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