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.
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/ (https://coreinsurancela.com/)
Email:
john@coreinsurancela.com (mailto:john@coreinsurancela.com)
Core Insurance currently serves Louisiana, Texas and Florida.
13 Oct 2026
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 Group
Fletcher Financial Group:
https://fletcherfinancialgroup.net/ (https://fletcherfinancialgroup.net/)
Braden Smith on LinkedIn:
https://www.linkedin.com/in/braden-t-smith/ (https://www.linkedin.com/in/braden-t-smith/)
8 Oct 2026
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 Selling
Systematic Selling:
https://systematicselling.co/ (https://)
LinkedIn:
https://www.linkedin.com/in/seanmlyden/ (https://www.linkedin.com/in/seanmlyden/)
X:
https://x.com/seanmlyden (https://x.com/seanmlyden)
Systematic Selling Newsletter & Podcast:
https://systematicselling.co/ (https://)
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