On Your Terms®

Hosted by Sam Vander Wielen

Business Entrepreneurship

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321

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Nov 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

November 9, 202647 min

302. I Did Less This Year and Had My Highest-Revenue Year Ever

What if the thing holding your business back is you doing too much? Going into this year, I planned an “entrepreneur gap year” with no big launches, no book, and less pressure. Instead, I took 30+ flights, crashed and burned by summer, hurt my foot playing tennis, and stepped away from content almost entirely. And my business didn’t slow down. Leads kept coming in, sales kept happening, and I’m now having my highest-revenue year ever. In this cozy, behind-the-scenes episode, I’m sharing what I cut, why I think it worked, and the honest part I’m still sitting with. 👩🏻‍💻 Join me for my free workshop with Kit, What’s in Sam Vander Wielen’s Kit? , on Tuesday, November 10 at 3 PM ET. Can’t make it live? Sign up anyway and we’ll send you the replay, plus an exclusive Kit deal just for registrants. Save your spot here → https://partners.kit.com/samvw-workshop In this episode, you’ll hear: What happened when I went offline for the summer, and what it revealed about my business Why “doing less” is not the same thing as working less How deleting Instagram and email off my phone made me more productive The “I could, but I won’t” mindset I’m practicing so I stop saying yes to everything The four pieces of my boring foundation that let my business grow without needing more of me What it feels like to get everything you wanted and still ask, “Okay, now what?” Click here to find the full show notes and transcript for this episode. EPISODE RESOURCES: Save your spot for my free workshop with Kit , What's in Sam Vander Wielen's Kit? (Tuesday, November 10 at 3 PM ET; replay sent to everyone who registers) Sign up for my free weekly email, Sam's Sidebar Grab my book, When I Start My Business, I'll Be Happy: A Practical No-BS Guide to Successful Online Entrepreneurship Watch my free legal workshop, 5 Steps to Legally Protect and Grow Your Online Business (the best way to get the Ultimate Bundle®) Theodore the Bunny on Instagram 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

November 2, 202638 min

301. How I Grew My Email List to 74,000 (Without Living on Instagram)

You could post the best Instagram post of your life and hardly anybody would see it. Meanwhile, I have more than 74,000 people on my email list, which is way more than whoever follows me on social media. And that’s not an accident. When my parents died within the same year, I didn’t have the capacity to be on social media. So I went all in on my email list, and it became the life raft that kept my business afloat. In this episode, recorded from Kit Studios in NYC, I’m sharing exactly what’s growing my list right now in 2026: Meta ads, ManyChat DMs (including the freebie that brought in 205 signups in a single month), referrals, and Kit’s creator referral program. I’ll also share the four things I’d do if I started over tomorrow, and what’s NOT working with my emails (plus the fun, very lawyer-y revamp I’m making to Sam’s Sidebar). 👩🏻‍💻 Join me for my free workshop with Kit, What’s in Sam Vander Wielen’s Kit? , on Tuesday, November 10 at 3 PM ET. Can’t make it live? Sign up anyway and we’ll send you the replay, plus an exclusive Kit deal just for registrants. Save your spot here → https://partners.kit.com/samvw-workshop In this episode, you’ll hear: How my email list became the life raft that kept my business afloat through the hardest season of my life Why people who read emails are the ones who actually buy (and why your Instagram followers probably aren't) The four list-building strategies bringing in subscribers right now, including how one freebie brought in 205 signups in a single month through Instagram DMs alone The four things I'd do on day one if I started building my email list over tomorrow What's NOT working with my emails right now, and the fun (and very lawyer-y) revamp I'm making to Sam's Sidebar Click here to find the full show notes and transcript for this episode. EPISODE RESOURCES: Save your spot for my free workshop with Kit , What's in Sam Vander Wielen's Kit? (Tuesday, November 10 at 3 PM ET; replay sent to everyone who registers) Sign up for my free weekly email, 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

October 26, 202634 min

300. I Asked 1,077 Customers Why They Bought. It Changed How I Sell.

You have an offer you want to sell. Maybe you’ve even sold a bit of it already. But do you really understand why people buy it? Or are you playing by feel? Most business owners market their offers using the language they use in everyday life, or whatever sounded good to a few friends and family members. The problem is that your customers don’t talk like you. And if you don’t know what’s actually making them click purchase, you’re wasting a lot of time on marketing that doesn’t work. For the 300th episode of On Your Terms®, I shared what 1,077 of my recent buyers told me about why they bought the Ultimate Bundle®, and the three big changes I’ve made in my business because of it. Here’s what I’ve learned. In this episode, you’ll hear: Why surveying customers right after purchase beats surveying them after they’ve used your product The difference between “where did you find me” and “why did you buy” (and why most businesses only ask the first one) How my buyers actually find me: 40% through Meta ads, 25% through Instagram organically, and 22% through referrals Why my podcast works more as a conversion tool than a discovery tool The “enough moment” question that reveals what finally pushes someone to buy Why asking about competitors helps you find your unique differentiators (not to compare prices) Click here to find the full show notes and transcript for this episode. EPISODE RESOURCES: The Ultimate Bundle® (includes a copy of my post-purchase survey questions as a free bonus) Ep 280: How I Got My First 1,000 Subscribers on Substack My recap episode from James Clear’s mastermind Sam’s book, When I Start My Business, I’ll Be Happy: A Practical No-BS Guide to Successful Online Entrepreneurship 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

October 19, 20261 hr 18 min

The 5 Legal Steps I Took Before Making $10M Online

Maybe you’re about to start your online business and want to do it right from day one. Or maybe you’ve been at it for a while and, if you’re honest, your business is held together with duct tape, string, hope, and a prayer. Either way, you want the same thing: your legal ducks in a row, so you can stop wondering if you missed something and finally put yourself out there with confidence. The problem is you don’t know what you don’t know. So in today’s episode, I’m giving you my entire free legal training. I recently taught a live class for thousands of business owners called How to Legally Protect and Grow Your Online Business Before 2026 Ends , and I’m sharing every minute of it with you. I walk you through the five legal steps to take and the order to take them in, plus the legal updates you need to know right now about AI, the ADA website lawsuit trend, and protecting your personal privacy. This one is meant to be acted on, so grab a notebook. GRAB THE ULTIMATE BUNDLE® ON SALE! SAVE $850 + GET BIG BONUSES → https://www.samvanderwielen.com/ub-bonus/ In this episode, you’ll hear… The 5 legal must-haves to put in place before you make another dollar online A step-by-step look at officially forming your business LLC or sole proprietorship: how to decide which one fits you Why business insurance is one of the best investments you’ll ever make A practical way to figure out what you can (and can’t) offer online, especially when you’re working outside your professional license Why an AI-generated or copy-and-pasted contract may not be enforceable The predatory ADA website lawsuits hitting small business owners, who owns the work you create with AI, new AI labeling rules, and simple ways to protect your personal privacy online RESOURCES: THE ULTIMATE BUNDLE® IS ON SALE! SAVE $850 + GET BIG BONUSES → https://www.samvanderwielen.com/ub-bonus/ CONNECT: Sam on Instagram Sam on Facebook On Your Terms ® on Instagram DISCLAIMER

October 14, 20261 min

How to Legally Protect & Grow Your Online Business Before 2026 Ends [Join me live!]

Is the legal side of your business handled? Or is it still sitting on your "I'll deal with it later" list? Maybe you're about to start your online business and you want to do it right from day one. Or maybe you've been at it a while and you have a feeling you skipped a few legal steps. Either way, you want your ducks in a row before you take even one more dollar online. I get it. The legal stuff is overwhelming, and most people don't know where to start or what order to do things in. So I'm teaching it, step by step, in a free live class. The live class has passed but you can take my free legal workshop "5 Steps to Legally Protect & Grow Your Online Business" any time. Grab your spot here 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

October 12, 202636 min

299. Ready to Quit Your Job? Here's How I Knew It Was Time.

Daydreaming about life outside your nine-to-five? Wondering if your side hustle could become your full-time thing, but not sure when to actually leave? In this episode, I'm sharing how I knew it was time to leave my corporate law career, the financial and logistical steps I'd have in place before you give notice, and the emotional prep nobody talks about. Because being miserable at your job isn't a sign you're ready to leave. It's a sign to start getting ready. Plus, the turbulent plane ride that finally made me say "I'm done," and the weekend I almost begged for my job back. In this episode, you'll hear… Why "just take the leap" can be financially irresponsible advice How much savings I recommend having before you leave How I started paying myself (hint: $500 a month) What to know about health insurance when you go self-employed The backend setup to do while you're still getting a paycheck How to tell if you need a business or just a different job Why fear after the leap doesn't mean you chose wrong Click here to find the full show notes and transcript for this episode. EPISODE RESOURCES: Sam's book, When I Start My Business, I'll Be Happy: A Practical No-BS Guide to Successful Online Entrepreneurship Check out KIT & get your first month free (affiliate link) 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

October 7, 20267 min

I've Sold $10M Online. Here's What Worries Me Now.

I've sold over $10M in digital products online, and right now three things in our industry have my attention: protecting yourself from AI and the AI label changes coming, protecting your personal privacy as a creator, and the wave of ADA lawsuits hitting online business owners. The live class has passed but you can take my free legal workshop "5 Steps to Legally Protect & Grow Your Online Business" any time. Grab your spot here In this episode, you'll hear… What's changing with AI labeling, and what it means for how you create and post Why your personal privacy matters more than ever when you're the face of your business Why ADA lawsuits are on the rise, and how to get ahead of them Where we'll dig in together: my free live workshop on Monday, October 19 EPISODE RESOURCES: The live class has passed but you can take my free legal workshop "5 Steps to Legally Protect & Grow Your Online Business" any time. Grab your spot here 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

October 5, 20261 hr 1 min

298. I Spent a Week with James Clear, Mark Manson, and Gretchen Rubin. Here's What I'm Changing in My Business.

What happens when you get invited to an author mastermind with James Clear, Mark Manson, and Gretchen Rubin? You say yes, then spend days wondering if they sent the email to the wrong person. I'm taking you inside James Clear and Nathan Barry's mastermind at Kit Studios in NYC. I'm sharing the best tactical tips I picked up from people who've sold tens of millions of books: the two-slide Instagram Stories trick that skyrockets engagement, what makes a quiz lead magnet actually convert, a genius way to turn nice DMs into public reviews, and the one thing about Instagram almost everybody agreed on. Plus, I get honest about what it feels like to be the smallest one in the room, and why you won't feel like you belong before you're invited in. I also grab Dan Go and Steve Kamb in the hallway to share their biggest takeaways. 👩🏻‍💻 REGISTER FOR MY FREE LIVE LEGAL CLASS --> https://www.samvanderwielen.com/live-legal-workshop (Replay included!) In this episode, you'll hear… How a decade of tiny, unglamorous decisions landed me at a mastermind with James Clear, Mark Manson, and Gretchen Rubin What makes a quiz lead magnet actually work, and why treating your results page like a "hostage situation" is costing you subscribers A genius (and totally free) way to turn nice DMs and emails into public reviews and testimonials What it's really like to be the smallest one in the room, and why you won't feel like you belong before you're invited in Hallway chats with health coach Dan Go and Nerd Fitness founder Steve Kamb about fighting for your own art and doing things your way Click here to find the full show notes and transcript for this episode. EPISODE RESOURCES: Save your seat for the FREE last live legal workshop of 2026, How to Start an Online Business Legally Before 2026 Ends , on Monday, October 19th (Replay included!) Sam's book, When I Start My Business, I'll Be Happy: A Practical No-BS Guide to Successful Online Entrepreneurship Check out KIT & get your first month free (affiliate link) Craft and Commerce recap episode Sam's previous mastermind recap episode from earlier this year Dan Go: https://dango.co & Instagram Steve Kamb: https://stevekamb.com & Instagram 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

September 28, 202631 min

297. If I Started My Business Today, I'd Ignore My Own Advice (Here's What $9M Taught Me)

If you started your business today, would you actually follow your own old advice? I wouldn't. And after over $9 million in sales, I'm telling you exactly why. This isn't the first time I've tackled this topic either. Back in episode 28 (2022) and episode 186 (2024), I talked about what I'd do differently if I started over. Some of that advice still holds up. A lot of it doesn't anymore. So today I'm setting the record straight on what I'd keep, what I'd completely reverse, and what I think matters most for online business owners heading into 2026 and beyond. In this episode, you'll hear… Why I still believe there's no secret formula for building your business (and why copying what's "working" for everyone else can actually box you in) The one social media strategy I'd keep exactly the same, plus how I use AI tools to repurpose one cornerstone piece of content instead of creating from scratch everywhere Why I'd ditch a "social media first" approach entirely and build an audience-first business instead What I wish I'd done sooner when it comes to getting comfortable charging for my content and expertise How I shifted from "post everywhere, all the time" to focusing on fewer, bigger tasks that actually move my business forward Why "pace" today means being reactive and in the conversation, not just pumping out volume 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 Episode 280. How I Got My First 1,000 Subscribers on Substack 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 31, 202612 min

I Planned a Year of Doing Nothing. I Took 19 Flights Instead. [Summer Read-Aloud]

My gap year was supposed to be boring. Instead I've taken 19 flights before summer even ended, and somehow I still feel more rested than I have in years. This episode is part of my summer read-aloud series, where I'm sharing personal essays straight from my Substack. This one's about what happened when the "spacious, do-nothing" gap year I planned turned into a calendar full of tennis lessons, swim classes, and last-minute flights, and why I had to stop judging myself for it. In this episode, you'll hear… Why I planned a year of "blank space" and ended up busier than ever, just in a totally different way The real difference between being chronically online and busy versus chronically offline and busy (and why one feels so much better than the other) What happens to my brain, my relationships, and my sense of reality when I spend too much time online The moment I realized what I was actually feeling wasn't guilt about overcommitting. It was judgment Click here to find the full show notes and transcript for this episode. EPISODE RESOURCES: Subscribe to Sam's Substack Read today's essay My gap year was supposed to be boring Get Sam's book When I Start My Business, I'll Be Happy 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