High, Low and Unexpected

Shaun Gordon

In this podcast, we explore the remarkable successes, challenges, and unexpected turns that entrepreneurs encounter in their careers.

  1. 1d ago

    Redefining the Threshold: Burnout, Boundaries, and the Power of Enough (ft. Kelsey Converse)

    This week on High, Low, and Unexpected, Shaun sits down with Kelsey Converse, a New Hampshire-based elopement photographer, business coach, and founder of the Biz with Boundaries program. Kelsey is a powerhouse entrepreneur who went from leaving her corporate 9-to-5 to rapidly scaling a six-figure creative brand—but her rapid rise came with a steep learning curve about what it actually costs to "have it all." In this episode, you’ll hear: The "Dream Life Achieved" High: Kelsey celebrates her current reality as a new mom to a six-month-old boy, living the exact balanced life she once envisioned. She shares how years of front-loaded hustle and extreme curiosity about strategic growth allowed her to step away from corporate limitations, travel to 10+ countries a year, and now build a business that fully supports her family timeline. The "Six-Figure Blindspot" Low: A raw look at the deception of vanity metrics. Kelsey opens up about her first massive $100k year in 2021, where comparison-driven hustle led her to book 43 weddings and 15 sessions. Despite the financial win, she describes the breaking point of working from 5:30 AM to 8:00 PM every day, experiencing public breakdowns, and missing her best friends' weddings—forcing her to completely redefine her version of success. The "Superwoman Backlash" Second Low: What happens when you try to fix your capacity problem by aggressively expanding? Kelsey vulnerably shares the heavy reality of 2023: onboarding two associate photographers simultaneously, managing a rental property, launching an education branch, and navigating a heartbreaking pregnancy loss under the weight of chronic cortisol and stress. The "18-Month Astrologer" Unexpected: A funny, perspective-shifting moment where a hometown friend brings an astrologer to a gathering, sparking a conversation about the upcoming transitions that await Kelsey. Shaun and Kelsey unpack the beauty of the unknown, the necessity of personal therapy, and why learning to sit in the neutral "in-between" zones of life is an entrepreneur's greatest asset. Kelsey’s journey is a necessary wake-up call about why we must stop using social media algorithms to measure our self-worth. Whether you are trying to cross the six-figure line or learning how to scale back to protect your peace, this episode will challenge you to look introspectively, get curious about your pain, and determine what "enough" truly looks like for you. Listen now on High, Low, and Unexpected. 🎙️ Want to learn more from Kelsey? Track her journey and find out if that 18-month prophecy comes true by following her on Instagram @kelsconverse or visiting KelseyConverse.com.

    1h 10m

  2. Jun 17

    Miracles in the Mess: Chronic Pain, Sisterhood, and the True Weight of Community (ft. Kelly Lemon)

    This week on High, Low, and Unexpected, Shaun sits down with Kelly, a Seattle-based adventure wedding and elopement photographer. Having survived a catastrophic car accident at age 12 that left a fourth of her body paralyzed, Kelly’s life has been a relentless journey through spinal surgeries, chronic nerve pain, and rehabilitation. Yet, she has transformed her physical constraints into a source of profound empathy, resilience, and creative strength. In this episode, you’ll hear: The "Sisterhood & Miracles" High: Kelly shares the breathtaking story of how her cousin promised at age 16 to one day carry a child for her. Twelve years later, through a beautiful journey of selflessness and sacrifice, that promise became a reality. Kelly celebrates the recent arrival of her second daughter, Elena, and the profound power of community and family in making the impossible happen. The "Waking Up to Worse" Low: A deeply raw and vulnerable account of a high-risk spinal cord surgery at age 19 that unfortunately left Kelly in exponentially worse permanent pain. She describes the terrifying moment years later when her only functioning arm collapsed while snowboard instructing, the grueling year of rehabilitation that followed, and how she learned to survive by breaking life down one single day—and one single moment—at a time. The "Creative Directing Through Crisis" Unexpected: What do you do when a rare neurological condition (Parsonage-Turner Syndrome) suddenly takes away the use of 90% of your remaining arm just weeks before a 20-wedding season? Kelly recounts how she gamely flew to California with no use of her arms and successfully shot a 12-hour wedding by stepping into the role of a Creative Director—mentally instructing her second shooter on every single setting, aperture, and ISO value. The "Hidden Masterpieces" of West Africa: Kelly opens up about living in Ghana for two years at the start of her career, creating art solely for the healing of human trafficking survivors. She shares how an environment where she was legally forbidden from posting or sharing her images served as the ultimate ego-check, teaching her to always put people and their stories above online trends and algorithmic performance. Kelly’s perspective is a masterclass in shifting your mindset from demanding a miracle outcome to finding the resilience to endure the present. If you are going through a dark valley, feeling isolated in your business, or wondering how to show up for others in their suffering, this episode will completely redefine how you view hardship. Listen now on High, Low, and Unexpected. 🎙️ Want to connect with Kelly? Follow her stunning adventure photography and real-life journey on Instagram @kellylemon or check out her work at KellyLemonPhotography.com.

    1h 11m

  3. Jun 10

    The Architecture of Alignment: Intuition, Illumination, and Reclaiming Calm (ft. Tori Stauffer)

    This week on High, Low, and Unexpected, Shaun sits down with Tori Stauffer, a Florida-based mentor and business coach for female entrepreneurs. Before stepping into the coaching world, Tori spent 15 years building a highly successful, six-figure photography brand in Philadelphia—navigating transitions from family portraits to high-end newborns and artful maternity. In this episode, you’ll hear: The "Radical Relocation" High: Tori shares the intentional decision to pack up her family of six and move to Florida to reclaim a slower pace of life. She describes the magic of watching her kids play in the cul-de-sac and bike to school, and how changing her environment unlocked a version of herself she didn't know existed. The "Wake-Up Call" Low: A deeply raw and moving look at the cost of chronic hustle. At 37, Tori received a terrifying cancer diagnosis. She opens up about the three words that changed her life ("You have cancer"), the fierce mindset shift required to ensure her 3-year-old would remember her, and the humbling realization that she had a dysregulated nervous system that was literally addicted to work and terrified of calm. The "40k Threshold" Unexpected: What happens when you hit your biggest financial month ever ($40,000) and realize it requires three months of grueling aftermath? Tori shares the precise moment she recognized she was recreating the exact burnout patterns that led to her illness—and how she found the courage to listen to her gut, transition out of her 15-year photography career, and pivot into full-time mentorship. Tori’s story is an invaluable masterclass for any entrepreneur who on paper says they want "freedom," but in reality, spends every quiet moment sneaking back to their laptop. This episode will challenge you to identify the specific feelings you are chasing and give you the ultimate permission to let go of the word "should." Listen now on High, Low, and Unexpected. 🎙️ Want to learn more from Tori? Skip the surface-level scrolling and follow her continued journey on Instagram @thetoristauffer.

    49 min

  4. Jun 3

    Girlbossing Too Close to the Sun: SEO, Boundaries, and Relaunching Yourself (ft. April Brown)

    This week on High, Low, and Unexpected, Shaun sits down with April Brown, a Jacksonville-based marketing, SEO, and conversion rate optimization specialist. Coming from a 10-year corporate career as a marketing director, April now helps female entrepreneurs and service-based businesses become "future millionaires"—but her most challenging project was learning how to audit her own life. In this episode, you’ll hear: The "Outranking Google" High: April shares the hilarious and terrifying story of the 6:00 AM phone call that landed her on a Zoom meeting with representatives from Google, YouTube, the NFL, and a major TV provider. Discover how her SEO strategy worked so well that she accidentally outranked the tech giants for "NFL Sunday Ticket"—and why her client forced her to turn her video off. The "Mommy Always Works" Low: A deeply vulnerable look at the reality of hyper-growth and the trap of saying "yes" to everything. April opens up about the massive burnout that led to a 36-hour workday cycle, a strain on her marriage, and the heartbreaking moment her young daughter gave her the ultimate wake-up call: "Mommy always works. We do not see her not working." The "27 Services & Rebranding for 3 Years" Unexpected: What happens when an expert spreadsheet-maker and SEO guru gets audited by her own CFO? April shares the shocking realization that she was offering 27 different services while only truly enjoying four of them—and how she completely forgot she hadn't had a "real" live website up for three years. April’s story is a powerful lesson in establishing hard boundaries with yourself, implementing systems like "Do Not Disturb" automations, and treating life like a "test season." If you are currently grinding around the clock, hiding from your inbox, or wondering how to scale without losing your family, this episode is your roadmap to pulling back and reclaiming your joy. Listen now on High, Low, and Unexpected. 🎙️ Want to connect with April? Check out her legendary 3-year landing page at AprilBrown.co or follow her journey and DM her on Instagram @aprilbrown.co.

    1h 4m

  5. May 27

    Heirlooms, Boundaries, and the Beauty of a 15-Year Journey (ft. Michael & Laura)

    This week on High, Low, and Unexpected, Shaun sits down with Michael and Laura, a husband-and-wife photography team based in Richmond, Virginia. With 15 years in the industry, their story is a beautiful testament to what happens when you prioritize relationship over transaction and intention over scale. In this episode, you’ll hear: The "Full-Time Leap" High: Laura shares the emotional journey of leaving a 9-year career as an elementary school teacher to go full-time in photography. Discover how "teacher skills" translate to wedding days and how this leap allowed them to expand their family through foster care and adoption. The "Square Footage" Low: A real-talk look at the challenges of running a business together in a small home office. Michael and Laura discuss the seasons where work-life balance felt like a myth and the difficult (but necessary) conversations required to find a healthy line between being business partners and being a married couple. The "15-Year Celebration" Unexpected: How a business built on community leads to clients who stay for a decade and a half. From receiving gifts for their children to throwing a 15th-anniversary party for their past couples, Michael and Laura explain why they don’t want "high-end" clients—they want "their people." Michael and Laura’s story is a raw reminder that while we document "perfect" days for others, our own success is found in the boundaries we set, the resilience we build in the lows, and the legacy we leave within our own four walls. Listen now on High, Low, and Unexpected. 🎙️ Want to connect with Michael & Laura? Check out their work at MichaelAndLauraPhotography.com or follow their journey and DIY projects on Instagram @michaelandlauraphotography

    1h 13m

  6. May 13

    Simplicity, Software, and the Strength of the Human Spirit (ft. Daniel Usenko)

    This week on High, Low, and Unexpected, Shaun sits down with Daniel Usenko, the visionary founder and CEO of Pixellu (Smart Albums). A photographer turned tech innovator, Daniel has spent over a decade revolutionizing how our industry handles album design, but his journey is about much more than just software. In this episode, you’ll hear: The "Integration" High: A deep dive into the two-year mission to integrate Smart Albums with KISS Books. Daniel shares why "simplicity is addictive" and how this breakthrough aims to rescue a new generation of photographers from the tedious Photoshop workflows of the past. The "Broken Back" Low: A raw and humbling look at the physical cost of pushing limits. After completing a full Ironman for his 40th birthday, Daniel discovered he had been living and working with a broken back for months—forcing a difficult conversation about health, aging, and what it means to be present for your family. The "Reinvention" Unexpected: How losing his personal domain name led to a two-year hiatus from the web, and how a recent spark at a creative conference inspired him to relaunch his site and embrace "boring" family photos as the ultimate proof of life.Daniel’s story is a refreshing blend of tech-forward thinking and old-school appreciation for the tangible. Whether you’re struggling with business growth or a personal setback, this conversation will remind you that while technology moves fast, the most valuable things—our health and our memories—require us to slow down.Listen now on High, Low, and Unexpected.🎙️ Want to connect with Daniel? Check out SmartAlbums.com, his new photography site at Usenko.co, or follow his personal journey on Instagram @danielsenko.

    41 min

  7. May 6

    Vulnerability, Value, and the Power of 'Yes' (ft. Amanda Waltman)

    This week on High, Low, and Unexpected, Shaun sits down with Seattle-based family photographer and podcast host Amanda Waltman. With over 23 years in the industry, Amanda’s journey is a masterclass in reclaiming your identity and finding strength in life’s most humbling moments. In this episode, you’ll hear: The "Legion of Youth" High: How a random connection led to a decade-long partnership with the Seattle Seahawks, allowing Amanda to document the stories of homeless and at-risk youth during the team's Super Bowl era. Reclaiming Autonomy: The "Low" that forced Amanda to quit photography for a year after being told her laugh was "too loud" for a corporate studio—and how she returned on her own terms. Redefining Success through Loss: A heartbreaking and honest look at navigating back-to-back miscarriages, and how motherhood finally broke her addiction to the 80-hour "hustle" culture. The 'Series of Unfortunate Events' Unexpected: From her husband’s tech layoff to a freak accident that left Amanda with a broken foot and surgery during her busiest season, she shares the lesson her therapist gave her: "Just say yes to the help." Amanda’s story is a raw reminder that entrepreneurship isn't a straight line. It’s a series of peaks and valleys that test our resolve and force us to decide who we want to be when we can no longer "do it all" ourselves. Listen now on High, Low, and Unexpected. 🎙️ Want to hear more from Amanda? Check out her podcast at TheEditWeekly.com or follow her photography journey on Instagram @amandawaltmanphoto!

    1h 12m

  8. Apr 29

    Systems, Scaling, and Small Town Success (ft. Kylee Maughan)

    This week on High, Low, and Unexpected, Shaun sits down with northern Utah photographer and business coach Kylee Maughan. With 15 years in the industry, Kylee has mastered the art of the "mompreneur" shuffle—growing a multiple six-figure brand while remaining a present, hands-on mom. In this episode, you’ll hear: The "Groove" High: How Kylee reached the point where her business generates $500K+ while she still has time to volunteer at her kids' school and read 75 books a year. The Adrenal Failure Low: A vulnerable look back at 2016, when running a high-volume business with 75+ weddings and zero systems led to a stress-induced health crisis. The Power of the First Hire: Why outsourcing editing and bringing on a Virtual Assistant (VA) is the only way to move from "owning a job" to "owning a business." The Pivot to Branding: How the 2020 lockdown forced a shift from weddings to baby brand photography, eventually leading to a dream collaboration with the iconic Gerber Baby brand. Kylee’s journey is a powerful reminder that we don’t rise to the level of our goals—we fall to the level of our systems. Whether you are feeling burnt out in the "editing cave" or looking to scale your team, this conversation offers a roadmap to building a business that serves your life, not the other way around. Listen now on High, Low, and Unexpected. 📸 Ready to stop the hustle and start scaling? Check out Kylee Maughan’s coaching and photography at KyleeAnne.com or follow her behind-the-scenes on Instagram @kyleeann.maughan!

    40 min
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Ratings & Reviews

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out of 5
5 Ratings

About

In this podcast, we explore the remarkable successes, challenges, and unexpected turns that entrepreneurs encounter in their careers.

Information

  • Creator
    Shaun Gordon
  • Years Active
    2024 - 2026
  • Episodes
    41
  • Rating
    Explicit
  • Copyright
    © Shaun Gordon
  • Show Website
    High, Low and Unexpected