In this powerful and emotionally rich episode of High, Low, and Unexpected, Shaun Gordon talks with Taylor Petrinovich—wedding filmmaker, educator, and co-founder of The Level Up Co.—about the rollercoaster journey of building a dream business while navigating motherhood, betrayal, and personal loss.

Taylor opens up about how her entrepreneurial spark was ignited after the tragic loss of her father, how fear and grief fueled her first (failed) business, and how that “failure” taught her to try again. She shares candidly about what it means to trust (and be betrayed), how she turned loneliness into partnership, and why niching down in business has brought the greatest growth.

Topics Covered:

• Grieving the sudden loss of her dad and how it launched her entrepreneurial journey
• What she learned from her failed candle business—and why she doesn’t regret it
• The birth and explosive growth of The Level Up Co.
• Finding the right business partner and pivoting from solo to shared success
• Coping with betrayal from a mentor and the emotional fallout
• Lessons on trust, boundaries, and building from a place of healing
• Her Enneagram 3w4 wiring and how it plays into business, leadership, and relationships

Taylor’s story is a testament to grit, courage, and the belief that dreams—even the scary ones—are worth chasing.

In this deeply vulnerable and relatable episode of High, Low, and Unexpected, Shaun Gordon sits down with Kelley Gilster—wedding filmmaker, serial entrepreneur, and co-founder of The Level Up Co.—to talk about the emotional cost of success, rediscovering purpose after burnout, and building a business that supports your real life, not just your goals.

Together, they unpack Kelley’s journey through motherhood, running four businesses, hitting her financial peak in 2024 while feeling at her lowest emotionally, and the wake-up call that brought her back to herself. Shaun also reflects on his own recent retreat experience and shares how emotions, the Enneagram, and a deeper awareness are shifting the way he shows up as a leader.

Key Topics Covered:

• The myth of “having it all together” and what happens when you don’t
• Kelley’s unexpected path into motherhood and entrepreneurship
• The emotional weight of 2024—and why success felt empty
• Building Level Up Co. and the power of aligned partnerships
• Enneagram Type 3w2 and how it shaped Kelley’s mindset
• The power of awareness, therapy, and showing up as your whole self

This is a must-listen for anyone juggling ambition and real life, and anyone who’s ever felt like their achievements weren’t enough. You’ll walk away challenged, inspired, and seen.

In this episode, Shaun chats with Jon Hayes, founder of a brand photography company and educator for aspiring photographers, about the unexpected pivot towards rest and fulfillment in both life and business. Jon shares his journey from an achiever mindset to embracing a new pace of life—learning how to prioritize family, rest, and intentional living over the constant hustle. He talks about his career highs, his struggles with ambition, and the most difficult lesson he’s learned in balancing productivity and personal fulfillment.

This episode covers:

• Jon’s journey from corporate to entrepreneur

• The unexpected wisdom of slowing down

• Why achieving success doesn’t always bring fulfillment

• How Jon and his family have found balance in Florida

• The importance of setting a new pace for a meaningful life

Tune in for an inspiring conversation about redefining success and learning to embrace rest.

In this episode, Shaun sits down with Joe Paulicivic III, a former wedding photographer who left the hustle behind to find true purpose through vulnerability and connection. Joe shares his journey from building a successful career to letting go of everything, including his studio, and embracing a life on the road. He talks about his time photographing homeless youth in New Orleans, how this unexpected project transformed his life, and how he has learned to heal through connection, curiosity, and compassion. Joe’s story is a powerful reminder of the value of slowing down and listening to what life presents.

This episode covers:

• Joe's journey from successful photographer to questioning his career and life choices

• How he ended up photographing homeless youth in New Orleans and the unexpected project that emerged

• The importance of vulnerability, human connection, and compassion in both personal and professional life

• How Joe's shift in priorities led to a life-changing experience with the "dirty kids"

• The unexpected blessings that come from stepping away from ego-driven pursuits

Tune in for a heartwarming conversation about overcoming adversity, embracing stillness, and how we can all learn to be more present and compassionate in our own lives.

In this episode of High Low and Unexpected, Shaun connects with Angela, an inspiring entrepreneur who transitioned from a wedding photographer to running a successful business creating social media templates. Together, they discuss Angela’s journey through burnout, entrepreneurship, and the emotional highs and lows of owning a business. Angela opens up about the challenges of balancing motherhood, career, and self-expectations, sharing how a pivotal moment of rejection led to a business pivot that changed everything. A must-listen for anyone navigating the unpredictable world of entrepreneurship.

In this episode, Shaun chats with Wyatt Ewing, the founder and CEO of Ice Barrel, about how adversity and personal struggles led to the creation of a company that is now helping thousands improve their health and mental well-being. Wyatt shares his story of growing up with immense challenges, dealing with anxiety, and the turning point that led him to create Ice Barrel—a tool that promotes physical and mental healing through cold exposure. From overcoming personal lows to building a thriving business, Wyatt's journey is a testament to the power of resilience and the importance of pursuing what truly matters.

This episode covers:

• Wyatt’s journey from childhood struggles to corporate success and beyond

• The pivotal moment that led him to discover the power of cold exposure

• How Ice Barrel helps people with chronic pain, anxiety, and stress

• The unexpected mentor who helped him grow his business

• The importance of being present in life and in business

Tune in for an inspiring conversation about overcoming adversity, finding peace, and the unexpected blessings of entrepreneurship.

In this episode, Shaun sits down with Chelsea Allegra, a portrait photographer and business owner, to discuss the balance of entrepreneurship, motherhood, and setting boundaries to stay aligned with what truly matters. Chelsea shares her journey from wedding photography to portrait photography, and how she successfully transitioned to a business model that prioritizes family life without compromising on financial success. She opens up about the pressure to hustle, the challenge of setting boundaries, and the importance of doing what feels right for you—even if it’s not the popular choice.

This episode covers:

• Chelsea’s transition from wedding photography to portrait-only photography

• How she found alignment with her business and personal life

• The importance of setting boundaries and saying no to opportunities that don’t serve your vision

• Navigating the highs and lows of entrepreneurship, especially as a mom

• Overcoming the fear and pressure of doing things differently

If you’re looking for insight on creating a fulfilling, balanced business, this episode is a must-listen.

Managing your taxes as a photographer doesn’t have to be overwhelming. In this episode, Shaun sits down with Heather Leicy, a photographer, educator, and the creator of Make Taxes Suck Less: A Beginner Photographer's Guide to Taxes. Heather shares her journey from architecture to full-time photography, her struggles with work-life balance, and how she unexpectedly became a go-to resource for creatives navigating taxes.

This episode explores:

📸 The reality of going full-time as a photographer

💰 The biggest tax mistakes photographers make (and how to avoid them)

⏳ How to set up simple tax systems to save time & stress

📊 Why every photographer should track their numbers before tax season hits

👩‍🏫 The inspiration behind Heather’s Make Taxes Suck Less course for photographers

👉 And here’s the best part: If tax season gives you anxiety, Heather is giving our audience 20% OFF her Make Taxes Suck Less course!  Use code “KISS20” for 20% off the go-to guide for photographers who want to keep more of their hard-earned money and actually feel confident about taxes. Seriously it is a GAME CHANGER!

In this episode, Shaun is joined by Sean Finnegan, an entrepreneur who’s navigated the highs and lows of building a business from the ground up. From raising $1.5 million with nothing but a spreadsheet and a dream, to facing a massive financial crisis, Sean shares his rollercoaster journey of entrepreneurship. He reveals how relationships, persistence, and failure played crucial roles in his success and what it takes to bounce back after hitting rock bottom.

This episode covers:

• The thrill of hitting highs and the gut-wrenching lows of entrepreneurship

• Raising $1.5 million and losing it all—lessons learned the hard way

• How relationships helped Sean pull himself out of the toughest times

• The power of persistence and what it really takes to keep going

If you’ve ever felt like you’re at rock bottom or struggled with the ups and downs of entrepreneurship, this episode will remind you that perseverance and alignment with your values can make all the difference.

In this episode, Shaun chats with his longtime friend, @jameswitty, a destination wedding photographer, about the highs, lows, and unexpected moments in both business and life. James shares his personal journey of how a simple habit change—walking into a CrossFit gym—became the catalyst for transforming not just his physical health, but his approach to marriage, work, and his business. From the highs of celebrating a milestone anniversary with friends to navigating the lows of feeling overwhelmed by success and neglecting other areas of life, James reveals how unexpected moments can sometimes have the most profound impact.

Join them as they dive into the highs and lows of entrepreneurship, the importance of community, and how to lean into the unexpected for personal growth.