Leland+ for Startup Founders

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.

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 How Might We Framework for Reframing Problems

Learn what makes a great "How Might We" statement (broad enough for creativity, narrow enough to be actionable, outcome-focused), see examples from Notion and Loom showing insight-to-HMW transformation, and get tips for writing HMWs that inspire your team.

Claude Essentials for Engineers [5/19/2026] (Recording)

Most engineers use Claude like a smarter autocomplete. Type a prompt, read the answer, type again. That's not a workflow — that's just waiting. In this 45-minute live session, I'll show you exactly how I've configured Claude to work in the background while I keep shipping. You'll see my real setup: Git worktrees running parallel agents on separate branches, async notifications that ping me when Claude's done, skills that produce production-quality output every time, and a CLAUDE.md that gives Claude deep context on my codebase without me repeating myself. WHAT YOU'LL WALK AWAY WITH → Git worktrees set up so you can run multiple Claude agents simultaneously without branch chaos → An async notification workflow that frees you from watching progress bars → A reusable skill you can use to get consistent, high-quality output on repeat tasks → A CLAUDE.md file structure that makes Claude immediately useful in any project WHO THIS IS FOR This session is built for engineers at all levels — whether you've never heard of CLAUDE.md or you're already using Claude daily and want to go deeper. Non-technical founders who work alongside engineering teams will also find the workflow principles directly applicable. WHAT MAKES THIS DIFFERENT Everything in this session comes from shipping real projects with Claude. No theory, no slides full of bullet points. I'll be live in my actual environment, showing the tools and configs I use every day. You'll leave with things you can set up in under 30 minutes — and that will still be working for you months from now.

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.

Build Your Personal Brand & Thought Leadership System with Claude + Notion [5/20/2026] (Recording)

Personal branding is your ticket to excelling in the AI age. Most professionals know they should be creating content yet almost none of us do it consistently. Not because we lack ideas, but because we have no system to enable consistency. In this session, we'll build one. Using the network analysis from last week, we'll use Claude to generate a content calendar built around your actual expertise, then turn each idea into multiple formats: a LinkedIn post, a story hook, a networking pitch, and more. Everything lives in a pre-built Notion template you duplicate at the start of the session, so you spend the full session generating content, not building infrastructure. Outcome for attendees: A content calendar tailored to their specific network audience and a reusable Claude + Notion workflow they can run every month independently Session pre-requisites: Claude account & Notion account — free is fine 🙂

From Zero to First Revenue: Bootstrap Growth Strategies That Actually Work

Getting to your first revenue is one of the hardest—and most important—milestones for any startup. This session is designed to share practical, proven strategies for bootstrapping growth and turning an idea into paying customers. Whether you’re launching your first product or trying to break through your initial plateau, you’ll leave with actionable insights and a clearer path to revenue.

From Idea to First 10 Customers: A Playbook

A session dedicated to walking founders through a playbook for going from ideation to landing their first 10 customers.

Cold Emails That Land Warm

Most cold partnership emails fail before the second sentence and it's not because the sender lacks a good product, but because they lead with themselves instead of the person they're writing to. This guide is built from real outreach across nearly two decades of building companies in food, wellness, experiential events, and matchmaking. It covers six partnership types: brand-to-brand, venue and experiential, distribution and retail, media and press, investor introductions, and sponsors and collaborators with two copy-paste templates per section and a bonus section of real emails from actual deals, with breakdowns of exactly why each one landed. Built for early-stage founders sending their first partnership emails. No theory. No generic advice. Just the structure that works.

Home for Ambition #3 — Weekly Live Show [4/1/2026] (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.

Perfecting Your Pitch

After this session, you will know how to structure a startup pitch that clearly communicates traction, differentiation, and ask in the time you actually have. We will cover how to lead with the problem in a way that earns attention, how to frame your market sizing without losing credibility, and how investors typically decide whether to keep listening after the first two minutes.

Home for Ambition #5 — Weekly Live Show [4/17/2026] (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 I Founded, Scaled and Exited my Brand Last Year

Cashmere is the Founder and CEO of Beauty Bakerie, a cosmetics company she built into a globally distributed brand before being acquired by West Lane Capital Partners. Sold in nearly 2000 locations worldwide and backed by more than $15M in venture capital, Beauty Bakerie grew into San Diego’s fastest-growing private company from 2015 to 2017 and developed a strong, multi-platform social media presence with over 1M followers. The brand earned recognition from publications including Allure, Cosmopolitan, Forbes, Good Morning America, Teen Vogue, Essence, Elle, Oprah, and BuzzFeed. As a founder who led vision, branding, product development, and overall strategy, Cashmere has firsthand experience navigating fundraising, hyper-growth, market expansion, and the acquisition process. In this session, she will share key lessons from scaling a consumer brand, building a team, developing products, working with retailers, and preparing for exit. Attendees will gain insight into what drives brand value, how to manage rapid growth, and the strategic decisions that shaped Beauty Bakerie’s trajectory from inception to acquisition.

Home for Ambition #7 — Weekly Live Show [4/29/2026] (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.

Home for Ambition #4 — Weekly Live Show [4/8/2026] (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.

The Growth Blueprint: How to Find, Understand, and Win Customers [5/1/2026] (Recording)

Finding and winning customers is one of the hardest parts of building a startup, and many founders struggle to turn early traction into consistent growth. This session is for founders who want a clearer, more structured approach to understanding their customers and scaling demand. You’ll learn how to identify your most valuable customer segments, uncover the insights that drive conversion, and build repeatable growth loops that actually work. Join live to ask questions about your own product and growth challenges and get direct input from someone who has done it before. The speaker is an experienced startup founder who regularly works with teams on customer acquisition and growth strategy. They’ll share the patterns they see across successful companies and the kinds of frameworks typically discussed in 1:1 working sessions.

The Startup Accelerator Playbook: What Programs Want, Who They’re For, and How to Win

Startup accelerators can fast-track your growth—but only if you understand how to leverage them. This session is designed to explain what accelerators look for, who benefits most, and how to position your startup to succeed. You’ll learn the value accelerators provide, how programs evaluate teams and ideas, and strategies to stand out in the application process. Whether you’re exploring your first accelerator or planning your next step, you’ll leave with clear insights and actionable guidance.

Scaling Startups: Lessons from the Trenches

​In this panel, Arjun S., Daniel M. and Liza M. will share hard-won insights from scaling startups through the messy, high-growth stages. From finding product–market fit and building the right team to raising capital and navigating growing pains, you’ll hear real stories about what worked, what didn’t, and the lessons learned along the way. ​Whether you’re an early-stage founder, part of a startup team, or simply curious about the realities of scaling, this session will give you practical takeaways, candid advice, and inspiration to tackle the challenges ahead.

No Ivy, No Problem: How My Startup Got into Y Combinator

​Think you need an Ivy League degree to make it into Y Combinator? Think again. In this workshop, Chanhyung K.—a Georgia Tech graduate, McKinsey alum, and Y Combinator founder—shares how he built and pitched a successful startup without the traditional pedigree. ​Drawing from his experience landing offers at McKinsey, JPMorgan, and FAANG while coming from a non-target school, Chan will reveal how to craft your founder story, stand out in competitive application pools, and navigate the YC process with authenticity and confidence. Whether you’re an aspiring founder or already building your startup, this session will show you how to turn unconventional beginnings into startup success.