13 Building your Founding Hypothesis, with Startmate's Ben Simai

Title: Building Your Founding Hypothesis, with Startmate’s Ben Simai

Session context

• Format: Interactive workshop + live Q&A + Miro walkthrough
• Host: Ben Simai (Investment Manager, Startmate)
• https://www.linkedin.com/in/bensimai/
• Source: “Click” by John Zeratsky & Jake Knapp (pre-Design Sprint “Foundation Sprint”)
• Goal: Produce a crisp founding hypothesis you can test with design sprints

Why a founding hypothesis

• Clarity before speed: 48 hours of structured thinking saves months of wandering
• Forces plain language: if a 10-year-old can’t understand it, investors and users won’t either
• Centers learning: makes your assumptions explicit so you can design tests to prove/disprove

Core principles: Foundation Sprint (2 days)

Step	What it is	Notes
Decider + facilitator	One person makes tie-break calls; keep group ≤5	Use “note and vote” to avoid loudest-voice bias
Plain words only	No jargon (“distributed enterprise orgs”)	E.g., “Teams in different locations”
Work alone together	Silent ideation → sticky notes → silent review → voting	Timebox sections (5–15 min each)
It’s a hypothesis	Bold, testable, likely wrong in parts	You will iterate after sprints

The basics (Day 1 AM)

Item	Guidance
Customer	Be specific; pick the segment you know best and are motivated to help
Problem	One “hair-on-fire” problem; top-5 priority for that customer
Competition	Three kinds: direct, substitutes (e.g., spreadsheets), and “do nothing”
Advantages	Capability, Insight, Motivation (C-I-M). Combine into a unique edge you can leverage now

Get real about competition

• “No competition” is a negative signal; switching to you must be worth the pain
• Anchor on the 800-pound gorilla (e.g., Slack vs email) for clearer positioning
• Nike x Jordan story: outmaneuver by reframing differentiators (signature shoe + revenue share)

Differentiation makes products click

Classic scales	Examples
Slow ↔ Fast	“Fast is better than slow”
Hard ↔ Easy	“Just a link” vs install, onboarding friction
Expensive ↔ Affordable	Clear ROI, time-to-value
Siloed ↔ Integrated	Works with tools users already have (Slack, email, calendar)
One-size ↔ Focused	Specific JTBD for a specific user

• Create custom scales where you can be radically better
• Plot you and competitors; if you’re only slightly better, keep iterating
• Two-by-two: pick the two most powerful differentiators; aim to be alone in the top-right; push others into “Loserville”

Principles to speed decisions

• Derive 2 values from your differentiators (boil to one word each) + 1 “do no harm” guardrail
• Turn values into practical principles (advice to a new teammate) that reinforce differentiation
• Example style (Google): “Focus on the user,” “Do one thing really well,” “Fast is better than slow”

Day 2: Options before commitment

• Generate 4–7 alternative approaches (not just your pet idea)
• One-page summaries per option:
  • What it is
  • Why good
  • How it might work (simple sketch)
  • Risks/open questions
• Label each with positive criteria (e.g., “works offline,” “large audience,” “easy to build”)

Magic lenses (evaluate options)

• Lenses: Customer (value), Pragmatic (feasible now), Growth (distribution), Money (unit economics), Differentiation; add custom lenses (e.g., “works in the middle of nowhere”)
• The decider (or domain owner) places each option on each lens scale
• Pick a top bet + 1–2 backups; you’ll test the top bet first

Founding hypothesis template

If we help [customer] solve [problem] with [solution], they will choose it over [gorilla + key competitors] because our solution is [two clear differentiators].

Examples

• Gmail: If we help tech enthusiasts solve overflowing inboxes with Google data center power, they will choose it over Outlook, Hotmail, and Yahoo because our solution is high-capacity and searchable.
• Slack: If we help teams solve communication with searchable chat, they’ll choose it over email because it’s fun and boosts teamwork.
• Google Meet: If we help teams in different locations solve remote meetings with just-a-link video, they’ll choose it over Skype and Tandberg because it’s fast and easy to connect.

Benchmarks and pacing

• Timebox the workshop: ~2–4 hours per half-day; total ≤ 8 hours
• Differentiation bar: aim for “10x” on two axes that customers care about
• Post-workshop: run weekly design sprints (prototype → user tests → iterate hypothesis)

Selected Q&A highlights

Topic	Takeaway
Two co-founders only?	Add 1–2 outsiders (advisor/friend) to avoid tunnel vision; still assign a decider
Jargon vs clarity	Investors won’t speak your domain language; use plain English
Competitor mashups	Include substitutes and DIY stacks (spreadsheets + email + Zapier)
Feature parity first?	Don’t. Start differentiated. Deliver the “sh***iest manual” version of your wedge to test willingness-to-switch
Apply sprint to a single feature?	Yes. Scale the process to 60–90 minutes for sub-problems
PM methods (Agile/Scrum/etc.)	Use whatever accelerates build–learn loops; optimize time-to-learning

8-week execution template (fill this in)

Track	Baseline (now)	2-week goal	Weekly target	Success criteria
Customer	ICP defined; interview pipeline	10+ interviews; validate top-5 problem	5–10 interviews/week	Clear #1 problem; quotes that map to hypothesis
Differentiation	Draft 2×2 + principles	Alone in top-right on two axes	Revisit weekly with learnings	Users echo your two differentiators back to you
Solution	3–5 option summaries	Select top bet + backups via lenses	1 design sprint/week	Users complete golden path; fewer manual patches
Distribution	Channels, gorilla identified	1 landing + 2 value-prop variants	2–3 tests; 10–20 outreach calls	CTR/conv to call/waitlist/preorder hit target
Monetization	Pricing hypothesis	LOIs/preorders or paid pilots	5 pricing conversations/week	Willingness to pay; trial→paid rate meets threshold

Practical metrics you can choose

• Activation: time-to-value, task completion of golden path, “very disappointed” %, qualitative love quotes
• Differentiation: user repeats your two differentiators unprompted
• Demand: LOIs/MOUs, preorders, paid pilots, MRR, # paying customers

Workshop logistics and follow-ups

Item	Details
Template/tools	Miro board (Foundation Sprint), sticky notes, timers; “note and vote” method
Roles	Decider, facilitator, contributors (≤5 people total)
Output	Basics sheet, competitor map, differentiation scales + 2×2, principles, option summaries, lenses, founding hypothesis
Next steps	Run 1 design sprint/week; update hypothesis and 2×2 from user evidence

Your 5 next actions

1. Book a 4-hour block with your team; assign decider; invite one outsider
2. Fill Basics: Customer, Problem, Competition (incl. substitutes/do-nothing), C-I-M advantages
3. Build differentiation scales; iterate until you’re alone in the top-right on the 2×2
4. Generate 4–7 approaches; run magic lenses; pick top bet + backups
5. Draft your founding hypothesis sentence; schedule a design sprint to test it next week