Lessons - The Investor Behind Lyft, Pinterest, and Warby Parker | Courtney Reum - M13 Co-Founder

Summary

Success Story Podcast with Scott D. Clary

Episode: Lessons - The Investor Behind Lyft, Pinterest, and Warby Parker | Courtney Reum - M13 Co-Founder
Date: April 9, 2026
Guest: Courtney Reum, Co-Founder of M13

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Episode Overview

This episode features a candid conversation between host Scott D. Clary and Courtney Reum — entrepreneur, investor, and co-founder of M13, a venture capital firm with early investments in brands like Lyft, Pinterest, and Warby Parker. The discussion centers on lessons learned across the entrepreneurial spectrum: from launching one of the first carbon-neutral spirits brands (Veev) to sourcing investable startups, understanding product-market fit, creating exit optionality, and leveraging pattern recognition. Courtney’s unique “operator and investor” lens brings depth to strategies around building, scaling, and successfully exiting startups.

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Key Discussion Points & Insights

Courtney’s Journey: From Operator to Investor

• Holistic Entrepreneurial Experience

  • Courtney’s career spans roles as an advisor, operator, and investor — including building VEEV, writing "Shortcut Your Startup," and now co-founding M13.
    • “You've done all of it. You've been the advisor, you've been the operator, you've been the capital allocator. So the lens that you see entrepreneurship through is super vast, which is awesome, right?” – Scott Clary [01:25]

• Building the First Carbon-Neutral Spirits Brand

  • Early adoption of sustainability with VEEV; donated 1% of sales to environmental causes, pioneering a now-common approach.

The Blend of Intuition & Execution

• Entrepreneurial Mindset: Operator-Investor Synergy

  • “Iron sharpens iron”—practical experiences as an entrepreneur inform investment decisions and vice versa.
    • “Being an investor has made me a better entrepreneur and being an entrepreneur has made me a better investor… That’s kind of mindset we have for our whole firm, which is pretty unique and really important.” – Courtney Reum [02:55]

• Future of Consumer Behavior

  • M13 focuses on identifying where “the puck is going” (borrowing a hockey metaphor) to catch new consumer trends through information asymmetry.
    • “In the world we live in, the information is here. It's just not evenly distributed… If I can have some information asymmetry on anything, I see some trends myself, I talk to other people… But I do think just a little bit of that, I'll put it in hockey terms for, you know, where the puck is going is really important.” – Courtney Reum [03:29]

Building Playbooks and Pattern Recognition

• From Grit to Repeatability

  • The first startup required sheer hustle and “trying to will it”; later ventures benefit from pattern recognition and tactical execution—not just brute force.
    • “So that was kind of more like trying to will it and grit and a little more hustle. Now I think to your point, almost everything we do has some ability, some element of like repeatability or pattern recognition along with some newness.” – Courtney Reum [05:38]

• No Universal Startup Playbook

  • Every industry and product has unique nuances; ongoing learning and feedback loops are critical.
    • “There isn't just one playbook that works for everyone.” – Scott Clary [04:48]

Product-Market Fit, Scale, and Exit

• Product-Market Fit in Highly Regulated Industries

  • Spirits industry was attractive due to high exit multiples, yet extremely challenging for newcomers (distribution, regulation, restricted data).
    • “It's really hard for new incumbents… It's harder to get accurate data, especially then, of who my consumer was, what their purchase occasion was… A lot of things you have to really, I would say, in many ways, do by hand.” – Courtney Reum [07:27]

• Signals of Product-Market Fit

  • Anecdotal and quantitative signs: reorder rates, presence in high-end bars/restaurants, recurring sales in key locations.
    • “The simplest metrics are stuff like reorder rates and same store sales because if people are actually reordering veeve or calling for it, that starts to tell you you have something.” – Courtney Reum [11:22]

• Building with Exit Optionality in Mind

  • Entrepreneurs should always consider the possibility of an exit—even if uncertain. Carefully lay “breadcrumbs” to get noticed by strategic acquirers and build momentum (e.g., targeted billboard buys, joining industry groups).
    • “If there's even a chance you might want to sell your company, you need to build it with that in mind so that you have the option but not the obligation…there is a whole art to the…what I'll call kind of like, you know, we did some things to get noticed. We left breadcrumbs.” – Courtney Reum [12:29]

• The Art of Creating Momentum

  • Crafting the “appearance of momentum” can attract buyer interest, even if your company isn’t yet a “need to have.”
    • “At Goldman, we always say something effect of momentum or the appearance of momentum. You have to create your own luck and create your own momentum so that people all of a sudden go, wait, I'm hearing about Vee everywhere. Maybe I should call them and find out more.” – Courtney Reum [13:58]

Venture Capital Perspective

• Backing Founders with Big Visions

  • Investors seek teams aiming to build large, scalable enterprises—not just quick $25M exits.
    • “What we do look for is we want someone who has a big vision… VCs have to back people who tell us they want to build something big, but we have to believe it… The first offer that comes across the table, then they want to take and you're like, wait, that's a lot.” – Courtney Reum [14:46]

• Alignment on Objectives and Timelines

  • Tension can arise if founders are tempted by modest, early acquisition offers; clarity and honesty are essential in the founder-investor relationship.
    • “That's why we just try to be upfront about both our objectives. No one's trying to hang on too long, no one's trying to get you to do something that we can't do. But if you want to build something there, you know, there are those things that, who knows how big they can get, like an open AI.” – Courtney Reum [15:58]

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Notable Quotes & Memorable Moments

| Timestamp | Quote & Context | Speaker | |------------|---------------------|-------------------| | 01:25 | “You've done all of it… the lens that you see entrepreneurship through is super vast, which is awesome, right?” | Scott Clary | | 02:55 | “Being an investor has made me a better entrepreneur and being an entrepreneur has made me a better investor… That’s kind of mindset we have for our whole firm, which is pretty unique and really important.” | Courtney Reum | | 03:29 | “In the world we live in, the information is here. It's just not evenly distributed… But I do think just a little bit of that… where the puck is going is really important.” | Courtney Reum | | 05:38 | “That was kind of more like trying to will it and grit and a little more hustle. Now…everything we do has some element of… repeatability or pattern recognition along with some newness.” | Courtney Reum | | 11:22 | “The simplest metrics are stuff like reorder rates and same store sales because if people are actually reordering veeve or calling for it, that starts to tell you you have something.” | Courtney Reum | | 12:29 | “If there's even a chance you might want to sell your company, you need to build it with that in mind so that you have the option but not the obligation.” | Courtney Reum | | 13:58 | “At Goldman, we always say something effect of momentum or the appearance of momentum. You have to create your own luck and create your own momentum…” | Courtney Reum | | 14:46 | “We want someone who has a big vision… we have to back people who tell us they want to build something big, but we have to believe it…” | Courtney Reum |

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Timestamps for Important Segments

• 01:25 — Courtney’s wide lens: experience as advisor, operator, investor
• 02:55 — Value of blending entrepreneurial and investor roles
• 03:29 — Pattern recognition and predicting consumer behavior
• 05:38 — First startup: learning through grit vs. repeatability
• 07:27 — Navigating challenges and metrics in the spirits industry
• 11:22 — How to identify product-market fit in practice
• 12:29 — Building with the option (but not obligation) to exit
• 13:58 — Creating and signaling momentum for acquisition interest
• 14:46 — What investors look for: vision, scale, alignment
• 15:58 — Navigating founder-investor alignment and exit timing

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Key Takeaways

• Blend of Experience Is an Edge: Being both operator and investor sharpens decision-making and empathy.
• Future-Oriented Pattern Recognition: Information asymmetry and “seeing where the puck is going” create outsized opportunities.
• Product-Market Fit Is Nuanced: Combination of hard metrics (reorders, sales) and soft signals (“cool” placements, customer behavior) matter.
• Build with Exit in Mind: Optionality is power; always lay the groundwork even if a sale isn’t imminent.
• Strategic Storytelling: Perceived momentum and targeted visibility attract suitors—smart “breadcrumbing” pays.
• Investor-Entrepreneur Partnerships: Alignment on ambition and timelines is vital; clarity beats assumption.

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For more lessons or to hear the full depth of Courtney’s stories, check out the full episode at successstorypodcast.com.

Transcript

[Scott Clary]

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[Podcast Narrator / Intro Voice]

Now in this lessons episode, explore how successful startups are built through a blend of intuition, pattern recognition and strategic execution.

[Podcast Host / Advertiser]

Discover how to identify product market fit

[Podcast Narrator / Intro Voice]

through real demand signals. Understand why building with an exit in mind creates optionality and leverage. And uncover how aligning vision, momentum and consumer insight drives scalable and investable businesses.

[Scott Clary]

So I'm assuming like we didn't even bring it up yet, but the book that you just wrote shortcut your startup, that's learnings from I'm assuming all the way back to Goldman Sachs, all the way through to building VEE, all the way through to M30. Like these are learnings along every single function of an entrepreneur. Raising money, raising capital, selling a product, product market fit. So I mean, it's interesting because you've done all of it. You, you've been the advisory, you've been the operator, you've been the capital allocator. So the lens that you see entrepreneurship through is super vast, which is awesome, right? It really is awesome. And I think that when you build out like your first company, I'm also curious about one thing in your first company because I think that if I read this correctly, this was one of the first companies to ever, if I'm not mistaken, be a carbon neutral spirits company. And you donated 1% of all the sales to environmental causes. So this, this now is not so abnormal. This is very common. But back then this was sort of new, innovative. When you look at what you did there, I'm assuming you still have the lens of looking for companies that are

[Podcast Host / Advertiser]

doing things differently, doing things in a

[Scott Clary]

novel way, finding new ways to resonate with the audience in the market.

[Podcast Host / Advertiser]

How do you source out that thing

[Scott Clary]

that could move the market, make the brand more trustworthy with who they're trying to sell to, like ultimately create that evangelism? Cause that's what brand is. Can you, can you ignite that evangelism in your customers? Right.

[M13 Founder / Entrepreneur Guest]

Yeah. Yeah, I think, you know, it's. That is. It's funny because our. For my. My current holding company called M13, which is, as you kind of pointed out, I like to feel entrepreneurial. I like to also invest and I like to just build things. And so it kind of gives us a container where our, you know, the main thing we do is consumer tech focused venture capital funds. But we've also launched a bunch of our brands, which I'm happy to talk about. And I think for me and my brother especially, it's a lot of fun to some days be more entrepreneurial someday have your investor hat on. And certainly it's the virtuous cycle of being an investor has made me a better entrepreneur and being an entrepreneur has made me a better investor. And to stay entrepreneurial, iron sharpens iron. Like when I'm talking to someone about a company we invested in, a lot of times I can say it from a place of like, I've tried this recently or I failed at this recently. Not just, oh, I hear everyone talking about this, but I'm pretty. Pretty hands off and pretty removed. And I think that's kind of mindset we have for our whole firm, which is pretty unique and really important. And I think in terms of our North Star, what we're looking to be the best at with what we're doing is future of consumer behavior. And so the. There's not like one way to describe it, but I would say in the world we live in, the information is here. It's just not evenly distributed. And so to the extent I can have some information asymmetry on anything, I see some trends myself. I talk to other people. I'm lucky to know XYZ person. I mean, it used to be something where you'd go to the athletes to get the latest supplements or say whatever it is. We try and do that in a myriad of ways. But I do think just a little bit of that, I'll put it in hockey terms for, you know, where the puck is going is. Is really important. Really hard to do, but really important.

[Scott Clary]

Yeah, I love that because I think that you know, whenever you see somebody that has multiple successes and, and you're not just an investor now, now you spin up your own companies. Like I, I love to ask about the playbook and I want to understand like what the playbook is for a successful startup because now it's not just grit. I mean, I mean it will be a lot of grit but hopefully it's not as much grit and a little bit more tactical execution after, after doing it a few times. But then there's also nuances. So like, you know, in any industry it's not going to be the exact same playbook. There's similarities, there's a checklist, but there's a lot of things that are like niche and industry specific. So it's like the mindset of sourcing for the knowledge is going to give you that advantage or give you insight into the consumer, build those feedback loops. I think that's like a super, super valuable lesson for entrepreneurs because there isn't just one playbook that works for everyone.

[M13 Founder / Entrepreneur Guest]

But yeah, and I do want to clarify because you said really, you specifically asked about first company and to your point, I do think it was grit, you know, and I do think, I want to clarify something I said earlier because I do think like some of the hustle culture stuff is a little, is, is real good and bad and I don't, I don't believe in kind of hustling for the sake of hustle or busyness with a why if you will. I believe in kind of velocity which is like speed but with direction. And you asked specifically about the first company which I don't think we had any velocity because we didn't really know where we were going or what we were doing. So that was kind of more like trying to will it and grit and a little more hustle. Now I think to your point, almost everything we do has some ability, some, some element of like repeatability or pattern recognition along with some newness. Because if we're starting or investing in something and the Metaverse or Web3 or AI, not many people have done much with it. Right. So we're, we're building the plane as we fly.

[Scott Clary]

So we'll go into that in a second. I want to, I'm not going to spend too much time on, on, on, on the first startup, but I do want to just walk through that. First startup was a success. You, I mean you, you eventually exited it. I wanted to speak about that journey. So as a first time entrepreneur building a company first, first company to exit is not common for most people. So the process of building that up, when did you understand how you'd like to carry that company? You know, what was the milestone or the revenue number where you're like, hey, this works. We have product market fit. Let's continue to grow. We don't need the playbook for the entire cycle of growth. But what's that product market fit point when idea is validated. And then also after that, walk me through the exit, the acquisition, and then the pivot into M13.

[M13 Founder / Entrepreneur Guest]

Sure. I mean, I think the, you know, one thing that really attracts us to spirits on paper was that because innovation was so hard. And I won't go into all the reasons. It's really hard, but it's. It's really hard for new incumbents. It's really hard to get distribution. There's no pivoting to some other product. You've got something sitting in a bottle, you know, I mean, and you're really at the behest of large. I mean, we did spirits, which is a little different than wine and a little different than beer. So what I'm saying is pertains mostly to spirits, but you can't really sell direct to consumers. So I don't really. I don't really. It's harder to get accurate data, especially then of who my consumer was, what their purchase occasion was. I mean, all kinds of things you have to really, I would say, in many ways, do by hand. And so one of the things that attracts us to spirits was there. There are companies that sold, you know, an average exit could be easily like 8 to 12 times sales because it's that hard to do. So to the victor goes it spoils. And you know, there's, of course there's companies that sold for a couple times sales, but there was, you know, Grey Goose, I think. I think Bacardi bought Grey Goose. I haven't said this stat out loud in a while, but I think something like 14 times sales because it was that accretive because it was growing so fast and they needed a vodka. I think multiples have come down and things have changed a little bit. That's what it was like then. So we, we saw that opportunity. Of course we should have known there's a catch, that the reason something could go for 10 times sales is because

[Scott Clary]

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[Scott Clary]

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[M13 Founder / Entrepreneur Guest]

Still nothing. Still in many ways, still nothing harder. I've tried to do with lower, lower odds. If you start from a, you know, kind of a standing start, I think if you have unfair advantages, which is what we're always looking for, or relationships, thankfully I, I do now. So I'm put a gun to my head to start a spirits brand, which might be about what it takes. But, but I think, I think the, I think the point where we had something, it's. It was, you know, we never had the total number of distribution points of like an absolute or a grey goose, of course, but we had. We were in the very high end places. We were in kind of like the trendier. We were very on premise, which means we were in bars, clubs, restaurants in like major metros, New York, Miami, Louisiana. You get it? So we had it at those places. And I think, I think the simplest metrics are stuff like reorder rates and same store sales because if people are actually reordering veeve or calling for it, that starts to tell you you have something. So that's kind of the anecdotal stuff. And then there was a whole bunch of metrics in terms of cases sold in revenue and reorder rates that kind of let you know that hey, you might be in the ballpark of something that someone wants to acquire. The funny thing is I would say we all read about these companies that everyone's falling over ourselves to buy and this and that. But the reality is even most things that get sold, and we talk about this in our book, is, is like most things are a nice to have, not a need to have. And Veev, in all candidness was very much that like people were interested but no one was willing to like you know, give up their firstborn for it. So now it's a dance of like making sure you. Our last chapter of our book, Shortcut yout Startups, talks about how assuming you think you might want to sell it, if there's even a chance you might want to sell your company, you need to build it with that in mind so that you have the option but not the obligation. And I think what a lot of people do is go, I don't think I want to sell it. And even if it's less than 50, 50, then one day you decide you want to. Doesn't mean all is lost, but it means you have some work to do. Because there is a whole art to the. What I'll call kind of like, you know, we did some things to get noticed. We left the breadcrumbs. One time we bought a billboard right by our biggest distributor so that people saw it, stuff like that, to kind of give the. The appearance that we were doing well, even though we were. But if a tree falls in the woods. So it's a lot of. It is a lot of those breadcrumbs, and it's a lot of, you know, I joined some industry groups and went to a couple conferences with people that I'd never met to try to build that relationship. Just so it wasn't like a thirsty, cold email saying, hey, want to buy me? Slide a number across the table, right? And there's. There's a whole arc to that, which I don't think I've mastered, but I've mastered it enough that. That have been able to sell some stuff. But I think that's a huge. You know, some people I talk to get. Really, no one's called me to buy my company. I'm like. And no one probably ever will. But that doesn't mean it's not a good company. It doesn't mean someone won't buy it for a number that makes you very, very happy. You just have to put on their radar and make them. You know, at Goldman, we always say something effect of momentum or the appearance of momentum. And, you know, you have to kind of create your own luck and create your own momentum so that people all of a sudden go, wait, I'm hearing about Vee everywhere. Maybe I should, should call them and find out more. You know, that was, that was kind of the, the goal.

[Scott Clary]

Is that something that you look for now, like, when you put money into companies, do you look for owners that are building to sell, that have that mindset from the asset, or is that something you train over because they're just walking through like that?

[M13 Founder / Entrepreneur Guest]

Well, I think what we do, you know, in venture, the goal in general is not to. With some exceptions, like you're, you know, my. I have a fund with a finite life expectancy, so it's not great if someone holds it for 20 years, something they built, even if it's, you know, even if it's a great company. So, yeah, we, you know, we have to look for liquidity. But I think the flip side is what, what we do look for is we want someone who has a big vision, someone who, as I said, we want to be at the forefront of consumer behavior. So those companies can be big. So I want someone with a big vision. And don't get me wrong, I've, I've sold companies in the tens of millions and the hundreds of millions that I've started, but I'm not, you know, for it to be a venture backed company. Like I can't, like if it took one check and sold for 25 million, a lot of people would probably be happy. That's not how venture capital works. So it's, it's power laws. We have to, you know, back people who tell us they want to build something big, but we have to believe it because occasionally you get the person who says they want to build something big, they've got a little lightning, a bottle and the first offer that comes across the table, then they want to take and you're like, wait, that's a lot.

[Scott Clary]

That's not, that's not as much. It's a lot for somebody who's never gotten a check before. But yeah, I got you.

[M13 Founder / Entrepreneur Guest]

And that is attention. And look, we always want what's best for the founders, but that's why we just try to be upfront about like, what are, what are both our objectives. Like, no one's trying to hang on too long, no one's trying to get you to do something that we can't do. But if you want to build something there, you know, there are those things that, who knows how big they can get, like an open AI.

[Podcast Outro Host]

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