On Your Terms®

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

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

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

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-workshop

Can'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 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

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 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:

• 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)
• 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

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-workshop

Can'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 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:

• 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 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

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

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:

• 👩🏻‍💻 REGISTER FOR MY FREE LIVE LEGAL CLASS --> https://www.samvanderwielen.com/live-legal-workshop
• 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

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
• 👩🏻‍💻 REGISTER FOR MY FREE LIVE LEGAL CLASS --> https://www.samvanderwielen.com/live-legal-workshop
• 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

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
• 👩🏻‍💻 REGISTER FOR MY FREE LIVE LEGAL CLASS --> https://www.samvanderwielen.com/live-legal-workshop
• Read today's essayI 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

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
• 👩🏻‍💻 REGISTER FOR MY FREE LIVE LEGAL CLASS --> https://www.samvanderwielen.com/live-legal-workshop
• 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

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
• 👩🏻‍💻 REGISTER FOR MY FREE LIVE LEGAL CLASS --> https://www.samvanderwielen.com/live-legal-workshop
• 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

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
• 👩🏻‍💻 REGISTER FOR MY FREE LIVE LEGAL CLASS --> https://www.samvanderwielen.com/live-legal-workshop
• 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

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
• 👩🏻‍💻 REGISTER FOR MY FREE LIVE LEGAL CLASS --> https://www.samvanderwielen.com/live-legal-workshop
• 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

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
• 👩🏻‍💻 REGISTER FOR MY FREE LIVE LEGAL CLASS --> https://www.samvanderwielen.com/live-legal-workshop
• 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

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
• 👩🏻‍💻 REGISTER FOR MY FREE LIVE LEGAL CLASS --> https://www.samvanderwielen.com/live-legal-workshop
• 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

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
• 👩🏻‍💻 REGISTER FOR MY FREE LIVE LEGAL CLASS --> https://www.samvanderwielen.com/live-legal-workshop
• 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

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)
• 👩🏻‍💻 REGISTER FOR MY FREE LIVE LEGAL CLASS --> https://www.samvanderwielen.com/live-legal-workshop
• Steve Kamb's book, How to Try Again
• Follow Barrett Brooks on Instagram or visit https://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

“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
• 👩🏻‍💻 REGISTER FOR MY FREE LIVE LEGAL CLASS --> https://www.samvanderwielen.com/live-legal-workshop
• Grab The Ultimate Bundle® on salethrough 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

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. There's no shortage of people online saying digital products are dead, courses are dead, the whole thing is over.

Here's the thing: the market has changed. A lot. And if you have a digital product or course, you've probably felt it. Buyers are taking longer to make decisions, coming in with their guard up, asking more questions. But "harder" is not the same as "dead." After 10 years in this industry and $9M in digital product sales, I want to give you my honest take on what's actually happening, what's changed, and exactly what it takes to build and sell a digital product that still works in 2026 and beyond.

In this episode, you'll hear…

• Why buyer skepticism is at an all-time high and what actually caused it
• How the 2020-2021 online business boom (and AI) flooded the market with low-quality products
• The real reason information-only products are struggling, and what to do instead
• Six things your digital product must do to succeed in today's economy
• Why cold-audience funnels are suffering the most right now
• What "long game trust" actually looks like, and why it's your biggest competitive advantage
• The honest truth about how much work building a successful digital product takes

Click here to find the full show notes and transcript for this episode.

EPISODE RESOURCES:

• 👩🏻‍💻 REGISTER FOR MY FREE LIVE LEGAL CLASS --> https://www.samvanderwielen.com/live-legal-workshop
• Get Sam's weekly newsletter, Sam's Sidebar
• Get 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, Beyond Business
• Take Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"

DISCLAIMER