This week on High, Low, and Unexpected, Shaun sits down with Southern California artist and TikTok creator Isabella Rosendale—known online as iggybellyy—to talk about the raw energy of starting a creative business from scratch.

Isabella has turned her unique, "funky" artistic style into a thriving brand, recently selling out her first major sticker drop in just 15 minutes.

In this episode, you’ll hear:

• The "Startup Mode" Reality: How Isabella launched her business independently and built the confidence to go from local art fairs to a global online audience.

• Success vs. Fulfillment: A deep dive into the "Missing Balloons" moment—why the true reward of entrepreneurship isn't the applause, but the heart you put into the work.

• Finding Your Creative Voice: Why staying true to your unique, "cartoonish" style is a superpower, and how to stop the trap of comparing your art to others.

• The Heart of Teaching: How Isabella plans to use her platform to mold young minds and help others find their own voice through art.

Isabella’s story is a powerful reminder that we create our best work when we are in total alignment with who we are. Whether you’re a veteran business owner or just starting your journey, this conversation is an essential guide to pursuing passion with integrity.

Isabella’s journey reminds us that success isn’t just something we achieve—it’s something we build day by day by staying true to our own vision.

Whether you’re looking to find your own creative spark, navigate the lonely moments of a startup, or simply be reminded that your unique voice matters—this conversation will meet you there.

Listen now on High, Low, and Unexpected.

🎨 Curious about Isabella’s "funky, fun, and fresh" art or want to grab some stickers from her next drop? Check out IggyBelly.com or follow her journey on TikTok @iggybellyy!

This week on High, Low, and Unexpected, Shaun sits down with wedding photographer, YouTuber, and educator Taylor Jackson to talk about the pursuit of ultimate time freedom. Taylor shares his journey from the 9-to-5 grind to building a scalable creative business that works for him, not the other way around.

In this episode, you’ll hear:

• How to transition from a day job to full-time photography without losing your passion

• Why money management is more important for creatives than buying the next new lens

• How consistent YouTube content leads to trust and partnerships with major brands like Nikon and Leica

• The power of building relationships and a supportive community in the photo industry

Taylor also reveals how his background in computer programming helped him optimize his workflow and why "time" is his most valuable currency. This conversation is an essential guide for any photographer looking to reclaim their time and build a business with intentionality.

📸 Want to learn Taylor’s exact workflow for off-camera flash and business scaling? Check out Taylor Jackson’s Education for Photographers to learn more!

This week on High, Low, and Unexpected, Shaun sits down with Matt Gruber, co-founder of Design Huddle. Based in the beautiful Bend, Oregon, Matt shares a raw and inspiring look at building a global software company while navigating the unique challenges of ADHD and dyslexia.

In this episode, you’ll hear:

• The "White-Label" High: How Matt and his partners "struck oil" by building the B2B version of Canva, serving major entertainment and real estate brands worldwide.

• The Neurodivergent Superpower: Why failing out of high school and being placed in special education didn't stop Matt—it actually fueled his drive to prove the world wrong and innovate.

• The Sleep Deprivation Low: A vulnerable discussion on how a gut health crisis led to severe sleep deprivation, affecting Matt's behavior and business relationships, and the radical 90-degree turn he took to heal.

• The "Unoffendable" Spirit: Matt’s secret weapon for navigating tough business and family dynamics—choosing humility and refusing to take offense, even when things get messy.

Matt’s story is a testament to the fact that our greatest disadvantages can become our greatest strengths if we are willing to "figure it out" and stay present through the struggle.

Listen now on High, Low, and Unexpected.

💻 Ready to see how Matt is revolutionizing design for businesses? Visit DesignHuddle.com or connect with Matt Gruber on LinkedIn!

This week on High, Low, and Unexpected, Shaun sits down with college and sorority photographer Rob Greene to talk about legacy, post-session connection, and what it really looks like to grow a meaningful business.

Rob has built an incredible brand, and last year alone, he brought in $20K+ in album revenue using a simple 15-minute conversation that serves his clients deeply and consistently.

In this episode, you’ll hear:

• How to scale with purpose, not pressure

• The power of follow-up and how it drives connection (and income)

• Why delegation and margin matter more than hustle

• What legacy really looks like as a creative business owner

Rob also shares what inspired him to create his dream home—paid for in full—that now hosts masterminds and photographers from across the country.

This conversation is full of insight, encouragement, and practical wisdom for any photographer who wants to serve better and grow with integrity.

🎓 Curious about how Rob added $20K+ in album revenue last year with a simple workflow? Check out The Album Academy for College & Sorority Photographers to learn more!

This week on High, Low, and Unexpected, Shaun sits down with entrepreneur and coach Nata Salvatori, affectionately known as "The Accidental CEO." Together, they unpack what it means to build a business you love without burning out in the process.

From her early days as a wedding photographer to navigating a career pivot into coaching, Nata shares how her pursuit of excellence led her to a breaking point—and how learning to delegate and ask for help transformed not just her business, but her life.

This episode covers:

• The difference between control and sustainability as a creative entrepreneur

• Why high-functioning burnout is so hard to spot—and what to do about it

• How Nata went from dropping balls to building a team she trusts

• What it really means to run a business that gives you your life back

This episode is a must-listen for anyone who’s ever struggled with letting go, wrestled with guilt, or felt like they had to hold it all together to succeed. Nata brings wisdom, humor, and depth to a conversation every business owner needs to hear.

In this honest and energizing episode, Shaun sits down with his longtime friend and fellow entrepreneur Ben Chernivsky for a conversation that goes far beyond business.

Ben shares what it was like to build a life that looked perfect on paper—successful companies, financial freedom, a beautiful family—and still feel deeply unsettled, until he was able to rebuild from the inside out.

You’ll hear about:

• The surprising emptiness Ben felt after reaching financial goals

• How unspoken loneliness impacted his marriage and mental health

• Why your business often reflects what’s going on internally

• The role of community and mentorship in healing

• Fatherhood, presence, and rewriting your personal legacy

This one’s full of wisdom, reflection, and encouragement for anyone who’s ever asked, “Is this really it?”

In this powerful and vulnerable episode, Shaun sits down with his friend Brit, a photographer and educator who shares her deeply personal story of loss, survival, and the journey of finding identity after a suicide attempt.

Together, they discuss the pressures of entrepreneurship, how creativity and mental health intertwine, and what it means to choose healing in the midst of pain.

This episode is a raw, honest look at what happens when life feels too heavy—and how we can show up for ourselves and each other through it.

This episode covers:

• The quiet struggles behind outward success
  

• Rebuilding identity and purpose after a mental health crisis
  

• The importance of rest, boundaries, and authentic community
  

• Why conversations like these matter in the creative industry
  

Whether you’ve walked a similar road or you love someone who has, this conversation will help you feel less alone—and remind you that your story matters.

⚠️ Trigger Warning: This episode includes open discussion of suicide and mental health struggles. Please take care as you listen.

In this vulnerable and profound episode of High, Low, and Unexpected, Shaun Austin Gordon sits down with his longtime friend and former coach, Julia Woods—a relationship coach known for her powerful in-person event, Breakthrough. Together, they unpack what it means to chase intimacy, embrace the mess, and accept the fact that we never fully “arrive.”

From a tornado that changed the course of her career to the gut-punch realization that healing is lifelong, Julia shares what it really takes to live fully alive—and lead others to do the same.

In this episode, you’ll hear:

• Why couples keep showing up for hard conversations (and how real change happens)

• What Julia learned from her own season of insomnia, grief, and surrender

• How a tornado led to the unexpected start of her second career

• What it means to be a “wounded healer” and walk in your calling anyway

This one is for anyone craving deeper relationships, real growth, and a life that’s led from the heart.

What happens when life pulls the rug out—and you decide to rebuild everything from the ground up?

In this deeply honest episode of High, Low, and Unexpected, Shaun Austin Gordon sits down with destination wedding photographer and creative entrepreneur Roy the Photographer. From a canceled proposal and health issues to a radical shift in work and location, Roy shares what it means to burn down the life you built and start again—with clarity, purpose, and a whole lot of heart.

In this episode, you'll take away:

• How personal and professional burnout sparked a creative “Renaissance”

• What Roy learned after walking away from coaching to return to storytelling through photography

• Why hardship sometimes reveals what truly matters—like connection, health, and faith

• A fresh perspective on rebuilding: how controlled burns can lead to better growth

If you’ve ever been through a season where everything changed, this episode will encourage you to stay honest, stay curious, and keep showing up.

🎧 Listen now and share your favorite takeaway with us!

In this raw and reflective episode of High, Low, and Unexpected, Shaun Austin Gordon sits down with executive coach and leadership advisor Adrian Koehler for an honest conversation about what it really means to show up, both in business and in life. From a pivotal moment on an empty stage to a professional low that cost him trust and opportunity, Adrian shares what it takes to lead with courage, own your missteps, and keep moving forward.

In this episode, you'll hear about:

• What a professional misstep taught him about trust, repair, and leading with humility

• How to confront hard truths in leadership by "riding the elephant" instead of avoiding it

• Why saying yes to an unpaid opportunity led to six figures in unexpected revenue

• What it looks like to build real influence through transparency, not titles

If you're a leader, entrepreneur, or anyone navigating growth, this episode will challenge and encourage you to lead with honesty, humility, and purpose.

Listen now and let us know your favorite takeaway in the comments!