A Tale of Two Sales People: My Recent Purchase Experience

For the past five years I’ve been pulling my kids in a trailer and occasionally riding for myself on a bike I bought over twenty years ago.

My sons are growing up, learning to ride their own bikes, and finding their own fun on two wheels, so I decided it was time for me to rediscover the long-distance riding I enjoyed.

I wanted to buy a new bike, but I wasn’t ready to walk into a store and speak with a salesperson. Bikes had become so much more technologically advanced and expensive since I last purchased one.

As I started to research all of the new advancements and possibilities, I was reminded of the steps my customers take when they’re looking to purchase new equipment or technology. They do a ton of research, speak with friends and colleagues, and are about 80% ready to buy when I’m brought in as one of the salespeople to compete for the deal.

My online research and readings had me about 60% ready to buy, but I needed to speak with someone who was knowledgeable about bikes and had made a similar and more recent purchase, so I immediately called my friend Dominic.

For years Dominic has been riding competitively, leading tour groups and gravel rides, and even organizes a one-day ride across Illinois from the Mississippi River to Lake Michigan, which I will be doing in 2023.

Dominic asked me about the riding I like to do, my research, and what was important to me. Our conversation led me to start looking for an aluminum bike that sat up higher in front with higher-end components to help with my long-distance rides.

Now I was ready to walk into a bike store and start my buying process.

I told the first salesperson about the two different bikes I was interested in, the level of components, and that I wanted it in aluminum. He immediately took me to the more expensive carbon fiber bikes and explained why I should consider these instead. They did have some cool features that the aluminum bikes didn’t, but it would cost me more than I budgeted for or really needed. I reminded him that I didn’t want carbon fiber, but he immediately doubled down on why it was so important and shouldn’t consider anything else. I thanked him for his time and walked out of the store.

The salesperson at the second store had a completely different approach. I mentioned the bikes I was interested in and wasn’t shown any bikes at all. Instead, like my friend Dominic, he started asking questions about my current bike, the riding I like to do, how often I ride, and where I like to ride.

He agreed the bikes I wanted to see would work well and then pointed out that there were some awesome gravel trails where I liked to ride and asked if I did any gravel riding.

I told him that I’d always wanted to but thought I needed a different type of bike for gravel. He brought me over to one of the bikes and explained how this one had everything I was looking for in a road bike, but also had the capability to ride on gravel because of the carbon fork and wider wheelbase that allowed for gravel tires.

My world just doubled in size. I could do all of the long-distance road rides, and then switch out the tires to explore all the gravel and dirt trails I used to just pass by.

Then to top it all off, he explained how to get used to the new disc brakes, their generous return policy, and how I’d receive two complimentary tune-ups. This reminded me of the level of service that Benco Dental and our manufacturing partners work to offer our customers so they’re happy and comfortable with their big purchases for years to come.

The exact bike I purchased was available for the same price at both stores I visited. Which store do you think I bought it from?

Buying my new bike turned out to be such an awesome experience. I was provided with incredible service, an amazing product that exceeded my expectations, an opportunity to reflect on my customer’s purchasing process, and a spark to want to write more stories like this.

I strive to run my customer meetings by focusing on the customer’s point of view, asking the best questions, truly listening to their needs, and always working to show them their gravel roads.

If you’re looking for a dental sales representative and full-service distributor who puts the customer first and will work to get you what you want, please reach out to me or your local Benco Dental representative.

Beware of Your Personal Brand

I had enough content to start my website, but I needed a personal brand. My friend Ryan, who was helping me with the graphics, told me that my signature was unique and maybe he could create a logo based on it.

I always thought I had poor penmanship but you know what—he was right—my signature was unique. I was unique. My site was going to be unique. So I started writing my name over and over again like a sixth grader with a crush and a new pen.

Jason D Dempsey

Jason D. Dempsey


In the end I just sent him my regular signature, the exact same one that many bank tellers and waitresses have received throughout the years. 

We discussed the idea of creating the logo around my initials (JDD) because I wanted people to see there were two Ds in the website name. I took jasonddempsey.com because it was available and my business cards always seemed to say Jason D. Dempsey—so why not?

Not only is Ryan a talented designer, he’s also a published writer. He started asking me about my vision for the site, what I wanted to convey to the readers and what three adjectives would best describe my logo and website?

I couldn’t come up with anything so I just started babbling about the phases I saw the website going through. 

  1. The first being a way for me to improve my writing, learn more about online marketing, SEO and showcase my skills as a sales and marketing person.
  2. Give me another way to connect with customers and share other people’s stories to gain meetings and sales.
  3. Showcase my new experiences and allow me to have other new opportunities I hadn’t even dreamed of.

After my ten-minute stream of consciousness he just looked at me and said, “I’m hearing the words authenticity, voice and authority.”

I said, “Exactly.”

I then got really excited about what this could mean and with a new rush of creativity and I quickly drew a crude logo that I thought would definitely be the one.

My wife overheard me, saw my crude drawing and said, “Don’t be that client.”

I lowered my head because I immediately knew what she meant. When I was in marketing and we were working on the creative components of a campaign or product launch, the product and business managers would always have a ton of ideas for the tag lines, ads or other fun parts. 

I can’t really blame them—they were the fun parts and some of their ideas were very insightful—but it always came across as, “Anyone can do marketing.”

Later the following week Ryan sent me back a bunch of awesome logos in different color schemes and ways they could work on the website. One of the best parts of working with an artist is how they can take your simple idea and create something that totally surpasses your expectations. He definitely did that and my site would not be where it is today without his creativity and hard work.

Ryan did humor me and created a logo that looked a little like my drawing. I never saw the similarities when I drew it but here it was as clear as day. My initials, name and reputation were just one strategically placed dot away from becoming a penis. 

Here it is in all its glory. 

I like to think he did it to teach me a lesson—maybe he didn’t—but it did allow me to see myself for how I was behaving.

If we went with my idea then the real question would have been who’d be the first person to place that strategic dot on my new logo? One of my brothers or friends?

Lesson learned. 

I focused on a couple of the logos that worked better for my messaging and in the end we went with the logo you see on the site today.

The logo is simple, emphasizes my middle initial and also is the perfect size to use for thumbnail images. I also wanted to incorporate some other parts of my life in the site. 

You’ll notice the other icons on the site are a record player and bicycle paired with my logo and the words Listen. Apply. Process. The three icons and words represent how I approach every sales meeting, my writing, and the development of this website. I’m also an avid biker and love listening to music, going to concerts and I’m a volunteer for CHIRP Radio in Chicago. 

My intention for the site was to share success stories from my job, talk about biking in Chicago, and incorporate my love for music and happenings at CHIRP.  Even though some things have changed in regard to my employment, this whole experience has become so much more. 

It has been an incredible exercise in listening to myself and others, discovering what I want out of my life and career, examining how I present myself to the world, processing that information and applying my knowledge and skills to the best of my ability. 

I hope I just don’t come across as a you-know-what.

Why You Need a System to be Successful in Sales

The most successful customers and businesses I’ve worked with always had a system. That’s why I’m on a mission to create my own system that will allow me to work on the extra things in my career and life that I know will help me achieve my vision for success. 

I’ve been able to identify some new methods that are helping me accomplish more of these extra tasks—but I’ve also come across some that I know won’t work for me, like habit stacking. If habit stacking would work for me, I’d floss more.

And even though habit stacking doesn’t work for me—habit tracking does.

One morning I was scrolling through my podcasts for a sales topic that spoke to me. I have a few staple sales podcasts where I like the host and their interview style, so I usually skim their topics until something jumps out at me. The air dates don’t really matter because the great sales tactics and sales people are always timeless. If the podcast really resonates with me then I will check out the guest’s website or podcast—they all have them.

While scrolling through the Salesman Podcast with Will Barron, a certain title caught my eye: Why Strategy, Not Working More Makes Millionaires with Brian Margolis (show #615 April 12, 2019).

In the podcast Margolis explains how his Pillars System helps you create a simple weekly strategy that allows sales professionals and entrepreneurs to earn more by focusing on less. 

Your tasks in The Pillars System are meant to be kept simple and small enough to fit on an index card. I immediately took interest in Brian’s system because it highlights how improving on a certain skill or executing some tasks more regularly will help your business and career take major leaps over time. 

I reached out to Brian via LinkedIn and asked him why people need systems and why the Pillars System works he said, 

“You can grind your way to a certain level of success with just your talents/skills alone, but if you want to go to the next level, you need to have an actual strategy. A strategy that tells you ahead of time where to intentionally spend your limited mental energy.  If you count on making the right decisions about where to spend your time and energy in the heat of the moment, you will usually do the urgent, not the significant.”

The Pillar System is a proven way to create that strategy.

Here is how The Pillars System is supposed to look on an index card. 

PillarsIdeasTo Do 
One BlogFuture Blog IdeaMeeting
3 WorkoutsNetworking GroupWeekly To Do List
4 Hours STA
1 Hour Website
Stain Deck

The first column is for your Pillars and other two columns on the index card are for your To-Do list and an Ideas section. 

The To-Do list has your main tasks for the day, these are the tasks that you already perform on a regular basis for your work or personal life. The ideas column is for the thoughts that pop in your head throughout the week that you may want to work on. You put these new ideas here so you can re-visit them later and so they won’t interfere with your daily routine

Here are some of my Pillars that I identified as things I wanted to work on and accomplish each week:

  • One blog 
  • 3 workouts (20 mins + stretch + 25 pu)
  • 4 hours STA
  • 1 hour on website

The list of four things you see above are the extra things I want to work on each week in addition to my regular job and family obligations. It contains both professional and personal goals. The tasks are written in shorthand to fit on the index card everyday.

Here’s what each Pillar actually means for me:

  1. One blog – My goal is to finish one blog draft each week. It doesn’t have to be ready to post but I should be able to send it to my editor for future posting. Now I added in the finalization of a draft I received back from my editor to post. This pillar actually started as just writing for two hours a week in order to make writing become a habit but it evolved over time.  
  1. 3 workouts (20 mins + stretch + 25 push ups) – This actually started off with more days and longer workouts but I soon realized that pillar that wasn’t being reached each week so I changed it to three days a week and only twenty minutes. This made the task more manageable and shortly after that I was checking it off each week. 
  1. 4 hours Sharpening the AX (STA) – This refers to doing outside learning about sales and other subjects that I believe will help my business. It can be reading a book, article or listening to podcasts. Podcasts allowed me to increase this from two hours to four. 
  1. 1 hour website – Everyone said to do a WordPress site and it just takes time to learn. I’m still learning.

The Pillars strategy allowed me to frame each week with my main tasks like meetings, sales calls, family duties and then add in my dream tasks (Pillars): writing, working out, reading/learning, etc. 

One of the other things that the Pillars System emphasized was having a Friday Night Feeling: something that left you feeling finished at the end of each week. I took that one step further to make sure each day I had a Five O’Clock Feeling. And before any of you super sales people or wannabe Gary Vees start messaging me on how, “There are no weekends!” “I never stop working!” Or “This is why you’ll never achieve your dreams!” Just Stop.

The Friday Night and Five O’Clock feeling allow me to look back at the end of each day and each week and have a sense of accomplishment knowing I did what I set out to do. This allowed me to then look forward to tomorrow’s tasks and enjoy the time I had with my family. 

Remember, the system is all about focus and simplicity and not more work.

Habit tracking through Pillars has allowed me to accomplish things I’ve been talking about doing for too long. One of the other real benefits is that it has allowed me to be present and actually enjoy what I’m working on at that moment. 

Before I would get frustrated that I was working on something when I really wanted to be working on what I was dreaming of—knowing deep down that I wouldn’t be working on that either—and that’s where the real frustration lied. But now I am working on those dream projects and seeing rapid growth. I also know that these Pillars will eventually become habits and part of my daily routine which will allow me to create and conquer new Pillars. I may actually learn how to play guitar one day. 

If you thought learning new habits was hard, see what happens in my next post where I’m forced to think of myself as a brand, a logo and just a few adjectives. 

Here’s a preview — I literally made myself look like a dick. 

Why I Started the Blog

As a sales and marketing person, my job is to tell a compelling story to engage existing and prospective clients and have them want to work with and buy from me. I have been going about this for years in the traditional sense by knocking on doors, making cold calls, attending industry meetings and networking. It worked well for me—I made decent money and won some awards—but it clearly wasn’t going to be enough to help me take my sales and career to the next level. 

For the past six months I’ve had a nagging feeling that I wasn’t doing enough to stand out, so I started writing some stories about my company’s products and systems. My goal was to create enough content to put on a blog and share with my current and potential customers. This is not an original idea but I finally decided to pursue it after reading and hearing countless stories on podcasts from popular sales and business gurus like, Gary Vaynerchuck, Anthony Iannarino and Dorie Clark. They kept preaching the need to differentiate yourself from your competitors and I finally felt compelled to make a change. The pandemic is making me realize how crucial this is.

One of my main reasons for a change was to improve my writing skills for future career goals and to reignite a creative side of me that I felt had been missing. My customers also needed to see something different from me, something that showed how I cared about their businesses and could help them increase patient compliance and revenue with my company’s products and systems. 

But I hadn’t imagined just how much writing and researching these posts would help me.

I gained a better understanding of my products and the customer’s needs for them. I was connecting with my customers on a deeper level by really talking to them about their business, obtaining quotes from those who have been successful using our systems and was able to drive more new customers to our programs.

The other learning part of this experience has been creating my own website through WordPress.com. Developing the WordPress site brought back incredible memories of an earlier project in my marketing career. I was the lead project manager for the creation and launch of the WordPress site Hu-FriedyPerformance.com, an interactive product demonstration module for distribution reps to use and help secure sales. It was really eye opening to see how different departments thought a tool like this should work. I was working with product managers, our sales team, distribution sales reps and an outside vendor. This project gave me deeper insight into how my company and industry worked as a whole and the hurdles a manufacturing company must go through to gain the attention of distribution reps and customers. 

Working on the website with both my future and that of my customers in mind also has me thinking about all of the new things I’ll learn and the endless opportunities to uncover, such as using the blog posts to expand my presence on social media, turning posts into scripts for videos, learning more about SEO, and generally increasing my digital marketing engagement.

Looking toward the future and remembering the past has allowed me to conceptualize a career path that is more than just sales. My goal is to one day lead a sales and marketing team and show how they can combine sales and marketing skills in the field to better connect with and find customers they didn’t know existed. 

The process of writing the blog posts and developing the WordPress site provided me more enjoyment in my career than I’ve had in a while and gave me a new outlook on my future. Of course, that future is a little more unstable—but it’s one where I’ll be better positioned on my career path thanks to my new website, jassonddempsey.com.

How I Became a Writer

How many times have you created a goal and never achieved it? We’ve all done it. Most of us set new goals every January and by March we know that we’re not going to achieve them.

In January I set a goal to start writing a blog. My goal for the blog was to help me become a better a writer, create content for my customers and increase my visibility on social media for new opportunities. If you’re reading this piece on my new website jasonddempsey.com and asking yourself, “Well, you did it, so what’s the problem?” 

The problem was that I made the exact same goal in 2019 and didn’t write a damn thing.

What could I do to make sure that 2020 was not going to be a repeat of 2019?

I first needed to determine what went wrong last year. I set the goal to start a blog to use as a tool to share product stories and gain meetings and sales with my customers. I came up with a lot of good ideas but never really wrote much.

So what could I do? Luckily for me I found a book that said you shouldn’t set goals. Problem solved.

The New Year can’t officially start until you’ve made your resolutions and purchased a new self-help book. After doing some research it seemed the options were to Unfu*k Yourself or Start Building Good Habits. I went with the latter because it talked about not setting goals and focusing on a system, and I already had a therapist for the former. The book I’m referencing is “Atomic Habits” by James Clear

Early in the book, I was really struck by what the writers refers to as the three layers of behavior change: a change in outcome, a change in your process, or a change in your identity. Outcomes are concerned with the results, process revolves around habits, and identity is concerned with your self-image. Clear states that identity is the true behavior change and the only reason you’ll stick with a new habit is if it becomes part of your identity. If I wanted to be successful this year then my goal shouldn’t be to start a blog but to become a writer. That was an identity I hadn’t considered.

The more I thought about it the more it made sense. Becoming a writer didn’t have to mean becoming an award winning author, but if I wanted a blog where I consistently put out quality content then I would need to act and work like a writer to see myself as one. So I needed to write more to be a writer but the lack of writing is mostly what held me back in 2019. I was confident in my ideas for blog topics and the overall approach of how it would help me and my customers, but I only thought of myself as a decent writer who could use some help with grammar. I would also need some tips on writing a blog for business. 

I discovered “Everybody Writes” by Ann Handley with a simple Google search for books on business writing. This book seemed to be on everyone’s best of list and after a quick read on her website I knew it was the book for me. Ann talked about how everyone was already a writer because of emails and social media and even though I did those things I didn’t feel like a writer. But it was her approach to writing that showed me I could be one. She emphasized how a good piece or writing was assembled and not written. She outlined how to put the blog post together with instructions and even recommended not doing it all in one sitting. 

Armed with this new outline, other solid writing tips and no pressure to feel I had to write a masterpiece in one sitting I didn’t feel as overwhelmed. Maybe I could be a writer? The next writing expert helped me put the final pieces of my writing identity puzzle together and also provided some unexpected business advice.

Dorie Clark has appeared on a few podcast episodes that I’ve listened to so I was familiar with her story — a story that many of us find ourselves in today due to the COVID-19 pandemic. She was let go from her journalism job around 9/11 and had to find a way to re-invent herself and make money. She decided that she needed multiple revenue streams and even wrote a book titled “Reinventing You.” I didn’t read the book but instead took the online course on her website called, “Rapid Content Creation Masterclass.” 

The course became the perfect set of instructions I needed for writing a business blog. She simply gave me all the rules I needed to follow to write a blog post. There were helpful tools for creating topics, testing the title’s strength, and ways to bolster each paragraph. The Rapid Content Creation Masterclass allowed me to create my own blog writing template that made it easy for me to sit down and finally start writing—a template that I one day plan to refine so I can share with others who would like to start a blog to help their sales career or business.

Even though I made myself an easy-to-use template and the writing seemed to be coming more naturally I just wasn’t writing enough—especially if I planned to put out content on a regular basis. You see, I had created an awesome template that helped me write but I still didn’t have a system that would make me a writer. 

Next up is my post on creating a plan around my new schedule that helped me find the time to become a writer and discover an even more important identity.

I Needed a New Plan

My writing habits were improving but I wasn’t writing enough. Potential blog posts were being worked on but not completed. I’d schedule time to write but when the time came I’d usually just focus on other things for my job. 

These other things kept me busy but deep down I knew they didn’t have the long term potential for future gains and earnings that writing and the blog would provide. 

I really enjoyed the writing but the fear of what others would think was holding me back. 

When I was researching to become a better writer and develop better habits I noticed that all of the books, blogs and podcast had a similar message. Focus on the identity of who you want to be, establish the habits that type of person would have so you can start to see yourself in that light and find someone who will help to hold you accountable.

For me that meant, in order to view myself as a writer, I needed to consistently write to consider myself a writer and have someone to hold me accountable and help edit my writing. Luckily I married into a family of talented writers; my wife included. My sister-in-law Colleen is a published writer, former college writing professor and a director of marketing. She was perfect and most importantly, willing to help me out. 

I knew Colleen would provide me with constructive criticism, new ways to approach topics and the confidence to overcome my fear of appearing stupid. Soon after I was finishing posts and hitting my goal of one new draft a week.

Unfortunately the COVID-19 pandemic hit and now I was self-isolating at home with my wife and two sons under five. Since no one had anywhere to go I figured I’d have more time to write. I quickly realized that being home with two kids left me with less time than I had before. 

That’s not to say I didn’t have time to write I just needed to figure out when the best times were. 

My first inclination was that as long as my boys were being quiet then I could write. The younger one doesn’t stay quiet or still for less than ten minutes so that was a mistake. I just ended up getting irritated and blaming them for not writing as much. I knew it wasn’t their fault and I was starting to become pretty moody toward everyone. 

I needed to rethink my new situation as a whole because there were a lot of other things I wasn’t taking care of either. I wasn’t working out, doing household chores or enjoying the time I had been given with my wife and kids. I came to the sudden realization that there were certain times of the day that were better suited for certain tasks or projects.

To see how I could fit the projects into my new life I broke down the days into the natural time blocks our kids were dictating without factoring in anything that I wanted to do:

  • 6 – 8am: Boys wake up and get settled into morning 
  • 8-10am: Breakfast and playtime
  • 10-11am: Zoom school meetings
  • 11am — 12pm: Bike ride with the boys or destroy basement
  • 12-1pm: Lunchtime
  • 1-3pm: Youngest naps and older one has quiet time
  • 3-5pm: Playtime, outside time, practice numbers and letters
  • 5-7pm: Family and dinner time
  • 7-8pm: Boys go down for bed
  • 8-10pm: Relax and hang out with my wife

Now that I had the day broken down into its natural flow I could see what times were best suited for certain projects and allow me to be present for my family. I made a list of what I wanted to accomplish during the week: writing, developing website, working out, household chores, learning/research and my own personal downtime. Then I cross referenced those tasks with the daily schedule and started to put the new puzzle together (puzzles were a popular activity during the pandemic). 

  • 7-9am: Workout – My wife and I could switch off during this time. The morning is better for me because I lose all motivation to work out after 10am.
  • 9-11am: Learning/research or chores – This time was perfect to listen to podcasts, read books & blogs, or clean part of the house. The boys are pretty active during this time but I realized I could work on things that I could easily put down and walk away from. 
  • 11-1pm: Bike ride or playtime with boys and lunch together.
  • 1-3pm: Writing, web development or errands.
  • 3-8pm: Family time, chores and dinner.
  • 8-10pm: Time with my wife or open for tasks (Tiger King, The Last Dance, etc.)

Once I started following this new schedule I instantly saw better results in my projects and mood. I was enjoying my time with the boys, writing and reading more, working out, well the working out wasn’t happening as much but there were plenty of enjoyable bike rides. 

This new system simplified my days because I knew exactly when I could get certain things done. And if something didn’t happen on a given day I wasn’t angry because I knew I had the time tomorrow. 

However, when I looked back on my week I noticed that I was working on some things more than others. There really didn’t seem to be a proper balance for what I was working on. One morning listening to a sales podcast, at the designated time, I discovered a new system that would change everything. Check out the next blog on a system that showed me a way to feel balanced and fulfilled at the end of each day and week.