Stuck - Expert Career Advice with Rob and Jamal

Rob Curtis
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Feeling like something at work needs to change, but you’re afraid to take the leap without risking your financial plans? Co-hosts Rob Curtis and Jamal Stockton team up each week to help one person who’s feeling stuck in their career or life. We match real questions from listeners with expert advisors who help you build a toolbox of practical, actionable insights to get you ready to make your own big move. All mixed in with human stories from people, like you, that left corporate life to chase something bigger. 

Episodes

  1. 02/27/2025

    Demystifying Fractional Leadership & AI with Karyn Scott

    🎙️ 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 Enjoying the Podcast? If you loved this episode, make sure to: ⭐ Subscribe & Review – It helps us bring in more incredible guests! 🎧 Share this episode with someone who needs to hear it! 📩 Send us a voice note at stuck@213studios.com 🚀 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

    36 min

  2. 02/20/2025

    106: A Look into the Future of Work

    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 automationHow company structures are evolving in the AI eraTransitioning between startup and corporate environmentsBuilding successful businesses in an AI-first worldPractical applications of AI for personal and business productivity Key Takeaways AI works best when humans remain engaged in reviewing and guiding outputsFuture companies may be smaller but more senior, with AI augmenting capabilitiesThe path to entrepreneurship is changing with lower barriers to entrySuccess in the AI era requires authenticity and community buildingStarting with personal productivity use cases is an effective way to adopt AI Practical Insights AI automation examples: Email and calendar managementCustomer research and communicationContent creation and analysisAutomated reporting and documentationVideo and audio content production Career Lessons The importance of staying close to actual work vs pure managementHow to maintain authenticity while leveraging AI toolsWhy company building is becoming less capital intensiveThe value of finding the right problem vs rushing to marketBuilding trust and community in an AI-enabled world Future of Work Predictions Companies will likely become smaller but more impactfulJunior execution roles may decrease as AI handles basic tasksMore emphasis on "player-coach" roles combining strategy and executionMultiple successful companies can coexist in the same spaceGrowing 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 platformLinkedIn - Follow Jacob for practical AI implementation tipsWeekly "Build with Me" sessions - Live AI automation tutorialsRecommended AI tools: CaptionHeyGenClaudeChatGPT Contact Information LinkedIn: Jacob BankEmail: jacob@relay.appYouTube: Relay.app channel About Stuck Subscribe to Stuck on Apple Podcasts, Spotify, or wherever you get your podcasts. Email us: stuck@213studios.com 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

    49 min

  3. 02/13/2025

    105: From AOL Lawyer to Purpose-Driven Deal Maker with Jan D'Alessandro.

    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 1990sTransitioning from corporate law to business developmentBuilding win-win partnerships across tech, media and entertainmentCreating sustainable corporate giving programsNavigating 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 thinkingNegotiation skillsDeal structuringUnderstanding multiple stakeholdersLook for opportunities to merge your professional skills with personal interestsConsider how your expertise could apply to emerging fields like AIFocus on building win-win partnerships rather than just transactionsStay connected to what energizes you, even if it means changing roles Key Lessons for Career Transitions Be honest with yourself about what naturally energizes youLook at what you spend your free time doing - there are jobs related to any interestFocus on transferable skills rather than just industry experienceDon't underestimate the value of your professional training in new contextsConsider 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 practiceThe Innovator's Dilemma by Clayton Christensen About Stuck Subscribe to Stuck on Apple Podcasts, Spotify, or wherever you get your podcasts. Email us at stuck@213studios.com. 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

    35 min

  4. 02/05/2025

    104: How to talk to your loved ones about money with Financial Therapist, Aja Evans

    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 partnersSetting and maintaining financial boundariesManaging money with kids and dependentsUnderstanding your personal money storyDealing with guilt and shame around financial changesBuilding 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 peopleUse "I feel" statements and center emotions when discussing financial changesYour money beliefs are shaped by your earliest experiences - understanding this helps navigate current challengesSetting boundaries isn't just about saying "no" to others - it's also about setting limits with yourselfBe age-appropriate when discussing money with childrenFocus on experiences and long-term investing for kids rather than material goods Practical Tips For Money Conversations: Choose the right time and settingLead with emotions and personal experienceGive partners grace to process informationUse "I feel" statementsAvoid springing sensitive conversations without warningFor Building Money Systems: Start by understanding your feelings about moneyKnow what's coming in and going out monthlySet up automated payments where possibleCheck finances at least monthly (weekly preferred)Use high-yield savings accounts for emergency fundsFor Setting Boundaries: Communicate changes in financial situation clearlyOffer alternative ways to show love/support beyond moneyRemember that people's reactions belong to themBe prepared for initial negative responsesFocus 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 EvansApps 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: @AJAetherapyLinkedIn: Aja Evans LMHCWebsite: ajaevanscounseling.comBook: "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 stuck@213studios.com 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

    51 min

  5. 01/30/2025

    103: "Money Mindset: Making Financial Decisions That Stick" with Brian Pasalich, CEO of Behave Technologies

    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 itFour key factors you can control: earn more, spend less, delay goals, or change goalsSometimes you need to "suck it up" to achieve longer-term goalsThe importance of aligning financial decisions with personal valuesSpecial Offer: The first 10 listeners to send a voice note to stuck@213studios.com will receive a free financial decision-making style assessment. Follow Stuck: Website: www.stuckpodcast.com   Email: stuck@213studios.com 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

    28 min

  6. 01/22/2025

    102: From Tech Executive to Gym Owner: A Story of Reinvention

    **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: stuck@213studios.com 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

    33 min

  7. 01/21/2025

    101: Are You Stuck or Just Impatient? A Silicon Valley Coach's Guide to Career Change

    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

    50 min

  8. SEASON 1, EPISODE 1 TRAILER

    Rob and Jamal explain what happens on Stuck

    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

    2 min

Trailer

About

Feeling like something at work needs to change, but you’re afraid to take the leap without risking your financial plans? Co-hosts Rob Curtis and Jamal Stockton team up each week to help one person who’s feeling stuck in their career or life. We match real questions from listeners with expert advisors who help you build a toolbox of practical, actionable insights to get you ready to make your own big move. All mixed in with human stories from people, like you, that left corporate life to chase something bigger. 

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