forced to face my fears head-on and devote all of my time to making Giving Tree Media successful.

What services does your agency provide?

My overarching mission is to help local business owners get found organically online, so to that end, I currently offer two services to help them achieve that.

The first is website revamps, which entails ensuring that an SMB’s website works properly and loads quickly.

The other is local SEO. So that’s all about making sure SMBs are found, for example, in the top three Google Maps listings and top five organic positions within Google search engine results pages (SERP) because that’s what most people see when they search. That’s what generates website clicks, phone calls, and revenue for SMBs.

More recently I’ve also started looking at opportunities in digital advertising and social media management.

How did you become the trusted local expert in these services?

People come to you naturally by you being serious about what you're doing. To me, it's kind of like a game. Maybe you want to compare it to chess or poker, but it's the same idea.

“If you're going to be considered an expert, then have a passion for it. It's definitely a fun thing, and it helps people generate more money, which in turn makes you money.”

I devoted a lot of my time to reading books and attending workshops so that I could hone my skills in the services I offer.

Let’s move on to the ups and downs you faced during your journey to success. What were the biggest challenges?

I’d say there are or were three major challenges.

Firstly, lacking confidence. I was stopping myself from believing that I could succeed and charge the right amount of money for my services.

Secondly, finding the right clients. After overcoming the confidence block, the problem then becomes finding SMBs who are the right fit for Giving Tree Media.

Thirdly, capacity issues. This is a recent challenge and it’s one of those good problems to have. I’m doing well on the revenue side, but I spend a lot of time doing the work for clients, on administrative tasks, and dealing with business owners. I’m a one-man band and that makes it tough to find time to onboard prospects that are knocking on my door.

How did you overcome the issues of confidence and finding the right clients?

The first step was creating validity for my business with a proper website and feeling competent in discussing the specific services I’m offering. The other thing is you really have to understand business owners and how they think. A lot of them, especially in Louisiana, are very alpha-driven. They expect results. They expect them fast. If you can't do it, you're out the door.

"That’s why it’s important to create a process where you can deliver measurable results. That will give you confidence to talk to anyone you want. It will improve your perceptions around budgets and how much is needed to deliver outcomes SMBs are seeking."

Can you share how your business is performing financially?

As I said it takes a long time to become an overnight success. It was in 2020 that I hit US$10,000 a month in recurring revenue, and that’s increased to more than US$20,000 a month. Add all that up and it’s over US$250,000 a year.

So is it a case of success begets success?

Absolutely. Once you build your confidence, become an expert in what you're doing and win your first major client, it then becomes easier to convert more leads and grow revenue. I’m confident I can increase my revenue much more, but it comes back to that challenge of working out the best way to grow with limited capacity for Giving Tree Media; optimizing my processes, and potentially building a team so that I can serve more clients.

You’re a Vendasta partner. Can you tell me about the one tool in our platform that’s important to you when dealing with your clients?

I partnered with Vendasta in 2020 and that gave me validity. They helped me build my website and injected me with the confidence I needed. Having access to my dedicated sales representative was invaluable.

The platform itself has a lot of great tools. There are three essential tools I use, but the one I’d like to highlight is Snapshot Report. It gives my agency the validity it needs as it all appears under my Giving Tree Media brand. If you can describe what’s in the Snapshot Report to business owners then you’re off to a good start.

Editor Note: Vendasta’s Snapshot Report is a personalized report that provides insights into an SMB’s online marketing performance to competitors in the industry. It allows agencies to show business owners their strengths and weaknesses in areas such as SEO, website quality and social media.

You’ve had a very impressive turnaround, Matt. What advice can you give agency owners and marketers struggling to find success?

If I can start off with a comment on the overall industry first, a lot of people say that marketing has a bad reputation, which is not true overall. It’s an easy area to get in but it’s hard to produce results. So if you’re going to run an agency then you really have to enjoy it and be passionate about marketing.

My other advice is to be kind to yourself. Running your own agency can be stressful and business owners will give you grief. Maybe you're not getting any clients. It can take a long time. So definitely be kind to yourself, remind yourself that you're an entrepreneur, and there's nothing that can stop you.

I wasted a lot of time dreaming about what it's going to be like when I get to the destination that I want, have 20 clients, and can afford to do this and that. Don’t waste your time fantasizing. Instead, work hard and focus on your clients. And once you produce good results for them, the good word will spread.


Running an agency isn’t easy and there are many challenges to overcome before becoming successful.


  • Be confident in yourself and the value of what you deliver 
  • Enjoy what you do and continuously hone your technical marketing and soft skills so you can have quality conversations with SMBs
  • Be patient - success takes time

About the Author

Vishal Teckchandani is a Content Marketing Specialist at Vendasta. A newcomer to Canada, he spent the last 14 years of his career in Australia as a financial services reporter and TV host. He has written extensively about how technology companies are transforming business processes and lives, and interviewed the CEOs of global banking, payments, SAAS, and cloud storage providers including Afterpay, ELMO Software, Macquarie Group, National Australia Bank, NextDC, and Zip Co. When he’s not creating content, Vishal loves to cook, explore Saskatchewan with his family, and volunteer for his community.

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