Jake Woodhouse

I Made the Money. I Didn't Build the System. (JWP 134)

I spent part of my wife's 40th birthday, on a clifftop that should have been pure celebration, quietly worrying about money. I had built real wealth and then watched a lot of it crumble over the last year. This episode isn't really about that one uncomfortable moment. It's about what it exposed: making money and building financial security are two completely different skills, and I had only ever learned the first.

In this episode, I get into:

The mistake that made it real this year: committing to a big renovation when Bitcoin was high, never actually funding it, and then being forced to sell into the crash just to pay the invoices Why a decision to reallocate is really a decision to sell, and the two separate bets I did not realise I was making at the same time The forced sale you quietly schedule for your future self when you take gains and forget the tax The reframe that changed how I think about income: its job isn't to beat Bitcoin, it's to make sure I'm never forced to sell it The idea of buying permanence, and the harvest paradox I still haven't solved, where the same rule that would have saved me this year would have cost me the upside that got me here

This one carries on from the recent episodes on capital, cash flow and optionality, and lands on a question I'm still sitting with: if I'm this convinced Bitcoin is one of the best assets I'll ever own, why did I build a financial life where something completely unrelated to it could decide when I sold it?

Should We Live Here? (JWP133)

Every time I travel somewhere beautiful, the same question shows up within 48 hours: should we live here? This episode isn't really about Bali. It's about what that recurring pattern actually reveals.

In this episode, I get into:

• Why travel gives you perspective, not just a better holiday, and how it quietly rewires what you assume is "normal"
• The real story of a retired Australian couple I met who built their dream villa in Bali sixteen years ago, and what happened to the view they thought they'd always have
• Why optionality was never meant to be the destination, and what it's actually supposed to buy you
• The line that reframed the whole episode for me: a choice you never make isn't wealth, it's just deferred decision-making with better financing
• Where my family and I are actually heading next, and why the decision is deliberately undramatic

This one ties together the last two episodes on capital and cash flow, and lands on a question I'm still sitting with: at what point does keeping your options open stop being freedom, and start being the thing stopping you from building the life you actually want?

Cash Flow Funds Optionality (JWP 132)

In this episode I break down how a tweet about cash flow, ended up explaining a mistake almost every investor makes on the way up, and only notices on the way down.

Learn why cash flow isn't just boring income sitting in the background, it's what buys you the ability to wait.

I walk through two people with identical net worth but completely different financial lives depending on whether their cash reserve is a reservoir or a stream, why yield looked stupid to me during the bull run and stopped looking stupid the moment Bitcoin fell 60%, and a real story about a holiday with my wife that felt free at the time and expensive in hindsight, plus the pushback from her that reframed how I think about funding lifestyle from cash flow instead of chipping into the capital stack.

I also get into why I stopped asking "how do I maximise my returns" and started asking "how do I maximise my ability to stay in the game."

So I ask you: what would change in your financial life if you stopped measuring it by what you own, and started measuring it by what it produces?

What Is Capital? (JWP131)

What if the biggest capital allocation decision you make today has nothing to do with money?

This week I sit with a moment of total overwhelm, homeschooling, business, investing, all at once, and the workout that pulled me out of it. That leads back to a conversation with Rev Hodl, whose homestead runs on nine interconnected forms of capital, not just financial ones.

We get into why time is a flow you can't bank, why attention is the real scarce resource, and how a single hour, a walk, a workout, reading with your kids, can build several forms of capital simultaneously.

I also talk about extraction: how chasing one account (money, status, output) can quietly drain another, and why that's closer to a definition of burnout than most people realise.

So: where will your next hour be most productive?

Ps - sorry show notes didn't post with the ep again...

Dad, what's a Sixpence? (JWP130)

This episode starts with my six-year-old walking up to me one afternoon and asking, "Dad, what's a sixpence?" I follow that question all the way down.

I dig into the 400-year life of the sixpence, a British coin quietly debased over decades until there was no silver left in it at all, and finally withdrawn in 1980, largely without anyone noticing while it happened. From there I get into what debasement actually looks like in real time, why every generation assumes the money it grows up with is permanent, and why being a good capital allocator means being a student of change as much as a student of markets.

Also covered: the books that have shaped how I think about money (Menger, Lynn Alden, Saifedean Ammous), where Bitcoin fits into this story without being the whole story, and the question I've been sitting with since that conversation: what do I own today that feels permanent, but probably isn't?

Not sure why the show notes didn't post as well...

I Asked Bitcoin To Do Too Much (JWP 129)

Between 2023 and 2025, my Bitcoin position grew so fast I thought I'd solved the wealth problem. Then the market turned, hard and fast, and I found out exactly what I'd built.

Turns out I was asking one asset to be four things at once: my growth, my income, my emergency fund, and my peace of mind. When volatility hit, all four failed together.

In this episode I walk through what actually happened (the renovation, the forced selling, the hardest six months of my marriage) and the framework I'm now using instead: every dollar needs one job, not four.

Growth: Purchasing power over the long run. Income: Money through the front door, however you make it. Optionality: Cash and available capital, your buffer to survive and act. Stability: The base layer you never sell, the thing that lets you sleep.

The mistake wasn't buying Bitcoin. It was the architecture.

If you want to try the exercise: write down everything you own, and one sentence next to each, what job is this actually doing for you. If you can't answer it, you've found the weakest part of your portfolio.

Help pls

My wife is building a health app that’s genuinely private — the kind where the company literally cannot read your data. Not “we promise not to look.” Can’t.

It synthesises your genetics, labs and biomarkers into personalised health guidance, using confidential computing (Maple AI / OpenSecret-style).

She’s hiring a developer with real experience in encryption, secure enclaves, or confidential-compute systems. Non-technical founder, paid work, not a co-founder search.

If that’s you — or you know them — reply or DM 🙏

For some reason I can’t see my latest podcast ep that I published on

via

mobile app

But it’s working on desktop…

Any tips?

Anyone use Obsidian?

Been working on a new product, for personal use, and long term wealth strategy

Think a family office style knowledge base to pass down to the next generation

Something I wish I could have accessed when my dad died

Accrued intellectual capital

It needs to outlast AI models, laptop provider, Gsheets etc

Be private

And the .md file format seems to work very well for this use case

Text files so easy to manage

Will contain investment notes, ROI, mistakes, balance sheet etc

Appreciate any feedback if Obsidian has any pro/con

🙏🏻

The Market Intelligence Report: Version 1 (JWP128)

Early release for all my Nostr friends...

A few weeks ago I sent an early version of my business to 44 people I trust. My main aim: tell me why it wouldn't work. Well over twenty replied. One even told me to get a job. All of it was valuable. What I didn't realise at the time was that I was accidentally building a market intelligence database. This process has fundamentally changed how I think about building Bitcoin Custody Architect.

In this episode I share Version 1 of that report.

What you'll hear:

• Why one opinion is interesting but five independent people saying the same thing is evidence
• How the market moved me from sovereignty to recovery, and from documentation to confidence
• Why multiple people independently pointed me toward financial advisers as a distribution channel I never asked about
• Why the annual review is now part of the core offer, not an afterthought
• Why stories teach better than specifications ever will
• And the biggest lesson from all of it — which had nothing to do with Bitcoin

This is Version 1. I expect it to look very different by Version 10. That's the whole point.

If you have a custody story, a recovery experience, an inheritance challenge, or a mistake you learned from, I'd genuinely love to hear from you. Every conversation improves the next version of this report.

Head to jakewoodhouse.io/bca

Meant to share this on Nostr last week, but it got missed

Could You Recover Your Bitcoin Without Your Provider? (JWP127)

I asked Bitcoin Twitter a simple question this week: if you own meaningful Bitcoin, which worries you more, a 50% price drop, or losing access to it?

Almost everyone said losing access. The thread is worth reading: https://x.com/jakewoodhouseio/status/2069199376166301735

One reply put it simply: a 50% drop means you've lost half. Losing access means you've lost it all.

That's what this episode is about.

I recently reviewed one of my own Bitcoin setups and found a gap. A vault I'd created that wasn't properly documented; specifically the derivation path required to rebuild it independently if my provider disappeared. I've been doing this for over a decade and still found a problem.

That's a provider dependency: when your recovery process depends on a specific company, software, or service remaining available.

In this episode I cover what that actually means in practice: a friend's Sparrow update prompt and why pausing before clicking yes was the right instinct; the AUSTRAC Travel Rule coming into effect in Australia on 1 July 2026; a Ledger that died inside a 2-of-3 multisig and turned it into a 2-of-2 overnight; and the questions every Bitcoiner should be able to answer about their own setup right now.

Self-custody is not a destination. It's a process.

If your family cannot recover your Bitcoin without you, you have a Bitcoin dependency. If you cannot recover your Bitcoin without your provider, you have a provider dependency. Both are worth solving.

jakewoodhouse.io/bca

Putting yourself out there, with ideas, your voice, new concepts, comes at a cost

Peoples opinion

Projection

Some of it is very helpful

Some of it is very unhelpful

Sifting through the emotion, and trying to listen for the real signal, is one of the hardest parts of it

To trying!

To failing!

To trying again!

🙏🏻

Could Your Family Recover Your Bitcoin Without You? (JWP126)

Most people who hear that question feel something shift. Because the honest answer is no. Or maybe. Or they haven't really thought about it.

In this episode I introduce the concept of Bitcoin Dependency, and why it's the most under-examined risk in every serious Bitcoin holder's life. If your family cannot recover your Bitcoin without you, you do not have a Bitcoin custody plan. You have a Bitcoin dependency.

I also share the personal story that shapes everything about how I think about this, my father dying suddenly when I was twenty, and seventeen years of figuring out what to do with inherited capital without a roadmap left behind. That experience is the foundation of what I now build for clients: a Family Bitcoin Plan.

If you're holding meaningful Bitcoin, have a family, and haven't built a plan around your custody yet; this episode is for you.

Book a free 30-minute discovery call: jakewoodhouse.io/bca

USD $4,444 fixed fee. Everything included. Annual review available at USD $1,111/year. Not every application is accepted.

Could your family recover your Bitcoin without you?

Most Bitcoin holders have spent years learning why, how, and when to buy Bitcoin.

Far fewer have spent time preparing their family to recover it if they are no longer there.

If your loved ones cannot recover your Bitcoin without you, your Bitcoin depends on you.

That's what I call a Bitcoin dependency.

You are:

• The password manager • The recovery procedure • The documentation • The inheritance plan • The technical expert

Remove you, and the system may fail.

I believe Bitcoin Custody Architecture is a critical piece of the puzzle for Bitcoin holders looking to build a Family Bitcoin Plan covering:

• Custody • Recovery • Inheritance • Family preparedness

If you'd like to learn more, click the link in my bio.

The proof window I had for the AI Assessment I developed has closed

Data to follow soon

In short: I wont be continuing with it in the current guise

I have a sneaky feeling I am going to launch a bitcoin related offering soon

Can't resist it

All because of an inquisitive Uber driver the other night

Behind the Scenes: Using AI to Build a Real Business in Real Time (JWP125)

Most people using AI are re-writing emails or summarising documents. That's fine. But this episode is about something different — using Claude as a daily operational co-pilot to actually build things.

Over the last week and a half I built two separate marketing funnels from scratch. One organic, one paid. Different audiences, different entry points, different conversion paths. I'm not a software developer. I'm a podcast host running a productised consulting business from Byron Bay, whilst homeschooling three kids.

Every time I hit a wall — a WordPress setting I didn't understand, a DNS record I was terrified to touch, a ConvertKit automation I couldn't figure out, a Linkedin Ad setting I didn't understand — I took a screenshot, sent it to Claude, and got unstuck in minutes.

That's the episode. Not theory. Not a tutorial. What this actually looks like in practice.

What's covered:

• The two-funnel structure: organic (podcast + Apollo cold email → lead magnet → nurture sequence) and paid (LinkedIn ads → dedicated landing page → free discovery call)
• The "screenshot workflow" — the simplest way to use AI when you're stuck in an unfamiliar tool
• Building a lead magnet page in WordPress with no prior experience
• Creating a five-email nurture sequence in ConvertKit, including the automation logic
• The DNS records moment — being told exactly which one not to touch, and why
• Designing ad creative in Canva, setting up audience targeting, and building the landing page for paid traffic
• Why the master thread / sub-thread / project file structure makes every prompt more powerful

Links:

• Download the free AI self-assessment: https://jakewoodhouse.io/self-assessment
• Book your AI Assessment ($999, Report-Pays-For-Itself guarantee): https://jakewoodhouse.io/ai-assessment https://v.nostr.build/XlRsDZzaCHcV9fFk.mp4

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: https://drive.google.com/file/d/1GJqgmEkLwV5Wbb8o_iMTVfuUj4iY5kaV/view?usp=drive_link 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.

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: https://docs.google.com/document/d/1l2NWf_ex_zZ_Nx3cuGdC0ApPyPpmEbVkS83RQ_wtaNE/edit?tab=t.0)

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: [email protected]

The gap isn't access. It's knowing where to start

Who can help Mrs W out?

🙏🏻

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

💪🏻

I guess it’s no surprise that the year AI has proliferated in my life in terms of usage

My book reading habit has slowed down dramatically

ChatGPT updating privacy terms to include ads

Next big digital product market about to kick off

Action leads to clarity

Forgive me Nostr friends - I am doing a 30 day challenge which includes posting a reel a day on IG

Commercial purposes trumping psychopath, cypherpunk, censorship-resistant, radical honesty, and intransigent minority legends

😜

Been building something new the past few days

Feels good

Shedding skins

Learning lessons

Moving forwards

What is Cognitive Sovereignty? - Andi Pitt (JWP 119)

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In this episode of the podcast I was joined by Andi Pitt, a venture capitalist in the Bitcoin space, and former member of a cult. She discusses the concept of mind control, its prevalence in society, and its implications for individual cognitive sovereignty and democracy. This was a truly mind-bending conversation. We discussed cults and mind control, the Iranian regime, education as a tool for indoctrination, the idea of cognitive sovereignty, Bitcoin and personal freedom, VC in the Bitcoin industry today, and finally the impact of meditation with self-awareness. So much to learn from someone like Andi.

Timestamps:

0:00 Introducing Andy and the topic of mind control 0:57 Andy's experience growing up in a cult 5:56 Finding a framework to understand the world 7:19 Do evil people know what they're doing? 12:14 Humans are programmable for survival 15:51 Seeing mind control everywhere 20:08 COVID-19 and global mind control 23:01 Cognitive sovereignty and democracy 33:00 The nuanced role of meditation 44:58 The value of uncorrelated assets

Thanks,

Best Jake

I want to learn how to use OpenClaw so I never have to book a flight again

Most painful process ever

How To Leverage OpenClaw - Roland (JWP 118)

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In this episode I spoke with Roland. He run's me through how he's used OpenClaw, and Bitcoin, to create an open‑source personal assistant, that runs on its own LN‑VPS server, pays for AI model usage via Pay‑Per‑Q, and can autonomously spawn new agents to handle tasks like email, GitHub, and continuous research. He also explains how Alby’s self‑custodial Alby Hub ties all Lightning‑enabled apps together, making Bitcoin the native currency for everyday software. Listeners will learn how to boost productivity, automate workflows, and build Bitcoin‑first products using always‑on AI agents without sacrificing privacy. The future is already here, most just don't realise it yet…

Timestamps:

0:00 Welcome and Roland's Bali Bitcoin Story 1:18 The Rise of Open Claw 3:36 Setting Up a GitHub Account for Open Claw 6:08 Autonomous Agent Onboarding with Bitcoin 11:49 AI as a Tool for Productivity 17:56 AI, Sound Money, and Human Potential 20:05 Open Claw: A Personal, Always-Online Agent 25:40 How Roland Uses Open Claw Day to Day 30:06 Business Models for AI Agents 34:20 Paying for Open Claw and AI Models 37:21 The Open Source Advantage 43:38 Alby's Mission: Bring People to Bitcoin 57:07 Lightning Network Growth and Adoption 1:01:41 Final Thoughts

Thank you

Best, Jake

Wow

👀

1 million seconds (1,000,000 s) = 11.574 days

1 billion seconds (1,000,000,000 s) ≈ 31.69 years

Being a billionaire is a big difference…

You control:

• where you fish
• how many lines are in the water
• whether you show up every day

💪🏻