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

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...

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...

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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