Title: Startup Playbook, with Kate Herbert (ex Startmate Investment Associate)
Session context
- Format: Deep-dive masterclass + live Q&A with slides
- Speaker: Kate Herbert, founder/exited Wagley (pet e-commerce), ex-Startmate Investment Associate, angel investor
- https://www.linkedin.com/in/kate-herbert1/
- Source material: Sam Altman’s “The Startup Playbook” (free online, audio available)
- Focus: Mindset and fundamentals that work across B2B/B2C, bootstrapped or funded
Core philosophy
The goal of any startup: Making something users love
- Not “like” - love
- Love = customers can’t live without it, tell friends, contact you directly, use constantly
- You cannot skip to scale without first achieving love
- Better to have 100 customers who love you than 1M who sort of like you
The 4 core mantras
1. Build something customers love
Key insights:
- All great companies start with great product
- If you fail to make something users love, your startup will fail
- If you deceive yourself about user love, you’ll fail more expensively
- Much easier to scale something people love than something they like
How to know they love it:
- They tell friends organically
- They contact you directly with feedback
- High usage/engagement metrics
- “I can’t live without this” language in interviews
- They get your logo tattooed (Halter cattle fencing example)
Questions to ask:
- Am I solving the customer’s problem or fitting my solution to a problem?
- How do I know if someone loves what I’m building? (Define your north star)
- Do I understand the problem at human needs level, not just surface level?
2. Launch early and continuously
Core principle: Ship bad quickly, iterate to good
- “If you’re not embarrassed by your early product, you launched too late” - Reid Hoffman
- Launch as soon as you have “one quantum of utility” - Paul Graham
- Every feature release = a launch opportunity
Why launch early:
- Get real user feedback vs. theoretical conversations
- 50x more learning in 2 years of 2-week cycles vs. building for 2 years
- Takes you from “what would you do if…” to actual behavior data
What “bad” means:
- Janky UX, limited features, basic design = OK
- Unsafe, data breaches, completely broken = NOT OK
- Can be demo, prototype, or basic version
Reddit example: Paul Graham launched Reddit by linking to it in his blog post without telling founders - forced them to iterate with real users from day one
Questions to ask:
- What’s the most paired-back feature I could launch ASAP?
- What story am I telling myself about why I can’t launch faster? Is this true?
3. Start small
Philosophy: Small segment first, then scale
- Focus on narrow ICP initially
- Much easier to scale something people love than to get millions to love something they like
- Network effects businesses especially need geographic concentration
Facebook example: Started at Harvard only, then expanded university by university Airbnb example: Focused on 100 customers who loved them, founders personally visited every host
Benefits of starting small:
- Easier to identify and meet your ICP
- Can iterate quickly based on feedback
- Passionate early users become your growth engine
- Builds strong foundation before scaling
Questions to ask:
- What’s the most narrow segment of my ICP I can start with?
- Am I truly building with this small segment in mind?
- Could I go even smaller?
4. Do things that don’t scale
What this means:
- Recruit users manually (not through big marketing campaigns)
- Do your own sales and customer service
- Stay close to customer touchpoints
- Don’t delegate anything that creates customer disconnect
Why it matters:
- Builds loyalty through personal attention
- Generates massive customer insight
- Helps you understand what to automate later
- Creates competitive advantage through deep customer knowledge
Stripe example:
- Founders in public chat room providing support
- Every API request emailed to founders
- All error logs generated high-priority founder emails
- Personal outreach to fix issues
Questions to ask:
- Am I speaking to customers enough to have advantage over competition?
- Do I understand customer pain at the deepest level?
- What am I delegating that I should be doing myself?
Real-world application: Wagley case study
Early days (grassroots approach):
- Hassled people at dog parks in Richmond, Melbourne
- Gave free samples, asked for feedback
- Built WordPress site, manually fulfilled orders from pet shop
- Called every customer after delivery
ICP evolution:
- Initial assumption: Wealthy inner-suburb dog owners
- Reality from data: Women in outer suburbs/regional areas, multiple rescue dogs, either no kids or teenage kids
- Key insight: When they niched messaging further (puppy vs. active vs. power products), conversion rate increased 3x
Scale phase:
- Still spoke to 2-3 customers per week at exit
- Used demographic data + qualitative interviews
- Constantly refined hypothesis based on data
Common founder challenges addressed
“Should I test two ICPs simultaneously?”
- Pick one, go deep, measure results
- Can pivot if wrong, but spreading thin prevents achieving “love”
- Use access/pain level to choose between options
“How many beta testers do I need?”
- Quality over quantity - better to have smaller group of true fans
- Focus on learning, not hitting arbitrary numbers
- Network effects can multiply small initial group
“What about 6-month development gaps?”
- Challenge: Can you descope to ship something smaller sooner?
- Use prototypes/wireframes to validate before building
- Test development partners with smaller projects first
Immediate action items
-
Audit your current approach:
- Score yourself on each mantra (1-5)
- Identify biggest gap between current state and playbook
-
Customer love assessment:
- Define your north star metric for “love”
- Interview your most engaged users
- Ask: “What would make this 10x better for you?”
-
Launch readiness:
- What’s the smallest thing you could ship this week?
- What story are you telling yourself about why you can’t launch faster?
-
ICP focus:
- Can you narrow your target segment further?
- Where does your most narrow ICP actually hang out?
-
Customer proximity:
- What customer touchpoints are you delegating that you should own?
- When did you last have a 1-on-1 conversation with a user?
Key resources
- Sam Altman’s “The Startup Playbook” (free online)
- NotebookLM for creating AI mentor from the content
- Kate’s contact: Available for founder mentoring/advice
Bottom line: These fundamentals haven’t changed despite AI/no-code tools. Your competitive advantage comes from going deeper on customer love while others focus on shipping fast without purpose.