Category: Motivational

Let’s be honest: some mornings are harder than others. After all these years in this game has taught me that talent is great, but grit is what pays the residuals. This is my personal collection of the thoughts, quotes, and mindsets that keep me moving when the coffee isn’t enough. It’s about finding the “Why” that’s bigger than the “No.”

Hide & Seek & Tag: How Kids’ Games Taught Me a Merchant Services Lesson

It’s December 30th, and after a glorious, much-needed week off, I’m back in the saddle! My brain is officially cleared of email backlog and deadlines, and instead, it’s filled with the delightful, chaotic memories of Christmas break.

For the last seven days, my home has been the unofficial headquarters for holiday fun. My own grandchildren, along with half the neighborhood kids, were constantly tearing through the yard, fueled by cookies and holiday excitement. The primary activities? Hide-and-Seek and Tag.

And, surprisingly, watching all that running, giggling, and strategy got me thinking about us—the business of selling merchant services.

The Game of Tag: Speed and Focus

When a child is “It” in the game of Tag, what’s their goal? To make contact with the next person as quickly as possible. Every moment counts.

The Merchant Services Parallel:

In our industry, the “It” is the new technology. The goal is to get that solution in front of the right business owner before a competitor does, or before the business owner resigns themselves to the status quo.

  • Speed: If a business has a pain point (high fees, outdated terminals), the first provider to clearly articulate a solution is usually the one who wins. We must be fast in our follow-up and faster in our proposal delivery.
  • Focus: You don’t just run blindly. You zero in on the one target who is closest or most vulnerable. In sales, this means identifying the business that is truly ready for a change, has the highest need, and represents the best long-term fit. Don’t chase everyone; focus on the ones you can truly help now.

Hide-and-Seek: Discovery and Trust

In Hide-and-Seek, the players go silent and disappear, hoping to go undetected. The “Seeker” must methodically check every location, be patient, and ultimately, discover the hidden player.

The Merchant Services Parallel:

The “hidden player” is the true objection or underlying concern of a prospect. They might say, “I’m not interested,” or “My current provider is fine,” but the real reason for their hesitation is often hidden.

  • The Seek: Our job isn’t to blast features; it’s to ask the right, quiet questions to discover the real reason they are resistant to change. Is it fear of downtime? Uncertainty about a new agreement? A bad experience with a previous provider?
  • The “Ally” Seeker: Unlike the playground, our goal is not to “catch” the prospect. It’s to be a trusted advisor who helps them discover the value. When we find their hidden need (e.g., they didn’t know they could integrate their POS with their loyalty program), we’ve “discovered” the sale.

The Power of “Safe on Base”

In both games, there’s usually a designated “Base” or “Safe Zone.” It’s the place where, for a moment, the running stops, the fear of being tagged disappears, and you can catch your breath.

The Merchant Services Parallel:

This is what we must become for our merchants: Their Safe Zone.

In a world of confusing fees, non-stop sales calls, and confusing PCI compliance standards, businesses crave a single point of contact they can implicitly trust.

  • Offer Stability: When a merchant knows they can call you directly with a terminal issue, a chargeback question, or a statement inquiry, they feel safe. This comfort stops them from feeling the need to run to the next ‘cheaper’ offer.
  • The Ultimate Retention Strategy: Providing outstanding support—being their “Base”—is the single greatest long-term retention strategy we have. It turns a client into a partner.

What Will You Chase in the New Year?

Watching those kids run around, completely absorbed in their simple games, reminded me that success is often about sticking to the fundamentals: Speed, Focus, Discovery, and Trust.

My Christmas break gave me a refreshed perspective, and I’m ready to apply these playground lessons to the business of growing sales in the new year.

Here’s to a fast, focused, and prosperous final push to the end of the year!

Happy Selling,

David

Enduring Gift of Kindness

We’ve all seen it – those heartwarming messages that pop up when we least expect them, reminding us of the simple power of human connection. The image of a chalkboard sign, boldly declaring,

“SOME STRANGER SOMEWHERE REMEMBERS YOU BECAUSE YOU WERE KIND TO THEM”

really hits home, doesn’t it? especially this time of year.

As merchant services sales professionals, we’re constantly striving to meet targets, close deals, and expand our portfolios. But especially now, as Christmas lights begin to twinkle and the spirit of goodwill fills the air, it’s a powerful reminder that our interactions go far beyond just processing payments.

The “Kindness ROI” in Merchant Services

Think about it: in a competitive landscape, what truly sets you apart? While product features and pricing are important, the experience you provide can be the most memorable and impactful differentiator.

  1. First Impressions Last: Just like that stranger remembering your kindness, merchants remember how you made them feel during your initial approach. Was it rushed and transactional, or empathetic and genuinely helpful?
  2. Listening with Empathy: During your pitch, are you truly listening to their pain points, their hopes for growth, and their concerns? Taking the time to understand their unique business needs, rather than pushing a generic solution, is an act of kindness.
  3. Patience and Persistence (with a Smile): The sales cycle isn’t always quick. There will be follow-ups, objections, and moments where you need to reiterate value. Maintaining a positive, patient, and kind demeanor throughout this process builds trust and goodwill.
  4. Exceptional Follow-Up and Support: The sale isn’t the end; it’s the beginning. Being responsive, proactive, and genuinely helpful after a merchant signs on is perhaps the greatest act of kindness. It shows you care about their long-term success, not just your commission. This kind of post-sale support can turn a client into a raving fan – someone who remembers you and is eager to refer others.

Christmas: A Season for Connection and Compassion

This time of year amplifies the importance of these connections. Small businesses are often bustling, sometimes stressed, and deeply invested in making the holiday season successful for their customers. As a merchant services professional, you have the opportunity to be a source of calm, clarity, and genuine assistance.

  • Are you checking in to see if their holiday processing is smooth?
  • Are you offering solutions for increased seasonal traffic or online sales?
  • Are you simply wishing them a merry Christmas and thanking them for their business?

These seemingly small gestures of kindness can leave a lasting impression, creating loyalty that no competitor can easily break. They remember the sales rep who was more than just a salesperson; they remember the person who cared.

So, as you go about your calls, meetings, and follow-ups this Christmas season, remember the message on that sign. Every interaction is an opportunity to leave a positive mark. Be the reason “some stranger somewhere remembers you because you were kind to them.” Not only is it the right thing to do, but it’s also incredibly good for business.

Happy Selling,

David

It’s December 1st. The 2026 Countdown Starts NOW.

Happy Monday, and Happy December!

Go ahead and look at the calendar. That’s right—it’s December 1st. The final chapter of the year is officially open, and the countdown has begun.

For many in sales, this day marks the beginning of the “holiday slowdown.” They see a month of distractions, out-of-office replies, and “call me next year” excuses. They ease off the throttle, start thinking about holiday parties, and mentally check out, ready to “hit it hard” on January 2nd.

But for us? This is where we separate ourselves.

This isn’t a slowdown. This is a launchpad.

What you do in the next 31 days doesn’t just determine how you finish 2025—it determines how you start 2026. And the best part? The phone lines are wide open for the most positive conversation you can have all year.

The Power of the “2026 Plan”

This month, we aren’t just selling merchant services. We are selling a stronger 2026 for our merchants.

Think about every single business owner on your prospect list. What are they doing right now, today, on December 1st?

They aren’t just managing holiday inventory. They are sitting at their desks, looking at their 2025 Profit & Loss statements, and asking one critical question: “How do we make more money in 2026?”

They are actively planning. They are setting budgets. They are looking for any and every competitive advantage they can find to make next year better than this one.

And that is precisely why your call isn’t an interruption—it’s an answer.

Make the Calls: You’re Not Selling, You’re Aligning

The “they’re too busy” mindset is a trap. Let’s flip the script.

  • Weak Pitch: “Hi, I know you’re busy, but do you have 15 minutes to review your processing statement?” (Translation: “Please let me interrupt you.”)
  • Strong Pitch: “Hi [Prospect’s Name], it’s [Your Name]. As you’re heads-down building your budgets for 2026, I’m calling to schedule a 15-minute ‘2026 Kick-off’ call. My goal is to show you a plan to add $X,XXX back to your bottom line before Q1 even starts. When do you have time next week or the first week of January?”

See the difference? You’re not asking for their time now. You’re aligning with their number one priority: planning for a profitable new year.

You are the first, most positive step in their 2026 strategy.

Your December Mission: Build the “January Jumpstart”

This month is about a powerful, positive, two-track mission:

  1. Finish 2025 Strong: Re-engage every proposal still on the table. Create urgency by positioning it as a year-end win. “Let’s get this approved before the 31st so you can start 2026 with a fresh, clean P&L and new savings already locked in.”
  2. Build Your 2026 Pipeline: This is the real prize. Every call you make today is a seed planted for January. While your competition is slowly waking up from their holiday break on January 2nd, you’ll be walking into a calendar already full of qualified appointments. You won’t be starting your year; you’ll be launching it.

Your Monday Action Plan

The countdown is on, and the energy is high. Let’s make it happen.

  • Block Your “Power Hours.” The next 31 days are precious. Protect your call time. From 9:00 AM to 11:00 AM, your only goal is to connect with business owners about their 2026 plan.
  • Lead with Positivity. Every call is an opportunity. You have good news to share. You are here to help them start their new year better.
  • Call Your “Fans” First. Call your best existing clients. Thank them for their business in 2025. Ask them, “What is your biggest goal for 2026?” Listen. Then ask how you can help them get there (and who they know that you should be helping, too).

This is it. The final month. The final push. The grand finale.

Every call you make, every meeting you set, every connection you build this month is a deposit in your 2026 bank account.

Let’s get on the phones and build a fantastic new year, starting today.

Have a powerful December 1st.

David

Mondays Aren’t For Moaning. They’re For Making Money

The alarm goes off. It’s Monday. For most of the world, this is a signal to groan, roll over, and mourn the end of the weekend. But you’re not most people. You’re a sales professional. And in our world, Monday isn’t the end of something; it’s the beginning of everything.

Monday is the clean slate. It’s the fresh start. It’s the day you set the tone for the entire week and decide whether you’ll be chasing your tail or closing your next big deal.

The difference between a top performer and an average rep is how they treat the first 3 hours of their Monday. So, grab your coffee, and let’s talk about how we’re going to win this week. It comes down to three things: Goals, Action, and Money.

1. The Goal: Reset Your Scoreboard

Whatever happened last week—good or bad—is in the past. A monster week doesn’t guarantee future success, and a tough week doesn’t have to define this one. Today, your scoreboard is reset to zero. This is your chance to set clear, aggressive, and achievable goals for the next five days.

Don’t just think about your monthly quota. Break it down. What do you need to accomplish by Friday to be on track?

  • Be Specific: Instead of “I want to make more sales,” define it. “I will get 10 new qualified leads,” “I will run 5 POS demos,” or “I will get 3 signed applications in the pipeline by EOD Friday.”
  • Write It Down: Put your weekly goals on a sticky note and stick it to your monitor. Write it on a whiteboard. Put it somewhere you can’t ignore it. A goal that isn’t written down is just a wish.
  • Identify Your Key Target: What’s the one deal in your pipeline that, if you closed it this week, would be a game-changer? Make that your #1 priority.

Monday is for strategy. It’s the moment you look at the map before you start driving. A few minutes of planning now will save you hours of wasted effort later.

2. The First Step: Ignite Your Momentum

Goals are worthless without immediate action. The biggest mistake reps make on Monday is easing into the week. They spend an hour on internal emails, shuffle papers, and “get organized.” That’s a losing strategy.

Your first 90 minutes on Monday morning are sacred. This is your “Power Hour.” It’s when your energy is highest and your focus should be sharpest. Use this time exclusively for revenue-generating activities.

  • Pick Up the Phone: Don’t warm up with emails. Your first action of the week should be prospecting. Make 10 cold calls before you do anything else. Get a “NO” out of the way. Get a conversation started. The hardest call is always the first one.
  • Follow Up on Last Week’s Heat: Did a merchant say “Call me next week”? Guess what? It’s next week. Your first call should be to that warm lead you cultivated last Thursday. Show them you’re punctual, professional, and hungry.
  • Get Out the Door: Pull the door handle and get out in the field. Make your first stop of the week at that new business park you’ve been meaning to hit, or the restaurant that just had its grand opening. Be the first face they see this week.

Momentum is everything in sales. A small win on Monday morning—a scheduled appointment, a great conversation, a request for a statement analysis—creates a ripple effect that will carry you through the entire week.

3. The Money: Connect Every Action to Your Commission

Let’s be honest. We’re in this business to help merchants, but we’re also here to build a great life for ourselves. Every dial, every door we open, and every meeting is a step towards your next commission check.

Your Monday mindset should be wired directly to your wallet.

Think about it:

  • That extra hour of prospecting you do today could uncover the deal that pays for your next vacation.
  • The disciplined follow-up you execute on a lukewarm lead could turn into the sale that hits your goal you’ve been shooting for.
  • The positive attitude you bring into the office sets a standard and creates an environment where success is inevitable.

Every Monday, you have a choice. You can let the week happen to you, or you can happen to the week. You can be reactive, or you can be proactive.

So, the choice is yours. Are you going to treat today like just another Monday? Or are you going to treat it like the first step toward your most profitable week of the year?

The scoreboard is clean. Your pipeline is waiting.

Now, go make it happen.

Happy selling,

David

Stop Working IN Your Business and Start Working ON It.

We’ve all been there. You’re in a rhythm. You’re prospecting, running appointments, closing deals, and putting out fires. You’re consistently hitting a number—maybe it’s 10, 16, or 20 deals a month. You’re making good money, but you’ve hit a ceiling. No matter how hard you grind, you can’t seem to break through that plateau.

The problem isn’t your work ethic. The problem is that you’re the most valuable employee in your own business. To scale, you have to start thinking like the CEO.

This requires understanding one crucial concept: the difference between working IN your business and working ON your business.

Working IN Your Business: The Daily Grind

Working IN your business is the core of what you do every day. It’s the “job” part of being an independent sales professional.

  • Prospecting and cold calling
  • Running discovery meetings
  • Analyzing merchant statements
  • Closing deals and getting signatures
  • Submitting paperwork
  • Handling terminal installations and customer service calls

These tasks pay the bills. They are essential. But by themselves, they will only take you so far. There are only so many hours in a day, and you can’t clone yourself… or can you?

Working ON Your Business: The CEO Mindset

Working ON your business is stepping back from the day-to-day grind to build a system—a machine that can operate even when you’re not personally turning every gear. This is where you put on your manager hat and architect your growth. It involves asking strategic questions:

  • How can I streamline my process?
  • What tasks can I delegate?
  • How can I create repeatable procedures for success?
  • What is the long-term structure of my business?

If you’re stuck at that 5-6 deal ceiling, it’s because you’re spending 100% of your time working IN the business. The path to 10, 15, or more deals a month isn’t working harder; it’s working smarter.

Your 30-Minute Growth Strategy

You don’t need to stop selling. Keep closing those those 5-6 deals. But it’s time to reclaim a small piece of your day for CEO-level thinking.

The Challenge: For the next month, block off the first 30-60 minutes of your workday to work ON your business. Do it when your mind is fresh, before the daily chaos begins. The mundane tasks of prospecting and paperwork can be done on autopilot later. Use this golden hour to think.

Ask yourself:

  • What tasks could I pay someone $15/hour to do? (Think list building, data entry, scheduling installations, follow-up “thank you” calls).
  • Can I create a procedure for this? What are the exact steps for onboarding a new client, from signed app to a happy, processing merchant? Write them down.
  • What could I delegate to free up my selling time? Imagine offloading the 5-10 hours a week you spend on paperwork and administrative tasks. What could you do with that extra time?

This is what working ON your business looks like. It’s the foundation for your first hire.

Navigating the Pitfalls of Your First Hire

Hiring your first assistant (virtual or in-person, using services like Upwork or Fiverr) is terrifying and exhilarating. Here’s what to expect and how to handle it.

1. They WILL Make Mistakes. Let’s get this out of the way: your first hire will make every mistake you can imagine, and some you can’t. They will mess up paperwork. They will call the wrong person. It’s going to happen. Embrace it. Mistakes are the price of growth and learning. Don’t let the fear of imperfection keep you trapped doing everything yourself.

2. Delegate Wisely. Your core skill is closing deals. DO NOT delegate closing to a new, inexperienced hire. That’s like a surgeon asking a rookie to perform the main operation. Instead, have them handle the tasks around the sale:

  • Pre-Sale: Building lead lists, scrubbing data, some initial appointment setting (with a script).
  • Post-Sale: Completing application paperwork after you get the signature, scheduling the installation, making the first follow-up call to ensure the merchant is happy.

You want to hire someone you can train and mold. Pay a fair wage ($25k-$35k to start) and increase their compensation as they become more valuable to your operation.

3. The Resentment Trap. You will inevitably feel a flash of resentment. You’ll think, “Why am I spending two hours teaching them how to do something I could do in 15 minutes?” This is a lie your brain tells you to keep you “safe” in your comfort zone.

Reframe your thinking: You are not losing two hours; you are investing two hours to buy back hundreds of hours in the future. Once you train someone to handle that task, you never have to do it again. Create a procedure (a simple document or a quick screen-recording video) during the training, and delegating to the next person becomes even easier.

4. Communication is Oxygen. Lack of communication will kill your growth faster than anything else. Your business cannot rise above your leadership. Without clear, consistent communication, you haven’t hired a team member; you’ve created a new, expensive problem. Set up regular check-ins, provide clear instructions, and create a culture where they feel comfortable asking questions.

Your Path Forward

Leverage your “laziness”—that desire to not do the repetitive, boring tasks anymore. Convert that feeling into fuel. Use 30 minutes each day to build the systems that will free you.

Continue to wear your employee hat and be the best salesperson in your company. But also put on your manager hat and become its best leader. That is how you break the plateau and build a true merchant services business, not just a job.

Happy Selling,

David

Birthdays, Mondays, and Sales

Today, October 27th, has always been a special day for me. It’s my birthday—a personal New Year’s Day. It’s a time to reflect on another year around the sun, a time to take stock of the wins and losses, and a time to reflect on another year of growth. As I was thinking about this annual ritual, I realized how similar it is to the mindset we need not just once a year, but every single week, and even every single day in our profession.

It all comes down to the power of a fresh start.

The Birthday Mindset: Our Annual Review

A birthday is the ultimate reset. You look back at the person you were 365 days ago and measure the distance you’ve traveled. You celebrate the milestones, learn from the missteps, and set intentions for the year ahead. It’s a day of perspective, gratitude, and forward-looking energy. You get to decide what you’re leaving behind and what you’re carrying into your next chapter. This is your personal annual review, and you are the CEO of your life.

The Monday Mentality: Your Weekly Reset

Now, think about Mondays. For many, Monday has a bad reputation. It’s the end of the weekend and the start of the grind. But for a sales professional, that perspective is a recipe for failure. We have to see Monday for what it truly is: a fresh start.

A Monday is a micro-birthday for your career goals. It’s the starting line for the week. It’s your chance to look at last week’s pipeline, analyze what worked and what didn’t, and map out your plan of attack.

Did you hit your call numbers?

Did you close the deals you expected?

Monday is the time to learn from last week’s performance and hit the reset button with renewed focus and energy. A great week doesn’t just happen; it’s launched with intention on a Monday morning.

Selling Merchant Services: The Daily Fresh Start

This brings me to our world: selling merchant services. If there is any profession that requires an endless supply of fresh starts, it’s this one. Our days are filled with rejection. We hear “NO,” “not interested,” and “we’re already happy” more times than we can count. It can be easy to let the weight of one bad call crush the next one.

But this is where the birthday and Monday mindset becomes a superpower.

Every single call we make is a fresh start. Every new business door you open is a fresh start. The last “NO” has absolutely no bearing on the next “YES,” unless you allow it to. Your success in this industry is directly tied to your ability to reset, instantly, and treat every new interaction as the most important one of the day. You have to be able to celebrate the small win of a good conversation and immediately move on to create the next one, without dwelling on the rejection that came before it.

So whether it’s your birthday, a Monday morning, or just the next call on your list, embrace the opportunity to begin again. Reflect on what you’ve learned, set your intention, and execute with passion.

Our success is not defined by singular moments, but by our relentless commitment to starting fresh.

Happy Selling,

David