Ongoing counsel for founders
An outside mind for the decisions you carry alone.
Founders reach a point where the decisions stop fitting in one box. A technology choice changes the product. The product changes the team. The team changes the culture. A hard season at home changes how you lead.
The people around you care, and they also hold a position. Your team wants clarity. Your investors want confidence. Your cofounder has a view. Friends know you well and do not know the business well enough to challenge you.
I am one person outside that system who holds the whole picture, remembers what happened, and tells you plainly what I see.
01 · The stack you stand on
Whose stack are you standing on?
The loudest voices in your industry are selling you a stack right now: a model, a subscription, a workflow, a way of working with someone else’s assumptions already baked in.
They are not being cynical about it. They are optimising for their business. Their stack and your natural stack are rarely the same thing, and the mismatch does not show up on the invoice. It shows up in how your team makes decisions, what they stop questioning, and which parts of the company quietly start running on someone else’s logic.
Reading these waves early and translating them into plain language is what I do. What you are buying is my judgment: which parts of this are real, which are noise, and which parts you should refuse.
02 · Wayfounder
A Wayfounder is a founder trained by a Digital Wayfinder.
Like me (Siosi). A Digital Wayfinder reads digital terrain and finds a way through it. That has been my work for years: reading emerging technology early, translating what it means for the people who have to act on it, and helping them carry the change for the long term.
A Wayfounder is a founder who learns to work in such a way — trained into it by someone who has crossed the ground already, rather than reading the terrain alone. You keep building and deciding. I keep the read: what has changed, what is noise, and which way the substrate is moving.
The name carries my ancestry. I am part Polynesian, so my wayfinding ancestors crossed open oceans without fancy instruments, reading waves, winds, and stars to hold a course other people could not see. I am now focused on helping others do the same, for the digital world.
For now, I am the only “Digital Wayfinder” here. Wayfounder takes four founders at a time, forty-four in all. In time there will be others, trained the same way, working the same way, so this becomes a way of working rather than one person’s client list.
03 · Month one
Month one builds the picture.
A long working session on the company's history, current strategy, key relationships, technology choices and the decisions taking up your attention.
I read what I need to understand the situation: strategy, product direction, team structure, the communications that matter, the tools you are running on.
Private conversations with people who know the business from different angles: a cofounder, an executive, a team member, an investor, a close partner.
A written summary: what appears to be happening, the tensions worth addressing, the decisions being delayed, the shifts worth watching, the assumptions that need testing, and the clearest focus for the next ninety days.
Founders and teams experience the same company differently. These conversations show where the stories diverge, what is hard to say to your face, and how your direction is actually landing. I report patterns rather than attributing comments.
04 · The rhythm
Then the rhythm.
- Two 75-minute sessions a month
Bring the decisions that are hard to make alone: direction, a cofounder tension, hiring, positioning, a technology bet, the gap between what you sense and what you can explain.
- Considered access between them
Short messages or voice notes when a live decision cannot wait. I answer within one business day, Monday to Thursday. This is access to a thinking partner rather than an emergency line.
- A short decision note each month
What was decided, what is being tested, what we are watching, and the next moves that matter. Your reasoning stays on the record instead of disappearing into calls.
- Introductions when they are genuinely useful
If I know an operator, an investor or a specialist who can help, I will offer the introduction. They are never sold or guaranteed.
The value compounds because I remember. I keep the decisions, relationships and tensions around the company, and notice when the same pattern returns in a different form.
05 · Fit
Who this is for.
- You are moving through a real transition.
- You carry decisions that affect more than the business.
- You want someone who can think across technology, people and culture at once.
- You would rather be disagreed with than agreed with.
- You want an ongoing relationship rather than a one-off report.
- You will let someone look at the company from more than one point of view.
I work outside your org chart, so I have no internal position to protect. That is what makes it possible to name the tension the people around you cannot.
It matters most when other people rely on you for answers and you have few places to think out loud without performing confidence.
06 · What enters the room
Bring the decision beneath the visible problem.
- Is this emerging technology real enough to bet on?
- Why does the team agree in meetings but fail to act?
- Has the company outgrown the way we currently lead it?
- How do I bring people with me without weakening the direction?
- What am I seeing that I cannot yet explain clearly?
- Have we spent a year cutting costs and calling it progress, without actually growing?
The goal is not to manufacture certainty. It is to understand the situation well enough to make a clean decision, and to recognise what would cause us to revisit it.
07 · Investment and availability
US$3,000 per month.
Engagements have a three-month minimum. The first month builds the picture and the value compounds from there.
I work with only a handful of founders at a time. That constraint is what makes the work good, so I hold it.
Cash is the standard arrangement for Wayfounder. For a small number of companies where conviction is unusually strong, and my contribution goes beyond counsel, I will propose an advisory-equity component. That is discussed separately, with clear terms, and never used as a substitute for the monthly retainer.
08 · Track record
Early to things, and on the record.
I keep turning up in new technology before it becomes the obvious choice, and other people noticed the same pattern.
- Developer first. I started as a programmer, so I can hold the technical conversation.
- Two companies built, one exited. The second took investment from Tim Draper.
- Slack's first enterprise customer in Asia-Pacific. I brought Slack into IRESS, a $1.9 billion fintech.
- Government of Tuvalu. Advised on digital-nation strategy and the national digital ledger.
- Bitcoin in 2013. Early to the wave, and among Notion's earliest users.
2010
Officially sponsored and featured by Adobe
For “Tales From Nanumea”, my first animation venture.
2013
Bought my first Bitcoin
Working in and around Bitcoin while most people were still deciding whether it was serious.
2017–18
Got Slack their first enterprise customer for APAC
I introduced Slack to IRESS, a $1.9 billion fintech company, then helped with the global rollout for ~2K employees across 5 continents.
2018
Bitcoin Cash Fund
Community and adoption work for a Bitcoin fund, in a market moving fast in every direction.
2019
Launched first company
Founded Faiā in Singapore, working on how organisations take on new technology, starting with blockchain communities.
2020
Got investment for second company from Tim Draper
Won a global pitch competition during the pandemic and took backing from U.S. VC Tim Draper for a web3 platform called Honā.
2022
Bitcoin Association
Community and adoption for an international standards body in a fast-moving industry for Bitcoin.
2023
Tuvalu National Digital Ledger
Advised on digital-nation strategy and the national digital ledger — blockchain infrastructure built for a sovereign state.
Now
AI adoption
The same question again at a larger scale: what is real, when to move, and who carries the change.
The testimonials below come from the work Wayfounder is built on — the Slack rollout at IRESS, the Bitcoin Association, Draper Startup House.
“George has been working in community for a long time, and is one of the first people I knew who saw the opportunity in web3.”
“He is a visionary, often seeing trends and opportunities before others. If you want to know what tech platforms will be big in the future, ask George — he has his finger on the pulse.”
“Thanks to George’s thought leadership and drive, Slack was rolled out across IRESS in 2018. It completely transformed how we communicated in the business. George spearheaded the whole initiative and ensured he had the full support of our Exec team, which is so important when driving change and seeking adoption.”
“He has a wide knowledge of industry trends and emerging tools, and an ability to translate this into how these can be used to drive business growth.”
“What I admired most about George was his ability to do systems thinking and set up processes for automation and scalability of a company.”
09 · Why me
Fifteen years where emerging tech, culture and community meet.
The record above is the paper version of it.
New technology enters through one person’s conviction, and it lasts when the people around that person learn to carry it. Every line in that record is the same story at a different scale: someone moved early, and a group had to be brought along. That is the same work I do with a founder, one person at a time.
I also write It Will Come, a personal newsletter on emerging tech waves, cultural patterns, and other unconventional signals I notice.
10 · How we start
One conversation first, then one paid session.
We begin with a free conversation. 30 minutes, no strings. Tell me what’s changing, what decision is in front of you, and why the people already around you cannot fully help you make it. If it isn’t a fit, I will say so and point you somewhere (or to someone) better.
If you want to test the work before committing, there is one session for US$500: a 60-minute Clarity Session with a short written decision note afterwards. If Wayfounder begins within thirty days, the fee is credited toward your first month.
11 · Common questions
Before we begin.
No. This is trusted advisory and counsel, and I am more direct. I will ask questions when they help, and I will tell you what I think when I have a view.
No. The conversations can be honest and personal, and this is decision counsel rather than mental-health treatment or diagnosis.
No. I am not accountability coaching, a fractional executive, or a delivery team. I work on the decisions; you and your people do the executing.
Short messages or voice notes about live decisions, answered within one business day, Monday to Thursday. Considered access, not unlimited messaging or emergency availability. Bigger questions wait for a session so they get proper attention.
Because founders and teams experience the same company differently, and the gap between those versions is usually where the real problem lives. The conversations are confidential and I report patterns rather than attributing comments.
Yes, before anything sensitive is shared.
Yes. I am currently based in Chiang Mai but run sessions across Asia-Pacific, Europe and US time zones.
We review what changed, whether Wayfounder is still useful, and what the next phase needs. It continues month to month by agreement.