144 episodes

Ready to take that leap of faith and finally chase those dreams of yours? It's not always easy to stay motivated when you're balancing a teaching career, family, and home life, but that's exactly what we're here to help you do. I'm your host, Dori Stewart, and this is the Teacher Turned Entrepreneur Podcast. Around here, we like to talk about our collective and sometimes crazy experiences as entrepreneurs, teachers, and women who do it all. If you've been looking for more in life than grading papers and conferences, this is for you!

I've been called the teacher turned entrepreneur. After spending 11 years in the classroom, I left to start a business that I grew into a multi-million dollar brand. It doesn’t matter where you’re currently at; having someone cheering you on makes a world of difference to get to the head of the class. I love that I can bring that to you here. If you’re ready to build the life you’ve been dreaming of, stay tuned as we dig deep into what it takes to turn teachers into true entrepreneurs!

Teacher Turned Entrepreneur Dori Stewart

    • Business
    • 5.0 • 82 Ratings

Ready to take that leap of faith and finally chase those dreams of yours? It's not always easy to stay motivated when you're balancing a teaching career, family, and home life, but that's exactly what we're here to help you do. I'm your host, Dori Stewart, and this is the Teacher Turned Entrepreneur Podcast. Around here, we like to talk about our collective and sometimes crazy experiences as entrepreneurs, teachers, and women who do it all. If you've been looking for more in life than grading papers and conferences, this is for you!

I've been called the teacher turned entrepreneur. After spending 11 years in the classroom, I left to start a business that I grew into a multi-million dollar brand. It doesn’t matter where you’re currently at; having someone cheering you on makes a world of difference to get to the head of the class. I love that I can bring that to you here. If you’re ready to build the life you’ve been dreaming of, stay tuned as we dig deep into what it takes to turn teachers into true entrepreneurs!

    #144: Leading with the Heart: Transformational Coaching That Starts from Within with Amanda Parker

    #144: Leading with the Heart: Transformational Coaching That Starts from Within with Amanda Parker

    We’ve all scrolled through social media in search of gurus when in fact – as Dori Stewart’s guest on this episode of Teacher Turned Entrepreneur reminds us – a deep knowing and wisdom actually reside within us. It’s just a matter of nurturing it along! Amanda Parker is a speaker, writer and transformational business coach whose heart-centered approach builds leadership vision rooted in her clients’ most authentic selves. She explains how she came to uncover her coaching model and offers tips for anyone looking to cultivate more self-confidence. It starts with trusting our own instincts and uncovering that inner voice! You’ll come away from this episode with actionable steps you can take to start bolstering self-confidence, including an invitation to do the inner work to identify – then weed out – the people and things that are draining rather than life-giving. And if you’re in a New Year’s mood for some goal-setting, then you’ll want to take note of Amanda’s best practices! “It’s not always about setting and hitting a goal, although that can be very attractive and enticing,” she says. “It’s often about how you want to be showing up in the world and factors that will help you get to that place.”

    Stay tuned for Amanda’s upcoming Master Mind course, featuring inspiration from changemakers doing deep work in the world, by visiting this link.

    If you enjoyed this episode of Teacher Turned Entrepreneur, click here to hear past shows and leave comments!


    Here are key takeaways from the conversation:
    • If you’re passionate about something but feeling disconnected, it might be time to explore and figure out.
    • A certain measure of naivete can be helpful when you’re swinging for the bleachers with a new entrepreneurial dream!
    • Career impact starts with uncovering and celebrating your most organic, authentic gifts!
    • Heart-centered leadership is about learning to look within for inspiration and internally generated self-confidence.
    • Compare and despair! Stay focused on and trust your own unique inner wisdom.
    • Self-help gurus and education are great, but over-subscribing can be a signal that you’re getting too far away from your instincts and true north.
    • New Year’s Inventory: Take a moment to visualize who you want to be in the 12 months ahead and really identifying the things that make you feel healthy and grounded in life.


    Here’s a quick look into the episode:
    • Not a Straight Path: Amanda’s pause and decision to hop off the advertising track to go all in on her love of animals and wildlife conservation.
    • Feeling passionate about her work but stuck and disengaged, Amanda set about identifying what drives people to do good work – and love it.
    • Amanda’s entrepreneurship journey started in the leadership space, where she worked with a coach to build programs to support leadership excellence.
    • The Courage Factory grew out of a deep passion for humanizing the workplace and has grown into helping people connect with their dreams and the path to get there.
    • Amanda has more recently shifted away from leadership development to the deeper inner work that enable us to bring our gifts to the world.
    • Tips for Entrepreneurs in Search of Confidence:
    o Do that deep inner work! Get to know who you are apart from external measures.
    o Embrace the values and goals that define you and your entrepreneurial drive.
    o Follow what gives you energy – the things that light you up – and drop what’s draining.
    o Trust yourself and listen to that inner voice.
    o Make the mistakes and move forward!
    • Why it’s important to distinguish between self-improvement and using outside resources to distract from what else might be going on or in need of attention.
    • Goal-Setting for the New Year: It’s all about transformation and giving yourself the space to think about who you’ve become over the past 12 months – and who you wish to be going forward!

    • 19 min
    #143: Order Out of Chaos: How This Mompreneur Helps Create Household Systems! with Heather Steinker

    #143: Order Out of Chaos: How This Mompreneur Helps Create Household Systems! with Heather Steinker

    Putting your family’s Standard Operating Procedures (SOPs) in place may be a little painful at the outset, but the benefits you’ll reap over the long run are undeniable. Productivity Coach Heather Steinker has figured out through trial and error a reliable, replicable roadmap for organizing every aspect of our lives. And with that knowledge comes power! If you can predict it, you can control it. But not without a reliable and comprehensive system, which is where Heather’s online Chaos Control System binder and companion boot camp come into play.

    As this mompreneur has experienced firsthand as a single mother of three, breaking down all the components of life administration can seem pretty overwhelming. But that’s where Heather’s Chaos ‘n Cookies system flexes its muscle, breaking down things like financial planning, household maintenance, children’s needs and even gift-giving history into bite-sized SOPs. The overview brings clarity and peace of mind in knowing that – no matter what curve balls life throws your way – you’ll have a system that’s both nimble and resilient. “It might take some investment in the beginning,” says Heather, “but your mindset and momentum will be much better and more positive (in the long run) if you know everything is in place.”

    • 24 min
    #142: This Young Artist Has Turned Her Whimsical Doodles into a Fast-Growing Business! with Sammy Handler

    #142: This Young Artist Has Turned Her Whimsical Doodles into a Fast-Growing Business! with Sammy Handler

    Sammy Handler is living the dream! She has transformed her passion for art (which started with painting doodles on friends’ shoes in high school) into a growing commercial enterprise. As she explains to Host Dori Stewart on this episode of Teacher Turned Entrepreneur, this 26-year-old dynamo has taken her colorful vision and packaged it in a huge array of ways that have caught the eye of everyone from new moms (who love her bibs and baby blankets) to kids (who devour her personalized accessories) to college students (who are decking out their dorms) to corporate marketers (ever on the prowl for cool new promotional items). Sammy has straightforward advice to offer that will embolden people of all ages to figure out what they love and then work out how to make it “blow up” the way her KicksBySammy custom designs have done. When it comes to scaling her business, we’re learning how this young entrepreneur has gone about identifying collaborators who align with her values and integrated a meaningful charitable element into the model. Sammy has some especially helpful advice for young aspiring entrepreneurs about taking advantage of university resources and building that all-important network! Most of all, you’ll come away inspired to check out Sammy’s art, which is visible not only all over social media but also on eye-catching public murals in Miami and Chicago. Click here if you want a peek at her one-of-a-kind feast for the senses!

    If you enjoyed this episode of Teacher Turned Entrepreneur, click here to hear past shows and leave comments!


    KEY TAKEAWAYS:
    • How Sammy turned her passion for art into a business, from painting shoes for high school friends to blowing up on social media to providing promotional products for large corporations.
    • Expect the Unexpected: Groundbreaking businesses are often built on ideas that no one has ever tried – or thought possible. So go ahead. Explore!
    • The old saying proves true once again: Find something you love doing, then figure out how to make money doing it. The formula works!
    • How did Sammy turn her side hustle into a full-blown enterprise? She got practical about ways to scale her product to connect with the masses.
    • Analysis Paralysis: It’s easy to get bogged down in market research, production systems and planning. Meanwhile, a competitor might be poised to overtake you!
    • Don’t overthink! Your market is always going to evolve and change over time.
    • Sammy’s Biggest Challenge: Juggling the many moving parts involved in running a business from the ground up. She’s the driver behind:
    o Social media
    o Design
    o Finance
    o PR
    • It’s your baby! Sammy is learning (and asking other entrepreneurs about) how to entrust responsibility to others – a necessary next step in her company’s growth.
    • Look for clients and collaborators who:
    o Understand and embrace your work.
    o Share your mission and align with your values.
    o Have a following that meshes well with your own.
    • How Sammy has gone about identifying her collaborators:
    o Networking with others in the art world.
    o Getting her artwork noticed (including public installations).
    • Some of Sammy’s Top-Selling Products are Baby-Centered:
    o Blankets
    o Towels
    o Burp clothes
    o Bibs
    o Pillows
    • Kids and adults alike love the personalization that Sammy offers, which is why she’s constantly researching and open to new ideas for creating bespoke content.
    • The Charitable Element: In tribute to her grandmother, who died of pancreatic cancer, Sammy donates a portion of sales proceeds each year to the Lustgarten Foundation. She also offers a buy-a-gift and give-a-gift campaign that supports holiday toy drives and DIY painting activities live on Instagram.
    • Advice for Young Aspiring Entrepreneurs:
    o Start networking early. It’s so important!
    o Your college has an entrepreneurial center (probably at their business school) so check it out while you can!
    o Start asap to enter contests, pu

    • 17 min
    #141: It’s All In the Voice: This Copywriting Pro Knows How to Capture and Tell the Real Story with Nicole Kepic

    #141: It’s All In the Voice: This Copywriting Pro Knows How to Capture and Tell the Real Story with Nicole Kepic

    Finding your authentic voice is important for any entrepreneur, but especially so when it comes to creating content. And that’s why Nicole Kepic, a popular copywriter who helps coaches and course creators elevate their sales pages, has been able to separate herself from the pack. As a seasoned pro who for years worked in the corporate sector, helping market some of the biggest household brands, she was able to seamlessly convert her side hustle as a freelance content provider into a full-time business. It starts, she tells Host Dori Stewart on this episode of Teacher Turned Entrepreneur, with knowing your client’s goals and defining the message in a catchy, relatable style. “You just have to know your own personality and skill set,” says Nicole, who encourages new writers or those of us with writer’s block to keep it natural. She also recommends ditching the self-judgment and limiting beliefs. You’ll learn some great tips for identifying the audience you want to serve and brainstorming the kind of compelling copy that attracts eyeballs and closes deals – without ever coming off as a hard sell. Is it magic? Nope. Says Nicole: “You can be really friendly and conversational and still be professional and trusted.” Your writing roadmap starts here!

    If you enjoyed this episode of Teacher Turned Entrepreneur, click here to hear past shows and leave comments!


    KEY TAKEAWAYS:
    • That’s just what you did: How Nicole started out as a 9-to-5 copywriter on a traditional corporate path … until what started as a modest side hustle became much more!
    • What if the clients don’t come? How Nicole overcame the initial fears and self-doubt that entrepreneurs commonly experience when first starting out.
    • Defining and differentiating herself has been key to Nicole’s success.
    • Word of Advice: Don’t try to be all things to all people. Scaling down and focusing your offerings will make your portfolio sharper and business easier to manage.
    • The importance of narrowing your offerings, enabling repeatable processes that are time- and sanity-savers.
    • Advice for Entrepreneurs with Writer’s Block:
    o Go easy on yourself. You’re probably better than you think!
    o Keep it natural and write the way you speak.
    o Try to be relatable and conversational with your message.
    • Is writing your superpower? Nicole has tips for wordsmiths looking to start a business:
    o Keep it clean, crisp and clear.
    o Don’t let flowery or clever writing interfere with getting your point across.
    • Getting ready to work with a copywriter? Here’s how to prep:
    o Get clear on your audience, who you’re serving and the service you wish to provide.
    o Define the message you want to communicate so it doesn’t get watered down or lost in translation.
    • How she stands out: Nicole’s long experience with well-known brands is a big asset, but it’s her friendly, approachable writing style that truly distinguishes her from the pack.
    • Want to retain clients? Make the user experience seamless and enjoyable!
    • Are You An Introvert? Nicole is, and she has surprised herself with a writing style that is light, fun and low-key – but still gets serious sales results!

    • 13 min
    #140: Abundance and Positive Energy Are All Around Us. Are You Ready to Invite Some In? with Jocelyn Kelly Reid

    #140: Abundance and Positive Energy Are All Around Us. Are You Ready to Invite Some In? with Jocelyn Kelly Reid

    Jocelyn Kelly Reid’s coaching methodology brings together abundance and intuitive healing around money – in a unique combo platter that has transformed her clients’ lives! Combining energetics and a deeply feminine sensibility, Dori Stewart’s guest on this episode of Teacher Turned Entrepreneur is sharing the framework she offers women who are ready to allow themselves to receive and grow financially. It all starts, says Jocelyn, with understanding our unique histories and the stories we tell ourselves based on our individual families, financial histories and traumas. Whether your background is one of wealth, poverty or somewhere in-between, Jocelyn is all about working with women who want to transcend life circumstances to make big impact and big money.

    You’ll come away from this episode with a new perspective on the interplay between growth and openness and the ways in which the universe delivers when we practice healthy – and abundant – patterns of thought. Jocelyn shares insights on money’s four energetic areas (and how to work with them) as well as advice for any would-be entrepreneurs who want to be well-prepared before making the leap. Hint: It starts with getting the right support in place! “If you’re not enjoying the process,” says Jocelyn, “you’re not enjoying your life.” So true. Are you ready to step into being Queen? Here’s an invitation to expand your emotional repertoire and invite abundance on every level!

    • 18 min
    #139: This Podcast Content Specialist Has Tips to Boost Your Brand – and Much More! with Leah Stine

    #139: This Podcast Content Specialist Has Tips to Boost Your Brand – and Much More! with Leah Stine

    If necessity is the mother of invention, then chaos might just be a very close cousin. In the midst of raising three young children, juggling home schooling, household priorities and a freelance career Leah Stine decided, “Why not?” and started her own company. If you’ve ever noticed that being super-busy tends to make you more and more efficient, that was definitely the case here! Host Dori Stewart explores the path that Leah took in carving out her niche as a writer specializing in collateral for podcasts and how all the daily juggling and craziness of busy family life somehow always works out. You’ll enjoy hearing about this unique entrepreneur’s journey and just in case home school teacher, mom, spouse, community member and business owner weren’t enough, Leah has recently added author to her resume with the release of her charming children’s book, "A Boy and His Butterfly." Enjoy this fun conversation. It’ll inspire you to follow your passion and think about the many ways that you can repurpose content to market your brand via social media and other channels. For anyone toying with the idea of starting a blog, Leah advises: “Don’t overthink it!’ There’s no better time to start than now!

    If you enjoyed this episode of Teacher Turned Entrepreneur, click here to hear past shows and leave comments!


    Here are key takeaways from the conversation:
    • Not getting the work promised or the conditions advertised? Maybe it’s time to start building your own business on the side!
    • Launching a business in the midst of panic and chaos can be done. Sometimes you just have to dive in!
    • Feeling bored or stagnant? It might be time to refocus and relaunch!
    • If you go to the effort of writing a blog post, remember it can be repackaged in myriad ways for all kinds of social media channels. Don’t leave valuable content on the table!
    • Have you noticed that sometimes the busier you are the more organized you are? It’s a focus thing!

    Here’s a quick look into the episode:
    • Moving from a business degree to the rigors of home schooling, Leah branched out on her own when the marketing work she was doing fell short.
    • How Leah transitioned away from the real estate clients she was serving with social media posts, blogging and newsletters into a focus on her passion for writing.
    • How and why creating her own business has worked better for Leah.
    • Niching Down to Podcasts: The self-development journey Leah took in defining her marketplace and brand.
    • Advice for Podcasters Interested in Creating Blogs:
    o If you want to write a blog, just do it!
    o Make an outline with main bullet points.
    o Don’t overthink it!
    • Ways to Repurpose Blogs:
    o Email marketing.
    o Social media posts.
    o Audiograms, videograms.
    o Infographics.
    o Pull quotes.
    • Every Day is Different: Leah reflects on juggling her business and home schooling, household and other priorities. She embraces her scrambled schedule. It works!

    • 16 min

Customer Reviews

5.0 out of 5
82 Ratings

82 Ratings

Mridu Parikh ,

Awesome podcast!

Dori shares extremely valuable information and experiences from so many female entrepreneurs that will 100% teach you how to grow your business. You’ll be so inspired from hearing stories from these women and get tips along the way. You’ll learn about everything from pitching yourself to mindset to social media. Don’t think about it - subscribe now.

Livemusicluva ,

Inspiring for women business owners

Dori Stewart is a thoughtful host with a mission to elevate and educate women who are exploring the leap into entrepreneurship.

San Diego lady ,

Insightful show. Fun. Lots of nuggets

Dori is so dynamic in her approach and with her guests. I always get a take away nugget from listening to this show on how to better run my business or run my life-sometimes both.

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