Find a niche—and own it.

In this episode of Outside the Sale, I sit down with Josiah Stowe of Dominion Wealth Strategists, a small financial firm that has built its brand by doing something very different from the massive institutions it competes against.

Josiah and his business partner, Justin Johnson, deliberately focused Dominion on the Reformed Christian community. Instead of trying to market to everyone, they learned where their audience spends its time, how it communicates, and what gets its attention. That meant everything from sponsoring podcasts and conferences to becoming surprisingly good at financial memes.

And it worked.

Josiah explains why Dominion views podcasts as sowing and conferences as reaping: digital marketing creates familiarity, but face-to-face interaction can turn that awareness into trust and actual business. At one recent conference, they booked roughly 30 meetings in two days.

We talk about the advantages and disadvantages of being the little guy, why smaller companies can move faster, what happens when your marketing doesn't clearly differentiate you, and why sometimes you have to change your pitch in the middle of a trade show.

We also get into Dominion's actual sales process, including why Josiah teaches his agents to stop selling once the customer is sold. When a prospect asks, “What's next?” the sale is closed. Book the next meeting and stop talking.

And yes—we get into Dave Ramsey.

Quite a bit.

But underneath all of it is a bigger business lesson:

You don't have to be the biggest company in the market to compete. You have to know exactly who you're for and give them a reason to remember you.

Or, as Josiah puts it:

“The riches are in the niches.”

The Riches Are in the Niches | Josiah Stowe

This is Outside the Sale — conversations about what people sell, how they sell it, and everything that happens outside the sale.

Dominion Wealth Strategists:
https://reformed.money/

Josiah Stowe on LinkedIn:
https://www.linkedin.com/in/josiah-stowe/

In this episode of Outside the Sale, I sit down with John Carlson of Core Insurance to learn what the business of actually selling insurance looks like.

John works across both personal and commercial insurance, covering everything from home, auto and flood to businesses and investment properties. We break down how an independent insurance agency works, how brokers shop multiple carriers, and why having an actual agent can provide value beyond simply finding the lowest price.

John also has an interesting path into sales. He never considered himself a natural salesperson and initially avoided sales and commission-based work. But after he and his wife had their second child, they wanted to find a way for her to stay home. A conversation with his pastor led him to look for a career with more upside—and the very next day he saw an insurance agency looking for an agent. Three years later, he says he loves it.

We talk about building a book of business, cold calling versus referrals, cross-selling, renewals, personal versus commercial insurance, commissions, prospecting, and how John balances the reality that almost everyone is a potential customer without treating every person he meets like a prospect.

We also get into the difficult side of the business: rising insurance rates, carriers leaving markets, explaining premium increases to longtime customers, and why saving money isn't always worth sacrificing the coverage you'll need when something actually goes wrong.

And sometimes serving the customer means being willing to lose the sale. John talks about situations where he'll tell someone to shop elsewhere when he believes Core simply can't offer them the best option.

The Business of Selling Insurance | John Carlson

This is Outside the Sale — conversations about what people sell, how they sell it, and everything that happens outside the sale.

Connect with John & Core Insurance

Core Insurance:
https://coreinsurancela.com/

Email:
john@coreinsurancela.com

Core Insurance currently serves Louisiana, Texas and Florida.

In this episode of Outside the Sale, I sit down with Braden Smith of Fletcher Financial Group to explore what may be one of the most personal forms of B2C sales: financial advising.

A financial advisor isn't simply asking someone to buy a product. Clients may eventually trust them with their income, investments, retirement plans, insurance needs, estate planning, major life decisions, and what happens to their wealth after they're gone.

Braden describes what Fletcher Financial Group sells simply: a plan. Their approach is built around “wealth for life and beyond”—planning for the client's life today while also considering where that wealth goes afterward. braden-kyle

We talk about how an advisor earns that level of trust, why Fletcher moved away from investment minimums, educating clients who have spent a lifetime working but may know very little about investing, and why a good advisor sometimes has to tell clients hard truths. braden-kyle

We also get into multigenerational wealth and financial literacy. Braden talks about serving financial middle America and helping ordinary families think about how today's decisions can allow the next generation to stand on their shoulders—and potentially change their family tree. braden-kyle braden-kyle

And we explore an interesting tension in Braden's job: Is he a salesperson or a financial advisor? His answer is really both. Sales gets the relationship started, but the real work begins after the client says yes. braden-kyle

Because in financial planning, a successful sale isn't supposed to last until the transaction is finished.

It could last for life.

This is Outside the Sale — conversations about what people sell, how they sell it, and everything that happens outside the sale.

Fletcher Financial Group:
https://fletcherfinancialgroup.net/

Braden Smith on LinkedIn:
https://www.linkedin.com/in/braden-t-smith/

In this episode of Outside the Sale, I sit down with Sean Lyden, founder of Systematic Selling, to talk about his no-pressure, systematic approach to sales.

Sean entered the automotive industry with zero professional sales experience and describes himself as an introvert—not exactly the stereotypical personality people picture when they think “salesman.” Within a few years, he was ranked among the top 25 in the country in medium-duty GMC truck sales. He credits much of that success to learning inside a dealership built around strong systems, training, accountability, and a no-pressure approach.

That experience helped shape a philosophy Sean still teaches today:

Sales isn't about convincing someone to buy. It's about finding alignment between the customer's problem and your solution.

If there's alignment, move forward. If there isn't, don't force the sale.

We talk about whether great salespeople are born or made, why introverts can have an advantage in sales, following a process without becoming robotic, relationships versus systems, firing bad-fit customers, founder-led sales, prospecting, closing, and why everyone in a company is ultimately involved in sales.

Sean also explains why the customer isn't necessarily always right—but the customer is the paycheck—and why sales and operations have to work together if you want to build a company customers continue doing business with.

And maybe the best summary of Sean's philosophy:

You don't need high-pressure tactics to be a killer in sales.

This is Outside the Sale — conversations about what people sell, how they sell it, and everything that happens outside the sale.

Systematic Selling:
https://systematicselling.co/

LinkedIn:
https://www.linkedin.com/in/seanmlyden/

X:
https://x.com/seanmlyden

Systematic Selling Newsletter & Podcast:
https://systematicselling.co/

In this episode of Outside the Sale, I sit down with my friend Dean Gadberry, now an Inside Sales Representative at Triple-S Steel, to talk about one of the toughest forms of selling: door-to-door sales.

Dean spent time selling internet door-to-door for Spectrum before recently making the move into inside sales in the steel industry. We compare those two worlds and talk about the grind of knocking doors, the loneliness that can come with it, handling rejection, and why door-to-door can be an incredible training ground for salespeople.

Dean also breaks down the idea of sales resistance—the natural tendency people have to filter out the constant stream of people, advertisements, and messages trying to sell them something. From there, we get into trust, certainty, objections, and what it takes to get someone to actually listen when their first instinct is to say no.

But the conversation eventually goes deeper than sales techniques. We talk about the difference between actually being trustworthy and simply learning how to appear trustworthy, sincerity versus honesty, reading people, and learning how to communicate with people from completely different walks of life.

For Dean, door-to-door wasn't just where he learned how to sell. The sheer volume of conversations, rejection, and uncomfortable interactions helped him become more resilient and ultimately better at talking to people.

Whether you've knocked thousands of doors or never made a cold call in your life, there's a lot here about what rejection can teach you—and why getting uncomfortable can make you a better salesperson.

Sales Resistance, Rejection & Knocking Doors | Dean Gadberry

This is Outside the Sale — conversations about what people sell, how they sell it, and everything that happens outside the sale.

LinkedIn:
https://www.linkedin.com/in/deangadberry/

In this episode of Outside the Sale, I sit down with Asher Dixon, Marketing Director at RedBalloon, for a conversation I've wanted to have since starting the podcast: where does marketing end and sales begin?

The idea started with the scene from Skyfall where James Bond meets Q. Q can accomplish an incredible amount sitting behind a computer. Bond still has to go into the field and get the job done.

That's not a bad picture of sales and marketing.

Asher has helped build social audiences reaching tens of thousands of people, but he shares an important lesson RedBalloon learned along the way: attention doesn't necessarily equal sales. At one point, people knew the brand and loved the content—but didn't necessarily know what RedBalloon actually sold.

We talk about why LinkedIn is different from other social platforms, personal brands versus company brands, why salespeople should create content, what marketing can learn from salespeople in the field, the danger of chasing trends, and why the right 10 leads can be worth far more than a viral post.

Asher's larger point is simple: stop treating views, followers, calls, and emails as the ultimate goal. Build relationships. Sales and marketing are both parts of that process—and the best companies get them working together.

We even get into AI, why Asher prefers starting with a blank page, and his belief that writing is one of the best ways to force yourself to actually think.

Stop Counting Followers. Start Building Relationships. | Asher Dixon

This is Outside the Sale — conversations about what people sell, how they sell it, and everything that happens outside the sale.

RedBalloon:
https://redballoon.work/

LinkedIn:
https://www.linkedin.com/in/asher-dixon/

X:
https://x.com/_a_sage

RedBalloon on X:
https://x.com/RedBalloonWork

In this episode of Outside the Sale, I sit down with Brad Stafford, founder of Sunset CMO and co-founder of Anyone Can Homeschool, for a conversation that started with marketing and sales but quickly became something bigger: legacy.

Brad has spent roughly two decades in digital marketing, advertising, copywriting, and consulting. But years ago, when a successful client tried to bring him in-house, Brad was faced with an interesting question: How much is your time actually worth?

His answer eventually became $5 million.

Not because the job wasn't good, but because when that Thursday afternoon call ended, Brad was going to the pool with his kids. His client still had hours left at the office followed by a commute home. Brad knew taking the opportunity would mean trading something he valued more than the paycheck: time with his family.

That story leads us into a much broader conversation about work, fatherhood, homeschooling eight children, integrating children into the family economy, financial inheritance, entrepreneurship, remote work, and intentionally building something that can last for generations. Brad talks about viewing both opportunity and family as blessings that come with responsibilities—and his desire to build a family culture his children will actually want to continue.

We also get into Brad's work at Sunset CMO: the relationship between creativity and data in modern marketing, understanding what customers actually respond to, knowing when to turn down a client, why reputation beats a résumé, what cold leads can teach you, and why sometimes a consultant has to be willing to tell a client that what they're doing simply isn't working.

And eventually we take the idea of work all the way to retirement—or Brad's rejection of it. For him, the goal isn't to work hard enough that one day he can stop being productive. It's to keep working, contributing, teaching, and building for as long as he's able.

A career can make you money. The bigger question is what your work is building after you're gone.

This is Outside the Sale — conversations about what people sell, how they sell it, and everything that happens outside the sale.

Connect with Brad

Sunset CMO:
https://sunsetcmo.com/

Anyone Can Homeschool:
https://anyonecanhomeschool.com/

LinkedIn:
https://www.linkedin.com/in/brad-stafford-a0b8554/

In this episode of Outside the Sale, I sit down with Cody Fields, founder and president of Westminster Effects, to talk about the business behind guitar pedals—and what it's like selling to musicians.

Cody started Westminster Effects in 2015 after building a single pedal kit and deciding he had some ideas of his own. Today, Westminster builds distinctive guitar effects that combine high-quality gear with an unmistakable brand rooted in church history.

But selling guitar gear presents an interesting challenge. Musicians aren't simply buying a box with electronics inside it. They're chasing a particular tone, aesthetic, and creative possibility. As one of Cody's artists put it, he sells boxes that help “unlock people's creativity.”

We talk about selling to notoriously particular musicians, why gear nerds can actually be great customers, building the product before the brand, dealers and distribution, artist endorsements, trade shows, marketing niche products, and why Cody would rather reach the right 1,000 people than get a million views.

Cody also tells the story of how a connection eventually led to a friendship with Seth Morrison of Skillet and the creation of Westminster's 2716 signature distortion pedal—designed to put Seth's massive live guitar tone into a pedal an everyday guitarist can actually afford.

This one's about guitars, but it's really about building a niche product, finding your customer, and figuring out how to sell something as subjective as sound.

This is Outside the Sale — conversations about what people sell, how they sell it, and everything that happens outside the sale.

Connect with Cody & Westminster Effects

Westminster Effects:
https://westminstereffects.com/

LinkedIn:
https://www.linkedin.com/in/cody-fields-17326536

Instagram:
https://instagram.com/westminstereffects

Facebook:
https://facebook.com/westminstereffects

X:
https://x.com/WestminsterFX

TikTok:
https://www.tiktok.com/@westminstereffects

Doxology Podcast:
https://westminstereffects.com/pages/doxology-podcast

In this episode of Outside the Sale, I sit down with Greg Moore, a longtime salesman, real estate broker, county commissioner, and host of the Dead Men Walking Podcast, for a free-flowing conversation about curiosity, relationships, and recognizing opportunities other people miss.

Greg has been selling since he was a kid. One of his earliest experiences was working his father's computer wholesale business, where he learned to get out from behind the booth, talk to people, listen, and create opportunities instead of waiting for customers to come to him.

Years later, that same instinct led to one of the biggest sales of his career.

While working for AT&T, Greg started talking with a customer who was having an issue with his phone. Instead of stopping once the problem was solved, Greg simply asked what he did for a living. That conversation eventually uncovered an opportunity with the new Hollywood Casino in Toledo—and led to a $5 million communications deal.

We talk about why great salespeople are naturally curious, building value without making someone feel like they're being closed, trade shows, networking with competitors, selling to government, real estate, podcasting, and why some of your best long-term customers can come from asking a simple question:

“How can I help you?”

Greg's career has taken him through completely different industries, but the fundamentals keep showing up: ask questions, listen, solve problems, build relationships, and recognize opportunities when they're standing in front of you.

This is Outside the Sale — conversations about what people sell, how they sell it, and everything that happens outside the sale.

Connect with Greg Moore:

Dead Men Walking Podcast:
https://dmwpodcast.com/

In this episode of Outside the Sale, I sit down with Larson Hicks, CEO of Sycamore Independent Physicians, for a free-flowing conversation about sales, incentives, relationships, and the business behind American healthcare.

Larson operates in the world of locum tenens, connecting independent physicians with healthcare organizations that need doctors. That means Sycamore is essentially selling on both sides of the transaction—winning healthcare organizations as clients while also recruiting physicians and earning their trust.

We talk about why Larson believes healthcare has become increasingly transactional, how Sycamore built a different model around transparency and relationships, and why the way you structure incentives can completely change people's behavior. Larson explains that Sycamore's model actually allows the company to make more when its physicians make more—aligning their interests instead of rewarding recruiters for squeezing physician pay.

We also get into selling to hospitals, trade shows, recruiting versus sales, healthcare bureaucracy, physician independence, commission structures, customer service, work ethic, and why good salespeople will inevitably figure out how to maximize whatever incentive system you put in front of them.

It's a conversation about healthcare, but it's also about a much broader business principle: you get more of what you incentivize.

This is Outside the Sale — conversations about what people sell, how they sell it, and everything that happens outside the sale.

Connect with Larson:

Sycamore Independent Physicians:
https://sycamoredocs.com/

LinkedIn:
https://www.linkedin.com/in/larsonhicks

In this episode of Outside the Sale, I sit down with my good friend Ryan Ray from Ad Astra Equity Advisors for a free-flowing conversation about relationships, referral networks, sales strategy, and building a reputation people remember.

Ryan breaks down one of the simplest—and most useful—sales frameworks I've heard: the right offer, to the right prospect, at the right time. We talk about why timing matters so much, how to stay in front of people without constantly pitching them, and why building genuine relationships can create opportunities that cold outreach never will.

We also get into Ryan's approach to building referral networks, using social media to tell stories and stay top of mind, selling yourself without pretending to be someone you're not, and how the M&A world changes the traditional sales process.

Ryan even gives us his actual pitch, explains how he continually improves it based on how prospects respond, and breaks down his “five-wide” approach to balancing dependable sales opportunities with the occasional home-run opportunity.

And because Ryan and I are good friends, we eventually end up debating Hulk Hogan vs. Macho Man, Shaq vs. Kobe, who the better salesperson is—and I may or may not call him Brian before the episode ends.

This is Outside the Sale — conversations about what people sell, how they sell it, and everything that happens outside the sale.

Connect with Ryan:

Ad Astra Equity Advisors:
https://adastraequity.com

LinkedIn:
https://www.linkedin.com/in/ryanraysr/

In this episode of Outside the Sale, I sit down with Andy Parker, author of Long Live the Patriarchy: Why God Made Fathers, for a free-flowing conversation about fatherhood, work, responsibility, masculinity, and what men are supposed to build.

Andy grew up without his father and eventually found himself wrestling with what it actually means to become a father, lead a family, and take responsibility for something bigger than yourself. We talk about his belief that biblical patriarchy is not about domination, but the glad assumption of responsibility.

We also get into why work is good, why our children need to see us work, raising boys, bringing your kids into your professional life, character and trust in sales, strength and self-control, and the difference between simply having a job and understanding your work as part of a much larger calling.

Because at the end of the day, a man’s work is bigger than his job.

This is Outside the Sale — conversations about what people sell, how they sell it, and everything that happens outside the sale.

Connect with Andy / Find the Book:
Long Live the Patriarchy: Why God Made Fathers
by Andy Parker

In this episode of Outside the Sale, I sit down with Tom Chaldecott from Knox Thomas for the show's first international conversation.

Tom works in machinery safety and compliance, but as his company has grown, he's realized that a huge part of his role as founder and CEO is really sales and marketing. We talk about what selling looks like in the UK, how British attitudes toward sales differ from American ones, and what both sides can learn from each other.

Tom shares why a more understated, low-pressure approach has worked for him, while also explaining what he admires about American work ethic, competitiveness, incentives, and customer service. We get into the difference between being assertive and being pushy, why great service can be a competitive advantage, and why sometimes simply doing what you said you would do is enough to stand out.

We also talk about building Knox Thomas, selling technical expertise, giving valuable tools away for free, using AI to make the company more efficient, and why a salesperson needs to be comfortable saying, “I don't know, but I'll find out.”

This is Outside the Sale — conversations about what people sell, how they sell it, and everything that happens outside the sale.

Connect with Tom:

LinkedIn:
https://www.linkedin.com/in/chaldecott/

Tom's Substack:
https://tomchaldecott.substack.com/

Knox Thomas:
https://knoxthomas.co.uk/

In this episode of Outside the Sale, I sit down with Nathan Hansen from Smith System Driver Improvement Institute for a free-flowing conversation about sales, AI, human intuition, relationships, and what actually makes a great salesperson valuable.

Nathan's argument is simple: AI competes with mediocrity, not excellence. If your job is simply pounding the phones, sending generic emails, or taking orders, AI may eventually do those things faster and cheaper. But great salespeople do something much harder—they understand people.

We talk about why customers often don't actually know what they need, and why a salesperson's job is sometimes to diagnose the problem before they can sell the solution. Nathan compares a good salesperson to a good therapist: listening, asking the right questions, drawing on experience, and making intuitive connections the customer may never have considered.

We also get into selling risk reduction, treating customers like human beings, why the things that don't scale can sometimes be the most valuable, and how salespeople should use AI as a tool rather than fear it as a replacement.

And, naturally, we somehow end up discussing everything from collision avoidance and handwritten notes to whether businesses are just strapping jet engines onto horse-drawn buggies.

This is Outside the Sale — conversations about what people sell, how they sell it, and everything that happens outside the sale.

Connect with Nathan:
https://www.linkedin.com/in/nathan-hansen-87752990/

In this episode of Outside the Sale, I sit down with Jackson Crapuchettes from MilitaryHire for a free-flowing conversation about the connection between marketing and sales—and why getting someone's attention is only the beginning.

Jackson spent about four years on the creative side of RedBalloon before moving into a more sales-focused role. We talk about what he's learned making that transition, overcoming objections, reading the person in front of you, and why you can't always force someone into becoming a good customer.

We also get into the difference between attracting a big audience and attracting the right audience. As Jackson puts it, marketing speaks to a broader group of people, while sales becomes personal. The goal isn't just views, clicks, or attention—it's getting the right people into the sales funnel.

Along the way, we talk about RedBalloon, MilitaryHire, hiring veterans, branding, company culture, building trust, knowing when to push through an objection, and when it's better to walk away.

This is Outside the Sale — conversations about what people sell, how they sell it, and everything that happens outside the sale.

Connect with Jackson:
https://www.linkedin.com/in/jackson-crapuchettes-8775711b0/

MilitaryHire:
https://www.militaryhire.com/

RedBalloon:
https://www.redballoon.work/

I sit down with military defense attorney and former Air Force JAG Davis Younts for a free-flowing conversation about why even highly trained professionals have to learn how to sell.

Davis talks about starting his own law practice and realizing that expertise alone doesn't bring clients through the door. We get into building trust, listening before pitching, knowing when not to make the sale, and how the same skills used in sales show up when you're trying to persuade a client, a jury—or even a room full of Navy SEALs.

We also talk about how Davis's Christian faith shapes the way he approaches his clients and his business, why integrity matters more than closing every deal, and why sales, done the right way, ultimately comes down to understanding someone's problem and helping them find the right solution.

From the courtroom to running a law firm, this is a conversation about persuasion, relationships, service, and why almost everyone has something they're selling.

This is Outside the Sale — conversations about what people sell, how they sell it, and everything that happens outside the sale.

Connect with Davis Younts:

Younts Law:
https://yountslaw.com/

Instagram:
https://www.instagram.com/davisyounts_attorney/

X:
https://twitter.com/DavisYounts

Facebook:
https://www.facebook.com/MilitaryDefenseAttorney/

Actually, it was their robot that caught my attention.

Michael is the founder of NXT LVL EVENT, an experiential marketing company that helps brands stand out at trade shows and events through interactive experiences, AI, robotics, photo and video activations, and data collection.

We talk about Pixie, the roaming robot that stopped me in the aisle, Bot Ross, using experiences to generate leads, and one of the biggest challenges at any trade show: how do you make people actually remember you?

A quick, completely spontaneous conversation from the trade-show floor.

This is Outside the Sale — conversations about what people sell, how they sell it, and everything that happens outside the sale.

NXT LVL EVENT:
https://www.nxtlvlevent.com/

We recorded this one in Houston after our first day together at PWX. Jared and I talk shop about trade shows, building customer relationships, networking without overselling, working with competitors, and some of the lessons we've both picked up through our careers in outside sales.

Jared also talks about his previous sales experience, stepping into his new role representing Capital StreetScapes and ACP International products, and what he's looking forward to as he takes what he's learned in past roles into a new industry.

This is Outside the Sale — conversations about what people sell, how they sell it, and everything that happens outside the sale.

I sit down with professional wrestler Jay Alexander for a free-flowing conversation about selling yourself, building a brand, reading the room, professionalism, and what it takes to make people believe in what you're selling.

Jay trained under WWE Hall of Famer Booker T at Reality of Wrestling and is a two-time ROW Texas Champion. We also go back to my days promoting professional wrestling, when Jay was one of the stars of Pale Pro Wrestling.

From getting booked—and getting booked again—to understanding your audience, there are a lot more similarities between professional wrestling and sales than you might think.

This is Outside the Sale — conversations about what people sell, how they sell it, and everything that happens outside the sale.

Connect with Jay:

Facebook
https://www.facebook.com/officialjayalexander/

Instagram
https://www.instagram.com/jayalexanderpw/

Reality of Wrestling:
realityofwrestling.com

I sit down with Caleb Gordon, Business Development Executive for The Nine Minds Group, for a free-flowing conversation about sales, relationships, mindset, leadership, and learning to influence the environment around you instead of simply reacting to it.

We talk about Caleb’s approach to business development, the importance of genuinely connecting with people, and some of the lessons he’s learned along the way.

This is Outside the Sale — conversations about what people sell, how they sell it, and everything that happens outside the sale.

Connect with Caleb:

The Nine Minds Group
https://thenineminds.com/

Caleb Gordon
https://www.calebgordon.org/

Facebook
https://www.facebook.com/caleb.gordon.930424/

LinkedIn
https://www.linkedin.com/in/caleb-gordon-5b229719a/

Welcome to the first episode of Outside the Sale.

I'm Kyle Hessler, and I've spent more than 12 years in outside sales. In this first episode, I introduce what I want this podcast to become and share a few of the principles that have shaped the way I approach sales.

At the center of it is relationships. I often say that I work for my company 50% of the time and my customer the other 50%. A good salesperson has to understand both sides, advocate for the customer when necessary, represent the company well, and recognize that sometimes the biggest value you can provide is simply making your customer's life easier.

I also get into why I don't think people actually hate salespeople—they hate bad salespeople—and share a real example of a prospecting message that demonstrated exactly what not to do.

This first episode is intentionally a little rough around the edges. I'm learning the equipment, figuring out the format, and getting the reps in. That's part of the point. Outside the Sale is going to grow by doing.

Thanks for joining me at the beginning.