Overcoming Doubt and Struggle: Agency Owner Jack Pires Shares His Blueprint for Success

In 2017, a quarter-life crisis struck Jack Pires.

The New Jerseyan was deeply entrenched in a career within one of the most demanding industries – hospitality. Overwhelmed by relentless workdays, insurmountable expectations, and strained relationships, Pires sought an exit strategy.

“It was seven days a week; days and nights. I didn’t see the person who I had a relationship with at the time. I didn’t see my own family. And any time I had a time off – I would splurge and spend more than I should have. It was just exhausting,” Pires says.

“And looking back on it, I remember thinking, ‘I can’t be in the same situation at 35 that I’m in now’.”

Yearning for change, he endeavored to apply his sales, managerial, and creative prowess to industries promising a better work-life balance, but the attempts faltered – a blessing in disguise.

As Pires explains, “the universe works in mysterious ways” and opportunities arose that piqued his interest and passion for digital marketing.

“Marketing was becoming a hot trend. That started the process where I thought I could use my creative skills, connections and expertise to launch something new, and that led me down the road of starting a marketing agency,” he says.

In 2018, he established SocialJack Media, a flourishing agency that now generates over $2 million in revenue, houses a 13-member team, and is a pillar in the community that drives local businesses’ growth. And fun fact: Pires met his future wife, who he shares three children with, during the initial stages of his venture.

But Pires openly acknowledges that the path to reinvention wasn’t smooth sailing. There were moments when he felt close to giving up, yet he found the inner strength to persevere.

Catch the complete interview or continue reading for the written feature.

From zero to one: The struggle to find the first paying client

As many agency owners can attest, running your own marketing business is grueling.

Despite his enthusiasm, Pires faced a steep learning curve in understanding the marketing services he aimed to offer. Identifying gaps in the market, capitalizing on them, leveraging technology, and becoming a solo seller were just a few of the hurdles that lay ahead. All while he was still working at a restaurant to sustain an income to fund his agency and living expenses.

“I wanted to provide multiple services because I knew the pain from a management perspective of handling websites, social media, and digital ads separately. But there was no one-stop solution, no one to manage it all,” Pires says.

Yet recognizing a gap wasn’t the same as bridging it, even with his strong connections in the restaurant industry.

“I thought everyone in my space would want to do business with me. It didn’t work out that way and I needed someone to test my concept,” he explains.

Enter fate. After knocking on many local business owners’ doors, the person who became Pires’ initial marketing experiment was none other than Carol Pires, now his wife, and the owner of Glaminator Beauty Bar. Her small business was the perfect proving ground for shaping SocialJack’s go-to-market strategy.

After she agreed to becoming a test customer, their collaboration worked wonders.

“From just social media and reputation management, we were scaling and killing it. I remember in the first six months Carol made $20,000 more per month than she was making at the time, and now it’s at $70,000 monthly revenue and two locations. It changed her life and she ended up leaving the one-bedroom studio where she was living at the time,” Pires says.

“If it wasn’t for Carol giving me a chance, maybe things as an agency owner wouldn’t have gone well. So thank you, Carol, I love you!”


Subsequently, Pires secured his initial paying client after a connection referred him to a business that deals with commercial ticket disputes. To clinch the deal, he journeyed two hours to Pennsylvania for a face-to-face meeting with the company’s executives to pitch a $300 marketing package.

As he left their premises, Pires’ heart raced, and he immediately called Carol to share his excitement: “I got my first client! We did it! This is going to work.” The closure of Jack’s first deal — a $300 package —gave him a much-needed confidence boost to keep on his new journey.

From one to many: The challenge of scaling up

In the beginning, a handful of small accounts laid the foundation for a gradual expansion: from two to four, and from four to eight, growing progressively. By the end of SocialJack Media’s first year, the count stood at around 20 accounts and Pires quickly left his salaried job to fully commit to the role of an agency owner.

“I had 20 accounts and I asked myself, ‘Can I make it 40?’ And I did. I kept doubling, and a lot of the success came from word-of-mouth referrals. I never used my own agency’s money on digital ads back then,” Pires says.

As business boomed, the complexity of his clients’ and their needs grew. Juggling tasks such as prospecting, selling, billing, fulfillment, and client management became overwhelming. Recognizing the need for assistance, Pires decided to hire an experienced business development manager.

“The clients were evolving. I had to up our game, broaden our scope, and enhance our presentations. So, my first hire was Michelle Maldonado, who I recently promoted to chief growth strategist,” he says.

With his new recruit’s help, onboarding procedures were standardized, processes were streamlined and enhancements were implemented in pitch decks to eliminate the need for creating new presentations for every client, resulting in time savings.

How billing woes pushed Pires to the brink?

Despite learning the ropes of running an agency relatively quickly, and having an experienced hand at his side, Pires couldn’t help but feel “imposter syndrome” creep into the back of his mind.

“It’s a real thing. It hasn’t happened too much lately, but I remember in the first three years it almost felt like it was every other month,” he says.

Some of this self-doubt stemmed from the difficulty Pires encountered when it came to billing clients. “I didn’t have the right system in place for billing and this meant delays in receiving funds – it was causing me severe stress as I just couldn’t figure it out,” he says.

Pires admits financial management isn’t his strong suit. And while his clients didn’t have a problem paying him money, the issue was around sending invoices and timing payments so that SocialJack would receive revenue into its business bank account to offset recurring expenses that were due such as salaries and operating costs.

He tapped into his network of entrepreneurs, who offered valuable advice on how he could better deal with the financial aspect of running an agency.
“And this led to another pivotal moment where I needed to bring in the people who knew how to manage the finances. I knew that because I didn’t want to do it, and I knew I wasn’t good at it,” Pires says.

“Once there are too many accounts it becomes difficult to manage the finances yourself – so you need a system that automates payments, you need someone who understands it and can educate clients on the billing processes and is staying on top of the invoices.

“Getting that right took a huge weight off my back, and critically, what it did was let me get an accurate account of my agency’s profitability and cash flow and say make sure everything was okay on the financial front.”

For retainer billing, SocialJack has configured its billing arrangements so that all its clients pay at around the same time in the month. For project work, clients are billed 50% upfront and the balance at the completion of the project.

“And I would just advise, figure out that system that works for you and invest in a financial team, which is a must,” he says.

Learning to make tough decisions

Achieving success as an agency owner isn’t just about seizing opportunities; it also involves making tough choices, whether things are going well or otherwise.

Early this year for instance, Pires identified an opportunity to expand into automotive industry marketing, but this niche required more focus on account management and creativity rather than copywriting, which his agency had invested heavily in from a talent perspective.

“We were spending a lot on copywriting. A significant part of our monthly budget was going there. We wanted to break into the automotive space, which looked promising. But this field needed more account management and creativity,” he says.

“So, I needed to grow our creative division and allocate more resources there, which was a tough decision. We had to reallocate resources from one area to hire more staff for another – it was certainly a challenge having that conversation, but I need to make that tough call.”

“We recently hired two new creative positions to help us with our automotive accounts and it’s paying dividends as we expected.”

While he handled the situation as tactfully as he could, Pires admits that it was one of the hardest business decisions he made, but one that’s inevitable as an agency scales and recalibrates to capture market opportunities.

Golden principles for success

As Pires reflects on his remarkable journey, he offers a set of fundamental principles to inspire aspiring entrepreneurs venturing into the agency world, or seeking direction for greater success.

Craft a vision statement

Every agency requires a guiding vision statement to steer its client-focused endeavors. For SocialJack Media, this vision revolves around “growth and inspiring connections” for local businesses owners.

“We are here to empower local business owners. Not just from a business perspective, but also from a mindset perspective and also connecting them to the resources and people they need to succeed,” he says.

Choose your approach: Swiss Army Knife or niches

In an era where many agencies specialize in specific industries, Pires emphasizes that a broader, generalist approach can thrive when supported by a versatile team capable of swiftly grasping the intricacies of diverse client needs.

“For us, versatility is key. I envision us as a Swiss Army knife,” he says. Pires firmly believes in offering solutions tailored to each client’s unique challenges, underlining the importance of having talent who can adapt quickly.

Invest in person-to-person relationships

Strong relationships can make or break an agency, and owners who invest the effort in meeting real people have an edge.

“Person-to-person relationships: invest in that. Whether it’s yourself, hiring the right account management team, building those relationships, that’s gold. That will lead to tremendous success,” he says.


A key part of this is meeting prospects and clients in person and at events, such as local chambers of commerce and industry events.

“And then being able to communicate properly with those clients and then execute on the results that you said you would deliver,” he says.

Embrace innovation and technology

In the fast-paced world of agencies, Pires acknowledges the paramount significance of innovation and technology. “I can’t stress enough the importance of technology, innovation, and leveraging the data available today,” he says.

“For us Vendasta is a key partner, not just from a tech stack perspective, but the playbooks they create that we can leverage for our agency and in our sales process.”

Be willing to experiment and fail fast

Pires stresses the importance of being adaptable when things aren’t working. Whether it’s big changes like billing systems or smaller tasks like refining pitch decks, the key is the same.

“As I worked on pitch decks, I watched how clients used them,” Pires says. “If it worked, great. If not, I’d adjust and try something new. At the start, it was about experimenting and learning.”

Where to next for Jack?

In navigating the journey of starting and scaling an agency, Pires’ story is a testament to his grit and determination.

As the inevitable question surfaces—was the formidable journey of agency inception justified?—Pires contemplates his accomplishments: a thriving enterprise fostering local employment, clients’ resounding success, and the foundation of his own family. He responds resolutely.

“I wouldn’t change a thing. It’s been a blessing—a tremendous one. Supporting my young family, cherishing moments with loved ones, and living my passion—it’s all been incredibly fulfilling. This journey of rediscovery and self-discovery, I urge everyone to embrace,” he asserts.

However, he candidly acknowledges that in hindsight, embarking on this path earlier could have yielded advantages. “Looking back, I recognize the value of early self-discovery and guidance. Assessing life’s core values, passions, and purpose could have streamlined the business model, enhancing competitiveness. Nevertheless, the process I’m undertaking now carries its own merits,” he says.

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