221 - "We Raised $5M with a Powerpoint" | Drew Green, Indochino

Summary

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.

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Key Discussion Points & Insights

1. Early Career and the Power of Relationships

[00:00–01:35]

• Drew Green recounts his early days at DoubleClick (later acquired by Google, forming their ad business), managing a Manhattan team and closing huge deals.

• 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]

• 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.”

• 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]

• 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]

• Before even launching, they completed another $25M round, part of which included a strategic media company investment—a “triangle of value” approach.

• 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]

• Success brought its own stresses: valuations peaked at $225M, and despite rapid growth, team cracks appeared.

• 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]

• Jon asks about the emotional and tactical reaction to the disappointing $1,400 launch day.

• 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]

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Notable Quotes & Moments

• 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]

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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

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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.

Transcript

[A]

This clip of Making it with John Davids features John talking to Drew Green, CEO of Indochino. You just hit on something there, which is you had a lot of relationships. So I think being early days, DoubleClick, and for those who don't know, DoubleClick is the company that was acquired by Google and effectively formed Google's advertising business, which is the whole company today. So super great timing, place to be. And you were also like a rock star. Weren't you telling me that you were capturing whales there? Weren't you getting huge contracts for DoubleClick when you were there?

[B]

Yeah, I was really fortunate, again, that, like, I was in a position in my 20s, living in Manhattan, managing a team, closing big deals. Some of those people that. Most of those people that work for me are still friends to this day. And actually a couple of them are still at Google. Yeah, man, we were closing big deals.

[A]

So you're, you're in New York city in your 20s, closing deals for what will become the biggest advertising company in the world. Then from there, what you did was you maintained relationships. Because I think the thread throughout the story is you have relationships. I mean, having friends in Canada and China and New York City and Japan and being able to connect the dots, as you said, the triangle of value. You have to have a lot of points to be able to find the right ones for that triangle at every given moment in your journey. And can you talk about. So you have that amazing experience at DoubleClick and then maybe some stuff happened in the middle, but let's get to shop Ca. What was the big idea here? And just give me this incredible story.

[B]

Yeah. So, you know, when I think back, it's about 14, no, only 13 years. I was still in the U.S. my kids were super young. We were having a blast, right? Making a lot of money, doing all the things that you do as a young family. And I don't know, I remember feeling like I wanted to be Canadian again. It was really important to me to go back, to go back home. And, you know, we had our green cards and we were, we were settled. But for me, I kind of had three things as part of my vision. One, you know, I really wanted my sons to be Canadian. I wanted to raise them Canadian. So that was vision number one. Vision number two is, yeah, I could stay in the US and start more businesses and invest in businesses, but why don't I go back to Canada, invest in myself and start businesses there? And then number three, you know, kind of just talking to so many people back home, I Just saw this huge gap where Canadians weren't getting funded the way they needed to, weren't able to raise the capital for great ideas, and needed mentorship. And so those were my three visions. And so coming back, my first thought, and obviously it was something that I kind of knew how to do, was, hey, E commerce in Canada really needs some investment. It really needs something. At the time, there was nothing. And so, you know, we sort of. I remember commuting from the States to Toronto. This is true story. Actually, every week I drive up to Toronto, and then every Friday night, I would drive back to see the kids and Andrea until we raised $5 million. And so that took us. Took us about three and a half months. We raised five, and then we proceeded to build for a year.

[A]

So you raised five with what, a PowerPoint.

[B]

PowerPoint.

[A]

So there was nothing. There was no. There was nothing. It was a PowerPoint. But you also, to be fair, had a great reputation at this point. You had. You had just come from DoubleClick.

[B]

Yeah, you know what? Sure. But I also had great people around me. You know, I think, you know, everything is done within a team. You know, I mean, it's never one person. And I appreciate you saying what you just said, but, you know, there was some. A lot of enthusiastic, hungry entrepreneurs around me that were like, okay, Drew, let's. Let's do this. Right? And so we all got together and were able to. To do that, I think, in record time. It was. It was not even a priced round. It was a convertible note with, I think, a $40 million cap, which is ridiculous, right?

[A]

This episode is brought to you by my AI Growth Cheat Sheet, available now at johndavids.com AI if you're a business owner and you're wondering how to use AI to actually grow your business, this is the answer. It's a fully custom AI Growth cheat sheet that'll give you the tools you need to grow your business today. Available right [e-mail] AI just answer a few questions, wait a few seconds, and you'll have your list of tools, and it's free. Get it right [e-mail] AI especially back then. I mean, these days it's more common, but back then, no, you did not raise that on us. And there was a seed round. A 5 million seed round was crazy.

[B]

Seed round. No product, no revenue. So we did that, and then we proceeded to build. And what I found out was that at the time, there wasn't the same available talent that there was to build companies in the U.S. so, you know, there's lots of great technologists and salespeople and all that, but not the startup sort of talent base that Toronto has now or, you know, that's here in San Francisco. And, and, and, and so I think we had some missteps in our first year building at the platform. I remember the launch being Canada Day, and, and sorry, I left out that we had then closed around a 25 million another year forward.

[A]

Small details. So you raised five and then before launching, you raised another 20.

[B]

Another 20, yeah.

[A]

And how, just briefly, how did that even come? Did you need the 20 or did you already have that in your pocket? How did that even come to be.

[B]

So it was actually, it was actually 25. And we, we did part of it as strategic. Right. Again, that triangle of value. I said, okay, well, we'll build the platform, we'll figure out the merchants. And not a lot of people were selling online at that time, but we need demand. Right. Like, people need to know about this thing. And so we partnered with a media company and they invested along with others, and we closed that round pre launch, pre revenue, and then it didn't go well. Right. We launched and I think we did $1,400 in our first day. We had our biggest.

[A]

Holy.

[B]

Yeah. We had our biggest supply partner essentially pull out because parts of management hadn't approved it and other parts had. And so it was just chaos. Right. But what an incredible team we had. Like, they persevered, they figured it out, we righted the ship. We did our first million dollars. We had our first million dollar day, 1, 2, 3, 4 months later. And then something interesting happened. Jonathan is, you know, when, when the stakes. So people often think you find out who people are when things go bad. Yes, sure. But you actually find out a lot about yourself and you find out a lot about everyone when things are really good. And, you know, if you think about it like we had gone from zero. I think at our peak, we were valued at $225 million in a very short amount of time. And there was starting to be some cracks, right. Some cracks in that amazing team and including myself, the stress, the pressure. And so, you know, we had raised that. We raised another 30 million in May of 2014. And, and then, you know, as soon as the company was recapitalized, it had 20 million in the bank. It had just finished, I think a $10 million month. And I stepped aside, didn't want to do it anymore.

[A]

And. Sorry, how, how long into the journey was this?

[B]

Like two years no, this would be about. Well, remember I started the company well before I came back to Canada. So I actually started the company in 2009 incorporated. So it was kind of five years in for me.

[A]

So. Five years in and just to go back for a second, there's a bunch I want to pick out there. But the first day you spend probably a ton on marketing. I remember seeing ads all over the place. You had a building across the street from your office that was branded and you sell $1,400 that day.

[B]

Yeah.

[A]

What did you expect to sell that day? And what is the feeling inside the office when you say, hey guys, 1400 bucks. That's the number.

[B]

Yeah, that's the, that's the proud thing, right? I mean, we never. Oh my God. What, what, what just happened? It was always like, oh my God, let's, let's fix this, right? There was such. Again, I'm not going to name their names, but it was an incredible group of people that had a lot of mental toughness, that had a lot of belief that E commerce in Canada needed, needed to arrive. Remember, Jonathan, this is when, like businesses were not selling online. There was no doordash, there was no Canadian Tire. Our largest retailer in the country wasn't selling online. Hudson's Bay at the time wasn't selling online. Like, nobody was selling online. And so we had this audacious and big goal and big dream. And to the credit of the team, I mean, any problems we had in those early days, we just worked through.

[A]

Can you, can you give us a sense, Drew, of like just one or two things? Because this is what I'm super curious about. You got $1,400 and then you have a million dollar day a few months later. What are one or two things that you did to make that shift?

[B]

What we figured out really quickly was that the best marketing was product and price. What I mean by that is like, if you have a product that's in high demand, and this is in the Chino now, right? If you have a product that's in high demand and you price it well and so you can make some money, but you price it well, it will sell. And so we figured out the sort of the 95.5rule really quickly as a business. And we focused on that 5% that would sell and had the 95% that wouldn't. But going back to that launch, I mean, part of the problem for us was actually the platform, right. Like we weren't even transacting properly. You know, the checkout wasn't working. Properly and all these other things. And so but again, like nothing really at that point had phased us. We were just figure it out, let's solve, solve, solve which I always say, like business is one thing, it's just about solving problems. Right.

[A]

I think that's, that's a point just, just to nail that because people look at successful people and think, oh well, they, they just didn't encounter the problems that I encountered and you know, they were able to avoid those problems. They never avoided those problems. They probably had problems that you never even got to because all they were doing was just solving along the way. And I, I love also that you said it never phased us. You know, the $1,400 day didn't even phase us. It was just that's the start, let's fix it. And that's the attitude you got to have. Thanks for listening. Get my best stuff to your [e-mail] we'll talk to you next.