Ashwin Raj, CEO of LeafLink – Interview Series

As the U.S. cannabis industry reaches unprecedented sales figures, the need for businesses to maintain strict financial and operational order is critical to avoiding potential regulatory and legal disasters. Fortunately, for licensed and heavily regulated operators that must diligently track seed-to-sale data, innovative platforms now exist to streamline this complex information.

To better understand these technologies, MyCannabis.com spoke with Ashwin Raj, CEO of LeafLink.

What were the most interesting and/or useful subjects that you studied during your MBA program at Harvard? How did going to such a prestigious business school provide you with advantages during your very illustrious career?

I was incredibly fortunate to attend Harvard Business School (HBS) and be part of such a distinguished alumni network. Coming from an engineering background, nearly every subject was fascinating because it opened up an entirely new world. The most challenging was economics, which didn’t come naturally at first, but learning to think analytically about markets was invaluable.

What I found most engaging were the strategy courses, particularly corporate and business strategy, and understanding how companies make decisions in complex, real-world situations. I was also at HBS during the early days of the internet boom, when courses on startups, venture capital, and scaling companies were being introduced. That environment was exhilarating.

The biggest advantage of attending such a prestigious institution is the network. Learning alongside people from incredibly diverse backgrounds and maintaining those relationships over time has been one of the most valuable and enduring aspects of the experience.

What were some of the most crucial roles you held with Visa? Since mobile payments were one of your main focuses, how did you see the technology for mobile payments change over your years at Visa?

I joined Visa in 2002 because of its forward-looking vision. During my interview, a product leader described a future where most payments would happen on mobile devices, long before smartphones even existed. That vision immediately drew me in.

I worked on early mobile and contactless payment technologies, running pilots in places like South Korea and Japan. At the time, there were no standards, so we spent years testing and refining technologies until NFC eventually emerged as the global standard. That development process took well over a decade, but today it’s what powers Apple Pay and Google Pay, and it’s incredibly rewarding to see something I worked on become part of everyday life.

I also built what is now called Visa Direct, originally known as the Original Credit Transaction, which enables funds to be pushed directly to a card. That technology now powers payouts for gig platforms like Lyft, Uber, and DoorDash (DASH ), as well as international remittances and peer-to-peer payments.

How did the 2008 recession impact your duties at Visa, and what did that experience teach you about navigating very difficult times?

The 2008 recession put significant pressure on banks, Visa’s primary customers. Banks were facing new regulations, rising costs, and reduced consumer spending. As a result, they looked to Visa for new products and services that could help offset those pressures.

Rather than simply cutting back, we focused on fundamentals, making our partners more efficient and helping them create new revenue streams. I later experienced something similar, but even more severe, during the pandemic at Lyft, when ride demand collapsed almost overnight.

Both experiences reinforced that downturns are temporary. The key is to focus on core value, strengthen fundamentals, and continue to serve customers well. Companies that do this emerge stronger, and I believe the cannabis industry is now approaching that inflection point.

What were some of the biggest professional highlights and milestones you celebrated with Amazon (AMZN ) and Lyft? How did you revamp and strengthen the payment systems for all their platforms?

At Amazon, I joined during its evolution from a first-party retailer to a massive third-party marketplace. I worked on payment systems that enabled one-click shopping both on and off Amazon, making the experience as frictionless as possible. One particularly exciting initiative involved integrating online and in store shopping. Customers could select items online, try them in store, and leave without checking out, with everything handled automatically in the background.

Amazon’s leadership principles, especially customer obsession and deep problem solving, profoundly shaped how I operate as a leader.

At Lyft, the scale and complexity were completely different but equally exciting. I helped build core systems that supported Lyft’s IPO, improved unit economics, and eventually led the entire rideshare business as a public company. I have to credit the amazing teams that supported my product direction and vision and some of the key achievements were enhancing the ride experience with Priority Pickup, changing the way Lyft drivers got paid in real-time and got access to free banking accounts and services with Lyft Direct, enhancing safety for riders with automated check-ins, emergency support, and enhanced verifications, making our maps best-in-class with real-time data updates.

What were the deciding factors that led you to join the LeafLink team? As someone who’s worked with such juggernaut companies before, did you have any professional concerns about working for a cannabis technology company?

What drew me to LeafLink was the opportunity to apply everything I had learned and also continue to learn – building marketplaces, scaling platforms, and developing financial infrastructure, in an industry that is still in its formative stage. That kind of opportunity is rare.

While cannabis is highly regulated and has some stigma associated with it, that perception is changing fast. I did the due diligence talking to family, friends and advisors to seek their input and their feedback was instrumental in helping me decide. The mission to build trusted infrastructure, and support operators who are navigating an incredibly complex environment and evolve the industry to becoming mainstream resonated deeply with me.

From your experience with the company, what are the most significant ongoing issues that LeafLink solves for cannabis companies, especially on the wholesale side?

LeafLink solves many of the core marketplace and operational challenges licensed cannabis operators face on a daily basis.

On the wholesale side, we connect businesses through our platform. Retailers can access brand product catalogs in one place, manage inventory, and showcase products to a wide network of retailers. This eliminates the need for managing individual one-to-one connections with every retailer, and avoids manual processes such as maintaining spreadsheets, text threads, and email chains. This saves operators hundreds of hours each year.

We also take pride in simplifying seed-to-sale compliance. Our integrations reduce unnecessary manual steps, redundant data entry, and compliance risk. This enables businesses to operate with confidence.

Our financial services modernize banking and payments for cannabis sales and provide businesses with the reliable and secure banking infrastructure needed to operate efficiently. These tools were built with the industry’s unique regulatory challenges in mind.

At the core, LeafLink brings clarity, compliance, and efficiency to the cannabis commerce experience, and positions businesses to focus on what matters most: producing best-in-class products and delivering excellent customer experiences.

How does your vast experience with major companies such as Lyft and Visa come into play with your role as CEO of LeafLink? What previously successful strategies from those roles did you bring with you to LeafLink?

My experience at Visa, Amazon, and Lyft taught me how to build large scale platforms, drive adoption in complex ecosystems, and stay relentlessly focused on customer value.

At LeafLink, I’ve brought that same mindset. Focus on fundamentals, build trusted infrastructure, invest in network effects, and create products that truly solve real world problems. The strategies that worked at scale in fintech and mobility, such as customer obsession, operational efficiency, and ecosystem thinking, translate directly to cannabis.

What are some notable ways in which working for a cannabis technology company like LeafLink is different from working for companies not at all affiliated with cannabis?

The most significant difference is the regulatory complexity. Cannabis operates under a patchwork of state laws with limited federal clarity, which impacts everything from payments to logistics to compliance. This requires a level of adaptability and precision that doesn’t exist in most other industries.

At the same time, the industry is still early, which means there’s an opportunity to shape standards, infrastructure, and best practices in ways that weren’t possible in more mature sectors.

As the multibillion-dollar cannabis industry expands into new states and territories, how does LeafLink plan to evolve and expand alongside those new markets? How will LeafLink best adapt to the various changes in state-by-state regulation that have and will occur?

LeafLink is built to scale alongside the industry. We focus on creating a flexible, compliant platform that can adapt to new regulatory environments as states legalize cannabis. We start early by offering our learnings and insights to regulators and early entrants to ensure that each new geography is best positioned for success. We enable our marketplace and financial services to integrate seamlessly into the requirements of the new markets while maintaining compliance and operational efficiency and maximize success for all participants.

By continuing to invest in infrastructure, partnerships, and compliance capabilities, we aim to grow with the industry, not ahead of it, but in step with it.

How do you envision the federal rescheduling of cannabis changing the operations of both your clients and LeafLink as a whole?

Federal rescheduling has the potential to significantly improve the outlook for our operators. If finalized, rescheduling would likely make 280E inapplicable, allowing state-licensed cannabis businesses to deduct ordinary expenses (rent, payroll, etc.) on their federal taxes. This would lower effective tax rates across the industry and free up billions for reinvestment, business expansion, and long-term financial stability. It could also reduce barriers to scientific research and encourage additional states to pursue cannabis reform.

While rescheduling would be a significant step forward, additional federal reforms will still be needed to create true parity between cannabis and other industries. Expanding access to capital and financial services, establishing a framework for interstate commerce, and ending federal prohibition are required to support the growth and sustainability of the market.

Thank you for joining us, Ashwin! For more detailed information on LeafLink, please visit its website.