09: Angels of Shopify investing collectively and lessons on following your gut - Atlee Clark, Angel

What do you get when you mix U.S. national security, angel investing, and kids’ pajamas? Atlee Clark. Proud Canadian Atlee took a hard pivot from the public sector to the tech world, first through a nonprofit called the C100, which supports entrepreneurs, and later at Shopify, focusing on 0 - 1 initiatives. Similar to other angel collectives emerging at the time like Hashtag Angels and Operator Collective, Atlee tapped into her executive network at Shopify to connect with other female leaders who were looking to invest on the side. 

What began as informal conversations about investing and advising after the working day coalesced into Backbone Angels, a collection of executive tech women sourcing angel opportunities collectively and making investments individually. Backbone was started in 2021 and has amassed a portfolio of over 40 early-stage startups, including Bird&Be, 1Password, and Blume.

Atlee tells us what it’s like to balance functioning as a cohesive unit while making individual investment decisions. Plus, we get to hear about her journey as a small business owner and what motivates her to invest in what she wants to see in the world. 

Atlee writes angel checks of $10k to $20k, ideally at the friends and family round or at pre-seed, focusing on startups that address challenges for parents, small business owners, and Big Tech execs—three areas she intimately understands as the end user. Backbone Angels focuses on companies led by Black, Indigenous, and Women-led startups. 

Highlights:

• Atlee hopped on a one-way plane to San Francisco and left her U.S. national security gig in Washington, D.C., behind to head up a nonprofit organization supporting Bay Area Canadian tech entrepreneurs (and she’d never even worked in tech!)
• She met early Shopify execs who convinced her to come work for the company doing developer relations and the app ecosystem. Casual conversations about investing and advising with her peers led to the creation of Backbone Angels.
• Atlee prefers to follow her own intuition with early-stage investing, but she does have a tried-and-true framework for determining if a deal is right for her. She shares her tips for working as a collective and the reason she believes you should never overthink a “no.”
• Angel investing is a side hustle for Atlee (Remember, she’s also a Shopify exec, small business owner, and mom), and she prefers it because it fulfills her in a way that going full-time wouldn’t.   

Resource:
Want to Angel invest with other operators and learn from the team at Hustle Fund? Check out Angel Squad and resources created by Brian Nichols

• (00:00) - Atlee Clark, Angel: Canadians breaking into tech and now investing with intuition and purpose
• (01:33) - Building an ecosystem for Canadian tech founders: the story of becoming the first CEO of the C100
• (06:38) - Meeting Tobi Luke and joining Shopify: a new adventure pre IPO
• (09:34) - Founding Backbone Angels: a collective of senior leaders at Shopify coming together to write checks
• (15:27) - First Investment: The power of patience and a developing a personal investment thesis
• (23:21) - Worst Investment: Trust your gut and staying patient
• (29:20) - The art of feeling a "no"
• (30:54) - Best Investment: Highlighting Top Performers Calico and MIrza
• (32:59) - Resilience in Founders: Overcoming Challenges
• (34:15) - Current Investment Strategy: Today's Focus
• (38:21) - Sourcing Deals: Networking and Connections
• (44:46) - Lightning Round ⚡

Creators & Guests

Host

Shaherose Charania

Venture Investing at @CakeVentures and @joindvc | Always helping founders | Raised on Atari, MS-DOS, Bollywood & Hip Hop. 🇨🇦in 🇺🇸

Guest

Atlee Clark

Senior Leader at Shopify & Angel at Backbone Angels

What is First Funders?

Learn from angel and seed investors bold enough to write the first check.

How do they decide which startups to invest in?
How do they gain conviction in founders and ideas?
How do they add value to their companies?

Shaherose Charania and Aamir Virani are operators turned investors. They chat with their friends investing in early-stage technology startups and learn about their strategies to fund the best founders and startup companies.

If you are an angel investor or seed investor, you'll hear how others operate.
If you are a startup entrepreneur, you'll hear how investors filter and decide on writing that first check.

Atlee Clark, Angel: Canadians breaking into tech and now investing with intuition and purpose
===

[00:00:00] Welcome to First Funders. We have Atlee Clark here today, who is an angel and also the founder of Backbone Angels. And what I thought I would do is start and share about how we both know each other.

Shaherose: I think it was 2010, though. It feels like it might've even been earlier than that. And you were being interviewed for a role at a very important organization called the C 100.

, I was collaborating with Chris Albinson, one of the founding members. To create an organization for Canadian founders, which is so near and dear to me because I'm a proud Canadian who migrated to the U S in 2006 in a sort of one way flight, no money, no job, no visa, no network, like really on [00:01:00] my own.

And so this idea of supporting high potential founders in the Bay Area with mentors, investors was so exciting. And then when I met you as someone who would lead it, We became fast friends and collaborators and kept in touch over the years, even invested together. you invested in some of my SPVs as you got into angel investing.

And so I consider you a dear friend, someone who's had a huge impact on the Canadian startup ecosystem and beyond. And so with that, as a dear friend and collaborator, welcome Atlee to the show.

Building an ecosystem for Canadian tech founders: the story of becoming the first CEO of the C100
---

Shaherose: I'd love for you to introduce yourself and also share a bit about how you got into angel investing.

Atlee Clark: Yeah, absolutely. , I'm so flattered that you asked me, just two Canadians sitting on a podcast thanking each other. It's great. It's very on brand. so when you met me, , and I will say you were one of the guides into the Silicon valley that I had, and I'm so thankful for people like you, and Deb Landa, [00:02:00] and Chris, and Anthony Lee, and all of those people who showed me the ropes, because before I got on a one way plane to san Francisco I was doing my master's in U. S. national security. I had a totally different life path that was based on a totally different idea of what I wanted to do And somewhere in those two years in Washington, D. C., I was like, Oh, this is cool. But it's not for me. It was a very expensive way to figure that out.

But I'm glad I figured it out. And then I had an opportunity to get on a one-way, flight to San Francisco. It was 2009. And I was like, okay, well, where does one do a complete 180 on their career? . At the time I was like, well, sounds like San Francisco would be cool. I have one year on a working visa and also I went to California for the first time a couple years before, and I was like,

What is this [00:03:00] place? I need to live here. Anyways. So go out, have like no experience in tech other than just I don't no being an early adopter of things.

Like I was always a person who liked to tinker with the new things, but like. no credibility whatsoever. And luckily got invited to a couple Canadians in tech thing through people I knew and just started meeting all of you, like all of these people who had the same story as you, like, just like, and me to a certain extent of like, Hey, like, let's go where the thing is happening.

And find your people. and so I somehow convinced Chris and Anthony, who are venture capitalists, that I should be a person to run this organization., And I still remember them being like hemming and hawing.

And I was like, listen, guys, if I'm not good at this, you don't even have to fire me because I will be deported in approximately eight months. Because that's when my visa runs out. And if I'm good, then we get me a visa.

And they were like, that sounds like a [00:04:00] good, they're good venture capitalists. They'll take a little risk. And so, yeah, I joined I opened the bank account and there was less money in the bank account than I think. Like four months of what my negotiated salary was, which was really low. Because I was just excited to stay.

And yeah, and then I just hustled it and I got to learn so much from so many amazing people, VCs operators community folks, founders and it was such an incredible experience. And I just got like, An MBA in the Silicon Valley in four years without having to go to business school. So it was great.

Shaherose: I remember that and I remember mostly your openness, your quick learning, your passion and just your authenticity in all of this, right? Like you knew what you knew and you knew what you didn't know and you're like, I just did some time in DC and I don't know what this means, but I love it here. And you made it happen. You had a huge impact. You really ran the ship like a [00:05:00] startup.

Atlee Clark: Well, and it's so funny because only in hindsight, did I realize that's actually what I did? Like I hadn't read all the books. I wasn't listening to the podcast and then I look back on it and I was like, Oh, okay. We don't have enough money. Okay. Well, I guess I gotta go raise money. Okay. I'll figure that out.

It was, 2009, 2010. So I was like, okay, I got to figure out this social, mobile, local situation. And like figure that out quick. And everyone was so generous with their time. And when I think about angel investing, it's like one of the core reasons I went into it because I missed that open collaborative sharing.

Thing that happens I think uniquely in the Silicon Valley and it's just so fun to be a part of, and it's just such an energy filler. The other thing though, that I will say that was to my benefit, is I didn't care about who anybody was because they didn't know them. So I had no problem like picking up the phone. Like at the time, the [00:06:00] CFO of Google was canadian. I'm like, yeah, sure. I'll call that guy, whatever.

, cause I had no concept. I would call or walk up to people at events, like big investors and big executives. And I was like, yeah, whatever. Nobody in DC knows who they are. So who the hell cares? And I think it was a superpower for a little while because I was just willing to do it and then you were in an environment that was open to it. So it was pretty fun.

Shaherose: It was a fun time. You're a true builder. And from there, I'd love to hear then the journey of what happened for you after, and then what took you to then you sort of touched on it a little bit that you missed sort of the energy give that what led to that first check?

Meeting Tobi Luke and joining Shopify: a new adventure pre IPO
---

Shaherose: Why did you start investing after operating for almost 10 years?

Atlee Clark: Yeah. So, it's again, one of those hindsight things. One of the first events that we ever put on with the c 100 once I joined was we brought four rising stars in Canadian technology. And I did that in air quotes, rising stars. And one of them was [00:07:00] Toby Luque, who is the founder and CEO of Shopify. So he was one of the first Canadian tech founders I actually ever met. .

They were raising their series A, they were like 25 people. And he really stood out to me even at that time.

And then over my years at C100, he continued to be a person that I was fortunate to get to interact with and watch him grow his company. In that time Harley Finkelstein had also joined Shopify and he and I started working in my role at C100, like bringing, I think you came on one of these trips, like bringing like Canadians from the Silicon Valley up to Canada for startup events to like fuel the startup vibe in Canada.

And Harley and I put on a couple of those together. And so I got to know them really well over my time. And then eventually Harley called me and was like, We want you to come and work for us all the time. And to be honest, at the time, I was [00:08:00] like, I don't know if I want to go into a company and if I do I want it to be in Canada? Do I want it to be in the Bay? Like that was all sort of swirling through my head. But at the end of the day, I was like, you know what? I've met so many founders at this point. And Toby remains one that I think is unique, and someone I'm willing to like sign up to work for.

And so, joined them. The day I signed on, Harley called me and I thought he was going to be like, yo, I'm so excited to work together. He calls me and I'm like, Hey. And he's like, we're IPO ing in 10 months. I need you on a meeting in half an hour. And I was like, what? And then started my like, the whole new life, right?

Like talk about c100. I had no idea what I was doing. Like, hi, welcome to tech company about to IPO. I joined to run developer relations and the app ecosystem. And it was like a major part of the road show. And I was like, Whoa, ' kay, crazy. [00:09:00] Anyways, so fun, wild, I played a very bit role in it, but it was still like amazing to watch and be a part of.

And then I spent the next 10 years at Shopify in all kinds of different roles running app store, developer ecosystem, partner programs. I worked on our consumer

facing app, Shop. And then a year ago I was asked to come and join HR, which is a hard pivot for me but it's been so fun and so interesting. We're doing so many cool things. That is a whole other podcast.

Founding Backbone Angels: a collective of senior leaders at Shopify coming together to write checks
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Atlee Clark: And somewhere in that journey, there was a group of us, women, senior leaders inside Shopify, who just started getting together. Shopify was like , hyper growth, fastest growing company over a billion dollars ever.

Like it was, it's been a wild ride. And so there was a group of us that were just getting together just to be each other's like person, right? Like, Hey, , let's talk about what's going on. Hey, can I help you? [00:10:00] And it was also super fun. Like we just laughed all

the time and just had a great time and really had lots of respect for each other's work.

And then one night. We're sitting there and someone is like, Oh, I just met this company. Can you talk to them because they're having this problem and X, Y, and Z. And then someone else was like, Oh, I'm advising this company. And I think they should meet you. And then we all sort of realized that in different ways, we were either investing or advising companies and startups in different ways. And that there was benefit.

To this group of people for those companies, like collectively, we would be a net benefit potentially to certain founders. And then someone of course was like, should we just start investing together? .

And that started a really interesting discussion about like what that could look like and what that meant.

And then I don't know exactly what happened. I think it was like. International Women's day was [00:11:00] coming up.

And so someone was like, we have a deadline. This is our deadline. I think it was Arti sharma, who is one of my favorite people and a killer angel investor and LP.

And she was like, we're doing it. We're doing it. International Women's Day. She's also a brilliant marketer. So she was like, yeah, okay, this is what we're doing. And yeah, and made it happen in 2021.

Shaherose: Yeah. I remember that launch because around that time and a few years prior, things like Hashtag Angels had launched, which was a group out of a group of women out of Twitter who were angel investing together, Operator Angels launched. And I was so thrilled that you all came together and said, Hey, this Both as Canadians, but also as Shopify execs, we're here to cut checks and we're working collectively, but we're investing individually.

And I thought that was just brilliant because angel investing can be so lonely and we all don't know everything. And so to your point, if someone can help with this or diligence on that, you just become a smarter [00:12:00] investor when you have collective brainpower behind a deal. I love that. Thank you. And so for you personally, as you said, okay.

I'm in on this thing called Backbone. We're creating it as, we're, what is it that saying?

Atlee Clark: Oh, I'm building the plane while flying it.

Shaherose: That, right? But that's like how you roll. So it wasn't surprising. What was your why? You obviously had done a few investments prior to that, but like maybe generally speaking, like what's your purpose as an angel investor?

Atlee Clark: So I think it's twofold. So one is that energy I was talking about and like, both of my purposes are like, fairly selfish, but I think I don't see it as like a selfish choice in that I think both of those things come together to make it a net benefit for everybody involved, I'd like to think. But like for me, it was really two things. So one is like that energy fill.

So Shopify is an amazing place to work. I get to work with incredible people. It's also a big company, right? Like [00:13:00] I'm a company girl now, I guess. And so I was like, Oh, I love, like, I miss that, like that beginning phase where nobody knows anything and you're making like wild guesses. I'm very much a zero to one person. And like, that's even inside Shopify, that's where I get put. I'm not the optimizer. They're like, this thing is a mess or this thing has a huge opportunity. And that's great. And I get a lot of fulfillment from that, but it is a big company.

And so getting that like founder stories and talking to other investors and just like that, That mind itch,, you know, like even I remember you and I had a conversation when you were exploring a bunch of different things and I'm like, you were just like, thank you so much for taking the time. I'm like, Oh my God, no, this is so fun. Like, let's talk more about the future of things.

It's like, it's just a fun thing to do. And then I think my relationships with the other women in Backbone is so important to me. And [00:14:00] even in 2021, we knew that not everyone in that group was. Staying forever at the company.

There's only three of us who still work there today, but we have this thing. We have a thing that we all get to work on together. Like we probably could do it socially, but we like each other cause we like working together. And so it gives us a project. And that is just such a wonderful thing to be a part of. And I feel so fortunate to have that. And so , that drives a lot of it.

Shaherose: I hope people listening also get inspired , to really think about coming together as a group with people who you love spending time with, but don't necessarily work with every day. And also it's a non work relationship. And so it brings out different parts of you. And I hope people consider it because it's so good for the individuals involved, but equally awesome for the founders who get to access not just one angel, but many.

Atlee Clark: Yeah, I think that's some of my favorite and most valuable things I've done for my founders has actually been [00:15:00] introducing them to other people in the group and being like, I know exactly who you need to talk to about this. .

Shaherose: true network, true ecosystem is really a powerful force for founders. It really creates the momentum, shortcuts, all sorts of conversations and time gives you access to wisdom and money and talent. So yes, to building that kind of back and forth and left and right and up and down connection points.

So let's shift our attention to that first investment.

First Investment: The power of patience and a developing a personal investment thesis
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Shaherose: We've asked all our guests this question. Making that first investment often is like really memorable and comes with a lot of lessons.

Atlee Clark: So can

Shaherose: you rewind the clock and tell us about a story where you made your first investment?

What did you learn? If you can share the details about what it was. and what happened to it, that would be great.

Atlee Clark: Yeah, so I'll talk about the first investment actually that I made with Backbone because I think it was a really interesting lesson learned in investing in a group. So, we were so excited to do [00:16:00] this thing and we wanted to do it together. And there was power in that. And the check I wrote, it was like, relatively small, but not insignificant. I think though, it was very much driven by the collective versus would I still invest in that today? On my own. And I'm not sure I would.

Not because the company is a bad company. It's a great company. And the founders are so dedicated and they've made so many great pivots and like figuring it all out. It's called Bird and Bee and they're a fertility support company. And they're great. But I don't think I had my own personal investment thesis down yet.

And they probably wouldn't fit into it now. I'm a proud investor because like, I think they're wonderful. And I think what they're doing is smart and they're being competitive, it's a competitive landscape, but it's also such [00:17:00] an important conversation around fertility and building great, safe products in that space is something I believe in.

Would I invest in a similar thing today? Probably not. it's almost like a thing goes up in your head, you're like, I'm going to start writing checks. For me, at least, I was like, I got to write one soon because I just said that I am. It's a little bit of a weird identity thing.

And I think there's so much, ugh I don't know, ick, around, "I'm an investor", and then you gotta like prove yourself or something. I'm not sure. And that's probably 90 percent of my own head. But if you're thinking about angel investing, you're the type of person like me who loves shiny things and wants to invest in literally every founder they meet because like I've met like two terrible people who are founders and I'm like absolutely not but like everyone else you're like oh my god I want you so bad.

Like you have to be discerning of how you're gonna be helpful and then know [00:18:00] that like You can wait, like you can wait and that's okay too. And so yeah, I probably would have been a little bit more patient. But I'm still really proud of it as like our first backbone investment and the company's great. They're still doing really well, so I don't know. We'll see how it ends.

Shaherose: Yeah.

No. And I think what you're hitting on is, from what I know about you, you are someone who says what they're going to do and then does it. And that's why it probably felt like, Oh, I should invest quickly because , I want to live up to this new role that I've taken on.

And I think. When you think about investing, patience, discernment, like you said, are actually the key parts of the role, right? Is this the best deal that I've seen all month, all year? Is this something that I can evaluate that I can A, either be helpful in, like you said, or B, I'm discerning to be, sort of like top 10 in terms of founder quality or idea. Invest in and why

Atlee Clark: Yeah, absolutely. patience is such [00:19:00] an undervalued attribute for investors writ large and I think that if you meet an investor who does have patience, know that they are unique among many and , listen, there's time for urgency too. But I think there's there's just like right time, right investor, right company. yeah, So in terms of how I refined my investment thesis, which was really interesting when we started Backbone, the inbound was bananas. It was unmanageable and we weren't a fund.

We didn't employ other people. We were people with full time jobs at companies. Like, you know what I mean? Like it was like, Whoa. And I think that very quickly we had to figure out how to evaluate and how to say yes and no as quickly as possible.

And through that, we really started to see, Oh, like we're really [00:20:00] interested in different. Kinds of things.

One of the first things I made a very clear line on was a lot of people say that they invest to learn and I love that, like I'm all for learning but I also felt like I was in a part of my life and still am, I have two young kids, I have my own startup, I have a job, like all these things. I was like, Ooh, I'm not here to learn. I am here to invest in things that I want to see in the world from my particular point of view. And I have three points of view of which I look at companies, like who I am. So one, I invest in things that address challenges for parents. I am one. Invest in challenges I see as a small business owner, because I am one. And then invest in challenges I see as being a senior leader inside a large tech company. [00:21:00] Okay, great. But not like, software building tools, but that space.

So then being like, okay, because I wanted to be able to quickly discern whether I was in or out. And if one of those, if it wasn't tickling one of those things, it wasn't happening. In terms of who, angel investing, is not rocket science. I'm not really trying to take this space thing too far, but I don't think it is.

Like, it's a big guess. , I think sometimes angels trick themselves into believing they're VCs, and VCs are very different.

First of all, it's not your money.

Second, most of it's not your money.

Second of all, you usually have, like, a full organization that's, like, research and networks experts that are helping you make these decisions. Angel is like, I think so?

And I really try to approach it that way. like, I don't take myself too seriously. Like, I, cause I just don't think you should. And so when it comes to who I invest in, I'm like, okay, do I believe this problem, [00:22:00] has the potential to be a large player in their market and make a lot of money. If yes, does the person who is telling me that they can

do this, do I think they have an above average chance of doing that thing that they say they're going to do? If yes, then okay let's get into it and let me get to know you a little bit better and make me feel confident that, yeah, you do have that above average chance of making that thing happen.

Shaherose: Wow. So it sounds like that first investment in a space that really you wouldn't be an active customer in. You don't feel that pain tipped off this whole process of you really getting clear on where you want to invest and how. Some people do say only for learning, right? And then they go off into spaces, no pun intended, that.

They don't really know, but , that's the joy for them, right? That's the purpose is to learn. And in this case, You're like, [00:23:00] Hey, I just want to invest in spaces. I know because I am the customer. I am a parent. I am a small business owner, which you should definitely share the story about that in a second.

And three, I am a corporate executive. And if you take all those three customers, that's a lot of different companies and then secondly, evaluating the founder. I love that. I love that as a lesson.

Worst Investment: Trust your gut and staying patient
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Shaherose: Now let's now think about, you were saying, Hey, I haven't met a lot of bad founders, but investing in general, isn't all easy

So I'd love to hear about what we call the worst investment or just a really standout challenging moment. With an investment that you made and what lessons did you learn from that?

Atlee Clark: Yeah. So I think, I have sort of two half answers, if that's okay.

Am I allowed? Okay, great. so the first is actually like an almost investment, that I'm glad I didn't make,

and I'd love to attribute it to some sort of like epiphany, or some sort of insight that I had, [00:24:00] but it was like dumb luck. and I think it actually reinforced the patience thing.

So, I don't think I'd come to that realization fully yet, but then this sort of forced me to be patient. So basically it was like, okay, yeah. I think I'm in ,

it was weird. Cause Backbone, we invest in women led companies. So there's like, we have a little bit of a guideline in terms of like, how, like what roles women play in the company. Most of them are the founders. But in some cases it's been like a mix and there's a situation where it was The founder was a guy and then instead of showing up to the meeting, he just sent the women on his team.

And that was sort of it, but the way that it was conveyed was a little bit like he didn't have time for it. And anyways, it was just like the, it just like, It was weird, but it was still like, no, we should go forward. And then [00:25:00] basically like, I just like missed, all the things that I was supposed to do and fill out, which is terrible, but it was , like family So it passed by and I just was like, I never responded to the email that said, yes, I'm in, like, I got sent all the docs.

They weren't in my name, but I got sent the docs and I was supposed to reply with like, yes, this amount. But I never did that. So it passed me by. Anyways, that has been a really difficult investment, and I'm like, oh, I feel like , had I had the patience, had I listened to myself better and just been like, wait, hold on, are you sure, I would have made a better decision.

I accidentally made a good decision. And so I think it's like patience plus listening to yourself. And like if something's off, like it's probably just off and it might just be off for you. Like it might be on for somebody else and that's fine. But just listening to that, I think is really important. I think. The other half answer that I'm going to give you is more about a mistake that we made in Backbone and [00:26:00] how we organized ourselves.

And I think one of the mistakes that we made was, and this is

not realizing that we needed to talk about money earlier.

So when you're friends with people, even if you work with them, talking about money, and because this is angel investing, this is your personal money. Can be kind of weird sometimes.

And so we waited way too long to have very honest conversations about literal amounts of money. And what that did was it created this like imbalance in terms of how people were participating and then how that was either perceived or how we navigated that.

We always operate in super high trust, but it was like almost the zone that we can to. And to the point that it was like, okay, [00:27:00] wait, there's some people who clearly want to invest a lot of money and some people who don't, some people who can put in a lot of time, a lot, some people who can't and so , it wasn't bad, but it got to a point where we were like, okay, wait, I think we need to talk about money.

And luckily two of our partners Marcy and Brett just did a really good job of just doing that really gracefully. And in a way that made us, All feel super confident, no matter what your answer was, how you wanted to participate. And I think it was just a conversation that just should have happened way earlier, but now that it is, it's like, ugh, so much better

Shaherose: I love that, that's such a good lesson for people who are thinking.

about creating an investing angel collective that , angel investing isn't just about money, it's also about time and getting clear on, People's sort of comfort level with offering both, or just one, and the levels within it. And so I love that as a [00:28:00] lesson for those of you thinking about starting an angel collective.

And on the first point where you kind of, missed the investment, oops I actually think that's a wonderful lesson for people to pay attention to because I've learned over time that if I meet a team and learn about a company and I not pulled towards it. And really like finding myself wanting to know more or following up really quickly, like those sort of like unconscious behaviors are actually unconscious insights.

And because, people like you and I, we've been in the industry for more than a decade, actually close to 20 years now working. We've learned so much that it's in our bodies in a way that. We need to access. And so what we've talked about in other episodes is, investors need to have independent thinking.

And that's what you're talking about is at the end of the day, like, am I tapping into myself? You're calling it patience, but am I tapping into myself and listening to the subconscious behaviors that I'm [00:29:00] doing that are truly like unconscious insights? About the deal.

So I think, there's so much wisdom in that and we forget that, we might be objectively analyzing things with a spreadsheet, but really a good portion of investing, whether it's an angel or a VC does come from within.

And it's, also known as intuition.

Atlee Clark: Yeah.

The art of feeling a "no"
---

Atlee Clark: And I think especially if you're investing with other people, we have become very okay with someone being like, you know what? and that being the okay answer, because sometimes people want you to have this really analytical or insightful reason why you're saying no. and sometimes you're just like, it's just not for me. There's some VCs that I know who write the most amazing rejection emails I've ever seen Angela and Boris at version one ventures.

I have seen some of them and they're so good. They spend so much time being really clear about their "no". And I think as a [00:30:00] vC, can be an important thing to do. As an angel, , it's okay if it just doesn't feel right. And it doesn't make you or the company bad or good. It's just, it is. And the best thing you can do is be like, you know what? This is not the right time for me. This is not the right company for me and move on to the next one.

Shaherose: Oh, I think you're hopefully releasing. Some pressure that angels might feel, cause we all acknowledge that plenty of you are doing this on the side. And so to have the time to truly deeply reflect, you might not have it. And I think to your point, the best thing you're going to do with the founders, just be quick and let them know. And your reason for no is. Good enough by saying this isn't for me. So I love that.

Atlee Clark: It's the kindest thing you can do too, because like they're spending time, and for a founder, there's nothing more valuable.

Shaherose: Yeah. There's nothing more valuable than time. Agreed.

Best Investment: Highlighting Top Performers Calico and MIrza
---

Shaherose: Let's talk about some rosy stories or a rosy story. Let's talk about your best [00:31:00] investment so far. Ideally, one that has been realized and give us some concreteness. What's the company? How long did things take? What were the multiples? Tell us about.

The investment you're most proud of.

Atlee Clark: So I don't have any realized investments yet. Like I'm hoping, okay, but the one thing I will say, my entire portfolio is still alive. There's been a couple of bridge rounds, but like we're there. And so that's good. And a couple of them have had

some really solid rounds.

I think like I started investing in 2021, which if anybody listening to this is like, well, that was bad timing.

I'm like, yeah, agreed.

The last three years have been so weird. And I think there's some founders that just made some really good calls. Like there's one that I think about, it was Kathleen Chan.

It's a company called Calico. And they're in the manufacturing space. Basically they create a bridge between small businesses and manufacturers. And as a small business I was like, yes, [00:32:00] like, tell me more about this. This is so interesting. And she's taken a different, a couple of different angles.

But when I invest in that company, her and I had this conversation and she's like, you know what? I have 19 months of runway and she's like, I'm kind of getting pressure that's too much runway, but this was like, right. Like it was, things were still good at this time. And like, man, in hindsight, what a brilliant, like, and she said in that call, she was like, getting some pressure that I'm like, not burning fast enough.

She's like, this is right for me and my company. And that's what you got to do. You are the founder and cEO here. And if you think that's the right thing to do right now, then like, you need to do that. And she did. And right now we look back on that and it was like the smartest thing she could have done. And she has this amazing growing business and so, I'm proud of the resilience of some of these portfolio companies through this time .

Resilience in Founders: Overcoming Challenges
---

Atlee Clark: I think of [00:33:00] another company I invested in mirza and the founder over there is Siran, she's amazing. And they provide employer funded childcare to help close the employment gap for women and caregivers , in the workplace.

And they sell into like large companies that have huge workforces. She had all this traction. And then everybody's like, Oh, no, it's a different time. And I'm not sure that this is the right thing, but her and her co founder just made really good decisions and invested in relationships with the right people at really big Fortune 500 companies and just stayed really focused during that time. They didn't freak out.

And I think that resilience is the thing that; will it lead to the ultimate return? I have no idea, but it's all about like when the chips are down, right? Like how do founders react when the chips are down? How do investors act when the chips are down?

But I just have like faith in them.

Shaherose: I love [00:34:00] that. I mean, that's all we can have because the startup journey is full of uncertainty. And so having faith in these founders gives you the sense that, Hey, I'm really excited for them. And and with that let's talk a bit about like today.

Current Investment Strategy: Today's Focus
---

Shaherose: Here we are at Shopify running the show and talent, new role to some degree. You also are running a startup on the side, but you're still investing.

So maybe let's just like talk a bit about today, like what are your check sizes? How many deals per year? You did reference to the areas you're excited about. Are there any others? Just sort of for founders to know what to come to you for and what to expect if they want to invest with you and Backbone.

Backbone.

Atlee Clark: Yeah. Okay. So I'll start with Backbone and then it'll lead to me. So at Backbone, we do invest as individuals, but we look at deals as a group. We have done a couple sPVs, but like, it ended up being way more paperwork than it was worth.

And [00:35:00] so, when a deal comes in to one of us we evaluate it and we share it with the group. And then we get thumbs up, thumbs down on anyone who wants to do a call. Our deal is like, you only do one call with us. We don't like we're angel investors.

We want to make this easy and quick while still giving this space and time to fully understand what you're doing and giving you the chance to talk about what the opportunity is.

But not having to do individual calls with all of us.

So, the person who brings it in gets like thumbs up, thumbs down from everyone. If there's a couple of thumbs up, then go and do a call.

And then after that call, it's like, okay, does anybody want in any follow up, whatever. and then we write checks individually.

For me, I write checks usually somewhere between 10 to 20 thousand dollars. I like being in early. I typically am like just a first round check. I have done two follow ons. But those were sort of [00:36:00] in really specific circumstances.

For me, it's like, friends and family round, early seed round just being that first, like "get it off the ground" kind of check.

Shaherose: Is there a valuation band that you prefer?

Atlee Clark: No. I just, this is where it's a true angel round. I'm like, yeah, let's kind of talk about it. But it also is like internet math. I don't know. I just like, I'm like, yeah, we could go on Reddit and figure it out.

But like, hey, do you have a great idea? Do I want to see this thing in the world? Do I think you have an above average chance of doing it? Then I'll give you like $10, 000 to pay for an engineer for a couple months.

Like, cool! Like, that's sort of how I think about it. Now, if we're talking about there are vCs involved and like it's a real seed round, well, then it's a little bit different, but like I'm this like, typically one of the smaller checks on the cap table. So you've got to like decide what you're going to fight for. And I love seeing a discount. It's always nice just in case I [00:37:00] like decide that I want to, you know, so it's a little bit more that like basic entry.

In a given year, I'll do somewhere between two and four, depending on what comes across my desk. And I also like to keep the size of the portfolio manageable because I love investor emails. I read them. That is the fun part for me. The company building part is the fun part for me. And that's what I feel like is my price of admission is like to write you a check. Then I get to know on a, I don't know, monthly or bi monthly basis, like what's going on. And that's the fun part. And I don't want to get to a point where I'm like, oh, wait, I have no idea what's happening. There's too many. So it's also about just like how big that is overall.

Shaherose: So to date, how many active investments in your portfolio?

Atlee Clark: Oh, I was supposed to count before we talked. I think 10,

Shaherose: Great. . And

For a founder to have someone like you with both the scaling of startup experience, but also sort of [00:38:00] that trusted advisor experience that you and I uniquely have is truly special. And so again, to the founders listening, you'd be lucky to have atlee on your cap table.

Couple more questions. So you're no longer here in the Bay. You and I are not going to dinner at Dosa, rest in peace uh, and running into founders, right? Like we were in the mix and you're not here anymore.

Sourcing Deals: Networking and Connections
---

Shaherose: So tell me about how you're sourcing your deals right now.

Atlee Clark: So, I think the canadian tech and startup landscape is like a very interesting thing.

And it's relatively small because there's only so many VCs, so many angels, so many founders. But the Bay Area isn't that big either. Like everybody also knows each other. , so a lot of it comes through like direct connections. and to be clear, most of my companies are actually U. S. based companies, not Canadian companies. But I love investing in Canadian companies too.

So on the canadian front, usually it comes [00:39:00] through a network. There's like a big shopify angel, like signal. I probably shouldn't say that, but that's true.

And so we share deals there all the time. , and just people that I know in

the Canadian tech scene.

It's also interesting, and you probably get this too, I have a lot of friends aren't in tech and within their networks, they're like, Oh yeah, my friend is building an app. They should talk to you. Sometimes that's good. Sometimes that's really bad.

Um, it, It depends, but I've had some surprises come through there.

The last check I wrote, which I'm super stoked about, is actually a former Shopify colleague.

I actually hired her into shopify and then she left because she's had this like itch for a long time. had a startup before she joined Shopify.

Anyway, she's like, I just got to go back and do it again. And she was one of those people. I was like, literally, you could do anything and I'll write you a check.

And so, that's happening more and more. But the best ones are always for people you know. And when you send me [00:40:00] an email and you're like, Do you want in?

And I'm like, yeah.

And then I still remember that last one.

I was like, yes, I'm in. And I was like, I'm in for 15, 000. And you're like, there's three left. And I was like, I'll take it.

Shaherose: Yes. I remember that. I remember that. And that company is doing really well.

Atlee Clark: So, so

well.

Shaherose: Let's talk about it. Zum, a female founded company that is on fire and so excited that she wanted to diversify her cap table. And we got a tremendous amount of incredible angels, you included in their mostly recent round and they're just, blowing it out of the water.

Yeah.

Atlee Clark: They're animals.

Shaherose: Yeah, yeah so Zum provides sort of tech enabled electric vehicles for transportation of kids to and from school and other afterschool programs. And by the way, that founder started her company after attending one of the first Women 2. 0 events that we hosted at Stanford, left the conference and said, I need to start a company.

Atlee Clark: Stop! I didn't know [00:41:00] that part!

Yeah. Oh my gosh. That's so cool.

Shaherose: Yeah, we're thrilled , to be on her ride and actually this brings up that investment we did together, through an SPV was a series C

I felt very fancy

Atlee Clark: investing in a

C round, even though it's only 3,000 dollars.

Shaherose: Right. No. no. So let's talk about that, right? So here you are, angel investor, usually putting money in pre seed and seed. And I present you with a deal at a much later stage and valuation

How do you think about that as an angel investor? Is that something you believe in doing, want to do more of, don't believe in doing as a philosophy, like where do you stand on angel investors coming in much later stage?

Atlee Clark: I'm not sure if I have a philosophy about it. I think the philosophy is still rooted in like supporting great founders, investing with your community, which

like you are part of mine. And so

I

was like, no, I really

want to do something. And you would send me other things that I had passed on.

And so, cause I learned how to be [00:42:00] patient. Look at me growing. Um, but then I saw something and I was like,

why do I

keep thinking about this?

And then I was like, Whatever, it's an opportunity and it

checks other boxes

and I probably

wouldn't seek it out in

and of itself, but I wouldn't ever say no to it again,

either.

Shaherose: what you're sharing here is truly being driven by intuition feeling really like, how do I feel about this deal? Because I want to see things in the world, like you said, and this was something you wanted to see in the world.

Okay.

other than doing more investments, so besides reps, how do you get better at investing?

Atlee Clark: I think the best thing you can do is talk to other investors. And I say that over Founders because I do really believe in.

Respecting and protecting founder time. And I think if you're an investor you're if you're not serious about someone's company

and investing in them, then it's like you waste their time working on their thing.

So I avoid that if it's completely selfish. If I can [00:43:00] offer them something like great, cool, but otherwise talk to other investors, not necessarily because you're going to learn to invest better. But every single time I talk to an investor, I learn a different way that people look at investing.

And I think it's good to remember that everyone has a little bit of a different take on it.

And my own take is just as valid as anybody else's. it gives me the confidence to say no as much as it does to say yes.

Shaherose: Yes. At the end of the day, it's the independent thinking that's really important, both as an angel and a VC, because ultimately that'll lead to you realizing alpha in your own personal way.

Okay. So,

let's say as an angel investor in 10 years, Atlee Clark is on the Midas list. What got you there?

Atlee Clark: I don't know if I want to be. don't

foresee I invest in things that I think are going to make money, to be very clear.

I also know that it [00:44:00] probably won't. And I have to be okay with that when I write the

check, but I don't just like invest in something because like it feels good. I invest in because it feels good, and I think it's gonna make money.

Um, but I don't foresee me changing that into like being a full time Angel investor. I think that that would take the joy out of it a little bit. being a VC would be something different, but like, that's not where I'm at right now. And so that, that's a little bit different. So I just don't know if it's like, I don't know if it's an aspiration.

So it's hard to be like, Oh, what got me there? And I'd be like, I made a mistake. I'm not sure.

Shaherose: I think again, you're highlighting that for angel investors, this is something we're doing for other reasons. it's the other reasons for which you Become an angel investor. And you're reinforcing that.

Okay.

Lightning Round ⚡
---

Shaherose: Speed round.

Atlee Clark: Okay.

Shaherose: You ready?

Atlee Clark: I think so.

Shaherose: Who is another first funder you admire?

Atlee Clark: uh, my other,

Backbone partners, obviously. And Charles Hudson

Shaherose: it. I love it. [00:45:00] He's also invested in a lot of Canadians and has. Spent the time to get to know the ecosystem. And so let's give a shout out to Charles for that.

What is a book or piece of media that has had a major impact on how you're investing today?

Atlee Clark: Um, How I Built This by Guy Raz . RIP.

Cause they stopped making them in like 2022. But I'm like a big Guy Raz fan. If you're a parent and your kid's into science, Wow in the World is the best podcast of all time that features Guy Raz. And so I still have Guy Raz in my life, which makes me feel better . But what I loved about that podcast, and I go back to it sometimes, is the way he asks questions.

Sorry, this is not a speed answer, but I wanted to tell you a little bit. Okay. So he has this phenomenal way of Speaking plainly and asking questions that you're dying to ask, but you're afraid that you're going to sound stupid if you ask them. But he just asks them in this like, really like kid-like curiosity,

and I try to take the way he does [00:46:00] interviews into the way that I talk to Founders, because we can just be like, Hey, I don't have to know anything about this. And I can just be curious and open. And if I don't understand it, like be like, wait, what? , I think that is better for you and it produces just like a better conversation with a founder.

Shaherose: Oh

my gosh, you are so right about that because people sometimes think that as an investor, you have to come to a meeting and know everything about the space or the company, and that is just not possible, nor is it necessary, nor is it true, and so actually coming in and. Learning from the founder, being curious is good for everyone because ultimately they're going to operate from what they know anyway.

And so what you know matters less.

Atlee Clark: Yeah, exactly. And you're not running the company. You're not starting the company. So don't hold yourself to some crazy standard that you have to know it. And also like, if people are using jargon that is in their area, , it's okay to be like, wait. What are you talking [00:47:00] about and explain that to me .

Shaherose: Oh my gosh. Totally. you know, we started investing in digital health and some companies selling into payers and I really had to pause and ask the founders, like, what is this jargon you speak of with health insurance?

So, okay. Um, Zoom, phone or in person meetings.

Atlee Clark: In person, I will say the silver lining of all the COVIDs, is like, I Zoom with a lot more people that I don't get to see. And it's cool to just be like, yo, let's just hop on and you get to see a person. I'm a body language person.

And so I still really like it.

Shaherose: I love that. Social media platform of choice.

Atlee Clark: mean, I'm an early millennial, obviously Instagram.

Shaherose: Great, I love that. Early millennial. I'm an elder millennial.

Atlee Clark: What's the difference between early and elder? I would be an elder millennial.

Shaherose: I think we're the same age.

I think so. I think we're elder

millennials.

Atlee Clark: Oh, is it elder? See, I'm not even cool enough to know the term.

Shaherose: . Oh my gosh. Thank you for joining us. Atlee Clark. Where can people find [00:48:00] you online?

Atlee Clark: Um, they can find me on, , what X I guess we call it now. , Atlee Clark and, , that's the best place to find me. LinkedIn sort of sometimes.

Shaherose: Before we hang up,

I would love for people to know about your second side side hustle, your startup.

Atlee Clark: I know, so I always say that I don't invest in DTC, but I actually have invested the most in DTC because I've invested so much money in my own company, Pika, which makes, kids and baby pajamas and sleepers all out of super, super soft, bamboo.

So, I started it in 2018 with my best friend and her sister. I always say , they tricked me doing it. And it's the best trick I've ever been tricked into. And it's so fun. , it scratches a different itch. I get to use Shopify every day. So I'm like , the worst, cause I like just go into people's Slacks.

I'm like, hello, checkout team. I have a question. And they're like, Okay. it's gotten [00:49:00] me really close to our product. And so I think it makes me a better employee at Shopify, and it's just cool to build things with your friends.

And it's cool to build non tech, I gotta be honest, the amount I've learned about fabric and sewing and the manufacturing industry is wild, and it's just fun,

Shaherose: Thank you. This was so fun.

that was such a great interview with a dear friend and fellow Canadian. , and I'd love to share some takeaways from the convo and these takeaways are coming with my angel hat on. Because angel investing is how I've gotten started. And I still do outside of my day job.

Shaherose: One of the first takeaways was. Tapping, into your intuition. We've heard this time and time again. And the way Atlee articulated it was how her actions or kind of speaking louder. Then her mind, meaning she just [00:50:00] happened to not take the action to make an investment. And sometimes we have to acknowledge that. An action is louder than a thought. And we do things unconsciously. And that's information. And as an angel. When you're busy, you have a day job. Or you have other commitments and this is not your full-time job. Taking the time to acknowledge that you have years of experience that are speaking to you in other ways. And simply listening to that. Is the answer.

It doesn't always have to be a well thought out, no, with a long email of why you don't believe or want to invest For you, it could be a no, and that is okay. And so I think it's important that the reason for no doesn't matter. This is your side hustle. Follow your intuition.

Another takeaway it's a great one to remember is just be patient. And I wanted to build on that thought. More [00:51:00] recently, , I acknowledged that I hadn't seen a deal that I wanted to move on in a month or two. And I started to feel bad. That I hadn't made an investment. And when speaking with that, Atlee, I was reminded of something called it's not well-named.

It's called the secretary problem. Which helps you make decisions The theory is that if you've seen one third of the best possible options, once you think the next one you see is better than the first third. It's time to make a decision.

I need to ask the question, is this the best deal that I've seen in some amount of time, which is sort of speaking to that secretary problem thinking. Is this the best deal I've seen in the last one, two or three weeks months, or whatever timeframe makes sense. , because if not, you know, stay patient.

Another takeaway. Especially for angel investors was highlighted again. We saw this with, uh, Rachel, we saw this with [00:52:00] Eric. That everyone, as an angel, who's investing their personal money. Is really doing it from their own personal reasons. , Rachel talked about being supportive to founders. That's what she cared about.

Most was community. , Eric talked about learning, And for Atlee she was very clear. No, I'm not trying to learn. I want to invest in founders, in companies that I want to see in the world in areas that I understand.

And I live in. And that's it. I'm not trying to learn. And so everybody's reasons are different. And I think as an angel investor, Really tapping into what is unique for you? And why you want to invest is super important. And the reason I believe that's important. Is because it creates focus of. Where in the world, can you invest?

You know, if you don't have a focus. Anything is possible in terms of potentially investing. And so this idea of your own thesis and thesis in this case can be anything, right? It can be. Founders. I know it could be immigrant founders. [00:53:00] It could be spaces you've worked in.

Just having a belief about things that you want to invest in. Drives focus and it reminds me of what Eric had said like, Be known for something. So first defining why you want to own best. And then become known for that so that you attract the kind of deal flow you want to invest in.

And I think. Being a generalist angel. Yes. On average could be great, but you don't have to do a lot of deals. And it's a lot of decision fatigue. Is this the best? AI. Video editing tool that I've seen. What unique advantage do you have in assessing those types of deals or what unique help can you provide?

having some sort of focus or thesis as an angel will just really help both with deciding quickly if this is a yes or no meaning. Yes. I even want to dig into it. Or no, this is not. What I want to focus on. And two it'll help with the deal flow, flywheel of deals [00:54:00] coming to you. That either matter to you or you can uniquely support.

For me, I would say. In the beginning, my thesis was around investing in founders. I knew because I felt like I had asymmetrical information. On them. And I had seen them over the years. And so I said, I'm just going to invest in founders. I know. And then I brought in that. As I started doing more investing to spaces.

I knew. So while I was investing at Nike, I looked into areas in wellness, sustainability, and commerce. I am in similar themes today through cake. And I find that just having that focus is really great for me so that I can just quickly say, yeah, no, I'm not going to invest in the AI editing tool for video.

And so it allows me to say no to deals. So that I can keep focusing and building expertise in the areas that I want to invest in

another takeaway. So for angels, especially when getting started. This idea of being in [00:55:00] community. I love how Atlee talked about the founding of Backbone, you know, it was senior women at Shopify coming together. And realizing, Hey, we already invest.

We already advise. Let's do it in community. Let's help each others portfolio companies. Let's source collectively, but let's decide independently. And I've done that. So I wanted, I might've shared this in other podcasts, but after I wrote my first initial checks, I joined a friend of mine, Sandeep Ahuja. who has an active angel list syndicate. And he had myself and five other founder operator types come together.

And what we did was we sourced, and evaluated deals together in community, helped each other out, but we decided independently on the deals we wanted to invest in. And I just found. That it accelerated my learning, like Atlee said, it allows you to see how other people think and that you don't have to adopt it.

It just gives you the permission. To develop your own [00:56:00] independent thinking. Cause everyone is seeing a deal differently based on their life experiences. and just accelerates learning about not just deals, but the process of investing, standards and valuations or, things that are so nuanced that you can only learn by doing.

And then when other people do them, they share a learning with you. So highly recommend the idea of building community of angels coming together as a collective. If you work at a company or your friends that want to come together and look at deals. You know, it's just something that I think more people need to do.

And there's someone we know Brian Nichols, who does this at angel squad, and he's done this for. His previous company, Lyft, where he brought, , Lyft operators together to invest in, , companies that were founded by Lyft, alumni and the broader ecosystem. I believe that there's so much power in building micro ecosystems. That help [00:57:00] investors in their journey and equally help the founders in their journey.

we talked about it, shortcuts, access to talent, to money, to learnings.The last takeaway is reminder to stay curious that you don't have to know at all, especially when to give that permission to angels who do this on the side. I think in my first investments. I felt like I had to do. Gobs and gobs of research to determine if I really wanted to invest. When really it was all about for me, the founder, I knew the founder and that was my thesis at the time.

Right. The first few checks, my thesis was invest in people you know, and see where that goes. And I found myself going down rabbit holes, and I didn't have time for that. And realized, I'm going to learn from the founder. So flipping the tables and staying curious and learning from them. Is a mindset.

I'm not saying you don't do your research. I say. Really just stay curious and allow the founders. Vision and perspectives to also inform if you want to invest, because when you stay curious, you learn how other people think. [00:58:00] And that's what you want. ? You can do all the research, but ultimately how someone thinks and how someone acts is really what you're trying to assess and then determine if you believe that that will lead to an outsized outcome.

, I hope this was helpful. Would love your feedback. Would love to hear from you. That's all for now.