Creative Outcomes

RFPs: necessary evil… or optional trap?

In this episode of Creative Outcomes, Craig Baldwin breaks down how agencies should think about RFPs (Requests for Proposals) - why clients issue them, what red flags to watch for, and how to qualify opportunities before your team burns weeks of time chasing work you were never going to win.

If your agency is relying on RFPs as your primary growth channel, this conversation is your wake-up call: RFPs can drain your sales and marketing momentum, compress margins, and create “busy work” that feels productive but doesn’t move revenue.

You’ll learn:

- The 3 main reasons clients send RFPs (and what each one signals)

- The #1 deal-breaker: no access to decision makers

- How to estimate the real cost of responding (and why tracking matters)

- A simple litmus test to decide whether to respond or walk away

- How “pipeline anxiety” leads teams to chase the wrong work

- Why having an internal RFP qualification point-of-view is a competitive advantage

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TIMESTAMPS:

00:00 — Why RFPs feel brutal

01:10 — Why clients put out RFPs

03:10 — The “busy work” trap in biz dev

04:35 — Quick fit check (use AI + spot dealbreakers)

05:30 — The biggest red flag: no decision-maker access

06:45 — Estimating true effort + internal cost

07:55 — Why we still say yes (FOMO + pipeline anxiety)

09:00 — Build internal win/loss “house knowledge”

10:10 — Track the cost (hours, roles, rough math)

11:40 — Litmus test: cold vs warm + relationship strength

12:50 — Litmus test: is it work you want (and can win)?

13:55 — Litmus test: delivery risk + subcontracting reality

15:05 — Create an RFP qualification POV (filter faster)

16:20 — If you’re living on RFPs, what broke upstream?

18:05 — Use RFPs to show how you think (challenge the client)

If you run a marketing or creative agency, you’re probably facing one of two problems:

• You’re not making the profit you expected

• Your team feels slammed… but you suspect there’s excess capacity

And somewhere along the way, someone told you: “You need time tracking.”

In this episode, Ryan Watson (Partner at Upsourced) gives the definitive overview of how agency owners should think about time tracking - why it matters, how to implement it properly, and how to avoid the common mistakes that make teams resent it.

You’ll learn:

- Why gross margin is the whole ball game

- The “Margin Triangle” framework (Project Margin + Utilization)

- Why most scaled agencies track time (and why skipping it is the exception)

- How to roll out time tracking without destroying morale

- Why time tracking should not be used as a performance management tool

- The daily and weekly process that actually works

- How to create buy-in (and avoid garbage-in, garbage-out data)

- Why alignment + process matter more than software

Time tracking isn’t about micromanagement. It’s about building a profitable, scalable, sustainable agency.

If you want better margins, better utilization, and better decisions - this episode is for you.

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TIMESTAMPS:

00:00 The 2 Problems Most Agencies Face

01:31 Gross Margin Is the Whole Ball Game

02:28 The Margin Triangle: Project Margin + Utilization

04:34 Do You Really Need Time Tracking?

06:43 Why Most Scaled Agencies Track Time

07:08 Why Time Tracking Fails (Alignment & Buy-In)

09:36 What NOT to Do: Don’t Weaponize Utilization

14:16 Process Over Software

15:33 The Right Cadence: Daily Tracking, Weekly Compliance

19:56 Close the Loop: Use the Data or Lose Buy-In

21:32 The Formula for a Profitable, Sustainable Agency

“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

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.

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

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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.

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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.

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

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

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!