Make It Make Sense: Why the Diagnostic Comes First

How to Tell a Marketing Problem from an Operations Problem Wearing a Marketing Costume

Marketing Problem, or Operations Problem?

When the topline is not growing, the CEO most often looks first to the CMO. That’s understandable because marketing is charged with value creation:

1. Understanding what the customer wants

2. Creating products and services that meet those needs

3. Communicating to the market in such a way that the customer then buys.

But often, companies that were growing stall not because of a simple marketing problem, but because of many problems, which can include an operations problem hiding in a marketing costume. And taking too long to diagnose that will cause you to waste time pulling levers that don’t get you the step change in performance that you’re looking for. 

The pressure to drive growth doesn’t stop at the executive team. It runs upward to the investors, who are looking to exit, and is especially high in private equity, where firms buy companies with a plan to sell them within a set number of years. While holding periods are increasing across the board, operating partners in private equity in particular are feeling the pressure. According to Bain & Company’s Global Private Equity Report 2026, average exit holding periods have stretched to roughly seven years, up from five to six between 2010–2021, against a backlog of an estimated 32,000 unsold companies industry-wide, worth $3.8 trillion. (1) There isn’t time to waste pulling the wrong levers. There isn’t time for misdiagnosis. Yet running straight to marketing and pressuring for innovation and tactics without first doing the diagnostic work leads to expensive mistakes that nobody wants.

The Halo Car Bet

In 2020 I worked at a cannabis company that went public through a roll-up SPAC merger, where a blank-check company buys several operators at once and combines them in a single transaction. It is one of the most operationally violent processes a marketer can go through -- two or more complete organizations are forced into a single P&L before any of the systems, cultures, or mandates have been reconciled. What became known as The Parent Company (TPCO) was at the time hailed as the largest vertically integrated cannabis company in California, the largest cannabis market in the United States. The pressure on marketing began immediately -- with published projections to grow revenue from $110M in 2019 to $593M in 2022, +439% growth in three years. Branded wholesale, the portfolio of products that I managed as Senior Director of Marketing, was projected to deliver more than a quarter of 2022 revenue. (2)

The playbook the company chose to run was clear and well-worn. It’s the bet every flagship-led campaign makes and one that was quite common in cannabis during this “gold rush.” Leverage the visibility of the company’s best asset, its partnership with Jay-Z and Roc Nation. It's the same bet automakers make with what they call a “halo car” -- a flagship model designed to generate buzz that's supposed to lift the rest of the lineup. 

It made sense to focus resources here. Millions were spent. Lots of marketing was done. There were billboards, press releases, over a billion impressions. And results were realized. Awards were won, and there was plenty of buzz -- all focused on the flagship brand from the partnership, Monogram. (2, 3, 4, 5, 6, 7) The problem was that those results weren’t the kind you could take to the bank. The company projected $334M in revenue for 2021. Actual net sales were $173M -- about half. (2, 8)

Why wasn’t the marketing working?

Turns out the wrong question was being asked because the problem was never correctly diagnosed. The problem was never a lack of awareness. It was the gap that opened up after it. If you bought cannabis in California between 2020 and 2022, you likely knew about Monogram. But did you know where to buy it? Despite the advertising, The Parent Company operated only five owned physical stores statewide as of mid-2021. (9) This means the bulk of the opportunity to find Monogram (and other brands owned by The Parent Company) across the expansive state of California remained in wholesale accounts owned and operated by other companies. And while that is common in most categories, let’s look more closely at why that was an obstacle. 

Imagine if roughly 96% of the retail stores available for you to buy alcohol disappeared overnight. The liquor store. The corner store. The gas station. The grocery store. Target. None of them sold alcohol anymore. Just a tiny fraction of stores that you’re not familiar with. Well, that’s the cannabis market. In California in FY 2021-2022 there were 28,305 retail permits for off-premise alcohol sales statewide, but only 1,002 for cannabis. (10, 11) So the mass media playbook that was being run was developed for a market where the product was easy to find. But in cannabis, it isn’t.*

What Happened Next?

The Parent Company later took a step toward closing that gap. In 2022 the company shifted from distributing its own products to an exclusive wholesale partnership with Nabis. (13) The shift was meant to cut costs and standardize how products reached retailers, with streamlined ordering and two-day shipping. But getting product onto shelves was only part of the problem. In cannabis, retail staff play a strong advisory role with customers and heavily influence the purchase decision. Winning at the shelf takes a full retail playbook: standard promotions, store displays, demo programs, budtender education. A distribution partner could standardize the wholesale side of that and protect some of marketing's hard-won head start. In a market this fragmented, with roughly 1,000 stores statewide and nearly all of them owned and staffed by someone else, the person-to-person budtender education Monogram depended on was never going to scale. [For more details on how I diagnosed the problem and developed what would later become The Diagnostic, see my portfolio.]

However, these improvements weren’t enough to fight the intense headwinds in the industry. In 2023, the company merged with Gold Flora, citing operational efficiency, supply chain optimization and gross margin improvement. (13) In 2025, the combined company entered receivership after defaulting on loans and dealing with legacy lawsuits that it inherited from The Parent Company, with key assets sold to Stiiizy for $25M. (14)

Visibility is an important piece of the puzzle. But in a market as complicated as cannabis, visibility means nothing if your operations can’t keep up. And if you don’t take the time and money to diagnose the right problem, you’ll waste both solving the wrong one. But your effort doesn’t have to be focused on just cleanup work. What if some of this diagnostic work had been done more as a strategic investigation before Monogram was launched? Before investing in an expensive, mass-media-focused, high-visibility strategy? Before pouring millions into a plan that, in retrospect, had little chance of success?

What is The Diagnostic?

The Diagnostic is a standalone engagement. It produces a clear picture and a prioritized set of decisions. Every engagement starts here. Before strategy, before execution -- the business needs to be understood as it actually works, not only how it presents. The real architecture. What's working, what's stuck, what nobody has named yet.

I do that by getting into the messy middle of things, not by just looking at spreadsheets on my laptop. The key premise of The Diagnostic is that nothing is taken for granted. I start from the beginning to understand the consumer mindset. This involves reviewing research you may have on hand, publicly available consumer reviews, but also secret-shopping and chit-chatting with customers in the store and in the parking lot. Noticing how many rings before someone answers the phone. How quickly an older customer is greeted. How long it takes for store staff to reply to my email. Bringing fresh eyes often surfaces the obvious -- did you know your address was listed incorrectly in several places on your website?

The hands-on review is supplemented by a comprehensive overview of all your marketing channels -- recent and historical results. Where are you winning? Which channels are bringing in new customers? How are you engaging with previous buyers? How does purchase behavior change over time? Who’s winning in your category? What’s unique about your store, staff, inventory capabilities or messaging versus your local or online competitors? Where are you deficient that we need to guard against? Where are you strong that we can lean into? What’s missing in your story that would resonate and what tools or capabilities do you need to get that message out there? Which of your tactics are trackable? Depending on your capabilities, we can augment a lack of specificity from suboptimal tools with category learnings, analogous case studies in other areas, or gut checks from my 20 years in the room. And from all this information we’ll be able to put together an incredibly detailed picture of what’s likely driving -- or blocking -- your business’s growth. [To see The Diagnostic in action, review the DME Retailer example in my portfolio.]

And that’s why The Diagnostic has to come first. If you have companies in your portfolio that have been held longer than planned, you need a clear picture of the problem. Then you can move in the right way with full force, instead of finding out a few years and a few million dollars later that you were moving in the wrong direction. You have to take the time to make sure that you’re seeing things correctly. 

None of this is a claim that a diagnostic hedges against every headwind a business will face. Markets turn, regulations shift, capital dries up. All of that can still happen. What it does is narrower and more useful: it catches the layer of misdiagnosis that's actually inside your control, before you spend real money finding out about it the hard way.

What’s the saying? Proper preparation prevents poor performance. I prefer proper diagnosis prevents expensive mistakes. But hey, if that ship has already sailed, The Diagnostic can also help you figure out where to focus your cleanup crew.

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*: This comparison focuses on brick-and-mortar retail only. Delivery is a legal and growing channel in California cannabis, but it's proven fragile as a business model at scale. Eaze, the state's largest cannabis delivery company, burned through roughly $350 million before its original entity collapsed into Chapter 7 bankruptcy in 2025. Its assets were absorbed by a creditor and relaunched as a smaller company with explicitly slower growth ambitions. (14)

Sources: 

1. Bain & Company, 2026, https://www.bain.com/insights/welcome-to-a-new-era-global-private-equity-report-2026/

2. Subversive Capital Acquisition Corp., Investor Presentation, December 14, 2020

3. Cannabis Business Times, 2021, https://www.cannabisbusinesstimes.com/us-states/california/news/15690105/shawn-jay-z-carters-monogram-challenges-national-drug-policy

4. Variety, 2021, https://variety.com/2021/music/news/jay-z-monogram-weed-cannabis-slim-aarons-1234950224/

5. Shorty Awards, 2021, https://shortyawards.com/14th/monogram-good-life-redefined-campaign

6. Clio Cannabis Awards, 2022, https://www.cliocannabisawards.com/winners/monogram-monogram-x-the-good-life-redefined-49-85.html

7. Clio Cannabis Awards, 2021, https://www.cliocannabisawards.com/winners/monogram-the-hypocrisy-34-74.html

8. New Cannabis Ventures, 2022, https://www.newcannabisventures.com/tpco-holding-reports-q4-revenue-flat-sequentially-at-39-6-million/

9. New Cannabis Ventures, 2021, https://www.newcannabisventures.com/the-parent-company-opens-5th-california-cannabis-store/

10. California Department of Alcoholic Beverage Control, 2022, https://www.abc.ca.gov/licensing/licensing-reports/annual-report-archives/license-summary-counts-for-fy-2021-22/state-totals/

11. Getting It Right From The Start, 2022, https://gettingitrightfromthestart.org/wp-content/uploads/2022/03/Setting-the-Record-Straight_FS_3.17.22.pdf

12. Cannabis Business Times, 2022, https://www.cannabisbusinesstimes.com/us-states/california/news/15692734/the-parent-company-nabis-agree-to-distribution-partnership

13. Gold Flora Corporation, 2023, https://www.newswire.ca/news-releases/gold-flora-and-the-parent-company-complete-transformational-merger-822140582.html

14. MJBizDaily, 2025, https://mjbizdaily.com/news/stiiizy-picks-up-pieces-of-failed-conglomerate-for-25-million/613180/

15. The San Francisco Standard, 2025, ​​https://sfstandard.com/2025/04/20/eaze-weed-uber-delivery-silicon-valley-cannabis/