On Your Terms®

If you've ever wondered what really goes down behind the scenes at a big-name business conference like ConvertKit’s Craft + Commerce, I’ve got the juicy details for you—straight from the hallways of Boise, Idaho.

In this week’s episode of On Your Terms®, I’m taking you along for the ride as I share what it was like to not only attend but speak at Craft + Commerce this year. But spoiler alert: the real magic? It wasn’t just in the keynotes or workshops. It was in the dinners, hallway chats, and the unexpected conversations with people who get what it’s like to build a business while living a full, complex life.

In this episode, you’ll hear…

1. The story behind my first time speaking at Craft + Commerce
2. What she really talked about on stage (it’s not what you think)
3. The real value of community when you’re grieving and growing a business
4. The surprising email marketing tactics top creators are actually using right now
5. What’s being whispered in the hallways about the future of online entrepreneurship

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

RESOURCES:

1. Order Sam's book: When I Start My Business, I’ll Be Happy
2. Sign up for my weekly email: Sam’s Sidebar
3. Kit (affiliate link) what I use to build my email list, send emails to my list, and create opt-in forms & pages
4. Sam's interview with Matt Gira
5. Listen to Sam’s episode on Smart Passive Income
6. Check out Jen Diaz and The JAVA Method
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

Starting an online business is super exciting—you're finally working with customers, launching offers, and maybe even making some money. But what if you’ve unknowingly skipped a legal step that could derail everything?

In this episode, I’m breaking down the 7 most common (and totally preventable!) legal mistakes I see new entrepreneurs make—plus, how to avoid each one so your business is built on a solid legal foundation.

This episode is packed with real-talk examples, actionable tips, and a whole lot of myth-busting. If you’ve ever wondered when to get legal protection, whether you really need business insurance, or if those “free policies” from your course platform are enough—this one’s for you.

In this episode, you’ll hear…

1. Why waiting to “get legal” until you’re more successful could cost you big time
2. The #1 mindset shift you need to build a future-proof business
3. What to do instead of obsessing over trademarks before you even have a business
4. Why DIY-ing contracts through Google or ChatGPT is a legal disaster waiting to happen
5. The hidden danger behind free templates from course and membership platforms
6. What most people misunderstand about business insurance (and when you actually need it)
7. Why having legal protection early helps you raise your prices, show up more, and actually grow

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

RESOURCES:

1. Grab the Ultimate Bundle® on sale for $400 off plus a bunch of exclusive bonuses!
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

So you’ve got the business idea. You might even have the Instagram handle locked down. But now you're stuck staring at your laptop like... “What legal steps am I supposed to take to make this real?”

If that sounds like you, you’re not alone—and you’re in the right place.

In this episode of On Your Terms®, I walk you through the exact checklist of what to do (in order!) to legally set up your online business. Whether you’re a coach, digital product creator, or service provider, I’m giving you a clear, three-day action plan to get your business legally legit—without the legal jargon, guesswork, or overwhelm.

This is the episode that takes you from “OMG where do I even start?” to “Wow, I actually did that!”

Let’s walk through the 5 essential legal steps (plus a bonus) every online business owner needs to take from day one.

In this episode, you’ll hear…

1. How to finally stop Googling and start doing with a 3-day legal setup checklist
2. The 4 things to knock out on day 1 (and how quickly you can do them)
3. What you need to open a business bank account—and why it’s not optional
4. How to legally accept payments online (the right way)
5. What kind of contract you need based on what you sell
6. My thoughts on LLCs vs. sole proprietorships (and what could get you in trouble)

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

RESOURCES:

1. Grab my free legal guide "The Ultimate Legal Guide for Online Entrepreneurs"
2. Sign up for Sam's Sidebar, my weekly email, to receive legal tips & marketing advice that I implement in my 7 figure business

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

Ever feel like your brain is bloated from binging on too many business tips, tutorials, and trending strategies?

Yep, same. It’s like we’ve all been force-fed a buffet of content, but no one told us how to actually digest it.

That’s exactly what I talked about in this week’s episode of On Your Terms® with the amazing Pat Flynn — longtime online business leader, podcaster, author, and Pokémon enthusiast (yes, really!).

Pat’s got a new book out called Lean Learning, and he’s here to share how you can stop swirling in the sea of “just-in-case” info and start actually moving your business forward with less learning, more doing. If you’re tired of feeling stuck even though you’re trying to “do all the right things,” this one’s for you.

In this episode, you’ll hear…

1. What “information obesity” is and how it’s quietly holding your business back
2. Why more knowledge isn’t what you need — and what to focus on instead
3. The real difference between “just-in-time” vs. “just-in-case” learning
4. Why implementing as you go beats learning everything upfront
5. How Pat built a 7-figure business by taking imperfect action
6. How to create your own “force functions” to finally make progress
7. What Pokémon collecting taught Pat about entrepreneurship (yes, seriously!)

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

RESOURCES:

1. Check out Pat’s new book www.leanlearningbook.com
2. Check out Pat on YouTube: Pat Flynn // Deep Pocket Monster // Short Pocket Monster
3. Sign up for Pat’s newsletter: https://patflynn.com/
4. Listen to Sam’s episode on Smart Passive Income
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

Ever feel like you’re showing up consistently—posting, emailing, sharing—only to be met with… crickets? You’re pouring your heart into your content, but it’s not converting into customers. What gives?

In this episode, I’m breaking down a mistake I made with healthy brownies (yes, really) that’s basically a marketing metaphor for why your content might not be working. It turns out, if you’re leading with broccoli when your audience really wants mac and cheese, they’ll pass every time—even if it’s good for them.

This one’s short, sweet, and will change the way you write content forever.

In this episode, you’ll hear…

1. Why your content might be falling flat even when it’s technically “good”
2. The “brownie story” that reveals a powerful marketing truth
3. How to identify your audience’s version of mac and cheese
4. A simple framework for layering value (aka broccoli) into crave-worthy content
5. What to say instead so your audience finally bites

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

RESOURCES:

1. Sign up for my free weekly email Sam’s Sidebar
2. Click here to watch the free workshop so you can get legally protected right now!
3. Get notifiied when each episode of On Your Terms® comes 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

Affiliate marketing can be a great way to earn extra income for sharing things you already use and love—but there’s a legal twist that too many online entrepreneurs are overlooking. Whether you’re a coach, creator, or content-loving business owner, you need to know how to share affiliate links and sponsored content without landing yourself in hot water.

This episode is your crash course in the actual legal rules you’ve probably never been taught about affiliate disclosures—and the mistakes that have already led to lawsuits against influencers (even if they thought they were doing it right).

So if you’ve ever wondered, “Wait, am I allowed to post this?”—tune in! Because I’m sharing exactly what the law says and how to stay protected while creating a new revenue stream.

In this episode, you’ll hear…

1. Why affiliate marketing and sponsored content are NOT the Wild West anymore
2. What the recent Alo Yoga and Revolve lawsuits mean for creators like you
3. The one legal mistake that most creators are making—and how to fix it
4. What “material connection” means (yes, even free stuff counts!)
5. How to properly disclose affiliate links in newsletters, videos, and stories
6. Why a tiny “#ad” buried at the bottom of a post won’t cut it
7. What the FTC says about international creators targeting US audiences
8. Sam’s simple “obvious + hard to miss” formula for disclosures that keep you compliant

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

RESOURCES:

1. Sign up for my free weekly email Sam’s Sidebar
2. Order my book, When I Start My Business, I’ll Be Happy: A Practical No-BS Guide to Successful Online Entrepreneurship
3. Click here to watch the free workshop so you can get legally protected right now!
4. Get notifiied when each episode of On Your Terms® comes 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

What if your content didn’t just get attention—but actually got results?

I’m sharing the turning point that made me ditch the high-speed hamster wheel of content creation and finally start marketing in a way that works for me. Spoiler: It didn’t involve more posts, reels, or dancing (thank goodness).

After a moment with my dad during his chemo treatment made me reevaluate how I was spending my time (and what really mattered), I knew there had to be a better way to grow a business than relying on 24-hour stories and random dopamine hits. And there is.

In this episode, you’ll hear…

1. Why I traded dopamine marketing for deeper connections
2. What “depth content” really means (no crying on camera necessary)
3. How evergreen + searchable content becomes your biz’s best investment
4. What the “Big 3” strategy is and how to use it to grow your audience and revenue
5. The one mindset shift that helped me stop scrambling and start selling sustainably

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

RESOURCES:

1. Sign up for my free weekly email Sam’s Sidebar
2. Order my book, When I Start My Business, I’ll Be Happy: A Practical No-BS Guide to Successful Online Entrepreneurship
3. Get notifiied when each episode of On Your Terms® comes 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

What if your next big launch didn’t feel like sprinting a marathon in heels? What if, instead, it felt calm, strategic, and (dare I say it?) kind of fun?

In this episode, I’m pulling back the curtain on how I orchestrated a $338,000 launch for the Ultimate Bundle® in just four days—without burning out or sacrificing my sanity. I’m breaking down exactly why this launch was so successful, what mindset shifts made the biggest difference, and how you can start building toward your own peaceful and powerful launch, too.

In this episode, you’ll hear…

1. Why being “chill” about your launch might be the secret to your biggest revenue yet
2. How detaching your self-worth from your income can unlock better results
3. The 4 surprising ingredients that made this launch feel so… easy
4. How one webinar (and a killer replay strategy) drove massive conversions
5. What I stopped doing during launches that actually helped me sell more
6. The strategic shift that took our webinar conversion rate from great to bonkers (think: 11%!)

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

RESOURCES:

1. Sign up for my free weekly email Sam’s Sidebar
2. Read From Sign-Up to Show-Up: Launch Success Tips on Substack
3. Order my book, When I Start My Business, I’ll Be Happy: A Practical No-BS Guide to Successful Online Entrepreneurship
4. Get notifiied when each episode of On Your Terms® comes 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

I’ve been a little quiet here on On Your Terms—but for good reason. In this quick update, I’m sharing where I’ve been (hint: launching a book!) and what’s coming next (some juicy behind-the-scenes lessons I’ve learned after 2 super successful launches so far in 2025). If you think that online business is dying or you’re wondering whether it’s true that things are changing, next week’s episode is definitely for you. Can’t wait to be back in your ears this Monday, May 12.

RESOURCES:

• Order my book, When I Start My Business, I’ll Be Happy: A Practical No-BS Guide to Successful Online Entrepreneurship
• Sign up for my emails Sam's Sidebar

CONNECT:

• Sam on Instagram
• Sam on Facebook
• On Your Terms® on Instagram
• Sam on YouTube
• Sam on Substack

DISCLAIMER

What do you do when a dream podcast opportunity comes knocking… and the universe throws every travel disaster at you to stop it?

In this week’s episode of On Your Terms®, I’m sharing the behind-the-scenes (and in-the-air) chaos that nearly kept me from being interviewed by Nathan Barry on the Nathan Barry Show. From flight fiascos and airport sprints to finally stepping inside Kit's new Chicago studio—this episode is part travel diary, part entrepreneur pep talk.

If you’ve ever wondered what it’s like to do press while launching a book, or just love a good behind-the-scenes adventure with a few marketing and mindset nuggets sprinkled in, this one’s for you.

In this episode, you’ll hear…

1. The wild travel journey that almost made me miss my biggest podcast interview yet
2. What it’s like inside Kit’s brand-new Chicago studio (it’s next-level!)
3. How I stay productive and grounded even when things go off the rails
4. My thoughts on what top-tier podcast producers do differently—and what we can learn from them
5. A sneak peek at how I’m marketing my new book and building an audience beyond social media

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

RESOURCES:

1. Order my book, When I Start My Business, I’ll Be Happy: A Practical No-BS Guide to Successful Online Entrepreneurship
2. Watch this episode on YouTube
3. Check out my episode with Nathan on the Nathan Barry Show
4. Get notifiied when each episode of On Your Terms® comes 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