I Ran My $999 AI Assessment On Myself — Here's What I'm Doing (JWP124) I sell a $999 AI Assessment to Australian small businesses. Last Thursday I ran it on my own business — same call, same interview questions, same Claude prompt, same Gamma report, no shortcuts. The report told me to do something I hadn't seriously considered: cold email outreach to Australian accountants using a tool called Apollo, with my own self-assessment PDF as the proof piece. Something that wasn't even on my radar a week ago, just this morning at 9am, fired out it's first batch of 10 emails. Honest point: I don't know if it works. Two weeks left in the proof window to find out! The entire report — the exact PDF a paying client receives — is linked below. Read the self-assessment:

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Woodhouse Media AI self-assessment.pdf

Book an AI Assessment: jakewoodhouse.io/ai-assessment Timestamps 00:00 — Ran the product on myself last Thursday 01:30 — The product: $999, 20-min call, 48hr bespoke PDF, Report-Pays-For-Itself guarantee 06:00 — Did the interview on WhatsApp in the car, on the way to pick up my daughter 08:00 — Four pain points the report flagged 11:30 — The recommendation I didn't see coming: Apollo + Claude 12:30 — Why standard hourly-rate maths doesn't fit a productised service 16:00 — Building Apollo Friday/Saturday: 3,346 verified accountants, three-touch sequence 17:30 — Monday 9am: first 10 emails out. One I sent twice by mistake. 19:30 — Honest uncertainty: I don't know if any convert 22:00 — Why pay $999 if the PDF is free? Template is the format. Product is the bespoke version for your business. 27:00 — Ideas have never been cheaper. Execution has never been more important. 28:00 — "You've got to do paid ads" — what if you're amplifying the wrong thing?

Mike Tyson: "Everyone has a plan until they get punched in the mouth." What I feel like vs 12 months ago Bear market a humbling process

The AI Stack I'm Running From Home With Three Kids and No Team (JWP 122) Three months ago, at 4am, my net worth had just halved. Bitcoin had crashed and I'd been heavily exposed. Three kids asleep upstairs, wife asleep. I sat at the laptop and typed one question into ChatGPT: how do I make money? That rabbit hole became the AI Assessment business I now run, and it became this episode. This is the actual workflow. The system I copied from my wife. The verification layer that handles AI hallucination. The exact stack producing this podcast — and why I cancelled Buffer this morning. Why the next decade of business building looks nothing like the last one. And the real numbers from real clients: Pete the chartered accountant, $17,400 a month found in a 20-minute call. Mat the landscaper, $1,500 a month sitting in his invoicing alone. If you run an Australian business and you've known for a while that AI matters but haven't really started — this is for you. Chapters 00:00 — Welcome 00:33 — 4am, three kids asleep, one question 02:15 — Who this is for 02:35 — Why February changed everything 04:35 — The system I copied from my wife 07:30 — The verification layer (AI hallucinates) 09:45 — The founder journey at 10x speed (vs Entrepreneur First) 12:00 — Rod Bishop: solo founder, no CTO, no VC 13:10 — Why bespoke beats generic 15:30 — Sam's boxing gym 17:30 — The Johnny lighting story 19:00 — The stack (Dale asked) 23:00 — Why organic content first 26:30 — What this means for you (Pete and Mat) 28:30 — Outro Resources mentioned AI Assessment: jakewoodhouse.io/ai-assessment Tools: Claude, ChatGPT, Perplexity, Riverside, Opus Clip, Higgsfield AI, Gamma Books: Zero to One by Peter Thiel; The Hard Thing About Hard Things by Ben Horowitz Entrepreneur First (talent-first accelerator) Previous episode with Rod Bishop on the Jake Woodhouse Podcast Call to action If you run an Australian small business and want clarity on what AI could actually do for you — book an AI Assessment at jakewoodhouse.io/ai-assessment. 20-minute call. Bespoke report in 48 hours. $999 with a guarantee it pays for itself in month one. If it doesn't, full refund.

Building myself a workflow that will compress the time it used to take a producer and editor of my podcast by 10x All due to AI

Action leads to clarity... View article →

What I Learned Assessing 5 Australian Businesses for AI in 10 Days (JWP 121) Ten days ago I sent an SMS to my warm network offering a free AI Business Assessment. Five business owners said yes. By Friday, I'd run five 20-minute calls, delivered five custom AI roadmaps, and identified between $1,560 and $17,400 of monthly value waiting to be unlocked. Lewis, a construction and landscaping director in Melbourne, replied: "What once felt overwhelming now feels exciting." This episode is the story of those 10 days — the SMS that started it, the five calls, the numbers, and the offer that's now live at: http://jakewoodhouse.io/ai-assessment Chapters: - 00:00 — Lewis testimonial - 02:00 — Why I paused The Durable Man - 04:30 — The Deloitte stat that flipped a switch - 06:30 — The SMS experiment - 09:00 — The five calls - 14:00 — The numbers - 17:00 — The system: Zoom → Claude → Gamma - 19:30 — The offer & the guarantee - 22:00 — The Rova experiment and AI slop - 25:00 — Final thoughts & how to take this up In This Episode: - Why I paused The Durable Man and what my wife saw that I didn't - The Deloitte Nov 2025 stat that flipped a switch (1 in 3 Aussie businesses don't know where to start with AI) - The 60-word SMS that got an extraordinary reply rate - Five businesses, five roadmaps: - Mat (landscaping) — automating labour metrics on invoices - Lewis (construction & landscaping) — AI for design mockups - Paul (retail) — winning back time for marketing across 300 suppliers - Tom (mould inspection) — compacting 12 hours of reporting - Pete (accounting) — $17,400/month of billable time leaking into admin - The system: 20 min Zoom → Claude → Gamma → 48-hour PDF - Why the report pays for itself in month one (and why I'll refund if it doesn't) - The Rova experiment and why human stories still beat AI slop The Offer: AI Business Assessment — $999 AUD - 20-minute Zoom call - Bespoke PDF report delivered within 48 hours - Two tiers in every report: 4 low-hanging-fruit you can implement this week, 3 longer-term projects worth scoping - Report-Pays-For-Itself guarantee — full refund if the monthly ROI identified doesn't exceed the cost Book yours: http://jakewoodhouse.io/ai-assessment Links & References: - Via this gdoc:

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JWP 121 - episode links

What I Learned Assessing 5 Australian Businesses for AI in 10 Days (JWP 121) Episode references and links: IG reel - https://www.instagram.com/p/...

Take Action: 1. Run an Australian business? Book a call at http://jakewoodhouse.io/ai-assessment 2. Know someone who would benefit? Forward this episode. Connect: - Web: http://jakewoodhouse.io - Email: hi@jakewoodhouse.io The gap isn't access. It's knowing where to start

When things move, they can move fast… - Weekend: studied a report by Deloitte on AI adoption in Australia, which stated 1 in 3 small businesses had no idea where to even start with AI - Monday: sent 20 or so sms to warm network with Hi xxx, How are you? I'm launching something new and want to test it on people I trust first. It's a free AI Business Assessment — you get a personalised report showing exactly where your business should start with AI and which tools will move the needle. Takes 20 mins of your time, normally $1k, free for my first few. Let me know if that’s of interest? Thanks Best, Jake - Tuesday: hosted and recorded 4x calls - Wednesday: created 4x reports, with the transcripts, bespoke to their scenario, and all recommending 4x “low hanging fruit” options, and 3x longer term AI implementations, and sent over - Thursday: already received 1x testimonial “Working with Jake was exactly what our business needed. As a construction company, the idea of implementing AI felt daunting and we had no clear starting point. Jake took the time to understand our operations and delivered a detailed roadmap outlining the right AI tools for us and a clear, step‑by‑step plan for integrating them. What once felt overwhelming now feels exciting, and we’re confident about bringing AI into our business.” Friday: aim is to finalise an offer, landing page, and pricing The future: - website update - podcast episodes to produce - direct outreach - ads All whilst homeschooling, renovating, and organising a trip… Sending good vibes all. A relaxed evening on the sofa badly needed! 😅

My wife just created an npub 💪🏻

Yday I stumbled upon a marketing channel that has never before been available to small business owners I am calling it “content to call” It leverages the latest forms of AI, and delivers cost effective leads, of much higher quality 👀

What a few weeks of iteration I’ve been through… - small business acquisition from a boomer - digital productisation of your life lessons - AI implementation opportunities Trial. Error. Trial. Error. Trial. Error. Always iterating Key lesson: the humanistic leverage one’s relationship with their wife enables is huge Let’s see where it goes Ps - pod on pause whilst this process plays out 🙏🏻