Free Daily Podcast Summary
On Your Terms: Daily Summaries Delivered
by Sam Vander Wielen
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. 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.
Latest Episodes
The most recent episodes — sign up to get AI-powered summaries of each one.
- 6 days ago34 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 productThe 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 referralsWhy my podcast works more as a conversion tool than a discovery toolThe “enough moment” question that reveals what finally pushes someone to buyWhy 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 SubstackMy recap episode from James Clear’s mastermindSam’s book, When I Start My Business, I’ll Be Happy: A Practical No-BS Guide to Successful Online EntrepreneurshipIf 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 outCONNECT:Get Sam's weekly newsletter, Sam's SidebarFollow Sam on InstagramFollow Sam on YouTubeSubscribe to Sam's SubstackTake Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"DISCLAIMER
- 1 weeks ago1h 18m
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 onlineA step-by-step look at officially forming your businessLLC or sole proprietorship: how to decide which one fits youWhy business insurance is one of the best investments you’ll ever makeA practical way to figure out what you can (and can’t) offer online, especially when you’re working outside your professional licenseWhy an AI-generated or copy-and-pasted contract may not be enforceableThe 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 onlineRESOURCES:THE ULTIMATE BUNDLE® IS ON SALE! SAVE 850 + GET BIG BONUSES → https://www.samvanderwielen.com/ub-bonus/ CONNECT:Sam on InstagramSam on FacebookOn Your Terms® on InstagramDISCLAIMER
- 2 weeks ago1 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.→ Register free for my last live legal workshop of 2026 called "How to Start an Online Business Legally Before 2026 Ends" on Monday, October 19: https://www.samvanderwielen.com/live-legal-workshopCan't make it live? Sign up ^ and I'll send you the replay.EPISODE RESOURCES:Save your free seat at my live legal workshop on 10/19: https://www.samvanderwielen.com/live-legal-workshop (Replay included!)In my live legal workshop, I'll share the easy ways to navigate these legal changes, and teach you how to start an online business legally before 2026 ends. See you there!CONNECT:Get Sam's weekly newsletter, Sam's SidebarFollow Sam on InstagramFollow Sam on YouTubeSubscribe to Sam's SubstackTake Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"DISCLAIMER
- 2 weeks ago36 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.👩🏻💻 REGISTER FOR MY FREE LIVE LEGAL CLASS --> https://www.samvanderwielen.com/live-legal-workshop (Replay included!)In this episode, you'll hear…Why "just take the leap" can be financially irresponsible adviceHow much savings I recommend having before you leaveHow I started paying myself (hint: $500 a month)What to know about health insurance when you go self-employedThe backend setup to do while you're still getting a paycheckHow to tell if you need a business or just a different jobWhy fear after the leap doesn't mean you chose wrongClick 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 EntrepreneurshipCheck 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 outCONNECT:Get Sam's weekly newsletter, Sam's SidebarFollow Sam on InstagramFollow Sam on YouTubeSubscribe to Sam's SubstackTake Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"DISCLAIMER
- 3 weeks ago7 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.→ Register free for my last live legal workshop of 2026 called "How to Start an Online Business Legally Before 2026 Ends" on Monday, October 19: https://www.samvanderwielen.com/live-legal-workshopCan't make it live? Sign up ^ and I'll send you the replay.In this episode, you'll hear…What's changing with AI labeling, and what it means for how you create and postWhy your personal privacy matters more than ever when you're the face of your businessWhy ADA lawsuits are on the rise, and how to get ahead of themWhere we'll dig in together: my free live workshop on Monday, October 19EPISODE RESOURCES:Save your free seat at my live legal workshop on 10/19: https://www.samvanderwielen.com/live-legal-workshop (Replay included!)In my live legal workshop, I'll share the easy ways to navigate these legal changes, and teach you how to start an online business legally before 2026 ends. See you there!CONNECT:Get Sam's weekly newsletter, Sam's SidebarFollow Sam on InstagramFollow Sam on YouTubeSubscribe to Sam's SubstackTake Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"DISCLAIMER
- 3 weeks ago1h 1m
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 RubinWhat makes a quiz lead magnet actually work, and why treating your results page like a "hostage situation" is costing you subscribersA genius (and totally free) way to turn nice DMs and emails into public reviews and testimonialsWhat 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 inHallway chats with health coach Dan Go and Nerd Fitness founder Steve Kamb about fighting for your own art and doing things your wayClick 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 EntrepreneurshipCheck out KIT & get your first month free (affiliate link)Craft and Commerce recap episodeSam's previous mastermind recap episode from earlier this yearDan Go: https://dango.co & InstagramSteve Kamb: https://stevekamb.com & InstagramIf 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 outCONNECT:Get Sam's weekly newsletter, Sam's SidebarFollow Sam on InstagramFollow Sam on YouTubeSubscribe to Sam's SubstackTake Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"DISCLAIMER
- Sep 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 everywhereWhy I'd ditch a "social media first" approach entirely and build an audience-first business insteadWhat I wish I'd done sooner when it comes to getting comfortable charging for my content and expertiseHow I shifted from "post everywhere, all the time" to focusing on fewer, bigger tasks that actually move my business forwardWhy "pace" today means being reactive and in the conversation, not just pumping out volumeClick here to find the full show notes and transcript for this episode.EPISODE RESOURCES:Get Sam's weekly newsletter, Sam's SidebarSubscribe to Sam's SubstackEpisode 280. How I Got My First 1,000 Subscribers on SubstackIf 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 outCONNECT:Get Sam's weekly newsletter, Sam's SidebarFollow Sam on InstagramFollow Sam on YouTubeSubscribe to Sam's SubstackTake Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"DISCLAIMER
- Aug 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 wayThe 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 onlineThe moment I realized what I was actually feeling wasn't guilt about overcommitting. It was judgmentClick here to find the full show notes and transcript for this episode.EPISODE RESOURCES:Subscribe to Sam's SubstackRead today's essay My gap year was supposed to be boringGet Sam's book When I Start My Business, I'll Be HappyGet Sam's weekly newsletter, Sam's SidebarIf 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 outCONNECT:Get Sam's weekly newsletter, Sam's SidebarFollow Sam on InstagramFollow Sam on YouTubeSubscribe to Sam's SubstackTake Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"DISCLAIMER
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About On Your Terms
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. 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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