Andrew Masanto
Tell us briefly about you and what you are up to right now.
1. You’ve successfully built and scaled multiple ventures – what’s the common thread in all of them?
Going against the herd. I chase the feeling of doing things which are obvious to me, but that others find odd, weird, difficult, offensive or outright wrong. Every venture I’ve started had a sense of “this is something people might not agree with but I think is right”, and that’s exactly why I knew it was worth doing. For example, internet marketing in 2008, bitcoin in 2011 or NFTs in 2017.
Going with the consensus view seldom creates anything worth remembering. You can’t just be non-consensus though. You have to be both contrarian/non-consensus, and right. If you are contrarian and wrong, you’re dead.
Photographed by Erica Bergsmeds
2. What’s the most underrated skill an entrepreneur needs to build a billion-dollar company?
Timing. Knowing *when* to strike is everything. You can have the right idea, team, and execution plan, but if your timing is off, it’s going to take a lot longer and be a lot harder work, typically requiring pivots. The underrated skill is being able to read the landscape and feel when it's the moment to act. The way you get this is obsession of your craft.
3. How do you balance innovation with practicality in business?
Innovation starts with vision, but it only matters when it meets reality. I balance the two by treating big ideas like puzzles—breaking them into doable pieces. Each practical step moves the dream forward without losing its essence. In other words, take practical steps towards big visions.
Photographed by Erica Bergsmeds
4. What’s a contrarian belief you hold about entrepreneurship that most people disagree with?
Great businesses don’t start with solving a problem – they start with a weird obsession or ego in a person who is driven. The “solve a problem” advice is for people who want to feel safe and understood. No unicorn was built on safety. Note that this may be different for a non-unicorn / smaller company.
5. If you had to start over with no money but all your knowledge, what’s the first thing you’d do?
I’d immerse myself in emerging tech—AI, biotech, or quantum or spatial computing—and build in public. I'd create content, network, and start something with no-code tools or open-source infrastructure. The key is speed of execution paired with understanding of where attention is headed.
Photographed by Erica Bergsmeds
6. You’ve been deeply involved in blockchain and AI. How do you see these industries evolving in the next decade?
I see blockchain moving beyond just payments. It will increasingly integrate into other sectors like secure data (e.g. what we’re doing with Nillion), art (NFTs), tokenization of real world assets etc. Over time these industry sub-sectors will grow and this expansion hold untapped potential, despite the recent skepticism / downturn. AI, on the other hand, is becoming a generational tool—like the internet once was. It will open huge doors for wealth creation, value building, and will redefine how we work and live, especially as it improves. Imagine the difference in our lives between slow, dial up internet, to what we have now? This mirrors the difference in both performance and impact between the AI we have now and the AI that will be created in future.
7. What’s the biggest misconception people have about crypto and Web3?
That it’s easy to make money and everything is ‘get rich quick’. That might have been true in the early days, but now, succeeding in Web3 requires deep expertise. You have to live and breathe the industry. Like any other domain, success in Web3 demands commitment, insight, tenacity and resilience.
8. How do you approach assessing new tech trends – what signals tell you something is worth investing in?
I look for contrarian narratives and somewhat irrational behaviour. When intelligent people can’t explain why they’re obsessed, I take notice. There’s usually a spark there. I also look for emotional resonance and early cult-like communities, which may be controversial. These are early signs that something special is brewing beneath the surface.
Photographed by Erica Bergsmeds
9. How do you see AI impacting entrepreneurship and investment in the coming years?
It will be easier to be an entrepreneur. AI and robotics will reduce the need for both blue-collar and white-collar human resources, which will dramatically lower the barriers to entry. This will shift the opportunity landscape for entrepreneurs in a major way. AI will make execution trivial. Vision and communication will be the critical factors.
10. What daily habits or mental frameworks have been the most transformative for your success?
Complete and utter obsession and focus about whatever I was doing—whether it was a company, a project, or anything else. That obsession transformed everything else in my life to align with achieving that goal.
Photographed by Erica Bergsmeds
11. Many people struggle with self-doubt – how do you stay confident in your decisions?
Confidence isn’t the absence of doubt or fear; it’s the commitment to act in spite of it. I know I may get it wrong sometimes and that’s perfectly fine. Once you stop caring what others think you liberate yourself to do what you enjoy and what you believe in.
12. How do you handle failure, and what’s a major failure that ultimately helped you succeed?
I failed at fitting in when I was younger. My whole life, I wasn’t the archetype people expected – Asian kid + creative in a conservative system. That rejection became fuel. It taught me that if the game is rigged, move to a different playing field and focus on building your own arena.
Photographed by Erica Bergsmeds
13. If you could teach a masterclass on one topic unrelated to business, what would it be?
How to live iconically, although I admit this is a lifelong pursuit that I am still learning and striving for myself. It’s very related to the art of living your life.
14. How has your relationship with money changed over time?
Money used to be about safety and how to prove my worth. Now, it’s about self-expression, but not in a showy way. That’s not my style. My style is rather in a ‘this is a way I want to live my life’ way.
15. What does “success” mean to you beyond financial wealth?
Freedom to do things with the people you want to do them with. I feel like you are always serving others – humans are social creatures so that makes sense. Also I feel that work can give you purpose. However, ‘success’ is being able to work with people I know and love and doing things that I enjoy.
16. Do you think billionaires have a responsibility to give back? If so, how do you approach philanthropy?
Responsibility? No. Power? Yes. And eventually the money will flow back into the world, whether by the billionaires or by their children, or just over time. Ideally, the way they made it was also additive to the world, although I know this is not always the case.
Photographed by Erica Bergsmeds
17. If you had to distill your life’s work into one core mission, what would it be?
Help other people.
Photographed by Erica Bergsmeds
18. Who or what is your inspiration?
Contrast. The tension between darkness and light. Between the monk in me and the rockstar in me. I’m inspired by the edge, always.
19. What’s the most fun project you’ve done and why?
Founding ANONA. It let me express art. It wasn’t about profit, it was about piercing people’s spirit. Making something so beautiful that people could get lost in the fun.
20. What’s the weirdest thing that’s ever happened to you while working on a project?
I closed a multimillion-dollar deal in a hospital bed when getting my blood cleaned through INUpheresis as part of a longevity routine. The doctor had to hold the phone to my ear as I couldn’t use my arms.
21. What’s the most interesting thing you’ve read or seen lately?
ChatGPT o3 (although I wouldn’t be surprised if by time of publication this is eclipsed by something even greater). Try asking it to ask you 10 questions that challenges the strategic decision making of your life, based on what it knows about you from your question history. It’s amazing.
22. What do you like doing in your spare time?
Learning new things, working on cool side projects and spending time with people I enjoy.
23. What is the one item you can’t live without?
Nucalm patches and a nice bed.
24. What’s your most annoying habit?
I problem solve everything. I guess it comes with having been responsible for millions of dollars and hundreds of employees in the companies I co-founded. Sometimes I have to remind myself that I can’t solve everything and also, that I sometimes just have to ‘let things happen’, adopting a bit more of a “C’est La Vie” attitude.
25. What would you like to be remembered about you?
That I helped other people get what they want, en masse. See: https://www.entrepreneur.com/en-au/entrepreneurs/the-millionaire-maker-how-serial-entrepreneur-helps-others/454432. Also, but of lesser importance, that I changed the world for the positive via all of the companies I created.
26. Where are you in 5 years?
Living my best life. I’m currently defining what that is.
27. What is next for you?
I won the game of money and health. I figure I should focus on the game of relationships, along with doing cool things and making people around me happy. Also potentially starting a family? Who knows.
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Photographed by Erica Bergsmeds
Magazine Credits
Photography by Erica Bergsmeds