When I Start My Business, I’ll Be Happy (And Other Lies We Tell Ourselves) with Sam Vander Wielen
The #PrettyAwkward Entrepreneur Podcast
Release Date: 04/14/2025
How I Had a $42K Sales Day While Not in Launch and Rebuilding My Business With Babies
The #PrettyAwkward Entrepreneur Podcast
In this episode, I’m sharing the full story behind one of my biggest revenue weeks in this new season of business: $42,000 in sales, including a $20K cash day, all while working part-time hours and raising twins (and NOT in the middle of a launch). This wasn’t a one-time fluke. It’s the result of building a brand with a clear edge, focusing on what actually drives sales, and letting go of outdated strategies that no longer serve the version of me (or my business) today. Inside, I get into: How I brought in high-ticket sales without working around the clock Why reinventing my...
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From 9–5 to 60K Followers: Laura Banks on Ditching Employee Energy & Building a Standout Health Brand
The #PrettyAwkward Entrepreneur Podcast
What does it really take to go from feeling stuck at an income plateau…to running events, selling out launches, and becoming the go-to name in your niche? In this episode, I’m joined by one of my incredible private clients, Laura Banks, a nutrition health coach who’s gone from stalled growth to full-on CEO momentum (midday walks and all 🙌). We talk about: ✨ The mindset shift that changed everything in her business 📈 How she grew her Instagram to almost 60,000 followers with signature content 💌 Why her consistency with email (hello, 5K+ subscribers!) is fueling her best...
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When I Start My Business, I’ll Be Happy (And Other Lies We Tell Ourselves) with Sam Vander Wielen
The #PrettyAwkward Entrepreneur Podcast
If you've ever caught yourself thinking, "When I hit that next milestone, then I’ll finally feel successful", this episode is a must-listen. This week, I sat down with Sam Vander Wielen, attorney-turned-entrepreneur, legal educator to over 350,000 online business owners, and author of the powerful new book When I Start My Business, I’ll Be Happy. Sam built a multi 7-figure business helping entrepreneurs legally protect themselves, while navigating the unimaginable: the back-to-back loss of both of her parents, a major surgery, and becoming a caretaker...all while launching and growing her...
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No Big Transformation? No Problem. Here’s How to Tell Your Story Anyway
The #PrettyAwkward Entrepreneur Podcast
What if you never hit rock bottom? Never had a dramatic "I was broke, burned out, and living in my car" moment? And yet… you're still really damn good at what you do. This episode is for the entrepreneurs who didn’t rise from the ashes, but still want to share a compelling story that connects. Today, I’m breaking down how to craft a magnetic business origin story when you don’t have a huge transformation moment, and why you don’t need one to be memorable, inspiring, or profitable. Whether you were profitable from Day One, came from a corporate background, or simply “fell into”...
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What No One Tells You About Success and Constant Overthinking with 7 Fig Entrepreneur Ashley Krooks
The #PrettyAwkward Entrepreneur Podcast
You’ve hit the goals, built the business, and checked all the boxes of success… so why does it still feel like something’s missing? Or maybe you haven’t hit the goals yet—because overthinking, self-doubt, and mental spiraling keep you stuck in inaction, second-guessing every move. In this episode, I’m joined by 7-figure entrepreneur and creator of The Reset Room, Ashley Krooks, who shares the raw truth behind success, burnout, and the thought spirals that high achievers know all too well. Ashley opens up about how she went from living her “dream life”—traveling the world,...
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The Strategy Behind Mary’s Largest Launch & Big Speaker Opportunity
The #PrettyAwkward Entrepreneur Podcast
🚀 What if your coaching business could replace your full-time income—without working 24/7? That’s exactly what my client is on track to do by June and in today’s episode, we’re pulling back the curtain on the strategy, mindset shifts, and behind-the-scenes coaching that made it happen. Within four months of coaching she’s matched her healthcare income for two months in a row, had her biggest launch yet, and (just casually 🤯) got accepted to speak at a huge event in Las Vegas this fall. But here’s the thing—this didn’t happen by accident. In this episode, we break down:...
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Motherhood & Business: The Identity Shift No One Talks About with Jess Glazer (+ Must-Know 2025 Social Media Tips!)
The #PrettyAwkward Entrepreneur Podcast
Becoming a mom completely rocked my sense of self. One minute I was running my business, hitting big numbers, sooo focused on the next goal, the next level, the next “thing”, then all of a sudden I’m a mom and completely obsessed with my babies, almost forgetting the life I had prior. The journey back to business and balancing the two has not been easy, and the same goes for today’s incredible guest, one of my mentors, Jess Glazer. We dive deep into the identity shift that happens when you’re both a new mom and a business owner—how it shakes your confidence, changes...
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🎙️ The Confidence Shift That Landed My Client a Speaking Gig, Viral Growth & More Clients
The #PrettyAwkward Entrepreneur Podcast
Ever feel like you’re doing all the things—posting, engaging, tweaking your offer—but still not seeing the momentum you want? That was my client just a few months ago. Fast forward four months, and she’s now: ✅ Landed a huge speaking gig ✅ Went viral (hello, massive visibility!) ✅ Signed two dream 1-1 clients in the last week ✅ Had her best launch yet in Feb So, what changed? Her confidence. But not just the “rah-rah motivational” kind—the deep, unshakable belief in her expertise that made her an obvious choice for her ideal clients. In this episode, I’m...
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(EXPERT INTERVIEW) Are You Anxiously Attached To Your Business? Sami Cleaver Tells All
The #PrettyAwkward Entrepreneur Podcast
Buckle up baby, because this episode is going to rock you in the best way possible. If you are constantly refreshing your phone, always checking your DM’s, looking to see if a client needs you even when it’s past your allotted hours, you’ll want to listen to this episode because you might be anxiously attached to your business. In this episode Sami, our expert for the week, shares how to spot the signs you’re anxiously attached in your business and how to work through it. She also explains how being activated in relationships can really affect how...
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The Power of Personal Touch: Turning Hesitant Leads into Paying Clients in 2025
The #PrettyAwkward Entrepreneur Podcast
Have you noticed your potential clients are more cautious than ever about investing in coaching or programs? You're not alone. In 2025, people are craving connection, reassurance, and proof that you can truly help them before making a decision. Buyers are SMART, savvy and have been burned a time or two, so they want to make sure they’re spending their money wisely, which means we need to add back in that personal touch energy to walk them through step by step how our program can help them. In this episode, I share a simple yet powerful strategy that transformed two "I can't right now"...
info_outlineIf you've ever caught yourself thinking, "When I hit that next milestone, then I’ll finally feel successful", this episode is a must-listen.
This week, I sat down with Sam Vander Wielen, attorney-turned-entrepreneur, legal educator to over 350,000 online business owners, and author of the powerful new book When I Start My Business, I’ll Be Happy.
Sam built a multi 7-figure business helping entrepreneurs legally protect themselves, while navigating the unimaginable: the back-to-back loss of both of her parents, a major surgery, and becoming a caretaker...all while launching and growing her business.
We talk about:
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How she grew an email list of 46,000+ subscribers (even in a “less exciting” niche like legal!)
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Turning everyday moments into compelling marketing stories that connect, convert, and keep your audience engaged
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Why chasing milestones doesn’t bring happiness, and what actually does
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What resilience really looks like when your personal life feels like it’s falling apart
This episode is raw, honest, and wildly inspiring. Whether you're in a season of hustle, heartbreak, or both, you’ll walk away with permission to be human and keep showing up.
About Sam Vander Wielen:
Sam Vander Wielen is an attorney-turned-entrepreneur and the go-to legal educator for online business owners. As the founder of Sam Vander Wielen LLC, she created the internet’s most trusted contract template shop, generating multi-seven-figure revenue annually. She’s the author of When I Start My Business, I’ll Be Happy and host of the On Your Terms® podcast, where she dishes out no-fluff legal tips, honest marketing strategies, and practical business advice. Since 2017, she’s helped over 350,000 entrepreneurs grow legally and confidently—while navigating profound personal loss and life-altering challenges.
Sam’s Links:
→Get Your Book & Bonuses Here: https://samvanderwielen.com/book/
→Follow Sam on Instagram: https://www.instagram.com/samvanderwielen/
→Get Sam’s SideBar Newsletter: https://www.samvanderwielen.com/easy-emails/
Meg’s Links:
→I have ONE 1-1 coaching spot open. DM me “COACHING” on Instagram to apply: https://www.instagram.com/meganyelaney/
→Join my private podcast, MomLife Unfiltered: Business in the Balance: https://meganyelaney.com/private-podcast
→Craft Your Business Origin Story with the Business Story Blue Print: www.meganyelaney.com/business-story-blueprint