Cannabis leaders have spent years adapting to capital constraints, price compression, and shifting regulations. Making it through those changes takes persistence. Building a business that can thrive through the next set of changes takes something more: knowing when to reconsider a strategy, where to commit resources, and how to turn early warning signs into action.
On the Emerald Insights Podcast, AnnaRae Grabstein joins Ed Keating to explore those decisions from both sides of the table. The founder and CEO of Wolf Meyer and co-host of High Spirits has built and operated cannabis businesses and now advises leaders across the industry. Her perspective comes from managing the consequences of strategic decisions, including the difficult ones. Throughout the conversation, she returns to a practical challenge: how do leaders recognize what their business needs today when so much of their thinking is shaped by what worked before?
A process can work exactly as intended and still reach the end of its usefulness. Grabstein sees this across the companies she advises, from warehouse fulfillment and sales processes to channel partnerships. Leaders invest time and effort in building an approach, see it deliver results, and understandably become attached to it. But as volume, headcount, and complexity increase, the business can outgrow the systems that helped it succeed.
“That doesn’t mean that the before was any less important, valuable, or impactful. It’s just how do we chart a path forward.”
That distinction gives leaders room to make changes without treating earlier decisions as mistakes. The question becomes whether the approach still fits the company’s scale, resources, and market. Grabstein notes that when something doubles or triples, the processes surrounding it often begin to break. Waiting for the old approach to work again can delay the investment or redesign the business now needs.
Cannabis market intelligence adds another dimension to that assessment. Internal performance shows how an operation is functioning, while changes in competitors, ownership, licenses, and market coverage help explain the environment around it. A company’s sales strategy may need to change because its own business has grown, because the market has shifted, or because both have happened at once. Leaders need visibility into those changes to decide what to preserve and what to rebuild.
Grabstein points to shrinking margins, employee retention, on-time deliveries, compliance, and product quality as indicators that deserve attention. The specific measures will vary by company, but the discipline is the same: understand the baseline, know the target, and investigate when performance starts to slide. Recurring problems are particularly revealing. They can show where an organization is struggling to respond, even before the consequences become obvious in its financial results.
“When things are a problem in a business and people don’t take it seriously and it just sticks and stays and creates toxicity or it creates habit, those are things that are really hard to break.”
Her concern extends beyond whether leaders can identify a problem. It includes whether the organization can do something about it. In larger companies, employees closest to the work may already understand what is going wrong but lack the authority to make changes. They may also feel that nobody is listening. A business can have useful information on the ground and still fail to bring it into its decisions.
That makes responsiveness an operating capability worth examining. A dashboard may flag missed deliveries or declining retention, but the value comes from assigning ownership, understanding the cause, and following through. When the same issue keeps returning, leaders need to examine both the underlying problem and the process for resolving it. Otherwise, the company risks accepting a lower standard simply because it has become familiar.
Recognizing a problem does not always mean the right answer is to fix it. Grabstein describes a large multi-state operator that hired her to assess its struggling California wholesale business. She identified what a turnaround would require: more field marketing, more salespeople, and a different distribution strategy. There was a credible path to improving performance. The harder question was whether pursuing it made sense within the company’s broader portfolio.
“I could see that really that work wasn’t worth it because they had a whole bunch of other opportunities that were more valuable and resources are not unlimited. And so we need to be able to make choices.”
Her recommendation was to exit that part of the business and focus elsewhere. The example illustrates why evaluating an operation in isolation can produce an incomplete answer. A business unit may be capable of growth while competing for resources with opportunities that offer substantially more value. The cost of a turnaround includes the management attention, people, and capital that become unavailable for other priorities.
For executives and boards, that puts resource allocation at the center of the growth discussion. The ability to improve a business does not settle whether the company should invest in doing so. Leaders need to compare the opportunity with the alternatives available to them. Walking away can be a deliberate decision to strengthen the broader business.
The episode’s discussion of Curaleaf’s proposed Aurora transaction explores the gap between a company’s trading price and the strategic value a buyer might see in its assets. Grabstein considers the companies’ different approaches to financing and growth, along with the complexity of a cash-and-stock offer. She also emphasizes the distance between an announced proposal and a completed transaction. The public discussion captures only part of the work required to bring two businesses together.
“We hear about the deals that do happen more often than we hear about all the deals that don’t happen.”
That observation is useful context for leaders assessing acquisition opportunities. An announcement can signal ambition and strategic direction, but completing a deal requires agreement on value, financing, and the conditions under which the combined business will operate. A larger footprint also raises questions about overlapping assets and the resources needed to execute the plan. The strategic case needs to hold up beyond the appeal of scale.
Cannabis license data and ownership relationships help make those questions more concrete. Understanding which facilities, licenses, and markets sit behind a transaction gives teams a clearer view of what a combination could accomplish. Ed describes how mapping companies’ footprints can reveal where businesses complement each other and where they overlap. That is the kind of market context that helps turn an acquisition idea into a more informed assessment.
Grabstein’s discussion of potential interstate commerce raises questions about cultivation investment, supply chains, and vertical integration. She considers how emerging markets might develop under a different supply structure and whether the advantages operators rely on today would remain as valuable. Those possibilities are still uncertain, with legal and administrative steps unresolved. They deserve consideration without becoming the foundation of a business plan.
Her practical advice is to keep the business healthy under current conditions while examining how future changes could affect major decisions. Leaders can assess which investments depend heavily on the existing market structure and which capabilities would remain useful across different scenarios. That creates a more disciplined planning exercise than assuming a particular policy outcome or timetable. The goal is to understand exposure and preserve the ability to adapt.
When asked what will distinguish the companies that do well, Grabstein returns to people and customers. Teams need clarity about where the business is heading and the agency to contribute at every level. Companies also need to attract and retain talent while listening closely to the people they serve. Her view is that advantages created by regulation will not be enough to sustain success indefinitely.
“Endlessly focusing on your customer and the consumer is the thing that is going to create winners, not just regulatory capture.”
That focus brings the conversation back to the decisions leaders can make today. They can address recurring problems, reconsider outdated processes, direct resources toward stronger opportunities, and equip employees to act. Market intelligence helps them understand the conditions surrounding those choices. The lasting value comes from using that context to build a company that responds well—to its market, its team, and its customers.
Watch or listen to the full Emerald Insights episode with AnnaRae Grabstein for the complete conversation.