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298. I Spent a Week with James Clear, Mark Manson, and Gretchen Rubin. Here's What I'm Changing in My Business.05 Oct 202601:01:14

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.

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297. If I Started My Business Today, I'd Ignore My Own Advice (Here's What $9M Taught Me)28 Sep 202600:31:16

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.

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I Planned a Year of Doing Nothing. I Took 19 Flights Instead. [Summer Read-Aloud]31 Aug 202600:12:32

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.

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I Built a Multi-Million Dollar Business to Avoid Feeling Anything. [Summer Read-Aloud]24 Aug 202600:08:54

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.

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How I Stopped Doomscrolling and Started Watching This. [Summer Read-Aloud]17 Aug 202600:10:04

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.

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How My Productivity Killed My Creativity [Summer Read-Aloud]10 Aug 202600:10:28

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.

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I Declared a Gap Year. Then I Turned It Into a Full-Time Job. [Summer Read-Aloud]03 Aug 202600:09:34

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.

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How I Stopped Letting the Algorithm Decide What I Like [Summer Read-Aloud]27 Jul 202600:10:52

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.

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15 Habits that Rebuilt Me After I Lost Everything [Summer Read-Aloud]20 Jul 202600:11:49

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.

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More Memories of Other People's Lives Than Our Own [Summer Read-Aloud]13 Jul 202600:11:29

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.

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296. I Took a Whole Month Off and Didn't Tell a Soul — Here's What Happened.06 Jul 202600:35:41

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.

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295. I Went to Craft + Commerce. Here's Everything I Learned.29 Jun 202600:57:52

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.

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294. Why 'Must Be Nice' Is the Most Dangerous Thing You Can Say to Yourself22 Jun 202600:26:20

“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.

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293. I've Sold $9M in Digital Products. Here's My Honest Take on the Market Right Now15 Jun 202600:32:05

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.

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292. How to Actually Make Instagram Reels for Your Business (Without Losing Your Mind)08 Jun 202600:48:08

You know reels are one of the best ways to grow your business on Instagram. You've seen other people crushing it. You've probably even sat down to film one yourself, maybe more than once, and then... you just didn't post it. Or you did, and it flopped, and somewhere along the way, the whole thing started to feel way more complicated than it's worth.

Here's what I actually think is happening: you're drowning in advice that was designed for influencers, not for people who run a real business. Hook formulas, trending audio, CapCut tutorials, edit transitions... it is A LOT. And most of it doesn't apply to you.

So in today's episode, I'm breaking it all the way down to the actual basics: how to find ideas, how to script a reel, how to film it, and how to batch the whole thing so it doesn't take over your life. No dances. No pressure to go viral. Just what actually works to get you more clients from Instagram.

In this episode, you'll hear…

  • Why you shouldn't be getting content inspiration from competitors (and where to look instead)
  • How to write a hook that stops the scroll, even if you hate writing
  • The one structural shift that's making reels perform better right now (hint: stop giving it all away in the video)
  • Filming best practices that make a real difference, even with just your phone
  • How to batch your reel production so you're not starting from scratch every single week
  • The four reel formats explained, so you can pick what actually works for your personality and schedule

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

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291. 11 'Bad Habits' That Actually Built My 7-Figure Business01 Jun 202600:39:08

Every entrepreneurship influencer on the internet has an opinion about what you should be doing. Six AM wake-ups. A content calendar mapped out six months in advance. Tracking every metric. Showing up on every platform all at once. But here's the thing — what successful founders say they do and what they actually do behind the scenes? Often very, very different.

I know because I'm one of those founders. And when people meet me in real life, the thing they always say is, "Wait, your business is so chill and simple. You don't do any of the stuff people say you're supposed to do."

So today I'm pulling back the curtain and giving you the real list: my 11 "bad habits" that I genuinely believe built my seven-figure business. The stuff I do, don't do, and intentionally skip — and why I think it's actually the reason this whole thing has worked at all.

In this episode, you'll hear…

  • Why ghosting your Instagram Stories for days (or weeks) at a time might actually be good for your business
  • How skipping the perfectly planned content calendar has made Sam a better, more creative writer
  • The surprising reason oversharing the good, the bad, and the ugly has been one of her biggest trust-builders
  • Why saying yes to almost everything early on was one of the smartest moves she made
  • How staying resistant to every shiny new platform or trend has kept her business simple and wildly profitable

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290. I'm Sorry, But Someone Had to Say It (On Apologizing For Everything)25 May 202600:22:29

I recently apologized to my shower handle.

No, really. I turned off the water before rinsing out my conditioner, reached back to flip it on again, and instinctively said sorry to a cold, metal, completely inanimate faucet. And that moment stopped me dead in my tracks, because if I'm apologizing to shower handles, what else am I unnecessarily apologizing for in my life and business?

This episode is a little different. I'm reading you an essay I originally published on my Substack, Beyond Business, because I genuinely believe so many of you need to hear it, not just read it. It's something I was almost too scared to put out into the world. But here's what I know: the over-apologizing so many of us do, especially as women in business, is costing us. It's costing us deals, visibility, clients, confidence, and the kind of success we've worked incredibly hard for.

In this episode, you'll hear…

  • Why so many of us learned to over-apologize long before we ever started a business, and how that pattern is still running the show
  • The jaw-dropping (and infuriating) moment at a law firm that made me feel like my ambition was something to be ashamed of
  • Where over-apologizing shows up in your business, including in your marketing, your pricing conversations, and how you manage your team
  • A reflection prompt to help you identify where you might be apologizing unnecessarily, and what to do about it

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

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289. Why Doing Less Is Actually the Strategy18 May 202600:42:44

You're busy. You're building. You're making a thousand decisions a day — what to post, what to buy, what to eat, what to cut. And somewhere along the way, all of that choosing started to feel like its own full-time job.

Here's the thing: we've been sold this idea that more optimization equals more freedom. That if you just find the perfect system, the perfect routine, the perfect answer, you'll finally be able to relax. So you keep researching and refining and second-guessing. And the relaxing never actually comes.

This episode is about what happens when you stop. It's about de-optimizing your life — and why I think "good enough" isn't a consolation prize. It's the entire point. I'm sharing what's been quietly shifting for me (some of it unexpected, some of it born out of grief), and how I'm starting to let go of the pressure to have, do, and be the best version of everything, all the time. Spoiler: it feels a lot like relief.

In this episode, you'll hear…

  • How grief cracked open my relationship with time and completely reorganized my priorities
  • Why I stopped chasing "biggest business ever" and started making my business the least interesting thing about me
  • What happens when you spend less time on screens (hint: everything slows down, in the best way)
  • The three unexpected shifts I've noticed from de-optimizing: more confidence, more assuredness, and serious relief
  • The "consequences" framework that's helping me stop agonizing and start choosing Three ways this mindset shift is showing up in my business right now

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

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288. I Pulled Back From Social Media. It Performed Better.11 May 202600:41:50

What if stepping back from social media was actually the thing that made it work better for your business?

I'll be honest with you: my relationship with social media has been a lot. It helped me build a multi seven-figure business. Then it became my number one addiction. Then it turned into a coping mechanism I reached for every time life got hard. And then, after losing both of my parents, I basically wanted to throw my phone into the ocean and never look back.

In this episode, I'm sharing the full, messy truth of my relationship with social media, including the part that surprised even me: that since pulling way back, my content is performing better than it ever has. But here's what's different about this conversation: it's not just a "hire a team and disappear" story. It's a real mindset shift that I believe anyone can adopt, no matter what size your audience is or what stage your business is at

In this episode, you'll hear…

  • Why my relationship with social media went from exciting opportunity to full-blown addiction (and how grief changed everything)
  • The honest truth about why pulling back actually made my content perform better
  • The specific tools and strategies I use to protect my time and attention without disappearing from my business
  • How I restructured my content creation process so I spend less time on the app but show up with way more intention
  • Why posting less might actually be the smartest move you can make, even if you have a small audience

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

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287. Why Nobody Thinks of You When It's Time to Buy04 May 202600:48:44

Have you ever wondered why people in your audience don't think of you when they're ready to buy — even though you've been showing up, creating content, and putting offers out?

Here's the hard truth: it's probably not your audience size. It's not your content. It's not even your offer. The real problem is that nobody knows what to associate your name with. And the good news? That is a very fixable problem.

In this episode, I'm diving into why so many online business owners stay invisible — and what it actually takes to become the "McFlurry" of your industry. (Yes, we're going there. McDonald's, Wendy's Frosties, Burger King's unfortunate dessert menu, and what all of it has to do with YOUR business. I told you I always land the plane.)

In this episode, you'll hear…

  • Why shiny object syndrome is the #1 reason people can't figure out what you do
  • How adding too many offers actually dilutes your brand instead of growing your revenue
  • The "keeping up with the online Joneses" trap that pulls you away from what you actually want
  • Why the gurus telling you to pivot, rebrand, or go viral profit from your instability
  • The three things you actually need to do to become known for something in your industry

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286. I Went to an Invite-Only Mastermind. Here's Everything I Learned27 Apr 202600:48:34

I just got back from three days in Atlanta with some of the most impressive people in the online business space, and I am still processing all of it.

We're talking New York Times bestselling authors, YouTubers with millions of subscribers, book agents and editors, SaaS founders, and high-level consultants serving Fortune 100 companies. All 40 of us crammed into rooms, hot seats, and late-night fire pit hangs for what turned into one of the most valuable professional (and personal) experiences I've had in years.

I walked away with pages of notes on pricing psychology, LinkedIn strategy, storytelling, community building, and what it really takes to write and sell a book. But honestly? The biggest thing I took away wasn't a tactic at all. It was the realization that even after building a multi-seven-figure business, giving keynotes, and writing a book, I still don't fully believe in myself or what's possible for me.

And it turns out? Neither does pretty much everyone else in that room. So I figured I'd bring all of it back to you.

In this episode, you'll hear…

  • The pricing psychology tip from a master business consultant that will make you rethink every number on your sales page
  • Why the words "fee" and "costs" are quietly working against your sales (and what to say instead)
  • The LinkedIn profile mistakes almost everyone makes and the simple fixes that actually drive traffic to your business
  • What spending three days with NYT bestselling authors taught me about the realities of publishing, book deals, and where authors actually make their money
  • Why the most successful people in the room still felt like they didn't belong there, and what that means for you
  • The honest truth about AI that nobody in the online space seems willing to say out loud
  • Why going deep in one community beats trying to be everywhere at once

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

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DISCLAIMER

285. The Step Everyone Skips Before They Launch20 Apr 202600:38:44

You've watched other people's launches from the sidelines. The big revenue numbers, the sold-out offers, the "We Hit Our Goal in 24 Hours" Instagram stories. You want that too. And so you try. You do all the launch things. But something's off. The sales trickle in slower than you hoped, or it's just... crickets. And you start wondering if it's your emails, your offer, your timing, or honestly, if it's just you.

Here's the truth: it's probably none of those things.

The real issue is happening way before launch week ever starts. In this episode, I'm breaking down exactly what that is and what to build instead, so that your next launch has actual chompers waiting for it. (And yes, I'll explain what chompers means. Stick with me.)

In this episode, you'll hear…

  • Why copying someone else's launch strategy, webinar slides, or email subject lines will not get you the results you're looking for
  • What "chompers" are, why you need them, and how to build a community full of people who are ready to buy
  • How to identify where your ideal customer sits on the problem and solution awareness scale, and why it changes everything about your marketing
  • The three things you need to have in place to actually build an audience full of buyers, not just followers
  • Why realistic conversion rates matter, and how to set expectations so you can grow your business without burning yourself out

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

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DISCLAIMER

284. My Best Kept Secret That Feeds My Content, Testimonials, and $500k Launches13 Apr 202600:27:14

Automation is great — until it makes people forget there's a real human behind your business. In this episode, I'm pulling back the curtain on the tool I've been quietly using to generate content ideas, boost webinar show-up rates, and collect testimonials, all while making my audience feel personally connected to me. It contributed to a $500K launch, and I'm walking you through exactly how I use it for content, sales, and social proof.

In this episode, you'll hear…

  • What VideoAsk actually is and why it's more like FaceTiming your audience than filling out a form
  • How I'm using it to generate content ideas directly from my audience (in their own words)
  • The exact funnel I built to improve webinar show-up rates and make my workshop better in real time
  • How I'm collecting video testimonials that I can use in ads, social content, and more
  • Why building in "surprise and delight" moments is one of the highest-return investments you can make in your marketing

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

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DISCLAIMER

283. How I Actually Decide What to Send My Email List (Even When I Have No Idea)06 Apr 202600:30:08

If you've ever opened a blank document to write your newsletter and immediately closed it again, this one's for you.

I've been sending my weekly newsletter, Sam's Sidebar, consistently for years, and in this episode, I'm pulling back the curtain on exactly how I decide what to write every single week. Including the time I scrapped a completely finished email the morning it was supposed to go out, wrote something raw and real in about five minutes, and watched my inbox light up with replies all day long.

This is the behind-the-scenes process I use to make email feel less like a chore and more like one of the most powerful, reliable tools in my business.

In this episode, you'll hear…

  1. Why I always start by zooming out on my business before I write a single word
  2. How to reverse engineer your email from your call to action so everything you write actually has a point
  3. Why your call to action doesn't always have to be a sale (and what to do between launches)
  4. The one habit that makes finding topics infinitely easier, even when your brain is totally blank
  5. How I turned a frustrated, throw-it-all-out moment into one of my most-responded-to emails ever

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

EPISODE RESOURCES:

  1. Get Sam’s free weekly newsletter, Sam’s Sidebar
  2. Get your copy of Sam's book When I Start My Business, I'll Be Happy
  3. If you have a question you’d like Sam to answer on a future podcast episode, you can submit it here.
  4. Click here to be notified when new episodes of On Your Terms® come out

CONNECT:

  1. Get Sam's weekly newsletter, Sam's Sidebar
  2. Follow Sam on Instagram
  3. Follow Sam on YouTube
  4. Subscribe to Sam's Substack, Beyond Business
  5. Take Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"

DISCLAIMER

282: The End-of-Quarter Habit That Will Change How You Run Your Business30 Mar 202600:37:09

Q1 is officially in the books — so before you barrel headfirst into Q2, let's actually stop and take stock of how it went.

In this episode, I'm walking you through the end-of-quarter check-in I use in my own business — one that covers both your stats and your vibes — so you can go into the next quarter with one clear focus, a simple plan, and a lot less "why does running this business feel so chaotic?" energy.

We'll talk about how to look at your numbers without spiraling into a shame spiral, how to figure out whether you have a leads problem or a sales problem (because the answer totally changes your Q2 plan), and why the things that are draining you in your business are probably directly connected to what's not working in your data.

I'm also sharing my personal Q1 gap year update — what's working, what's not, the mastermind I very painfully said no to, and the morning routine that finally helped me get my writing practice off the ground.

In this episode, you'll hear…

  1. How to review your Q1 stats without spiraling into a shame spiral (the "curious scientist" approach is a game-changer)
  2. Why picking one single focus for Q2 will get you further than 16 half-finished goals ever will
  3. The "vibes check" — how to honestly assess how this quarter felt and what that means for Q2
  4. Why what's draining you in your business might be directly connected to what's not working in your stats
  5. My personal Q1 gap year update, including the mastermind I painfully said no to, the morning writing routine that finally clicked, and why "gap year" does NOT mean I'm sitting on a beach doing nothing

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

EPISODE RESOURCES:

  1. Get Sam’s free weekly newsletter, Sam’s Sidebar
  2. Sam's Substack post: Taking a Gap Year as an Entrepreneur: My Year of Letting Go in 2026
  3. Sam's Substack post: I called it a gap year—and everyone heard “year off.”
  4. Check out The Brick (affiliate link)
  5. Kit what I use to build my email list, send emails to my list, and create opt-in forms & pages (affiliate link)
  6. If you have a question you’d like Sam to answer on a future podcast episode, you can submit it here.
  7. Click here to be notified when new episodes of On Your Terms® come out

CONNECT:

  1. Get Sam's weekly newsletter, Sam's Sidebar
  2. Follow Sam on Instagram
  3. Follow Sam on YouTube
  4. Subscribe to Sam's Substack, Beyond Business
  5. Take Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"

DISCLAIMER

281. How I Made $500K in 4 Days (The Real Story)23 Mar 202601:01:10

Sam pulls back the curtain on her biggest launch ever — $500K in revenue in just four days. She's sharing the real numbers: 11,000 webinar registrants, a 5% conversion rate, and exactly what she spent on ads to get there. But this isn't just a brag fest — Sam gets honest about what's actually behind a launch like this, why you can't just copy someone else's formula, and what entrepreneurs at every stage can take away and apply to their own business.

Whether you're planning your first launch or looking to scale, this episode is packed with practical strategy on webinars, email list marketing, buyer objections, and building an online business that actually converts.

In this episode, you'll hear…

  1. The actual stats from my $500K launch — including webinar registrations, show-up rates, conversion percentages, and ad spend (yes, I'm sharing the numbers)
  2. Why I switched from three live webinars down to one — and how it actually increased my results
  3. The "show up" email strategy I use to get more people to attend the webinar live (and why it works way better than a basic reminder)
  4. How I think about Meta ads as their own social channel — and when you should (and absolutely should not) start running ads
  5. The three main buyer objections I prepare for in every launch — and how I use testimonials to overcome each one

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

EPISODE RESOURCES:

  1. Get Sam’s free weekly newsletter, Sam’s Sidebar
  2. Grab a copy of Sam's Book When I Start My Business, I'll Be Happy
  3. Read Sam's Substack post: I called it a gap year—and everyone heard “year off.”
  4. If you have a question you’d like Sam to answer on a future podcast episode, you can submit it here.
  5. Learn more about VideoAsk (affiliate link)
  6. Click here to be notified when new episodes of On Your Terms® come out

CONNECT:

  1. Get Sam's weekly newsletter, Sam's Sidebar
  2. Follow Sam on Instagram
  3. Follow Sam on YouTube
  4. Subscribe to Sam's Substack, Beyond Business
  5. Take Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"

DISCLAIMER

280. How I Got My First 1,000 Subscribers on Substack16 Mar 202600:42:44

Everyone's talking about Substack — and maybe you're curious, a little skeptical, and 100% wondering if you actually need to add another platform to your already-full plate. (Spoiler: you don't need to. But you might want to after this.)

In this episode, I'm pulling back the curtain on exactly how I grew my Substack, Beyond Business, to 1,000 subscribers using only organic strategies — no importing my 60,000+ person email list, no fancy custom design, no team of people building it out for me. Just consistent writing, a growth mindset, and a few simple (but powerful) tactics I wish I'd known earlier.

You’ll hear…

  • Why I started a Substack when I already have an email list of 60,000+ people (and why it's absolutely not an either/or decision)
  • The #1 mindset shift you need before you ever publish your first post Why becoming a fan of the platform first is one of the most underrated growth strategies out there
  • How I built a consistent writing habit — and what happened to my creativity when I actually stuck with it
  • The "idea bank" strategy that keeps me showing up even when inspiration goes on vacation
  • Why you need to bank essays before you let the world respond to your writing
  • How to use Substack Notes to grow your audience without burning out
  • The referrals and recommendations strategy I used to accelerate growth (and exactly how to ask for them without being weird about it)

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

EPISODE RESOURCES:


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DISCLAIMER

279. You Have to Get Good First (Then the Audience Follows)09 Mar 202600:34:32

If you’re trying to grow your audience for your online business, you’ve probably heard advice like “build the audience first” or “you need followers before you can launch.” But what if that’s backwards?

In this episode of On Your Terms®, Sam shares the real foundation of sustainable audience growth—and why focusing on followers, email list size, or social media metrics too early can actually slow you down. Instead, she breaks down how mastering your craft (whether that’s writing, podcasting, video, or your core service) is what truly builds an audience that sticks.

You’ll hear…

  1. Why obsessing over audience size can distract you from building actual skill
  2. The “wedding vs. marriage” analogy that changed how I think about growth
  3. What I realized after being in a mastermind with serious writers
  4. How to practice your craft in public without spiraling over metrics
  5. How to consume content in a way that fuels your output (instead of becoming a content junk drawer)
  6. A simple way to audit whether your time matches what you say you want

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

EPISODE RESOURCES:

  1. Get Sam’s free weekly newsletter, Sam’s Sidebar
  2. Subscribe to Sam's Substack, Beyond Business
  3. Get Sam's Book "When I Start My Business, I'll Be Happy"
  4. Click here to be notified when new episodes of On Your Terms® come out

CONNECT:

  1. Get Sam's weekly newsletter, Sam's Sidebar
  2. Follow Sam on Instagram
  3. Follow Sam on YouTube
  4. Subscribe to Sam's Substack, Beyond Business
  5. Take Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"

DISCLAIMER

278. Make This List If You're Burnt Out (It Changed Everything)02 Mar 202600:18:10

Have you ever heard a quote at exactly the moment you needed it? Like it practically reached out and grabbed you by the shoulders?

That happened to me recently when I heard this line from The Artist’s Way: "perfectionism isn’t a quest for the best… it’s a pursuit of the worst in ourselves.

Oof. Holy cannoli. That one knocked me flat.

In this episode, I’m sharing the simple exercise that helped me see my burnout in black and white—and how you can use it to finally exhale.

You’ll hear…

  1. The quote about perfectionism that stopped me in my tracks
  2. The unexpected way I realized I am a perfectionist (even though I swore I wasn’t)
  3. What I wrote on my “trying to do this perfectly” list—and why it shocked me
  4. How this one list immediately softened my burnout and anxiety
  5. Why doing “everything right” might actually be the thing holding you back

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

EPISODE RESOURCES:

  1. Click here to be notified when new episodes of On Your Terms® come out

CONNECT:

  1. Get Sam's weekly newsletter, Sam's Sidebar
  2. Follow Sam on Instagram
  3. Follow Sam on YouTube
  4. Subscribe to Sam's Substack, Beyond Business
  5. Take Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"

DISCLAIMER

277. The 6 Types of Rest (And Why Sleep Isn't Enough)23 Feb 202600:40:17

If you’re building a business, doing “all the right things,” and still feel exhausted even after a full night of sleep… this episode is for you.

So many entrepreneurs think rest is something you earn later — after the launch, after the revenue goal, after things finally feel “stable.” And that belief keeps you stuck in a cycle of pushing, white-knuckling, and wondering why you’re burned out even though you technically love your work.

I’m breaking down the 6 different types of rest, why sleep alone won’t fix burnout, and how I’ve been intentionally weaving more play, creativity, and relief into my life and business — without stepping away from work entirely.

In this episode, you’ll hear…

  • Why sleep isn’t the kind of rest most business owners actually need
  • The 6 types of rest and how burnout can show up even when you “love what you do”
  • How pressure, grief, and mental load quietly drain your energy
  • What it looks like to rest while building — not after
  • Simple ways to add more joy, play, and creativity into your everyday life

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

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DISCLAIMER

276. The Monthly Goals Method (Steal This)16 Feb 202600:37:53

It’s mid-February (or honestly… March… or April… or whenever you’re listening), and if your New Year’s goals already feel like they’ve floated off into the abyss — you’re not broken. You’re just human.

In this episode, I’m breaking down why January 1st is kind of a terrible time to set goals, especially if you’ve been navigating grief, uncertainty, burnout, or just… life. I’m sharing how I actually set goals now using a monthly goals method that’s way more realistic, flexible, and supportive — and yes, you’re absolutely allowed to steal it.

In this episode, you’ll hear…

  1. Why January 1st isn’t actually a clean slate (and never has been)
  2. How grief, uncertainty, and burnout affect goal-setting more than we admit
  3. The monthly goals method I use instead of New Year’s resolutions
  4. How to set goals when you don’t feel clear or motivated
  5. Ways to bring “new year energy” into any month of the year
  6. How to stay present and profitable without rigid long-term plans

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

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DISCLAIMER

275. 6 Lessons I Wish I Knew 5 Years Ago09 Feb 202600:38:53

There’s this moment in business where you keep thinking, okay… when does it get easier? When does the stress chill out, the money feel steadier, and you finally get to enjoy what you’re building?

Here’s the sneaky truth I wish someone had told me sooner: the “someday” version of your life isn’t where the joy starts. The rise is actually the fun part.

In this episode, I’m sitting down with the version of myself from five years ago (hello, 2021 Sam) and sharing the six lessons I wish I could’ve handed her in a note. These aren’t fluffy business platitudes — they’re the real, lived-in truths that only come from building a seven-figure business, navigating massive personal loss, and realizing the mountaintop doesn’t feel the way everyone promises it will

In this episode, you’ll hear…

  • Why the rise is actually the best part (even when it feels messy)
  • The hard truth about the “carrot” always moving in business
  • How chasing someone else’s version of success can quietly wreck your joy
  • Why you don’t need to be “one of them” to build a wildly successful business
  • How to stay confident being a leader — especially when new platforms and trends pop up
  • The simple mindset shift that helped me finally loosen my grip on control

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

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DISCLAIMER

How To Legally Protect & Grow Your Online Business in 202609 Feb 202601:21:33

In this episode, you get to hear my full live training, “How To Legally Protect & Grow Your Online Business in 2026.” I’ll give you the five steps every entrepreneur needs to take. We’ll cover shifting your mindset, registering as the right business entity, protecting yourself in case of a lawsuit, getting your contracts and policies in place, and staying within your scope of practice.

Whether you’re a coach, course creator, service provider, or product-based entrepreneur, I’m walking you through the five simple legal steps you must take to set up your business, protect your content, and get paid confidently.

No law degree (or stress spiral) required.

In this episode, you’ll hear…

  • 5 things you must have in place before accepting even $1 (more) online
  • Exact steps to form your business
  • Should you become an LLC or sole prop? 
  • Why you NEED to have business insurance (it’s so worth it)
  • An actual method for figuring out what you can (and cannot) do online or when you’re NOT working under your professional license

RESOURCES:


CONNECT:

  1. Sam on Instagram
  2. Sam on Facebook
  3. On Your Terms® on Instagram

DISCLAIMER

274. 4 Tiny Shifts I Make Every Winter (so I feel cozy, not crushed)02 Feb 202600:18:11

When it gets dark before you’ve even wrapped up work for the day, winter can feel like it shrinks your whole life. Suddenly everything feels harder, heavier, and honestly… a little bleak. And while part of you might want to hibernate until April, another part of you knows that doesn’t really work when you’re running a business and trying to live a full life.

In this episode, I’m sharing how I’ve learned to actually work with winter instead of fighting it. After moving from Philly to the north shore of Long Island (where winter is colder, darker, windier, and somehow five degrees colder just to be rude), I had to build a real winter toolkit — not just cozy socks, but mindset shifts, routines, and intentional rituals that make this season feel supportive instead of soul-crushing.

In this episode, you’ll hear…

  • Why your relationship with winter might be making it harder than it needs to be
  • The mindset shift that completely changed how I experience winter
  • How I intentionally design winter to feel cozy, grounding, and even enjoyable
  • Why winter is actually essential for creativity, energy, and long-term sustainability
  • Simple routines and rituals that give you something to look forward to all season long

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

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DISCLAIMER

273. I Refilmed My Entire Signature Program (Here’s What I Didn’t Expect)26 Jan 202600:32:03

Re-shooting all the videos for a product that’s generated over $8 million sounds like a straightforward business upgrade… until it isn’t.

In this episode, I’m taking you behind the scenes of what it was really like to re-record every single video inside the Ultimate Bundle®. Spoiler alert: this was about way more than lighting, scripts, or batch recording. It cracked open a lot for me — about grief, seasons of business, fear of slowing down, and the pressure we put on ourselves to constantly “improve” things that are already working.

If you’ve ever felt overwhelmed by a big project, nostalgic for earlier seasons of your business, or quietly scared of what might happen if you let yourself rest, this episode is for you.

In this episode, you’ll hear…

  • Why re-shooting the Ultimate Bundle® felt more like reliving the bar exam than a simple content update
  • What building an MVP actually looks like over eight years of growth
  • The hidden cost of having a wildly successful signature product
  • How grief, loss, and survival mode quietly shaped my business from 2020 on
  • Why “easy” seasons of business can feel surprisingly uncomfortable
  • What early-stage hustle teaches you that success sometimes takes away
  • How I approached updating a proven product without burning it all down

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

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DISCLAIMER

272. What Happened When I Actually Took My Screen Time Seriously for 30 Days19 Jan 202600:26:53

We all know that moment. It’s Sunday. Your phone buzzes. And suddenly you’re staring down your weekly screen time report wondering… how did THAT happen?

For me, those little reports started to feel like a mirror I didn’t really want to look into. The number on the screen didn’t line up with the life I said I wanted to be living—more present, less irritable, doing deeper work, and actually enjoying my days instead of scrolling through them.

So I decided to stop ignoring it and actually take my screen time seriously. In this episode, I’m sharing what happened when I did just that—for 30 days.

This isn’t about deleting every app or pretending your phone isn’t a major part of your business (because let’s be real… it is). It’s about creating a healthier relationship with your phone so it can be a tool instead of an appendage—and building a business that doesn’t require you to be glued to it 24/7.

If you want to be more present in your life and more profitable in your business, this episode is for you.

In this episode, you’ll hear…

  • Why your screen time report can reveal way more about your life than you think
  • How I reduced my screen time without shame, guilt, or extreme rules
  • The difference between “productive” screen time and the kind that quietly drains you
  • The app that consistently sends me into a doom-scrolling spiral (and what I do about it)
  • How to find your personal tipping point with screen time—without comparing yourself to anyone else

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

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DISCLAIMER

271. Substack vs. My Newsletter: What Goes Where (and Why)12 Jan 202600:31:05

If you’ve been side-eyeing Substack trying to figure out whether you should start one, what you’d even put on it, or how it’s different from your “regular” newsletter… this episode is your permission slip to breathe. Because guess what? I’ve been figuring this out in real time too — and today, I’m breaking down exactly how I’m using both Substack and my newsletter, why I treat them differently, and how YOU can create a simple, sustainable content structure that actually supports your business.

I’ll also walk you through the discovery → nurture → conversion framework I use to decide which platforms get my energy — and which ones simply get a presence without becoming a second job. Because you are absolutely not meant to create cornerstone content for 19 platforms. No thank you.

Whether you’re Substack-curious, newsletter-confused, or trying to design a content flow that doesn’t make you want to run away to a cabin in the woods, this episode will give you clarity.

In this episode, you’ll hear…

  1. How I’m using Substack differently from my weekly business newsletter
  2. Why your content should flow from one or two core platforms (not all of them)
  3. The discovery–nurture–conversion method I use to understand where each platform fits
  4. How I’m thinking about Substack as an experiment (and why that’s OK!)
  5. What goes on Substack vs. what stays in my main newsletter
  6. How to decide where YOUR content belongs without overthinking it

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

RESOURCES:

  1. Get Sam’s free weekly newsletter, Sam’s Sidebar
  2. Subscribe to Sam's Substack Beyond Business
  3. Get Sam's book "When I Start My Business, I'll Be Happy"
  4. Listen to Sam on Cubicle to CEO Episode 293. 46k List Growth Case Study: From Snooze-Worthy To Subscriber Magnet
  5. Writing a Book Podcast Playlist
  6. Kit - what I use to build my email list, send emails to my list, and create opt-in forms & pages (affiliate link)
  7. Click here to be notified when new episodes of On Your Terms® come out
  8. Click here to watch the free workshop so you can get legally protected right now!

CONNECT:

  1. Get Sam's weekly newsletter, Sam's Sidebar
  2. Follow Sam on Instagram
  3. Follow Sam on YouTube
  4. Subscribe to Sam's Substack, Beyond Business
  5. Take Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"
  6. DISCLAIMER

DISCLAIMER

270. Is AI Quietly Killing My Creativity?05 Jan 202600:31:15

Let’s talk about the thing I didn’t even realize was happening until it had already messed with my head: AI was quietly killing my creativity.

If you’ve ever opened your laptop, told yourself you’re “just getting a little AI help,” and then suddenly noticed your ideas feel watered down, your content feels off, and you’re second-guessing everything—you’re not alone. When I posted about this on Instagram, you confirmed that this little creep has been slipping into your business too… and not in the cute, helpful way we hoped.

So today, I’m getting brutally honest about how AI slowly started impacting my creativity, confidence, workflow, and even the way I approached this podcast. This episode is your reminder that your most valuable business asset is your brain—your original ideas—not a robot’s outline telling you how you should create.

In this episode, you’ll hear…

  1. How AI slowly crept into my creative process without me realizing it
  2. The dangerous shift from “this helps” → “this must know better than me”
  3. How AI’s feedback made me doubt my instincts and dry up my idea well
  4. The moment I realized AI was contributing to a huge creativity block
  5. What happened when I quit using AI for outlines, brainstorming, and feedback
  6. The difference between using AI as a repurposing tool vs. as a creator
  7. The creative habits and practices I’m returning to in 2026
  8. How to rebuild your originality in a world obsessed with shortcuts

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

RESOURCES:

  1. Get Sam’s free weekly newsletter, Sam’s Sidebar
  2. Subscribe to Sam's Substack Beyond Business
  3. Get Sam's book "When I Start My Business, I'll Be Happy"
  4. My Instagram Reel on quitting ChatGPT
  5. Listen to Episode 140. We Need To Talk About Dupe Culture
  6. Meet Your AI All Stars Course (affiliate link)
  7. Grab the Ultimate Bundle®
  8. Click here to be notified when new episodes of On Your Terms® come out
  9. Click here to watch the free workshop so you can get legally protected right now!

CONNECT:

  1. Get Sam's weekly newsletter, Sam's Sidebar
  2. Follow Sam on Instagram
  3. Follow Sam on YouTube
  4. Subscribe to Sam's Substack, Beyond Business
  5. Take Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"

DISCLAIMER

269. 4 Tiny Habits I Do Before Year-End (So 2026 Is More Profitable and Peaceful)15 Dec 202500:16:03

You know that feeling when you come back to your desk in January and everything is a disaster? Your desktop looks like a digital garage sale, your office chair is still wearing yesterday’s sweater, and your brain feels like it’s running 42 tabs at once?

Yeah… we’re not doing that this year.

In this episode, I’m sharing the super simple, totally doable tasks I’m doing in the next two weeks—while cozied up in my pjs —to close out 2025 in a way that feels calm, grounded, and actually restorative. No “new year, new hustle” energy required. Just a cleaner home base, a quieter mind, and a business you can step back into without the chaos hangover.

This is your permission slip to put the laptop away, clean the slate, and give your future self a January that feels good.

In this episode, you’ll hear…

  1. The 4 things I always do to wrap up my business before the holidays
  2. Why I deep clean everything (yes, including the dreaded office drawer) before taking time off
  3. How I’m approaching 2026 as a “mental gap year”
  4. My end-of-year digital detox ritual
  5. What I’m doing during my time off to reconnect with creativity
  6. The cozy winter habits keeping me sane in an extremely dark, extremely windy Long Island winter

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

RESOURCES:

  1. Get Sam’s free weekly newsletter, Sam’s Sidebar
  2. Get Sam's book "When I Start My Business, I'll Be Happy"
  3. Listen Episode 267: Before You Plan 2026, do THIS first
  4. Listen to Episode 268: How to Create Your Ideal Business Year (Without Burnout-y Goals)
  5. Grab the Ultimate Bundle® and use code OYTWRITEOFF to save 20% off through December 18th.
  6. Read Sam's Substack Taking a Gap Year as an Entrepreneur: My Year of Letting Go in 2026
  7. Click here to be notified when new episodes of On Your Terms® come out
  8. Click here to watch the free workshop so you can get legally protected right now!

CONNECT:

  1. Get Sam's weekly newsletter, Sam's Sidebar
  2. Follow Sam on Instagram
  3. Follow Sam on YouTube
  4. Subscribe to Sam's Substack, Beyond Business
  5. Take Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"

DISCLAIMER

268. How to Create Your Ideal Business Year (Without Burnout-y Goals)08 Dec 202500:28:06

It’s that time of year again — when everyone online suddenly becomes a color-coded-notion-board-wielding planning expert. But before you map out your entire 2026 vision board, we need to do something way more important: figure out what you actually want.

In today’s episode, I’m walking you through the exact reflection + annual planning exercise I do every single year — the one that helps me make decisions based on how I want to feel, not what the latest marketing trend says I “should” be doing. This episode pairs with last week’s 2025 reflection episode, so if you haven’t listened to that one yet, go queue it up next.

PLUS — I’m trying something new today. I pulled a random question from the “More, Tell Me More” connection cards I won at a mastermind retreat (yes, I was voted Best Strategy at my table and the whole room — no biggie). I answered it… and I want you to answer it too. If you love this segment, email me or DM me and tell me to keep it!

And before you dive in, don’t forget: I created a free 2026 Annual Planning Guide that includes every question I ask in this episode and space for you to jot down your reflections and goals. Grab it in the show notes!

In this episode, you’ll hear…

  1. The connection-card question I pulled — and the unforgettable story about the stranger who changed how I think about human connection
  2. Why planning for 2026 means starting with how you want to feel (not arbitrary goals like “50K followers”)
  3. How to imagine your ideal day next year so you can reverse-engineer what needs to change
  4. Why so many entrepreneurs felt unstable in 2025 — and how to honor what actually happened before planning ahead
  5. The questions I use every year to figure out what I truly need in my business and personal life
  6. A guided reflection to set aligned, realistic, energizing goals for 2026

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

RESOURCES:

  1. Get Sam’s free weekly newsletter, Sam’s Sidebar
  2. Get Sam's book "When I Start My Business, I'll Be Happy"
  3. Listen to the How to Grow Your Email List Series Playlist
  4. Subscribe to Sam's Substack Beyond Business
  5. Download Sam's Annual Planning Guide
  6. Click here to be notified when new episodes of On Your Terms® come out
  7. Click here to watch the free workshop so you can get legally protected right now!

CONNECT:

  1. Get Sam's weekly newsletter, Sam's Sidebar
  2. Follow Sam on Instagram
  3. Follow Sam on YouTube
  4. Subscribe to Sam's Substack, Beyond Business
  5. Take Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"

DISCLAIMER

267. Before You Plan 2026, Do THIS First01 Dec 202500:40:57

If you’re anything like me, you’ve probably hit the end of the year and thought:

Wait… what actually happened?!

How did we blink and suddenly find ourselves staring down a new calendar, new goals, and the same coffee mug we’ve dragged through the highs and lows of the last 12 months?

Before you sprint into planning mode for 2026 (don’t worry, we’re doing that next week!), today’s episode is all about slowing down long enough to look back—at what worked, what didn’t, what you let go of, what you gained, and most importantly… how it all felt.

Because building a business on your terms means regularly checking in with yourself—not just the metrics, money, or milestones, but the very real human (you!) behind all of it.

Inside this episode, I walk you through the exact year-end reflection process I do myself, including the six life categories I evaluate every single December to help me understand what’s out of balance, what’s thriving, and where I want to direct my energy next.

Grab your notebook, a cup of something warm, and prepare for some gentle-but-honest self-inquiry.

In this episode, you’ll hear…

  • The six life categories I use to check in with myself each year
  • Why reflecting before planning will make your 2026 goals actually stick
  • The progress-based mindset shift that will keep you motivated all year long
  • What to ask yourself about what you accomplished, added, and let go of
  • How to identify your “accelerators” and “constrictors” going into a new year

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

RESOURCES:


CONNECT:


DISCLAIMER

266. How to Grow Your Email List (Series #4)24 Nov 202500:41:41

If you’ve ever stared at a blinking cursor while trying to write your weekly newsletter and thought, “What in the whole enchilada am I supposed to say?” — today’s episode is your permission slip to stop overthinking and start structuring your emails in a way that works for you and your audience.

I’m breaking down the two classic newsletter formats (and why I don’t follow either), the hybrid structure I swear by, and the eight must-have elements your weekly emails need if you want them to be opened, read, clicked, and shared.

Whether you're brand new to email marketing or finally ready to clean up the spaghetti-at-the-wall approach we all start with — this episode gives you practical steps to build a bingeable, forwardable, valuable email your people will look forward to every week.

In this episode, you’ll hear…

  1. The two traditional newsletter formats — and why a hybrid approach wins
  2. Why story-driven writing builds connection (and how to use it well)
  3. How to structure “predictable sections” and weekly “boxes” your audience can rely on
  4. The three core goals every email should have (and how to choose yours each week)
  5. How many links to include — and the right balance between your content vs. other people's
  6. Eight essentials you must include in your weekly newsletter
  7. How to write subject lines + preview text that actually get opened
  8. My #1 habit that instantly elevates the quality of your emails (and makes them sound human)

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

RESOURCES:

  1. Get Sam’s free weekly newsletter, Sam’s Sidebar
  2. Listen to Part 1, Part 2 & Part 3 of the "How To Grow Your Email List" Series
  3. Download the free “How to Grow Your Email List” Workbook
  4. Get Sam's book "When I Start My Business, I'll Be Happy"
  5. Listen to Epi 262. The 6 Weekly Anchors Behind My $8M Business
  6. Watch my email walkthrough training
  7. Click here to be notified when new episodes of On Your Terms® come out
  8. Click here to watch the free workshop so you can get legally protected right now!

CONNECT:

  1. Get Sam's weekly newsletter, Sam's Sidebar
  2. Follow Sam on Instagram
  3. Follow Sam on YouTube
  4. Subscribe to Sam's Substack, Beyond Business
  5. Take Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"

DISCLAIMER

265. How to Grow Your Email List (Series #3)17 Nov 202500:28:58

Let’s be honest — most freebies out there? They’re not working.

If you’ve ever spent hours creating a lead magnet only for it to attract people who download and disappear, this episode is your new best friend.

In Part 3 of my 4-part email series, I’m breaking down why your freebie isn’t growing your list (hint: it’s not because freebies don’t work) and how to finally create one that brings in actual future customers — not just freebie hoarders.

From finding the perfect topic your people actually want to grabbing the right metrics to track whether it’s working, this episode gives you the full roadmap to a freebie that converts

In this episode, you’ll hear…

  1. Why most freebies flop — and how to fix yours
  2. The #1 rule for creating a freebie your audience can’t resist
  3. How to reverse engineer your freebie from your offer
  4. The secret to positioning your freebie so it attracts buyers, not browsers
  5. Which numbers to track to know if your email list is really growing

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

RESOURCES:

  1. Get Sam’s free weekly newsletter, Sam’s Sidebar
  2. Listen to Part 1 & Part 2 of the "How To Grow Your Email List" Series
  3. Download the free “How to Grow Your Email List” Workbook
  4. Listen to Part 1 of "How To Grow Your Email List" Series
  5. Click here to be notified when new episodes of On Your Terms® come out
  6. Click here to watch the free workshop so you can get legally protected right now!

CONNECT:

  1. Get Sam's weekly newsletter, Sam's Sidebar
  2. Follow Sam on Instagram
  3. Follow Sam on YouTube
  4. Subscribe to Sam's Substack, Beyond Business
  5. Take Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"

DISCLAIMER

264. How to Grow Your Email List (Series #2)10 Nov 202500:34:17

You’ve been told that the only way to grow your email list is with freebies, PDFs, and opt-ins galore—but what if there was an easier (and honestly, more effective) way?

In Part 2 of my How to Grow Your Email List series, I’m spilling the details on my Easy Email Strategy—a super simple way to get the right people (aka future customers, not freebie collectors) on your list without creating a single freebie.If you’ve ever felt frustrated with the traditional “freebie → nurture sequence → maybe they’ll stick around” method, this episode will feel like a breath of fresh air. You’ll learn how to make your actual newsletter the thing people want to sign up for—and how to position it so it grows your list on autopilot.

In this episode, you’ll hear…

  1. Why traditional freebie funnels often attract the wrong people
  2. How to flip the script and make your newsletter the value
  3. The two steps in my Easy Email Strategy: design + promotion
  4. How to create a newsletter people are genuinely excited to receive
  5. Real-world examples of how this strategy simplifies your marketing

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

RESOURCES:

  1. Get Sam’s free weekly newsletter, Sam’s Sidebar
  2. Download the free “How to Grow Your Email List” Workbook
  3. Listen to Part 1 of "How To Grow Your Email List" Series
  4. Check out Erin Parek's Substack
  5. Click here to be notified when new episodes of On Your Terms® come out
  6. Click here to watch the free workshop so you can get legally protected right now!

CONNECT:

  1. Get Sam's weekly newsletter, Sam's Sidebar
  2. Follow Sam on Instagram
  3. Follow Sam on YouTube
  4. Subscribe to Sam's Substack, Beyond Business
  5. Take Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"

DISCLAIMER

263. How to Grow Your Email List (Series #1)03 Nov 202500:33:20

You’re doing everything to grow your email list — promoting your freebies, sharing your links, posting on social — and yet, that number just won’t budge. You want new subscribers rolling in every day, the kind who actually want to buy from you, and a reliable way to make sales that doesn’t depend on Instagram’s mood swings.

Sound familiar?

In this first episode of my 4-part Email List Growth Series, I’m breaking down what it really takes to build a thriving email list that fuels your business (and your freedom). It’s not about hacks or fancy tech — it’s about adopting an “all roads lead to the email list” mindset and taking strategic action to support it.

Because when your email list becomes the heartbeat of your business, you can take weekends off, go on vacation without stress, and still make sales while you sleep.

In this episode, you’ll hear…

  1. Why your email list growth starts with mindset — not hacks
  2. The three key steps to adopting an “All Roads Lead to the Email List” approach
  3. How to clarify what your email list actually does for your business
  4. How to audit your current strategy (and find the leaks)
  5. The simple way to spot new email list opportunities everywhere
  6. A sneak peek of what’s coming in Part 2 — my easy email list growth strategy

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

RESOURCES:

  1. Get Sam’s free weekly newsletter, Sam’s Sidebar
  2. Download the free “How to Grow Your Email List” Workbook
  3. Listen to Ep 237. Why Your Email List Isn't Growing +How to Fix It
  4. Click here to be notified when new episodes of On Your Terms® come out
  5. Click here to watch the free workshop so you can get legally protected right now!

CONNECT:

  1. Get Sam's weekly newsletter, Sam's Sidebar
  2. Follow Sam on Instagram
  3. Follow Sam on YouTube
  4. Subscribe to Sam's Substack, Beyond Business
  5. Take Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"

DISCLAIMER

262. The 6 Weekly Anchors Behind My $8M Business (That Have Nothing to Do With Marketing)27 Oct 202500:48:31

You’ve probably heard me say before that your business only grows as much as you do — and I mean it.

Because no matter how many marketing tricks you try, or how well you plan your next launch… none of it matters if you’re running on fumes.

In today’s episode, I’m sharing the six weekly anchors that keep me grounded, creative, and energized enough to run an $8M business — and not one of them has to do with marketing. These are the personal routines and boundaries that have built the foundation for everything I’ve accomplished in my business and my life.

Whether you’re building toward your first six figures or scaling beyond seven, these anchors will help you protect your energy, your creativity, and your mental health — the real ingredients of long-term success.

In this episode, you’ll hear…

  • Why taking care of yourself is one of the most strategic business decisions you can make
  • What my “Sunday Preheat” routine looks like (and how it keeps my week from falling apart)
  • The planning process I use each week to set priorities and avoid overwhelm
  • How I protect time for movement, rest, and creativity — even when my schedule’s packed
  • The mindset shift that helped me stop seeing self-care as “extra”
  • How you can create your own set of anchors that make your business (and your life) work better

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

RESOURCES:


CONNECT:


DISCLAIMER

261. How to Start an Online Business (legally!)21 Oct 202501:12:11

Thinking about starting an online business—or finally making your “side hustle” official—but don’t want to get buried in legal confusion? This episode is your crash course on exactly how to start your business the right way before 2025 ends.

Whether you’re a coach, course creator, service provider, or product-based entrepreneur, I’m walking you through the five simple legal steps you must take to set up your business, protect your content, and get paid confidently.

No law degree (or stress spiral) required.

In this episode, you’ll hear…

  1. 5 things you must have in place before accepting even $1 (more) online
  2. Exact steps to form your business
  3. Should you become an LLC or sole prop?
  4. Why you NEED to have business insurance (it’s so worth it)
  5. An actual method for figuring out what you can (and cannot) do online or when you’re NOT working under your professional license
  6. Your 2025 To-do List: things to do before Dec 31st to make your biz legally sound

RESOURCES:

  1. The Ultimate Bundle® is on sale through Oct 24, 2025. If you buy it before Oct 22nd, 2024, you’ll receive 3 bonus templates + my last live call of the year.

CONNECT:

  1. Get Sam's weekly newsletter, Sam's Sidebar
  2. Follow Sam on Instagram
  3. Follow Sam on YouTube
  4. Subscribe to Sam's Substack, Beyond Business
  5. Take Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"

DISCLAIMER

260. How to Actually Build to Multi-7 Figures (and the Trade-Offs No One Mentions)13 Oct 202500:45:26

Everyone wants the 7-figure business… until they realize what comes with it.

In this episode, I’m breaking down what it really takes to build a multi-seven-figure online business — and the trade-offs no one warns you about. I’ll share the 10 things I’d focus on if I were starting over, including how to create a flagship product that actually sells, the “3 Ps” I swear by for sustainable growth, and why making more money doesn’t automatically mean you’re taking more home.

If you’ve ever wondered what it actually looks like to grow a business beyond six figures (without losing your sanity or your joy), this episode is your behind-the-scenes reality check — and roadmap.

In this episode, you’ll hear…

  1. Why only 1% of one-person businesses ever hit $1M/year
  2. The 10 things I’d do to build a seven-figure business from scratch
  3. The difference between profitable growth and burnout growth
  4. Why your flagship product is the foundation for everything
  5. The real emotional and personal trade-offs of scaling big
  6. How to know if a seven-figure business is actually what you want

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

RESOURCES:

  1. Get Sam's book "When I Start My Business, I'll Be Happy: A Practical No-BS Guide to Successful Entrepreneurship"
  2. Get Sam’s free weekly newsletter, Sam’s Sidebar
  3. Episode 243: Why Your Content is Driving Customers Away
  4. Episode 256: How To Protect Your Privacy While Growing Your Business
  5. Episode 259: Passion Doesn't Equal Profit (Why Your Idea Might Fail)
  6. Click here to watch the free workshop so you can get legally protected right now!

CONNECT:

  1. Get Sam's weekly newsletter, Sam's Sidebar
  2. Follow Sam on Instagram
  3. Follow Sam on YouTube
  4. Subscribe to Sam's Substack, Beyond Business
  5. Take Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"

DISCLAIMER

259. Passion Doesn't Equal Profit (And How to Fix It)06 Oct 202500:33:08

So you love something—cooking, crafting, wellness, design—and you think, this is it, this is going to be my dream business! But then… crickets. No sales, no growth, no happy dance notifications from Stripe. Sound familiar?

Here’s the thing: passion is wonderful, but passion alone doesn’t pay the bills. In this episode, I’m sharing my own story of turning my love for cooking into a failed business (ouch) and the exact lessons I learned that helped me build a seven-figure business the second time around.

I’m breaking it all down into three “chapters” so you can see how to go from high passion/low strategy → sustainable, profitable business you actually love running.

In this episode, you’ll hear…

  1. Why starting a business on pure passion can actually set you up for burnout and disappointment
  2. The most common mistake new entrepreneurs make when turning a hobby into a business (I made it too!)
  3. How to shift from thinking about what you want to what your audience actually needs
  4. What to do when the excitement wears off and the sales don’t come rolling in
  5. How to tweak your idea so it’s both fulfilling and profitable

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

RESOURCES:

  1. Get Sam’s free weekly newsletter, Sam’s Sidebar
  2. Get Sam's book "When I Start My Business, I'll Be Happy: A Practical No-BS Guide to Successful Entrepreneurship"
  3. Listen to The Real Cure for Burnout Isn't Rest - It's Creativity. Here's How Anyone Can Unlock Theirs
  4. Click here to watch the free workshop so you can get legally protected right now!

CONNECT:

  1. Get Sam's weekly newsletter, Sam's Sidebar
  2. Follow Sam on Instagram
  3. Follow Sam on YouTube
  4. Subscribe to Sam's Substack, Beyond Business
  5. Take Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"

DISCLAIMER

258. How I Grow My Business in Q4 (Without Ever Running a Black Friday Sale)29 Sep 202500:11:30

Most entrepreneurs think Q4 is a “dead zone” for sales—too many ads, too much noise, everyone distracted by holidays. But let me tell you: I’ve grown my multi–seven-figure business in the last 90 days of the year without ever running a Black Friday sale.

That’s right—no discounts on Thanksgiving, no frantic cyber deals, and no giving up my pumpkin pie to answer DMs. 🙅🏻‍♀️

Instead, I use five simple strategies every single year to not just end the year strong, but to set up massive momentum for the following year. And they work. Today, I’m walking you through exactly how I plan for growth in Q4 so you can steal my playbook.

In this episode, you’ll hear…

  1. How to use end-of-year messaging to spark urgency and action from your audience
  2. The behind-the-scenes planning I do in Q4 that fuels my January/February launches
  3. Why “showing up like normal” (even when everyone else taps out) has been one of my biggest growth secrets
  4. A sneaky way to run a holiday sale without competing in the Black Friday chaos
  5. How tax deductions can be the secret sales booster no one’s talking about

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

RESOURCES:

  1. Get Sam’s free weekly newsletter, Sam’s Sidebar
  2. Click here to watch the free workshop so you can get legally protected right now!

CONNECT:

  1. Get Sam's weekly newsletter, Sam's Sidebar
  2. Follow Sam on Instagram
  3. Follow Sam on YouTube
  4. Subscribe to Sam's Substack, Beyond Business
  5. Take Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"

DISCLAIMER

© My Podcast Data · Projet indépendant · Données issues d'Apple & Spotify
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