Outside the Sale

Kyle Hessler
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Years on the road create more than customers and commissions. They create relationships, stories, lessons, friendships, missed flights, long drives, trade shows, dinners, unexpected conversations, and experiences that shape who you become. Hosted by Kyle Hessler, Outside the Sale explores the people, places, relationships, and experiences found somewhere between the miles and the margins. It’s about sales sometimes. But mostly, it’s about life outside the sale.

  1. 9h ago

    The Riches Are in the Niches | Josiah Stowe

    How does a small company compete when the giants have more money, more people, more name recognition, and bigger marketing budgets? 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. Connect with Josiah & Dominion Wealth StrategistsDominion Wealth Strategists: https://reformed.money/ Josiah Stowe on LinkedIn: https://www.linkedin.com/in/josiah-stowe/

  2. Oct 21

    The Business of Selling Insurance | John Carlson

    Everyone needs insurance. Almost nobody gets excited about buying it. 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.

  3. Oct 13

    Financial Planning Is a Sale for Life | Braden Smith

    What happens when the person you're selling to may remain your customer for the rest of their life—and your work could affect their children and grandchildren? 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. Connect with Braden & Fletcher Financial GroupFletcher Financial Group: https://fletcherfinancialgroup.net/ Braden Smith on LinkedIn: https://www.linkedin.com/in/braden-t-smith/

  4. Oct 8

    Stop Trying to Convince People to Buy | Sean Lyden

    What if great sales isn't about convincing people at all? 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. Connect with Sean Lyden & Systematic SellingSystematic Selling: https://systematicselling.co/ LinkedIn: https://www.linkedin.com/in/seanmlyden/ X: https://x.com/seanmlyden Systematic Selling Newsletter & Podcast: https://systematicselling.co/

  5. Oct 6

    Sales Resistance, Rejection & Knocking Doors | Dean Gadberry

    What does knocking on strangers’ doors teach you about sales? 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. Connect with Dean GadberryLinkedIn: https://www.linkedin.com/in/deangadberry/

  6. Oct 1

    Stop Counting Followers Start Building Relationships | Asher Dixon

    What matters more on social media: followers or relationships? 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. Connect with Asher & RedBalloonRedBalloon: https://redballoon.work/ LinkedIn: https://www.linkedin.com/in/asher-dixon/ X: https://x.com/_a_sage RedBalloon on X: https://x.com/RedBalloonWork

  7. Sep 29

    The Work of Building a Legacy | Brad Stafford

    What are you actually working to build? 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 BradSunset CMO: https://sunsetcmo.com/ Anyone Can Homeschool: https://anyonecanhomeschool.com/ LinkedIn: https://www.linkedin.com/in/brad-stafford-a0b8554/

  8. Sep 24

    Selling Sound: The Business of Guitar Pedals | Cody Fields

    What are you actually selling when your product is a sound? 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 EffectsWestminster 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

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About

Years on the road create more than customers and commissions. They create relationships, stories, lessons, friendships, missed flights, long drives, trade shows, dinners, unexpected conversations, and experiences that shape who you become. Hosted by Kyle Hessler, Outside the Sale explores the people, places, relationships, and experiences found somewhere between the miles and the margins. It’s about sales sometimes. But mostly, it’s about life outside the sale.

Information

  • Creator
    Kyle Hessler
  • Years Active
    2026
  • Episodes
    21
  • Rating
    Clean
  • Copyright
    © 2026 Kyle Hessler
  • Show Website
    Outside the Sale