Working With Designers

Kristin Silva and Jake Cooper dive into the realities of running a creative business—from strategic networking and portfolio challenges to marketing, sales, and client management. They reflect on local creative communities, the pitfalls of bad industry advice, and the tech gaps small businesses face. The conversation highlights the balance between strategy and execution, the evolution of design expectations, and the value of building habits, community, and sustainable creative practices.

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00:00 – Networking Events and Community Building

06:06 – The Value of Networking and Building Relationships

12:02 – The Importance of Strategic Networking

15:01 – Advice on Portfolio and Case Studies

27:12 – Balancing Depth and Simplicity in Portfolios

32:58 – The Gap in Tech Solutions for Small Businesses

39:03 – Rented vs. Owned Audiences in Marketing

50:59 – The Balance Between Creative Execution and Strategy

01:04:54 – Navigating Career Milestones and Creative Blocks

01:47:58 – Sales Strategies and Portfolio Management

Summary

In this episode, Jake and Kristin dive into the messy, meaningful side of client work—where strategy meets real talk. They unpack the importance of setting expectations early, owning the process, and leading clients with clarity and confidence. From subscription models and value-based pricing to design briefs and project pivots, they share hard-earned lessons from the trenches. It’s a candid conversation about when to push, when to listen, and why it’s up to us—the creatives—to steer the ship.

Takeaways

Here’s the deal: if you’re not leading your projects, your clients definitely will—and that’s how good work goes off the rails. This episode is a reminder that it’s on us, as designers, to set the tone, define the process, and hold the line. That means crystal-clear briefs, real talk about strategy, and pushing back when things get fuzzy. Subscription models? They’ll eat you alive without boundaries. Value-based pricing? Useless if you’re afraid to talk about risk. The takeaway? Take control, stay accountable, and stop waiting for permission to lead.

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00:00 — Intro

04:13 — Navigating Client Relationships and Design Tests

08:46 — Subscription Models: Pros, Cons & Pitfalls

15:00 — Strategy vs. Execution: Finding the Balance

28:08 — Why Design Briefs Matter (More Than You Think)

38:30 — Client Communication: Say It Early, Say It Often

49:58 — Owning Accountability in Your Creative Business

56:48 — Value-Based Pricing: What It Really Takes

01:12:12 — Pricing Models and Managing Risk

01:24:00 — Setting Expectations (Before They Set You)

01:29:27 — Outro

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Keywords

creative business updates, managing client relationships, design process testing, design project workflows, subscription pricing for designers, retainer models for creative services, brand strategy implementation, client communication strategies, writing effective design briefs, educating design clients, professional development for designers, creative project management, accountability in client work, creative business strategy, value-based pricing for creatives, managing pricing risk, delivering impactful design, self-reflection in creative work, setting client expectations, boundaries in design projects, design feedback and iteration, scope creep management, onboarding design clients, creative services pricing models

Summary

In this episode of 'Working with Designers', hosts Jake Cooper and Kristin Silva engage with Sean Clancy and Elina Picciocca, co-founders of Space Out Design. They discuss the realities of creative partnerships, the journey of starting a design studio, navigating roles and responsibilities, client relationships, and the challenges of transitioning to full-time freelancing. The conversation emphasizes the importance of financial strategies, mental health, and the design of one's life in the creative industry. In this conversation, Elina Picciocca, Jake Cooper, and Kristin Silva discuss the intricacies of managing a creative business, focusing on project processes, time estimation, financial goals, and the balance between work and personal life. They share insights on overcoming burnout, the transition from designer to business owner, and the importance of community support. The discussion also touches on productivity strategies, the role of music in creativity, and the necessity of setting boundaries to maintain a healthy work-life balance.

Takeaways

• Creative partnerships can enhance productivity and creativity.
• Navigating roles in a partnership is essential for success.
• Client relationships require clear communication and boundaries.
• Taking the leap into full-time freelancing is a significant decision.
• Financial strategies are crucial for sustaining a freelance business.
• Mental health plays a vital role in the creative process.
• Underestimating project hours can lead to burnout.
• It's important to find a balance between work and personal life.
• Designing your life is as important as designing for clients.
• Having a safety net can ease the transition into freelancing. We start breaking down every single project.
• We overestimate our ability to work fast.
• You have to do research and talk to the client.
• You have to have that kind of awareness.
• We figured out if we put our goal, we complete the goal on 70%.
• We start structured, but we spent like we weekend at least at the week we not work.
• You have to love the graphic design.
• Don't undercharge, price is self-perfectly.
• We went year and a half without day off.
• We start doing boundaries.

Chapters

00:00 Creative Partnerships and Business Beginnings

10:27 Balancing Full-Time Jobs and Entrepreneurship

15:03 The Dynamics of a Business Partnership

36:47 The Intersection of Law and Design

40:36 Taking the Leap: Transitioning to Full-Time Freelancing

54:48 Finding Balance: Mental Health and Work

59:54 Designing Your Life: The Business of Freelancing

01:15:01 Navigating Burnout in the Creative Industry

01:25:04 Finding Creative Flow and Productivity Hacks

01:48:07 Wrap-Up and Outro

Learn more

Spaceout Design

spaceoutdesign.com

Studio Quiche

studioquiche.com

Jake Cooper Design

jakecooperdesign.com

Working With Designers

workingwithdesigners.com

Keywords

creative partnerships, design studio, freelancing, client relationships, business strategies, design process, mental health, collaboration, entrepreneurship, design industry, project management, creative process, time estimation, financial goals, work-life balance, burnout, design business, pricing strategies, community support, productivity

This episode of Working With Designers explores the complexities of niching as a creative professional, including when it's beneficial, when it’s limiting, and how to balance specialization with flexibility. Jake Cooper and Kristin Silva break down real-world experiences, industry misconceptions, and strategies for making the best decision for your business.

00:00 – Weekend Reflections

03:03 – The Challenge of Niching

08:23 – Why Audience Focus Matters

13:30 – Defining Niching & Its Benefits

18:48 – Personal Experiences with Niching

24:05 – From Niche to Portfolio Building

29:12 – Specialization vs. Generalization

38:36 – Strategy & Visual Design Reflections

50:15 – Understanding Value in Design

54:20 – Niche Marketing & Client Education

01:03:54 – Defining Your Unique Value

01:14:05 – The Portfolio Dilemma

01:16:22 – Branding vs. Marketing

01:28:50 – Final Thoughts on Niching

Summary

In this conversation, Jake and Kristin explore various themes related to design, branding, and client relationships. They discuss the importance of mental health in business, the delicate balance between branding and marketing, and the challenges of educating clients about their needs. The conversation also touches on the impact of social media, particularly TikTok, on content creation and the significance of community engagement for business growth. In this conversation, Jake Cooper and Kristin Silva explore the importance of community and collaboration in creative fields, the influence of reading on creativity, and the significance of archiving knowledge. They discuss the dynamics of creative partnerships, the challenges of client expectations, and the necessity of intentional design. The dialogue emphasizes the need for experimentation and understanding the intricacies of the design process while navigating the complexities of client relationships.

Chapters

00:00 Intro

03:51 The TikTok Ban of 2025

07:55 Choosing Between Marketing and Branding

26:04 Meeting Clients Where They Are

48:46 The Power of Word of Mouth Marketing

50:04 The Influence of Reading on Creativity

57:06 Note-Taking and Information Management

01:03:27 Finding Inspiration Beyond Digital Media

01:11:06 Creative Collaboration and Project Dynamics

01:18:49 Design Tests: Fair or Predatory?

01:29:32 The Challenges of Emerging Designers

01:44:04 Outro

In this episode of 'Working with Designers', hosts Jake Cooper and Kristin Silva discuss the intricacies of branding, client management, and the challenges faced by designers in the creative industry. They explore how to determine the branding needs of clients based on their business stage, the importance of establishing a strong brand foundation, and strategies for effective networking and finding the right design talent. The conversation emphasizes the evolving nature of branding and the necessity for ongoing investment and review to ensure long-term success. In this conversation, Kristin Silva and Jake Cooper discuss the intricacies of design and branding, emphasizing the importance of selecting the right designer, the necessity of a design system, and the role of brand guidelines in establishing a strong visual identity. They explore how to effectively use these guidelines, the journey of starting a branding project, and provide valuable advice for aspiring designers and business owners.

Chapters

00:00 Intro

11:13 How much branding do I actually need?

32:03 Investing in Branding: Where to Start?

36:52 Where to find designers

50:02 Understanding Brand Guidelines

01:06:12 Collaborative Workshops for Brand Guidelines

01:06:16 Where to Start Your Branding Journey

01:18:09 Advice & Action Items

01:29:59 Outro

In this episode of 'Working with Designers', Kristin Silva and Jake Cooper explore the multifaceted value of design in business. They discuss the challenges of quantifying design impact, emphasizing that design is not just about aesthetics but also about creating systems that enhance efficiency, retention, and revenue. The conversation delves into the importance of understanding metrics, the internal and external impacts of design, and the significance of building strong client relationships. They also touch on the evolving landscape of design in the context of economic changes and the role of AI in shaping future design standards. In this conversation, Kristin Silva and Jake Cooper explore the impact of design and branding through the lens of AI, personal success stories, and case studies of Jaguar and Liquid Death. They discuss the importance of trusting one's instincts in business relationships, the insecurities that AI can reveal in individuals, and the measurable impacts of design on sales and branding. The discussion also delves into the bold rebranding efforts of Jaguar and the successful marketing strategies of Liquid Death, highlighting the emotional and quantitative aspects of branding.

Chapters

00:00 Intro

05:19 The Value of Design in Business

10:18 Design as a System

15:14 Efficiency, Retention, and Revenue

20:09 Metrics for Evaluating Design Impact

25:08 Subjectivity in Measuring Success

33:49 Measuring Success: Leading vs. Trailing Metrics

34:20 The Importance of Inputs in Business

36:40 Navigating Business Pressures and Projections

40:21 Market Sensing and Business Adaptation

43:12 The Impact of AI on Job Security

50:21 Real-World Examples of Design Impact

58:03 Branding Case Studies: Jaguar vs. Liquid Death

01:00:38 The Impact of Jaguar's Rebranding

01:04:46 Consumer Reactions and Brand Identity

01:07:53 Jaguar's Shift to Ultra Luxury

01:14:07 Liquid Death: A Case Study in Branding

01:20:37 Measuring Impact and Audience Engagement

01:30:26 Outro

We're letting our hair down! This week, we switched things up! Stay tuned, dive in, and give it a listen if you’re in the mood for a casual conversation about navigating change.

We cover a mix of topics, like conflating ones identity with ones work, using social media with a healthy dose of skepticism, and the post-election energy that’s shaping our mindset as we look toward 2025. We also chat about finding motivation, building healthy habits in today’s digital whirlwind, and even picking up that paintbrush to spark creativity.

We recorded this episode fresh after a busy month of societal buzz to give you an honest glimpse of who we are—not just as designers, but as people.

We hope you enjoy this laid-back episode!

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00:00 — Lead-in

03:03 — The Evolution of Personal Branding

05:57 — Social Media's Role in Community Building

08:58 — Navigating Political Discourse and Identity

14:58 — The Challenge of Nonprofit Work

18:02 — Conflating Identity with Work

22:16 — Burnout and the Need for Creative Recharge

26:34 — Finding Balance in Consumption and Creation

35:41 — The Balance of Input and Output in Creativity

37:57 — Navigating Client Relationships and Personal Identity

39:58 — Insights from Rick Rubin's Creative Philosophy

42:00 — The Feast and Famine Cycle of Freelancing

45:41 — The Challenge of Money and Creativity

49:31 — The Role of Platforms like Fiverr and Upwork

56:35 — Future Directions and Collaborative Projects

58:05 — Outro

This is truly an introduction, and we couldn’t be more thrilled to share this space with fellow creatives and business owners alike. So, let’s dive right into what you’ll be listening to. We’re calling it… Episode 0—a humorous yet meaningful way to commemorate the true beginning of this journey.

Here’s a quick, timestamped guide:

0:00 — Introductions
5:52 — Diving in!
8:12 — What is branding?
14:00 — It isn't what you think it's what they think...
22:22 — How much brand do you need right now?
28:04 — Why is branding with intention important?
35:50 — How do you handle facing fear (choosing a direction and sticking with it)
45:37 — "Where brand ends and design begins..."
48:33 — How does one get started?
1:02:59 — Ending "take action notes"