Leland+ for Startup Founders

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.

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.

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.

Jobs to Be Done Framework Reference Guide with Multi-Industry Examples

Reference guide covering the JTBD formula, real-world examples across B2B and B2C companies (Spotify, Peloton, Slack, HubSpot, Figma, and more), and quick tips for applying JTBD thinking to your startup. Use this to understand the framework deeply and see how different companies address different jobs for different customer segments.

How to Conduct Useful Customer Discovery Interviews

Learn the three-act interview structure (Context, Deep Dive, Future State), the golden rule of customer discovery (listen, don't pitch), and powerful JTBD questions that uncover real problems. Get specific guidance on what to ask and the five mistakes to avoid, from leading questions to interviewing only friends.

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.

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 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.

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?

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.

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.

Bootstrapping Versus Fundraising for Startup Founders

One of the biggest decisions every founder faces is how to fund their startup—should you bootstrap or raise capital? In this workshop, Angela C.—a Stanford entrepreneurship instructor and founder of Stanford’s Education Entrepreneurship Hub—will walk you through the pros and cons of each approach and how to determine what’s right for your business. ​Having bootstrapped her own SaaS startup to users in 80+ countries and coached hundreds of first-time founders, Angela will share frameworks for evaluating funding strategies, building sustainable business models, and pitching effectively when you’re ready to raise. Whether you’re launching your first MVP or scaling toward growth, this session will help you make smarter, more strategic funding decisions.

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.

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.

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.

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.

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.

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.