Creative Outcomes

Upsourced
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Welcome to Creative Outcomes. If this is your first time here, we work with nearly 100 digital and creative agencies, and we bring you the inside scoop, and spill the tea for what makes the best - the best.

  1. Compensation Structures for Partners

    2025-11-20

    Compensation Structures for Partners

    “How much should I be paying myself?” If you’re an agency owner or partner, you’ve probably asked that question more than once. In this episode of Creative Outcomes, Upsourced partners Ryan Watson and Craig Baldwin break down what partner compensation should look like in a modern agency. We get into: - How to think about “the maximum you can pay yourself” without starving the business - Why cash reserves and forecasting are critical before you touch distributions - The difference between S corps and partnerships when it comes to salary vs. distributions - How often to run profit distribution calculations (monthly vs. quarterly vs. annually) - Why borrowing from client prepayments or lines of credit to “pay yourself” is a huge red flag - The tough question: “At what point am I better off just getting a job?” - What it really means to be a partner and why sloppy equity promises are so dangerous If you’ve ever wondered whether you’re paying yourself enough, too much, or in the wrong way, this episode is for you. Subscribe for more conversations on agency finance, profitability, and building a business that actually pays you what you’re worth. Timestamps: 0:00 – Intro 1:10 – What do we mean by “partner compensation”? 3:45 – How much should I actually pay myself? 7:00 – Cash reserves and distributions 9:30 – S corp vs. partnership: how structure changes comp 17:20 – How often should I take profit distributions? 19:40 – Basis, loans, and why “extra cash” might not be profit 28:00 – When your business isn’t paying you enough 34:30 – Partner dynamics, equity, and bad cap tables

    40 min
  2. Pricing Models That Protect Your Margin

    2025-11-20

    Pricing Models That Protect Your Margin

    Most agencies say they want “value-based pricing.” Few actually do it—fewer do it well. In this episode, Craig Baldwin, Partner at Upsourced, breaks down the real-world pricing models agencies use (time & materials, fixed fee, retainers/subscriptions, outcome/value-based, hybrids) and how to choose what protects margin and manages risk. The goal isn’t a perfect model; it’s a consistent 50%+ project/client margin and a healthier mix of recurring revenue so you’re not living project-to-project. You’ll learn: - The core pricing models and when they shine (or sink you) - Why true value-based pricing is rare—and risky—without data - Hybrid structures that share upside while capping downside - How recurring revenue creates a floor (and why projects set your ceiling) - The only metric Craig cares about: reliable margin TIMESTAMPS: 00:00 Intro 01:00 The big three: time, deliverable, or outcome 04:10 Time & Materials (incl. cost-plus) 05:54 Fixed-fee/project pricing—scope risk & expectation creep 08:14 Retainers & “subscription” models (what’s the real difference?) 09:46 What strict value-based pricing actually means 12:00 Hybrid pricing (base + performance) 13:00 Other models: barter, equity—why they usually disappoint 17:24 Productized vs. bespoke retainers 19:24 Project vs. recurring revenue (floor vs. ceiling) 20:55 The hype vs. the practice of “value-based” 24:54 Yes, you’ll still estimate time under the hood 26:45 Choosing what fits your strengths 28:37 Margin targets and diagnosing shortfalls 29:40 Wrap & how to get in touch Links: Work with Upsourced: www.upsourcedaccounting.com Email Craig: cbaldwin@upsourcedaccounting.com If this helped, hit Subscribe—new episodes on building durable, profitable agencies.

    29 min
  3. Playing Business vs. Running a Business: The Brutal Truth for Agencies

    2025-11-20

    Playing Business vs. Running a Business: The Brutal Truth for Agencies

    Are you busy all day—but not moving the ball? Ryan Watson and Craig Baldwin (Partners at Upsourced) break down “playing business”: the activities that look productive but don’t create revenue, profit, or durability. Learn the red flags (overspending ahead of growth, shiny‑tool chasing, coach‑collecting, RFP lotteries, acquisition daydreams) and the habits of winning agencies (focus, thrift, deputies, account farming, and clear positioning). What you’ll learn: - Why “hire when it hurts” protects margins - Process is greater than tools (and when software actually helps) - How to keep less than 50% of annual revenue from existing clients - The mindset behind 30–35% net‑margin agencies - “Do well to do good”: profit powering purpose TIMESTAMPS: 00:00 Intro & why “playing business” matters 07:50 Symptom #1: Spending ahead of growth; “hire when it hurts” 13:20 Playbooks & proxies vs. doing the work 14:20 Symptom #2: Shiny‑tool chasing (software ≠ process) 17:35 Symptom #3: Raising capital & M&A daydreams 24:05 Symptom #4: Coach‑collecting and abdicating judgment 27:00 Symptom #5: Pipeline neglect; dangers of RFP lotteries 31:00 Behavior #1: Deputies, swim lanes, and collaboration rhythms 33:00 Behavior #2: Ruthless focus; time as the scarce resource 37:00 Behavior #3: A clear calling card/positioning 38:30 Behavior #4: Account management are greater than new logos 42:00 Behavior #5: Thrift and needs‑based spending 46:30 Mission vs. profit: “Do well to do good” 51:40 Wrap & key reminder: identify candy vs. nutrition Subscribe to our channel for more insights!

    53 min
  4. Why This Agency Became a Worker-Owned Co-Op - Big Duck’s Story

    2025-11-20

    Why This Agency Became a Worker-Owned Co-Op - Big Duck’s Story

    What happens when an established creative agency transitions into a worker-owned co-op? In this episode of Creative Outcomes, Craig Baldwin sits down with Farra Trompeter, Co-Director and Worker-Owner at Big Duck, to explore: - Why Big Duck made the leap to a cooperative model - The cultural and financial shifts that came with it - How co-op ownership changes business development and client relationships - Lessons for agencies looking to build more sustainable, mission-driven teams If you’ve ever wondered about alternative ownership structures—or how to empower your team with true agency—this episode is a must-listen. Subscribe to our channel for more!

    46 min
  5. Building an Agency with Purpose (and Staying Profitable) - The Wide Eye Story

    2025-11-20

    Building an Agency with Purpose (and Staying Profitable) - The Wide Eye Story

    Ben Ostrower, founder and CEO of Wide Eye, joins us to share the origin story of his agency — from freelancing out of his kitchen to building a nationally recognized creative studio for progressive causes. We talk about: - What it takes to build a values-driven agency - How Wide Eye chooses mission-aligned clients - Balancing creative integrity with business growth - The evolution from solo freelancer to leading a purpose-fueled team Whether you're starting your own creative shop or rethinking your agency’s direction, Ben’s journey offers a grounded look at what it really takes to build with conviction. Don’t forget to subscribe for more conversations with creative agency leaders.

    40 min
  6. Account Manager vs. Project Manager: What’s Right for Your Agency?

    2025-11-20

    Account Manager vs. Project Manager: What’s Right for Your Agency?

    Should your agency hire an Account Manager or a Project Manager? Or both? In this episode of Creative Outcomes, we break down the crucial differences between AMs and PMs — and why getting this structure right can be a game-changer for your agency’s profitability, client satisfaction, and team sanity. We cover: ✅ Why creative agencies often blur the lines between AM and PM ✅ The financial implications of misaligned roles ✅ How to structure roles for scale and efficiency ✅ Utilization, comp strategy, and margin impact ✅ When (and how) to transition client relationships from sales to delivery Whether you're a small agency wearing multiple hats or scaling fast and thinking about team structure, this episode is packed with practical takeaways. 🎧 Listen in, and subscribe for more insights on growing your creative agency smartly. 🔗 Learn more at: https://upsourcedaccounting.com 📺 Subscribe for more agency finance tips: @upsourced

    43 min
  7. Why Your Sales Strategy Isn't Working (and the 6 month fix)

    2025-11-20

    Why Your Sales Strategy Isn't Working (and the 6 month fix)

    The brutal truth about agency sales that nobody wants to hear 🎯 Most agency owners are making the same expensive mistake: thinking they can hire their way out of a sales problem. In this deep-dive episode, we break down the real numbers behind successful agencies and reveal why the $10 million rule could save you from a costly hiring mistake. What you'll discover: - Why 70% of your revenue should come from existing clients - The exact percentage you should spend on sales & marketing (hint: it's not what you think) - When to hire your first full-time salesperson (spoiler: probably later than you planned) - The 6-12 month reality of sales hiring that most owners ignore - Why lead generation isn't your real problem Key Timestamps: 0:00 - The state of agency sales in 2025 5:23 - The 70/30 revenue split explained 12:04 - Sales vs. marketing budget breakdown 20:35 - The 3-month rule for sales activities 26:12 - Why founders must own sales until $10M 35:01 - Building a repeatable sales system Perfect for agency owners, consultants, and anyone running a professional services business who's tired of the feast-or-famine cycle. Subscribe to our channel for more insights

    43 min
  8. From All-Hands-On-Deck to Hands-Off Leadership: The Sans Serif Story

    2025-05-22

    From All-Hands-On-Deck to Hands-Off Leadership: The Sans Serif Story

    Join host Ryan Watson for an inspiring conversation with David Shultz, founder of Sans Serif, as he shares his remarkable entrepreneurial journey from near-bankruptcy to building a thriving design and marketing strategy firm. This episode dives deep into the realities of agency ownership, the psychology of entrepreneurial optimism, and the key decisions that transformed a struggling startup into a successful business. Key Themes: - Entrepreneurial Psychology: The blessing and curse of being an eternal optimist - Crisis Management: How to navigate financial struggles and dark moments as a founder - Team Building & Leadership Evolution: Learning to delegate and trust your team - Client Relationships: The power of treating clients as partners, not just customers - Industry Adaptation: Embracing AI and new technologies while maintaining human value - Specialization Strategy: Finding your blue ocean through niche expertise Timestamps: 00:00 - Introduction and guest background 01:58 - Founding story: From employee to entrepreneur 03:22 - The motivation to leave a safe job 04:42 - Taking the leap without guaranteed clients 07:33 - Early financial struggles and dark moments 12:35 - The conversation with his wife about quitting 15:56 - Understanding entrepreneurial optimism and its dangers 22:26 - Evolution of leadership role and delegation 29:07 - The secret to Sans Serif's success 34:00 - Lessons learned and what he'd do differently 35:43 - AI's impact on the creative industry 40:34 - Advice for starting an agency in 2025 This episode is essential listening for current and aspiring agency owners who want to understand both the challenges and rewards of building a creative business from the ground up. Subscribe to our channel for more insights!

    44 min
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About

Welcome to Creative Outcomes. If this is your first time here, we work with nearly 100 digital and creative agencies, and we bring you the inside scoop, and spill the tea for what makes the best - the best.

Information

  • Creator
    Upsourced
  • Years Active
    2022 - 2025
  • Episodes
    45
  • Rating
    Explicit
  • Copyright
    © Upsourced 2022
  • Show Website
    Creative Outcomes