Leland+ for Startup Founders

Home for Ambition #1: Staying Ahead in a Changing World [3/18/2026] (Recording)

In this first episode of Home for Ambition, we’re diving into one of the biggest questions facing ambitious people right now: what’s actually changing in the world of work, learning, and opportunity, and what should you do about it? We’ll unpack where AI is truly creating leverage, which skills are becoming more valuable, what people are wasting too much time on, and how to stay ahead as the rules keep shifting. — Home for Ambition is a show from Leland for ambitious people trying to stay ahead as work, learning, and opportunity get rewritten. Each episode tackles a few important questions shaping careers, education, AI, and the future of opportunity, then breaks down what’s changing, what’s overhyped, what matters, and what to do about it.

Founder Playbooks: Growth Strategies for Early-Stage Startups

Building an early-stage startup is an exciting but daunting journey, especially when it comes to driving sustainable growth. From finding product-market fit to scaling operations and building the right team, founders face countless decisions that can make or break their trajectory. ​In this session, Renato V. (Founder and CEO of Parallel), Angela C. (Founder of Stanford’s Education Entrepreneurship Hub and Founder of instructiv) and John K. (Founder and CEO of Leland) will share proven playbooks for navigating the critical growth stages. You’ll gain practical insights on refining your go-to-market strategy, attracting customers, raising capital, and avoiding common early pitfalls so you can build a strong foundation and accelerate your path to success.

Map and Activate Your LinkedIn Network with Claude [5/13/2026] (Recording)

You have hundreds of LinkedIn connections you've never done anything with. In this hands-on session, we'll turn your exported LinkedIn data into a working professional CRM in Notion — no automation tools, code, or technical setup required. Using a Claude prompt, we'll categorize your top contacts by relationship tier, industry, and relevance, then drop everything into a pre-built Notion template so you know exactly who to reach out to, when, and what to say. You'll also get a read on what content resonates with your specific network, which feeds directly into what we build in the next session. Pre-work: Request your LinkedIn connections export at least 24 hours before the session (Settings → Data Privacy → Get a copy of your data). LinkedIn emails it within 24 hours and it only takes 2 minutes to request. Outcome for attendees: A populated Notion CRM with their top LinkedIn contacts categorized into tiers, a suggested next action for each, and a content resonance analysis showing what topics will actually land with their network. Session pre-requisites: Claude account & Notion account — free is fine 🙂

Home for Ambition #6 — Weekly Live Show [4/22/2026] (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.

Term Sheets 101 - For First Time Founders

Are you a first-time founder navigating the complex world of venture capital and fundraising? Join me for "Term Sheets 101" where we'll demystify the essentials of term sheets and equip you with the knowledge to confidently engage with investors - decoding the term sheet so you don't get burned on your first raise. By the end of the event, you'll understand valuation, dilution, liquidation preferences, and protective provisions - which are all critical terms that affect your company for years. With a background as a Stanford entrepreneurship instructor and founder of Stanford’s Education Entrepreneurship Hub, I've guided numerous entrepreneurs in securing their first term sheets and then scaling their ventures nationally >> globally. My experience spans founding, operating, investing, and ecosystem building, providing a comprehensive perspective on entrepreneurship.

Term Sheets 101 - For First Time Founders

Are you a first-time founder navigating the complex world of venture capital and fundraising? Join me for "Term Sheets 101" where we'll demystify the essentials of term sheets and equip you with the knowledge to confidently engage with investors - decoding the term sheet so you don't get burned on your first raise. By the end of the event, you'll understand valuation, dilution, liquidation preferences, and protective provisions - which are all critical terms that affect your company for years. With a background as a Stanford entrepreneurship instructor and founder of Stanford’s Education Entrepreneurship Hub, I've guided numerous entrepreneurs in securing their first term sheets and then scaling their ventures nationally >> globally. My experience spans founding, operating, investing, and ecosystem building, providing a comprehensive perspective on entrepreneurship.

The Eisenhower Matrix Tracker by Leadershap

This matrix helps you prioritize work. Here is the google sheet link to the file so that you can use it for yourself: https://docs.google.com/spreadsheets/d/168LA44T7FjjGnUf9sD3LeSDgEnq8GsEN8cvVqBPe7zM/edit?usp=sharing

Stop Firefighting: 4 Strategies to Reclaim Your Time and Scale Your Startup

In this session, you will walk away with a repeatable system for identifying which tasks only you can do versus what should be delegated or eliminated. You will learn how to build decision-making frameworks that prevent constant interruptions, and how to structure your week so that growth work stops getting crowded out by operational noise.

Home for Ambition #8 — Weekly Live Show [5/6/2026] (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.

How Might We Framework Summary Guide

Reference covering what HMW is, how to write HMW statements step-by-step, good vs. bad examples with explanations, common mistakes to avoid (prescribing solutions, being too vague, ignoring research), insights for creating your own HMWs, and validation checklist. Use this to turn each key insight into 2-3 different HMW framings and select the most inspiring ones.

What is Customer Discovery?

Learn the core principles of customer discovery, why it's the foundation of successful startups, and how it differs from market research or user testing. Understand why founders must lead discovery themselves and common myths that lead entrepreneurs astray.

The Jobs to Be Done Framework

Learn what Jobs to Be Done means, how to write effective JTBD statements using the three-part formula, and see real examples from companies like Notion, Airbnb, and Spotify. Understand why knowing the "job" reveals your real competition and transforms how you think about your product.

Customer Discovery Interview Guide: Questions, Structure & Best Practices

Complete interview reference guide with all key questions organized by interview stage (context, jobs to be done, future state), red flags vs. green flags to watch for, and preparation checklist. Use this before every interview to stay focused on learning truth rather than seeking validation.

Synthesizing Interview Discoveries into Useful Insights

Learn how to consolidate interview data, identify patterns (problem, solution, pain point, language, and buyer patterns), prioritize insights using frequency × urgency framework, validate your JTBD statement with real customer language, and make three critical decisions: Is this worth solving? What's the MVP? Who do we build for first?

Founder Playbooks: Growth Strategies for Early-Stage Startups

Building an early-stage startup is an exciting but daunting journey, especially when it comes to driving sustainable growth. From finding product-market fit to scaling operations and building the right team, founders face countless decisions that can make or break their trajectory. ​In this session, Renato V. (Founder and CEO of Parallel), Angela C. (Founder of Stanford’s Education Entrepreneurship Hub and Founder of instructiv) and John K. (Founder and CEO of Leland) will share proven playbooks for navigating the critical growth stages. You’ll gain practical insights on refining your go-to-market strategy, attracting customers, raising capital, and avoiding common early pitfalls so you can build a strong foundation and accelerate your path to success.

Early Stage Startup Fundraising Panel

​Raising capital is one of the biggest challenges early-stage founders face—and one of the most misunderstood. In this panel, you'll hear about the experience of Alaina H., Angela C., and Nick V., all of whom have gained wisdom and insight through their own entrepreneurial endeavors. ​We’ll cover what makes a compelling pitch, how to build relationships with investors before you need funding, what terms to watch out for, and how to decide whether fundraising is the right path for your startup. Whether you're preparing for your first round or just curious about how the process works, this session will give you real-world insight and actionable advice to navigate the fundraising journey with more clarity and confidence.

8 Make or Break Founder Decisions

​Every startup journey is filled with tough choices—but some matter more than others. In this session, expert coach and founder Angela C. will walk through the eight critical decisions that can determine whether your company scales successfully or stalls. Drawing on firsthand experience and lessons learned, she’ll share practical advice you won’t find in a textbook. ​Whether you’re still refining your idea or actively scaling your venture, you’ll leave this session with clarity on which decisions to prioritize, how to approach them, and how to avoid the pitfalls that trip up many founders.

Interview Synthesis Guide: From Data to Decisions

Step-by-step synthesis guide covering the 5-step process (consolidate, identify patterns, prioritize, validate JTBD, decide what to build), pattern-finding questions to ask across interviews, priority framework matrix, common synthesis mistakes to avoid, signs you've done good synthesis, and an action plan.

How Might We Examples: 12 Companies Across B2B & B2C Industries

Comprehensive examples guide showing Meh → Better → Best HMW progression for 12 real companies across diverse industries: EdTech (Udemy), Personal Finance (Mint), Wellness (Headspace), Food Delivery (DoorDash), Fitness (Peloton), Collaboration (Slack), Sales (HubSpot), Recruiting (Lever), Analytics (Mixpanel), Customer Success (Zendesk), DevOps (GitHub), and Finance (Brex). Each example includes the customer insight, three HMW versions with explanations of why each works or doesn't, and industry-specific patterns.