🎙️ Guest: Karyn Scott, Fractional CMO & Founding Advisor at Fiat Advisors

🕒 Episode Length: ~30-32 minutes

Episode Overview

In this episode, we sit down with Karyn Scott, a seasoned Fractional CMO who has worked with some of Silicon Valley’s biggest names, including Salesforce, CloudSpot, and Cisco. Karyn shares how fractional leadership is reshaping executive roles, what it means for companies looking to scale efficiently, and how AI is impacting marketing, leadership, and knowledge work.

She also dives into how senior leaders can monetize their expertise in the evolving job market—and what AI’s rapid acceleration means for professionals trying to future-proof their careers.

If you’re a senior leader navigating AI disruption, a marketing exec thinking about going fractional, or just someone trying to understand where AI is headed next, this episode is packed with insights you won’t want to miss.

What You’ll Learn in This Episode:

✅ What fractional leadership actually means—and how it differs from traditional executive roles

✅ Why some companies shouldn’t hire a full-time CMO (and when fractional makes sense)

✅ How AI is changing marketing, storytelling, and leadership—and what leaders should do now

✅ The biggest misconceptions about AI-generated content and how it affects branding

✅ Practical tips on how to monetize your expertise as a fractional leader

✅ Why networking is changing—and how to leverage your industry connections for new opportunities

✅ Karyn’s top lessons learned as a fractional executive (including contract & pricing advice)

Key Quotes from Karyn Scott:

💬 “AI is changing storytelling, but humans still connect with emotion. The best marketers will know how to blend both.”

💬 “A great fractional executive doesn’t just consult—they embed, execute, and create lasting impact.”

💬 “If AI can take over your job, you should be thinking about how to work with it, not against it.”

Resources & Mentions:

📌 Fiat Advisors – Karyn’s advisory firm

📌 LinkedIn – Karyn Scott – Connect with Karyn

📌 HyperWrite – AI for writing & content creation

📌 Runway ML – AI for creative teams

Where to Find Karyn:

📍 LinkedIn: Karyn Scott

📍 X (Twitter): @KarynScott

📍 Instagram: @KarynScott

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🚀 Stay tuned for more episodes on how AI is disrupting jobs and reshaping leadership!

Subscribe to our Substack at www.stuckpodcast.com
You can watch each episode on Youtube https://www.youtube.com/@areyoustuck

This show was produced by Rob Curtis, Jamal Stockton and Ximena de la Tijera

Building the Future of Work with Jacob Bank

Episode Overview

In this episode, we explore how AI is transforming work with Jacob Bank, CEO of Relay.app and former Gmail product leader. Jacob shares insights from his journey from startup founder to Google executive and back to entrepreneurship, offering practical advice on leveraging AI effectively in business.

Key Topics

• The importance of keeping humans in the loop with AI automation
• How company structures are evolving in the AI era
• Transitioning between startup and corporate environments
• Building successful businesses in an AI-first world
• Practical applications of AI for personal and business productivity

Key Takeaways

• AI works best when humans remain engaged in reviewing and guiding outputs
• Future companies may be smaller but more senior, with AI augmenting capabilities
• The path to entrepreneurship is changing with lower barriers to entry
• Success in the AI era requires authenticity and community building
• Starting with personal productivity use cases is an effective way to adopt AI

Practical Insights

• AI automation examples: 
  • Email and calendar management
  • Customer research and communication
  • Content creation and analysis
  • Automated reporting and documentation
  • Video and audio content production

Career Lessons

• The importance of staying close to actual work vs pure management
• How to maintain authenticity while leveraging AI tools
• Why company building is becoming less capital intensive
• The value of finding the right problem vs rushing to market
• Building trust and community in an AI-enabled world

Future of Work Predictions

• Companies will likely become smaller but more impactful
• Junior execution roles may decrease as AI handles basic tasks
• More emphasis on "player-coach" roles combining strategy and execution
• Multiple successful companies can coexist in the same space
• Growing importance of community and authentic connection

Guest Bio

Jacob Bank is the CEO of Relay.app, building AI agent infrastructure to help businesses automate workflows. Previously, he founded Timeful (acquired by Google) and led Gmail as Director of Product Management. His work has impacted over a billion users through AI-powered features in Gmail and Google Calendar.

Resources Mentioned

• Relay.app - AI automation platform
• LinkedIn - Follow Jacob for practical AI implementation tips
• Weekly "Build with Me" sessions - Live AI automation tutorials
• Recommended AI tools: 
  • Caption
  • HeyGen
  • Claude
  • ChatGPT

Contact Information

• LinkedIn: Jacob Bank
• Email: [email protected]
• YouTube: Relay.app channel

About Stuck

Subscribe to Stuck on Apple Podcasts, Spotify, or wherever you get your podcasts. Email us: [email protected] Produced by: Rob Curtis, Jamal Stockton, and Ximena de la Tijera

Subscribe to our Substack at www.stuckpodcast.com
You can watch each episode on Youtube https://www.youtube.com/@areyoustuck

This show was produced by Rob Curtis, Jamal Stockton and Ximena de la Tijera

Episode Overview

Meet Jan DAlessandro, who pioneered remote work at AOL in the 90s and now directs billions in corporate philanthropy at Pledge One Percent. Her story shows how lawyers can leverage their skills far beyond traditional practice into business development and social impact.

Key Topics

• How Jan invented working from home at AOL in the 1990s
• Transitioning from corporate law to business development
• Building win-win partnerships across tech, media and entertainment
• Creating sustainable corporate giving programs
• Navigating career transitions in times of uncertainty

Key Quotes

"I got to a point where I thought, I don't really care about the indemnity clause. And then I realized - you can't do this job anymore because somebody needs to care about that. And it wasn't me."

"Culture eats strategy for breakfast every day."

"As a lawyer, you're trained to think critically... to not take things at face value and see how you can turn it into something positive for both sides."

Practical Insights

• Use your legal training as a foundation for other roles: 
  • Critical thinking
  • Negotiation skills
  • Deal structuring
  • Understanding multiple stakeholders
• Look for opportunities to merge your professional skills with personal interests
• Consider how your expertise could apply to emerging fields like AI
• Focus on building win-win partnerships rather than just transactions
• Stay connected to what energizes you, even if it means changing roles

Key Lessons for Career Transitions

1. Be honest with yourself about what naturally energizes you
2. Look at what you spend your free time doing - there are jobs related to any interest
3. Focus on transferable skills rather than just industry experience
4. Don't underestimate the value of your professional training in new contexts
5. Consider how emerging technologies like AI create new opportunities in familiar industries

Guest Bio

Jan DAlessandro pioneered work-from-home practices at AOL in the 1990s before transitioning into business development roles at major tech companies. As head of Pledge One Percent's Equity Initiative, she's helped direct over $2.5 billion in corporate philanthropy. Her career spans law, tech, entertainment and social impact.

Resource Mentioned

• Marianne Williamson quote: "Playing small doesn't serve the world"
• Cheryl Sandberg's gratitude journaling practice
• The Innovator's Dilemma by Clayton Christensen

About Stuck

Subscribe to Stuck on Apple Podcasts, Spotify, or wherever you get your podcasts. Email us at [email protected]. Produced by Rob Curtis, Jamal Stockton, and Ximena de la Tijera.

Subscribe to our Substack at www.stuckpodcast.com
You can watch each episode on Youtube https://www.youtube.com/@areyoustuck

This show was produced by Rob Curtis, Jamal Stockton and Ximena de la Tijera

Episode Overview

In this episode, we explore how to have difficult conversations about money with family members, partners, and children. With expert guidance from financial therapist Aja Evans, we discuss setting boundaries, managing expectations, and dealing with the emotional baggage that comes with money talks.

Key Topics

• Having difficult money conversations with partners
• Setting and maintaining financial boundaries
• Managing money with kids and dependents
• Understanding your personal money story
• Dealing with guilt and shame around financial changes
• Building effective money systems

Key Takeaways

• Communication is crucial but needs to be handled thoughtfully - set the stage for important conversations rather than springing them on people
• Use "I feel" statements and center emotions when discussing financial changes
• Your money beliefs are shaped by your earliest experiences - understanding this helps navigate current challenges
• Setting boundaries isn't just about saying "no" to others - it's also about setting limits with yourself
• Be age-appropriate when discussing money with children
• Focus on experiences and long-term investing for kids rather than material goods

Practical Tips

1. For Money Conversations: 
   • Choose the right time and setting
   • Lead with emotions and personal experience
   • Give partners grace to process information
   • Use "I feel" statements
   • Avoid springing sensitive conversations without warning
2. For Building Money Systems: 
   • Start by understanding your feelings about money
   • Know what's coming in and going out monthly
   • Set up automated payments where possible
   • Check finances at least monthly (weekly preferred)
   • Use high-yield savings accounts for emergency funds
3. For Setting Boundaries: 
   • Communicate changes in financial situation clearly
   • Offer alternative ways to show love/support beyond money
   • Remember that people's reactions belong to them
   • Be prepared for initial negative responses
   • Focus on quality time over financial support

Recommended Resources

Books mentioned:

• "Finance for the People" by Paco de Leon
• "Get Good with Money" by Tiffany Aliche
• "Money Out Loud" by Berna Anat
• "I Will Teach You to Be Rich" by Ramit Sethi
• "The Simple Path to Wealth" by J.L. Collins
• "Feel Good Finance" by Aja Evans

Apps mentioned:

• Monarch Money (budgeting app)
• Copilot (financial tracking)

About Our Guest

Aja Evans is the President of the Financial Therapy Association and author of "Feel Good Finance." As a financial therapist, she helps people understand their relationship with money and develop healthier financial habits. Her work focuses on the intersection of money, relationships, and personal growth.

Connect with Aja

• Instagram: @AJAetherapy
• LinkedIn: Aja Evans LMHC
• Website: ajaevanscounseling.com
• Book: "Feel Good Finance" (available at independent bookstores via Bookshop.org)

Get in Touch

Have a question about navigating money conversations with family? Email us at [email protected] or send us a voice note.

Subscribe to Stuck on Apple Podcasts, Spotify, or wherever you get your podcasts.

Produced by Rob Curtis, Jamal Stockton, and Ximena de la Tijera

Subscribe to our Substack at www.stuckpodcast.com
You can watch each episode on Youtube https://www.youtube.com/@areyoustuck

This show was produced by Rob Curtis, Jamal Stockton and Ximena de la Tijera

You can watch on Youtube: https://youtu.be/ZFXwxoRNQCA

In this episode of Stuck, we explore the psychology of money with behavioral finance expert Brian Pasalich. As CEO of Behave Technology and trainer of over 1,000 financial advisors, Brian shares deep insights into how understanding your financial decision-making style is crucial for making successful life changes.

Brian breaks down the key differences between "analyzers" and "strategizers" in financial decision-making, explains why traditional financial planning often fails, and offers practical approaches for making financial decisions when budgets are tight. He explores how complementary styles in partnerships can be more valuable than alignment, and emphasizes starting with values and goals before making financial plans.

Key Takeaways:

• Understanding your decision-making style is more important than trying to change it
• Four key factors you can control: earn more, spend less, delay goals, or change goals
• Sometimes you need to "suck it up" to achieve longer-term goals
• The importance of aligning financial decisions with personal values

Special Offer: The first 10 listeners to send a voice note to [email protected] will receive a free financial decision-making style assessment.

Follow Stuck:
Website: www.stuckpodcast.com
 
Email: [email protected]

About Brian Pasalich: Brian Pasalich is CEO of Behave Technology and a behavioral finance expert who has trained over 1,000 financial advisors. He helps clients develop clear-headed approaches to financial decisions by understanding their underlying behavioral patterns.

Subscribe to our Substack at www.stuckpodcast.com
You can watch each episode on Youtube https://www.youtube.com/@areyoustuck

This show was produced by Rob Curtis, Jamal Stockton and Ximena de la Tijera

**We released two episodes back to back for launch. Episodes will be released weekly, Thursdays starting next week**

"From Tech Executive to Gym Owner: A Story of Reinvention"
with Angela Sudbury

Episode Overview
Follow the journey of a 25-year tech veteran who transformed her career by opening a fitness franchise, learning valuable lessons about entrepreneurship along the way.

Key Topics
- The journey from 25-year tech career to small business ownership
- How to evaluate and pursue the franchise model
- Using retirement funds strategically through ROBS
- Managing the transition when you're the primary breadwinner
- Building a business that aligns with personal values

Key Quotes
"I would sum it up with one word - liberating."
"When I'm uncomfortable with something, that usually means I don't have enough information."
"Quality of life and our kids were getting older... it was just a matter of kind of narrowing down options."

Practical Insights
- Franchise advantages for first-time business owners:
  * Built-in mentorship
  * Proven systems and processes
  * Marketing support
  * Pre-launch planning assistance

- Financial considerations:
  * ROBS (Rollover for Business Startups) structure
  * C-Corp requirements
  * Ongoing administrative costs
  * Tax implications

- Customer acquisition strategies:
  * Pre-sales requirements
  * Social media marketing
  * Lead management systems
  * Network activation

Guest Bio
Angela Sudbury spent 25 years in technology before making the leap to small business ownership. Today she owns and operates Alloy Personal Training in Salt Lake City, where she helps clients improve their overall health and quality of life.

Resource Mentioned
alloypersonaltraining.com/halliday

Life Lessons
- Trust yourself enough to explore options
- Get comfortable with being uncomfortable
- The power of grit in entrepreneurship
- The value of connecting with people

---

About Stuck
Subscribe to Stuck on Apple Podcasts, Spotify, or wherever you get your podcasts.
Email us: [email protected]
Produced by: Rob Curtis, Jamal Stockton, and Ximena de la Tijera

Subscribe to our Substack at www.stuckpodcast.com
You can watch each episode on Youtube https://www.youtube.com/@areyoustuck

This show was produced by Rob Curtis, Jamal Stockton and Ximena de la Tijera

Episode 1: Are You Stuck or Just Impatient? A Silicon Valley Coach's Guide to Career Change
with Dr. Christina Villarreal, Executive Coach (OpenAI, Slack, Apple)

Episode Overview
In this episode, we explore how to recognize when you're truly stuck versus temporarily frustrated, and the psychology behind making major career transitions.

Key Topics
- How to tell the difference between being stuck versus being impatient
- The role of identity in career transitions
- Managing the emotional journey of major changes
- Why community matters when making big moves
- Practical steps to start your transition journey

Key Takeaways
- Being stuck often manifests physically and emotionally before we consciously recognize it
- There's a difference between work purpose and personal purpose
- Change requires letting go of certain identities and expectations
- The importance of giving yourself time to explore and experiment
- Start with curiosity rather than judgment

Resource Mentioned
- The Daily Stoic - recommended reading for clarity and perspective

Guest Bio
Dr. Christina Villarreal is one of Silicon Valley's most respected executive coaches, working with leaders at companies including OpenAI, Apple, Slack, and A16Z. She brings her background in psychology to help professionals navigate high-stakes transitions with confidence.

Find Christina at https://drchristinavillarreal.com/

Subscribe to our Substack at www.stuckpodcast.com
You can watch each episode on Youtube https://www.youtube.com/@areyoustuck

This show was produced by Rob Curtis, Jamal Stockton and Ximena de la Tijera

Co-hosts Rob Curtis and Jamal Stockton team up each week to help one person who’s feeling stuck in their career or life. Listen to the teaser episode to find out how.

Follow us on Youtube - https://www.youtube.com/@areyoustuck

Subscribe to our Substack at www.stuckpodcast.com
You can watch each episode on Youtube https://www.youtube.com/@areyoustuck

This show was produced by Rob Curtis, Jamal Stockton and Ximena de la Tijera