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“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
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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: [email protected]
If this helped, hit Subscribe—new episodes on building durable, profitable agencies.
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Saknas det avsnitt?
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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!
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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!
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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.
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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
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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
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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!
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In this episode of Creative Outcomes, we tackle a challenge many businesses face: the dreaded mid-year sales lull.
If your pipeline is looking empty and your revenue targets seem increasingly out of reach, this episode is for you.
Our host, Craig Baldwin, Partner at Upsourced, shares practical, actionable strategies to jumpstart your sales pipeline, including:
- Proven tactics to motivate your sales team when they need it most
- How to approach price increase conversations effectively - What to do when deals keep getting pushed or budgets get pulled
- Where to find quick wins when your back is against the wall
- How to distinguish between market problems vs. internal issues
Remember: outcome lags effort by about three months. What you do today will impact your results in August, so don't wait until you're desperate to take action! Subscribe to our channel for more insights.
Timestamps:
00:00 - Introduction and episode overview
01:31 - Controlling what you can in sales
03:20 - Strategies to motivate your sales team
05:00 - The three-month lag principle
06:35 - Three sources for quick revenue wins
11:00 - Why marketing campaigns aren't the quick answer
15:53 - Navigating price increase conversations
17:26 - What to do when deals stall or budgets get pulled
19:39 - Moving beyond "hope and pray" strategies
23:13 - Finding your path forward 24:42 - Closing thoughts and contact information
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In this episode of Creative Outcomes, Craig Baldwin sits down with Prentice Howe, owner of Door No. 3, for a candid conversation about the realities of running a creative agency.
Prentice shares a pivotal moment in his career - sneaking into his own office at midnight to steal his own financial records - that became a turning point in how he approached business leadership.
From his transition from award-winning creative director to agency owner, Prentice reveals the challenges of managing a team, maintaining motivation, and staying true to your values even when it means walking away from money.
This conversation tackles:
0:00 - Introduction and background
13:35 - The financial breaking point that changed everything
17:20 - Building and empowering a leadership team
21:50 - Maintaining motivation after a decade of ownership
30:10 - Embracing AI in the agency model
36:15 - The value of outside perspective
40:25 - Standing by your values when money is on the line
If you're an agency owner or creative leader feeling the weight of responsibility, this conversation offers both practical insights and the comfort of knowing you're not alone in your struggles.
Subscribe to our channel for more insights!
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In this episode of the Creative Outcomes podcast, host Craig Baldwin speaks with Garrett, Spencer, and Tucker, the partners behind Alright Studio.
They share their journey from freelancers to running a 10-person creative agency in Brooklyn, discussing the evolution of their business model, their approach to team building, financial challenges, and how they've learned to trust their intuition while building something meaningful.
TIMESTAMPS:
00:00 - 01:10 - Introduction to the podcast and Alright Studio partners
01:10 - 06:00 - The genesis of Alright Studio and partnership formation
06:00 - 10:30 - Current state of Alright Studio and their service offerings
10:30 - 14:30 - What makes Alright distinctive and their unique approach
14:30 - 19:00 - Financial management challenges and finding upsource
19:00 - 26:45 - How accounting partnership changed their business approach
26:45 - 33:40 - Team growth, studio culture, and organizational philosophy
33:40 - 41:00 - Business ownership challenges and finding validation
41:00 - 48:30 - Long-term perspective, future outlook, and closing thoughts
For more, contact us: https://www.upsourcedaccounting.com/contact-us?utm_campaign=Alright_Podcast
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🔍 M&A Secrets: 10 Surprising Truths from Two-Time Sellers
From shocking valuation differences to the truth about strategic acquisitions, discover what really happens when selling your business.
Key revelations:
- Valuations aren't as scientific as you think
- Even big companies are figuring it out as they go
- Your negotiating power is stronger than you realize
- How net working capital can shift your final payout
- The reality of working under new ownership
Whether you're considering selling your business or just curious about M&A, this candid discussion pulls back the curtain on what really happens behind closed doors.
Learn from those who've been through it twice!
Want help navigating your M&A journey? Connect with our experienced team at Upsourced. https://www.upsourcedaccounting.com/contact-us?utm_campaign=M&A_Podcast
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Learn the 5 financial metrics your agency should be tracking to unlock profitable growth.
In this session with Upsourced's Ryan Watson and Agency Builders' Logan Lyles, you'll learn:
- The 5 financial metrics successful agencies get right (from Upsourced’s analysis of dozens of agency clients)
- The Hierarchy of Financial Needs to identify the right financial metric to prioritize at your agency's current stage
- The 3-part framework known as the Margin Triangle (key to getting a handle on your agency’s gross margin)
If you have questions, please contact us for more: https://www.upsourcedaccounting.com/contact-us?utm_campaign=ABWebinar
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Join us in this episode of Creative Outcomes as Natalie from Fifth Third Bank's Provide division breaks down everything you need to know about SBA loans.
In this must-watch podcast, discover:
✅ When to consider an SBA loan
✅ Key qualification requirements
✅ How to use SBA loans for business growth
✅ Acquisition financing strategies
✅ Avoiding common loan application mistakes
Perfect for entrepreneurs, small business owners, and anyone looking to understand business financing options!
For more, contact us: https://www.upsourcedaccounting.com/contact-us?utm_campaign=SBALoanPodcast
TIMESTAMPS:
0:00 - Introduction
1:00 - When to Consider an SBA Loan
2:20 - Documentation Requirements for SBA Loans
3:30 - Types of SBA Loan Use Cases
5:15 - SBA Loans: Strategic Growth vs Immediate Cash Needs
6:40 - SBA Loan Qualification Criteria
8:00 - Risks and Personal Guarantees in SBA Lending
9:25 - Handling EIDL Loan Repayment Challenges
12:15 - What to Avoid with SBA Loans
13:40 - SBA Loans for Business Acquisition
15:35 - SBA Loan Benefits Compared to Conventional Financing
17:05 - Steps to Explore SBA Loan Options
19:05 - Current Lending and M&A Market Trends
21:50 - Importance of Banker Relationships
23:50 - Closing Remarks
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In this episode, Anthony Armendariz, co-founder of Funsize, shares:
- The origin story of Funsize
- Inside look at Method Week
- their innovative quarterly program bringing teams together
- How they've built a lasting design agency while balancing family business dynamics
- Their evolution from a 4-day workweek to a thriving two-division studio
- The power of reinvention and authentic company culture in agency life
- Anthony's vision for the future of design consulting and creative work
Perfect for agency owners, designers, and anyone interested in building sustainable creative businesses that put people first!
For more, contact us: https://www.upsourcedaccounting.com/contact-us?utm_campaign=FunsizePodcast
TIMESTAMPS:
0:00 - Introduction & Funsize Overview
3:42 - Working with Spouse/Family Business
6:31 - Previous Agency Experience & Lessons Learned
9:37 - Leadership Role & Company Culture
15:48 - Method Week Deep Dive
24:42 - Future Vision & Dreams for Funsize
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In this episode, former agency CEO and current consultant Chris DuBois shares his insights on developing the leadership skills needed to build high-performing, motivated teams.
Drawing from his experiences transitioning from an operator role to a consultancy, Chris discusses strategies for hiring the right people, managing through challenges, and fostering a dynamic agency culture that employees are excited to be a part of.
Learn how to become the type of leader your team wants to follow. For more, contact us: https://www.upsourcedaccounting.com/contact-us?utm_campaign=ChrisPodcast
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In this episode, Craig Baldwin interviews Karl Sakas, agency advisor and author of "Work Less, Earn More".
Karl shares insights on helping agency owners find balance, delegate effectively, and increase profitability.
Key topics include:
- The inspiration behind Karl's new book
- Frameworks for reducing owner involvement
- Balancing work reduction with agency growth
- Strategies for high-value time management
- Overcoming challenges in delegating responsibilities
- Using the "advanced retrospective" tool for goal-setting
Learn practical advice for optimizing your agency and achieving both personal and professional success.
Whether you're looking to scale, sell, or simply enjoy running your agency more, this episode offers valuable takeaways for creative business owners.
Book: Work Less, Earn More: How to Escape the Daily Grind of Agency Ownership (https://sakasandcompany.com/lp/work-less-earn-more-book/?utm_campaign=CreativeOutcomes)
Resources: Free agency advice from Karl Sakas (https://sakasandcompany.com/free-resources-for-agencies/?utm_campaign=CreativeOutcomes)
Free Template: Visualizing your ideal agency with an Advance Retrospective (https://sakasandcompany.com/using-advance-retrospectives/?utm_campaign=CreativeOutcomes)
LinkedIn: Connect with Karl Sakas on LinkedIn (https://www.linkedin.com/in/karlsakas/)
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Proven tips to master your financial and RevGen strategies at each stage of the agency life cycle.
Download The Agency Growth Roadmap: https://drive.google.com/file/d/11KeDnbqa9Z3-pWc37V0zlD--eVEYZ0vL/view?usp=drive_link
In this insightful conversation, we break down the four key stages of agency growth:
- Creating the Business (0-$1M)
- Building the Business ($1M-$3M)
- Growing the Business ($3M+)
- Scaling the Business ($10M+)
We dive deep into the challenges and opportunities at each stage, covering topics like:
- Overcoming the "cobbler's children have no shoes" problem
- Balancing short-term revenue needs with long-term growth
- The importance of time tracking and profitability analysis
- Developing repeatable revenue generation systems
- Creating organizational structures that support growth
- Professionalizing sales and marketing as you scale
Whether you're just starting out or looking to take your agency to the next level, this episode offers valuable insights and practical strategies for success. For more, contact us: https://www.upsourcedaccounting.com/contact-us?utm_campaign=Agency-Growth-Roadmap-Podcast
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This episode of Creative Outcomes tackles the important topic of late accounts receivable (AR) for creative agencies.
Ryan Watson and Ashley Vaughn dive deep into strategies for preventing and collecting late payments from clients.
They discuss the importance of having clear payment policies and upfront communication with clients about AR processes.
Tune in to learn more! For more, contact us: https://www.upsourcedaccounting.com/contact-us?utm_campaign=Aged-AR
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Learn how to find and get recurring revenue for your creative agency or services business.
Craig Baldwin from Upsourced joins to discuss:
📈 The benefits of recurring revenue like predictability, higher valuations, and improved financial health
🤺 Balancing project-based "boom" revenue with recurring "bus" revenue
💰 Specific ways to add recurring revenue streams like support/maintenance, package deals, staff augmentation, and retaining AOR status
⚖️ The impact recurring revenue has on M&A valuations
🎯 Evaluating your services and capabilities to uncover recurring revenue opportunities
💭 Why there's no silver bullet - it takes experimentation to find the right recurring model
Recurring revenue reduces risk and provides stability for agencies and creative services firms. Get practical tips on adding more predictable revenue to your business.
- Visa fler
