Podcast
High, Low and Unexpected
Hosted by Shaun Gordon · EN
In this podcast, we explore the remarkable successes, challenges, and unexpected turns that entrepreneurs encounter in their careers.
34episodes
Episodes
Newest firstAll episodes
Heirlooms, Boundaries, and the Beauty of a 15-Year Journey (ft. Michael & Laura)
1w ago01:13:28Tap to summarizeThis 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
Transcribe →Simplicity, Software, and the Strength of the Human Spirit (ft. Daniel Usenko)
3w ago00:40:40Tap to summarizeThis 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.
Transcribe →Vulnerability, Value, and the Power of 'Yes' (ft. Amanda Waltman)
4w ago01:11:58Tap to summarizeThis 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!
Transcribe →Systems, Scaling, and Small Town Success (ft. Kylee Maughan)
Apr 2900:39:30Tap to summarizeThis 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!
Transcribe →Perspective, Resilience, and The Gray Areas (ft. Jes Workman)
Apr 2201:00:40Tap to summarizeThis week on High, Low, and Unexpected, Shaun sits down with Los Angeles-based wedding photographer Jes Workman to talk about the soulful side of film photography and the grit required to sustain a global creative business.Jes has built an incredible brand centered on deep, lasting connections, often transitioning from "the photographer" to a lifelong friend for her clients.In this episode, you’ll hear:The "Alignment" High: How Jes shifted her business to attract clients who share her values, and why being invited into their homes years later to document their next chapters is the ultimate success.The 2020 Reality Check: A vulnerable look at the year Jes went from 38 scheduled weddings to just 4, and the hard lessons learned about financial stability, survival, and calling on family for support.The "Fairness" Trap: Jes shares an unexpected story of a high-profile wedding that appeared perfect on the outside but challenged her professionally behind the scenes.Building Business Muscles: How navigating "heavy-weight" challenges—like a global pandemic or unfair treatment—builds the resilience needed to handle the daily stresses of entrepreneurship with ease.Jes’s story is a powerful reminder that entrepreneurship isn’t just about the beautiful end product—it’s about the strength we gain through the struggle and the perspective we find in the clouds.Whether you’re looking to find your own creative spark, navigate a difficult season, or simply be reminded that your unique voice matters—this conversation will meet you there.Listen now on High, Low, and Unexpected.📸 Want to see Jes’s incredible film work and follow her global adventures? Check out JesWorkman.com or follow her on Instagram @jesworkman!
Transcribe →Artistry, Alignment, and the Startup Grind (ft. Isabella Rosendale)
Apr 1500:29:23Tap to summarizeThis 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!
Transcribe →Time Freedom and Business Scaling (ft. Taylor Jackson)
Apr 700:48:38Tap to summarizeThis 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 passionWhy money management is more important for creatives than buying the next new lensHow consistent YouTube content leads to trust and partnerships with major brands like Nikon and LeicaThe power of building relationships and a supportive community in the photo industryTaylor 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!
Transcribe →Superpowers, Survival, and the Unoffendable Spirit (ft. Matt Gruber)
Mar 2401:03:20Tap to summarizeThis 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!
Transcribe →Serving Clients, Building Legacy (ft. Rob Greene)
Oct 700:37:48Tap to summarizeThis 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 pressureThe power of follow-up and how it drives connection (and income)Why delegation and margin matter more than hustleWhat legacy really looks like as a creative business ownerRob 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!
Transcribe →From Doing It All to Doing What Matters (ft. Nata Salvatori)
Sep 2400:50:22Tap to summarizeThis 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 entrepreneurWhy high-functioning burnout is so hard to spot—and what to do about itHow Nata went from dropping balls to building a team she trustsWhat it really means to run a business that gives you your life backThis 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.
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