High, Low and Unexpected

Shaun Gordon
  • 5.0 (5)
  • Business
  • Updated Weekly

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

  1. 11h ago

    The Frame of Accountability: Reclaiming Back-Burner Dreams, Out-of-Focus Realities, and the Hidden Gift of Pain (ft. Amanda McKinney)

    This week on High, Low, and Unexpected, Shaun sits down with Amanda McKinney, a Tulsa-based accountability coach, author, and strategic positioning specialist. Originally a Florida native who navigated the structural shift of moving inland to Oklahoma, Amanda spent years climbing the corporate ladder as a high-level marketing director before an unexpected department-wide layoff forced her into the world of accidental entrepreneurship. Today, she helps highly successful female founders strip away the structural clutter of their businesses to finally execute the legacy goals they've left on the back burner. In this episode, you’ll hear: The "One-Year Manuscript" High: Amanda shares the complicated reality of writing and publishing her acclaimed book, Why Not You? An Accidental Entrepreneur’s Guide to Success, within a single calendar year. Discover what it actually feels like to hold your physical book for the first time, why she completely skipped a traditional launch party due to severe self-doubt, and the retrospective pride she feels today for executing a high-stakes legacy project while her personal life was completely out of alignment. The "Out-of-Focus Blur" Low: A hilarious, gut-wrenching, and entirely human look at the worst operational failure of Amanda’s career. She details spending an entire grueling day scripting and filming a premium digital marketing course—only to upload the cards and discover every single second was completely out of focus. Learn why she immediately crawled into her closet to record a raw, unfiltered podcast episode mid-crisis and why she has operated with a non-negotiable checklist margin ever since. The " severance Strategist" Unexpected: What happens when the corporate safety net disappears overnight? Amanda recounts the shock of being laid off in her early thirties and the incredible job interview where she actively talked herself out of a traditional position—convincing the company to hire her as an independent external consultant before she even owned a registered business name. From Shaun’s first public deceleration of his disruptive vision for Kiss Books—using the wedding album framework to actively combat global divorce rates—to structural boundaries and brain dynamics, this conversation will challenge you to evaluate your cognitive limitations, release your artificial "shoulds," and step directly into your true zone of execution. Listen now on High, Low, and Unexpected. 📖 Ready to step off the corporate treadmill? Grab your copy of Amanda’s blueprint and explore her full positioning framework at AmandaMcKinney.com or slide into her DMs on Instagram @amandamckinneycoach to share your biggest transactional takeaways!

  2. Jul 29

    The Architecture of Order: Releasing the Visionary, Porsche Swinging Legacies, and Ordering the Chaos (ft. Chynna Benton)

    This week on High, Low, and Unexpected, Shaun sits down with Chynna Benton, the brilliant founder of Byte Bodega and a high-level Online Business Manager (OBM) and integrator for creative CEOs. Operating out of the Boston area, Chynna specializes in step-by-step operational management for educators, membership creators, agency owners, and coaches who have successfully scaled their front-end offers but are drowning in the day-to-day background execution of their own brands. In this episode, you’ll hear: The "Accidental Side-Hustle" High: Chynna breaks down her incredible business origin story. Starting in wedding and events management, she took a digital technology course in 2016 simply to fight for a corporate raise. Discover how an excuse to "just practice building a website" rapidly spiraled into a full client roster, allowing her to confidently hand in her notice six months later when upper management failed to match her market value. The "Amsterdam Curveball" Low: A deeply moving and transparent look at running a people-first business during unexpected family tragedy. Chynna shares the devastating reality of losing her beloved grandmother via a FaceTime call while thousands of miles away on a strict off-grid vacation in Amsterdam. She details the exhaustion of missing flights, emotional breakdowns at the KLM customer counter, and how having airtight operational documentation allowed her to take a month off to mourn with her family while her clients' systems continued to run seamlessly. The "Course Launch Pivot" Unexpected: What happens when you spend a year and a half building a self-paced training program, only to realize you absolutely detest being the public face of the brand? Chynna opens up about hitting a wall of burnout, entering a three-day silent notebook retreat in her apartment, and making the bold, unexpected U-turn to return to behind-the-scenes operations—proving that changing your mind is one of the most powerful tools an entrepreneur owns. From the difference between a Virtual Assistant (VA) and an Online Business Manager (OBM) to analyzing the energy drain on your personal battery using electric vehicle metaphors, Chynna’s framework is an outstanding masterclass in organizational engineering. Listen now on High, Low, and Unexpected. 📦 Ready to protect your brand from systemic fires? Chynna is offering our community her premium, step-by-step Chaos Proof Your Business blueprint. Head over to ByteBodega.com to audit your structural holes! 📸 Connect with Chynna: Follow her highly operational behind-the-scenes updates on Instagram @byte_bodega or join her hilariously unhinged community newsletter list.

  3. Jul 22

    The Frame of Courage: In-Person Sales Mastery, High School Haters, and the Legacy of the Shutter (ft. Matthew Orbaugh)

    This week on High, Low, and Unexpected, Shaun sits down with an absolute prodigy of the modern photography scene, Matthew Orbaugh. Based in the Indianapolis area with a dedicated studio in Zionsville, Matthew has built a soaring trajectory as a premier senior portrait photographer and editorial visual artist. What makes this conversation incredibly special is that Matthew is the exact photographer who captured Shaun’s daughter Haley’s wedding in August 2025—navigating a deeply personal family milestone with unparalleled maturity. In this episode, you’ll hear: The "In-Person Sales" High: Matthew details his monumental pivot away from the traditional, volume-based "shoot and burn" business model to a high-end, in-person sales (IPS) method right after graduating high school. Discover how charging premium rates allowed him to increase his revenue by three times while working less, elevating his brand from a simple digital transaction to a luxurious, sensory-driven senior experience. The "33-Year-Old Hater" Low: A shocking, raw account of the toxic side of local industry competition. Matthew vulnerably shares what it felt like as a young creator to be systematically targeted, bashed to friends, and harassed in his Instagram DMs by a seasoned 33-year-old female photographer intent on shutting his business down. He breaks down the exact mindset shift required to convert cyber-bullying into direct fuels for professional success. The "Relational Blueprint" Unexpected: A beautiful look at the profound network generated by a camera lens. Matthew reflects on how skipping the traditional college path allowed him to cultivate long-term, multi-city friendships, past clients running into him at university towns, and the deep emotional permanence of designing tangible custom albums that outlive depreciating luxury items. From dynamic show choir pep talks given by legendary instructors to the exact strategy required to become the most expensive creative in your zip code, Matthew’s framework is an outstanding blueprint for any artist trying to conquer corporate self-doubt. Listen now on High, Low, and Unexpected. 📸 Ready to transform your visual framework? Follow Matthew’s funky fashion editorials and real-time studio updates on Instagram @mattheworbaughphoto.

  4. Jul 16

    The Architecture of Freedom: Relational Grit, Facing the Valleys, and Why Pictures Matter (ft. Lifestyle & Lenses)

    This week on High, Low, and Unexpected, Shaun sits down with the dynamic duo behind Lifestyle & Lenses—Houston-based photographers, podcasters, and educators Lauren and Paige. Combining well over 30 years of history in the photography industry, they have unified their distinct professional frameworks—one built from leaving the high-pressure layers of corporate America, the other from climbing out of the stay-at-home mom routine into a six-figure business—to create a step-by-step masterclass that helps creative entrepreneurs successfully transition to full-time status. In this episode, you’ll hear: The "Shared Dream" High: Lauren and Paige look back on their first year of collaborative education, celebrating the intense satisfaction of hitting goals without relying on vanity metrics. They share the profound fulfillment of watching their own members break free from traditional employment, complete with the raw, emotional milestone of cheering a student right to the edge of full-time status. The "Daycare Dilemma" Low: Lauren shares a deeply personal account of her corporate past, detailing the gut-punch realization of missing her daughter’s first steps and words while helping someone else achieve their business goals. Discover how she built a strategic financial cushion to reclaim control over her family schedule and why being your own boss means choosing your hard hours on your own terms. The "Variable Pressure" Second Low: Paige breaks down the weight of variable income and the absolute execution required when your business suddenly becomes the primary financial pillar for your family. She opens up about discovering her husband lost his job in the middle of a major industry conference, navigating sleepless nights without letting her client experience drop, and using physical wellness as a non-negotiable mental boundary. The "Unscripted Obits" Unexpected: A heavy, beautiful, and perspective-shifting look at the real weight of photography. Lauren and Paige share the sobering reality of being called to photograph children on hospice, a baby's funeral, and families whose final portraits become obituaries within months. They remind us that behind every click of the shutter is a permanent anchor for human grief, community healing, and unconditional love. Lauren and Paige’s journey is an essential framework for any creative who is currently using the word "should" to measure their growth. This conversation will challenge you to evaluate your pricing, lock down your operational boundaries, and build a system strong enough to weather any oncoming storm. Listen now on High, Low, and Unexpected. 🎙️ Want to scale your creative brand? Skip the surface-level scrolling and explore their full framework at LifestyleAndLenses.com or connect with their unscripted episodes on YouTube and Instagram @lifestyleandlenses.

  5. Jul 9

    The Architecture of Authority: Seducing the AI Machines, Postpartum Realities, and Being Impossible to Ignore (ft. Monique Bryan)

    This week on High, Low, and Unexpected, Shaun sits down with Monique Bryan, a Toronto-based brand authority strategist, international creative, and founder. With over 15 years of hard-hitting entrepreneurial experience navigating everything from fashion design and manufacturing in India and China to building legacy coaching programs, Monique specializes in helping founders become the absolute, obvious choice in a world where AI engines are doing the recommending. In this episode, you’ll hear: The "Holy Grail" High: Monique takes us back to the early days of her creative career, detailing a wild, three-minute pitch at New York’s iconic Henri Bendel department store. Discover what it actually took to get her collection past international customs by literally wearing 87 heavy necklaces and bracelets across the border, winning an "American Idol-style" designer callout, and the humbling reality check of standing on her feet for four days waiting for the payout. The "0.05% Miracle & The 60k Trap" Low: A deeply transparent and breath-catching account of balancing unpredictable growth. After surviving breast cancer and being told a natural pregnancy was statistically impossible, Monique details the shocking discovery of her pregnancy—just weeks after signing a $60,000 contract with the Marriott Group for her dream business retreat. She opens up about the silent toll of postpartum depression, feeling like she lost her "sparkle," and the absolute necessity of leaning on structured coaching and professional therapy to rebuild. The "Lori Harder Stage" Unexpected: What happens when you declare your biggest goals out loud to an industry icon with millions of followers? Monique shares the hilarious and pivotal moment she boldly told Lori Harder she would be on her California stage within a year—and the sudden, terrifying DM months later where Lori held her to her word, forcing her to conquer her imposter syndrome and step into her true authority. Monique’s story is a brilliant framework for any creative entrepreneur who is tired of watching less-qualified peers grab all the digital attention simply because they know how to show up louder. This conversation will challenge you to drop the vanity metrics, structure your boundaries, and implement dynamic systems that make your business completely impossible to ignore. Listen now on High, Low, and Unexpected. 🎙️ Want to run your own authority report? Monique is giving our audience FREE access to her high-end Answer Engine Optimization audit tool. Head over to MoniqueBryan.com/audit (Bryan with a 'Y') and use the promo code HIGHLOW at checkout to see exactly how the AI machines are recommending you! 📸 Connect with Monique: Follow her sharp insights and daily updates on Instagram @moniquebryan_co or subscribe to her raw behind-the-scenes thoughts on Substack at The Anti-Personal Brand.

  6. Jul 2

    Freefall and Healing: Cultivating Optimism, Community, and the Reality of Loss (ft. Becca Lueck)

    This week on High, Low, and Unexpected, Shaun sits down with Becca Lueck, a Portland-based adventure family photographer and educator. Moving from a stable corporate structure in education to full-time entrepreneurship, Becca’s approach is a masterclass in calculated risk, resilience, and finding the ultimate "glass-half-full" perspective when life hits the hardest valleys. In this episode, you’ll hear: The "I Am Free" High: Becca shares the exhilarating milestone from 2021 when she finally quit her Title I reading assistant job to take her photography business full-time. She opens up about overcoming the fear of leaving guaranteed income, managing a cautious spouse’s perspective, and the sheer momentum that allowed her to almost triple her earnings in her very first year. The "Stage Four" Low: A deeply raw and moving account of navigating a massive conference season while processing her mother’s terminal cancer diagnosis and subsequent passing. Becca shares the emotional toll of carrying heavy personal grief behind the scenes, the isolation of attending events alone, and how an intentional 2.5-week family trip to Europe became a vital space for collective mourning and healing. The "Clubhouse Blueprint" Unexpected: What happens when your 2020 leap into full-time entrepreneurship is instantly halted by a global lockdown? Becca breaks down how she utilized the sudden influx of time to stack her brand, step into the early spaces of the Clubhouse app, and find the confidence to transition from selling presets to launching a highly successful education and mentoring platform. Becca’s story is a beautiful reminder that while our craft allows us to stop time, life outside the frame continues to move forward. If you are a solo entrepreneur feeling the strain of holding space for others while draining your own emotional battery, this conversation will give you the grace and permission to slow down and prioritize what matters most. Listen now on High, Low, and Unexpected. 🎙️ Want to connect with Becca? Follow her stunning Pacific Northwest family adventures and real-time updates on Instagram @beccajeanphotography.

  7. Jun 24

    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.

  8. 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.

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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
    47
  • Rating
    Clean
  • Copyright
    © Shaun Gordon
  • Show Website
    High, Low and Unexpected