Dream Job Cafe

Larry Port
  • 5.0 (3)
  • CAREERS

Dream Job Café is the podcast for anyone navigating their next career move, a challenge that’s only gotten trickier now that AI has joined the mix. Hosted by Larry Port, each episode goes beyond job titles to explore the realities of different professions — from daily schedules and travel demands to pay, pressure, and whether that career will exist in five years. ㅤ You’ll hear from industry leaders, working professionals, and career experts who share candid stories about what it’s really like to do the job. Whether you’re a college student facing an uncertain job market, a recent graduate navigating new opportunities, or a mid-career professional who needs a change, this show will help you sort through options with clarity and confidence. ㅤ Dream Job Cafe is here to help you align your skills, values, and lifestyle goals so you can not just imagine but actually pursue your dream job.

  1. 4D AGO

    Life as a Firefighter Paramedic (with Marc Juliano) | Ep. 16

    Many people picture firefighters rushing into burning buildings every day. In reality, modern first responders in South Florida handle mostly medical calls and complex prevention work. Host Larry Port sits down with Marc Juliano, a veteran Firefighter/Paramedic and current Fire Safety Inspector with Broward Sheriff Fire Rescue. ㅤ Marc breaks down the truth about the job: from the 24-hours-on, 48-hours-off schedule to the "second family" dynamic at the station. He explains why 88% of calls are medical, the operational toll of the opioid epidemic, and how fire codes prevent tragedies before they start. You will learn exactly how to enter this field, the specific schooling required, and why being late is the ultimate cardinal sin in this line of work. ㅤ About Marc Juliano Marc Juliano is a Firefighter/Paramedic and Fire Safety Inspector for Deerfield Beach Fire-Rescue, contracted through the Broward Sheriff’s Office (BSO). With over 20 years in the service, he spent 16 years "on the trucks" responding to emergency calls before moving into fire prevention and code compliance. ㅤ What We Cover The operational reality of the 24-hours-on, 48-hours-off shift schedule.Why 88% of modern fire rescue calls medically related rather than structural fires?The "Risk a lot to save a lot" philosophy regarding property versus life safety.How a "Kelly Day" works and how firefighters stack vacation time for long breaks.Transitioning from riding the trucks to the preventative side of Fire Safety Inspection.The station dynamic: Grocery shopping, cooking, and training as a "second family."Educational requirements: EMT school, Fire Academy, and Paramedic certification.The impact of the opioid epidemic and Fentanyl on first responder resources. ㅤ Resources Mentioned NFPA (National Fire Protection Association)Chicago Fire (TV Show)Backdraft (Movie)

    47 min

  2. FEB 11

    Marketing Careers from Agency to In-House (with Scott Redick) | Ep. 15

    Marketing careers offer a unique path for creative professionals seeking stability. This field attracts liberal arts majors, musicians, and writers who want to leverage their right-brain skills while securing a 401 (k). Host Larry Port speaks with Scott Redick, the Managing Director of Retail Acquisition Strategy and Integration at Charles Schwab. Scott breaks down the two main worlds in this industry: agency work versus in-house roles at a brand. ㅤ Scott shares the reality of agency life, which can involve long hours, constant pitching, and fire drills. He contrasts this with the client side, where the pace is often smoother and more focused on long-term strategy. They discuss the "whole brain" thinking required to succeed, blending emotional creativity with analytical logic. Scott also explains why this career requires a thick skin: you might pour your soul into a project only to have a manager request a different color at the last minute. ㅤ Guest Bio Scott Redick is a marketing executive and strategist currently serving as the Managing Director of Retail Acquisition Strategy and Integration at Charles Schwab. Before joining the client side, he spent years in the agency world, including a role as President and Head of Strategy at Heat (acquired by Deloitte Digital). He has also held leadership roles at Isobar and DDB. Scott holds a Bachelor of Science in Journalism from Northwestern University. ㅤ What We Cover The difference between agency culture (younger, spiky hours, frequent fire drills) and in-house corporate roles (smoother pace, more stability).Why marketing is often a home for "working creatives" like drummers or writers who need a steady paycheck.The "whole brain" approach: combining right-brain emotion with left-brain analytics and math.The reality of pitching in advertising: doing huge amounts of work for free just to win a client.This career is not for people who need a rigid structure or cannot handle ambiguity.The emotional toll of having creative work rejected or changed by upper management.How AI is currently serving as an editor and thought partner rather than a total replacement for human creativity.The influence of 20-somethings on culture and why brands look to them for trends like TikTok. ㅤ Resources Mentioned Charles SchwabNorthwestern University

    35 min

  3. FEB 4

    Estate Planning Law and Financial Planning: Crushing Professional Services (with Victor Medina) | Ep. 14

    Victor Medina joins Larry Port to share his journey from a "baby 22-year-old" with a psychology degree to a dual-certified attorney and financial advisor. Victor explains how a direct conversation with his wife pushed him toward law school and why he eventually walked away from a high-paying job at a large firm to start his own practice. He discusses the reality of working in professional services: it is not just about spreadsheets or legal briefs. ㅤ Victor and Larry discuss the future of the industry, specifically how artificial intelligence and technology will impact legal and financial careers. Victor argues that technology is an augmentation tool rather than a replacement. He also breaks down his specific hiring philosophy for young professionals. Victor prioritizes character and culture over competence because he believes technical skills can always be trained. ㅤ Guest Bio Victor Medina is the Managing Partner of Medina Law Group and the Founder and Chief Executive Officer of Palante Wealth Advisors. Based in Pennington, New Jersey, he holds designations as a Certified Elder Law Attorney (CELA®) and a CERTIFIED FINANCIAL PLANNER™ (CFP®). Victor focuses on helping people lead a great life in retirement by coordinating income, investments, taxes, and estate planning. He is also the host of Retirease Radio. ㅤ What We Cover Victor describes his role as a "founder" and "Chief Excitement Officer" across his companies.The story of how Victor's wife convinced him to go to law school so people would take him seriously.Why Victor left a prestigious "big law" job after missing Thanksgiving with his family.The transition from practicing school law to estate planning and eventually adding financial services.How technology and AI will force professionals to deliver higher value and move away from the billable hour.The two types of people who succeed in this field are those who love numbers and those with high human empathy.Why Victor believes you should never join the legal or financial profession solely for the money.Victor's "Three Cs" of hiring: Character, Culture, and Competence. ㅤ Resources Mentioned Medina Law GroupPalante Wealth Advisorsa href="https://retireaseradio.com/"...

    34 min

  4. JAN 28

    How To Successfully Trade as an Independent Stock Broker (with Elliot Edelman) | Ep. 13

    Larry Port sits down with his old Little League coaching friend, Elliot Edelman, to discuss the reality of making a living in the stock market. After 30 years as a professional trader working for hedge funds and proprietary firms, Elliot recently made a major pivot: he left the corporate office to trade his own money from home. ㅤ Elliot explains the trade-offs of this lifestyle change. He no longer has access to firm leverage or a back office, but he also avoids compliance headaches and the commute. He shares honest insights on what it actually takes to survive as a trader. It requires a grasp of probability akin to that in poker, the discipline to handle losses, and the ability to compete against high-frequency algorithms. Larry and Elliot also discuss the "efficient market," why retail traders sometimes outsmart the pros, and how AI might change the finance industry forever. ㅤ Guest BioElliot Edelman is a seasoned financial professional with 30 years of experience in the securities industry. He spent over a decade as a proprietary trader at T3 Trading Group, LLC, before transitioning to self-employment in January 2023. Holding an MBA and a background in programming, Elliot now operates as an independent trader and financial content writer, focusing on quantitative market analysis and educational material. ㅤWhat We CoverThe transition to independent trading: Elliot describes leaving the proprietary firm environment to trade his own account, noting the freedom to finally "walk around at noon" on a Wednesday.Breaking into the industry: The story of how headhunters called Elliot "washed up" at 27 and how he eventually used his programming skills and MBA to get his foot in the door at a hedge fund.The trader mindset: Why successful traders need to understand risk and probability rather than just loving stocks. Elliot compares trading logic to sports betting and poker.Market efficiency: How the move from fractional pricing (1/8th of a dollar) to pennies created an environment dominated by high-frequency trading firms.Retail vs. Professional traders: A look at how amateur traders often win by "buying the dip" on popular stocks, while professionals sometimes over-analyze valuations.The future of finance jobs: Elliot discusses how AI is already automating tasks like writing 10-K reports and what this means for young people entering the field.The barrier to entry: Trading is unique because anyone can open an account and start immediately, unlike becoming a doctor or lawyer. ㅤ Resources MentionedElliot Edelman on LinkedInVirtu Financial (High-frequency...

    31 min

  5. JAN 21

    Consulting As A Career: One of the Biggest Names in the Field! (with Frank Milano from Deloitte) | Ep. 12

    Businesses have to be compliant with any number of different things, and it can feel like a hidden area of business until somebody explains what it is and what it looks like day to day. ㅤ Larry Port talks with Frank Milano about Assurance, Deloitte, and what it means to help clients with complex accounting and internal control issues, including cybersecurity and all manner of things that require compliance to run a good business. ㅤ Frank describes consulting relationships that can be four-week or four-year projects, and explains why being a client’s trusted advisor depends on trust, communication, and showing up as your best self all the time. ㅤ The conversation covers travel, remote work, and opportunities across the global network, plus what types of people thrive in professional services, especially people who thrive on ambiguity, are curious, and are ferocious learners. Frank also shares how he started in audit, became a CPA, moved into consulting, and how technology and AI may change the work without changing the mission. ㅤ 👤 Guest BioFrank Milano is a partner at Deloitte and the managing partner for the Assurance business. He describes Deloitte as a massive professional services firm with consulting, tax, accounting, and advisory work, and says the job is to help clients with complex accounting and internal control issues. Frank started out auditing a very specific client in New York City, went to SUNY-Albany, passed the CPA exam, and later got more into the finance systems side of things in a consulting capacity. He also talks about traveling to India and working with clients and organizations of all sizes and shapes, all over the world. ㅤ 📌 What We CoverWhat “Assurance” is, and why companies come to Deloitte for help with complicated accounting and internal control type issuesCompliance, cybersecurity, and “all manner of things” businesses need to run a good business“Trusted advisor” relationships, and how projects can be four-week projects or four-year projectsCampus hiring signals: accounting and finance and economic majors, plus IT experience or aptitude, like MIS or data scienceWhy soft skills matter: leading a team, communicating with a client verbally and in writing, and “reading the room.”Travel, flexibility, remote work, and opportunities to live elsewhere for a little while“Choose your own adventure” career paths: starting in audit, moving into consulting, and ending somewhere different than where you startedWho thrives, and who should run for the exits: thriving on ambiguity, not needing a ton of structure, and being willing to learn ㅤ 🔗 Resources MentionedLarry...

    29 min

  6. JAN 14

    Control of your destiny and “less risky” than a 9-5 job (with David Schnurman) | Ep. 11

    People think it’s less risky to be in a nine-to-five job, but sometimes it’s the most risky thing because you don’t control what can happen to you. Larry Port talks with David Schnurman about entrepreneurship, mindset, leadership, culture, and the long game of building something over 20 years. ㅤ David shares two stories: from a public-access TV show named Lawline to taking CLE online, dissolving the company, and relaunching in 2006 with a high school intern and essentially zero revenue. They discuss sales, rejection, creativity, asking good questions, and how AI has changed the inbox with spam emails that are “too good.” David explains The Fast Forward Mindset, getting out of the comfort zone and staying out longer, moving a family to Barcelona, getting stuck in the strictest lockdown in Europe, and rebuilding the family operating system through travel. ㅤ 👤 Guest BioDavid Schnurman is the CEO of Lawline. He shares two stories with Lawline: a 1999 idea to take CLE online, a brutal early period with dial-up, and a 2006 relaunch and rebuild of accreditation. David talks about sales, law school, leadership challenges, building the right team, and a structured hiring process. He is the author of The Fast Forward Mindset and shares why he moved his family to Barcelona and how that experience changed how they travel and explore. ㅤ 📌 What We CoverThe two stories to Lawline, a public access TV show, taking CLE online, “too early,” and a 2006 relaunchSales is the best experience, rejection, creativity, consistency, organization, and asking a lot of good questions“Wolf of Wall Street” vs process, calling and doing the right things over and overAI and inbox spam, “too good” emails, and why shorter and more personal is betterLaw school, the Socratic method, case law, the cost, and “more experiential” apprenticeship experienceEntrepreneurship as a school project, making mistakes, leadership and mindset, and “stuck” phases at different levelsThe Fast Forward Mindset, “fearless enough” and “focused enough,” and staying out of the comfort zone longerBarcelona, strict lockdown, kids not allowed to leave for 52 days, eight o’clock pots and pans, and “a beautiful song” ㅤ🔗 Resources MentionedLawlineThe Fast Forward MindsetCLE (continuing legal ed)Mark Cuban, broadcast.com, YahooPBSspan class="ql-ui"...

    32 min

  7. JAN 7

    What does an INFORMATION ARCHITECT do? (with Emily Claflin) | 10

    “We live in a world today where we spend a lot of time in these places that are made of information instead of being a physical place.” Larry Port talks with Emily Claflin, an information architect at The Understanding Group, about structuring and organizing information in ways that are useful to people. The conversation moves from websites, intranets, and apps to enterprise environments where you cannot make the complexity go away, but you can bring clarity. Emily shares a career story that starts with history and sociology, a year of service with AmeriCorps, public libraries, a master’s in library and information science, and then an internship that became full-time work. Along the way: talk to your professors, because all sorts of opportunities open up. The conversation also touches on AI, search, browsing, and chat, as well as “garbage in, garbage out,” ethics, and navigating organizational complexity. ㅤ Guest BioEmily Claflin is an information architect with The Understanding Group. She came from library science, worked in a local public library system, and did her master’s program fully online while working full-time. She took a class in information architecture, got an internship, and then went from hourly, part-time work while finishing school to full-time work. She also talks about serving as a conference chair and selecting a theme such as “navigating complexity.” ㅤ What We CoverWhat an information architect does: give structure to information, organize it, and make the most important information the easiest to find and the easiest to useComplex information environments: clarity, relevance, and “one kind of person with one particular goal”Information architecture and user experience design: a blurry line, “behind the scenes,” and “hopefully you never notice it”A career that was not a clear end goal: history and sociology, Spanish minor, study abroad, AmeriCorps, public libraries, and a master’s degreeTalking to the deputy director, getting a mentor-like conversation, and planning “three or five years from now”Research as a prerequisite: recruiting, interviews, trade shows, and synthesizing insights into shared artifacts and modelsWho does well in the role: naturally curious, okay with ambiguity, and sees the forest and the trees at the same timeAI, ethics, and information retrieval: search, browse, and now chat, plus “garbage in, garbage out” ㅤ Resources MentionedEmily ClaflinLarry PortThe Understanding GroupIA ConferenceAmeriCorpsFacebookLinkedInZoomSharePointGED classes

    29 min

  8. 12/17/2025

    Communication, Empathy, and Ambiguity in Product Management (with Alejandro Dao) | Ep. 9

    People trying to figure out what they wanna do for a living hear Larry Port talk with his good friend Alejandro Dao, lead product manager at Pendo.io, a very cool and innovative software company in North Carolina. Alejandro describes product management as leading the product's vision and strategy, deciding what to build next and why, and working with engineering, design, and customers. ㅤ He compares the role to a quarterback and an orchestra director, keeping the tempo and pace of software development and making sure everybody knows what they are building and why. Alejandro shares a mix of tactical and strategic work, from sprints and steel threads to roadmap meetings, user empathy, and many conversations with customers. ㅤ The conversation walks through his trajectory from a shy kid and Model UN to a support engineer, software developer, sales engineer, sales operations manager, MBA at Duke, an internship at Amazon, and landing at Pendo in Raleigh, North Carolina. ㅤ 👤 Guest Bio Alejandro Dao is a lead product manager at Pendo.io in North Carolina. Originally from Venezuela, he has a background in computer science and engineering. Alejandro started as a support engineer and software developer at Rocket Matter, then moved into sales engineering, solutions engineer, and sales operations manager, owning Salesforce and sales processes. ㅤ He completed a two-year MBA program at Duke’s Fuqua School of Business and used that to pivot into product management. After a technical product management internship at Amazon, he chose to stay in North Carolina. He joined Pendo, where he owns the guides product and spends a lot of time with engineering, design, and customers. ㅤ 📌 What We Cover What a product manager is, leading the vision and the strategy of the product, deciding what should be built next and why, and working with engineering, design, and customersQuarterback and orchestra director analogies for product management, keeping the tempo and pace of software development, so everybody knows what they are building and whyConcrete examples from Pendo, with two big pillars, analytics and guides, and Alejandro owning the guides product and crafting what the vision of the product is going to beDay-to-day work that mixes tactical and strategic, from sprints, steel threads, and compromises to roadmap meetings, senior leadership, and a lot of meetings with customers about frictions, frustrations, and use casesCommunication and empathy as critical soft skills, including stories from Rocket Matter, working with attorneys under a lot of pressure, and flexing that empathy muscleWhat it is like to work with engineers and UX designers, speaking the same language, rowing in the same direction, building prototypes together with tools like Bolt, Lovable, and V zero, and using AI as a superpower, not a replacementAlejandro’s path froma shy kid and Model UN, into computer science and engineering, video games, Florida Atlantic, a career fair conversation about Atlas Shrugged, and eight years at Rocket Matter in multiple rolesMoving into sales engineering, solutions engineer, and sales operations manager, owning Salesforce integrations, automating syncs, and modernizing sales processesWhy Alejandro wanted an MBA at Duke, filling knowledge gaps in accounting, finance, and business administration, and how the hardest part was getting in, not the...

    30 min
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Ratings & Reviews

5
out of 5
3 Ratings

About

Dream Job Café is the podcast for anyone navigating their next career move, a challenge that’s only gotten trickier now that AI has joined the mix. Hosted by Larry Port, each episode goes beyond job titles to explore the realities of different professions — from daily schedules and travel demands to pay, pressure, and whether that career will exist in five years. ㅤ You’ll hear from industry leaders, working professionals, and career experts who share candid stories about what it’s really like to do the job. Whether you’re a college student facing an uncertain job market, a recent graduate navigating new opportunities, or a mid-career professional who needs a change, this show will help you sort through options with clarity and confidence. ㅤ Dream Job Cafe is here to help you align your skills, values, and lifestyle goals so you can not just imagine but actually pursue your dream job.

Information

  • Creator
    Larry Port
  • Years Active
    2025 - 2026
  • Episodes
    17
  • Rating
    Clean
  • Copyright
    © Copyright 2026 Larry Port
  • Show Website
    Dream Job Cafe