How this Wedding Photographer Plans to Save 180 Hours a Year With Better Systems with Jordan Craig
11/06/2026 | 45 mins.
What if the biggest thing holding your business back wasn't marketing, pricing, or lead generation, but the fact that everything lived inside your head? In this episode, I sit down with Jordan Craig, a wedding photographer who joined Systems in Session after years of managing inquiries, contracts, invoices, reminders, and client communication manually. Together, we unpack what happened when he moved from a patchwork process of Gmail, reminders, QuickBooks, and memory-based workflows into a streamlined Dubsado system designed to support both his business and his life. Jordan shares what surprised him most about the experience, how automation improved his client experience instead of making it feel robotic, and why he believes he'll gain back more than 180 hours every year because of the systems we built together.
Find It Quickly 00:24 - Meet Jordan 01:32 - The Chaos Before Dubsado 03:38 - Five Minute Proposals 07:15 - Email Like You Mean It 13:39 - Centralized CRM Wins 17:14 - Offboarding Reviews Blogging 18:54 - Automation Balance 21:08 - Next Services To Automate 24:33 - Timing Inquiries And 60 Days 30:17 - Favorite Parts And GPTs
Mentioned in this Episode Systems in Session: coliejames.com/systems Email Like You Mean It: coliejames.com/email-like-you-mean-it
Connect with the Guest Website: jordancraigmedia.com Instagram: instagram.com/jordancraigmedia
Session vs Pixieset vs a Full CRM: What Photographers Actually Need
09/06/2026 | 18 mins.
Is Session or Pixieset enough for your photography business? With CRM prices going up, more photographers are asking whether they really need a full CRM — or if they can get by with the tools they're already paying for. In this episode, I'm taking an honest look at both Session and Pixieset Studio Manager: what they actually do well, where they fall short, and the one thing neither of them can give you — control over your client's timeline. I'll share stories from two photographers who moved out of Pixieset into Dubsado, including one who went from 90 minutes to five minutes on the proposal phase alone. And I'll tell you exactly who Session is actually right for — because the answer might surprise you. If you've been wondering whether a full CRM is still worth it, this episode is for you.
Links mentioned: Session vs full CRM comparison → [coming soon] Follow-up emails episode → coliejames.com/follow-up-emails-example/ Jordan's episode → coliejames.com/dubsado-for-wedding-photographers-jordan-craig/ Best CRM for Photographers → coliejames.com/best-crm-for-photographers Systems in Session → coliejames.com/systems
How Dubsado Grew to 30,000 Users Without Venture Capital with CEO Becca Berg
04/06/2026 | 55 mins.
What happens when the mistake of a missed photo shoot turns into one of the most beloved CRMs for creative entrepreneurs? In this episode, I sat down with Dubsado co-founder and CEO Becca Berg to talk through building a SaaS company from scratch with her husband Jake, scaling to 30,000+ users, and why staying self-funded has shaped every decision they’ve made over the last decade. We talked about the real beginnings of Dubsado, the growing pains behind CRM development, why certain features take time, and what’s actually coming inside Dubsado 3.0. Becca also opened up about one of the hardest moments in Dubsado history and how trusting her gut changed the way she leads the company today. If you’ve ever wondered what goes on behind the scenes of the CRM so many creatives rely on every day, this episode is for you.
Find It Quickly 00:38 - Meet Becca 03:50 - Dubsado's Origin Story 08:10 - Building the First CRM 10:13 - Customization as the Edge 12:02 - First Customers and Milestones 17:46 - Growing the Team 22:42 - Why Stay Self Funded 25:20 - Why Features Take Time 29:25 - Scheduling Feedback to Release 31:24 - New Form Builder Vision 34:10 - Subscriptions and Checkout 36:53 - Beyond Project Based Work 42:25 - Hard Lessons and Payments Crisis 45:24 - Stripe Migration and Sub Accounts 48:53 - Dubsado 3.0 Sunset Timeline
May was rough, no solos were recorded, but June is a new month! In this episode I am giving you 5 updates, 4 business and 1 personal, to get these solo episodes back on track 👏🏽
Links Mentioned: coliejames.com/sales to join my FREE training on June 18th at Noon MT/2pm ET where I will walk you through eliminating the sales calls you hate and/or don't have time for coliejames.com/experience to see the new version of Email Like You Mean It coliejames.com/waitlist to grab the two bonuses available for Systems in Session Q3 Dubsado Workflow Series (6 of the 14 blog posts I wrote in May) SEO & Grow Sprint with Brittany Herzberg
Retention Marketing Strategies That Keep Clients Coming Back with Zoë Dew
21/05/2026 | 47 mins.
What if the easiest sales you’ll ever make are from people who already know, trust, and love your work? In this episode, I’m joined by Zoë Dew to wrap up my sales series with one of the most overlooked strategies in business: retention. We’re diving deep into why so many service providers leave money on the table after delivering a service, and how building intentional relationships with past clients can completely change the way you market and sell. We talk about the power of one-to-one outreach, why follow-up is your responsibility as a business owner, and how to stop chasing cold leads when warm opportunities already exist inside your business ecosystem.
Find It Quickly 03:59 - Why Past Clients Matter 06:41 - Stop Being Passive 11:19 - Make Outreach a System 13:44 - Follow Up Like a Pro 15:52 - Broadcast vs One to One 23:08 - What Retention Really Means 25:28 - Check Ins Build Trust 36:53 - Warm Beats Cold Leads 43:13 - Beyond Paying Clients 45:31 - Where to Find Zoe
Mentioned in this Episode: Episode 266: Stop Chasing Vanity Metrics: The 4 Habits That Actually Grow Your Business with Zoë Dew
Connect with Zoë Website: zoedew.com Instagram: instagram.com/zoerdew
About Business-First Creatives: Client Experience & Systems for Service Providers
About Business-First Creatives: Client Experience & Systems for Service Providers
About Business-First Creatives: Client Experience & Systems for Service Providers
Business-First Creatives is a podcast for photographers and creative service providers who want to build a profitable, sustainable business without drowning in admin work, client experience chaos, or systems that let you down.
This show delivers clear, actionable conversations around marketing, CRM workflows, client communication, Dubsado and Honeybook automation, Airtable systems, and workflow strategies, giving photographers and creative entrepreneurs the systems that scale, operational clarity, and strategic, human-first client experiences they need to build streamlined, referral-worthy business operations that don't require working 24/7.
If you're tired of babysitting your inbox, chasing down contracts, or watching your workflows break the moment you look away, this show will help you move beyond "figuring it out as you go" and toward a creative business that brings you joy and a paycheck.
This podcast provides answers to questions like:
How do I automate my client journey without losing the personal touch?
What CRM workflows do photographers and creative businesses need?
How can I use Dubsado or Honeybook to streamline my client experience?
What systems do photographers need to save time and deliver exceptional client experiences?
How do I reduce admin time in my creative service business?
Why do my workflows keep letting me down (and how do I fix them)?
How can I build a profitable creative business that brings me joy and a paycheck?
What's the best way to communicate with clients throughout their journey?
How do I create systems that work even when I'm not babysitting them?
How can I map my client journey to convert more inquiries into bookings?
Hosted by Colie James, a Dubsado Certified Specialist, Honeybook Educator, and Workflow and Automations Guru with 10+ years helping creatives systemize their businesses—this show delivers practical, no-BS guidance for photographers and creative entrepreneurs who are ready to streamline their client journey, automate their operations, and make money from their craft.
If you're done dropping balls and ready to build a business-first creative operation with systems that scale, you're in the right place.
Find out more about Systems in Session ➡️ https://coliejames.com/systems-in-session
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