On Your Terms®

Hosted by Sam Vander Wielen

Business Entrepreneurship

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310

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Aug 2026

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About the show

A podcast for online business owners who refuse to choose between revenue and a real life. Most business advice tells you to hustle harder, post more, and "always be on." I'm here to tell you that's BS—and I have the multi-seven-figure business to prove it. I'm Sam Vander Wielen, and I've built a thriving online business while protecting my mornings, unplugging at night, and actually living the life I built my business for. Every week, I share the marketing strategies, legal foundations, and lifestyle boundaries that keep my business profitable without stealing my peace. Whether you're building your first six figures or scaling past seven, this show will help you grow your revenue without sacrificing your presence, your sleep, or your sanity. Because success isn't just about how much you make—it's about having the freedom to actually enjoy your life. New to my world? I’m a lawyer-turned-entrepreneur who built an 7-figure digital product business helping thousands of founders legally protect and grow their online businesses. These days, I’m here to share not just the legal clarity but the lessons, stories, and strategies that make business and life more fulfilling. I'm the author of the best-selling book, When I Start My Business, I'll Be Happy, and a weekly newsletter called Sam's Sidebar. Originally a proud Philly girl, I now live ON Long Island with my husband, Ryan, and bernedoodle/velcrodog, Hudson.

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60 recent

August 24, 20268 min

I Built a Multi-Million Dollar Business to Avoid Feeling Anything. [Summer Read-Aloud]

I got forced to slow down, and it's the lesson I need to learn over and over again. In this episode, I read a personal essay from my Substack about a tennis injury that took me out mid swing. One minute I'm making an incredible shot down the line, the next I'm on the ground with my knee twisted and my foot throbbing. But this episode isn't really about the injury. It's about what happens when your body forces you to stop, and what that stillness makes you face, including grief I've been carrying since losing both of my parents. In this episode, you'll hear… The moment I went down mid-shot at a tennis clinic, and the very reaction that followed (spoiler: it involved refusing to stop playing) Why I instinctively downplayed the injury and tried to keep going, even with blood involved The connection I draw between forcing my body to heal on it's own timeline Click here to find the full show notes and transcript for this episode. EPISODE RESOURCES: Subscribe to Sam's Substack Read today's essay I got forced to slow down Get Sam's weekly newsletter, Sam's Sidebar If you have a question you’d like Sam to answer on a future podcast episode, you can submit it here . Click here to be notified when new episodes of On Your Terms® come out CONNECT: Get Sam's weekly newsletter, Sam's Sidebar Follow Sam on Instagram Follow Sam on YouTube Subscribe to Sam's Substack Take Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business" DISCLAIMER

August 17, 20269 min

How I Stopped Doomscrolling and Started Watching This. [Summer Read-Aloud]

Have you ever had a moment so small (a bird, of all things) crack open something so much bigger about how you're living your life? This week's episode is part of my summer series where I'm reading personal essays straight from my Substack. This one's about a very ornery bird I met on a hike in Patagonia, the bird I accidentally trapped in my bedroom when I was 10 (yes, really), and how a string of small, strange bird encounters slowly nudged me toward paying more attention to the world right in front of me. If you've been feeling stuck in your phone, disconnected from your neighborhood, or like you're moving through life without really noticing it, this one's for you. It's not really about birds. It's about presence. In this episode, you'll hear… The story of the bird who followed me on a brutal hike through the Andean Mountains and seemed to be personally attacking my confidence What happened when I accidentally let a bird into my childhood bedroom (and what I found six months later) Why standing somewhere as vast as Patagonia has a way of putting your entire life in perspective How coming home to Long Island turned into an unexpected obsession with birdwatching What robins, swans, and bald eagles taught me about noticing the seasons changing, even when I couldn't feel it yet Why paying attention to the small, local, unglamorous things is what's actually helped me feel rooted and connected, more than anything online ever has Click here to find the full show notes and transcript for this episode. EPISODE RESOURCES: Subscribe to Sam's Substack Read today's essay How being attacked by a bird in Patagonia forced me offline Get Sam's weekly newsletter, Sam's Sidebar If you have a question you’d like Sam to answer on a future podcast episode, you can submit it here . Click here to be notified when new episodes of On Your Terms® come out CONNECT: Get Sam's weekly newsletter, Sam's Sidebar Follow Sam on Instagram Follow Sam on YouTube Subscribe to Sam's Substack Take Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business" DISCLAIMER

August 10, 202610 min

How My Productivity Killed My Creativity [Summer Read-Aloud]

We've lost the plot when it comes to creating content. In this week's summer read-aloud, I share a personal essay on how my own productivity systems, batching, optimizing, and keeping up with an AI fueled content arms race, ended up killing my creativity. So kick back, pop in your headphones, maybe go for a walk, and let's talk about why being productive and being creative aren't always the same thing. In this episode, you'll hear… Why I'm running low on content ideas for the first time in a decade, and what that taught me How my 2026 "gap year" backfired into more batching and pressure instead of the spaciousness I wanted The real cost of optimizing everything, and why productivity can quietly kill creativity Why AI is making the content arms race worse, not better What actually refills my creative well, and why living your life is the best content strategy there is Click here to find the full show notes and transcript for this episode. EPISODE RESOURCES: Subscribe to Sam's Substack Read today's essay How my productivity killed my creativity Get Sam's weekly newsletter, Sam's Sidebar If you have a question you’d like Sam to answer on a future podcast episode, you can submit it here . Click here to be notified when new episodes of On Your Terms® come out CONNECT: Get Sam's weekly newsletter, Sam's Sidebar Follow Sam on Instagram Follow Sam on YouTube Subscribe to Sam's Substack Take Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business" DISCLAIMER

August 3, 20269 min

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

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 year. I did not stay off. Instead of a regular episode this week, I'm reading you this essay straight from my Substack, the place where I write about grief, overconsumption, overworking, and learning to actually be present in my life. My full slate of regular On Your Terms® episodes will be back on September 14th, but until then, here's the honest, slightly humbling truth about why I can't stop working, and what it's taught me about rest, distraction, and grief. In this episode, you'll hear… Why I declared 2026 my entrepreneurial gap year, and how it turned into a full time job anyway The real reason I keep reaching for my phone, even when I'm trying to unplug What my brutally honest friend said that made me realize my "time off" looked exactly like work How grief shows up in the smallest, most random moments, and why distraction feels easier than sitting with it Why I'm learning to be kinder to myself about the blurry line between resting and being restless Click here to find the full show notes and transcript for this episode. EPISODE RESOURCES: Subscribe to Sam's Substack Read today's essay Why I can't stop working (even during my gap year) Sam's Substack Essay on saying sorry: I'm sorry, but I had to write this If you have a question you’d like Sam to answer on a future podcast episode, you can submit it here . Click here to be notified when new episodes of On Your Terms® come out CONNECT: Get Sam's weekly newsletter, Sam's Sidebar Follow Sam on Instagram Follow Sam on YouTube Subscribe to Sam's Substack Take Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business" DISCLAIMER

July 27, 202610 min

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

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 chosen by me anymore. It's chosen by whoever posted about it first. This summer, I'm taking a little break from our regular episodes so I can rest, recharge, and come back to you on September 14th with a full slate of new content. In the meantime, I'm sharing a few of my favorite essays from my Substack, Sam Vander Wielen, right here on the podcast. Today's essay is all about a day I spent in New York City trying to unlearn the habit of letting algorithms and influencers decide what I like, and how I'm working to reclaim my own taste instead. In this episode, you'll hear… The pancake line that made me question everything about how I make decisions Why I think over 80% of Instagram-hyped restaurants aren't even worth the hype What my no-buy Amazon year has taught me about slowing down and shopping with intention The conversations with local shop owners that ended up meaning more than any five-star review How I'm working to reclaim my own preferences, both in New York City and in my everyday life Click here to find the full show notes and transcript for this episode. EPISODE RESOURCES: Get Sam's weekly newsletter, Sam's Sidebar Subscribe to Sam's Substack Read today's essay Field notes from NYC: reclaiming my own taste If you have a question you’d like Sam to answer on a future podcast episode, you can submit it here . Click here to be notified when new episodes of On Your Terms® come out CONNECT: Get Sam's weekly newsletter, Sam's Sidebar Follow Sam on Instagram Follow Sam on YouTube Subscribe to Sam's Substack Take Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business" DISCLAIMER

July 20, 202611 min

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

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 losing both of my parents in the same year, recovering from brain surgery, and realizing that being "extremely online" wasn't actually serving me or my business. This week I'm continuing my summer series, where I'm reading you essays straight from my Substack while I take a little break before we're back with full-force episodes on September 14th. This one's about the health, digital wellness, and business habits that helped me rebuild after burnout and loss, some I learned the hard way, some I'd skip again, but all of them helped me feel better inside and out. In this episode, you'll hear… Why grief changed what actually felt worth my time and energy, in business and in life The health habits (starting with what I eat first thing in the morning) that have made the biggest difference in how I feel My digital wellness rules, including why I brick my phone every single night The business habits that protect my creative energy and keep me from chasing everyone else's version of success Why I still believe in "them" focused content, but why "you" content matters too Click here to find the full show notes and transcript for this episode. EPISODE RESOURCES: Get Sam's weekly newsletter, Sam's Sidebar Subscribe to Sam's Substack Read today's essay Healthy Habits that rebuilt me after burnout & loss The Brick, the phone-blocking device Sam uses to disable apps (affiliate link) Cometeer, the half-caff coffee Sam switched to (affiliate link) Grab Sam's Book When I Start My Business, I'll Be Happy If you have a question you’d like Sam to answer on a future podcast episode, you can submit it here . Click here to be notified when new episodes of On Your Terms® come out CONNECT: Get Sam's weekly newsletter, Sam's Sidebar Follow Sam on Instagram Follow Sam on YouTube Subscribe to Sam's Substack Take Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business" DISCLAIMER

July 13, 202611 min

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

Everyone's obsessed with the getting off social media part — deleting the apps, doing the digital detox, bragging about their screen time going down. But almost no one talks about what's supposed to happen once you actually log off. Because here's the thing: stepping away from Instagram only to fall into a Substack doom scroll isn't really progress. It's just a softer-feeling version of the same problem. In this episode, I'm doing something a little different to celebrate summer — I'm reading you one of my recent essays straight from my free Substack, where I get real about what it's actually like to run a seven-figure business while also trying to build a life off the very apps I used to build it. This particular essay gets into something I don't talk about all that often: how losing both of my parents within a year of each other completely cracked open the way I think about time, attention, and what I actually want my life to look like — phone down or not. In this episode, you'll hear… Why getting offline isn't just about swapping one app for a "better" one The unsettling stat about our generation and other people's memories that I can't stop thinking about How losing both of my parents within a year of each other changed my relationship with my phone, and with my life What it actually looked like for me to start rebuilding an offline life on purpose, not by accident Why the more offline I get, the better my online business actually does Click here to find the full show notes and transcript for this episode. EPISODE RESOURCES: Get Sam's weekly newsletter, Sam's Sidebar Subscribe to Sam's Substack Read today's essay How I Got (More) Offline Grab Sam's Book When I Start My Business, I'll Be Happy If you have a question you’d like Sam to answer on a future podcast episode, you can submit it here . Click here to be notified when new episodes of On Your Terms® come out CONNECT: Get Sam's weekly newsletter, Sam's Sidebar Follow Sam on Instagram Follow Sam on YouTube Subscribe to Sam's Substack Take Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business" DISCLAIMER

July 6, 202635 min

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

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 put it, he can't wait to watch me be the most productive person he knows this summer. Fair. So in this episode, I'm pulling back the curtain on what a summer break actually looks like for a business owner. What I'm doing, what I'm not doing, and the honest truth about whether you're ever really "off" when your name, face, and voice are all over your business. For the podcast specifically, you'll be hearing weekly Substack essays read aloud by me for the next several weeks while the team gets a break from the production grind, and I get to focus on what I actually love right now: writing. I'll be back in full force with regular episodes on September 14th. In this episode, you'll hear… Why I'm taking a break from podcast recording (but not from my newsletter or Substack), and the difference between work that drains me and work that fills me up What "bare maintenance mode" looks like behind the scenes of a multi-seven-figure business, and the systems that make it possible I'm manifesting The mindset work behind taking time off, including the guilt, the fear of being "lapped," and what my therapist had to say about it My practical advice for designing your own break, even if it's just two weeks or a pause on one platform Click here to find the full show notes and transcript for this episode. EPISODE RESOURCES: Get Sam's weekly newsletter, Sam's Sidebar Subscribe to Sam's Substack Check out Jennifer Diaz, Sam's mindset coach If you have a question you’d like Sam to answer on a future podcast episode, you can submit it here . Click here to be notified when new episodes of On Your Terms® come out CONNECT: Get Sam's weekly newsletter, Sam's Sidebar Follow Sam on Instagram Follow Sam on YouTube Subscribe to Sam's Substack Take Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business" DISCLAIMER

June 29, 202657 min

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

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 bags for Boise, Idaho to attend Kit's Craft + Commerce Conference, and this year I recorded real-time clips along the way so it would feel like we were just hanging out in the hallway together. This is officially my fifth Craft + Commerce, and in this episode I'm sharing my full recap: why I keep going back, what my week actually looked like behind the scenes, the tactical tips I'm already using in my own business, and the bigger mindset shifts I'm walking away with this year, including a few things I picked up from a private mastermind with James Clear. You'll also hear some of my favorite on-the-street interviews including a quick chat with Kit founder Nathan Barry. In this episode, you'll hear… Why I keep going back to Craft + Commerce every year, and why Boise (yes, Boise) might be part of the magic On-the-street interviews with Mallory Rowan, Nathan Barry, Steve Kamb, and Barrett Brooks Three tactical takeaways from the conference, including Kit's new Signals feature and a workaround for connecting Substack and Kit The mindset shifts I'm walking away with around quality versus quantity, wanting something versus working for it, and finally feeling like I belong James Clear's "category killer" concept, and the difference between his concentrated strike and tailwind marketing strategies Click here to find the full show notes and transcript for this episode. EPISODE RESOURCES: Get your first month of Kit free (affiliate link) Steve Kamb's book, How to Try Again Follow Barrett Brooks on Instagram or visit barrettbrooks.com Follow Mallory Rowan on Instagram or visit malloryrowan.com Get Sam's weekly newsletter, Sam's Sidebar If you have a question you’d like Sam to answer on a future podcast episode, you can submit it here . Click here to be notified when new episodes of On Your Terms® come out CONNECT: Get Sam's weekly newsletter, Sam's Sidebar Follow Sam on Instagram Follow Sam on YouTube Subscribe to Sam's Substack Take Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business" DISCLAIMER

June 22, 202626 min

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

“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 about this a lot lately, and I think that little phrase is one of the most dangerous things you can say to yourself as a business owner. Because here’s what it’s actually doing: it’s letting you off the hook. It’s a quiet way of deciding something doesn’t apply to you before you’ve even given yourself the chance to find out if it could. And I’ve been getting a lot of these comments lately, in my DMs, in the comments, in the tone behind the questions I get, and I finally needed to say something about it. Not to call anyone out. I’ve thought it too. But because I think the story underneath “must be nice” is costing you more than you realize, and I don’t think it’s actually true. In this episode, I’m getting honest about what people don’t see: why the nos and the boundaries came before the revenue, what really shifted the way I run my business (hint: it wasn’t hitting a certain income number), and what it looks like to start building a business on your own terms right now, wherever you are. In this episode, you'll hear… Why “must be nice” is actually one of the most dangerous things you can say to yourself as a business owner The truth about what actually came first in my business: the permission, the nos, and the boundaries, before the money and the team How grief completely changed my relationship to what felt urgent in my business and what that meant for everything that came after Why saying yes to everything is not the path to making more money (and what to do instead) What the “arrival fallacy” has to do with building a business and why hitting a revenue milestone won’t be the thing that finally lets you say no How to take inspiration from someone ahead of you without dismissing their strategies because your situations look different Click here to find the full show notes and transcript for this episode. EPISODE RESOURCES: Grab Sam's Book When I Start My Business, I'll Be Happy Grab The Ultimate Bundle® on sale through Friday, June 26th. Get Sam's weekly newsletter, Sam's Sidebar If you have a question you’d like Sam to answer on a future podcast episode, you can submit it here . Click here to be notified when new episodes of On Your Terms® come out CONNECT: Get Sam's weekly newsletter, Sam's Sidebar Follow Sam on Instagram Follow Sam on YouTube Subscribe to Sam's Substack , Beyond Business Take Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business" DISCLAIMER