Wayfounder
You’ve built a startup the hard way. Build your next one differently.
You’re building something meaningful — and the weight is real. Wayfounder is ongoing counsel for founders who need a trusted partner to help them see what’s next, challenge what’s not, and stay on course.
New terrain.
New decisions.
Same digital ocean.
The record behind the judgment
Early to things, and on the record.
- 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.
Read the case study
“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. I’d say the best evidence of just how important and successful this rollout had been, was how seamless it all felt when the Covid pandemic hit us. Despite the world going through a difficult time, from a workplace technology perspective we were able to operate remotely without a glitch and Slack was at the heart of it. It certainly was one less thing to worry about …”
The stack you stand on
Whose stack are you standing on?
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 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 optimizing for their business. The mismatch 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.
What you are buying is my judgment: which parts of this are real, which are noise, and which parts you should refuse.
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 recognize what would cause us to revisit it.
The Wayfinder
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 digital business oceans already, rather than reading the waves alone.
Why this relationship
Outside your org chart. Inside the trenches.
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 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.
The name and the longer view
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.
How the work happens
First the picture. Then the rhythm.
We look at what phase you’re in as a founder, how your team, business and market are changing, and what needs attention now — so you can decide what to act on, what to prepare for, and what can wait.
Month one
- Founder interview
A long working session on the company's history, current strategy, key relationships, technology choices and the decisions taking up your attention.
- Business review
I read what I need to understand the situation: strategy, product direction, team structure, the communications that matter, the tools you are running on.
- Conversations with three to five people around you
Private conversations with people who know the business from different angles: a cofounder, an executive, a team member, an investor, a close partner.
- The brief
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.
Ongoing counsel
- Two 90-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.
- Direct communication
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.
Who this is for
Founders at a turning point.
- 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.
“What I admired most about George was his ability to do systems thinking and set up processes for automation and scalability of a company.”
Investment and availability
US$3,000 per month.
Three-month minimum.
Four founders at a time.
The first month builds the picture and the value compounds from there.
That constraint is what makes the work good, so I hold it.
Test the work before committing
A conversation first.
We begin with a free conversation. 30 minutes, no strings. 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.
Track record
Fifteen years where emerging tech, culture and community meet.
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.
- 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. Read the case study ↗
- Bitcoin in 2013. Early to the wave, and among Notion's earliest users.
Explore the full timeline
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 organizations 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.
Read all five named testimonials
These testimonials 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. I’d say the best evidence of just how important and successful this rollout had been, was how seamless it all felt when the Covid pandemic hit us. Despite the world going through a difficult time, from a workplace technology perspective we were able to operate remotely without a glitch and Slack was at the heart of it. It certainly was one less thing to worry about …”
“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.”
Common questions
Before we begin.
Is this coaching?
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.
Is this therapy?
No. The conversations can be honest and personal, and this is decision counsel rather than mental-health treatment or diagnosis.
How much access do I get between sessions?
Short messages or voice notes about live decisions, answered within one business day, Monday to Thursday. Direct communication, not unlimited messaging or emergency availability. Bigger questions wait for a session so they get proper attention.
Can I request an NDA?
Yes, before anything sensitive is shared.
What if I’m located outside of Asia?
That works. I am currently based in Chiang Mai and run sessions across Asia-Pacific, Europe and US time zones.
What happens after three months?
We review what changed, whether Wayfounder is still useful, and what the next phase needs. It continues month to month by agreement.
Let’s talk
What decision are you carrying alone?
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.
Free 30-minute conversation. No strings.
Or book a fit call on Cal.com · book a Clarity Session
4 founders maximum · 3-month minimum · US$3K per month