Jamil Hasan: The Incentive Equation
How Jamil is rethinking digital innovation by bringing technology, finance, governance and human behaviour into the same conversation.
A company can spend years building better technology, strengthening its financial systems and putting rules in place, yet still find itself struggling with the same problems. Why? Because systems may determine how people work, but people ultimately decide how those systems are used. When the rewards, pressures and expectations around them pull in the wrong direction, even a well-built system can produce the wrong result. Jamil Hasan came to this understanding through his own career, and it changed the questions he wanted to ask about technology, finance and the way organisations work.
Technology and finance were always intertwined in Hasan’s career. At AIG, he worked at the intersection of financial systems and the technology that supported them, so he initially viewed the challenges he encountered largely through those two lenses. That way of looking at things made sense given his work, but as he explored governance and began writing about some of these ideas in Re-Generation X, another part of the picture became harder to ignore: human behaviour.
Hasan became increasingly interested in incentives. He started seeing how much they could influence the way people behaved and how organisations functioned. A company could have sophisticated technology and carefully designed financial structures, yet misaligned incentives could still undermine the whole system. The reason was deeply human. Systems ultimately depend on people, and people respond to the incentives those systems create.
That realisation changed the direction of Hasan’s work. As Author, Publisher and Founder of Crypto Hipster Publications LLC, he began looking at a much bigger question. Rather than simply asking how to build better technology or more innovative financial systems, he wanted to understand: how could we design systems in which technology, finance, governance, and human incentives worked together rather than against one another?
It is a question that has stayed with him. Much of Hasan’s journey since then has been an exploration of that question and a search for a better way. His work today harbours that same line of thought forward. For Hasan, understanding innovation means understanding the people who live with its consequences, the choices they make and the incentives that form those choices. That is where technology, finance and human behaviour meet.
How AIG Shaped His Thinking
When Hasan looks back at the early part of his career, his experience at AIG stands out as an important influence on how he came to understand financial systems, risk, organisational complexity, and innovation. His experience at AIG taught him that risk is about much more than return on investment, spreads, or the numbers appearing on a financial statement. Those things matter, but they are measurements within a much larger system.
Working inside a large and complex financial institution showed him that risk is ultimately about stewardship. Decisions made within one part of an organisation can affect people and systems far beyond the immediate transaction. Technology can make those decisions faster and financial engineering can make them more sophisticated, but neither eliminates the responsibility that comes with making them.
That understanding became even more important to him as his career evolved. He began to think about risk not simply as something to quantify or minimise, but as something he was entrusted to manage. Capital, technology, institutions, and even information are resources placed in his care.
Innovation therefore cannot simply be about creating something faster, more profitable, or more efficient. The more consequential question is whether he is being a responsible steward of what he builds, what he invests in, and what his decisions leave behind for others.
The Real Shift is Learning How to Explore What Comes Next
For Hasan, the most important technological shift he has witnessed is not any single technology. It is the increasing ability to understand new technologies, have the courage to experiment with them, and remain open to discovering applications that may not have been originally imagined.
He has watched blockchain, digital assets, artificial intelligence, and other emerging technologies develop through periods of enormous enthusiasm, scepticism, failure, and reinvention. What interests him most is what happens when people stop looking at each technology in isolation.
Innovation accelerates when technologies begin to come together, with one extending the capabilities of another, new applications being tested, and ideas that previously belonged to separate disciplines being brought together. That requires curiosity and a willingness to be wrong. As Hasan sees it, people cannot discover very much if they only explore places where they already know what they are going to find.
He believes that mindset will have the most lasting impact. Individual technologies will evolve, some will disappear, and others will surprise people. The ability to explore, combine, create, and expand upon them is what ultimately determines what becomes transformative.
Lessons from 600 Conversations
More than 600 conversations with founders, entrepreneurs, technologists, investors, and independent builders have given Hasan a different understanding of technological and institutional change. He has learned that the most important components are rarely the systems themselves.
Technologies change, institutions change, markets change, and business models change. What stays remarkably consistent are the personal stories of the people navigating them.
He has heard journeys shaped by fear, doubt, grief, perseverance, resilience, adversity, failure, and starting again. Those experiences tell him far more about how change actually happens than any discussion of a particular platform or technology.
Innovation is often described as though it moves in a straight line from an idea to adoption. Hasan sees something very different. There are people inside that process making decisions while confronting uncertainty, setbacks, competing responsibilities, and sometimes profound personal loss. The technology may provide the opportunity, but human beings determine what they do with it.
That has changed how Hasan conducts conversations and how he thinks about innovation. He is increasingly less interested in asking someone what they are building without also understanding why they kept building when there were perfectly reasonable reasons to stop. The most enduring lessons about technological and institutional change are often found in those moments.
A Difficult Personal Moment Became a Reason to Build for the Future
Crypto Hipster Publications grew out of a very personal moment for Hasan. He was dealing with a desmoid tumour, and he realised he had a choice about where he directed his attention. He could climb into a small burrow and contemplate what could have been, or he could focus on recovering from his illness, looking at what was still possible, and building something for the future.
He chose the future.
Publishing became a way of turning uncertainty into creation. Instead of dreading yesterday or worrying about what tomorrow might bring, Hasan could build for tomorrow. The podcasts and books gave him somewhere productive to place his curiosity, experiences, conversations, and ideas while continuing to recover.
Over time, that personal purpose revealed a larger opportunity. Hasan saw tremendous amounts of technology content focused on what was happening right now: prices, products, trends, predictions, and the latest narrative. He became more interested in what might remain valuable after those narratives disappeared.
Crypto Hipster Publications became a way to preserve ideas, experiences, and human stories while continuing to explore what comes next. What began as a decision to look towards the future became an effort to create something that could remain there.
Putting People Before Technology
As an author and publisher, Hasan tries not to begin with the technology. He begins with questions that extend beyond it.
Someone may be building with blockchain, artificial intelligence, or another emerging technology, but Hasan wants to understand the personal journey that brought them there. What experiences shaped their thinking? What problem did they encounter that made them believe something needed to change? What did they learn when an idea failed? What kept them moving when the outcome was uncertain?
That difference is reflected in how he approaches the Crypto Hipster Podcast. Many technology and crypto interviews naturally focus on questions such as, “What does your token do?” Hasan is more interested in asking, “What will you do because you have created your token?”
The first question explains the technology. The second begins a conversation about purpose, possibility, responsibility, and impact.
Those questions create an entry point that does not require the reader or listener to understand the underlying technology first. People may not understand a protocol, an algorithm, or a new financial architecture, but they understand uncertainty, ambition, disappointment, curiosity, failure, and perseverance.
Once that human connection exists, the technology becomes easier to explore because there is a reason to care about it. Hasan is not trying to make every reader an expert in blockchain or AI. He wants them to understand why someone chose to build with it, what they discovered along the way, and what that experience might teach people beyond the technology itself.
Keeping Humanity in Innovation
The human side of technology matters deeply to Hasan because it helps him discover his own humanity and reminds him to remain human.
Technology can expand what people can do, but capability alone does not tell them what they should do, why they should do it, or who may be affected by their choices. Those questions require people to look beyond technology.
The personal journeys Hasan encounters through his work continually bring him back to empathy, responsibility, curiosity, and connection. Innovation is exciting, but he never wants fascination with what people can create to overwhelm consideration for the people who will live with what they create.
The Podcast Became His Classroom
Hosting the Crypto Hipster Podcast changed Hasan’s understanding of education and personal development. For years, he felt that growth required another transformation programme, something like Tony Robbins or Landmark Education, or an executive education course where someone eventually handed him a certificate validating what he had learned.
The podcast changed that.
Hasan realised he was being educated and, in a sense, certified in real time through direct conversations with founders. Instead of studying entrepreneurship and leadership from a curriculum, he was sitting across from people actually building companies, surviving failures, solving problems, and making decisions under uncertainty.
More importantly, he began listening differently. He found himself identifying strengths and positive attributes in his guests and asking what he admired about them. He discovered people he wanted to be more like, because he recognised qualities in how they approached their lives and work that he wanted to develop in himself.
The podcast became his classroom, the founders became his teachers, and the conversations became an education he could never have designed in advance.
Looking Past the Crypto Label
One of the most important lessons Hasan has learned is to stop treating “crypto” as though it were a single investment. Bitcoin is not every digital asset, and every digital asset is not simply another version of Bitcoin. Different networks, technologies, applications, and economic models should be evaluated according to what they are actually designed to do.
That distinction has significantly influenced how Hasan thinks about investing. He wants to understand the individual thesis behind an investment: what problem it addresses, what makes it different, what risks are specific to it, and what role it might play within a broader portfolio. Grouping everything together because it shares the label “crypto” can conceal rather than diversify risk.
What Hasan believes has been overhyped is price as a measure of technological significance. Rising prices can make mediocre ideas appear transformative, while falling prices can make genuinely interesting technologies appear irrelevant. Markets provide information, but they do not provide the entire answer.
For him, the transformative development is the emergence of distinct digital economic systems that can increasingly be evaluated on their own merits rather than simply by their relationship to Bitcoin.
With AI, Curiosity Matters More Than Fear
AI creates fear, and Hasan understands some of it. There is considerable criticism that using AI in the creative process is somehow cheating. He does not see it that way when it is used thoughtfully as a tool for particular functions.
A writer still has to write. A podcaster still has to sit down and have a conversation with another human being. The tool does not eliminate the responsibility of the person using it.
Hasan also believes people have to remember that what comes out of these systems is heavily influenced by what goes into them. AI does not relieve people of the need to think, question, evaluate, and make decisions.
For leaders, the opportunity is to discover where AI can genuinely help rather than beginning from either fear or unquestioning enthusiasm. That requires experimentation.
Hasan does not believe good choices are made from fear. They are made through curiosity. Whatever technology comes next, leaders need to remain curious and teachable enough to explore it, challenge it, understand its limitations, and decide for themselves where it belongs.
The Future May Be Built from Technologies Working Together
Hasan does not believe one technology will reform the future. He expects transformation to emerge from the interaction among AI, blockchain and digital assets, robotics, quantum computing, space technologies, and innovations people may not yet recognise as significant.
He has been testing that idea with his own money. He intentionally built his portfolio as a laboratory, combining crypto with traditional financial instruments, including ETFs and mutual funds representing different technology industries. He treats individual digital assets and technology sectors as distinct investment theses rather than assuming they represent one technology trade.
He has not eliminated systematic market risk, nor would he suggest that he could. What interests him is whether he can diversify idiosyncratic risk within emerging technology. His portfolio has recently exhibited a beta of approximately 1.1 relative to the S&P 500 and 0.9 relative to the Nasdaq. Those numbers are not targets; they are observations from an ongoing experiment.
The larger implication extends beyond his portfolio. At the corporate and enterprise-governance level, Hasan believes diversification within emerging technology will increasingly require a hybrid approach. The future is unlikely to be simply centralised or decentralised. Organisations will need to understand how centralised and decentralised technologies can coexist, complement one another, and distribute different risks.
That is where Hasan believes some of the most interesting innovation will occur.
What He Hopes to Leave Behind
As Hasan continues his work across publishing, podcasting, and emerging technology, he increasingly thinks about it in terms of stewardship and inheritance.
The books, podcast conversations, ideas, experiments, successes, and failures are becoming an archive. He may create that archive, but he does not believe he ultimately owns what others will discover in it. His responsibility is to preserve it honestly, continue adding to it, and leave it in a form that allows someone else to find something useful long after the circumstances that created it have disappeared.
That is what stewardship means to Hasan. People are temporary caretakers of ideas, institutions, capital, technology, and the stories people entrust to them. Eventually, someone else inherits what they leave behind.
He hopes future innovators and leaders inherit more than conclusions from his work. He hopes they inherit questions worth asking, experiences worth examining, mistakes they do not need to repeat, and enough curiosity to challenge the answers he reached.
If they can take something Hasan discovered, combine it with something he never imagined, and build something better from it, then the archive has done exactly what he hoped it would do.
His experience at AIG ultimately gave Hasan a way of looking at innovation that stayed with him as his career evolved. For him, the value of what we build is closely tied to the responsibility we carry for its consequences. Whether the resource is capital, technology, information, or an institution itself, it remains something placed in our care. That sense of responsibility persists to determine how Hasan approaches risk, innovation, and the decisions that leave something behind for others.