October 2025

Friday’s Frights: The Top 10 Scariest Things in Merchant Services

Happy Halloween! On this day of ghosts, goblins, and ghouls, we’re swapping campfire stories for tales from the sales crypt. These are the things that truly haunt the nightmares of every merchant services professional. So, bolt your doors, check your residuals, and count down the top 10 scariest things in our industry.

From the Home office in the basement of Bates Motel in Fairvale, California

Here are this weeks Top 10 Friday Scariest Things in Merchant Services

10. The Fortress Gatekeeper More terrifying than any haunted house guardian, this gatekeeper protects the decision-maker with supernatural devotion. They rise from their desk like a spirit from a grave, whispering the soul-crushing incantation: “They’re in a meeting… indefinitely.”

9. The Phantom Statement A merchant hands you a processing statement shimmering with promise—a ghostly image of incredible volume and juicy rates. You spend hours brewing the perfect proposal potion, only to discover the statement was a phantom from a busier time, or worse, a cursed relic from a competitor’s grimoire.

8. The POS-session The deal is signed in blood (well, ink). You arrive with the shiny new terminal, but the moment you plug it in, it becomes possessed. The Wi-Fi password is a lost spell, the POS system hisses and rejects the integration, and your new client watches as your soul slowly leaves your body.

7. “I Need to Consult the Spirits…” …”…of my partner/spouse/accountant.” The deal was alive, and now it’s trapped in the spirit world, its fate dependent on a mysterious entity you’ll never see. This isn’t a “no”—it’s a haunting, leaving a ghostly apparition in your pipeline for months.

6. The Cancellation Hex You open your email, and a curse leaps from the screen. The subject line glows like a bad omen: “Cancellation of Services.” It’s from one of your top accounts, a chilling digital hex that drains the lifeblood from your residuals with no warning.

5. The Mark of the Beast (on the Door) You approach a prime prospecting location, your hopes high, only to see it—the fresh, gleaming mark of the beast. A Square, Clover, or Toast sticker plastered on the door like a freshly carved jack-o’-lantern, signaling that another soul has already been claimed.

4. The Underwriting Underworld: “DECLINED” You fought the beasts, navigated the labyrinth, and returned with the signed contract. You cast it into the underwriting underworld for approval, only for it to be spat back out with a single, blood-red word: DECLINED. The deal is banished to the shadow realm, its potential forever lost.

3. “Can you just send me a scroll?” This ancient curse, often translated as “email me something,” is a surefire way to banish a sales rep. You know your carefully crafted parchment will disappear into a haunted forest of unread emails, its magic wasted.

2. The Calendar Crypt You dare to gaze into the future (your calendar for next week) and find only a desolate, empty crypt. No appointments, no follow-ups, no signs of life. It’s a terrifying silence, forecasting a famine of commissions and a long, cold winter.

And the #1 Top 10 Scariest Thing in Merchant Services is …

1. The “We Found a Cheaper Alchemist” Call The most bloodcurdling horror of all. It’s the ghostly whisper on the phone from your largest, most loyal account—the one that pays for your castle and feeds your gargoyles. They’ve been lured away by a rival sorcerer who promised the same magic for a few fewer silver coins. Your financial foundation crumbles, and the horror is complete.

Stay safe out there, and don’t let the sales monsters get you.

Oh, one more thing, I want to wish a Happy Birthday to my brother Jack. I hope you have a Spooktacular day!

Happy Halloween!

David

Your Pipeline is a Construction Zone

It’s Thursday morning and it’s already been a rough week. Between a brutal gatekeeper, and “we’re happy with who we have,” and a perfect deal getting shot down in underwriting, you will face problems. The single most important thing to remember is this: Never allow those problems to control your pipeline, your mindset, or your day.

The key to winning in this industry is knowing what you can and cannot control. You can’t control a merchant who is in a non-cancellable lease with a competitor. You can’t control a business owner having a bad day. You can’t control underwriting’s final decision.

Stop wasting energy there. To build a solid book of business and find real success, you must pour every ounce of your focus into what you can control.

From Obstacle to Opportunity: The Salesperson’s Mindset

It starts with an unshakable belief in your ability to solve problems. See every obstacle not as a roadblock, but as a stepping stone.

The Gatekeeper shuts you down? That’s a free lesson on refining your opening line for next time.
A deal gets lost to a competitor’s confusing, low-ball quote? That’s your cue to master how you break down a statement and clearly demonstrate your value.
A merchant ghosts you after a great meeting? That’s an opportunity to perfect your follow-up cadence.

This is how you take control. You stop letting the market happen to you and you start making your success happen. The problems will always be there; what changes is your mindset. Challenge the limiting belief that says, “This merchant will never switch,” and replace it with, “What is one more question I can ask to find their pain point?”

Embrace every challenge as a gift in disguise.

Failure is Just Data

In sales, rejection is constant. You will hear “no” far more than “yes.” But discouragement and failure are not the end of the road; they are simply data points on your path to a closed deal.

A lost sale is a chance to review your pitch. What objection did you fail to overcome?
A rough cold call is a reminder to sharpen your script.
A month that falls short of quota builds the hunger and resilience you need for the next one.

Every struggle you face today builds the strength, skill, and reputation you need to land that huge account tomorrow. You are in control of your destiny. You have the power to take that data, learn from it, and MAKE your next conversation better.

Control Your “AEF”: Attitude, Effort, and Focus

When it comes down to it, success in this business isn’t about the things you can’t control. It’s about mastering the three things you always can:

Attitude: How do you walk into the next business after getting thrown out of the last one? That choice is 100% yours.
Effort: Are you making one more call? Are you walking into one more door? Are you sending that personalized follow-up email instead of a generic template?
Focus: Are you dwelling on the deal you lost this morning, or are you zeroed in on the next prospect in your CRM?

Going forward, when a problem hits—a chargeback dispute, a terminal malfunction, a tough negotiation—welcome it. Use it as an opportunity to prove your value, learn something new, and grow. It’s all part of the process of becoming a top producer.

Happy Selling,

David

Hump Day or Victory Day? Crushing Your Mid-Week Goals

It’s Wednesday. Has the initial adrenaline from Monday’s prospecting leveled out? does the Friday finish line still seems a ways off? Is the end of the month weighing on you? Maybe the coffee doesn’t seem to be hitting quite the same. You’ve heard “I’m happy with my current provider” a few more times than you’d like, and that promising restaurant owner you spoke to on Monday has suddenly gone silent.

Welcome to the Wednesday Wall. This mid-week moment can either define your week or derail it completely. It’s the point where momentum can fade and the pipeline can start to feel a little too quiet.

But let’s reframe that. Wednesday isn’t the wall; it’s the turning point. It’s the day the pros separate themselves from the amateurs. It’s not just “hump day”—it’s the engine room of your entire sales week.

The Grind is Real, But So is the Opportunity

Let’s be honest, this job is a grind. You’re not just selling a service; you’re selling trust. You’re tasked with deciphering cryptic competitor statements, explaining complex pricing structures like interchange-plus vs. tiered pricing (IC+0.25%+$0.10), and convincing a busy business owner that your solution will genuinely make their life easier and more profitable.

By Wednesday, the rejections can feel heavy. But this is precisely where the opportunity lies. The seeds you planted on Monday and Tuesday need watering today. The conversations that stalled need a fresh perspective. Your week isn’t over; it’s just getting strategic.

Ready to turn the tide? Here are three actionable strategies to make this Wednesday your most powerful day of the week.

1. Reconnect With Your Real “Why”

Yes, the commissions are a powerful motivator. But when the grind gets tough, money alone won’t get you through the next “no.” You need to connect with your deeper purpose.

You aren’t just selling payment processing.

You’re helping that family-owned pizza shop save enough money to finally upgrade their worn-out oven.
You’re giving a local boutique the modern POS technology to manage their inventory seamlessly and finally compete with online giants.
You’re providing a busy mechanic with a reliable, cash-discounting program that puts thousands of dollars back into their business each year.

When you face a tough gatekeeper or a difficult price objection, stop thinking about your quota for a second. Instead, picture the business owner you’re trying to help. Your persistence isn’t just about closing a deal; it’s about making a tangible difference for their livelihood. Your “why” is your fuel. It’s time to refill the tank.

2. Master the “Value-First” Follow-Up

Monday was for opening doors. Wednesday is for walking through them. Too many salespeople fall into the trap of the weak follow-up: “Hey, just wanted to check in…”

Don’t be that salesperson.

Your Wednesday follow-up is your chance to prove you were listening. It’s an opportunity to provide value before you ask for the sale. Try this instead:

“Hi Sarah, I was thinking about our conversation regarding your high e-commerce fees. I found this article on three ways online retailers are reducing cart abandonment and thought you’d find it useful. Do you have two minutes to discuss how it might apply to your site?”
“Hi Joe, you mentioned you were frustrated with your current terminal’s downtime. My company just released a case study on how a similar auto shop increased their uptime by 99% with our new wireless POS. I can send over the one-page summary if you’re interested.”

A value-first follow-up immediately repositions you from a salesperson to a trusted consultant. It shows you’re invested in their success, not just their signature.

3. Sharpen Your Edge (The 30-Minute Challenge)

The payments industry is always changing. New technology, new security protocols (hello, PCI 4.0), and new sales strategies emerge constantly. If you feel like you’re hitting a wall, it might be time to sharpen your saw.

Take just 30 minutes out of your day today.

Listen to one episode of a top sales podcast (like “Sell or Die” with Jeffrey Gitomer).
Watch a YouTube video on how to dissect a competitor’s merchant statement more effectively.
Role-play your pitch or a common objection with a colleague and ask for blunt feedback.
Read up on a niche industry you’re targeting. Learn their specific payment pain points—what does a dentist’s office need that a coffee shop doesn’t?

A small investment in your skills today will give you the confidence and the fresh angle you need to break through a tough account tomorrow.

Finish the Week Stronger Than You Started

Wednesday is your launchpad for a winning Friday. It’s the day for strategic moves, renewed purpose, and relentless focus.

The deals you celebrate at the end of the week are almost always the result of the grit and intelligence you applied in the middle of it.

So, grab that coffee, pull up your CRM, and look at your pipeline with fresh eyes. Who needs that value-first follow-up? Which proposal needs one more push? The week is far from over. Go make it happen.

What’s your number one strategy for beating the mid-week sales slump? Share it in the comments below!

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

Friday’s Top 10 Prospecting Hacks to End 2025 Strong…

With Halloween and November just a week away, and taking away Thanksgiving, Christmas eve, Christmas day we only have 44 days left to sell. There’s a thought that creeps into every sales rep’s mind: “Everything is about to slow down. Businesses are too busy for the holidays. I should just build my list and hit it hard in January.”

6 Myths of Handling Sales NO’s

You’ve analyzed the statement, built the proposal, and you know you can save them money and upgrade their tech. You’ve got the deal locked down. Then you hear it: the dreaded “NO.”

Suddenly, your perfect proposal is dead in the water, and you start questioning your pitch. What do you do? Chalk it up as a loss and walk away, or do you dig in? Here are six common myths about hearing “NO” in merchant services—and how to bust them to close more accounts.

Myth #1: Every “No” is a Hard “No.”

Too many reps treat every “NO” the same. They aren’t. A “NO” from a small coffee shop that does $10,000 a month in volume is different from a “NO” from a multi-location restaurant group. Know which deals are worth fighting for.

More importantly, a “NO” often isn’t about you or your competitor. It’s the merchant choosing to do nothing. Inertia is your biggest competitor. They’re busy, their current system kind of works, and switching sounds like a hassle. Understanding whether you lost to a competitor or lost to inaction is the first step to crafting your next move.

Myth #2: NO Means “Next Opportunity.”

While you can’t waste time on lost causes, moving on too quickly is costing you deals. When a merchant tells you NO, you owe it to yourself—and your pipeline—to ask clarifying questions.

A “NO” is often just a “not right now.” Maybe their current processing contract isn’t up for six months, or they just bought a new POS system. By asking, “Could you tell me a bit more about what led to that decision?” you can uncover the real timeline. Stay engaged, set a follow-up, and turn a delayed decision into a future signed agreement.

Myth #3: You Know Why They Said No.

The biggest trap in this business is assuming you lost on price. Reps default to, “My rate must have been too high,” and move on. Stop assuming.

Did you ever consider:

They’re locked into a lease on their terminal/POS?
They have a business loan with the bank that provides their processing?
The person you spoke to isn’t the real decision-maker?
They’re worried the transition will disrupt business?

Always verify the “WHY” behind the “NO.” Multiple contacts within the business can give you the real story. Uncovering the true objection is the only way to overcome it.

Myth #4: A “No” Doesn’t Affect Your Mindset.

It absolutely does. Merchant services is a game of numbers and rejection. A string of “NO’s” can crush your confidence, and that energy carries into your next walk-in or call.

When you get a tough rejection, don’t just stew on it. Take immediate action. Call a happy client you recently set up and ask for a referral. Review a signed agreement from a big win. Remind yourself that you provide real value. Reset your mindset before you pitch the next merchant.

Myth #5: Your Pitch Was Perfect.

If you have an ideal merchant profile and they still say NO, don’t blame the merchant. Blame the process. Often, a “NO” comes from a mismatch between your sales cycle and their readiness to buy.

Did you rush to the rate comparison before understanding their operational challenges? Did you talk about saving them $50 a month when their real pain is inventory management or server performance on their outdated POS? Just because they’re a perfect fit doesn’t mean they’re ready for a signature. Create value and solve a business problem first; the rate becomes the easy part.

Myth #6: It Always Comes Down to Price.

This is the biggest myth in payment processing. If a merchant says “NO” because of price, it’s almost never about the rate itself. It’s because you failed to establish value that outweighs the cost.

Shift the conversation from price to cost. What is the cost of their current system’s downtime during a dinner rush? What is the cost of the hours they waste manually entering sales into QuickBooks? What is the cost of a single chargeback they could have won with better tools? When you connect your solution to solving expensive problems, the price becomes an investment, not an expense.

Hearing “NO” is part of the job, but it doesn’t have to be the end of the conversation. Every “no” is an opportunity to learn, adapt, and refine your approach.