Growing an agency is very difficult, and you might feel unclear what to do next in order to grow and scale your agency. The Smart Agency Masterclass is a weekly podcast for agencies that are wanting to grow faster. We interview amazing guests from all over the world that have the experience of running successful businesses, and will provide you the insights you need. Our podcast is just over 3 years old, and have reached more than a half million listeners in 42 countries.
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What do you do when a business partnership fails? Do you try to engineer the perfect agreement so the exit is clean, or focus on alignment long before anyone signs anything? The truth is, most agency partnerships fail because owners rush into them without slowing down to see the cracks. Preparing for the worst is not pessimistic. It is how you protect the business you are trying to build.
Today's featured guest has gone through failed starts, broken agency partnerships, and overcommitting his time as the owner for fear of losing opportunities. He'll unpack 25 years of wins, mistakes, and hard earned clarity, from building his agency and how the biggest breakthroughs came from leadership shifts rather than marketing tactics.
Andy Crestodina is the co founder of Orbit Media, a Chicago based web development and optimization agency approaching its 25th year in business. Orbit has grown to a team of fifty five and more than eight million in annual revenue. Andy is also one of the most respected voices in content marketing, with millions of readers, hundreds of speaking engagements each year, and a reputation for teaching real strategy instead of recycled tactics.
In this episode, we'll discuss:
Slow, organic for consistent agency growth.
What a failed agency partnership can cost you.
The hire that gives an agency founder their time back.
E2M Solutions: Today's episode of the Smart Agency Masterclass is sponsored by E2M Solutions, a web design, and development agency that has provided white-label services for the past 10 years to agencies all over the world. Check out e2msolutions.com/smartagency and get 10% off for the first three months of service.
How Slow, Organic Growth Built a 25-Year Agency
Andy was working as an IT recruiter in the nineties and found himself bored at his day job. He didn't get to build anything in that position and he had a lot of ideation urging him to do something else. Luckily, the internet offered him that chance.
He could build a website and channel his creative energy through that side project. But could he do it full time? He had no resume and no portfolio to present to a potential employer. He realized it was easier to get a client to take a chance on him than it was to convince an employer to hire him.
So he and a high school friend started building sites. The first partnership failed fast and then the second attempt grew slowly, quietly, and steadily for 25 years. The secret was not paid ads or cold outreach. It was content. Consistent publishing, useful insights, and a commitment to organic channels long before that became mainstream advice.
When Agency Partnerships Go Wrong and What It Really Costs
There are many stories of successful partnerships in the agency world, but overall the disaster stories are much more common. As Jason says, you either know the bad partner or you are the bad partner. Andy lived through one of the toughest versions of that story.
He had three partners for a while. One of them ran an unprofitable department. Responsibilities were unclear. Values were not aligned. And when it came time to clean up the mess, a poorly written shareholder agreement became a bigger problem than the partner himself.
Andy had to mortgage his home and personally lend the company money to buy out the partner. The agreement used the wrong valuation formula. The partner dragged his feet and what should have been a difficult but clean process turned into a long, expensive, emotionally draining separation.
Looking back, Andy says something most founders never admit. A handshake would have been better than the shareholder agreement they had.
The real mistakes came earlier: saying yes to a partner who did not share the same values, not slowing down long enough to evaluate the deal, and being hungry for growth and ignoring misalignment.
The Leadership Hire That Gave the Founder His Time Back
Around this time of misalignment between partners was when a long time client turned management consultant stepped in. He saw tension inside the partner group, so he moved to do a 360 review and surfaced the problems that no one wanted to say out loud. Andy was quick to spot that he would be a great addition to the agency, and so eventually, he became the CEO.
That single hire changed everything.
Andy was doing all the sales and marketing. Meetings all day. Proposals all night. Burning energy on tasks someone else should have owned years earlier.
Once his new CEO came on board, he built systems, built a sales process, hired strategists to handle qualification and scoping. Suddenly Andy had 20 hours a week of his life back.
He poured that time into content and went right into work. He doubled publishing frequency, launched a conference, wrote a book, held monthly live events, shot videos. The brand exploded. Their reach multiplied. The inbound engine went from effective to unstoppable.
This is the founder shift so many agency owners avoid. Letting go. Delegating the work that drains you. Investing your best energy into the work that grows the company, not the work that maintains it.
Saying Yes, Saying No, and Protecting Your Energy
Andy admits he still overcommits. He still says yes to speaking engagements because he loves the stage and it generates leads, even though the constant travel wears him down.
This is something many agency owners have to face. You may want the brand, speaking gigs and reach. But you also want to protect your energy so you do not turn into the hero who disappoints people when they finally meet you.
At some point, you have to choose where your yes goes. Andy chose articles, newsletters, LinkedIn, webinars, a conference, and in person events. He let go of podcasting. He narrowed his focus so he could go deeper. That discipline, more than any tactic, is what keeps his inbound engine healthy 25 years later.
The Tension Between Culture and Profit
How do you balance loyalty to your team with the need for profit and EBITDA?
Andy is still trying to figure this out. His team has an average tenure of eight years. Some team members have been there twenty. Andy cares deeply about them and their families. But agencies face moments when bonuses, salaries, utilization, and capacity collide. Where doing right by people and doing right for the business feel like competing priorities.
There is no perfect answer. But there is a direction. Take care of your people first. Trust them to help you solve the profit problems. Fix leaks. Raise rates. Tighten scope. Operate like owners. And when the agency wins, let your team win with you.
Culture breaks agencies faster than anything else. Profit can be fixed. Culture cannot be patched over.
Do You Want to Transform Your Agency from a Liability to an Asset?
Looking to dig deeper into your agency's potential? Check out our Agency Blueprint. Designed for agency owners like you, our Agency Blueprint helps you uncover growth opportunities, tackle obstacles, and craft a customized blueprint for your agency's success.
When an Agency Merger Falls Apart: Lessons on Reinvention with Tom Snyder | Ep #864
What would you do if the merger you believed would change everything suddenly collapsed? Agency owners often dream of the big exit: the acquisition, the payday, the validation. But if you've been in this industry long enough, you know the story rarely goes as planned. Today's guest lived through the dot-com boom, a merger gone sideways, a rare "un-merger," and multiple reinventions across three decades.
Today's featured guest is an agency owner who lived through the dot com boom, a merger gone sideways, an unmerger (a rare event), and multiple reinventions over three decades. He'll talk about his journey and the lessons he's gained in resilience, clarity, and what it means to build a business that lasts.
Tom Snyder is the founder and CEO of Trivera, a Milwaukee-based agency that originally launched in 1996 under the name Website Solutions. He got his start back when tables ruled the web, Netscape Navigator was leading the browser war, and you had to explain to clients what the internet even was.
Tom's agency grew quickly through the dot com boom, became part of an early multi-agency rollup, unmerged after the dot com crash, and later rebuilt itself around strategic services, recurring revenue, and emerging technologies. Thirty years later, he has seen nearly every high and low this industry can deliver and has the scars and wisdom to match.
In this episode, we'll discuss:
The roll up that seemed like a dream and the subsequent meltdown.
Sponsors and Resources The Early Days of the Web: A Front Row Seat to Digital History Inside the Dot-Com Boom and the Rollup That Promised Millions When an Agency Merger Falls Apart How a Rare Un-Merge Saved the Agency How Adapting to New Technology Helped Survive in Crisis Letting Go of Comparison to Stay Focused on the Journey Do You Want to Transform Your Agency from a Liability to an Asset?
How to Build the Leadership Layer Your Agency Needs to Scale with Brandon Rost | Ep #855
Is your agency growing fast but still running without the right structure or leadership team to sustain that growth? If too many people are reporting directly to you, it's a clear sign you've outgrown your current setup. But building that next layer of leadership isn't as simple as promoting your top performers. Without a clear strategy, those well-intentioned promotions can backfire, causing confusion, turnover, and setbacks that stall your agency's momentum.
Today's featured guest learned that lesson firsthand. After experiencing a year of costly turnover caused by the wrong management moves, he came away with a better understanding of what real leadership development looks like. In this episode, he'll share what it takes to scale beyond seven figures, the mistakes that nearly derailed his agency's growth, and the key shifts that helped him build a stronger, more sustainable business.
Brandon Rost is the founder and CEO of be Marketing, a Pennsylvania-based advertising agency that helps brands grow through creative, digital, and media strategies. Over the past decade and a half, Brandon has built his agency from a solo operation into a multi-million-dollar powerhouse by focusing on relationships, resourcefulness, and relentless problem-solving.
He's proof that you don't need to have all the answers when you start, just the willingness to figure it out along the way.
In this episode, we'll discuss:
How to reinvest profits strategically to scale your agency sustainably.
Why promoting top performers doesn't already create effective leaders.
The KPI's and systems that improved profit and cash flow.
The mindset shift that turns fast growth into longterm success.
Subscribe Sponsors and Resources Why Being Resourceful Is the Key to Building an Agency Scaling Up: Investing Every Dollar Back In the Agency Learning to Lead and Let Go: Building a Leadership Team Knowing Your Numbers and Turning Chaos Into Profitability Sales: The Last Most Agency Owners Are Ready to Hang Up What Scaling Fast Taught Him About Patience and Culture Do You Want to Transform Your Agency from a Liability to an Asset?
#1 Thing an Effective Head of Operations Does for an Agency CEO with Jhana Li | Ep #765
Have you hit the limit of the growth you can single-handedly bring to your agency? What steps are you taking to ensure you continue to be your organization's MVP? For many agency owners, reaching hitting a glass ceiling on growth signals the need to bring on a skilled operator to help eliminate low-value tasks from their schedule.
Today's featured guest specializes in operations hiring and has developed a systematic approach to identifying and delegating low value tasks that consume CEOs' time and energy. As an expert in operational efficiency, she trains operators to create effective processes that free founders to focus on strategic growth. She shares her secret to a great hiring funnel, what results to expect from an operator's first 90 days in your agency, and the #1 thing an operator does for their agency founder. Learn actionable insights on breaking through operational bottlenecks and building a strong operational foundation through strategic hiring and training.
Jhana Li is a former COO and the founder of Spyglass Ops, an Operations Hiring Agency, working on behalf of digital businesses to find and hire operations positions. She discusses the challenges agency owners face when trying to scale their businesses and share insights on breaking through the common glass ceiling that many entrepreneurs encounter.
Jhana emphasizes that growth stagnation often occurs when founders reach their personal limits in creativity and productivity. She provides valuable strategies for developing new skill sets and building a capable team to propel business growth beyond personal capabilities.
In this episode, we'll discuss:
The secret to a great hiring funnel that attracts A-players.
The crucial first 90 days that determines an operator's success.
Subscribe Sponsors and Resources Scaling Your Agency Beyond the Founder's Glass Ceiling Do You Have a Hiring Funnel That Consistently Attracts A-Players? What's the Secret to a Great Hiring Funnel? The First 90 Days: A Guide to Integrating New Operators The #1 Thing an Operator Should Do for the CEO Do You Want to Transform Your Agency from a Liability to an Asset?
Empowering Your Agency Team: Creating a Clear Growth Path for Success with Warren Wilansky | Ep #764
Do your employees have a clear path for growth within your agency? Do they feel supported, empowered, and fulfilled in their role? Today's featured guest shares insights from his journey transforming his agency team structure that resulted in thriving for the business, his team, and himself.
After years of struggle, this agency CEO took ownership of his role and developed a strategic approach to employee motivation and development. By reimagining annual reviews and creating meaningful growth opportunities, he shifted from an environment of stagnation to one of continuous improvement. In this interview, learn the benefits of offering a clear path for growth within your agency, and how to improve your team's experience during annual reviews. He also shares how to get yourself out of sales — if that's something you want — and why you need to keep doing what you love.
Warren Wilansky is the president and founder of Plank, a Montreal-based digital agency specializing in arts and culture, nonprofit, and higher education projects. He shares his agency ownership journey and discusses the challenges of navigating the early days of the agency, including the learning curve of running a business and the evolution of his role as a sole owner.
In this episode, we'll discuss:
The mindset shift that allowed for team retention and growth.
Redefining employee reviews and how to have them review you.
Sponsors and Resources A Traditional Story of Accidental Agency Ownership A Mindset Shifts that Allows for Employee Retention and Growth Redefining Employee Reviews - and Having Them Review You Agency Sales: Freeing the Founder & Empowering the Team How to Maintain Purpose as Your Agency Grows Do You Want to Transform Your Agency from a Liability to an Asset?
Is It Time to Rebrand Your Agency? When, Why, and How to Rebrand with Jim Heininger | Ep #763
Is your agency in need of a rebrand? Many of us are accidental agency owners who threw together a brand without fully understanding our niche or service offering; starting with just a basic name and logo. As the agency evolves this may signal the need for a strategic brand refresh. Today's featured guest runs a rebranding agency and shares the scenarios that could justify a rebrand, the difference the right will name make for clients to differentiate you, and share some rebranding strategies to keep in mind.
Jim Heininger is a seasoned agency owner based in Chicago who runs two agencies: Dixon James, a strategic communication and change management firm, and the rebranding specialists known as the Rebranding Experts. With over 25 years of experience in the public relations industry, Jim discusses the importance of building a strong agency presence, why your name matters, and when is the right time to think about a rebrand.
Smart Pricing Table: Today's episode of the Smart Agency Masterclass is sponsored by Smart Pricing Table, an award-winning proposal software built just for marketing agencies and designed to handle your unique challenges and cut down the time you spend on proposal as much as 90%. Go to to see if this is the missing piece your agency needs. Schedule a demo and get .
What Does Brand Mean? 2 Big Reason to Consider an Agency Rebrand Why Names Matter for Brand Differentiation Things to Consider Before Renaming Your Agency Do You Want to Transform Your Agency from a Liability to an Asset?
Hiring an Agency COO and Balancing the CEO-COO Dynamic with Brittany Filori | Ep #762
Do you need to get yourself out of agency operations so you can work ON the agency rather than in it? Are you stuck in processes and fulfillment when you should be looking at growth? It might be time to hire for the role of COO to ensure your agency's success. A Chief Operating Officer plays a pivotal role in an agency's development, significantly reducing the CEO's operational burden. However, timing is crucial – agencies should carefully consider their growth stage before initiating the search for a COO, and thoroughly understand the position's complexities to ensure an ideal match.
Our featured guest brings a unique perspective to this discussion. Having served as both COO and now CEO at her current agency, she offers valuable insights into the essential qualities needed for the role. Her experience illuminates the delicate balance required between the visionary (CEO) and the executor (COO), demonstrating how this partnership can drive optimal agency outcomes.
Brittany Filori is the CEO of 51Blocks and several other white label agencies serving agency owners and entrepreneurs. She discusses the crucial role of a Chief Operating Officer (COO) in agency management and shares her unique journey from starting at the bottom to becoming a CEO, providing valuable insights into the relationship dynamics between CEOs and COOs.
Sponsors and Resources Should You Hire an Operations Manager or a COO? Strategic Operations Staffing for Growing Agencies 3 Most Important Roles of an Amazing COO The Dynamic Between the CEOs & COOs Preventing COO Burnout: Building a Sustainable Leadership Structure Do You Want to Transform Your Agency from a Liability to an Asset?
Successful AI - Human Collaboration: Where Technology and Creativity Intersect with Marc Beckman | Ep #761
Is artificial intelligence revolutionizing business operations or threatening the carefully crafted storytelling techniques developed over decades? As many businesses struggle with integrating AI while maintaining authentic connections, today's featured guest offers valuable insights from his perspective as both an agency leader and AI advocate as well as someone who can see some of the fatigue caused by the ever-growing demand for constant information that has been aided by AI and the availability to create content faster and efficiently. He shares the ways he is integrating AI technology into his own agency, and why he believes it won't work when it comes to replacing the human touch. Learn about his vision for AI use in business, the trends he sees changing in consumer preferences in social media, and how agencies can adapt to AI.
Marc Beckman is the co-founder and CEO of DMA United, a New York City agency specializing in style and design, with a broad reach into fashion, art, music, sports, and entertainment. He shares the pros and cons of building great relationships with company CMOs, his agency's challenges improving at self-promotion, and how he sees AI has affecting the very human art of storytelling.
In this episode, we'll discuss:
Building a reputation that attracts big brands.
The double-edged sword of CMO relationships.
AI integration done right; the framework agencies need.
Sponsors and Resources Building a Reputation That Attracts Big Brands Pros and Cons of Getting in Bed with a CMO AI Integration Done Right: A Strategic Framework for Agency Innovation Did AI Kill Storytelling? Do You Want to Transform Your Agency from a Liability to an Asset?
Maximizing Event Speaking: How to Generate Leads While Sharing Expertise with Dale Bertrand | Ep #760
Are you leveraging public speaking to grow your brand? Have you considered expanding your reach by having team members represent your company at events or interviews? Today's featured guest has transformed public speaking from a marketing tactic into a primary source of new business leads. In just three years, he went from getting most of his business from webinars to getting most of his leads from his speaking engagements.
In this episode, learn the common fears that keep agency owners from speaking at more events, the type of speaker you should be to attract more business, and why you should consider building a team willing to share their expertise and promote your agency at events or interviews.
Dale Bertrand is the founder of Fire & Spark, a Boston-based SEO agency with a team of 25. He shares his journey from being a software developer to diving into the world of digital marketing. He also shares about transforming his love for public speaking into a key agency tool to promote his business and getting new leads. With a busy schedule of 30 conferences annually, he shares how he built his speaking career and what lies ahead to keep the momentum going.
In this episode, we'll discuss:
Where to start in public speaking.
Should you give away your secrets? Why the "giver" speaker sees results.
Converting speaking engagements into business growth.
Sponsors and Resources How Public Speaking Transformed an Agency How to Easily Gain Confidence as a Speaker Why Being a Giver Delivers the Best Results Converting Speaking Engagements into Business Growth The Benefits of Sharing the Spotlight with Your Team Do You Want to Transform Your Agency from a Liability to an Asset?
Uncovering the Gold Mine in Your Agency's Email List with Reade Milner | Ep #759
Have you dedicated time to ensure the health of your email list? If you've built a 15,000-person email list for your business—that's a huge accomplishment! But what if that list isn't performing? If your open rates are as low, that number becomes meaningless. It's not about the quantity of subscribers, but the quality of your engagement. Moreover, if you're not consistently delivering valuable content that keeps you top-of-mind as a problem-solver, then you're not maximizing the potential of your list.
Today's featured guest shares his insights on effective email marketing strategies, including optimal content delivery frequency, list maintenance best practices, and how his agency has evolved over the past decade. Drawing from his experience, he advocates for email marketing as a reliable channel that doesn't depend on unpredictable social media algorithms. He believes many companies are overlooking a gold mine by fixating on new client acquisition while neglecting their existing client base.
Reade Milner is the co-owner of Rogue Pine, a digital marketing agency focused on the middle of the funnel and email marketing. Reade shares his journey into the world of digital marketing and discusses why many agencies are actually sitting on a gold mine when they're searching for new clients. Reade also shares how often you should be sending value content to your lists, and more.
In this episode, we'll discuss:
Why most agencies are sitting on a gold mine.
How to build a newsletter people will actually want to read.
Sponsors and Resources How Real-World Experience Shaped a Marketing Career Why Most Marketing Agencies Are Sitting on a Gold Mine 3 Key Sections to Build Newsletters People Actually Want to Read Why 40% is the New Standard for Email Open Rates The Power of Direct: Why You Shouldn't Overlook the Impact of Email Do You Want to Transform Your Agency from a Liability to an Asset?
This episode is brought to you by Wix Studio: If you're leveling up your team and your client experience, your site builder should keep up too. That's why successful agencies use Wix Studio — built to adapt the way your agency does: AI-powered site mapping, responsive design, flexible workflows, and scalable CMS tools so you spend less on plugins and more on growth. Ready to design faster and smarter? Go to wix.com/studio to get started.
Tom got into websites before most people even understood what a web browser was. He recalls visiting a friend in 1995 who showed him a website for a local jeweler. The fact that someone in Milwaukee could suddenly sell jewelry to anyone in the world blew his mind. That spark soon became Website Solutions, a one-man shop in his duplex basement that grew into a million-dollar agency within three years.
These early days were defined by scrappiness. There were no WordPress installs, no Mailchimp, no Shopify. Agencies wrote their own CMS platforms, email tools, and ecommerce systems.
For years, Trivera worked on project-based engagements. Sell a website. Build it. Launch it. Then hunt for the next one. It created a revenue roller coaster that made it hard to grow.
Once they shifted the model, everything changed. Retainers gave them predictable cash flow, stability during downturns, and the ability to build deeper, longer-term partnerships.
By the late nineties, agency rollups were happening everywhere. Big groups on the West Coast were buying smaller shops at high valuations, promising stock payouts that would multiply as the group grew. Tom's agency was acquired by one of these rollups. The offer was attractive: $1 million in stock with the expectation that it could balloon into ten million within a couple of years.
For Tom, this was more than a payday. It felt like a way to secure better opportunities for his team. Higher salaries, better benefits, more resources. All the things agency owners often think a larger parent company can provide.
But as the ink dried on the deal, the dot com crash hit. Internal battles erupted among the agency owners inside the rollup. Some wanted to scale fast and sell. Others were emotionally attached to their agencies and resisted change. As the economy collapsed, so did the plan.
Tom describes the internal environment as chaos. Agencies within the rollup started blaming one another for the downturn. Some owners viewed Tom's Midwest operation as a weak link and argued it was a mistake to acquire them.
Then came the breaking point. At a Las Vegas meeting that was supposed to chart a path forward, Tom learned that he would lose control of his agency. His wife, who served as CFO, would be dismissed. His team would report to another agency owner.
This happened on September 10th.
The next morning, as they sat in their hotel room trying to process what to do, the news broke that planes had hit the World Trade Center. The world changed, and so did their priorities. In that moment of clarity, they made the decision to walk away and unmerge.
Unmerging from an agency rollup almost never happens. But because the rollup was already fracturing, the leadership was surprisingly open to it. They returned most of the shares, let Tom keep a small portion, and released the original agency name. From there, Tom and his wife rebuilt everything from scratch under a new identity.
Although it felt like the right decision to make, they were still exiting what was still a financially stable operation to start from scratch, which was a scary but necessary step to take. They brainstormed names that felt Greek or Latin until they arrived at Trivera. The name itself was available only because the previous owner had just let the domain lapse. It felt like a small sign that starting over was the right move.
This reset allowed Tom to build the agency the right way. No irrational exuberance, burn rates, or pressure to sell. Just strong culture, smart financial discipline, and an eye on durable business fundamentals.
After the dot com crash, new technologies created fresh opportunities. SEO, email marketing, mobile, and social opened new revenue streams that helped Trivera rebound each time the economy dipped. Tom noticed a pattern. Every downturn was followed by a brand new marketing wave that rewarded the agencies willing to embrace it early.
One of the most pivotal moments came during the 2009 recession. The agency had lost clients, payroll was tight, and they needed a breakthrough. Everyone was asking about social media at the time, so Tom and his team built an event called Social Media University. They hustled for two months and ended up selling 400 tickets. The sales and sponsorship revenue kept their payroll alive and catapulted them into a new service category.
Events like this do more than create revenue. They cement authority, give an agency a story in the market, and in Tom's case, it opened doors to new clients and positioned them for the next evolution of the agency.
Despite the wins, Tom admits there were years he compared his agency to others and wondered why they scaled or sold faster, especially some that got the tools from his very social media event. It is easy to feel behind when you see competitors raising money, getting acquired, or shouting big revenue numbers.
However, there's very little one can actually know about other agency's purchase deals. These stories are incomplete. You never know what the real terms were. You never know the headaches behind the scenes. And you definitely never know if they actually took money home.
Success in the agency world is rarely a straight line. It is more often a messy, winding path filled with reinventions, hard conversations, and moments when you question everything. So agency owners struggling and watching others reach new milestones should remind themselves that longevity comes from resilience, not a perfect upward curve.
Looking to dig deeper into your agency's potential? Check out our Agency Blueprint. Designed for agency owners like you, our Agency Blueprint helps you uncover growth opportunities, tackle obstacles, and craft a customized blueprint for your agency's success.
E2M Solutions: Today's episode of the Smart Agency Masterclass is sponsored by E2M Solutions, a web design, and development agency that has provided white-label services for the past 10 years to agencies all over the world. Check out e2msolutions.com/smartagency and get 10% off for the first three months of service.
Brandon didn't plan on running an agency. At the time, he was managing social media for a corporate job and bartending on the side when a PR firm owner offered him a shot at managing her clients' social accounts. What started as ten small accounts quickly snowballed into a full-time business.
Like most early-stage entrepreneurs, he had no idea what he was doing at first. He sent invoices in Word documents, figured out HR and finance on the fly, and said "yes" to every opportunity—then learned how to deliver later. It wasn't glamorous, but it worked.
That resourcefulness became his superpower. As anyone who has grown a business can tell you, success comes from resourcefulness - not knowing everything. You don't have to know everything right now. Just figure it out and make it work.
For the first few years, Brandon kept bartending to cover his bills and put every dollar the agency made back into growth. That discipline gave him the runway to build a real company without debt or short-term panic.
He hired his first part-time employee within a year, went full-time around year two, and hit seven figures by year four in 2014. However, crossing the million-dollar mark didn't come with confetti and fireworks. It came with more responsibility, more moving parts, and a steeper learning curve.
"Everyone thinks hitting a million feels different," Brandon said. "It doesn't. It just brings on more work." Instead of waiting for that milestone to magically change things, focus on building the right foundation so the business can continue to grow without you doing everything. Make it a point to continue to delegate part of that workload every quarter, and after a couple of years, you'll find you've gotten your freedom back.
It was the right moment to create different positions that would oversee different departments. However, his strategy was flawed at first; "We elevated people just to elevate them," he said. "And it set us back a year." He never stopped to ask whether or not those employees were ready or even suited for management roles. As a result, they dealt with a year of turnover followed by slowly getting back on track.
The lesson for Brandon was: put the right people in the right seats, and don't assume your best technician wants to—or should—manage others. Leadership isn't a promotion; it's a whole new role.
Once the business hit its stride, Brandon turned his focus to profitability. He shared how the agency once got caught in a dangerous cash flow loop of collecting Google ad payments for clients and effectively becoming a bank instead of a marketing firm.
After untangling that, his team started tracking key KPIs more closely:
AGI (Agency Gross Income) in the 55–60% range
Net profit around 10–12%
Payroll around 33% of AGI
By simplifying operations and separating client media costs from agency revenue, they stabilized cash flow and built a healthier margin. Simply put, what you measure improves and, for Brandon, that meant finally treating the numbers as a steering wheel instead of a rearview mirror.
Even after 15 years, Brandon still handles most of the sales himself. It's something he admits he should've delegated earlier, but building a sales team isn't as easy as hiring a "radio guy" and hoping they sell.
After two failed attempts, Brandon realized the problem wasn't the salespeople but rather the lack of systems. Now, the new plan is to support the team with brand marketing, create a "sales tackle box" full of proven client stories, and build repeatable processes for outreach, follow-up, and closing.
You'll always be the best salesperson until you document what's in your head. With the right structure and stories in place, a sales team can finally scale what made the founder successful in the first place.
Looking back, Brandon said the biggest surprise was how much patience real growth takes—and how easy it is to lose sight of culture while scaling fast. Whether it was figuring out HR policies, managing team dynamics, or setting boundaries for office events, every new level came with a new layer of learning.
He now focuses on balance: growing deliberately, empowering leaders, and making sure the culture that got them here doesn't get lost along the way. "We've learned to grow smarter, not faster," he said.
Looking to dig deeper into your agency's potential? Check out our Agency Blueprint. Designed for agency owners like you, our Agency Blueprint helps you uncover growth opportunities, tackle obstacles, and craft a customized blueprint for your agency's success.
Smart Pricing Table: Today's episode of the Smart Agency Masterclass is sponsored by Smart Pricing Table, an award-winning proposal software built just for marketing agencies and designed to handle your unique challenges and cut down the time you spend on proposal as much as 90%. Go to smartpricingtable.com/smartagency to see if this is the missing piece your agency needs. Schedule a demo and get 50% OFF for the first two months.
As a former COO, Jhana has seen the glass ceiling many founders encounter at some point in their growth occurs once they've hit the limit of the growth they can personally create. It's no longer about showing up and single-handedly working out every problem or how innovative they can be. Breaking through that glass ceiling requires both personal transformation and strategic team building.
The path forward demands founders step back from their hands-on approach and focus on developing a trusted leadership structure. This includes establishing middle management positions across all functional departments, ensuring each area has dedicated decision-makers and strategic thinkers. Central to this evolution is hiring an operations manager who can unify the team and create organizational cohesion, transforming disparate departments into a synchronized whole.
For Jhana, hiring A-players is not about fishing in the right pond but rather using the right fishing rod. Great talent is available everywhere but does your agency have a hiring funnel that will consistently extract the right A-players for the right role?
A strategically designed hiring funnel serves as both an attractor and a filter, automatically screening out 95% to 98% of applicants before they reach the interview stage. This efficiency comes from carefully crafted criteria that not only draw in ideal candidates but also discourage those who wouldn't be a good fit, saving valuable time and resources.
This approach contrasts sharply with the common scarcity-driven hiring mindset, where employers cast wide nets and hesitate to filter out any candidates. According to Jhana, a well-structured hiring system achieves better results by focusing on quality over quantity, ultimately leading to conversations with only the most promising 3% of candidates who truly align with the role requirements.
Building mousetraps in your job post and hiring process is one thing – for instance, Jhana and her team add a codeword to the job description that they'll ask the candidate to repeat during the job application process. However, she only uses that type of strategy for roles that require a high level of attention to detail.
Other than that, she has a secret weapon that has consistently given her the best results: performing a skill assessment before sending a candidate to interviews. Skill assessments can take up to two hours, which is exactly the point. It's a way to stress test the candidate to see if they already have the experience for the role. Jhana likes to include very specific questions to get candidates to think about how they would tackle a major challenge associated with that role, which experienced candidates will have no problem doing.
Moreover, the effort a candidate puts into completing a skill assessment can be telling. A candidate who submits a thorough, well-structured response demonstrates a commitment to excellence and an understanding of the expectations of the role. In contrast, a lackluster submission may indicate a lack of motivation or a superficial understanding of the job requirements.
Candidates who have genuine experience in a given area will articulate their thoughts with clarity and assurance, while those who are less familiar may struggle to provide coherent answers. By designing assessments that require candidates to draw on their past experiences, you can better identify those who are truly equipped to handle the challenges of the role.
Jhana has learned that an experienced operator will take their first 30 days with a company to observe, learn, and listen before they jump in and start fixing things. They understand that what they see at first glance might not be the root cause issue at play. Therefore, if they jump in and start tacking inefficiencies right away they might be missing the actual issue.
From a founder's perspective, it may be frustrating, as they expect immediate results. However, it is essential for operators to familiarize themselves with the intricacies of the business to address the root causes of inefficiencies effectively.
To prevent these frustrations, Jhana recommends scheduling a "success meeting" at the second-week mark. By that time, your operator will have had two weeks to observe the inner workings of your agency. During this meeting, the operator presents their findings and aligns with the founder on priorities moving forward. The result of this meeting should be a clear understanding of what the operator is expected to accomplish within their first 90 days so the founder knows this is in fact the right person for the job.
How much time should you invest in training a COO? Jhana knows of cases where the founder is still training their ops manager six months later. To her, you should always keep in mind that any time spent on training is an investment on that person and they won't return on that investment until they are fully functional in their role. She prefers to do a 14-day boot camp before seeing ROI. During that time, she makes herself available every day for a minimum of 30 minutes so they can ask any questions or run something by her.
The most important thing an ops manager should be doing for their CEO is help optimize their time to maximize their contributions to the organization and ensure that they focus on high-value tasks that drive growth.
The CEO is supposed to be the agency's MVP and yet they constantly undervalue themselves when they spend time doing low-value tasks. This is why Jhana trains her operators to do a time audit on their CEO during their first 30 days in the organization. As a result, they can determine how much of the founder's time is going to low-value tasks and prepare a game plan to get them out of day-to-day operations.
Why not start now? Even if you're not at the point where you can hire an operator, do a time audit, locate the low-value tasks taking up too much of your time, and then delegate them to an assistant. That alone would make a huge difference in ensuring you're spending more time growing the business.
Looking to dig deeper into your agency's potential? Check out our Agency Blueprint. Designed for agency owners like you, our Agency Blueprint helps you uncover growth opportunities, tackle obstacles, and craft a customized blueprint for your agency's success.
E2M Solutions: Today's episode of the Smart Agency Masterclass is sponsored by E2M Solutions, a web design, and development agency that has provided white-label services for the past 10 years to agencies all over the world. Check out e2msolutions.com/smartagency and get 10% off for the first three months of service.
Warren's journey is a pretty traditional accidental agency owner story. Starting with a communications degree, he transitioned from freelance website design to founding an agency with two partners. However, the partnership proved unstable—one left after six months, and the other departed after five years, ultimately leaving Warren as the sole owner for years, until his first employee became his current partner.
Initially, Warren viewed his agency more as a collaborative collective among friends rather than a structured business. This perception shifted dramatically when his second partner departed, forcing him to fully embrace his role as a CEO. For the first time, he recognized the need to take complete responsibility for every aspect of the agency.
While continuing to engage in website design—his original passion—Warren realized that his most critical project was the company itself and its strategic development.
As he navigated the early stages of his agency, Warren quickly recognized the importance of hiring people who could outshine him in their respective roles. For instance, the agency hired its first creative director once he discovered someone who was a better designer than he'd ever be. This realization marked a turning point in his business strategy. Instead of attempting to be the best at every task, Warren embraced the idea that the success of his agency depended on assembling a team of skilled professionals who could bring their expertise to the table.
Another important milestone in his hiring structure was the introduction of director-level positions. Initially, Warren adopted a model where all team members were viewed as equals, believing this would promote collaboration and creativity. However, he soon realized that this lack of hierarchy left employees with limited opportunities for advancement. Without clear pathways to grow within the organization, talented individuals often felt stagnant, leading to disengagement and, ultimately, turnover.
A structured hierarchy with a path for career progression allows individuals who excelled in their roles to take on new challenges and responsibilities. It also serves as a chance for team members to figure out whether they liked the feeling of running a company, fostering a sense of ownership and accountability among team members.
Most employees have a love-hate relationship with the annual review. On the one hand, they fear the feedback but on the other they also await the meeting in order to discuss a raise. At Warren's agency, the team conducts annual and quarterly reviews for more regular check-ins.
Although they're still called "reviews" at Warren's agency, Jason's advice is to change the term to something that doesn't evoke feelings of judgment and scrutiny, redefining this process by labeling it as a "coaching session." This emphasizes the supportive nature of the interaction, framing it as an opportunity for development rather than an evaluation of past performance.
Overall, the biggest challenge is finding the right balance of positivity while still offering areas of improvement without demotivating employees in the process. As Warren points out, traditional reviews often begin with critiques, which can overshadow positive feedback. By reorienting the conversation to highlight accomplishments first, followed by constructive suggestions for improvement, employees are more likely to retain and act upon the feedback provided.
In addition to reviewing your team, as a CEO or founder you should also want to know your areas of improvement. It can be hard getting that information out of employees, who might feel intimidated. A good framing to get the information you want is to ask "What do you want me to start doing?" "What do you want me to keep doing?" and "What do you want me to stop doing?" In this way, you will get provide enough context for valuable insights without putting your team in the awkward position of formally reviewing you.
As CEO, Warren's current role is mostly looking for ways to support his strategy team, tapping into his network to bring more opportunities for the agency, and being the face of the agency. The CEO is also the person who has all the relationships and all the stories that shape an agency's identity and are a great tool to converting a new client.
Having all the stories can lead a CEO to believe no one could possibly replace them in sales, after all, only they have the necessary narratives to engage clients. However, then the agency would fall apart if the founder ever decided to retire. Instead, if you can share those stories with your team to use on different case scenarios, you will free up your time to focus on the agency's growth and empower your team to share their own client success stories.
In the end, are the stories from 10 or 20 years ago the only ones worth telling in your agency? For Warren, the stories being created today are just as important and even more so. Instead of romanticizing old stories, give your team the chance to use them to engage clients as they gain experience instead of just selling on features. Eventually, they'll have stories of their own and they will take full ownership of sales, which in turn will free you up as agency owner to dedicate to the business' growth.
As CEO you should do what you love and delegate or eliminate the things you don't. In Marc's case, he enjoys sales, which he views as relationship building rather than a transactional process. He advocates for founders to carefully distinguish between tasks they love and those they want to delegate.
Completely removing yourself from sales can lead to professional dissatisfaction, so Marc recommends creating processes flexible enough to allow strategic involvement. While the team should be capable of handling most sales independently, founders can still contribute by joining initial or final calls to add depth and personal connection.
Just be mindful of the things you hate doing and want to delegate and the things that really bring you joy and wish to keep doing. Only with that clarity you'll be able to prioritize and choose a path that won't kill your love of the work.
Looking to dig deeper into your agency's potential? Check out our Agency Blueprint. Designed for agency owners like you, our Agency Blueprint helps you uncover growth opportunities, tackle obstacles, and craft a customized blueprint for your agency's success.
Jim built his career in the agency environment, spending 25 years in public relations working for some major agencies like Bushman Hillard and Ketchum. Later on, he worked for McDonald's as a communications strategist tasked with helping them get through some brand issues they faced at the time. His time at McDonald's taught him a lot about the perspective on agencies and how to form great client relationships to get the best work out of your agency.
This time proved transformative for his career, it was when he had the opportunity to start his own agency and also when he started learning more about branding.
Jim defines a brand as the comprehensive collection of experiences and assets that define a company, extending far beyond visual elements like logos to encompass customer experience, brand promises, and their fulfillment.
While a brand ultimately exists in customers' minds, and you'll never be able to control how customers perceive it, you can influence that perception. Influential figures like Steve Jobs understood the importance of brand narratives and greatly admired Nike, which has mastered the art of branding by creating a strong identity that transcends their products.
Businesses should actively manage their brand perception rather than allowing external forces to dictate it. Hence, it is only logical they consider rebranding once the brand no longer represents their business.
According to Jim, agencies are the business category that most frequently undergo rebrands. It makes sense, given so many are accidental agencies. Many agency owners begin as skilled practitioners who establish a business in response to growing client demand, often resulting in a created brands that may not stand the test of time.
There are two common reasons why founders consider a rebrand:
Make it all about the business, instead of yourself. Many agencies initially build their brand around the founder's expertise. As the business grows, however, there's often a strategic need to highlight the broader team's capabilities, reducing client expectations for direct founder involvement in every project.
Niching down. Another common scenario prompting a rebrand is when an agency decides to niche down its services. While owners might worry about alienating existing clients through rebranding, Jim notes that clients typically focus more on service quality and results than brand aesthetics.
Rebranding is not merely a cosmetic change; it is a strategic decision that requires careful consideration. If your current brand fails to differentiate you from competitors or clearly communicate your value proposition and target audience, it could be time to rebrand. Success lies in approaching it as a strategic initiative, involving key stakeholders, and maintaining focus on innovation and market relevance.
Ultimately, a well-executed rebrand not only revitalizes an agency's image but also reinforces its commitment to delivering exceptional value to clients in an ever-changing environment.
If we look around, we're surrounded by big brands with names that didn't necessarily mean much before their success gave it meaning. For examlpe, did "google" even mean anything before 1998? It's natural to ask ourselves then if a name is really that important.
For small businesses, yes, a name is very important because it's your opportunity to put something compelling out there, capture the audience's attention, and differentiate your business. Nowadays it's getting harder to name a corporation, as it seems the good names are all taken. This has led to a trend of using unconventional names, which, while potentially memorable, risk confusing potential clients. The balance between distinctiveness and clarity has become a critical consideration in the naming process.
Jim's approach to rebranding starts with a name that is packed with meaning, is exciting to the client, and inspires them to put together a cohesive elevator pitch. A well-chosen name should serve as a foundation for effective storytelling, enabling businesses to communicate their value proposition clearly and memorably.
A name serves as the first point of contact between a brand and its audience and should encapsulate the essence of the agency's mission, values, and unique offerings. There's a lot of work to be done before landing on the perfect name, like understanding your differentiators, your promise to customers, and the legacy you want to leave. Understanding these elements correctly will help you come up with a clear brand promise and a word that represents that promise and brings it to light.
Additionally, think about the type of word you want. Do you want a descriptive word? Do you want to coin a term? Or maybe borrow meanings from existing words that can be contextualized within the industry? Naming, therefore, becomes a strategic endeavor that requires a deep understanding of the agency's strengths and the value it offers to clients.
Just remember the approval timeline associated with trademarking a name can take up to a year, which is why agencies should be confident in their chosen name and conduct a thorough review process, ensuring that it not only resonates with the brand's identity but is also legally viable.
Looking to dig deeper into your agency's potential? Check out our Agency Blueprint. Designed for agency owners like you, our Agency Blueprint helps you uncover growth opportunities, tackle obstacles, and craft a customized blueprint for your agency's success.
E2M Solutions: Today's episode of the Smart Agency Masterclass is sponsored by E2M Solutions, a web design, and development agency that has provided white-label services for the past 10 years to agencies all over the world. Check out e2msolutions.com/smartagency and get 10% off for the first three months of service.
The decision to hire a Chief Operating Officer (COO) marks a critical turning point in an agency's growth journey. Brittany recalls transiting to a COO role once her agency was big enough to need department managers. Of course, this can vary from business to business but for her it comes down to whether the owner was ready to hand off the keys of the business' growth, and whether they needed a second hand to get the agency to the next level.
Unlike an Operations Manager, whose role is managing the team, the COO is often seen as the backbone of an organization, responsible for ensuring day-to-day operations align with broader strategic goals. According to Brittany, bringing in a COO could be the best or worst decision you make, depending on who you put in that seat.
It's certainly a tricky role to hire and Brittany urges agency owners to clearly define their needs. Are you seeking someone to manage personnel, or do you need a strategic thinker to drive business growth and operational excellence? These fundamental questions can mean the difference between a successful hire and a costly misstep.
For growing agencies not yet ready for a COO, an operations manager can provide crucial support by taking on team management responsibilities. Given the high-stress nature of operations and its potential for burnout, finding the right person requires careful consideration of both management skills and operational expertise.
Agencies usually pay a pretty penny for someone who comes in with that talent. However, for smaller agencies that don't have the budget for an Operations Manager just yet, Brittany recommends training the best account manager to start to fit into that role.
A great Ops Manager should be a great leader with attention to detail and the ability to see the big picture. This internal promotion strategy provides a cost-effective path to filling a critical role while also creating growth opportunities that can boost team morale and retention.
A COO serves as the backbone of an organization, balancing multiple critical responsibilities that directly impact both the company's success and its culture. Here are three key attributes that define an exceptional COO:
Comprehensive knowledge of the agency. A great COO must understand how each department functions independently and how they interconnect to support one another. This understanding extends beyond internal operations to encompass the client perspective, as every strategic decision must account for both team capabilities and customer experience.
Strong financial intelligence is crucial for effective operations management. COOs must constantly evaluate agency profitability, assess resource allocation, analyze client contribution margins, and monitor employee costs. For example, an experienced COO like Brittany learns to view every decision through both a financial and customer-centric lens. Whereas earlier in their careers, they might have focused primarily on client satisfaction without fully considering the financial impact on the agency.
Leadership excellence stands as a fundamental yet often overlooked requirement. Many mistakenly believe that a COO's role revolves solely around numbers and processes. However, the position demands someone who can effectively guide and inspire teams toward organizational goals. Strong communication skills and leadership abilities are not optional extras but prerequisites for success in this role.
The relationship between CEO and COO is more nuanced than many realize, according to Brittany. At its core, it's a partnership between a visionary and an integrator, where the greatest challenge lies in maintaining distinct roles despite overlapping talents. Rather than seeking a mirror image of themselves, CEOs should look for COOs who complement their strengths—even if that means partnering with someone who seems like their opposite.
With these inherent differences, CEOs and COOs must learn to manage conflict, which instead of being avoided, should be embraced as a necessary element of collaboration that can serve as a mechanism for clarity. In her case, Brittany and her COO find the most constructive way to navigate conflict is to stick to facts and remove emotion. You want a COO who will complement you while also challenging you to think differently about issues to obtain the best possible results.
In an effective CEO-COO relationship, the foundation is trust and communication, anchored by shared core values and commitment to the organization's mission.
Brittany's advice to CEOs is to let your COO fail. If you don't fully agree with how they're planning to execute something give them a shot to try it their way. If they fail, your job as CEO is to help pick them back up, not criticize them, because otherwise they won't feel confident bringing forward innovative ideas in the future.
As Brittany highlights, finding the right COO is just the beginning; ensuring their longevity within the organization is equally vital.
The COO often bears the brunt of operational stress, alleviating burdens from the CEO and other leadership roles. Therefore, it is crucial for agency owners to actively support their COOs by ensuring they have all the tools they need to execute efficiently and feel supported. Implementing structured platforms for dialogue, such as regular check-ins and performance reviews, can facilitate healthy discussions about workload, expectations, and career aspirations. This not only helps in managing stress levels but also reinforces a sense of partnership and collaboration between the COO and the rest of the leadership team.
COOs can get overwhelmed and stressed too. Finding one that matches your organization well is already hard enough so once you do, make sure you can find a way to retain them.
Looking to dig deeper into your agency's potential? Check out our Agency Blueprint. Designed for agency owners like you, our Agency Blueprint helps you uncover growth opportunities, tackle obstacles, and craft a customized blueprint for your agency's success.
Smart Pricing Table: Today's episode of the Smart Agency Masterclass is sponsored by Smart Pricing Table, an award-winning proposal software built just for marketing agencies and designed to handle your unique challenges and cut down the time you spend on proposal as much as 90%. Go to smartpricingtable.com/smartagency to see if this is the missing piece your agency needs. Schedule a demo and get 50% OFF for the first two months.
Over thirty years ago, Marc, then the owner of a cosmetic company, met a branding specialist who had carved out his niche in the luxury sector. Their initial collaboration proved so successful that when Christian Dior acquired Marc's cosmetic company, the two of them saw an opportunity to create something bigger together and joined forces as DMA United.
According to Marc, their agency's approach has never been about self-promotion or chasing after marquee clients for the sake of reputation. Instead, Marc and his partner built their reputation on letting the work speak for itself. By focusing on the work rather than the accolades, DMA United has built a reputation that attracts clients organically, including industry giants like Sony Music, Warner Brothers Entertainment, and Pepsi.
Starting with their first big clients, Kerastase (a L'Oreal subsidiary), Marc's agency was able to move to working with other big names thanks in part to the relationships they built with CMOs. As CMOs move from one company to another, they often bring their trusted agency partners, creating a network of opportunities based on proven performance. Some of these CMOs have worked with his agency for their entire careers from big brand to big brand.
This dynamic also presents challenges. When a CMO leaves, the new leadership may seek to reinvent their brand strategy, often leading to the loss of established partnerships. Marc acknowledges this double-edged sword but suggests agencies can mitigate this risk by diversifying their offerings. By expanding their skill set beyond traditional marketing and into emerging technologies like blockchain, Web3, and artificial intelligence, his agency has created a unique value proposition that makes it harder for people to let go of them.
As a proponent and an author on AI integration in agency operations, Marc has developed a nuanced approach to incorporating artificial intelligence into his agency's work, focusing primarily on two areas: data analysis and content creation.
In the fashion and lifestyle sectors where Marc's agency operates, traditional data analysis often poses significant challenges. Executive teams typically struggle with multiple data sets and time-consuming reporting processes, making swift market responses difficult. AI technology addresses this pain point by enabling real-time data analysis, allowing executives to make informed decisions instantly. CEOs and CMOs can now evaluate marketing campaign performance across platforms immediately and adjust budget allocations dynamically for optimal results.
However, Marc's enthusiasm for AI comes with careful consideration of its limitations, particularly in creative work. While AI excels at generating quick visual content and creating operational efficiencies, his agency maintains a balanced approach. The technology's current state, still in its infancy, serves best as a complementary tool rather than a replacement for human creativity. The core of effective storytelling and branding, Marc argues, remains rooted in human insight and emotional intelligence.
Overall, his vision isn't about surrendering creativity to algorithms but rather about leveraging AI's strengths while preserving the irreplaceable human element in creative work and that, rather than a threat, businesses should focus on harnessing its potential to enhance their operations and drive innovation. Therefore, the future of creativity lies not in the replacement of human input but in the collaboration between human ingenuity and AI capabilities.
While artificial intelligence excels at producing high-volume, short-form content for our attention-starved digital landscape, he questions whether this marks the end of meaningful storytelling or perhaps signals an impending shift in consumer preferences.
The current media environment, saturated with brief clips and advertisements, has created a paradox: content is more abundant than ever, yet authentic engagement seems increasingly rare. Although AI helps meet the demand for constant content production, its output often lacks the emotional resonance and nuanced understanding that human creators naturally bring to their work.
There are growing signs of content fatigue among audiences which suggests a potential revival of long-form storytelling that weaves narratives that consumers can relate to. Brands can certainly benefit from this return to long-form that allows them to become educators and storytellers, providing insights that empower consumers in their decision-making processes.
AI can still be a center component in the creation of this longer content, of course, Marc just emphasizes it'll always need human overseeing to give it the relatability that will really engage people and keep them coming back.
Looking to dig deeper into your agency's potential? Check out our Agency Blueprint. Designed for agency owners like you, our Agency Blueprint helps you uncover growth opportunities, tackle obstacles, and craft a customized blueprint for your agency's success.
E2M Solutions: Today's episode of the Smart Agency Masterclass is sponsored by E2M Solutions, a web design, and development agency that has provided white-label services for the past 10 years to agencies all over the world. Check out e2msolutions.com/smartagency and get 10% off for the first three months of service.
Frustrated with his previous career as a software developer, Dale sought to learn more about digital marketing. Already dabbling in website development and affiliate marketing in his spare time, Dale found the digital marketing field appealing enough to leave his coding career behind. This transition led him to consulting and eventually founding his own agency, which has grown into a seven-figure business.
Until 2023, most new business came through webinars and strategic partnerships. However, an unexpected shift occurred as speaking engagements began generating the majority of his leads. This transformation was particularly notable by 2024, when conference appearances became his primary source of new business.
Before the pandemic, Dale had only attended a few small events, enough to discover his passion for public speaking. Once restrictions lifted, came his big opportunity. Many conferences were now looking for speakers, as many dropped out due to the reduced audiences. Dale took the chance, said yes to everything, and started a new unexpected stage in his career where he now travels most weeks doing something he really enjoys.
Understandably, many people fear getting on stage as an expert, especially if they're not very familiar with the subject. When Dale first started making taking the stage at these events, he spoke about his own case studies. It was a subject he knew well and felt comfortable talking about. This helped when it came to gaining confidence as a speaker and was something audiences loved because it was like pulling back the curtain on his processes and what he does.
For Dale, this is the ideal place to start, because instead of a dry informational speech you're providing insights and tips based on something you actually worked on and are passionate about.
How to Prepare for a Speaking Event:
You should never just show up to an event without previously researching and preparing for the subject you'll be covering. Dale has a comprehensive "event playbook"—a detailed spreadsheet outlining thirty specific preparation tasks for each speaking engagement. This tool outlines key strategies and actions tailored to the specific conference, which includes researching other speakers, understanding the audience demographics, and identifying potential opportunities for networking.
Understanding his audience allows him to craft targeted content that resonates with attendees, while additional initiatives like hosting dinner events create valuable opportunities for deeper connections in a more relaxed setting.
While the process itself isn't complicated, Dale clarifies this is not a process he completes on his own. He has three people on his team who help him execute this playbook starting from the planning and execution to following up with attendees afterword.
In public speaking, you may encounter two types of speakers, the givers and the takers. The takers often approach speaking engagements with a transactional mindset, focusing on what they can extract from the audience—be it attention, leads, or sales—without offering substantial value in return. In contrast, givers prioritize the audience's needs and interests, sharing insights and methodologies generously.
Dale firmly believes it's better to be a giver and often ends up sharing more than he had intended to. As a representative for an SEO agency, he advocates for a strategy of sharing even the most intricate details of their methodology, dubbed "SEO for Revenue."
By openly discussing their framework and providing actionable insights, Dale empowers his audience to understand the complexities of SEO while simultaneously positioning himself as a credible expert. Some people may think he's sharing too much, but most of the time what happens is that half the people try execute his recommendations and the other half decide they don't have the time to do it themselves and contract his services.
This tactic not only builds confidence in the speaker's capabilities but also encourages potential clients to seek their assistance when they realize the challenges involved in executing such strategies independently.
Speaking at events can be an excellent way to grow your business by getting yourself in front of your audience and establish your expertise. However, it can also be quite expensive. In his case, Dale doesn't pay to get a spot in these events. Half of the time he gets paid to speak and the other half he pays for his airfare and hotel.
As long as it nets out to zero, he's willing to attend as many conferences as he gets invited to. Speaking engagements offer not only a platform to share knowledge but also a unique opportunity to build credibility and foster connections that can lead to significant business growth, in addition to the visibility it can offer, as one speaking engagement can serve as a stepping stone to further opportunities.
Pro Tip: Include a Call to Action
To ensure you'll get the most of your time on stage and go home with new leads, Dale recommends adding a call to action that can get some audience members to send you their contact information. He makes sure to include a slide in the middle of his presentation with a QR code for anyone who wants to download the slides. This way, they fill out a form offering him a way to follow up after a few days. This call to action can vary depending on the topic of discussion. For instance, it may be a piece of content pertaining to the topic discussed or slides with prompts he mentioned during the presentation.
In the case of smaller groups, like a webinar, he already has their contact information and focuses on getting people to sign up for a strategy session.
With a few years of public speaking under your belt, you may start to recognize the importance of being selective with the events you attend to throughout the year. You may not want to travel as much and consider not attending the smaller events. In these cases, Dale encourages a team member to participate in speaking engagements as a strategic way to amplify his agency's presence.
As he sees it, nowadays everyone can be an influencer in their own right and can contribute to the brand's visibility. This is something he'll consider for future hires with a view to cultivate a team of individuals willing to share their insights and expertise to attract clients and enhance credibility. By fostering a culture that encourages and supports public speaking, businesses can cultivate a diverse array of voices that contribute to their growth and visibility.
Looking to dig deeper into your agency's potential? Check out our Agency Blueprint. Designed for agency owners like you, our Agency Blueprint helps you uncover growth opportunities, tackle obstacles, and craft a customized blueprint for your agency's success.
Smart Pricing Table: Today's episode of the Smart Agency Masterclass is sponsored by Smart Pricing Table, an award-winning proposal software built just for marketing agencies and designed to handle your unique challenges and cut down the time you spend on proposal as much as 90%. Go to smartpricingtable.com/smartagency to see if this is the missing piece your agency needs. Schedule a demo and get 50% OFF for the first two months.
Reade's digital marketing journey began as a high school student, when he worked at a family business and was tasked with figuring out how to build a digital strategy to attract customers online. Looking back, he doesn't know how serious they were in trusting such a young person with an important component of their business. However, Reade took it very seriously since it seemed like a smart thing to learn.
The abilities he gained from that experience and then starting and crashing his own business in college helped him continue down the path of marketing and content, working at an agency right after college. According to Reade, going through college taught him nothing about digital marketing or the skills he would continue to develop to succeed in that industry. Instead, it was the Hubspot certifications he completed during his time at that agency what helped him learn the marketing terminology he needed. At that time, he also started to take side projects, which led to eventually starting his own agency.
Many businesses focus heavily on client acquisition while overlooking the valuable opportunity of growing their relationships with existing clients. These established relationships represent untapped potential for growth, as current clients already understand and trust your services, making them more likely to engage with additional offerings.
To remain relevant in these clients' minds, Reade emphasizes the importance of consolidating client contacts from various sources—CRMs, spreadsheets, and databases—into a comprehensive email list and establishing consistent, meaningful communication through targeted content creation.
What is stopping most people from grabbing this low-hanging fruit? Many fear that emailing clients too often leads to them unsubscribing from their list. However, the risk of being irrelevant to them is far worse and gets you nowhere. Remember, if you don't ask, the answer will always be no.
Regular engagement will ensure customers are aware of your continued growth and ability to address their evolving business challenges. Moreover, satisfied clients often become brand advocates, providing referrals and testimonials that can be invaluable for attracting new business.
When it comes to client communications, Reade believes there's no such thing as too long, just too boring. If the information you offer is useful to people, they won't mind skimming through it to get to the most important aspects. If it's useless, however, they'll ignore it even if it's just a paragraph.
Original section, where you're leading with value by offering an original piece of content.
Curated section with recommendations of social media posts, articles, or videos you recommend.
Highlight section, where you can highlight case studies or products or services you offer.
It's enough to keep people informed about your services and milestones while not being too overwhelming.
Reade also dives into the effectiveness of subject lines and why it lies not in its consistency but in its ability to pique curiosity and draw the reader in. While establishing a recognizable brand can be valuable, he believes in the need for experimentation to generate curiosity. So instead of leading with your company name (ie: The XYZ Newsletter #45) try to create curiosity by leading with a particular piece of information that may be very useful for your audience.
Furthermore, testing various subject lines—from intriguing questions to bold statements—can yield insights into what resonates most with the audience. The goal is to spark interest and drive opens, which ultimately leads to deeper engagement with the content itself.
For Reade, 40% is the new 20% in terms of the goal for open rates. Aiming for a 40% open rate might be more appropriate nowadays considering the changes in email platforms and clients that often auto-open emails for security purposes, which can artificially inflate open rates. This is why he recommends recalibrating expectations and focusing on achieving higher engagement metrics that reflect the true interest of your audience.
In addition to content quality, list management plays a crucial role in optimizing your email engagement. For Reade, it's worth it to prune your email list to remove subscribers who are no longer interested in your content and thus refine your audience. This improves engagement rates and ensures you communications are reaching individuals genuinely interested in you offerings. It's essential for maintaining a healthy email list that drives meaningful interactions.
Interestingly, Reade places less emphasis on clickthrough rates compared to open rates. He recommends embedding complete content within emails rather than relying on external links. While low clickthrough rates aren't necessarily concerning when paired with healthy open rates, they can signal an opportunity to optimize content strategy. This might involve refining newsletter language and call-to-action elements to better guide readers toward desired interactions, especially when specific clickthrough targets exist.
While email marketing might not be considered the most glamorous marketing channel—some even see it as outdated—the data tells a different story. People are forty times more likely to make a purchase after receiving an email from a company than after seeing a social media post.
This highlights the power of direct communication. Email marketing allows businesses to connect with their audience personally, fostering engagement and driving sales in a way that social media often can't. Unlike the ever-shifting algorithms of social media platforms, email provides a stable, owned channel for nurturing leads and ensuring consistent outreach to an audience that has already expressed interest in the brand.
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