legal tips for small businesses Archives

Sam Vander Wielen smiling and wearing a blue denim shirt. Text overlay reading “I Declared a Gap Year. Then I Turned It Into a Full-Time Job. [Summer Read-Aloud]"

I Declared a Gap Year. Then I Turned It Into a Full-Time Job. [Summer Read-Aloud]

August 3, 2026

Listen on Apple | Spotify | YouTube Listen Now: What happens when you give yourself an entire year off and can’t actually take it? That’s the question I’m sitting with in this week’s essay. I declared 2026 my entrepreneurial gap...

Sam Vander Wielen sitting, smiling and holding a microphone. Text overlay reading "How I Stopped Letting the Algorithm Decide What I Like"

How I Stopped Letting the Algorithm Decide What I Like [Summer Read-Aloud]

July 27, 2026

Listen on Apple | Spotify | YouTube Listen Now: I recently stood in a long line for pancakes I wasn’t even sure I wanted. And it made me realize how much of what I consume, eat, buy, watch, isn’t actually...

Sam Vander Wielen sitting on the beach and smiling. Text overlay reading "15 Habits that Rebuilt Me After I Lost Everything"

15 Habits that Rebuilt Me After I Lost Everything [Summer Read-Aloud]

July 20, 2026

Listen on Apple | Spotify | YouTube Listen Now: One of the strange gifts of your life completely burning to the ground is the fertile soil it leaves behind for you to begin again. That’s where I found myself after...

Sam Vander Wielen sitting indoors and writing in a notebook. Text reads: More Memories of Other People's Lives Than Our Own

More Memories of Other People’s Lives Than Our Own [Summer Read-Aloud]

July 13, 2026

Listen on Apple | Spotify | YouTube Listen Now: Nobody talks about what actually happens after you put your phone down. Everyone’s obsessed with the getting off social media part — deleting the apps, doing the digital detox, bragging about...

Sam Vander Wielen sitting on the beach. Text overlay reads "I Took a Whole Month Off and Didn't Tell a Soul — Here's What Happened."

296. I Took a Whole Month Off and Didn’t Tell a Soul — Here’s What Happened.

July 6, 2026

Listen on Apple | Spotify | YouTube Listen Now: I’m taking a little summer break, not just from the podcast, but from working in general. And yes, my friends are already cackling about that one, because as my friend Steve...

Sam Vander Wielen sitting indoors and smiling and with text overlay reading "I Went to Craft + Commerce. Here's Everything I Learned."

295. I Went to Craft + Commerce. Here’s Everything I Learned.

June 29, 2026

Listen on Apple | Spotify | YouTube Listen Now: If you’ve ever wondered what it’s actually like to attend one of the best conferences in the online business space, I’m bringing you along this week. Every June, I pack my...

Sam Vander Wielen writing in a notebook. Text overlay reads "Why 'Must Be Nice' Is the Most Dangerous Thing You Can Say to Yourself"

294. Why ‘Must Be Nice’ Is the Most Dangerous Thing You Can Say to Yourself

June 22, 2026

Listen on Apple | Spotify | YouTube Listen Now: “Must be nice.” It sounds harmless. Like a throwaway comment, a passing thought, something you mutter when you see someone doing something you wish you could do. But I’ve been thinking...

I've Sold M in Digital Products. Here's My Honest Take on the Market Right Now

293. I’ve Sold $9M in Digital Products. Here’s My Honest Take on the Market Right Now

June 15, 2026

Listen on Apple | Spotify | YouTube Listen Now: Everyone keeps coming up to me like they’re attending my business’s funeral. “How are things?” And I’m standing there like… everything’s actually great? My business keeps growing. But I get it....