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