Podcast Summary: Making It with Jon Davids – Episode 209

Guest: Drew Green, CEO of Indochino

Release Date: September 5, 2025

Episode Overview

In this engaging "Quick Cut" episode, host Jon Davids sits down with entrepreneur and CEO Drew Green (Indochino) to unpack the art of raising massive amounts of capital. Drew shares his approach to scaling a regional brand into a $100M company by strategically partnering with investors, navigating international deals, and maintaining fulfillment through balancing work and life experiences. The conversation is rich with practical advice, personal stories, and insider insights on what it really takes to fund and scale big ideas.

Key Discussion Points and Insights

1. The “Triangle of Value” Approach to Raising Capital

[00:38]

• Drew emphasizes a three-point strategy: Value must be created for the investor, the company, and the consumer. This "triangle" ensures alignment and long-term sustainability.

• Indochino’s key early challenge was to fix scalability problems—especially with supply chain and production.

  • Drew targeted investors who could provide both capital and operational value (like production expertise and better payment terms).
  • Quote:

    "At any time you're raising capital, you've got to create a triangle of value. There needs to be value for the investor, value for the company, and value for the consumer."
    — Drew Green [01:22]

• Deep diligence and hands-on collaboration were required, going so far as:

  • "The CFO and I working literally till 10 o'clock every night on this presentation and business plan."
    — Drew Green [01:56]
  • Drew and his colleague made about 12 trips to China and Japan over 10 months to secure deals.

    "We got it done, and without it, the brand wouldn't be here."
    — Drew Green [02:18]

2. Creative, Strategic Investments

[02:34]

• Three monumental partnerships:

  • Diane Group (supply chain investor from China)
  • Post Media (media investment: $40M in media spends for revenue share and warrants—a creative deal to grow Canadian market share)
  • Mitsui (Japanese trading house and world-class strategic partner for international expansion)

• Drew highlights the bespoke structuring of each deal, tailored to each partner’s strengths.

  • On the Post Media deal:

    "They basically pledged $40 million of media and I gave them revenue share on my Canadian business. ... So I was basically saying, okay, we're going to create a national brand with you."
    — Drew Green [02:56]

• Indochino hasn’t needed a new priced round since 2018, reflecting the sustainability and impact of these deals.

3. Navigating International Expansion with Mitsui

[04:00]

• Insight into Mitsui partnership:
  • Mitsui, a major Japanese trading company (one of Buffett’s "big five" investments), offered capital and a gateway to the enormous Japanese suit market (10–12 million suits annually).
  • Drew values Mitsui’s culture and spent three years building the relationship before taking their investment.
    • Quote:

      "They just. There's just the culture. There is. Is something I admire, and that's, for me, like, anybody I work with...I want to admire them, you know, and I do."
      — Drew Green [04:49]

4. Drew’s Entrepreneurial Philosophy: Value the Journey

[06:07]

• Drew prioritizes fun, experiences, and relationships as much as business success.

  • Quote:

    "I believe that it's the experiences that you have, you know, that is the real sort of treasure. ... Famously, the alchemist talks about the journey as the treasure, and that certainly I subscribe to that."
    — Drew Green [06:10]

• Emphasizes balancing hard work with making the most of life—both as a father and global citizen.

  • "As an entrepreneur, we all work really hard. I don't know if anyone works as much as I do. But you can make money. … But can you enjoy it? And can you have the full Experiences that are gonna define true happiness."
    — Drew Green [06:50]

5. Building a Personal Brand and Entrepreneurial Mindset

[07:32]

• Drew’s early successes (DoubleClick, sold to Google) influenced his career, as did maintaining relationships with former colleagues.
• He reframes entrepreneurship as being about self-brand and personal business:
  • Quote:

    "Being an entrepreneur is as simple as understanding you're your own brand and you're your own business. ... Whether that includes one to a hundred startups or it includes no startups and you're a lawyer, you can be an entrepreneur."
    — Drew Green [07:52]

Notable Quotes & Memorable Moments

• On the critical nature of operational value in investment:

  "Along with that $30 million came this incredible now 10-year agreement that reduced all of our costs, gave me 90-day payment terms and a dozen other things I could list. And so all of a sudden you've almost overnight fixed the P&L."
  — Drew Green [01:39]

• On building long-term relationships with investors:

  "I got to know Mitsui over probably three years before they made the investment, they offered a lot more than I ended up closing on because we just didn't need that much capital at the time."
  — Drew Green [04:38]

• On cultivating a fulfilling entrepreneurial life:

  "Everything from dreaming big and having big ideas and going and trying to execute them, to being a great father, to traveling all over the world and meeting great people. ... You can make money. It's gonna happen. But can you enjoy it?"
  — Drew Green [06:36]

Key Timestamps

• 00:38 – Triangle of value explained; Indochino’s first big capital deal
• 02:34 – Strategic capital partnerships: Diane Group, Post Media, Mitsui
• 04:00 – Mitsui’s importance, insights on Japanese market
• 06:07 – Entrepreneurial philosophy: balancing fun, life, and success
• 07:32 – Personal brand, early career, and redefining entrepreneurship

Episode Tone & Style

• Candid, energetic, and insightful—Drew’s optimism and openness shine through, encouraging listeners to think strategically and enjoy the entrepreneurial journey.
• Jon steers the conversation with curiosity and warmth, drawing out practical lessons without losing the personal, motivational edge.

For more episodes and resources:
Visit JonDavids.com