On this episode of the Stuck In My Mind Podcast, host Wize El Jefe sits down for an inspiring and candid conversation with Kym Insana, the dynamic founder of Always On Digital. Kym is living proof that you can build a multi-million dollar business, work with some of the biggest brands in America, AND still make it home for bedtime stories and soccer games. In this heartfelt episode, she opens up about her unconventional journey from a high-stress corporate grind in New York City to creating a thriving digital marketing agency built on freedom, flexibility, and genuine connection.
The episode kicks off with Kym reflecting on a pivotal moment when her young son's daycare journal made her rethink her priorities. She shares how her family’s needs—and especially her desire to be present as a mom—inspired her to quit her long commute, leave her corporate job, and go all-in on entrepreneurship. Kym’s raw honesty will resonate with anyone who’s ever felt the pull between career ambition and family life.
Wize guides Kym through her bold transition from corporate leader to business owner, diving into the mental shifts required to move from employee to entrepreneur. Kym talks about her learning curve, from sales to mastering the less glamorous (and often overlooked) aspects of running a business: payroll, insurance, accounting, legal rules, and, most importantly, looking out for her team as she would her own kids.
A significant theme in this episode is how Kym structured Always On Digital around her family’s schedule, creating boundaries that work for both her and her clients. She reveals how honesty and transparency—about things like not taking calls during the 3-5pm “mom window”—built not just a business, but a loyal clientele that appreciates real work-life balance. For listeners wondering if that kind of balance is possible, Kym’s practical advice and lived experience offer real hope.
Wize digs into some of Kym’s growth strategies, from her proven five-step framework for product sales to her philosophy that “the foundation” is the most skipped step for small businesses. She expands on digital marketing myths, strategic platform selection (hint: you don’t have to be everywhere!), and why so many entrepreneurs get distracted by shiny new tools instead of focusing on what works for their actual audience and budget.
Kym spells out the biggest mistakes she sees in digital marketing, including overspending before you’ve exhausted the free and organic opportunities—think, posting consistently and using AI tools like ChatGPT to spark creativity. She emphasizes the importance of cost transparency, knowing exactly where your ad dollars are going, and understanding when it makes sense to shift to paid ads.
An especially powerful section centers on building relationships: whether it’s developing an engaged email list or leading a team of powerhouse moms, Kym shares why loyalty, community, and authenticity always win over flashy metrics or mass production. Her insights into retaining talent and delivering quality service are invaluable for business owners tired of organizational churn and cold company culture.
Throughout the conversation, Kym and Wize keep it real about the highs and lows of juggling work and parenthood. They both share hilarious anecdotes—like kids and grandkids unintentionally crashing live calls—to highlight the beauty in the chaos and the blurry lines we all navigate in the remote work world. There’s wisdom, laughter, and some well-earned humility about days that don’t look as perfect as the Zoom frame suggests.
On the future of digital marketing, Kym forecasts a surge in AI-powered tools but predicts a renewed hunger for the “human touch.” She explores the fast rise of live shopping and how brands need to create authentic, interactive experiences to engage audiences. As technology brings instant gratification closer to home, she stresses the enduring value of genuine, person-to-person service and creative content.
For entrepreneurs hungry to scale sustainably, Kym drops some hard truths about understanding your finances, embracing flexibility, and not falling in love with any one idea (shoutout to Jay-Z’s business advice). She urges listeners to be open to pivots, get foundational accounting skills, and remember that long-term peace and happiness trump empty hustle.
The episode wraps with Kym’s encouragement to anyone on the fence about starting a business: you don’t have to wait for the “perfect” moment. Take small steps, try things part-time, and remember—you can always go back to a job, but you’ll never know what’s possible if you don’t bet on yourself.
If you’re a parent, entrepreneur, creative, or just someone tired of being told you can’t have both ambition and a life, this episode is for you. Kym Insana proves you can scale with soul, and that real success comes from showing up fully—at work, at home, and for yourself.
Connect with Kym Insana:
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LinkedIn: Kym Insana
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Website: getalwayson.com
Highlights:
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The reality of switching from corporate to entrepreneurship
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Mastering work-life balance as a parent and CEO
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Building a business model and team around real family needs
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Small business digital marketing strategies that actually work
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How to avoid wasted ad spend and pick platforms that make sense
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The growing importance of authenticity and the “human touch” in digital marketing’s AI age
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Real stories, laughs, and advice for finding peace and building what matters
Tune in and get unstuck—it’s time to build your business AND your life, on your own terms.
