The Lyft Playbook for Cannabis: Building Trust Through Tech ft. Ashwin Raj

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Bryan Fields: What's up guys? Welcome back to another episode of The Dime. I'm Bryan Fields. With me as always is Kellan Finney. And this week we've got a very special guest, Ashwin Raj, CEO of LeafLink. Ashwin, thanks for taking the time. How are you doing today? Ashwin Raj: I'm doing great, Bryan. Thank you for having me here. Bryan Fields: Excited to have you here. Kellan, how are you doing? Kellan Finney: Doing really well. Grateful to get the chance to talk to Ashwin today. How are you, Bryan? Bryan Fields: Yeah, I'm stoked. Before we hopped on, I was picking his brain on what it was like joining the company, what he was thinking, coming from the tech background and some of the areas he's been in. I can only imagine what those early days must have felt like, kind of what the differences are between what he expected versus what the reality is. So before we get into all the fun stuff, Ashwin, can you give a quick background about yourself and how you found your way to the cannabis space? Ashwin Raj: Thank you again for having me, Bryan, Kellan. It's great to be on your show. I've been using your podcast to onboard and learn about the cannabis industry, so you guys are doing an amazing job — thank you for that. My background, as you mentioned, is primarily from the tech industry. I grew up as an engineer and product manager, and I love all things tech. In my prior experiences I've had the opportunity to be part of financial services and marketplaces. I've worked for some amazing companies like Visa, Amazon, Lyft, and most recently, prior to LeafLink, EzCater. Each of them very unique in their own respects, and each has evolved into market leadership. I've been lucky enough to be part of that journey, and here I am, hoping to transform and take LeafLink forward as the cannabis industry evolves. I'm really excited about that. Bryan Fields: So what specifically about LeafLink caught your eye? Was it always going to be cannabis — were you always thinking about cannabis? Take us through that thought process of making that decision and moving forward with LeafLink. Ashwin Raj: Great question, and to be honest, cannabis was not on my list. I've always been very interested in industries that are emerging and evolving, and being part of transforming them has been something I've really enjoyed — going through that learning cycle and evolution. Simple example: when I joined Lyft, ride sharing was not what it is today — it was actually illegal. We had a wall with all the cease and desist notices from all the states. So how do you join such an industry, how do you navigate it, how do you build products and capabilities? Today everybody takes ride sharing for granted — you push a button and a car shows up wherever you are. Nobody blinks an eye. Being part of that transformation has really helped me think through what I want to be doing in my career. Cannabis is an extremely amazing and unique space — it's got regulatory challenges, financial constraints, and so on, but this industry is going to evolve and grow. There's no 'if' about it, just a question of 'when.' It's up to us as participants to bring about that evolution at a faster pace, working with regulators and partners. For me to be part of LeafLink, which has this amazing B2B marketplace and financial services — two critical issues the cannabis industry faces — being part of shaping that evolution was extremely compelling. It didn't take very long to say yes to it. It's only been 100 days and I'm enjoying every minute of it. Kellan Finney: Just thinking through your background and your role, there had to be some thought process of, okay, there are regulatory challenges, but just because they say no today doesn't mean we're going to be deterred — maybe there are stigmas, like not getting into a taxi, but we think these things will evolve. Were those some of the same similarities you saw with cannabis? Ashwin Raj: For sure. When I was growing up, cannabis was completely illegal. Now I live in California, and cannabis and cannabis products are much more socially accepted — you see it in social get-togethers as a standard, in various form factors. I've seen in my own life how cannabis has progressed and come to be accepted, and I think the rest of the country and the world will follow that process. I feel super confident this is going to happen. There's a parallel with alcohol as it evolved since Prohibition and moonshine — even 20-30 years back you couldn't see alcohol advertising on TV or social media, only in trade magazines, but now big brands advertise and talk about alcohol content and people understand that. I actually feel cannabis is a better product than alcohol — it's healthier, and it can be consumed in multiple form factors. So the potential for cannabis is much larger than alcohol to become part of society and usage. Bryan Fields: Taking the step forward — so you're preparing for the role. How do you assess where to start, where the gaps are going to be, because you're drinking from a fire hose? Take us behind the scenes on how that thought process works. Ashwin Raj: You're obviously going to get fed information based on existing platform capabilities and so on, but I've always found this to be a fact, and something that worked for me in all my prior experiences: listen to the customer, pure and simple — they will tell you the truth, no matter what it is. So my first ask to the team was, put me in front of customers, I want to talk to them and listen to them. One of the things I found about the cannabis industry is that people are just so amazing and welcoming. They're really, really nice. Yes, you have quirky characters, but people are unbelievable. Initially they hesitate to give you the real download on things, but that goes away in a couple of minutes and they'll say, here are the things that need to change. For me, listening to customers and connecting the dots is how I formulate what we as a company need to do. This holds true for any industry and any leader coming into a position — listen to your customers, hear what they have to say, there'll be good and bad, make sure the good is supported and go fix the bad. Then the next is your own team — you need to build that relationship, understand what your team is telling you. The sales team will tell you customer issues, the product team will tell you technology considerations, the people team will tell you what the organization needs. As a leader, one of the most important tasks is listening — understanding what you're being told, then formulating a plan. Within my 90 days it's been intense, and we've taken some quick actions with our customers, just because I heard what they had to say and said, okay, we need to act fast. Bryan Fields: I'm glad you brought that up, because that's a challenging moment — when you joined, the company had communicated price hikes and the industry wasn't happy about it. You're new to the role, getting in front of customers, and the first experience is 'hey, not happy about this price hike.' Was it something you recognized quickly once you got there, or did you have a feeling before you even started that you'd have to make that switch? Ashwin Raj: It was post me joining. I didn't come in with any preconceived notions of what was right or wrong. I said, I'm going to trust the consumers — the company made certain decisions based on certain facts, and the facts weren't incorrect; they made a pricing change based on how marketplaces traditionally operate. So I thought, that makes sense, but let me validate it. When I talked to a lot of customers, they said, listen, we're not unhappy about the quantum of pricing, we're unhappy about the unpredictability and inconsistency of it. That was the bigger issue, and our industry is financially constrained in a way where that unpredictability is hard to deal with. Then you have to determine: is this an issue only in certain states, or consistent across the entire country? When you reach out and talk to customers across different states and hear the same message consistently, you know a decision needs to happen. Then it's about when you make that call, because there is an impact — I always believe you accept your mistakes quickly and move on, because that's what customers appreciate. So we made a very quick decision to change pricing back to a flatter fee structure, and we simplified it. Previously we had three tiers; we made it two — Starter and Pro. Don't complicate things with segmentation — give them predictability and consistency. It's been amazingly well received; I've heard directly from customers that they appreciate it. As a leader, taking ownership, accepting the mistake, correcting it, and working with them to put new pricing in place that meets their needs — that's how you earn trust. Bryan Fields: That's a great breakdown of understanding the true root cause and putting a plan in place where customers feel comfortable. Ashwin Raj: Absolutely, and I think that's the way you earn trust. We had lost a little trust with our customers by making that pricing change without proper input. Going forward, whether it's pricing or product improvements, my articulation to my team and customers is: we will listen to you, we will only build and deliver capabilities that you want, not what we think is right for the market. That's the philosophy I follow as an individual, and I want that same philosophy to apply to the company. Kellan Finney: How do you balance competing desires from different customers — say one big client wants this, another wants that, and they don't mesh well? Ashwin Raj: This is the classic challenge you face in any industry. Obviously larger customers have the clout and pay the bills significantly, so their asks matter. But you evaluate whether, if you build it for them, it can scale across other customers, or if it's so bespoke it only works for them — in which case you try to solve their need but build it in a scalable way. It might not be an exact match, but that's the compromise you arrive at. Primarily, I believe what larger customers ask for will work for medium and small customers too, just enabled differently. I don't think there's usually something so out of whack that it doesn't make sense, though I've seen some really crazy requests. It's a classic product prioritization exercise — you hear your customers, look at all their asks, see what others are asking, and determine what you're going to build in terms of breadth and depth. Bryan Fields: You made that sound so logical when in actuality it's so complicated and layered. From an experience standpoint, are you spending your time a little on everything, or working specifically on product roadmap and strategy? There's only 24 hours in the day. Ashwin Raj: Totally, and at different points in time it's the need of the company that determines how a leader spends their time. In my first 30-60-90 days, I was hoping to get a better understanding of the longer-term strategy, but with the pricing changes and the need to move quickly, that took an overwhelming amount of my focus. We needed to get it right, because you can make one mistake but not two. Now I'm shifting focus — I trust the team to execute, so let's think through the longer-term strategy and roadmap. I'm working with teams on how we think ahead into 2026 and beyond, fitting into strategic pillars. As a platform, LeafLink is straightforward — it's a marketplace, and then there's banking and financial services. In the marketplace, it boils down to selection: do you have the best selection retailers can access, and can operators and brands put their selection on the platform? Then order management, sales management, inventory management, etc. On the retail side: do they have easy access to branded products? And finally the underlying experience — technology and operations. Customers have told us we're great at order management, but they need help with inventory management, for example. I'm setting up a three-year horizon for the team to think through, not just 2026, because these products take time to build and time to ramp up. Bryan Fields: And are those pillars supported by current resources, where you can assess if a team is short-staffed or overweight and needs to shift people? Ashwin Raj: Absolutely — that's resource mapping to strategic priorities. Take inventory management: we may be able to do that with existing resources. But take hemp, for example — hemp is now getting regulated differently in different states, and we're an entity that allows licensed operators to participate. If we want to expand selection in a state where only licensed operators can sell hemp, that may need more resources. Those are decisions based on timing, market conditions, and your own growth plans. Bryan Fields: Is there an area you prefer to operate in — one you find more enjoyable or fulfilling? Ashwin Raj: It's tech. I love the product and technology side of things, I love building it. One of my biggest challenges, having been a product manager, is I now have to actively not be a product manager and let the team figure things out — that's so difficult for me. I'm itching to get in there, but I have to be the right leader and guide the team rather than jump in myself. Even with inventory management, I'm thinking about how to make the merchandising look better, the display look better, put the right content so people can make quick decisions. My head is constantly with these thoughts, much to my life's unhappiness, but I enjoy it — this is what attracted me to cannabis, being able to build a whole set of products and make this industry so much more efficient. Bryan Fields: I think when you're talking to customers and hearing their problems, you're internalizing it from a product standpoint — they're really saying they need a feature more readily available because it exists, they just don't know it. This industry is so new that connecting these pieces can accelerate growth in areas LeafLink maybe wasn't prepared for or wasn't publicly known before. Ashwin Raj: Completely right, and I'll give a good example. A lot of our customers have told me, hey, we're large enough that we're thinking about an ERP system, but ERP systems from SAP and Oracle are so costly and expensive that in our industry it just doesn't work — can you help with that? I'm not going to build them a full ERP system; I ask, tell me what the problem is you want to solve. It comes down to something simple like procurement — connected to their warehouse, stocking of inventory, stockouts, replenishment. That's a more tangible problem, and then you think about how to help with that rather than going head-to-head with SAP or Oracle. Bryan Fields: But that's a slippery slope too — you take a few steps and next thing you know you've built a full ERP suite without really meaning to. Ashwin Raj: True, and maybe our industry needs a lower-cost ERP system — regulated industries with margin compression issues could benefit from that. Who knows how it evolves. Here's something I've learned from tech: don't come in with preconceived notions, let the customers and market tell you what's working and what's not. Banking is a good example — banking has existed for hundreds of years and people do it really well, but in our industry banking doesn't work well because of compliance requirements, checks, and reporting, so there's a very high cost — often 5x-10x what an SMB in a traditional industry would pay. LeafLink did an acquisition last year, Dharma Financial, a pure-play cannabis banking provider, and they've solved compliance verification, cash management, and created a card product for purchases. Over time this may settle and become on par with traditional banking, but right now the industry needs someone to solve for it. Bryan Fields: Is it difficult to show the value of pairing stacks together when a customer says, we're already doing this, why should we change? Ashwin Raj: That's part of the challenge, and that's where you need to showcase the value of each stack and how they'll benefit. You do this at the time of ideation, not after you've developed the product — engage with them before you even start, ask what they want solved, what solution they use today, how this can make it better, and have continuous engagement. This is an enterprise play — you share a concept, get feedback, share a PRD, get feedback, do a beta launch, get feedback, then continuously improve. That's what our industry needs, and the customers are in that process with you. For smaller customers, LeafLink used to have product forums where we'd bring customers in, share developments, share ideas, and get feedback — those forums are how you get the industry involved in product development. Bryan Fields: That makes sense, and sometimes it takes longer to communicate operational efficiencies because change is hard to quantify — there's friction of 'we've always done it this way and it's worked.' Ashwin Raj: Totally, and habit is actually the biggest hurdle to overcome. A product might be crappy, but if you're used to it, you don't want to change — people react negatively to change more than anything else. That's why you see free trials — companies are trying to create behavioral change. LeafLink has an embedded base of customers using elements of our platform, so asking them to try an added feature shouldn't be as difficult as starting from scratch. There's a benefit to having an embedded customer base, and they know you're a partner who brings newer products and offerings. There are 'friendlies' willing to engage regularly to test things out, and then word of mouth spreads through webinars, trainings, and showing them the value. That's part of a standard go-to-market cycle for new product implementation. Bryan Fields: Has the speed of change in the industry surprised you, or is it what you expected? Ashwin Raj: The industry is impacted by the margin issue — the speed of change is slower than in an industry with capital and margins to invest and move faster. Here we're capital-constrained, and that's slowing things down. All participants need to get smarter about creating efficiency and using that efficiency gain to drive change and improvement. That's an evolutionary step that will naturally happen, and providers like us need to drive that efficiency change to help operators and retailers do different things. Bryan Fields: But to push back — to get those efficiency changes, you have to change behavior, and someone has to be willing to put themselves out there to iterate amid a million other things going on. There's friction between the industry knowing it needs to improve and having the bandwidth to do it. Ashwin Raj: Totally, and this isn't unique to cannabis, it's a challenge in every industry. But for us it's even more imperative, because there are constraints on the wholesale side, the capital side, and the retail side. How do you overcome that? With efficiency gains. On the wholesale side there will be a shift to scale, which brings efficiency and specialization — specialized producers with offerings consumers and retailers want. On the retail side there will be consolidation, because at that level of price compression it's not sustainable. Everybody is going to realize that the current way of operating doesn't work, and we will not continue to be successful and profitable if we continue in this vein — that change is going to happen. You're already seeing larger operators get more vertically integrated, growing their dispensary licenses in different states, trying to create efficiencies to get a larger market share. But that only happens if you have third-party platforms like ours giving medium and small operators the ability to buy products easily without investing in a full sales team, reaching a broader set of retailers. Kellan Finney: What do you think about the hemp industry? I see roughly three tiers: small-to-medium cannabis businesses, larger cannabis players, and the hemp industry, which produces similar products but has none of the same constraints — they can access small business loans and different capital, and it's a safer place to put capital from a federal legality perspective. How do you see these entities working together, or is it going to be one industry taking over from a straight economics perspective, since hemp can operate at true industrial scale without canopy limits? Ashwin Raj: Hemp is going to be a critical factor in the evolution of this entire industry — same technology, same chemical, same processes, but different regulatory treatment. There are positives and negatives. On the positive side, it brings broader, more scalable participation and accelerates consumer adoption and the move to mainstream, given lower THC levels and form factors like cannabis-hemp drinks you can buy at Target or CVS — I think that's required for our industry, similar to how alcohol has different proof levels and you choose which one you want. The regulatory aspect is the most confusing piece for me — why hemp is federally legal while cannabis is illegal makes no sense, but I'm not a policy expert. The way I think about it: we need to enable access to hemp or cannabis products according to each state's requirements. It's similar to my ride-sharing days — San Francisco airport and San Francisco city itself had completely different requirements for drivers, where they could wait, where they could pick up. Some airports push ride-sharing to a remote corner, which makes no sense given how many riders use it and how much they pay in airport taxes, but that's what regulators created. From a product standpoint, it's still the exact same product — whether it's a cannabis drink with THC below or above a certain threshold. On our marketplace, we'll manage this so that, hypothetically, in a state like Minnesota which passed regulation around hemp for licensed operators, a cannabis retailer sees cannabis and hemp products, while a low-potency hemp retailer only sees low-potency hemp products — technology provides that access. So a retailer like Target, as a low-potency retailer, would only be able to buy those types of products. We need to let regulations get smarter and evolve at their own pace, while operators manage for those variations — similar to ride-sharing at airports. Bryan Fields: I was hoping you were going to say JFK in that moment. Ashwin Raj: They can do better, right? We can do better than that — we should aspire to do better. Bryan Fields: The Target example is really interesting — do you see yourself as a shepherd connecting that prior stigma, like what happened with Lyft, helping bridge the gray area for a company like Target, saying 'here's the roadmap, here's why you should trust this platform'? Ashwin Raj: Absolutely, we want to be that trusted platform, one that creates further inroads and moves the illegal part of this business into the legal part. We want both well-established large retailers and the local convenience store to reliably access our platform and know they're compliant when they buy on it. That's where not just industry participants but regulators also gain confidence. Going back to ride-sharing, what turned the tables from illegal to legal was that regulations were being followed because platforms enabled it — that's what made regulators comfortable offering it across a city or state. Today regulators feel a lack of control, and when they feel that, they panic and make up rules that aren't great and hurt everybody in the system. But if we can show there's control and we do the heavy lifting from a platform point of view, they become more confident and the industry evolves. I believe large retailers want to participate — alcohol is in a state of decline and will continue to decline due to health factors. Newer generations are extremely health-conscious and will choose alternative products that don't cause those health effects — cannabis or hemp-based products — and that market is going to grow, and platforms like LeafLink can enable that. Bryan Fields: As a tech product guy, I've got to ask — is AI on the roadmap? Anything you can share that you're experimenting with? Ashwin Raj: We're definitely trying AI, because it's inevitable — you have to incorporate it. Right now we're using it more for internal efficiency — our engineering and product teams are testing it out. I think it'll be a learning curve as various teams use it. I'm actually very bullish about product-based AI. For example, you could develop an AI data-reporting capability where any customer can have the AI build a report suited to their needs — a finance manager may need a different version than an inventory manager. We could also let a retailer say, 'I want this combination of brand, pricing, number of cases available — go look it up,' making search and discovery simple and easy. There are tremendous tools out there we can offer to help both sides of the marketplace. Bryan Fields: I love it. And for customers who want to get in touch or learn more, where can they find you? Ashwin Raj: My email address is very straightforward — it's ashwin.raj@leaflink.com. Whoever wants to reach me, feel free to reach out, or get in touch with anybody at LeafLink and they'll put you in touch with me as well. Bryan Fields: Thanks for taking the time, this was a lot of fun. Ashwin Raj: This was amazing, Bryan, Kellan, thank you so much. Bryan Fields: Take care.