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 academics
• Using the MBA to pivot into product, recruiting for Google, Apple, Amazon, Wayfair, VMware, and landing a technical product management internship at Amazon during the first year of COVID
• Falling in love with North Carolina, choosing not to move to Seattle, and building a relationship with the recruiter at Pendo, North Carolina’s first unicorn, to join a company that does software for product managers
• How work hours, travel, and lifestyle in product management depend on company size, industry, and person, from nine to five with Slack after hours, to talks at Duke, onsite visits, and international trips to places like Mexico City, the UK, and South America
• How AI and LLMs fit into product and engineering work today, helping with unit testing, triaging bugs, document feedback, and quicker prototyping, while creativity, junior talent, and core coding remain essential
• Who might be a good fit for product management, including people who like public speaking, talking to customers and C level leaders, dealing with ambiguity, and talking to a gamut of personalities across engineering, design, sales, and leadership

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🔗 Resources Mentioned

• Pendo.io
• Rocket Matter
• Facebook
• The Tipping Point by Malcolm Gladwell
• Atlas Shrugged
• Salesforce
• Florida Atlantic
• Duke University and Fuqua School of Business
• Amazon
• Google
• Apple
• Wayfair
• VMware
• Bolt
• Lovable
• V zero

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
• Patrick Leary
• Loop Capital
• Morgan Stanley
• IBM
• Robinhood
• Ted Lasso

Strategic career skills and the job market today are the focus as Larry Port sits down with his old friend Peri Ginsberg, founder and head coach of Workforce Ready Now. Peri works heavily with college graduates, new graduates, and really early stage professionals who are navigating the workforce and feeling the pressure that the first job is going to make or break their entire career.

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Peri shares how careers are rarely linear, how any job is going to teach you something, and how her own pivots from civil and environmental engineer to management consulting, Office Depot, and entrepreneurship built the wherewithal to do what she is doing today. Larry and Peri walk through what applicant tracking systems actually are, why they are not AI or a robot, and why keyword matching and formatting can stop you from getting an interview. They talk about the seven second test for resumes, students getting ghosted after hundreds or thousands of applications, and why networking, LinkedIn outreach, and relationship building are still the secret to landing jobs right now.

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Peri Ginsberg is the founder and head coach of Workforce Ready Now and works heavily with college graduates, new graduates, and really early stage professionals in navigating the workforce. Educated as a civil and environmental engineer, she did that for a couple years, then transitioned into management consulting, which she really loved. After relocating to South Florida for family reasons and no longer being able to travel, Peri became a director in the project management office at Office Depot. Eventually she departed from the corporate lifestyle because she had that entrepreneurial bug, ran a hair salon for children, and pivoted through multiple roles that set her up for success as a coach on resumes, networking, and interviewing.

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• Why careers are rarely linear, why that first job is not going to make or break your entire career, and how any job is going to teach you something, even what you do not like.
• Peri’s own pivots from civil and environmental engineer, to management consulting, to director in the project management office at Office Depot, to entrepreneurship and Workforce Ready Now.
• What applicant tracking systems are, why the ATS is not AI, not a robot, not an evil thing that is out to get you, and how must haves, nice to haves, and keyword matching score your resume.
• How pictures, a fancy logo, text boxes, and untraditional formatting can throw off the ATS, stop the system from parsing text correctly, and stop you from getting an interview, plus why ATS compliant templates matter.
• The difference between what the ATS cares about and what a human hiring manager cares about, including headings, dates, Times New Roman, tight spacing, one page resumes for college kids, and Peri’s seven second test with strategic bold and a touch of color.
• The Wall Street Journal picture of students sending out hundreds or thousands of resumes, getting crickets and being ghosted, blaming an evil applicant tracking system, and why networking is still essential.
• Networking that scares this generation, growing up behind a phone screen, the fear of picking up a phone and saying hello, and Peri’s coaching on LinkedIn messages that simply ask for a chat and information, not “Hey, will you hire me?”
• The Florida State and MLB story of Peri’s son, customized 300 character LinkedIn messages to three people at every MLB team, a call with someone at the Tampa Bay Rays, and an advocate who made sure three hiring managers had his resume in hand.
• Peri’s strategy of using AI and chat with ten job descriptions, creating three buckets, building three resumes around responsibilities, skills, and tools, and using those versions to match 95 percent of roles without customizing hundreds of times.
• The LinkedIn rule of three after every application: an alum, someone one or two years ahead who loves being asked for advice, and a manager or director or talent acquisition contact who can share what they look for in candidates.
• The UT Austin junior econ example, a student who applied to over a thousand jobs with no interviews, how a reworked, applicant tracking system friendly resume that shows what you can do opened three interviews in one week, and why the student did not change, only the way he communicated and represented himself.
• How Peri helps students with resume building, optimizing LinkedIn, networking, follow up beyond “I sent an email,” STAR methodology, behavioral, technical, and case interviews, marketing them into 500 or thousand strategic inboxes, and building confidence to articulate their value throughout their professional life.

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• Workforce Ready Now
• LinkedIn
• Indeed
• Wall Street Journal
• Office Depot
• Common App
• Ohio State and the Fisher School of Business
• Florida State
• MLB
• Tampa Bay Rays
• UT Austin

Middle skilled or new collar jobs, veterans, and the skilled workforce sit at the heart of this Dream Job Cafe conversation as host Larry Port talks with Emily Bose, managing director at Transition Overwatch. Emily works with companies and veterans through structured employment programs, retention support, and wraparound support that connect strong go getter people with employers who want to hire more veterans.

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She shares how recruiting can be really meaningful work, from placing a mechanic who totally changed the course of his life to helping veterans navigate military transition, tricky workplace communication, and promotions into the next level. Emily breaks down middle skilled and new collar jobs that do not always require a college degree, often pay well, and offer room to grow, especially in healthcare, manufacturing, aviation, and the skilled trades. She also highlights shift based work, flexibility, and how these jobs can help people build actual careers and even start their own businesses.

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Emily Bose is a managing director at Transition Overwatch, a startup that works with companies and veterans through structured employment programs and a retention program for the first one to two years of employment. She has been with the same company and the same CEO for about seven or eight years, starting in recruiting for manufacturing, where she placed around 90 people, including plant managers and roles from top to bottom in the organization.

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Emily talks every day with veterans about what they are trying to do next in their careers, their motivations, goals, and how programs can support that. She also hosts a podcast live on LinkedIn called the Emily Bow Show, talking about workforce things for the skilled trades and the next generation of skilled technicians.

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• How Transition Overwatch serves two real customers, companies and veterans, through structured employment programs, wraparound support, clear growth paths, and optimized benefits, with program lengths of one to two years and average retention pushing three years.
• Emily’s path from radiology and working as a student tech to recruiting in manufacturing, placing about 90 people, touring plants, and getting excited about this skilled workforce and middle skilled or new collar jobs.
• Why recruiting can be really meaningful work, including the story of a mechanic found on LinkedIn who was stuck in a dead end job and moved into a higher level of responsibility, traveling and representing his company.
• Skills for recruiting and sales, like quickly building rapport, getting people to open up about what they are really looking for, asking clarifying questions, taking lots and lots of notes, doing follow up, communication, and thinking creatively about search terms, titles, and adjacent industries.
• A grounded explanation of applicant tracking systems as a glorified CRM and filtering system, how answers in applications can be disqualifying, and why recruiters want to help people get hired rather than act as an evil A T S gatekeeper.
• A clear picture of middle skilled or new collar jobs that do not necessarily need a college degree, may come with on the job training or technical and trade schools, help people earn while they learn, and lead to growth in areas like radiology, healthcare, manufacturing, and other skilled arenas.
• The reality of shift based work, overtime and shift differentials, weekend and night work, and how schedules can support flexibility for young moms, students, and people who do not enjoy sitting at a desk all day.
• Why these jobs are not dead end jobs, with pathways into more advanced modalities, management, instruction, operations, quality, supply chain, safety, cybersecurity, and other roles that support plants, factories, and data centers.
• The difficulty of military transition, including many moving parts, unclear fits in the civilian marketplace, different communication styles, and how structured support for one or two years helps veterans handle vague emails, tricky conversations, and promotions into the next level.
• High demand across aviation, air traffic control, automotive, heavy equipment, construction, transportation, and data centers for trades like boiler makers, HVAC, plumbers, welders, and technicians, especially as experienced workers retire.
• How many industries are intentionally trying to bring in more non traditional talent, creating more inclusivity, belonging, and welcoming cultures for women, people of color, veterans, and other groups in the skilled workforce.
• The strong connection between skilled trades and entrepreneurship, including Emily’s note that 28 percent of people who go into the skilled trades start their own businesses compared to around 8 percent of the general workforce, and how entrepreneurship can help people control their own destiny.

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• Transition Overwatch
• Wall Street Journal article: “They are hot. Upwardly mobile jobs. Here’s why they are so hard to fill.”
• Emily Bose on LinkedIn
• The Emily Bow Show, live on LinkedIn, talking about workforce things for the skilled trades and workforce development across aviation, automotive, heavy equipment, construction, and more.

A kid from Tampa rides coasters at Busch Gardens, prints “theme park enthusiast” on a business card, and aims his entire college path at Disney. Then, at what feels like the culmination of that dream at Epcot, something inside says it is time to switch gears. In this conversation, Larry Port sits down with his cousin Sammy Port to trace a non-linear path that runs through Cornell’s hospitality school, long days in ride operations, the surreal training grounds of Disney University, singing on Vegas stages, cruise ship shows, producing an off-Broadway musical, and finding a home as Senior Creative Director at Proscenium. Listeners hear how support networks, authentic connections, accountability, and a willingness to say yes shape a sustainable creative life across entertainment, production, and DJing, without losing sight of real-world needs and human-centered work.

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Sammy Port is Senior Creative Director at Proscenium and a lifelong fan of large scale entertainment. He grew up in Tampa near Busch Gardens, studied at Cornell’s hospitality school with theme parks in mind, and worked in operations at parks including Busch Gardens, Cedar Point, Six Flags, and Epcot at Disney. Sammy performed in Las Vegas, on cruise ships, and in New York, helped produce the musical “Spandex,” and moved into event production with Proscenium. He curates music and creative experiences for major live events and also DJs high profile events such as Time 100.

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• Early obsession with theme parks, trade shows, and calling himself a “theme park enthusiast” at thirteen.
• How Cornell’s hospitality program, summer roles at Busch Gardens, Cedar Point, and Six Flags, and an Epcot internship created a focused path into theme park operations.
• The reality of “making it” at Disney, imposter syndrome, Disney University training, and why that milestone still did not feel complete.
• The courage and support network behind leaving a coveted Disney role to pursue performing, auditions, and learning through imperfect first steps.
• Moving to Las Vegas for “Jubilee,” performing on cruise ships, and the eventual shift to New York with an honest look at whether performing was truly in his heart.
• Producing the musical “Spandex” and how one coffee conversation led directly to an internship opportunity at Proscenium.
• Why a varied background across operations, performance, and production made Sammy the “missing piece” for a corporate events agency focused on theatrical, branded experiences.
• What a Senior Creative Director actually does: aligning designers, staging, lighting, visuals, music, and talent so everything feels cohesive for the brand.
• How curating event music evolved into DJing events like Time 100, and why that creative outlet fits naturally with his work at Proscenium.
• A candid reflection on career identity, not being defined only by a title, balancing financial stability with creative fulfillment, and finding energy in both work and side projects.
• Practical guidance for early career professionals: saying yes, doing unglamorous work, building real connections, following through, using accountability, and understanding the unseen effort behind “beautiful” events.
• Thoughts on AI in live events, how virtual experiences compare to being in the room, and why the human element in shared spaces still matters.

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• Proscenium
• Cornell University School of Hotel Administration
• Busch Gardens (Tampa)
• Cedar Point
• Six Flags New England
• Epcot / Disney University / Disney attractions
• Soarin’ (referenced as a newly opened attraction)
• “Jubilee” (Las Vegas show)
• Cruise ship productions
• “Spandex” (jukebox style musical about the eighties aerobics movement)
• Time 100
• T-Mobile
• Walmart
• Last Call (Cornell a cappella group)
• Tau Kappa Epsilon (TKE)

Law school, big law, lifestyle, AI, legal technology, small firm reality, student loan pressure and legal adjacent careers all collide in this conversation. Host Larry Port sits down with Jared Correia, who walks through his path from small liberal arts college English major and classics minor to Suffolk Law School, small firm practice, bar association work and founder of Red Cave Law Firm Consulting.

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Jared shares that he went to law school with no idea what he wanted to do, discovered he did not like practicing law, and pivoted into consulting after seeing how many firms lacked basic business management. Larry and Jared break down different practice areas, lifestyle practices like estate planning, the grind of personal injury and big law, why so many lawyers are depressed, and how AI and cloud software reshape research, document drafting and staffing. Listeners hear honest advice on knowing why you want to go to law school, understanding debt, exploring legal adjacent work and building skills in communication, sales, customer service and AI.

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Jared Correia is the Founder and CEO of Red Cave Law Firm Consulting, providing business management consulting services for lawyers and law firms, as well as technology and marketing consulting for legal institutions and legal-facing businesses. A former practicing attorney and bar association administrator, he has worked with thousands of law firms and hosts legal industry podcasts and events. Jared brings honest insight on law school decisions, small firm life, big law, legal technology, AI and alternative paths in the legal world.

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• Going to a small liberal arts college, choosing English and classics without a plan, joining the debate team and deciding to apply to law school late with a middling LSAT.
• How Jared chose Suffolk Law School over Santa Clara, went straight through without a break and then discovered through electives that he did not like any of the traditional profitable paths.
• Why he says he probably should not have gone to law school, and why students should understand what lawyers do, talk to lawyers, shadow, and avoid going in just for money.
• Clear examples of how different practice areas shape real life: personal injury as scratching lottery tickets and eating ramen, estate planning as a lifestyle practice with flexible hours, and the strain of litigation work.
• Honest talk on big law, billable culture, giving away your twenties, and why many lawyers feel trapped with significant student loan payments, old cars, no house and repetitive, stressful work.
• The emotional and mental load of lawyering: worst case scenario thinking, constant client crises, pessimism, and how that bleeds into personal life and fuels depression and burnout.
• Jared’s pivot story: leaving small firm practice, joining a bar association, moving into a consulting role for thousands of lawyers, using cloud software, social media and podcasting to build a profile in legal consulting.
• How AI and legal tech intersect with law firm work, why many lawyers are still not really using AI, what can be automated in document review and drafting, and why future lawyers should build strengths in sales, customer service and prompting AI.

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• Red Cave Law Firm Consulting
• St. Anselm College
• Santa Clara University
• Suffolk University Law School
• Massachusetts Bar Association consulting program (business management support for lawyers)
• Rocket Matter
• AI tools and ChatGPT style assistants
• Estate planning software and forms based practices
• Michigan State law programs (referenced in connection with Dan Linna)
• University of South Carolina School of Law (referenced with Dave Maxfield)
• Jeff Bezos
• Billy Joel, The Stranger
• Tom Petty, Full Moon Fever
• Jeff Lynne
• To Kill a Mockingbird

Anxiety is running high for new graduates and career changers as industries shift and the job market feels locked. Joseph Lewin joins Larry Port to talk about what’s behind the frustration so many students face as they send out hundreds of resumes without a response. They explore why traditional job applications fail, how to think about career direction, and what to do when your degree doesn’t lead to immediate opportunities.

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Larry shares his direct experiences mentoring college students and guiding his own kids through the career search process. The conversation moves from self-awareness and lifestyle choices to practical strategies for networking, exploring internships, and finding new ways to stand out in a crowded field.

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• Why so many recent graduates feel anxious about their job prospects
• How to figure out what kind of career actually fits your strengths and lifestyle
• The importance of honest self-assessment and knowing what you’re good at (and not)
• Real-world examples, like a real estate agent balancing flexibility with constant availability
• How the flood of computer science graduates changed the hiring landscape
• Where to look for opportunity in tech: DevOps, AI infrastructure, cybersecurity, and data analytics
• The value of networking and talking to people over mass resume submissions
• Why applicant tracking systems (ATS) have broken the job application proces
• How to reach out effectively on LinkedIn and what not to say when networking
• How internships act as extended interviews and lead to long-term roles
• The recurring theme: relationships drive career success at every stage

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• LinkedIn (for networking and outreach)
• DevOps and cloud infrastructure
• Cybersecurity and data analytics fields
• Applicant Tracking Systems (ATS)

Figuring out what career path to take is intimidating. Larry Port talks through the massive chasm after graduation, the luxury of choices, and the work of connecting who you are to the life you want. Joseph surfaces real tensions around hard skills versus the lifestyle you actually want, parental pressure, and the risk of walking a predetermined path. Larry shares personal shifts from photojournalism to software and entrepreneurship, why family dinner and coaching Little League mattered, and how looking at who you will become in a field can guide decisions.

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The conversation gets practical on the current AI transition, conflicting studies, what the tools can do right now, and why using them increases throughput. They compare startups and large companies, risk, culture, and wearing different hats, then map rising and retracting industries by paying attention to the news, demographics, energy, and the kinds of work that will be automated.

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• The massive chasm after college and why choices feel daunting
• Hard skills, aptitude, and whether the job translates to the life you want
• Parental pressure, predetermined paths, and the cost of avoiding uncertainty
• Looking at who you will be in a field by watching people ahead of you
• AI transition in October 2025, conflicting studies, and real use cases that increase throughput
• Startups versus large companies, culture, risk, and wearing different hats
• Entrepreneurship temperament, roller coaster moments, and time freedom
• Industries to watch: healthcare ecosystems, robotics, sales, energy, and roles supplying AI

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• ChatGPT
• OpenAI and Sam Altman
• Yale study; Stanford study
• Morgan Stanley
• Ernst and Young
• Goldman Sachs
• Robotics; humanoid robots
• DevOps

What should I do with my life? It is a question almost everyone has asked. Larry Port opens the conversation by exploring the difficult transition from school to the workforce and the overwhelming chasm that graduates face when trying to figure out what comes next. He reflects on the challenges of standing out with a degree that looks like everyone else’s while automation and AI reshape white collar jobs.

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Larry shares his own experience of discovering that photojournalism, though exciting on paper, conflicted with the family life he wanted. He highlights how overlooked careers, from user experience engineering to sales and finance, can be rewarding yet rarely appear on a college counselor’s radar. Alongside producer Joseph Lewin, the discussion focuses on listening to your inner voice, aligning career choices with personal goals, and paying attention to labor market trends. This episode sets the stage for a show dedicated to helping students, career changers, and professionals navigate the uncertainty of work and life.

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• The overwhelming transition from college to career and how to stand out
• Why a career on paper can look very different from real life
• Larry’s story of pursuing photojournalism and realizing its lifestyle trade-offs
• Careers that few people know exist, from user experience engineering to event planning
• How overlooked roles in sales and finance can align with personality and goals
• The importance of listening to your inner voice when making career decisions
• Paying attention to labor market news and societal trends to anticipate opportunities
• Why Dream Job Cafe exists and who will benefit from tuning in

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• Larry Port (Host)
• Joseph Lewin (Producer)
• Wall Street Journal (labor market trends mentioned)

Larry Port introduces Dream Job Cafe — a show about uncovering what careers are really like, beyond the glossy titles and résumés. Hear why this podcast exists, who it’s for, and how real conversations with professionals can help you figure out if a career path fits the life you want to live.