Your Next Business Bestie

A baby, a teenager, and $76,000. A lot has happened since the last episode of Your Next Business Bestie. I’m back after a year away, catching you up on becoming a mom of three, running my business through it all, and planning a move back to Maine. We went from a family of three to five in a matter of weeks, and my workdays look very different now. I’m also sharing what it feels like to finally pay off the $76,000 in credit card debt I carried from a past relationship—and why celebrating that comes with more complicated feelings than I expected. We’re talking about freedom, exhaustion, financial scarcity, and learning to give ourselves credit for what we’ve done. If you’ve been moving straight from one responsibility to the next, I hope this episode gives you a reason to pause and celebrate something in your own life. Your Next Business Bestie returns with new episodes every other week-ish, because life. Expect conversations with business owners about the stories that shaped them, plus solo episodes as I navigate this chapter. Have a story to share or someone you’d love to hear on the show? Reach out at [email protected] or visit jennsway.com.

Ellie Steinbrink on Authentic Style, Visibility, and Pricing Your Worth This week on Your Next Business Bestie, I’m joined by personal stylist, brand coach, speaker, and new podcast host Ellie Steinbrink. After two decades in marketing and branding, a pandemic layoff pushed Ellie to follow a lifelong passion for style. Today she helps ambitious women align the inside work with the outside look so they can show up with confidence and be seen. We dig into: - Why style is an inside-out transformation, not just shopping - The scary leap from corporate to entrepreneurship and how to know you’re ready - Authenticity as a business growth lever - Pricing your services when your experience lets you move faster than “hourly” can measure Ellie also shares her new show The Visibility Shift, plus a free guide, Style Mindset Reset, and details on The Visibility Edit, her 8-week group program. Listen in for practical mindset shifts, client stories, and permission to show up as the boldest version of you.

What happens when you follow your nervous system—not your to-do list? In this heart-opening episode of Your Next Business Bestie, Jordan shares her journey from burnout in tech to building a multi-passionate wellness business rooted in yoga, fertility awareness, and Costa Rican sunshine. We talk about the spiritual side of yoga, the surprising challenges of yin, and how fertility education changed both our lives in ways we never expected. We also dive into the realities of starting over, building peace on your own terms, and living a life aligned with your values—one that actually feels good in your body.

After facing a life-changing cancer diagnosis, Diane Simard realized survivorship didn’t come with a script that fit. So she wrote her own. In this episode of Your Next Business Bestie, Diane shares her journey as a Stage III breast cancer survivor, business executive, author, and unapologetic disruptor of the pink ribbon narrative. We talk about the emotional side of survivorship that often gets overlooked, the power of being misunderstood, and how Diane found healing through writing, advocacy, and boldly sharing her truth. She opens up about founding the Center for Oncology Psychology Excellence (COPE), navigating grief, and why she’s so committed to speaking up for the ones who can’t. If you’ve ever felt boxed in by labels or like your story doesn’t match what people expect, this one’s for you.

This week on Your Next Business Bestie, I’m joined by Michelle Hoglan, founder of Top Hat Creative Marketing and my trusted expert on Google Business Profiles. Michelle and I explore her journey from the corporate world and gifted education to co-running a boutique digital marketing agency that empowers small businesses—particularly healthcare providers and service professionals—to master Google reviews, profile optimization, and captivating presence online. In our chat, Michelle uncovers: - Hidden features of your Google Business Profile (spoiler: it’s more than just your hours and phone number) - Practical strategies for handling reviews—good, bad, or bogus - Smart tips like using events, backlinks, and dynamic QR codes to boost visibility - Their newer offerings: dynamic video reviews and targeted digital ad campaigns We also get personal about navigating entrepreneurship amid health challenges, the freedom of work flexibility, and why showing up—even when it’s uncomfortable—makes all the difference. Expect laughs, real talk, and actionable takeaways. If you’ve ever wondered how to make your Google Business Profile work smarter (not harder), this episode delivers clarity, confidence, and practical steps to help you shine online.

Season 2 is here, and we’re kicking things off with a deeply personal episode. I’m pulling back the curtain on what it’s really like to be a business owner while navigating pregnancy for the first time. From unexpected pivots to shifting work rhythms, I’m sharing the raw, the real, and the ridiculously exhausting parts of this season of life. We are talking about boundaries, transparency, the comments people really need to stop saying to pregnant humans, and the power of showing up authentically, even when life throws you a major curveball. Whether you have been here, you are in it now, or you are just curious about how we can build businesses that flex with our lives, this one is for you. Let’s kick off Season 2 together. I am so glad you are here.

This week on Your Next Business Bestie, I’m joined by the incredible Hanna Finissi—life coach, retreat host, breathwork facilitator, and founder of Soul Trust Ignite. Hanna’s story is a powerful reminder that our path doesn’t have to make sense right away to be meaningful in the long run. We talk about her journey from teaching middle school math with Teach for America to hosting transformational retreats and launching her new membership, The Athletic Soul Collective. Hanna shares how her experience as a Division I athlete helped shape her approach to personal growth, blending structure, self-trust, and embodiment. We also explore the magic of breathwork—what it is, how it works, and why it’s become a core part of her work. (I share a little about my own breathwork experiences too.) If you’ve ever felt pulled toward deeper self-discovery or wanted a more grounded, guided way to show up for yourself, Hanna’s membership might be exactly what you’re looking for. Tune in for honest conversation about self-evolution, entrepreneurship, building aligned community, and creating a business that grows with you. Connect with Jenn: [email protected] www.jennsway.com www.instagram.com/lifejennsway Connect with Hanna: [email protected] https://www.soultrustignite.com/ https://www.instagram.com/soultrustignite/

In this week’s episode of Your Next Business Bestie, I sat down with my friend Margie Thirlby DuBois, a confidence coach and leadership consultant. We talked about how we first connected during a really hard time in my life, right after I lost my soul cat Jack — and how Margie showed up with so much grace and kindness. Margie shared her journey from nonprofit leadership to launching her own business in March 2020. Today, she focuses on coaching, retreat facilitation, and leadership training, helping individuals and teams build confidence, have brave conversations, and create more human-centered workplaces. We also talked about her recent viral LinkedIn post about workplace bullying, how scary it was to share, and how powerful it’s been to help others feel seen. Margie’s fire as an entrepreneur comes from watching people realize their own potential — and it’s clear she’s making a big impact. If you want to connect with her, you can find her at ThirlbyCo.com, on Instagram (@coachmargie), or on LinkedIn (Margie Thirlby DuBois). Thanks for listening, and I'll see you next time on Your Next Business Bestie! Connect with Jenn: www.jennsway.com www.instagram.com/lifejennsway [email protected] Contact Margie: www.instagram.com/coachmargie https://www.linkedin.com/in/margiedubois/ www.thirlbyco.com

This week, I’m doing something totally new—my first episode with two guests at once! I’m joined by longtime friends and brilliant creatives Krystina Fisher (The Messy Cookie) and Lauren Lear (Lauren Lear Photography) to talk about their sweet (literally) collaboration: Sweet Selfie Photo Booth, a unique event experience that prints photo booth pictures directly onto cookies. We get into the origin of their partnership—from networking, to sharing studio space, to launching a business together. We talk about the highs, the “bucket conversations,” and the behind-the-scenes of building a photo booth-cookie-printing business that’s part art, part entertainment, and all magic. You’ll also hear what it’s really like going into business with your best friend—and how communication, trust, and knowing your strengths make all the difference. If you’re a creative, an entrepreneur, or just love a story about friendship, food, and badass business-building—you’ll love this one.

This week on Your Next Business Bestie, I’m catching up with someone so special to me—my friend Amanda from The Bold Alchemist Creative Studio. Amanda and I used to see each other weekly when she lived in Colorado, and recording this episode felt like coming home. She’s a branding and web designer who brings a beautiful blend of soulful energy readings and design magic to help holistic, women-led businesses thrive. In this episode, Amanda shares how she took a leap of faith in 2024 to start her business after leaving the corporate world. We dive deep into what it’s like to combine multiple passions into one cohesive brand, the challenges of showing up authentically, and how things like Human Design, astrology, and numerology influence her work with clients. We also chat about the importance of community, how our businesses evolve alongside us, and the magic of being truly seen in business—especially as a reflector like me. Amanda even pulls a special tarot card for listeners in honor of the Spring Equinox (spoiler alert: it’s a beautiful one). If you're a multi-passionate entrepreneur trying to figure out how to bring all of you into your business—or you’re just craving a deep, soul-led convo—you don’t want to miss this one. Connect with Amanda on Instagram: @theboldalchemist Connect with Jenn: [email protected] @lifejennsway www.jennsway.com