How to Sell with Humor and Choose to Make Everyone Feel Good!

How to Sell with Humor and Choose to Make Everyone Feel Good!

Author: Dorien Morin-van Dam October 2, 2025 Duration: 31:48

If selling makes you cringe, or if you’ve ever tried to 'build rapport' and accidentally made things weirder, this one’s for you. Whether you’re pitching a product or service, or just your own ideas, adding humor can be your secret advantage.

In this episode of Strategy Talks, you’ll learn how to sell without sounding salesy, how to make people laugh without losing the sale, and why humor might be the best trust-builder you’re not using yet.

This week, Chris Castanes joins us with stories, strategies, and just the right amount of sarcasm.

★★★★★

Chris Castanes started selling when he was in grade school. His first job was selling door-to-door insurance policies in rural North Carolina. In 2009 he started what eventually became Surf Financial Brokers. In 2019 he began making plans to make his company more "virtual" and covid accelerated that.  

★★★★★

Strategic Thinkers. 

Expert Insights. 

Strategy Talks.

Join Dorien Morin-van Dam every Tuesday at 8 AM ET on LinkedIn, Facebook, and YouTube for 'Strategy Talks,' where she dives into the latest insights on business, AI and marketing strategies!

★★★★★ 

Resources:

Dorien on LinkedIn

Books by Chris Castanes:

Nearly Motivated

You Are Going To Be Great at This

Website: Chris Castanes

Strategy Talks | Season 1 YouTube Playlist: https://bit.ly/3veW5re

Strategy Talks | Season 2 YouTube Playlist: https://bit.ly/3YbXet0

Strategy Talks | Season 3 YouTube Playlist: https://bit.ly/3O5JlK8

Strategy Talks | Season 4 Youtube Playlist:  https://bit.ly/3WVPUUg


Dorien Morin-van Dam knows what it's like to build a content engine without a massive budget or staff. In Strategy Talks: Content Strategy for Small Teams, she brings that practical, hands-on perspective to every conversation. This isn't about abstract theory; it's a direct line to operators who are in the trenches, sharing the specific, repeatable plays they use to turn thoughtful content into genuine business pipeline. Designed for founders, small teams, agencies, and solo consultants, each half-hour episode is tightly focused. You'll find discussions rooted in one of three critical areas: the fundamentals of content strategy and planning, the nuts and bolts of distribution and SEO, or the practical application of AI for content operations. The goal is always clarity-first, by defining a common problem many face, and then by unpacking a tangible solution. Listening to this podcast feels like having a seasoned strategist in your corner, cutting through the noise to deliver actionable insights you can apply almost immediately. If you're responsible for content but short on resources, these conversations provide the structured thinking and tactical advice to make your efforts more effective and less chaotic.
Author: Language: English Episodes: 100

Strategy Talks: Content Strategy for Small Teams
Podcast Episodes
From Content to Comments to Customers: The Growth Power of Social Care [not-audio_url] [/not-audio_url]

Duration: 31:06
Here’s the uncomfortable truth: most of your content, the content you’ve spent time researching and creating… is going nowhere.You are posting, people are liking, maybe even commenting, but it’s not turning into real rel…
AI Visibility: How to Show Up in LLMs Without a Big SEO Budget [not-audio_url] [/not-audio_url]

Duration: 39:39
Search is changing fast. ChatGPT, Perplexity, Google SGE—your future customers are asking questions in tools that skip the traditional click. So how do small teams stay visible in a world where links are disappearing?In…
What Leaders Get Wrong About Content Strategy (And How to Fix It) [not-audio_url] [/not-audio_url]

Duration: 36:42
If your team’s content is unclear, inconsistent, or just not getting (enough) traction, it might not be a content problem but a leadership problem. Ahem. You!It's you; you might be the problem.Join executive coach Lori B…