Episode Overview
Podcast: Making It with Jon Davids
Episode: 221 - "We Raised $5M with a Powerpoint" | Drew Green, Indochino
Date: October 17, 2025
Host: Jon Davids
Guest: Drew Green (CEO, Indochino)
In this episode, Jon Davids interviews Drew Green, the CEO of Indochino and a serial entrepreneur, about the trajectory of taking companies from the ground up—specifically, how Drew raised $5 million with just a PowerPoint presentation. They delve into the importance of relationships, how Canadian tech and e-commerce matured, the critical early missteps, rapid-fire fundraising rounds, and the resilient problem-solving required to achieve exponential growth.
Key Discussion Points & Insights
1. Early Career and the Power of Relationships
[00:00–01:35]
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Drew Green recounts his early days at DoubleClick (later acquired by Google, forming their ad business), managing a Manhattan team and closing huge deals.
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He credits ongoing relationships for his later ability to connect opportunities globally in tech and commerce.
"Some of those people that...work for me are still friends to this day. And actually a couple of them are still at Google."
— Drew Green, [00:35] -
Jon emphasizes that Drew’s story is threaded by powerful relationship-building and an ability to network across cities (NY, Canada, China, Japan), using what Drew refers to as the “triangle of value.”
2. Vision to Return and Invest in Canada
[01:35–03:22]
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Drew wanted to return to Canada to raise his sons in a Canadian environment, invest in Canadian entrepreneurship, and address the lack of funding and mentorship for Canadian startups—a “huge gap.”
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He recognized early (approx. 2012) that Canadian e-commerce, especially, lagged far behind.
"We sort of...I remember commuting from the States to Toronto...every week I drive up...and every Friday night...drive back...until we raised $5 million."
— Drew Green, [02:33]
3. Raising $5 Million Pre-Product—on a PowerPoint
[03:22–03:35]
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Drew raised $5 million in 3.5 months before a product existed, relying on a strong reputation and network, but also a capable, motivated team.
"So you raised five with what, a PowerPoint."
— Jon Davids, [03:22]"PowerPoint."
— Drew Green, [03:24]"There was nothing. It was a PowerPoint. But you also, to be fair, had a great reputation at this point."
— Jon Davids, [03:25] -
The round wasn’t even priced; it was a convertible note with a $40 million cap—“ridiculous” for the time, Drew reflects.
4. Challenges: Talent Gaps and Building in Canada
[04:49–05:36]
- Drew highlights that, in contrast to Silicon Valley or NYC, Canadian startup talent and technical capacity were limited.
- First-year missteps included issues with the platform’s development; nevertheless, they persevered.
5. More Fundraising and Turbulent Launch
[05:30–06:14]
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Before even launching, they completed another $25M round, part of which included a strategic media company investment—a “triangle of value” approach.
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The platform’s launch (on Canada Day) was rocky: $1,400 in sales was reported on Day One, and their largest supply partner pulled out last-minute.
"We launched and I think we did $1,400 in our first day. We had our biggest supply partner essentially pull out."
— Drew Green, [06:08] -
Despite chaos, Drew lauds the team’s perseverance and mental toughness, leading to a $1M day within a few months.
6. Coping with Success and Pressure
[06:14–07:36]
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Success brought its own stresses: valuations peaked at $225M, and despite rapid growth, team cracks appeared.
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After raising another $30M (“recapitalization”) and hitting a $10M month, Drew stepped aside—burned out by the pressure.
"As soon as the company was recapitalized...had just finished...a $10 million month...I stepped aside."
— Drew Green, [07:15]
7. Lessons from Early Setbacks and Scaling
[07:50–10:08]
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Jon asks about the emotional and tactical reaction to the disappointing $1,400 launch day.
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Drew’s team focused on solutions, not panic, trusting their vision for e-commerce in Canada—at a time when almost no big retailers were selling online.
"There was such...an incredible group of people that had a lot of mental toughness, that had a lot of belief that E-commerce in Canada needed to arrive."
— Drew Green, [08:16] -
Critical insight: The best marketing is product and price. They doubled down on the 5% of inventory that actually sold (“95/5 rule”), fixed platform issues, and relentlessly solved problems.
"If you have a product that's in high demand and you price it well...it will sell."
— Drew Green, [09:18] -
Jon underscores: Success stories aren’t about avoiding problems but solving ever-bigger problems with determination.
"People look at successful people and think [...] they just didn't encounter the problems that I encountered...they never avoided those problems."
— Jon Davids, [10:08]
Notable Quotes & Moments
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On relationships and loyalty:
"Some of those people that...work for me are still friends to this day."
— Drew Green, [00:35] -
On moving home and vision:
"I wanted my sons to be Canadian. I wanted to raise them Canadian. That was vision number one."
— Drew Green, [01:48] -
On audacious fundraising:
"We raised five...with what, a PowerPoint."
— Jon Davids, [03:22] -
On first-day turbulence:
"We launched and I think we did $1,400 in our first day."
— Drew Green, [06:08] -
On team resilience:
"Any problems we had in those early days, we just worked through."
— Drew Green, [09:00] -
On scaling:
"The best marketing was product and price....business is one thing, it's just about solving problems."
— Drew Green, [09:12]
Timestamps for Key Segments
- [00:00–01:35] — Drew’s DoubleClick days and the importance of relationships
- [01:35–03:22] — Motivation to return to Canada and formulating the business vision
- [03:22–03:35] — Raising $5M with a PowerPoint and a network
- [04:49–05:36] — Challenges building a startup in Toronto
- [05:30–06:14] — Additional $25M pre-launch, launch day catastrophes
- [06:14–07:36] — Growing pains, team cracks, and leaving as CEO
- [07:50–10:08] — Overcoming a slow launch, focusing on product/price, mindset of persistent problem-solving
Summary
This episode is a revealing, candid look at what it really takes to grow a startup, raise massive (almost unheard-of at the time) seed capital with little more than an idea, and handle both the soaring successes and brutal setbacks. Drew Green underscores the imperative of relationships, the need for bold vision (especially in nascent markets), and above all, the unglamorous but crucial grit of constant problem-solving. The big lesson: success isn’t a lack of problems, but an ongoing process of overcoming them—together, with an incredible team.