Leland+ Content Library

Build a Full Trip Itinerary with Claude (Cowork, Code & Design)

A complete all-in-one, customizable system for planning a full, day-by-day trip with Claude — from a single intake to a dynamic, updateable, customizable plan. This deck walks through every component: destination research, flights, points-aware lodging, the day-by-day itinerary, restaurants and reservations, packing, credit-card credits, and best-time-to-visit timing — plus the Cowork-vs-Code playbook (where chat shines for research, synthesis, and drafting, and where Claude Code wins for schedule generation, calendar sync, and packing lists). It's built around a fully worked, anonymized example: a two-week Spain trip across Mallorca, Ibiza, Granada, and Madrid. For anyone traveling soon — or tired of losing a Saturday to 47 browser tabs — who wants AI to do the heavy lifting and one shared source of truth. A companion prompt library will be added so you can run the whole workflow yourself.

MBA Self-Discovery Workbook: Unlock Your Narrative & Write Freely

This is a reflection-focused, 13-section workbook for MBA applicants to uncover and build your story before embarking on the complex, layered process of writing your essays. This resource is informed from my time in Stanford GSB's Interpersonal Dynamics (Touchy Feely), my time helping dozens of other GSB classmates find their voice as the Managing Editor for Stanford GSB's Paper (Nondisclosure), and in helping over 500 MBA applicants self-reflect in a way that feels genuine, personal and clarifying. I wrote this resource with just enough structure (but not too much), and with a practical eye towards covering the ground you'll need for your MBA apps. You'll go deep, but every question has a purpose. I also use this with everyone I work with, and it's something we'll cover at the very beginning of our process. My hope is that this resource, in addition to being a big help, feels like we're in conversation. The goal is just to get to know you a little better, one step at a time, in a way that feels natural, even enjoyable. Even if you're the only one who ever sees it, I've tried to write this in a way that I'd speak about this kind of thing with you. Because I think humans are the best way to help other humans see themselves a little deeper. And trust me, plenty of "coaches" could use more of that too ;) This workbook will cover your background, motivations, short and long-term goals, values, behavioral stories, and more. A PDF is attached here, but there's also a downloadable Word file I recommend using to make things much easier for you to fill out as you go. This took me about 20-30 hours of time to put together, and I suggest putting at least 5-10 into filling this out. Some go at it all at once, but most do it in a few sittings. Long walks are good to interperse between writing sessions, and I actually recommend you reflect and go back to this to update your answers several times throughout your MBA process. Save new versions as you go and you'll be able to see your application pixellate over this monthslong process. If you're reapplying, I'd push you to compare what you end up with here with what you submitted last time. The differences may be revealing. I hope ends up a real tool for you, and that it helps you find answers you might not have found otherwise. It also will give you a glimpse into what coaching together feels like. Don't hesitate to reach out if you feel like sharing this. Working on your writing and applications together is a natural byproduct of the kind of reflection you'll be doing here, and it's my favorite thing to help someone with. Happy writing :) -Ben

Build Your First Personal AI Agent: A Practical System for Saving Time Without Losing Quality [5/28/2026] (Recording)

After this session, you will know how to design and deploy a simple personal AI agent that handles repeatable tasks without degrading the quality of your output. We will cover how to map your workflow to find the right automation entry points, how to prompt and chain AI tools to act on your behalf, and how to build in checkpoints that keep your judgment in the loop. Attending live means you can describe your actual setup and get a direct answer about where automation fits your specific situation, which a recording cannot replicate. The coach builds and iterates on AI systems as a practitioner, and this session is a rare look at how that thinking works in practice.

Review Hard Text Completion & Sentence Equivalence

Here we will review text completion and strategies as well as sentence equivalence and strategies with additional examples and some new vocabulary.

8 Steps to an MBA app: 1) Life Story, Timeline, & MBA Resume

Applying to business school can feel overwhelming! You have dozens of moving pieces: essays, short answers, video content, resume, recommendations, outreach, research, and more. This workshop is the starting point of a structured 8-part MBA Identity Mapping series designed to take you from fragmented tasks to a clear plan of action. In this session, you will build your foundational Life Timeline of all your key stories and begin transforming your resume into MBA format. These sessions walk you step by step through building one fully aligned MBA application. In every workshop, you will be assigned tasks to complete over the next two weeks, keeping you organized and accountable. By the end, you will have strong, authentic essays and a cohesive narrative that runs consistently through your resume, goals, recommendations, school strategy, and interviews. You are absolutely welcome to attend individual sessions if you only need focused help on a specific component(s) of your MBA application. Event 1 identifies your significant experiences and reshapes your resume into MBA format: • Understand the full trajectory of the 8-phase MBA Identity Mapping process and how each piece connects. • Build a comprehensive Life Timeline that captures the raw material of your life. • Begin transforming your professional resume into MBA format. The MBA Identity Mapping process has guided 100+ applicants into every M7 program, all other top 20 U.S. programs, and leading international programs including INSEAD, London Business School, IESE, Esade, Oxford, Cambridge, NUS, and more. Clients consistently describe it as transformative because it replaces scattered effort with forward momentum and strategic clarity. If you are ready to stop juggling tasks and start building an organized, cohesive MBA application, this is where you begin. (Please message me if you would like a copy of the super helpful free resource mentioned in the video: MBA Resume Transformation Guide.)

Claude Chat vs. Cowork vs Code

There are a lot of options for how to approach tasks using AI. Learn which interface to reach for why one might be more suited to specific tasks than the others.

VC Recruiting Workbook

Template to articulate your unique value proposition and background story for VC recruiting; Evaluate your current track record and identify 3 goals to strengthen your candidacy over the next 90 days.

90-Day Action Plan Template for VC Recruiting

Create a comprehensive 90-day action plan for breaking into VC with your unique positioning.

Home for Ambition #9 — Weekly Live Show [5/13/2026] (Recording)

Home for Ambition is a weekly live show, by Leland, for people trying to stay ahead as work, learning, and opportunity keep changing. Each episode tackles a handful of timely, high-signal topics across AI, careers, education, and the future of work. We expect thoughtful debate, unique perspectives, and practical takeaways you can actually use. It is not a typical interview show or a generic news recap. It is a live roundtable built to help ambitious people make sense of what is changing, understand what matters, and leave with a sharper point of view on how to navigate what comes next.

Starting Your GMAT Journey: An Introduction to the GMAT Focus Edition [5/21/2026] (Recording)

Starting GMAT prep can feel confusing when you’re not sure what’s changed in the Focus Edition or how to begin effectively. This session is for anyone looking for a clear introduction to the GMAT Focus Edition and what it takes to succeed. You’ll learn how the exam is structured, what each section tests, and how to build a study plan that aligns with your strengths and target score. Join live to ask questions about your starting point and get guidance on how to approach your prep with confidence. The speaker is an expert GMAT coach who regularly helps candidates navigate the early stages of studying. They’ll share the patterns they see across successful test takers and the foundational strategies typically covered in 1:1 prep sessions.

Sector Overview: Fintech

Learn about the Fintech Industry, its sub-sectors, key players, valuations, and how VCs approach it

Sector Overview: Crypto & Web3

Crypto has quickly become a huge industry. Check out its key growth drivers, sub-sectors, major players, and what excites VCs.

2026-2027 Wharton MBA Essay Guide

A prompt-by-prompt breakdown of all Wharton essays, with specific tips on what to do and what to avoid. This guide will help take your application from good to attention-grabbing!

The Consulting Recruiting Command Center

Track every application, referral, networking touchpoint, and interview in one streamlined dashboard built for consulting recruiting. This document is part 9 of a broader 9-part consulting interview resource kit.

The Mental Habits of High Performers [5/19/2026] (Recording)

Your thoughts, interpretations, and mental patterns have a direct impact on how you perform at work. Many high-performing professionals experience patterns like overthinking, perfectionism, fear of failure, self-doubt, or harsh self-criticism, often without realizing how much these patterns influence decision-making, confidence, communication, and performance. In this session, we’ll explore how the mind works, how thoughts shape performance, and practical tools to build more intentional and supportive mental habits in high-pressure professional environments. We’ll cover: • How thoughts influence emotions, behaviors, and performance outcomes • Common mental patterns experienced by high performers • Why the mind is wired to detect risk, pressure, and potential failure • A practical framework for questioning and reframing unhelpful thoughts • How awareness creates more intentional responses under pressure • Practical mindset shifts and habits that support stronger mental performance over time You’ll leave with practical tools to better manage your internal dialogue, improve resilience and decision-making, and approach your work with greater clarity, confidence, and intentionality. This session is designed for professionals who want to strengthen their mindset, improve performance, and build a healthier relationship with pressure, growth, and high expectations.

Office Hours with a Senior Software Engineer [5/24/2026] (Recording)

We're going to help you get clarity around these questions: 1. Is software a good fit for the life I want? 2. What does it take to become a software engineer? This will also be an open session to ask a question about software from someone who has been living and breathing it for the last decade. People of all experience levels are welcome!

Sample MBA Interview Answers

A comprehensive library of sample MBA interview responses across every major question category: leadership, teamwork, problem-solving, communication, self-awareness, resilience, ethics, and adaptability. Each example uses the STAR method to show you exactly how to structure compelling, quantified answers you can adapt with your own experiences.

Empowering Your Team / Organization with AI [5/21/2026] (Recording)

After this session, you will know how to build a practical AI adoption strategy for your team, identify where AI creates real leverage in your workflows, and avoid the implementation mistakes that stall most organizations before they see results. We will cover how to assess your team's readiness, choose the right tools for your specific context, and create internal buy-in that actually holds. Attending live means you can bring your specific situation, whether you are leading a small team or a large organization, and get a direct answer grounded in your context rather than a general one. The coach works on AI transformation strategy with organizations regularly, and this session reflects how they actually think through these decisions with clients.

Reaching Out for Recs? Here's How to Make Sure You're Set Up For Success [5/28/2026] (Recording)

Are you gearing up for your MBA applications and wondering how to secure stellar recommendation letters? Join me, Sabrina, for an insightful session on mastering the art of recommendations. With my experience as a Wharton MBA graduate and a member of the student admission committee, I understand the nuances of what makes a recommendation stand out. During this event, I'll share strategies to help you identify the right recommenders, guide them effectively, and ensure your recommendations align with your overall application narrative. Having interviewed industry leaders and held leadership roles at Wharton, I bring a wealth of knowledge to help you succeed. Spaces are limited, so RSVP now to secure your spot and take a crucial step towards your MBA dreams!

GRE Geometry & Algebra: The Top Tips High Scorers Use [5/22/2026] (Recording)

Geometry and algebra questions make up a major portion of the GRE Quant section, but high scorers approach them with specific strategies that go far beyond memorizing formulas. This session is for students who want to improve both accuracy and speed on two of the most heavily tested GRE topics. You’ll learn the shortcuts and patterns top scorers rely on, how to recognize common trap setups, and the foundational concepts that make difficult problems more manageable under time pressure. Join live to see how an experienced GRE instructor breaks down these question types and the patterns they see across high-performing test takers. You’ll also have the chance to ask questions in real time and get practical guidance on how to apply these strategies effectively during your own preparation.