On Your Terms®

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 m...

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 proble...

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 i...

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...

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"...

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...

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...

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, swi...

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...

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...

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 t...

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 pres...

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 meant...

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...

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 p...

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...

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...

“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...

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 cou...

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'r...

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 fou...

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...

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 fi...

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 basi...

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...