Marketing Operators – Operators Titans E002: Portland Leather Goods (with CMO MacCoy Merkley)

Date: October 2, 2025
Guests: MacCoy Merkley (CMO, Portland Leather Goods)
Hosts: Connor Rolain, Connor MacDonald, Cody Plofker

Episode Overview

This episode of the Operators Titans series dives into the grassroots journey of MacCoy Merkley, who went from a wedding photographer with no formal marketing experience to CMO of Portland Leather Goods. The discussion covers MacCoy’s unconventional entry into digital marketing, navigating the growth of a fledgling Etsy shop into a nine-figure DTC brand, and his perspectives on scaling teams, channel expansion, and the mindset frameworks, tactics, and philosophies that have driven his and the company's success.

1. MacCoy’s Unconventional Beginnings & Wild Interview Story

• MacCoy shares his struggles with feeling unfulfilled and believing he “was not smart enough,” leading him to seek purpose and structure.
• He answered a Craigslist ad for a "digital media specialist" at Portland Leather Goods despite lacking a resume or formal marketing background.
• The interview with founder Curtis was unorthodox and energetic:
  • MacCoy recalled, “I started making fun of him back. Cause I was like, screw you, man. Like, I'm not gonna sit here and take this.” (04:24)
  • Initially sent away, Curtis called him back 30 minutes later for a job offer.
  • MacCoy started the next day at $13/hr, with no clear job scope.
• He described his early days as “basically trying not to get fired” (06:33), attaching himself to the neglected Shopify site and refusing involvement with the Etsy side.

2. Early Days: Scrappiness, Self-Teaching, and Grassroots Growth

• MacCoy relied on self-taught skills, learning media buying and eCommerce via “the University of YouTube,” and trial and error.
• Recognized some foundational marketing intuition from pitching wedding photography services, particularly “targeting engaged women in Portland”—analogous to early, highly targeted media buying.
• Revenue growth: <$1M to over $15M in a few years.
  • “We ended up hitting around one, just over one that year. Five the next year, 15 the next year. So, like, exponential growth in my first few years.” (08:26)
• Reluctant to adopt the existing Etsy focus, insisted on owning the Shopify direction.

Key Quote:

“I wouldn't hire me if I was, if I came in. I was like I'm a wedding photographer. Let me run your, you know, your nine figure company. Like no thanks. But I knew how to like put my own content online.”
(08:01, MacCoy Merkley)

3. Influences, Learning Resources, and the Evolution of the DTC Marketing Operator

• Early learning relied on available content creators:
  • Credit to founder Curtis for product-market fit and “delivering insane value.”
  • Relentless YouTube learning: Neil Patel, Gary Vee—though most resources felt vague and non-actionable.
  • Heavy value drawn from peer communities (“cloud of Operators”) as the company and DTC ecosystem matured.

Notable Reflection:

“From being able to like to run ads for a great product at an insane price is just, you can't beat that. And I'm like, so sorry for people who are stuck in brands and in businesses with like a terrible product they have to put some sort of spin on.”
(10:10, MacCoy Merkley)

4. Operator Roundtable: Self-Taught Marketers’ Journeys

• Hosts share their own self-education stories—from Facebook groups (BAMF, David Herman, Taylor Holiday, etc.), agency experience, and investments in direct response courses.
• Shared sentiment: community and paid learning (courses, masterminds, etc.) remain vital for operators at all stages.

5. Transition from Generalist IC to Manager and Executive

Key Discussion Points:

• The rare path of growing from doer to manager to executive within a single scaling organization.
  • “It's really hard to get good at a specific thing and then getting good at executive level management is difficult by itself. And so when you have two things that are rare, it's not just how rare each individual thing, they multiply against each other.” (20:02, MacCoy Merkley)
• The challenge of letting go—delegating, trusting team layers, and evolving from hands-on work to executive direction.
• Continual personal growth is necessary: “...given a long enough period of time I won't be the CMO... but I'm trying to make sure when that happens it's because I like die of old age, not because like the business grows to a point where I can't support it.” (22:13)

6. The Philosophy of “Accelerated Common Sense”

• MacCoy’s core management framework: most business problems are knowable; attack problems swiftly with “velocity”—whether solving them directly or sourcing domain experts.
  • “Accelerated common sense... it is knowable. I just need to figure out how to know it... that's the framework.” (26:05)
• On overcoming imposter syndrome: “I wasted way too many years believing I was not smart enough... only to figure out that it's basically just accelerating common sense all the way up.” (23:51)

7. Decision-Making under Uncertainty

• Effective operators don’t wait for perfect information—hunt for it, move forward, forgive mistakes, and create risk-tolerant environments for their teams.
• Insist on action: “You have to go like hunt and kill [information], but at some point, like, you have to move. It's not an option to stand still and so forgive yourself.” (31:22)

8. Channel Expansion, Marketing Mix, and Vetting New Opportunities

Early-Stage Approach & Channel Mix Evolution

• Start focused: “When you're very small, I recommend that you focus on like as few number of things as possible... pick something... do it really, really well.” (33:44)
• For Portland Leather Goods:
  • Early mix: Meta (Facebook/Instagram), accidental reliance on Pinterest, later balanced with Google when a specialist joined.
  • Through nine figures: “I spent every dollar on meta, myself and one other person, up until we hit nine figures in revenue.” (35:18)
• Recent years: More diversified; Pinterest still small, AppLovin now ~10-12%, Google 20–30%, heavy on Meta.

Vetting New Channels

• “The first part is to say no, like, over and over and over and over and over again.” (37:41)
• Lean on operator peer groups to validate new opportunities before investment.
• Ratio of “no’s” to “yes’s” is extremely high to keep focus and avoid shiny object syndrome.
• If opportunity isn’t sought as part of a deliberate strategy (versus cold outreach/pitch), it’s a default no.

9. Media Mix Analytics, Frequency, and The New Growth Challenge

• Measuring paid media impact: In a recent year, they reached 60 million US women 20 times each on Meta.
  • Hard question: “Is it that I think I'm going to spend way, way, way more money and I'm going to get it to 70 million, or am I going to spend way, way more money and my frequency goes to like 30 or 40? Like, what's the correct number?” (44:53)
• Strategic focus shift: Increasing value per impression through brand, influencer, and multi-channel storytelling, rather than just scaling ad frequency.
• Both hosts and MacCoy agree on a need for unique reach and creative diversity, moving beyond “just spend more on Meta,” especially as reach per dollar plateaus.
• Emphasis on cross-brand learning: “...I think by 2028 and 2029, none of us will shut up about retention, right?” (52:31)

10. Titan 10 (Rapid Fire Round)

1. Desert Island Dashboard – Top 3 Metrics:

• CAC (Customer Acquisition Cost)
• 12-month LTV (Lifetime Value)
• Contribution Margin per Customer (55:11)

2. Non-Business Book/Resource:

• “It's gotta be some sort of caffeine... like a Celsius energy drink.” (55:30)

3. Contrarian Belief:

• “80% of your performance is completely outside the ad account. It's brand and, and your company and your position, your product.” (55:53)

4. Most Important Leadership Word:

• “Courage. It's like telling people the truth. It's confronting stuff you don't know. It's being uncomfortable, it's growing.” (56:13)

5. Best Meal:

• “Breakfast... the meal you can tweak the most, like in time.” (56:42)

6. Most Overrated Growth Tactic:

• “Creative volume. I think most people don't need it. I think they're just listening to conversations from people way, way, way, way larger than them.” (57:04)

7. Most Underrated Tactic:

• “CRO [Conversion Rate Optimization]... one good decision can lift every channel, every campaign, every ad set, every piece of creative.” (57:41)

8. Most Important Word in Business:

• “Growth. Like we business exist in an economy. Like they serve a purpose, like they're, they're here to generate money and growth is absolutely imperative to that.” (58:24)

9. Is Constant Revenue/Profit “Growth”?

• “Depends on the time... if you had to build a business whose sole objective was to survive 100 years, could you describe that business? ...Is it gonna be healthy in 10, 15, 20 years? I don't think so.” (59:42)

Notable Quotes & Memorable Moments

• “I wasted way too many years believing I was not smart enough.” (00:00, 23:51, 26:05, 26:18, 26:30; motif throughout)
• “The whole world was built by people no smarter than you.” (00:17, 23:51)
• “Accelerated common sense all the way up.” (25:52, 26:05)
• “If you have a very short amount of time to succeed... the less you know the harder and the faster you should commit to, like, throwing yourself in and being at the mercy of the people who do know…” (29:27)
• “You do not get to stand still. The business itself has to grow — its natural state is dying. There's no standing still on the treadmill.” (00:17, 58:24, 58:57)

Timestamps for Key Segments

• 00:00 – Opening theme; the struggle with self-doubt
• 02:05 – MacCoy’s wild entry and interview at Portland Leather Goods
• 06:33 – Early days, finding a way to contribute and not get fired
• 09:58 – Influences and resources for self-taught marketers
• 20:02 – Transition from IC to manager to executive: the “two rare things” challenge
• 23:51 – Frameworks for management and accelerated common sense
• 33:44 – Channel focus, media mix, and growth stages
• 37:41 – Channel vetting process and philosophy of “default no”
• 44:18 – Media mix analytics and frequency as a new constraint
• 55:11 – Rapid-fire “Titan 10” operator questions

Tone & Takeaways

The episode is candid, punchy, irreverent, and full of lived experience from the DTC marketing trenches. MacCoy’s journey illustrates self-taught grit, strategic focus, and humility in leadership, while offering tactical and philosophical frameworks for operators scaling from grassroots to nine figures and beyond. The conversation is a reality check for early-stage founders on prioritization, and an invitation for advanced operators to rethink incremental gains in frequency, reach, and brand value as the real engines of sustained growth.

For Operators:

• Start focused, say no often, and use your peer network to validate new opportunities.
• Attack problems quickly; you don’t need to know all the answers, but you must accelerate towards know-how.
• Internal growth and brand value dwarf the impact of incremental ad account optimizations.
• Constantly question whether your “growth” is sustainable for the next 100 years.