Stuck - Expert Career Advice with Rob and Jamal

🎙️ 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

STUCK - 

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
Be honest with yourself about what naturally energizes you
Look at what you spend your free time doing - there are jobs related to any interest
Focus on transferable skills rather than just industry experience
Don't underestimate the value of your professional training in new contexts
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
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

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

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