Matt Diamante: From Playing in a Band to Building a Thriving Marketing Agency
Success isnât always a straight pathâitâs often full of unexpected turns. Matt Diamante, founder of HeyTony, didnât start his career dreaming of SEO, marketing, or running an agency. In fact, his early passion was playing in a band.
That passion led him to study advertising in college, which eventually turned into a journey of corporate jobs, quitting, freelancing, launching a website with investors, another job, quitting again, and finally starting his own business.
In this episode of Direct Or Detour, Matt shares his real journey, filled with pivots, risks, and lessons learned along the way.
Matt’s Unexpected Journey: From Music to Marketing
Playing in a Band & Finding a Way Into Advertising
Before he ever touched digital marketing, Matt was in a band during the early 2000s. He loved music and wanted to figure out a way to convince his parents to support the bandâs efforts. His solution? Go to school for advertising.
His reasoning was simple: if he could learn marketing, branding, and website design, he could use those skills to promote the band and build its audience. But while studying advertising in college, he found himself drawn to SEO (Search Engine Optimization).
SEO felt like a puzzleâa challenge where all the pieces had to fit together just right. And as his band fizzled out, his interest in digital marketing only grew stronger.
The First Corporate Job & Realizing It Wasnât for Him
After college, Matt took the traditional route and landed a job in advertising. He moved from Windsor, Ontario, to Toronto, stepping into a larger world of big agencies, big clients, and rigid corporate structures.
At first, it seemed excitingâhe worked on huge brands like KFC, Pizza Hut, Taco Bell, Honda, and Acura. But quickly, he realized the reality of big agency life wasnât what he expected. The creative process was slow, bureaucratic, and frustrating.
He spent hours just to create a single Facebook post, only to have it go through endless rounds of approvals. The rigid rules and lack of flexibility killed his enthusiasm.
Quitting & Trying Something New
Matt decided to walk away from advertising completely. He quit his job and jumped into something completely differentâworking on indie film projects and driving trucks for commercial sets.
But even while on set, Matt always had his laptop in the truck, hotspotting his way into SEO and marketing side gigs. He wasnât done with the industryâjust done with the corporate version of it.
Launching a Website with Investorsâ& Learning Hard Lessons
Next, Matt convinced a few investors to back him and a small team in launching an online publication (blog) focused on alternative lifestylesâvan life, off-grid living, and breaking free from the 9-to-5.
Within five months, the site exploded, jumping from 30,000 monthly visitors to 4 million. But that success came with challenges:
- Their servers couldnât handle the traffic. When their content went viralâsometimes hitting the front page of Redditâtheir website would crash.
- They were spending tons of money on operations, while also relying on interns and junior staff to keep the site running.
- Matt wasnât getting paid. Instead, he was accumulating debt, living off credit cards, and holding onto âequityâ that wasnât paying the bills.
Eventually, the business faded away, and Matt was left needing stability.
Another JobâAnd Another Fast Exit
Feeling burnt out from entrepreneurial struggles, Matt decided to go back to a traditional jobâthis time on a six-week contract at a major agency.
It lasted two days before he knew: this wasnât for him.
Despite getting paid well, he found the work soul-sucking and uninspiring. On day two, he was already planning his exit, calling up friends and booking a two-month trip to LA and Alberta to reset.
He burned through his savings during those two months, came home to Toronto, and had just enough for one more month of rent.
Freelancing & The Accidental Agency
With no backup plan, Matt landed a freelance client who gave him just enough income to cover his expenses. He took on every role imaginableâwriting blog posts, running ads, managing websites, email marketing, and social media.
The experience was invaluableâhe learned on the job, filling gaps in his knowledge and refining his skills.
As word spread, more clients started coming in. Soon, Matt was working 12-14 hours a day, overwhelmed with projects. His girlfriend (now wife) finally told him:
đŹ âYou need to either get rid of clients or hire someone.â
Not wanting to give up the income, he hired his first employee, a terrifying but necessary step. From there, the agency grew organically, fueled by word-of-mouth, referrals, and results-driven work.
HeyTony: Building His Own Marketing Agency
What started as Matt taking on freelance clients eventually became HeyTony, a full-service digital marketing agency focused on SEO and social media growth.
Today, HeyTony has a team of 13+ people and continues to grow. But the journey to get there was anything but predictable. It was built through:
- Trying different thingsâcorporate jobs, film work, launching a blog, freelancing.
- Taking risksâquitting without a plan, working on passion projects, and betting on himself.
- Learning on the flyâfiguring things out as problems came up, from server crashes to marketing funnels.
- Realizing he needed helpâmoving from solo freelancing to hiring and building a team.
Key Takeaways from Mattâs Journey
- â Not every path is a straight line. Success often comes from trying, failing, pivoting, and trying again.
- â Traditional jobs arenât for everyone. If the corporate world isnât for you, there are other ways to make it work.
- â Entrepreneurship is a learning process. Sometimes, the best education is just figuring things out as you go.
- â Hiring your first employee is scaryâbut necessary. You canât scale alone.
- â Betting on yourself can pay off. It might take time, but choosing your own path leads to the most fulfilling success.
Listen to the Full Episode
Mattâs story isnât about overnight successâitâs about taking risks, making mistakes, and finding the right path through trial and error.
đ Listen now: https://player.captivate.fm/episode/7a01e7cb-ae64-439c-8c44-91c9237cb0da/
Connect with Matt Diamante & HeyTony
đ Follow Matt for more insights & marketing tips:
đ Website: heytony.ca
đą Instagram: @heytony.agency
đ LinkedIn: HeyTony
đ Interested in being a guest on the show? Connect on PodMatch:
đ https://www.podmatch.com/hostdetailpreview/directordetour
đ #DirectOrDetour #Entrepreneurship #CareerJourney #Podcast
