Not every founder ask is created equal — and in this episode, JDM, Cameron, and Cass go full Judge Dredd on a series of startup scenarios.It’s time to play: Reasonable Ask, or Fantasy Land?✅ How to tell if your fundraising ask is realistic or just vibes and a dream✅ Why “more money” is not automatically “better money”✅ How bad milestone planning sabotages your future funding rounds✅ Why B2C freemium + no paying users = 🚩🚩🚩✅ How to create a realistic friends and family raise that actually moves you forwardAlso: JDM brings...
Not every founder ask is created equal — and in this episode, JDM, Cameron, and Cass go full Judge Dredd on a series of startup scenarios.
It’s time to play: Reasonable Ask, or Fantasy Land?
✅ How to tell if your fundraising ask is realistic or just vibes and a dream
✅ Why “more money” is not automatically “better money”
✅ How bad milestone planning sabotages your future funding rounds
✅ Why B2C freemium + no paying users = 🚩🚩🚩
✅ How to create a realistic friends and family raise that actually moves you forward
Also: JDM brings the math hammer down hard, Cameron invents “fundraising inertia,” Cass declares war on startup moats made entirely of vibes, and all three struggle not to sound like disappointed parents. (Spoiler: They fail.)
Key Takeaways & Red Flags
🚩 Scenario #1: The “Freemium Fantasy”
* 400 signups, 40 weekly users, zero paying customers
* B2C with no clear monetization path
* Asking for $1.5M to… vibe harder?
* Verdict: Red light. Full fantasy land. 🌈🧚♂️
* Advice: Learn how to activate, monetize, and prove traction before raising serious money.
🚩 Scenario #2: The “Pilot Paradox”
* 1 paid pilot at $5K
* 7 companies in pipeline, none closed yet
* Asking for $2M to build an enterprise version and get 20 customers
* Verdict: Red light. Amateur hour. 🛑
* Advice: Close real customers first. Prove repeatability. THEN think about bigger raises.
🧂”More capital isn’t just more freedom. It’s more future pain if you’re wrong.” – JDM
🚦 Scenario #3: The “Waitlist Wonder”
* 1200 email signups over 3 months
* No product launched yet
* Asking for $750K to build V1 and get 10K users
* Verdict: Yellow light… with a LOT of caution. ⚠️
* Advice: Use a friends & family round wisely. Build tight, validate ruthlessly, and raise your proper pre-seed later.
Frivolous Thoughts
* JDM: A rogue woodpecker is committing vehicular vandalism in Massachusetts and frankly, I respect the hustle.
* Cameron: Living in remodel purgatory with no kitchen, no alone time, and no end in sight. #PrayForCam
* Cass: If your moat is “vibes,” your woodpecker is about to break your windshield. 🪶🚗
✨ New Sponsor Alert!
This episode of Zero to Traction is sponsored by the Traction Lab Venture Accelerator and their new Founder Community.
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit zerototraction.substack.com
