955 Jennifer Tsay:

Wings of Inspired Business Podcast EP955—Host Melinda Wittstock Interviews Jennifer Tsay

Melinda Wittstock:

Coming up on Wings of Inspired Business:

Jennifer Tsay:

There’s been a lot of press that platforms are not great for the freelancers on it, whether it’s Uber or Instacart or something, there’s always some, some sort of like sorted story about that. But we’re not like that because our team is comprised of people who started from a creative background. So, we’re really fastidious about how do we protect people’s time, how do we compensate people for their time if clients are late or if they, you know, they stay, is there anything we can do to help pass along the benefit to them? So that’s something that we’re really dedicated about.

Melinda Wittstock:

The number of freelance creatives is projected to reach more than 90 million people by 2028, with the freelance market now valued at $500 billion this year, as people seek more flexibility and control over their lives. But with that comes more competition and income instability. Jennifer Tsay is the founder of a platform for photographers called Shoott, and she’s on a mission to make it easier for photographers to find steady work by aggregating gigs in one location and time, while offering clients the opportunity to pay only for the photos they purchase. It’s an innovative model and we break it down today.

Melinda Wittstock:

Hi, I’m Melinda Wittstock and welcome to Wings of Inspired Business, where we share the inspiring entrepreneurial journeys, epiphanies, and practical advice from successful female founders … so you have everything you need at your fingertips to build the business and life of your dreams. I’m all about paying it forward as a five-time serial entrepreneur, so I started this podcast to catalyze an ecosystem where women entrepreneurs mentor, promote, buy from, and invest in each other. Because together we’re stronger, and we all soar higher when we fly together and lift as we climb.

Melinda Wittstock:

Today we meet an inspiring entrepreneur who has innovated an on-demand photography platform that’s shaking up the traditional photo shoot experience. Jennifer Tsay is the founder and CEO of Shoott – that’s shoott with two T’s – and today she shares how her unique background, stretching from investment banking to acting, inspired her to create a business model that supports both photographers and clients. With Shoott, photo sessions are free, and clients only pay for the images they love, a bold move that has proven its worth in over 60 cities. Jennifer dives into the early days of experimenting with this new approach, the challenges and victories of scaling nationwide, and how the company pivoted through major shifts like the pandemic and changes in online advertising. She also opens up about the power of nimble marketing, the importance of context over trends, and her vision for expanding Shoott internationally—all while supporting a thriving community of creative talent. 

Melinda Wittstock:

Jennifer will be here in a moment, and first:

What if you had an app that magically surfaced your ideal podcast listens around what interests and inspires you – without having to lift a finger?  Podopolo is your perfect podcast matchmaker – AI powered recommendations and clip sharing make Podopolo different from all the other podcast apps out there. Podopolo is free in both app stores – and if you have a podcast, take advantage of time-saving ways to easily find new listeners and grow revenue. That’s Podopolo.

Melinda Wittstock:

Any solopreneur creator knows the kind of hustle it takes to build and sustain a client base all in an AI world and increasingly competitive market.  Jennifer Tsay saw firsthand how challenging their lifestyle can be—constantly chasing gigs just to make ends meet. Determined to find a solution, Jennifer set out to rethink how artists connect with opportunities. So, she devised a business model that makes it easier for artists, like photographers, to find steady work by helping them find clients, providing fair compensation, and aggregating gigs in one convenient location and time. So, instead of photographers scattering around the city for individual jobs, Shoott invites clients to a single spot, such as Central Park, New York, where a multiple photoshoots can be booked in time slots. The platform pays the photographers for their time, and the shoots are free for consumers, who only purchase the photos they love. Through this innovative approach, Jennifer helps artists benefit from the power of volume, bringing stability and efficiency to the freelance artist life.

Melinda Wittstock:

Jennifer shares how she built her people-first platform, her 14-day rule for marketing, plus how she plans to scale her business. 

Melinda Wittstock:

Let’s put on our wings with the inspiring Jennifer Tsay.

[INTERVIEW]

Melinda Wittstock:

Jennifer, welcome to Wings.

Jennifer Tsay:

Thanks for having me. I’m happy to be here.

Melinda Wittstock:

I’m very curious about your business model offering free photo shoots where the clients only pay for the photos they love. Now how does that work? How do you make money doing that?

Jennifer Tsay:

That’s such a great question. And it’s honestly like the first reaction that most people have. So, the reason that our business model exists was we really thought about how hard it is to be an artist and that the artist life is very gig to gig, meaning I may have a gig this week, I may have a gig that week. But your whole life is spent trying to cobble enough together enough gigs so that you can sustain yourself and support yourself as a working artist. So, we were like, can we solve that in some way, shape or form? And we thought, hey, you know, instead of having these very disparate gigs, can we aggregate gigs together? So basically, if we say like, if you’re looking for a photo shoot, come to Central park at this one location, you know, the photographer will be there between one and five. There’s different half an hour slots, you can book those. And that’s like a very easy way to kind of see if we can kind of aggregate demand in one, one place. And then also the photographer gets to benefit from volume.

Jennifer Tsay:

And if that happens, we get to pass along the benefit of two photographers, I’m sorry, two clients in the form of a free photo shoot. So, this was kind of like a crazy hypothesis because no one has ever had ever really done it like that before. And when we did it that way, we did have immediate demand, and we found that it did work. So instead of having to charge more because you have less sessions, we kind of bore the brunt of that risk. And we said, okay, then the onus is on us to find really great photographers who provide really quality photos. And if we do that and we give this offer that’s really great for clients for a free photo shoot, will they still buy photos? And the answer has been a resounding yes. So, it sounds like it wouldn’t work, but it actually does.

Melinda Wittstock:

That’s fantastic. And so, you go for a photo shoot, and you get like a zillion photos and not all of them are good. Right?

Jennifer Tsay:

So, the whole thing is like, we have to provide great enough photos. And in general, out of a 30-minute session, our average gallery, we say that we’re going to deliver 40 photos at least. But our Average gallery is around like 90. So, it gives people a lot of choice. Because the thing is, like, when you. When you use a regular photographer, oftentimes they will say, oh, you know, you have to pay 3 to 500 up front, and then we’ll give you 10 selects, something like that. Their selects might not be the same thing as yours.

Jennifer Tsay:

The great thing is that you have the luxury of choice, and people really enjoy that. And they do. They choose, there’s no pressure to buy, and they only pay for the photos they want.

Melinda Wittstock:

So that just sounds like it works for everybody. So, what made you interested in starting a photo business to begin with? Like, your background, Jennifer, is so diverse. I mean, not only are you an actor, but, you know, you’ve also worked in investment banking and project management and documentary film producer. A whole bunch of different, different things. So how did you come to launch Shoott?

Jennifer Tsay:

I always encourage people to get a broad base of experience, not to. Not to be afraid of. Not of doing that. I think the important thing for me was I really was. For all those different types of experiences, I was like, what do I really enjoy here? What do I not enjoy? And just like, making a list for myself in my head. You know, I did start with investment banking, and from that, I’m so grateful for that time because I learned how to work in a corporate environment. I learned how to work with spreadsheets, with presentations.

Jennifer Tsay:

I developed my work ethic there, and I was no longer afraid of working hard. I think. I think, like, in the beginning, you’re like, oh, my gosh, I’m working so hard. And then. And then you realize you’re like, no, I actually have a pretty good amount of stamina as long as I really enjoy what I’m doing. And so, I had that. But then I was like, you know, but I like the work that I’m doing.

Jennifer Tsay:

I’m able to do it, but I’m kind of bored on some level, right? And I was like, let’s see, let’s try different things. So, from there, you know, I was like, what if I do something less investment banking? So, I did strategic finance. And then I said, let’s do something totally, totally different. And I helped produce a documentary. And so, I was like, how is it doing an industry? I don’t understand at all. A lot of it is like, you know, problem solving. So, I’m like, oh, I like the problem-solving aspect of it. And then I went into acting, which is a totally different departure.

Jennifer Tsay:

And I was like, what is it like to do arts full time? How is that life like? And I was. I really loved acting and I loved. But it was a totally different way of thinking. And part of me also really missed the, like, missed business, the different aspects of it, and not having a fully creative life. And while I was an actor, I knew so many talented people that just were living.

Jennifer Tsay:

When I say paycheck to paycheck, they had like $2 in their bank account. And I’m like, this is so unfortunate. And these people are hard and they’re so talented. I wish there was a business model that could help them work more instead of having this, like, you know, you’re just waiting for your next gig. So that kind of stuck with me. And then, you know, I had the chance to. I was working. I’d worked for my many day jobs with a serial entrepreneur, and we got together one day and I was like, I really want to do something for.

Jennifer Tsay:

For artists on some level. And then we’re talking about my experience and I was like, what if we do something that helps drive demand for people that work in kind of the gig economy? And we realized we couldn’t do it for acting, but we could aggregate demand for photography. Even though I do not have a background in photography, but we decided to give it a try anyway. And that’s kind of the very roundabout way of how I got there.

Melinda Wittstock:

That’s so interesting because it’s a business that’s combining this creative side of you with the business side of you. You know, like on one far end you’ve got investment banking, on the other side, acting. And so, this feels like a way that you’re combining these things.

Jennifer Tsay:

Yeah, I would definitely say so. I would say, you know, I don’t regret any of the jobs that I’ve ever had. And they do help inform me today in terms of pulling together different perspectives and different approaches and different understandings of things. So, like, when it comes to problem solving, I just have a broad base to draw from, and I love that.

Melinda Wittstock:

So, what was it like starting the business? So, like, you know, you’ve got this hypothesis and so tell me about the early days.

Jennifer Tsay:

Yeah, the early days were like, how.

Melinda Wittstock:

Did you test the hypothesis? And when did you know that it was actually working?

Jennifer Tsay:

Yes, so when we started, it was like, let’s just do the bare minimum just to get it out there, right? So, you have to have a website, you have to have a booking system. We used to kind of out of the box solutions at the time. And then we were like, well, you know, let’s market just to our friends and our network in New York City. So, we sent an email to like all of our, you know, our entire network and we just, it was really affordable pricing at the time, but the same, the same business model. And we’re like, do. Are people even going to book this? Do they even care? And the answer was yes. We were fully booked out with very little availability the first weekend that we launched. And we’re like, okay, we have something here.

Jennifer Tsay:

People like this offer, they want professional photos, whether it’s for business, headshots, acting headshots, you know, photos with their pets for engagement, family photos. People were booking. So, in the early days it was like 2018. So that meant that Instagram was really new. So, we were like, oh, it’s going to be a lot of influencers, and you know, millennials and things like that. But then we had some demand. Once we spec it out, we’re like, let’s run some ads. So, then we started with a little of Facebook advertising and we were like, okay, we could get some demand there.

Jennifer Tsay:

That’s really great. And then we were like, you know, we have demand, but we could have more. And then we decided to try different locations, and we tried Hoboken in New Jersey. And I don’t know if you know anything about Hoboken, but it’s a lot of young families. And as soon as we put a schedule up there, it booked out like crazy. And then we ended up our first weekend there having three photographers working full time. I think they all three of them had like 15 clients that day. And we were like, oh, the main demographic is actually families.

Jennifer Tsay:

Families with young kids in particular. Right. Always want photos of their children. And the photographers out there, generally they’re charging you like three to five hundred dollars for an hour or a few. And then you might not like the photos, all that stuff. So, when something’s super convenient and local to them, they really enjoyed it. And that’s how we got our footing. And then they grew exponentially once we figured that out.

Melinda Wittstock:

Interesting. Okay, so you start in New York City and then you’re in 60 different cities now. That’s like big expansion. So, so were there any challenges around that? Or, or I, you know, you got to find the photographers. You know, on one hand you’ve got this kind of double-sided market, so you’re finding the customers, that’s one thing, but you’ve got to line up the photographers as well. So, tell me about what it took to scale it to that level.

Jennifer Tsay:

Yeah. So, in order to scale it, we have two things that we needed to figure out is one, hiring photograph. The photographers come first. We need at least I would say, like four or five photographers in a market to even launch the market, because they don’t have full time availability. Right. We’re actually booking them in their supplemental availability, so we need just that amount. So, there’s a whole challenge of, like, how do we get the right photographers? How do we know we’re doing that? And we actually figured that out during the pandemic. The pandemic actually forced us to figure out how to hire remotely.

[PROMO CREDIT]

Wings of Inspired Business is brought to you by the new podcast, Zero Limits Business Growth Secrets. Join me together with Steve Little – serial entrepreneur, investor and mergers & acquisitions maestro – as we explore the little-known 24 value drivers that spell the difference between a $5m business, and a $50mm even $500 mm business. That’s Zero Limits Business Growth Secrets, produced by Podopolo Brand Studio at zerolimitsradio.com – that’s zerolimitsradio.com and available wherever you get your podcasts.

Melinda Wittstock:

And we’re back with Jennifer Tsay, CEO and Co-Founder of the professional photography platform Shoott.

[INTERVIEW CONTINUES]

Jennifer Tsay:

In the very beginning, it was me test shooting all of the photographers. Like, I would meet them, I would fly out, I would, you know, I would. I would talk with them, all of that. And then. And then when the pandemic came, I couldn’t do that. And we were, like, can we do this remotely? And we figured out a way to do it remotely, which was really great. It helped us scale immensely. And what was cool, unexpectedly about the pandemic was we were one of the few activities families could do that was safe because we’re outdoor and socially distanced.

Jennifer Tsay:

So, it was like a nice activity to get people out of the house in a safe way. And then the other thing we needed to do to scale was how quickly can we offer cities onto our website? Very quickly, so that we can have them bookable and run ads on them. And so, we figured that part out too, which was just building a proprietary tech platform that could support the addition of new cities that we could then advertise. And so, we worked on both of those things simultaneously. And it allowed us to go from really just one city to 60 cities in just like two to three years.

Melinda Wittstock:

Wow, that’s amazing. So, is this all bootstrapped or did you finance it in any way?

Jennifer Tsay:

So, we had financing in the very beginning. Meaning, I would say the very beginning. Like, I would say like 2019, 2020, where we were growing exponentially around the time of the pandemic. And it looked like our trajectory was crazy. And so, one of my co-founders is a serial entrepreneur and he’s a funder, so he did a friends and family round. We got some initial funding from that. Then in, I think it was 2021, when iOS 14.5 dropped, which was Apple’s privacy changes.

Jennifer Tsay:

It basically just made Facebook ads a lot more expensive because they were a lot less effective, because the targeting was not there anymore. It affected every single direct to consumer brand that was advertising on Facebook. And so, before where we could get clients, we didn’t have to think about marketing. We could put up ads and automatically find the right people. All of a sudden that, that left. After that we became a totally different company because we had to figure out our marketing and none of us were marketing people. So that was one of the biggest, I would say like existential challenges that we had to figure out. And so, my co-founder and I were forced to learn marketing from scratch to figure out if, whether we had the chops to run the business after that.

Melinda Wittstock:

You know, when people build things and they’re dependent on third party platforms, whether it’s like Tick Tock or even Amazon, you know, just one little algorithmic tweak. And now with AI coming and you know, I, it’s, it’s really complicated. So, what were the solutions you found to get around that issue where you’re at the behest of the algorithm and like you have no control over it. What did you start to do?

Jennifer Tsay:

In the early years we were, we were, our goal was growth, right? And when your goal is growth, you’re not thinking about profitability at, you’re like, let’s try, let’s try this advertising platform, let’s try that, let’s try this for branding. So, you’re just putting a lot of money, let’s build our team, let’s try to do this right. All of a sudden when our profit, our margins started to look insane in a bad way, and we just didn’t have control over it. We then became a, how do we become as profitable as possible? So, we cut out every single expense. Like all of a sudden, you know, our, our, our brains had to like scan through every expense that we had. How do we cut all of that, that as much as possible. We had to reduce headcount a little bit to deal with that.

Jennifer Tsay:

We then had to learn marketing from scratch, which was really painful when you don’t have that as your background. And you know, because in those days you’re like trying things and then you have to figure out how to try and test things in as lean of a way as possible. You’re like, what is the minimum viable approach? Like what is the minimum spend that I can do? Just to test it out, whether it’s an ad or you know, verbiage or whatnot, just to see if it lands before I pull it and try something different. It’s like death by judgment calls and being able to just forge forward and keep doing the things that are working and just scrap all the things that aren’t. And so it was, like, a really big mindset shift, I think, of one where we went from, like, you know, growing super-fast to one of extreme discipline and being like, are we making all the right decisions? Can we make the decision in a better way? How do we just tweak it to make sure it works? And slowly but surely, like, we caught our way to profitability, which is something we’re super proud of, because I think we went from one year where we had, like, a net loss of, like, negative $700,000, which was scary to then, and we were never going to get funding after that. And then after that, the year after we finally hit breakeven, which was a major accomplishment.

Melinda Wittstock:

Right. So, you mentioned something really important that in the marketing is that you have to be willing not only to test a lot of things, but abandon them quickly. Like, how long did you, like, let a test run, say, on any of the different things that you tried?

Jennifer Tsay:

I would really, honestly, the max is 14 days, right? If you don’t see the trends that you want to see in those 14 days, because every platform will tell you, oh, you should wait 30 days. I don’t need to wait 30 days. If I wait 30 days, I’m spending twice the amount that then. Then 14 days at something that might be a failure. So, like, if I don’t start to see, to me, it’s a little bit like dating.

Jennifer Tsay:

If I don’t start to see interest, I’m just like, no, I’m leaving. That’s kind of how we dealt with our marketing as well. And it’s actually proven to be very. A very good litmus test for us. And then the other corollary to that that’s really interesting is just because something might not work now doesn’t mean that it might not work in a different season. So, for example, what might not work in the summer might work in the fall when we have a lot more demand. You want to, like, scrap what doesn’t work for now, but, like, keep it in your pocket to be like, do I want to try testing that in the fall just to see. So, you know, there’s different approaches to that, but it’s a lot of pivoting.

Melinda Wittstock:

So, you’ve got a lot of different markets, though, that you’re, you’re reaching out to. And I’m going to start with the customers first, consumers, because, yeah, they may want family or photos of their kids or, you know, that kind of thing. You know, Christmas card, family photo, stretching through to professional headshots. Companies that need like their whole team, all these sorts of things. And so, they’re different marketing messages to different people. So how long did it take you to figure out your different messaging for these different segments?

Jennifer Tsay:

You know, it’s so funny. Our marketing has always gravitated towards, like, we would try different messaging, but like, what is really effective has been very consistent, even though we do try other tests. So, like, for example, people will be like, oh, you should definitely run video. Video is going to do so much better for you. Video does not do better for us. It is consistent that no matter who is our marketing agency, we run like a 4 grid where it’s, it’s like, it’s like if it’s a square, it’s like a four grid of four different photos with maybe a call to action in there. And that’s what resonates the most. Literally, no matter what else is going on, it’s the craziest sort of thing and it kind of a little bit defies logic, and we try to other things, but that’s been the best thing for us.

Jennifer Tsay:

And you know, and we also notice that the things that work best are when we mention that it’s a free photo shoot, because that’s an immediate hook for people. And, and that’s just kind of been, you know, we’ll do different formats that will do different variations, but generally those are the things that we’ve noticed work. So, we just keep using that in different ways on our, on our creatives.

Melinda Wittstock:

So, you mentioned, like, the things that are working, like in terms of the messaging, like mentioning that it’s free, you know, you know, that video doesn’t work for you. 

Jennifer Tsay:

Yeah, exactly.

Melinda Wittstock:

But in, in marketing, there’s all this pressure to do the hot new thing. And, and as entrepreneurs, we always want to kind of chase the next new thing, like new is exciting. So how do you know what to test or what not to test? 

Jennifer Tsay:

I think we test what makes sense for us. So, like if the messaging seems kind of in alignment with what our bait, you know, our base client might be interested in, we’ll try it. Right? It’s like not hard for us to try things like trends. It’s not hard for, you know, we’ll always, we’ll always try it. But I mean, yeah, I, I think it’s again, it’s like so much judgment about like what, what is going to resonate with my base and let’s try that. We don’t have to try everything because I think, I think one of the things that we’ve noticed is like we work best when we do things in context. I think sometimes people are like, instead of thinking in context, they’re like, for example, oh, you should run ads for 30 days because that’s the common wisdom. And they said that.

Jennifer Tsay:

So, let’s just do that. And I think we don’t tend to do things just because something somebody tells us we should, because just because it might work for somebody doesn’t mean it will work for us. It doesn’t mean we won’t try it. But we were not married to that concept. Does that make sense?

Melinda Wittstock:

Yeah. 100%

Jennifer Tsay:

I think a lot of people are married to like, like theory and we’re not married to theory at all because I feel like, I feel like it makes you less nimble.

Melinda Wittstock:

Right. So how do you find your photographers then? Is there some master database somewhere or you just…

Jennifer Tsay:

Oh my gosh, I wish. Yeah, right.

Melinda Wittstock:

Like, I mean, maybe that’s another business line for you, but how do you, how do you find the great photographers?

Jennifer Tsay:

Honestly? CraigslistCraigslist is such a, such a, you know, time honored, like source of greatest. And then, you know, a lot of photographers will just find us on social media and apply that way. Or like people will refer photographers, which we always love, or photographers refer other photographers. It’s a lot of word of mouth because when people find out about us otherwise there’s a lot of suspicion. Like photographers, I feel like they’re small business owners. So, they can also be very suspicious of a platform.

Jennifer Tsay:

The concept of a platform that like helps creatives is just some, something that other people are just not trusting. There’s, you know, there’s been a lot of press that platforms are not great for the freelancers on it, whether it’s Uber or Instacart or something, there’s always some, some sort of like sorted story about that. But we’re not like that. We’re. We try not to be like that because our team is comprised of people who started from a creative background. So, we’re really fastidious about how do we protect people’s time, how do we compensate people for their time if they have to. If clients are late or if they, you know, they stay, is there anything we can do to help pass along the benefit to them? So that’s something that we’re really dedicated about.

Jennifer Tsay:

But it is, it is hard for us to find photographers because there is a hurdle that we’re a scam or that how do they make money if our photos are, you know, free? It’s a free photo shoot. How do we make money that way? How do they feel secure, if that makes sense.

Melinda Wittstock:

Yeah, no, totally. And so how does it work in terms of the revenue? I imagine there’s a revenue split. Like the photographer needs to be paid for the photographs that the customer buys, but you also need to be paid. So how does that split work?

Jennifer Tsay:

Yeah, so the first thing is that we give them $100 per shooting hour guarantee. So that is to really give people a comfort that like if, say, say they happen to have a day where nobody buys photos, they’re going to get paid anyway for their time, just for showing up. That really happens. But that’s our protective blanket. After that, they basically, they have commission on sales, so they earn the higher of that commission rate or that minimum guarantee. And I’ll just, like, it’s a lot of math, but I’ll just say in 2024, our average shoot photographer was basically making between $166 and $200 per shooting hour. So, if they showed up and they were photographing, that’s what they were making from that time.

Jennifer Tsay:

And keeping in mind, you know, keeping in mind that we’re doing all of the business activity, we’re doing all of the marketing, all the research, all the analytics, all the customer service, they don’t have to deal with the customers afterwards, all of the sales, all of that stuff. And then we also give them stats about how they’re doing; we also aggregate feedback for them. So, we’re really designed as a great source of supplemental gigs and income for a talented professional level photographer.

Melinda Wittstock:

So, a photographer could kind of backfill, I suppose, with this, like say they have their own gig practice, maybe their own studio. All of this just like extra work, you know. Right?

Jennifer Tsay:

Yes. there’s actually a split of profile across our base. I think we have about 888 photographers right now actually. If not exactly, we have something right around there. Some of them have like a full-time day job. They just happen to love photography. 

Jennifer Tsay:

And then so we fill their schedule that way with their weekends. Some people have full time, are full time photographers and then just want to pick up some extra gigs because this economy is scary. So, they do that. Some people are like full time moms and then want to make extra money for themselves. Like it’s, there’s so many different profiles that are really fascinating and we love that we can find work for these people, so they don’t have to spend all the time like it’s hard enough for us to find work for them, if that makes sense. Like, but we’re, we. There’s so much more power in us doing that as one entity and then being able to split the work for people versus like all of these individuals trying to find work for themselves. When I’m like, no, you guys should actually really just focus on what you love to do, which is photography.

Melinda Wittstock:

Right. So how is AI impacting your business?

Jennifer Tsay:

Yeah, so I will say that AI luckily does not really compete with what we do because nobody wants an AI photo of their family for their Christmas card. When you’re getting family photos, maybe an option, you might want one or two where you see. But to have a completely generated photo of your family, literally nobody wants that. That’s kind of weird. So, we’re really in the business of like IRL. Like you know, in real life, like AI is important and AI is really interesting. But people have also real lives and real moments and real relationships and real milestones they want to capture. So, to that end, like AI doesn’t impact us that way.

Jennifer Tsay:

AI is helpful, for example, for the technological advancement that like it helps photographers edit faster, it helps them, you know, maybe be able to turn around photos faster. It helps us run our business a little easier. There are certain things that were really manual before that. Like you know, we can write blog articles faster, we can, you know, we can make certain creatives a little faster. But by and large like our core business, which is very much people oriented both for our clients and for and for all these Photographers, that does not change.

Melinda Wittstock:

Yeah, that’s really interesting. What about AI in the operations of your business? Does it help you with, I don’t know, customer targeting or efficiency or are you applying it in any way? This is sort of like a standard question I’m asking everybody now.

Jennifer Tsay:

Yeah, yeah, yeah. So, AI, like we use AI every day. But like for example my, my dev team uses it and they, they fly through tickets so much faster. So, like on the coding aspect it really speeds up their process. It’s really great for them. I would say on the operations side, we’ll often rely on AI for like to look at analysis or like if we have to have drafts of things for clients or like hey, you know, help us formulate response for this RFP, things like that. It’s like the first, it helps you get a first draft much faster to work with. Same thing with like just you know, things that, where it would take you a long time to explain.

Jennifer Tsay:

We could just like put in reports or analysis and then it could spit something out. So, there’s, there’s ways in which has been, it is really helpful. It’s a lot of the like soft, softer like things that you have to figure out how to language, it’s much better for that. And then we use a little AI here and there for like you know, coming up with creatives and like improving creatives where we’re like oh, you know, I want more sky in this photo for this ad so I can put text there. It does that so quickly. Where before you would have to like Photoshop that for like three hours was awful. We can do that instantaneously now. So, you know, there’s just little time savers here and there that make us be able to focus on the core aspects, the strategic aspects of our job a lot more.

Melinda Wittstock:

So, what’s next for you? How do you see the business growing from where you’re at right now?

Jennifer Tsay:

Yeah, so I think we’re trying to really look for international expansion that would be really amazing. We’d love to be able to bring this to Canada to you know, start with English speaking countries just because of where our, our support team speaks English. So, like, you know, whether it’s Canada, Australia, that kind of New Zealand, that kind of thing. And I also think that we really just want to make our service more robust for our photographers as well. Like is there some world where we can provide them access to benefits, make it really like, make it a really rich platform for the photographers. So, you know, we’re trying to be creative there. We’re trying to see if, you know, if we can. One of the biggest things really is also a lot of people still don’t know we exist.

Jennifer Tsay:

Like, we’ve been around for seven years, but because we don’t have a ton of money to throw into branding, a lot of families don’t know we exist. So, when they find out about us, they love us. We’re 4.9 star rated on Google, but a lot of people still don’t know we exist. So, it’s something that we really want to keep working on to just keep building our base and keep building, you know, on, on our momentum, even in the United States. Yeah.

Melinda Wittstock:

I’m curious, would this model work for other things like video shoots or, you know, have you ever thought of that?

Jennifer Tsay:

We have thought of it. Video shoots are trickier because there’s also is an audio component.

Melinda Wittstock:

Right.

Jennifer Tsay:

And then I feel like with video, AI can do a lot of that because whereas our business is about your actual human relationships, when you do video, unless you’re doing video of your family, but that’s different. But like, if you’re doing video for like, like a lot of businesses need video and, and you can have AI generate that pretty easily now, it’s still a little, it’s still a little bumpy, but like. Yeah, so video is not really it for us in particular. And we’ve thought about, we’re like, oh, you know, can we, we were like, can we do this for tutors? Can we do this for whatever? So, we’re still thinking about it. I know, like, we have a great tech team, so we’re still constantly thinking about who we might want to apply this towards, but no clear winners emerge yet.

Jennifer Tsay:

Yeah.

Melinda Wittstock:

Ah, this is so exciting. And so, do you still have time to act? Do you still do acting gigs?

Jennifer Tsay:

It’s been like, I would say, you know, if, since a lot of my friends are still in the industry, if they ask me to do something, I’ll do it. But for the most part, I, you know, I’m kind of a responsibility girl. So, like, I support 880 photographers right now. That’s my priority. Right. So, like, I don’t actively pursue it. And plus, like right now with everything going on, there’s just less work overall. So, I’m like, you know, I kind of feel like it deserves to go to people who are really pursuing that full time.

Jennifer Tsay:

Right. That’s how I feel.

Melinda Wittstock:

Makes a lot of sense.

Jennifer Tsay:

Yeah.

Melinda Wittstock:

Wow. Well, this is so exciting. So, I hope you do expand to Canada. I spend part of my time here. I’d start with Vancouver.

Jennifer Tsay:

I love Vancouver. I know it’s a beautiful city.

Melinda Wittstock:

I go between Santa Monica and Vancouver.

Jennifer Tsay:

Oh, amazing.

Melinda Wittstock:

Yeah. I’m in Vancouver right now. It’s gorgeous.

Jennifer Tsay:

It is. It is so gorgeous. It would. It would photograph beautifully.

Melinda Wittstock:

100% Toronto’s a good one. Montreal is a good one. Well, Jennifer, thank you so much. It’s very exciting what you’ve built and building and people, if they’re interested, photographers, customers, they just go to shoot with2t’s.com and go from there.

Jennifer Tsay:

That’s correct. Shoott.com Amazing.

Melinda Wittstock:

Well, thank you so much for putting on your wings and flying with us today.

Jennifer Tsay:

Thanks for having me. Had a great time.

[INTERVIEW ENDS]

Melinda Wittstock:

Jennifer Tsay is the CEO and Co-Founder of the professional photography platform Shoott, which uniquely offers free photoshoots where clients only pay for the

photos they love.

Melinda Wittstock:

Please create and share your favorite clips of this or any other podcast episode via the Podopolo app and join us in the episode comments section so we can all take the conversation further with your questions and comments. Also, we really appreciate it when you rate and review the podcast on Apple and Spotify—it helps more entrepreneurs like you find the secret sauce to support and grow their businesses.

Melinda Wittstock:

That’s it for today’s episode. Head on over to WingsPodcast.com – and subscribe to the show. When you subscribe, you’ll instantly get my special gift, the WINGS Success Formula. Women … Innovating … Networking … Growing …Scaling … IS the WINGS of Inspired Business Formula …for daily success in your business and life. Miss a Wings episode? We’ve got hundreds in the vault, all with actionable advice and epiphanies. Check them out at MelindaWittstock.com or wingspodcast.com. You can also catch me on LinkedIn or Instagram @MelindaAnneWittstock. We also love it when you share your feedback with a 5-star rating and review on Apple, Spotify or wherever else you listen, including Podopolo where you can interact with me and share your favorite clips.