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.

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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.

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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.

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What We Cover

1. The difference between agency culture (younger, spiky hours, frequent fire drills) and in-house corporate roles (smoother pace, more stability).
2. Why marketing is often a home for "working creatives" like drummers or writers who need a steady paycheck.
3. The "whole brain" approach: combining right-brain emotion with left-brain analytics and math.
4. The reality of pitching in advertising: doing huge amounts of work for free just to win a client.
5. This career is not for people who need a rigid structure or cannot handle ambiguity.
6. The emotional toll of having creative work rejected or changed by upper management.
7. How AI is currently serving as an editor and thought partner rather than a total replacement for human creativity.
8. The influence of 20-somethings on culture and why brands look to them for trends like TikTok.

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Resources Mentioned

1. Charles Schwab
2. Northwestern University

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.

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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.

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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.

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What We Cover

1. Victor describes his role as a "founder" and "Chief Excitement Officer" across his companies.
2. The story of how Victor's wife convinced him to go to law school so people would take him seriously.
3. Why Victor left a prestigious "big law" job after missing Thanksgiving with his family.
4. The transition from practicing school law to estate planning and eventually adding financial services.
5. How technology and AI will force professionals to deliver higher value and move away from the billable hour.
6. The two types of people who succeed in this field are those who love numbers and those with high human empathy.
7. Why Victor believes you should never join the legal or financial profession solely for the money.
8. Victor's "Three Cs" of hiring: Character, Culture, and Competence.

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Resources Mentioned

1. Medina Law Group
2. Palante Wealth Advisors

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.

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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.

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Elliot 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.

1. The 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.
2. 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.
3. 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.
4. Market efficiency: How the move from fractional pricing (1/8th of a dollar) to pennies created an environment dominated by high-frequency trading firms.
5. 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.
6. 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.
7. The barrier to entry: Trading is unique because anyone can open an account and start immediately, unlike becoming a doctor or lawyer.

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1. Elliot Edelman on LinkedIn
2. Virtu Financial (High-frequency...

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.

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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.

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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.

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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.

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Frank 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.

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1. What “Assurance” is, and why companies come to Deloitte for help with complicated accounting and internal control type issues
2. Compliance, cybersecurity, and “all manner of things” businesses need to run a good business
3. “Trusted advisor” relationships, and how projects can be four-week projects or four-year projects
4. Campus hiring signals: accounting and finance and economic majors, plus IT experience or aptitude, like MIS or data science
5. Why soft skills matter: leading a team, communicating with a client verbally and in writing, and “reading the room.”
6. Travel, flexibility, remote work, and opportunities to live elsewhere for a little while
7. “Choose your own adventure” career paths: starting in audit, moving into consulting, and ending somewhere different than where you started
8. Who thrives, and who should run for the exits: thriving on ambiguity, not needing a ton of structure, and being willing to learn

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1. Larry...

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.

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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.

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David 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.

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1. The two stories to Lawline, a public access TV show, taking CLE online, “too early,” and a 2006 relaunch
2. Sales is the best experience, rejection, creativity, consistency, organization, and asking a lot of good questions
3. “Wolf of Wall Street” vs process, calling and doing the right things over and over
4. AI and inbox spam, “too good” emails, and why shorter and more personal is better
5. Law school, the Socratic method, case law, the cost, and “more experiential” apprenticeship experience
6. Entrepreneurship as a school project, making mistakes, leadership and mindset, and “stuck” phases at different levels
7. The Fast Forward Mindset, “fearless enough” and “focused enough,” and staying out of the comfort zone longer
8. Barcelona, strict lockdown, kids not allowed to leave for 52 days, eight o’clock pots and pans, and “a beautiful song”

1. Lawline
2. The Fast Forward Mindset
3. CLE (continuing legal ed)
4. Mark Cuban, broadcast.com, Yahoo
5. PBS

“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.

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Emily 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.”

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• What an information architect does: give structure to information, organize it, and make the most important information the easiest to find and the easiest to use
• Complex 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 degree
• Talking 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 models
• Who does well in the role: naturally curious, okay with ambiguity, and sees the forest and the trees at the same time
• AI, ethics, and information retrieval: search, browse, and now chat, plus “garbage in, garbage out”

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• Emily Claflin
• Larry Port
• The Understanding Group
• IA Conference
• AmeriCorps
• Facebook
• LinkedIn
• Zoom
• SharePoint
• GED classes

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.

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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.

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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.

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👤 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.

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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.

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📌 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 customers
• Quarterback and orchestra director analogies for product management, keeping the tempo and pace of software development, so everybody knows what they are building and why
• Concrete 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 be
• Day-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 cases
• Communication and empathy as critical soft skills, including stories from Rocket Matter, working with attorneys under a lot of pressure, and flexing that empathy muscle
• What 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 replacement
• Alejandro’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 roles
• Moving into sales engineering, solutions engineer, and sales operations manager, owning Salesforce integrations, automating syncs, and modernizing sales processes
• Why 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...

Larry Port talks with Patrick Leary about his career in finance, bond trading and sales, work-life balance, and what this job is like on a day-to-day basis at Loop Capital on the Dream Job Cafe podcast. Patrick talks about the bond market, how bonds do not trade on an exchange like stocks, why it takes actual people to make these transactions happen, and how an old-school market still has an electronic component. They walk through market hours, inventory, and the firm's risk position, travel with clients, and take advantage of the extra credit hours that come with being successful in this industry. Patrick shares how he moved from medicine and pre-law to the business school, an internally managed stock fund, and a junior trading intern role at a bank trust company. He describes how a professor who said he would teach how the world really works changed his financial literacy, why bond trading clicked, and how AI, algorithms, bespoke products, and large language models may shape the future for young people who are curious about this path.

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Patrick Leary is the managing director and head of trading at Loop Capital, leading the firm's fixed income division. His work sits in the bond market, trading government bonds, corporate bonds, muni bonds, and mortgage-backed securities with institutional clients. Patrick manages the firm's inventory and risk position, blending sales and trading with risk management and client service. He started as a junior trading intern at a local bank trust company in St Paul, trading equities and many different types of fixed income instruments on the buy side before moving to the broker-dealer world.

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• What this job is like for a head of trading in the bond market, from market hours and being tied to the bell to lunch breaks on the desk and work-life balance across time zones.
• How sales, trading, and risk management fit together, including inventory, client warehousing risk, and the differences between institutional clients, banks, hedge funds, money managers, and public entities.
• Patrick’s path from thinking about medicine and law to pre-law, the business school, an internally managed stock fund, and a professor who said he would teach how the world really works.
• Early experience as a junior trading intern at a bank trust company in St Paul, trading equities and many different types of fixed income instruments on the buy side before moving to a broker-dealer.
• The role of salespeople has changed, from entertaining clients with ball games and great dinners to using technology tools, electronic trading, and a more sophisticated, knowledgeable sales staff.
• The future of bond trading and sales, including commoditization and electronification, algorithms and trading programs, cryptocurrencies and stable coins, and bespoke products that are not easy to commoditise.
• The temperament and skills that help in this industry, like comfort with risk, thick skin, next trade mentality, networking, internships, and using AI and large language models as a calling card for young people.

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• Larry Port