DTC Podcast Ep 547 Summary

Highland’s $10M Playbook: Lean Team, 2 SKUs, and Obsessing Over Unit Economics & CAC Payback
Original Air Date: September 29, 2025
Guests: Ben and Boone, Co-Founders of Highland
Host: Eric Dick (DTC Podcast)

Episode Overview

This episode dives deep into the journey and operational playbook behind Highland, a direct-to-consumer (DTC) hair care brand that broke the eight-figure revenue barrier with only two SKUs and a lean, tight-knit team. Ben and Boone, Highland’s founders, share their origin story, tactical approach to product and brand building, relentless focus on first-order profitability and unit economics, and the scrappy, unconventional strategies that fueled their growth. Listeners get actionable insights for scaling a DTC business in a noisy, competitive landscape.

Main Discussion Points & Insights

Highland’s Origin Story (01:10 - 07:01)

• Personal Mission: Born from dissatisfaction with synthetic “best-in-class” men’s hair products and a desire for healthier, more sustainable options rooted in personal values and family health history (cancer survivor in the family).

  “I grew up in Boulder, Colorado, which … is like a very health and eco conscious place… My dad too was actually a two-time testicular cancer survivor. So health was just a really prominent topic in our household.” – Boone, [01:10]

• DIY Beginnings: Early iterations were literally cooked up on their apartment’s stovetop and shared among friends. The initial mixes “looked like poop in a jar” (03:01) but slowly improved through experimentation and feedback.
• Product Validation: First wins came by proving their “glacial clay pomade” could stand up to the demands of actual barbers/stylists, not just consumers.

  “When he started liking it and wanting to be more part of Highland… we had people like Anthony… raving about it, you know, from day one.” – Ben, [07:01]

Bootstrapping & Early Fundraising (07:01 - 09:09)

• Resisted the VC Bubble: While many peers overextended, Highland pursued profitability from day one.

  “A lot of these direct to consumer brands were raising well beyond probably what they should have been... we got to have an honest look at each other and be like, there's a different way to do this.” – Boone, [07:09]

• Friends & Family: Raised ~$150k in small checks while being disciplined and transparent.

Obsession with Unit Economics & Profitability (08:56 - 10:23; 25:15 - 27:33)

• 80% Gross Margin Target: The team designed their products and pricing model to allow sustainable acquisition and growth.
• Close Collaboration between media buying and finance functions was key—especially with changing acquisition climates and data privacy.

  “Our media buying agency… they weren’t going to take us unless our unit economics were in the place where they needed to be.” – Boone, [25:15]

• Payback Window: Settled on a 3-4 month CAC payback as the “sweet spot” after over-indexing on immediate ROAS and missing scale.

  “We’ve identified like this three to four month payback window being ideal… staying in that window has made, it has really crystallized a lot of our efforts.” – Boone, [26:58]

Scaling on a Lean Team (18:45 - 24:49; 22:02 - 24:49)

• Lean Operations: Reached 8 figures with only four full-time employees (two founders, a creative director, and a packaging/tech generalist, plus customer service handled by Boone’s wife).

  “It’s allowed us to stay really lean… maximize that kind of revenue per employee metric that is becoming more and more talked about.” – Boone, [21:00]

• Agency & Contractor Reliance: Used specialists and advisors for media buying, product formulation, and manufacturing, instead of hiring large teams.

Content Strategy & Brand Building (12:39 - 18:42)

• Founders as Content: Initially fueled by authentic storytelling from Ben and Boone themselves; their own faces and story built credibility with customers.

  “...from day one that performance is so important, but... we tapped is a lot of other people, men and women alike, are experiencing this...” – Boone, [13:35]

• Three-Pillar Content Approach:
  1. Founder-led storytelling
  2. Expert/Influencer validation via barbershop pros and celebrity stylists (notably, partnerships with Hollywood groomers who used Highland on celebrities like Joe Burrow and Bill Nye)
  3. UGC/Aspirational at-home content
• Celebrity & Groomer Strategy: Focused on promoting groomers’ content, not just the celebrity outcomes, to build credibility in the right circles.

  “We’re promoting the groomers content. So it may be a little bit of a gray area to be honest, but… it's been a huge point of validation for us.” – Boone, [16:37]

The Power—and Challenge—of Story-Driven DTC for Non-Traditional Products (12:58 - 14:24)

• Highland proved men will buy haircare online if the story and brand resonate.

  “Telling it about ...how we're fashion forward... how can we get people to kind of buy into the mission… we felt so disconnected to every brand beyond just hair care.” – Ben, [12:58]

• As content fatigue sets in (the “2023 playbook” is tired), they continue to evolve by doubling down on authenticity, investing in grooming industry relationships, and expanding product lines strategically.

Channel Expansion & Reluctance to Join Amazon (00:21; 30:29 - 31:24)

• Initially resisted Amazon but saw a jump in growth after joining (“such an unlock”) thanks to the trust/prime effect and being present wherever customers shop.

  “We were reluctant to join Amazon… But when we did it, it was such an unlock. You need to be in every channel…” – Ben, [00:21]/[30:49]

Sticky Brand, Sticky Customers: Retention & Repeat Strategies (27:33 - 29:47)

• Retention Built on Product: The team strongly believes great retention starts with great product.

  “You can sell anything once. It's kind of our thinking on things but that second purchase is key.” – Boone, [27:59]

• At-Home Experience: Places major emphasis on customer delight from package design, to personalized customer service, and prompt, empathetic responses—no AI bots here.
• Retention fundamentals: Solid flows for email/SMS, tailored landing pages, and experimenting with direct mail.

Scrappy Growth Tactics (31:24 - 35:48)

• DIY PR: Rather than hiring agencies, the founders would buy journalists’ books, send photos, and build relationships directly (“scrappy ways to get noticed”).

  “The one thing… we figured out—the guy who writes a lot of these articles published a book. We went and bought [it], read [it], sent him a picture… nursed that relationship.” – Boone, [32:43]

• Awards as Social Proof: Won GQ and Wired grooming/product awards through organic outreach, not pay-to-win.
• Creators & Affiliates: Focus on relationship-first influencer marketing. Long-term partnerships with creators who genuinely use and love the products.

Product Expansion Lessons (18:45 - 20:38)

• Despite eight-figure results on just two (now three) SKUs, founders wish they had ramped product development earlier to drive AOV & LTV. Product #3 (“awash”) is now padding retention.

Team Structure & Culture (22:02 - 24:49; 22:08 - 23:03)

• Strong co-founder dynamic: Ben (marketing/content), Boone (ops/finance/dev), emphasis on mutual respect, clear division, and vulnerability as friends-turned co-founders.
• In-house creative: The creative director (Brendan) is pivotal for content; plans to hire more creatives to reinforce brand moats.
• Emphasis on personal, trust-based relationships (not just with customers but agencies and contractors).

Notable Quotes

• “We are not trying to just chase the dollar like we did this to solve the problem ourselves. We want to tell that story.” – Ben, [00:00]
• “We got to eight figures just on the backs of two SKUs… Let's stay first order profitable. That's the best thing we can do.” – Boone, [00:06]
• “Back to the natural formulations thing. When you're using natural, plant derived ingredients, they tend to be more expensive… For us it was about trying to get to around 80% gross margin.” – Boone, [09:09]
• “You can sell anything once. …That second purchase is key.” – Boone, [27:59]
• “We’re promoting the groomers content. …It’s been a huge point of validation for us.” – Boone, [16:37]
• “Everything for us is relationships.” – Boone, [35:44]
• “You need to be at every, in every channel, on every platform where your customers are…” – Ben, [30:49]
• “It's allowed us to stay really lean… maximize that kind of revenue per employee metric.” – Boone, [21:00]

Key Timestamps

• Origin Story: 01:10 – 07:01
• Fundraising Approach: 07:01 – 09:09
• Unit Economics & Profitability Focus: 08:56 – 10:23; 25:15 – 27:33
• Scaling on Meta; Storytelling Content: 10:23 – 14:38
• Content Evolution/Pillars: 14:38 – 18:42
• Scale, SKUs & Product Expansion: 18:45 – 20:38
• Team Structure & Culture: 22:02 – 24:49
• Finance/Media Buying Integration & CAC Payback: 24:49 – 27:33
• Retention & Experience: 27:33 – 29:47
• Amazon/Channel Reluctance & Unlock: 30:29 – 31:24
• Scrappy Tactics & PR: 31:35 – 35:48
• Vision, Goals, and Future Hires: 36:10 – 38:54

Memorable Moments

• Winning “Best Hair Clay” with Stovetop-Formulated Product: From handmade batches to an international award (32:43 – 33:03)
• Celebrity Groomers & Red Carpet (Joe Burrow, Bill Nye): Growing brand awareness through insider industry relationships, not direct celebrity endorsements (16:21 – 16:37)
• Founder Vulnerability & Friendship: Honest conversation about co-founder dynamics and the challenge of growing a business with a best friend (22:08 – 23:03)
• Radical Customer Service: Eschewing AI in favor of highly personal email support (24:49)

Practical Takeaways for DTC Founders

• Build your brand around real, relatable stories—especially where your product category isn’t “obviously” bought online.
• Focus on unit economics and CAC payback from day one. Solvent, sustainable growth trumps chasing revenue at all costs.
• Don’t underestimate scrappy, DIY PR and relationship-building.
• Stay lean. Outsource non-core functions and focus on best-in-class team performance.
• Treat creators, pros, and customers as long-term brand partners—not just transactional levers.
• Amazon presence is critical—even if you care deeply about your brand experience.

Connect with Highland

• Web: highland.styles
• Social: Instagram, TikTok, Facebook – @highlandstylecompany

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