How To Convert Headshot Clients Into Portrait Clients with Leticia Andrade

Rejection, unpredictable income and self-doubt can be harder to manage than lighting or posing. Photographer and filmmaker Ajani Charles joins Nikki Closser to talk about the mental side of building a photography business—and the relationships, routines and practical business habits that help him keep going.Ajani shares the story behind Project T-Dot, his long-running documentary project on Toronto's hip-hop culture, community and history. He explains why he stayed with it for 15 years before monetizing it, how commercial work supported him along the way, and what a personal project can offer beyond an immediate paycheck.The conversation also gets practical about finding photography clients: being useful, solving a client's problem, defining an ideal client and following up. Alongside those business habits, Ajani discusses the role that meditation, therapy, journaling and a trusted support system have played in his own life.In this conversation:Personal photography projects, long-term relationships and creative identityRejection, financial uncertainty and clearer business goalsRemembering your wins and finding support during difficult periodsMarketing through usefulness, trust and client problem-solvingIdeal client profiles, CRM follow-ups and consistent outreachBuild your photography business with PortraitSystem.com. Use code PODCAST7 for your first month for $7.Chapters00:00 The mental side of a photography business01:34 Ajani's start in art and photography04:10 Project T-Dot: photographing Toronto hip-hop10:11 15 years to monetize a personal project17:34 Rejection, money and creative-career uncertainty22:15 Remembering your wins when criticism sticks27:32 Meditation, therapy and journaling33:58 Photography marketing: trust and usefulness37:24 Ideal clients, CRM and follow-ups39:46 Taking action after a no45:27 Mentors and a creative support system47:51 Four final questions: routines, gear and getting started

Drew Forsyth is an award-winning portrait photographer and director based in the North West of England, working with commercial and advertising clients across the UK and internationally. His work centres on people who've given everything to be extraordinary at what they do — from dancers with English National Ballet and musicians of the BBC Philharmonic and the Hallé Orchestras, to Nobel Prize-winning scientists, politicians, and performers at the height of their careers. His photography has been featured by BBC News, The Guardian, The Times, and Rolling Stone, and recognised by the Royal Society of the Arts. He's an AOP Accredited Photographer and Fellow of the RSA, and speaks internationally at events like Photo North, Pas de Deux Photo Conference, and the Royal Photographic Society.In this episode, Drew and Nikki trace his path from a JCPenney-style family portrait studio to photographing world leaders, Nobel laureates, and major corporate campaigns — and he breaks down exactly how he prices that work today. They dig into setting boundaries on set (and how to say yes to more without losing your mind), why those early "conveyor belt" studio years became his real technical training, and why he believes his biggest competition isn't other photographers — it's being forgotten. Drew also walks through how he actually quotes corporate jobs (day rates, itemized breakdowns, and the cautionary tale of a client who blamed him for "cheap-looking" dresses), how personal passion projects like his "Breaking Ground" series and a helicopter shoot over Manhattan became his best marketing, and the "Helsinki Bus Station Theory" — his framework for why so many photographers give up on their style right before it becomes distinctive.Topics covered:Setting boundaries with clients without losing bookingsWhy "conveyor belt" studio work builds indispensable technical skillsThe accidental path from individual sessions to corporate/organizational clientsPricing corporate shoots: day rates, itemized quotes, and scope questionsWhy past-client relationships and personal introductions beat cold outreachMarketing through consistent presence, not constant hard-sellingPassion projects as a client-acquisition strategyThe Helsinki Bus Station Theory: staying the course creativelyIf you're building a photography business, want to grow your portrait photography income, or are curious about how to make money from photography online, this conversation is packed with actionable advice. 👉 For more videos like this, visit: https://theportraitsystem.com/ABOUT THE PORTRAIT SYSTEM:The step-by-step system to turn your portrait photography into a profitable business.Build a solid foundation for the portrait business you want. Attract the right clients over and over again. Confidently create the work you're proud of. Streamline, scale, and grow with purpose.Join an international community of thousands of photographers learning to build and succeed in their portrait businesses.With hundreds of specially designed courses to help you create and grow a profitable contemporary portrait business.Whether you're starting out or scaling up, The Portrait System gives you the tools to build a portrait business that supports your life.FOLLOW US: JOIN The Portrait System: https://theportraitsystem.com/ FB: /theportraitsystem IG: /theportraitsystem

Caroline White has been a professional photographer for 21 years — starting as an actress shooting headshots on the side before a burglary wiped out her equipment and pushed her into photography full-time. Since 2011 she's averaged six figures a year shooting personal branding for women entrepreneurs and coaches, and more recently has pivoted into a passion project: underwater portrait photography.In this episode, Caroline and Nikki dig into pricing high-touch branding packages (from $2,500 simple sessions to a $20,000 two-and-a-half-day shoot), the "asshole insurance" strategy that protects her boundaries while letting her overdeliver for great clients, how AI is affecting (and not affecting) the personal branding photo market, and her transition from packages to in-person sales for underwater work — including handmade, rhinestone-embellished prints. Caroline also opens up about the near-drowning experiences that shaped her fearlessness in the water and her ability to help nervous clients feel safe underwater.Topics covered:Building a 6-figure business without weddings or paid adsHow marketing lag works — and what happens when you stopAdd-ons that increase average sale (rush orders, retouching tiers, split-day shoots)"Asshole insurance": overdelivering for good clients, holding boundaries with difficult onesAI's real impact on personal branding photographyUnderwater photography: gear, safety, and working with non-swimmersTransitioning from packages to in-person sales (IPS)Handmade art pieces: painting on prints, Swarovski crystals, double exposuresIf you're building a photography business, want to grow your portrait photography income, or are curious about how to make money from photography online, this conversation is packed with actionable advice. 👉 For more videos like this, visit: https://theportraitsystem.com/ABOUT THE PORTRAIT SYSTEM:The step-by-step system to turn your portrait photography into a profitable business.Build a solid foundation for the portrait business you want. Attract the right clients over and over again. Confidently create the work you're proud of. Streamline, scale, and grow with purpose.Join an international community of thousands of photographers learning to build and succeed in their portrait businesses.With hundreds of specially designed courses to help you create and grow a profitable contemporary portrait business.Whether you're starting out or scaling up, The Portrait System gives you the tools to build a portrait business that supports your life.FOLLOW US: JOIN The Portrait System: https://theportraitsystem.com/ FB: /theportraitsystem IG: /theportraitsystem

What happens when a portrait photographer stops thinking like a freelancer and starts thinking like a CEO? Jaren Collins did exactly that — and built JCi Creatives, a nationwide creative agency specializing in conference and event storytelling, with clients including AT&T and the Thurgood Marshall College Fund.In this episode, Jaren breaks down:How he quit his corporate job (with almost nothing saved) and matched his salary within a monthWhy he walked away from 52 weddings a year to pursue corporate clientsHow one $1,000 gig turned into nearly $100,000 in annual spend from a single clientHis approach to project-based pricing and asking "what's your budget" upfrontHigh-volume headshot strategy — including doing 75 headshots in 23 minutesThe systems, AI tools, and team structure that keep his business running efficientlyWhy referrals in the corporate world are massively underutilizedJaren also co-owns Greenwood Co., a creative coworking and content space in DeSoto, Texas built to empower creators and entrepreneurs — and his mission is to help others turn creativity into sustainable, legacy-building businesses.Whether you want to break into corporate photography or scale what you've already built, this episode is full of real-world strategy you can use today.If you're building a photography business, want to grow your portrait photography income, or are curious about how to make money from photography online, this conversation is packed with actionable advice. 👉 For more videos like this, visit: https://theportraitsystem.com/ABOUT THE PORTRAIT SYSTEM: The step-by-step system to turn your portrait photography into a profitable business. Build a solid foundation for the portrait business you want Attract the right clients over and over again Confidently create the work you're proud of Streamline, scale, and grow with purposeJoin an international community of thousands of photographers learning to build and succeed in their portrait businesses.With hundreds of specially designed courses to help you create and grow a profitable contemporary portrait business.Whether you're starting out or scaling up, The Portrait System gives you the tools to build a portrait business that supports your life.FOLLOW US: JOIN The Portrait System: https://theportraitsystem.com/ FB: /theportraitsystem IG: /theportraitsystem

In this episode of The Portrait System Podcast, Nikki sits down with photographer and educator Meg Loeks to talk about how she built a photography business rooted in storytelling, color, and creativity. Meg shares how she went from a corporate marketing job to running a thriving portrait business, and how life circumstances eventually led her to focus fully on photography education.They talk about building momentum through social media, finding clients through your network, evolving your style, using color intentionally, and how education can become a powerful second income stream for photographers. Meg also shares her approach to photographing families, styling sessions, working with created light, and growing a loyal audience online.If you’re a photographer interested in building a business, refining your artistic voice, or eventually stepping into education, this conversation is full of insight and encouragement.Meg’s work is known for its rich storytelling, cinematic lighting, and thoughtful use of color, and this episode gives a great behind-the-scenes look at how she thinks about both art and business.If you’re building a photography business, want to grow your portrait photography income, or are curious about how to make money from photography online, this conversation is packed with actionable advice.👉 For more podcasts like this, visit: https://theportraitsystem.com/ABOUT THE PORTRAIT SYSTEM:The step-by-step system to turn your portrait photography into a profitable business.Build a solid foundation for the portrait business you wantAttract the right clients over and over againConfidently create the work you’re proud ofStreamline, scale, and grow with purposeJoin an international community of thousands of photographers learning to build and succeed in their portrait businesses.With hundreds of specially designed courses to help you create and grow a profitable contemporary portrait business.Whether you’re starting out or scaling up, The Portrait System gives you the tools to build a portrait business that supports your life.FOLLOW US:JOIN The Portrait System: https://theportraitsystem.com/FB: /theportraitsystemIG: /theportraitsystem

In this episode of The Portrait System Podcast, Nikki sits down with South Africa–based photographer Simone Dorfman to talk about real-life marketing strategies that actually work. Simone shares how she built a photography business with a $2,000 average sale in a small town by offering personal branding photography, product photography, and content creation services for small businesses.They discuss:• Photography marketing strategies for small markets• How to increase photography pricing through value-adds• Running simple Instagram and Facebook ads• Partnering with stylists and content creators• Packaging B-roll social video with photography sessions• Booking branding clients through networking• Creating photography packages for small business ownersIf you’re a photographer looking to increase your photography pricing, attract better branding clients, and simplify your marketing strategy, this episode is packed with actionable advice you can use right away.If you’re building a photography business, want to grow your portrait photography income, or are curious about how to make money from photography online, this conversation is packed with actionable advice.👉 For more videos like this, visit: https://theportraitsystem.com/ABOUT THE PORTRAIT SYSTEM:The step-by-step system to turn your portrait photography into a profitable business.Build a solid foundation for the portrait business you wantAttract the right clients over and over againConfidently create the work you’re proud ofStreamline, scale, and grow with purposeJoin an international community of thousands of photographers learning to build and succeed in their portrait businesses.With hundreds of specially designed courses to help you create and grow a profitable contemporary portrait business.Whether you’re starting out or scaling up, The Portrait System gives you the tools to build a portrait business that supports your life.FOLLOW US:JOIN The Portrait System: https://theportraitsystem.com/FB: /theportraitsystemIG: /theportraitsystem

Most photographers don’t fail because of their photography, they fail because of pricing and marketing. In this episode of The Portrait System Podcast, Nikki sits down with Vanessa Joy (working photographer + educator, in business since 2008) to talk about what it really takes to keep a photography business profitable and sustainable.In this conversation, Vanessa breaks down:Why “I need more leads” is usually the wrong problemHow to market with a wide net (and why there’s no magic bullet)The biggest fix when you’re “posting everywhere” but still not getting inquiriesHow to audit your first impression (website + social + messaging)Sales + branding: why “branding” is really voice + communicationPricing without emotion: how to use math + data to set prices that actually support your lifeOutcome-based selling: stop selling “hours + number of images” and sell the transformationRaising prices without panic: keeping some clients, losing others, and finding the next pondSystems that prevent burnout: CRM workflows, email templates, SOPs, automationsHiring associate photographers: how to sell “the studio/team” (not just you)If you’re serious about building a photography business that lasts, this episode will save you years of trial and error.Find Vanessa:VanessaJoy.com (photo work + corporate work + education)If this helped, subscribe, share it with a photographer friend, and drop a comment: What’s harder for you right now — pricing or marketing?If you’re building a photography business, want to grow your portrait photography income, or are curious about how to make money from photography online, this conversation is packed with actionable advice.👉 For more videos like this, visit: https://theportraitsystem.com/ABOUT THE PORTRAIT SYSTEM:The step-by-step system to turn your portrait photography into a profitable business.Build a solid foundation for the portrait business you wantAttract the right clients over and over againConfidently create the work you’re proud ofStreamline, scale, and grow with purposeJoin an international community of thousands of photographers learning to build and succeed in their portrait businesses.With hundreds of specially designed courses to help you create and grow a profitable contemporary portrait business.Whether you’re starting out or scaling up, The Portrait System gives you the tools to build a portrait business that supports your life.FOLLOW US:JOIN The Portrait System: https://theportraitsystem.com/FB: /theportraitsystemIG: /theportraitsystem

Taxes don’t have to be the thing you avoid until April. In this episode of The Portrait System, Nikki sits down with Heather Leicy (tax prep educator + bookkeeper + working photographer) to break down photographer tax deductions, year-round tax prep, and the biggest “can I write this off?” mistakes.You’ll learn:What to do monthly so you’re not scrambling at tax timeA simple system for setting aside 20–30% for taxesCommon photographer deductions: education, software, gear, website costs, client giftsThe truth about meals/coffee write-offs (when it counts, when it doesn’t)Home office deduction basics and “dedicated space” rulesWhy mileage tracking is one of the most missed deductions (and the app Heather recommends)A simple breakdown of LLC vs S-corp taxation and why it’s a math decisionWhy sales tax rules vary so much by state (digital vs physical vs services)Important: This episode is for educational purposes only and is not tax, legal, or accounting advice. Tax laws vary by location and change over time. Always consult a qualified CPA/tax professional about your specific situation.Find HeatherInstagram: @heather.marie.LeicyCommunity: Conquer Community – theconquercommunity.comIf you enjoyed this episode, please subscribe, leave a review, and share it with a photographer friend who needs a tax reset.

What does it really take to photograph celebrities and musicians and build a photography career that actually lasts?In this episode of The Portrait System Podcast, Nikki Closser sits down with Jim Wright, a renowned photographer who has worked with iconic musicians, A-list celebrities, and major publications. Jim pulls back the curtain on the real business of celebrity and music photography - beyond the glamour.You’ll learn:How Jim broke into celebrity and music photography without a traditional planThe truth about licensing, usage, and work-for-hire contractsWhen (and when not) to shoot for exposureWhy relationships matter more than portfoliosHow personal work, family portraits, and commercial projects can coexistWhat photographers misunderstand about pricing and sustainabilityWhether you’re an aspiring photographer or an established pro, this conversation is packed with honest insights about longevity, creative integrity, and building a career on your terms.

Get a FREE Posing eBook from The Portrait System here: https://the-portrait-system.lpages.co/podcast-pose-funnel/Today, on The Portrait System Podcast, our guest is portrait & lifestyle photographer Damien Carter. Listen in as host Nikki Closser interviews Damien about how he built his business for success in less than a year after being laid off from his full-time job. Damien tells us all about how he keeps his prices high and clients coming back. If you're looking for inspiration this week, then this episode is for you!PODCAST LISTENER SPECIAL!! If you want to get started with the Portrait System, get a special discount using code “POD7” to get one month access for just $7 here https://theportraitsystem.com/pricing/IG https://www.instagram.com/theportraitsystem/YouTube https://www.youtube.com/c/theportraitsystem