Podcast Summary: Earn Your Leisure

Episode: How Two Friends Built a $750 Million Barber Tech Company

Original Air Date: December 19, 2025
Hosts: Rashad Bilal & Troy Millings
Guests: Song and Dave (Co-Founders, Squire)

Overview:

This episode of Earn Your Leisure spotlights Squire, the trailblazing barber shop management platform founded by friends Song and Dave. Hosts Rashad Bilal and Troy Millings dive deep into how the duo transformed a dated, manual industry into a streamlined, tech-powered business with a $750 million valuation. With honesty and candor, Dave and Song discuss the origin story of Squire, the technical and cultural challenges they overcame, and how building with both their community and a global mindset propelled them into industry leaders. The episode gives crucial insight for aspiring founders, especially those from underrepresented backgrounds, on scaling a tech business, fundraising, and navigating exit strategies.

Key Discussion Points & Insights

1. Origin & Inspiration of Squire

• Squire started with Song and Dave’s personal frustrations as long-time barbershop clients. Despite career success in law and finance, they felt unfulfilled and brainstormed ideas to make a bigger impact.

• They identified how the barbershop experience hadn’t changed in decades: inconsistent wait times, cash-only payments, and little operational structure. Their vision was to modernize this community staple with technology.

  "Both of us have been going to barbers since we were kids. I started going around six or seven... The experience hadn't changed 20 years later. You go in, you wait. It could be 10 minutes, it could be two hours."
  – Song, 04:23

2. Product Evolution and Value Proposition

• Squire evolved from a simple booking app to a full barbershop management suite—handling appointments, payments (including tips and cashless experience), and business operations.

• Enabled significant efficiency improvements for barbers, who could now maximize their schedules and get more clients.

  "We take that kind of [Uber] experience, like, to the barbershop as well."
  – Dave, 02:20

  "With technology now you can't do that because everything is regimented, everything is on point."
  – Song, 05:49

3. Building & Launching the Business

• Song and Dave weren’t from tech backgrounds, highlighting the steep learning curve in development.

• Their early strategy: recruit a technical co-founder instead of outsourcing, emphasizing the importance of aligned incentives.

• Launched the first MVP after multiple iterations and close collaboration with target users.

  "We used to sneak into Columbia campus... literally just whiteboard ideas."
  – Song, 04:23

4. Getting to Market: User Buy-In & Marketing

• Focused first on barbershops rather than end users.

• Early growth required face-to-face sales: visiting countless NYC shops and onboarding owners, often using the product themselves to showcase value.

• Initially gave the software away free and made revenue via transaction fees.

  "It was really like hand-to-hand combat."
  – Dave, 14:09

  "You gotta give it away free to get product market fit."
  – Dave, 15:11

5. Business Model & Monetization

• Revenue comes from two main streams:
  • Barbershop subscriptions ($30 to $250 per month depending on scale, 15:27)
  • Transaction fees on payments through the app
• Didn’t charge for software for the first three years; instead relied on angel investments.

6. Fundraising Journey & Challenges

• Early rounds funded through personal networks and repeated, small angel investments.

• Y Combinator (2016) was a pivotal moment, providing critical credibility and access to institutional investors.

• The Series A ($8M) was a protracted challenge (“about 60 meetings and got like one term sheet”, 20:02), reflecting the unique hurdles faced by Black founders.

  "The best businesses are bought, not sold."
  – Song, 43:44

7. Scaling & Operations

• Scaling from founder-led outreach to a large, experienced executive team was crucial for growth.

• Current: 32,000 barbershops, 10 million clients (32:04), with over 200 employees (58:32).

  "The more we learn about our business and... the more mature we get, like, we see, like, okay, this is fundamentally, this is just a really solid, strong business that's going to endure."
  – Song, 27:59

8. Fundraising in Boom Times

• Described the momentum after COVID: Squire was first to waive subscription fees and rapidly developed tools for survival (virtual waiting rooms, Covid forms).
• Raised over $100M in a year over multiple rounds as a result (49:41 - 50:03).
• Emphasized judicious use of capital—most of the money was saved as a buffer, not rapidly deployed.

9. Competition, Differentiation & AI

• Squire remains laser-focused on barbershops, while competitors aim for a broader, less tailored approach.

• AI is now a central differentiator:

  • Operator (AI answering service to handle calls and bookings, 07:06)
  • Engage (AI-powered marketing for shops to reach clients, 72:02)
  • Engineering output reportedly up 94% because of AI integration (58:21)

  "We're so laser focused on building the best products specifically for this user base. And that allows us to go deeper."
  – Dave, 48:06

10. Ownership, Equity, and Exit

• Most employees receive equity—both for incentives and wealth creation (39:35).
• Founders' equity diluted over time; control protected via board structure rather than majority ownership (40:14).
• Exit strategies: Not currently for sale, but with venture capital investors, a liquidity event (M&A or IPO) is the expected outcome.

11. Diversity, Expansion, and Social Impact

• Squire’s staff is among the most diverse at their scale.
• Early pitch decks avoided over-associating the product with Black barbershops to avoid limiting perceptions; actual market is broad and matches barbershop population at large (30:08).
• Launched “Squire for Schools”—a barber school partnership program offering free software to teach best practices early (64:24).

Notable Quotes & Memorable Moments

• On Starting Up:
  "You have to understand... if you don't like pitch 100x type of opportunity, then it just doesn't excite [investors] as much."
  — Song, 26:09

• On Board Relations:
  "Now you're literally accountable, responsible. Every quarter, you have to report how you're doing..."
  — Song, 24:00

• On Market Misconceptions:
  "Because we're two black founders, [they thought] we're just focusing on black barbershops... we made it really clear we were not... We were going after the entire market."
  — Song, 28:33

• On the Changing Fundraising Landscape:
  "The folks that... passed on the series A came back and led the B six months later. And then nine months later we raised the C... we weren’t pitching. People were just coming to us."
  — Song, 50:09

• On Price Increases for Haircuts:
  "It's capitalism. It's the market... if you're charging those high dollar amounts, they just value their time."
  — Dave, 62:17

• On Qualities Needed for Success:
  "The number one trait is resilience... It's a war of attrition that won't give up."
  — Song, 69:48

Timestamps for Key Segments

• Origin Story & Barbershop Pain Points: 04:23–06:14
• Product & MVP Development: 09:17–10:38
• Go-To-Market & User Acquisition: 12:22–14:40
• Business Model & Monetization: 15:11–16:45
• Fundraising Struggles & Y Combinator: 16:50–21:13
• Series A Lessons: 24:34–26:54
• Scaling Team & Operations: 36:40–37:40
• Ownership & Employee Equity: 39:35–41:02
• Exit Strategy & Investor Expectations: 43:06–44:41, 68:36
• Marketing, AI and Product Differentiation: 45:05–49:25, 72:02
• COVID Impact & Rapid Growth: 49:41–52:04
• AI & Efficiency: 57:42–59:07
• Global Expansion: 55:02–56:29
• Advice for Aspiring Founders: 69:25–70:53

For more about Squire and AI innovations:
🌐 getsquire.ai

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Tone: Warm, direct, collegial—filled with lived experience and real talk about business realities and the tech journey as Black entrepreneurs.