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Note: This is an original transcript–edited for sense, length, and clarity.  If you have any questions or concerns, please email our host, Doria Lavagnino, at doria@sheventurespodcast.com.

Intro:

Doria Lavagnino: Named one of Inc. magazine’s top 100 female founders to watch, this woman is well-versed in the pivots required for an early-stage company to morph into a viable, scalable business. 

A 15-year startup veteran, she understood earlier than most the rapid evolution of digital apps and e-commerce and started in this more than a decade ago. She helped grow Canada’s Plastic Mobile, an award-winning mobile app agency, to acquisition in 2015. 

In 2019, she soft-launched ShopThing, one of North America’s first live video commerce apps, which quickly amassed hundreds of thousands — maybe there are even millions now, I don’t know we’re going to ask) — of followers. She is also one of the 2.3 percent of women who have successfully raised venture capital. She closed a $10 million round in 2022. Maggie Adhami-Boynton, welcome to SheVentures.

Maggie: Thank you. Doria, thank you for having me.

Early Career

Doria: It is really exciting to have someone who has achieved so much in a short period of time. I wanted to start — rather than go through your entire career — with technology. Much of your career has been spent in technology, and what I was curious about was: Did you always know that you wanted to focus there, or was it an evolution or a bit of luck? 

Maggie: Such an excellent question. So, I actually spent my entire career in technology, and I absolutely did not plan for that. My undergrad is in psychology. I always thought I’d be a clinician of sorts. Coming out of my undergrad, I realized that I didn’t want to do another 10 to 12 years of schooling, so I decided to apply for a master’s program in business. 

I got in, but it was a part-time program. While I was doing that, my brother-in-law said, “Come work for me at this branding agency on the digital side. See if you like it.” And I was always an early adopter of technology. I was in the very early days of e-commerce. I won’t tell you how long ago because it’s going to age me, but when eBay first came out, I had an eBay store. And so, always an early adopter of technology. Loved, you know, school never taught us that that was a vocation, especially back then.

I mean, I know they’re doing a very good job of it now because it’s a force to be reckoned with. But back then, technology was not an option. So I accidentally landed in this role as a project coordinator on the digital side, managing websites and such, and was obsessed. I loved it. I couldn’t ever imagine leaving tech. 

That’s where my career started. I continued to go down that path in the project world: on the operations side of building websites and what have you, and then once the App Store (actually, even before the App Store) began, my sister and brother-in-law started a mobile service agency. And I kind of saw that as a way of the future and decided to join them early and built an incredible business out of it.

Doria: So it was a combination of all of the factors, it sounds like. I know that you were a part of the executive team, you’re very modest, and you spoke about your early role, but then you were VP of operations, and that’s the role that I believe you were in when Plastic Mobile was acquired by Havas. 

And so what I wondered is if you could tell entrepreneurs who are listening, who are starting to scale, what are three things that you think you did particularly well to grow the company?

Maggie: It’s a lot of learning. I didn’t come into Plastic as a VP. I came in as a director, really understood the project process very well, worked from the ground up, and built a team. And then it was a lot of learning, talking to friends, networking, and figuring out how you scale a company. We grew pretty quickly. We were doubling year over year the entire executive team because again, all of us were pretty young at the time. We all had to very quickly learn how to scale and how to grow. And I think the advice I would give to other entrepreneurs is to talk to as many people as humanly possible. Not only will you learn from their learnings, but you’ll also learn from their failures of what not to do so much.

Doria: Almost more right. From the failures rather than the wins.

Maggie: Definitely more. Yeah.

Doria: And you also went to Harvard at some point. I don’t know where that was in all of this. I assume before it was in the midst.

Maggie: So schooling does help. I will also say that schooling does help if you’re able to do it. But I did take a small sabbatical from Plastic; take that lightly because I was still working.

Doria: Right.

Maggie: I did take a little bit of a leave to pursue my master’s.

Doria: Harvard, and it’s in management. So, I assume that also gave you at least some academic and probably real-life training in how to manage growth and scale.

Maggie: Exactly. And I will say this: As incredible as university degrees are, they become so much more impactful when they’re contextual. So having already been working, having been in the field, having been a business professional, that degree was so useful to me in ways that I don’t think it would have been had I taken a bachelor of economics prior to ever having any work experience.

Doria: I completely agree with you on that, and I think that that is one of the challenges that people who don’t take internships or work at all during college, if they are so lucky or not, I don’t know if it’s a good thing, really do struggle because they have no real-life context for what they’re doing.

Launching ShopThing

What inspired you to pivot? I know that there was the acquisition, and then you pivoted from mobile app development and the agency to your live video commerce with the creation of ShopThing. How did that come about?

Maggie: Not as organically as you would assume. I was definitely always searching for a way to marry my passion. So, my passion is style/fashion/retail, with my vocation in technology. And so I had thought about many ideas in the past but never really had the guts to try them. And when I was in Harvard, as a part of a social media course, I had to create an online brand. And so, I created this online brand that came along with an Instagram handle and a blog. And that was just for the course. Did really well because I loved it. And my professor gave me really good advice. She said, do not pick an industry just because you work in it. Pick something that you’re passionate about because then you’re going to want to blog about it and you’re going to want to grow that handle and you’re going to ultimately end up with a better grade.

And so instead of picking something in mobile tech, which I would have at the time, I was like, okay, well, I’ll pick a fashion blog. I loved it so much that years after I was at Harvard, I kept that page and that handle and all of that fun stuff. And so, at this point, I had amassed about 13,000 followers. I would go to influencer events when I could on evenings and weekends and whatnot as a part of that community. I came across this woman in New York. She would scour the streets of Manhattan. She’d walk into sample sales and outlet malls and what have you, and she would shop for her Instagram followers. And so I came across this page, and I was obsessed with it because who doesn’t want to be shopping in New York when you’re not in New York? 

Long story short, I tried to buy something, but it did not work out because I’m Canadian, I didn’t have Venmo, and all this fun stuff. But my tech brain and my operational brain immediately thought this was an incredible concept, but it’s not being done in the right way. There’s a way to systemize this and operationalize it. And so, once I started thinking about that, I started doing a ton of research and landed in Asia. Not physically, but digitally landed in Asia, where live shopping was a massive — and still continues to be a massive — industry. At the time, it was only $18 billion. 

Today, it’s well over $500 billion. So, obviously, the growth has been monumental. Yes, but I landed there. I spent an embarrassing amount of time watching these Asian influencers sell everything from pancakes to banana holders to cars to houses to everything, literally everything. And I was really enamored by this concept. Did a bunch of research. Nothing existed in North America. And so I saw that as my opportunity to finally marry my passion for fashion, style, and retail with technology.

Doria: Right. You chose a soft-launch. Why was that?

Maggie: I think for me it was really about the product, market, fit, and trying to find that actually, even before I soft-launched it, I spent eight months piloting it while I still had my [job]. You know what that meant: On the weekend, two days a month, I would go to an outlet mall, and I would do exactly what that girl in New York did. I would stream to my Instagram followers and sell things and then package them up at home and ship them out. I really wanted to know if there was demand. And then one day, I was like, okay, let me put an Instagram ad on it. 

So then I put an Instagram ad on one of my posts and brought in some new followers and brought in brand-new customers. And once I felt comfortable with the fact that there is demand and people do like what I’m doing, then it was really about, okay, let’s leave the job. Let’s assemble a team, and then let’s soft-launch this to see if we can really get to product market fit before we scale it.

Doria: What I’m hearing you say, which I think a lot of entrepreneurs who are new don’t necessarily do, is they don’t think about product market fit — or it’s kind of an afterthought to their big idea. And then when they try to implement it, they find that it either doesn’t work or there isn’t demand. And so that’s admirable. And do you think that that came from Harvard? Did it come from working before at Plastic Mobile? Where do you think that came from?

Maggie: Very good question. It was actually a combination of both. So, obviously, having had the experience at Plastic building apps for these massive companies, helping them scale, helping them roll out, I had a lot of experience with not exactly product market fit because these were really big companies, but a lot of experience with rolling out a brand-new product into the market and watching adoption, watching people use it, taking that feedback, iterating on it, and continuously releasing. 

Then, you know, the entrepreneurial side definitely came from Harvard. I took a bunch of really great courses on entrepreneurship, and that’s one of the things that you talk about. And I’ll tell you, at the time when I was doing it, I didn’t exactly think in my head, “Oh, I’m trying to assess product market fit.” It was just based on my experience. I knew that in order for this to be a viable business, I had to prove that people wanted it and there was demand. 

Later on, of course, I knew that that was a product market fit. But then I wasn’t thinking, “I need product market fit.” I was just thinking, “I need people to want this, and I need there to be demand.” I need to know if this is a viable business before I quit my VP job. I have a family, and I have kids and all that fun stuff. And so, for me, it was really I needed to make sure that there was something here before I threw everything out the window.

Doria: So two questions there. At what point were you sure? Like, what were the numbers or the metrics that you needed to see to feel comfortable to leave your job?

Maggie: I was never really sure if I was going to be honest with you. I wasn’t selling enough. I was selling three, four, five things when I would go on these trips, which to me was enough. If every time I could sell one more item, then I felt that was enough with my very limited audience with almost no money behind it. But I really believed in it. I had a strong passion for it. I believed in it. I felt like I understood enough about the content creator space, the fashion space, and the style space, and I understood enough about the product space on the tech side for this to be a viable business. And I was just like, you know what, there were all these other ideas that I was too scared to execute when I was much younger, and I didn’t have the experience necessarily, and I just really wanted to do it.

Entrepreneur Challenges

Doria: I’ve heard you a couple of times now say that you felt fear not only with this one but also other things that you had thought of in the past. And you mentioned that you are a wife and a mom, so you had extra responsibilities. And so how does an entrepreneur and, I know there’s no right answer to this, but I’ve heard so many different stories of people who just jump in, and they’re like, you know what, I’m going to make it work. I’m going to see if it works. And it might not. And that’s it. And then I hear people like you, you’re more steady and logical about what you’re doing. Are you happy with how you approached everything? And do you have any tips for people listening?

Maggie: Yeah, I’m really happy. Obviously, the outcome has been incredible. I’m obviously very happy with how things turned out. I will say the regrets I have in my life are not having done this earlier. So, not having taken the ideas that I had, and they were all really style and tech combined, I would have done this 10 years ago if I could have, but I was really scared. I will tell you, the resources also didn’t exist back then that they do now in terms of incubators, and venture capital wasn’t really this massive thing that it is today. And so I didn’t really feel like I had a community behind me.

Whereas today, if you’re a young entrepreneur, there’s a community, there are incubators, there are a lot of resources, there’s government funding, there are a lot of things that you can take advantage of to help alleviate some of those burdens. Also, I have a family now. When I quit, I had three kids, a husband, and a job, and I had to think about that. That’s a lot. 

When I was younger, I could have lived at home, taken two years of my life, and risked everything a little bit earlier. I had to be a little more systematic and planned when I did this. But honestly, even when I left, I thought to myself, when I quit my job and I decided to do this, I thought to myself, what is the worst that can happen? The worst that can happen is I take one year of my own salary and invest in myself, or two years or whatever that is. 

For us, it was one year. If we didn’t get to something at one year, then we were like, okay, maybe this is not it. But I take one year, I invest my own salary, and then if it doesn’t work out, I go get another job in technology. It’s not the biggest deal in the world. We sat down as a family and had a conversation about it. My husband felt comfortable, and so it kind of made sense.

Doria: I love that you spoke about it, you thought about it, and you also had a cut-off point. So actually, my 18-year-old daughter has been teaching me about the sunk cost fallacy. And so it sounds like you gave that a lot of thought as well. 

And I don’t want to not ask you, what exactly is  ShopThing? So our audience knows.

Maggie: We are a live shopping marketplace. We pair influencers and content creators with brands to host these incredibly engaging live shopping events. So the closest thing to our model would be QVC, but it would be online. It’s done on mobile and in a really engaging new way. We use short video clips. So think TikTok. We sometimes call ourselves the TikTok of live shopping versus that traditional two- to five-hour live format. But really, the secret sauce for us is using the content creators and allowing them to curate these incredible collections for our audience.

Staying the Course in Entrepreneurship

Doria: Can anyone be a content creator on your platform?

Maggie: Absolutely. Yeah. You can apply. Right. Today, we are hand-selecting and carefully curating it, but you can definitely apply via our website. And in the future, really, the plan is to roll that out and allow anybody to be able to shop.

Doria: What would you say is the biggest challenge that you faced when you were launching ShopThing before the funding came in, and how did you overcome it?

Maggie: That’s a very good specification because I would have said fundraising.

Doria: We’ll get to that. 

Maggie: I think the biggest challenge for me in the early days was staying the course. 

You have this vision in mind. First of all, entrepreneurs are not the most patient people because we dream these things, and we want them to happen now. But nothing in life happens now. You’re constrained by capital, you’re constrained by resources, you’re constrained by a lot of things, many things. But when it doesn’t happen fast enough, or if you hit a little bit of a speed bump, it’s staying the course and not thinking that every speed bump needs a pivot.

I think that was a really important thing that I learned, especially during COVID. So, when March 2020 happened, our business was initially built off of going into a retail store. It’s a little bit different now because we have these incredible partnerships, and we do things in the studio and stuff like that. But in the early days, it was just in retail stores. And so when March 2020 happened, we were hit pretty hard in Toronto. We were closed down for the better part of almost two years.

Doria: You had to pivot.

Maggie: I was like, we need to pivot. So in the early days when everything was closed for two months, we tried to figure out how to pivot. Let’s go B2B. 

We built out all these strategies, started having these conversations, and then the world kind of opened back up, stores opened back up, and our business exploded. And so, for me, it kind of made me realize that. And we had to throw away all that pivot work because it was not no longer necessary. We went right back into the store. But it kind of taught me this lesson of patience and really staying the course until there is a real viable reason for a pivot.

Doria: Stay the course. So, in other words, don’t pivot until.

Maggie: Don’t prematurely pivot your business because there are going to be so many times when things don’t go your way. And if every time something doesn’t go your way, you pivot,

Lessons Learned

Doria: So true. And this kind of brings me to the next question that I have, which is fundraising. You successfully raised $10 million. As I mentioned at the top of the show, 2.3 percent of women — and for women of color, it’s much lower — are successful in raising venture capital. Looking back, what did you do right?

Maggie: Oh, man. In the fundraising world, what did I do right? I did so many things wrong. I learned so much and gained a ton of experience. But we were a service business. We always made money. We were always profitable. We were not a fundraising business. And so even though we scaled and sold a company before this, fundraising was a whole other world. I learned very early on, after many, many conversations, you have to run fundraising like a process. It can’t just be willy-nilly where you tell all the investors I’m raising. 

You have to be really prepared. You have to understand. I should have talked probably to 100 more founders before I went into the fundraising world, which I did not do. I kind of did that after I got a bunch of nos where I was like, oh man, this is not going my way. But I think that’s probably what I did wrong. What I did right was learn. After every single meeting, we learned. We iterated on our deck. We figured out what investors were looking for. We learned how to pitch in a different way depending on the types of questions that were coming. 

We realized our story. If we got the same questions every time we were telling it in a certain way, that alluded to whatever that was. And so we learned just how to alter our pitch, to answer questions better, to be more prepared for these types of meetings. And luckily that led to a successful raise, which I know is very difficult for women.

Doria: How many VCs did you pitch to in total?

Maggie: So we ran a couple of informal fundraising rounds, and then we ran a formal one and then kind of got funded outside of that, not even when we were raising, which is a very interesting thing that happens. VCs love hearing, “I’m not raising,” by the way. I probably talked to somewhere between 50 and 70 venture caps.

Doria: Okay. To get to the $10 million?

Maggie: To get to, yeah, the one that really believed in our business and understood what we were doing. And obviously, the timing happened to be right as well. But yeah.

Doria: Do you think that your experience of having a previous exit mattered?

Maggie: Absolutely. I think that definitely mattered. I would say it matters a lot, but I also had 50 nos, so maybe it didn’t matter that much. I think there are a lot of other things that also mattered, and some of it was in our control, like the way we ran our fundraising process. Some of it, I would say, was kind of out of our control because it was also during COVID. It was very difficult to get a hold of VCs and get introduced to them. 

You cannot cold-call VCs or cold-email them. That’s a no-no. I don’t live in San Francisco, so I’m not part of that tech community. So, some of it was a little bit out of our control, but some of it is definitely fixable. If we had just had a few more conversations and a little bit more experience, I think we’d be more prepared going into Series B.

Doria: One other question that I have is what you were saying before about don’t change just because you get feedback. I have heard, and I have experienced myself, where VCs all have a different vision of what your vision should be. So how do you decide what to take and how do you decide what to leave? Because otherwise, you’re like forever re-creating, and then you almost lose faith in your vision.

Maggie: Right. Every single VC had a different vision for our business. Obviously, there are common themes, but all of them had their own opinions on where we wanted to go, how we should grow, how we should expand our business, and how we should evolve all these things. For us again, it was really stay the course. We had found something that was working really well. 

The year that we fundraised, the previous year, we had grown four and a half times in our business. And so we knew that we were being really successful at what we were doing. It was really wading through that feedback and picking the ones that made sense. Not necessarily pivots or changes to our business, but with this tiny little tweak, maybe I will be more efficient at doing this or with this piece of feedback. We understood the retail industry a little bit better because we were also not retail experts. But you have to very carefully weigh through the feedback because there’s a lot of it. And a lot of it is, frankly, opinion. 

You know your business better than they do. That’s also what I had to come to realize. It happened after maybe 20 meetings where I kept being like, oh my gosh, all these people have different opinions. And then I was like, you know what? I’m the expert. This is the business that I built. I understand it better than anybody else. Well, the co-founding team understands it better than anybody else. And so we can’t be so easily swayed by what a VC thinks we should do.

Being a Woman Entrepreneur

Doria: How do you feel that you were treated as a woman?

Maggie: Most of the VCs we met with were men. I always felt respected. I didn’t always feel understood, especially because our business is in the retail space. And so we got a lot of, “oh, my wife would love your product,” “my secretary would love your product,” or what have you. It was definitely challenging, and I felt the difference in pitching when I would pitch to female VCs. Fortunately for us, they understood the product a bit better, and they got the need, and they would use the product and be like, “Yes, this makes sense. I would definitely buy from you,” which was helpful. 

You want your VC to really feel passionate and believe in your product and be a consumer of your product, frankly. And our VCs today are consumers of our product, so it works really well. But we were very fortunate because I raised a year ago. If I had raised 10 years ago, I don’t think I would have come up against many women. But we actually spoke with a lot of female VCs, so we’re very fortunate in the fact that the landscape has changed a bit. I’m sure some of the early female founders who built companies 10-plus years ago had more problems and trouble than we did, but it was definitely a little bit challenging.

Doria: You’re a mom and a wife in addition to a CEO. I would ask this if I focused on men too, but I don’t: How are you able or are you able to find time for yourself?

Maggie: No, I’m not. I would love to sit here and tell you I find time and I balance my life. And being an entrepreneur, especially at this stage of the company, it’s very hard to find balance and to find time for yourself. I even find it very challenging to find time for my family. I have to actively and consciously go out of my way to do that. And so if I do have a little bit of time, I always prioritize my children and my husband, and outside of that, my sister, my brother, my mother, whoever, before I prioritize myself. 

How do you feel about that? I’ve accepted it. Honestly, it’s par for the course. I’m a realist. I will start with that. I went into this knowing that I would have to give everything to do this, and prior to this at Plastic, it was the same way. So I’d spent 10 years already not prioritizing myself. And not to say I don’t do things for myself, I do, but not as much as any sane human should, but I knew going into this that that was going to be my life. And I will say it really helps that I love what I do. So, day in and day out, it doesn’t feel like I’m not prioritizing myself because I love every single day of my job.

Doria: That’s fantastic. And it also reminds me that success is not easy, and I think that I don’t want to blame it on the media because I’m a journalist. But there’s the idea of overnight success, and no one knows about the 20 years that happened before you got there. And I appreciate your realism because I do think that sacrifice is part and parcel of the journey.

Maggie: It is. I can’t sit here and say, “This is so easy. Being an entrepreneur is the greatest thing. There are no challenges. You can balance it all.” Absolutely. You cannot. But you know what? I always say this to my team. If it was easy, everybody would be doing it. It is challenging, and it is supposed to be hard.

Doria: Yes, absolutely. That’s why, you’re one of the few. Can you share any insights or lessons learned from pivoting your career and founding two successful startups?

Maggie: Yeah, the career pivot was probably the biggest one because, again, I went from, sure, we’re still in tech, but I knew nothing about retail. I had to learn everything when it came to retail partners: how they operate, what their margins are, how to successfully pitch to a retail partner, and all that fun stuff. What e-commerce is, what is successful add to cart retention, all of these things that I didn’t have to deal with. Plus, we were a B2B. I went from a B2B to a B2C. So lots of challenges. 

I learned that research and networking is your best friend. So talking to as many people, and doing as much research, I also learned that you could pretty much do anything you want to do, whether it’s in a field you are familiar with or not, as long as you’re willing to put in the work. So if you’re willing to, again, meet with the people, have the coffees, understand the industry, do your research really grind, you could do anything. 

If I wanted to pivot my business after this and move into the health space, I wouldn’t feel intimidated because I did that once, so I would feel like that’s great. It’s a field in an industry I don’t understand, but I know I can get there. Will it take me a little bit longer than somebody who spent 10 years in health? For sure, it will. But I now have the tools in my wheelhouse to know that I can do that.

Tools for Success

Doria: What would you say are the three tools? Network? Research? Is there one more tool that you want to add for people who are on their journey?

Maggie: I’m going to say patience.

Doria: I don’t have a lot of that either.

Maggie: So that is hard. I told you, right Doria, I told you. An entrepreneur is not patient. But you have to be patient when you’re entering into a new industry in a field that you’ve never worked in. We also are revolutionizing e-commerce. 

We’re doing something that hasn’t been done in North America ever before. So that’s a whole other level of patience. We got 100 more hundreds of nos from retailers before people started being like, oh, okay, maybe there’s something here.

Doria: So when will you raise again?

Maggie: Probably in the next 12  to 18 months.

Doria: And what would success look like for you? Say 10 years from now, we want…

Maggie: ShopThing to be a household name. I want to have as many as humanly possible people to be able to have a side hustle and shop on ShopThing, as well as customers. I want them to be able to buy on ShopThing. And so it really, truly is about building this incredible community. 

The other thing I will say is because this is a female-focused podcast, really important for us. In the early days, we set out to build this gig economy, and we’re going to get there fairly soon, but it was really important to us to focus on women. If you think about most of the gig economies that exist, like Uber — Instacart’s not so bad, but that came in a little bit later — Airbnb. They don’t really favor women. You don’t feel safe as a woman to host. You don’t feel safe as a woman to drive. And so we really thought about how we can create something that is safe for women. And going out and shopping on your day off or whenever you want to is a really nice, safe way for women to be able to have a side hustle or make it their main hustle, whatever that is, but allow them an opportunity to be a part of the gig world.

Vision for the Future

Doria: Are you going to, at some point, have women who, say, create their own clothes?

Maggie: Absolutely.

Doria: Will they also be able to sell?

Maggie: Yeah, absolutely.

Doria: That’s great. So that means that women, who may be staying at home for whatever reason, will also be able to do exactly that.

Maggie: Can still participate. You got it.

​​How to Get Involved

Doria: Fantastic. And how can people find out more if they want to either download your app (I think that’s obvious, but we’ll say it anyway) or want to apply to be an influencer. How can they do that?

Maggie: Would love it if everybody downloads the app. It’s an incredible experience.It is cool if you do nothing more than download it and then leave me some feedback somewhere. I love feedback from users. toDownload our app ShopThing on the iOS and Android app stores. You can find us on Instagram at ShopThing. We’re also on TikTok at ShopThing, and our website is ShopThing.com.

Doria: It is really cool what you’re doing, and I can’t wait to continue following you.

Maggie: Thank you so much. Thank you for having me.