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Welcome to How I Built My Small Business. I'm your host, Ann McGinty. In today's episode, we're chatting with Jen Thai, the co founder and CEO of Shoot With Two Ts, a fast growing company making professional photography more accessible for clients and a reliable supplemental income for photographers. In just seven years, shoot has grown from 800,000 to over 9 million in revenue, achieving operational profitability and expanding services to over 60 cities across the U.S. jen shares her journey in a very candid and authentic way. We talk about leadership, giving and receiving feedback and why experience, even unpaid, is one of the most undervalued assets in today's time value culture. Jen was named a Forbes Next 1000 honoree. Brit's 30 AAPI founders we love to support. And on the side, she works as an actor and speaker. Shute has been featured on Forbes, who, Oprah Daily, the Today Show, People, and much more. You'll find a link to Shoot in the episode's description. If you've been tuning in, you know this show isn't about selling anything. It's about sharing meaningful stories and learning along the way. If How I Built My Small Business has brought you any insight, inspiration, or even just a spark of curiosity, there are a few simple ways you can support the journey. Follow the show, share your favorite episode with a friend, or leave a quick review. Each one truly helps me grow this show. Thank you. Let's get started. Jen, thank you so much for coming on the show. I'm really excited to hear your story.
A
Thanks for having me. I'm so happy to be here.
B
So, so where are you from? Can you give us a little bit of a background on you?
A
Yeah, I grew up in Allentown, Pennsylvania. So I, you know, I, I was there for like a good 13 years of my childhood, went to school in Philadelphia and I've lived in the New York area ever since I graduated, which has now been a little north of 20 years. You know, I did a lot of years in the corporate world doing investment banking, corporate finance. I tried doing a little bit of nonprofit work and then I transitioned into doing some creative work. So I produced a docum. I took acting and like writing classes. I was an actor and I still am sometimes for upwards of, you know, over a decade. So that's kind of how I got into the creative world.
B
How did that bridge over to starting Shoot really?
A
Shoot came about because I wanted to figure out a business model that solved the gig economy for a certain subset of artists so that they could stay artists because it's so hard to find enough work and cobble together enough work in the gig economy. And you, you know, being an actor kind of taught me that. So we figured out we could do it for photographers. But you know, all of this is to say I'm actually not a photographer. I came at it from an actor's point of view. Right. But I had a lot of friends who were artists of all different sorts. And we were like, well, we can't do a business model that kind of aggregates demand for acting. It doesn't quite make sense. So then we were left to think about what industry could have that. And we realized that we could do it for photography. Meaning the average photographer has to kind of find a gig here, a gig there. They have to cobble together enough gigs to create a living. But we were like, can we create a business model that aggregates demand all at one location so that the clients come and meet you somewhere? Right. So much the same way that like when you're in a, when I guess when you're an actor and you're in a show, all of the people come to your show and see you. We were like, is there a way to do that for photography where we can amplify the demand for them? So we realized if we station them at set places for a certain time frame that we could have back to back sessions for them. So that's really where that came from.
B
That's interesting. How did you test the model?
A
Yeah, so we did an MVP or like a minimum viable product of what we thought our business model could look like in New York with our friends and our just general business network. There were a couple of us working on it and we were like, oh does know if we advertise these free sessions where you only pay for the photos you want, is there enough demand? And we realized there was. So that was really exciting. You know, we just launched a really rudimentary version of our website. We had like a plug and play booking service and people booked the sessions. And so from there we really developed proprietary systems for it. But yeah, we trialed it with our own community.
B
And as far as cash flow goes, like, how did you know that the model that you had created was going to be sustainable?
A
That's such a good question. So we didn't look, we had a feeling. We were like, I think there's enough of a market because it's a volume game, right? A lot of things are a volume game to cover all of your costs. So in the beginning years, you know, we were like, how do we structure this that we get enough value from each of our clients and that we have also enough clients. So for the longest time you're kind of balancing what your pricing should be, what your advertising costs should be to warrant that. And so it took us five years to become profitable. Now we're like definitely a profitable entity. That's amazing. Like we hit break even in 2023, and then in 2024 we actually 20x to that profitability, which is, you know, it sounds crazy, but it was just north of like 40,000 the first year. So it is impressive. But at the same time, like, you know, we're going off of a pretty low number, but yeah, and then we were like, oh, this, this does have legs. So like, we have to really figure out how to maintain that no matter what's happening in the economy or whatever. But it was, it was a lot of very discip and betting that it did work in the first few years.
B
Can you describe a little bit more about how this business model supports the photographers, how it works for the clients, and then how you're able to make money as the company?
A
Yeah, that's a great question. Because our entire reason for being was to see if this business model we could create was like a win, win, win for us, the photographer and the client. So really we have this idea that a photographer stationed somewhere, you know, someone goes to Central park from like 12 to 5, has half an hour SE that they book out. We're looking to see can we attract enough people. It's really dependent on us to have the right marketing to attract the right types of people who want not just one photo, but multiple. So our main demographic are what I call like millennial and Gen Z moms. So that's really where people want the photos. You want photos and memories of your family. So that's really, you know, the impetus for who we're targeting. And then on the photographer side, we know that the whole offer of like a free photo shoot is really scary for them. So we do whatever we can to protect their time. We have always offered a 100 minimum guarantee per shooting hour. So if they're working, they're making money no matter what clients pay. And then we offer the greater of that amount or what they make on commissions. We have a commission structure as well. So the more photos they sell, the more they benefit. And on average, even though we have that hundred dollar minimum guarantee they're making, in 2024, they made between 166 and 1 per photography hour, which is pretty great. So we're always aiming to protect their time. We also give them extra payments if clients are late, if they don't show up, if they pick up extra sessions. There's all these other ways where we try to really incentivize them to work for us and make it worth their time and you know, the way that we work. So we take a cut of it, but the cut is really to support that we do all of the marketing, which is insane because it's like never ending changes in the digital marketing landscape that we have to optimize for. So we do all of that business strategy, you know, gallery delivery, customer service, they never have to like deal with the clients themselves. Basically all of the business activity we take care of. So they just have the freedom to come in their supplemental time and just do what they love doing, which is photography. So really it's meant to be a convenient source of supplemental income for preexisting photographers. And then, you know, the clients benefit because photographers want to make as much money as possible. So they're incentivized to give them the best experience and the best photos. And then there's that free offer. So it's a risk free upfront for them. So a lot of people who normally when, you know, you go for a photo shoot, it can cost upwards of like 400, 500, 600, if not more. And it's like multi hours and it's like, no, you have a half hour. You know, people are not going to burn out in the middle of that. Like it's the perfect amount of time for everybody. And it's an accessible price point where people can book photo shoots to commemorate all of their life moments, no matter how big or small. And that's what we're trying to incentivize is greater demand. And we started asking our clients and I think about 25% of our clients have said that they've never booked a professional photographer before working with us. And we consider that a major win because it's not like we're taking demand from other photographers. We're actually creating demand in the marketplace, which we consider a major win.
B
It is a pretty brilliant business model. I'm not going to lie. When I first was reading it, I thought, my gosh, how does that even work? I mean, how many sessions did you need to have before you reached a break even point?
A
Great question. So I feel like on a yearly basis we need to have at least like around like 43,000 sessions. Wow. It's something like that.
B
Okay. And then you have an office space I assume where everybody is working.
A
We do not.
B
You don't?
A
No, no, no. We're fully remote. So like the other part of us figuring out whether we're profitable was like, what expenses can we cut and how can we automate certain things so we can still keep our team really lean so we can start being profitable.
B
Okay, so where are the greatest expenses then?
A
The greatest expenses are definitely just the cost of paying the photographers. Definitely. Obviously that's going to be a huge portion of it. And then it's marketing. Marketing is a huge part of it because we have to really balance getting enough clients for them and optimizing. What does it cost to get them? Get them clients? Are we making also enough per client to make it worthwhile at the same scale that we're having? And our year's a little wacky because people want photos, but they really, really want them in fourth quarter the rest of the year maybe if they have like maturity. So you know, we're trying to incentivize people to come for the rest of the year, but like come like September, we don't have enough photographers to meet demand. It's so insane because everyone wants it for holiday cards and for family reunions, all of that stuff. Because of that timing, we actually don't know how we do financially until like January of the following year. So it's up to us to optimize for the year, hope we stick the landing, so to speak, and that it works out in our favor. But we don't know. And so there's always this, like, it's always terrifying for us up until we know how the numbers land.
B
It's an atypical seasonal business.
A
Yeah.
B
And so if somebody, let's say they go for their 30 minute session and there's 10 or 15 photos that they want, what are they spending?
A
At 10 photos you can get your entire gallery for 180. So it's like $18 a photo. However, it's actually less than that because we include like 20 dol retouching credit. So if you have like an extra trash can in there or whatever that you want to take out or you know, flyaway hairs or whatever that you want to adjust for, there's credit to go towards the retouching of some of your photos if you'd like. And then you can get your full gallery for 2 98. And that also includes even more retouching credit. And then we have like bundled packages with Paper Culture which they provide eco friendly print products. So there's like a photo book or photo cards, things like that to create, like invites or cards from.
B
How much has to be done on the back end as you grow in size. Like your team, how many people are on your team?
A
We have like 12 people full time, and then we have like six others that are like, that are part time for customer service. But our team team that really runs everything, we have 12 people. Five of those people are tech, so the remaining six, seven people are really doing operations or hybrid operations plus customer.
B
Service, and then the marketing. So is the marketing outsourced or in house?
A
It's a little bit of a hybrid. So we run some of it in house. And then we have an agency that runs our Google and Facebook that we watch like a hawk. Because marketing's so expensive for us and such a huge component to how we work. We look at it on a daily basis. We have a proprietary tracker, so we see how each platform is doing, and then we make decisions, you know, on a daily basis.
B
Smart.
A
Yeah.
B
And how effective are the various marketing strategies? What works for you and what doesn't?
A
Yeah. So there's the evergreen stuff. So Facebook is definitely an evergreen. It's our greatest driver of people. And then Google is also a huge driver, and the two work really well in tandem. It's nice because they play off of each other a little bit. Sometimes people discover you on Facebook or Instagram and then they Google you. So it's. Those two go really well together. And then we also use connected tv, and that's been an interesting one because when we first started using that, it didn't work for us. It was really expensive. And then now we've actually gotten it to work, which is fantastic. So we have one platform that we use, and we're still looking to see if there's other ones that are out there. And, like, not all advertising platforms are the same. Some of them don't have the best tracking and attribution, so you can't even tell what your ROI is. So it's a little bit of, like, experimentation, of like, hey, how do I run ads on. On Hulu or Disney plus or like, whatever. And then what does the interface look like? Can I tell what's happening with my money if I can't, we pull our money. So we're really good at doing very lean tests. Usually we've tried other things like podcast advertising, which is a little bit hit or miss, you know, radio hit or miss. There's things like digital billboard, which we haven't quite gotten ever to work. And then there's also guerrilla marketing. So, you know, figuring out, like, hey, how do I advertise to local communities? That's also different. So we try everything. We do really lean tests of, like, if it doesn't work in 10 days, we pull it. And then we always will come back and try again. Because sometimes people change their technology and it gets better.
B
Wow, this sounds like a lot of whack a mole.
A
It is.
B
So with shoot, you wanted to tackle an industry and you wanted to solve a problem. Where did this entrepreneurial spirit come from for you?
A
I think it's because I worked in corporate America and I didn't really enjoy that experience, even though I did enjoy the stability and the benefits and all of that stuff. And I was like, you know, I don't feel happy here. Like, I'll go to work, but I'm so bored. Like, once I learned my job, I'm super bored and not stimulated. And then I get very existential. And so I've always had that. I think there are certain times where having a stable job really matters. Right. I think if you have young children, actually, I'll say this. If you have any really major financial thing that you're trying to achieve, the stable job is great. Or if you have any health issues, I think about, like, all the reasons why. Yeah, there's actually a lot of reasons why. But there were points in time where I was like, no, I can gamble a little more. Like, I think I want something slightly different. And that's why I did transition into doing a lot of arts stuff where I was producing a documentary. I wasn't getting paid for it. I'd rather accumulate skills. And if I can gamble on that a little bit, I'm going to do that. I'm willing to forego the pay a little bit just to learn something and experience something new, because maybe I'll learn something about myself. And I think in the process of doing that, I discovered that I did like startup environments because everything was totally new and it was things that I didn't know. Like, I liked having different challenges every day. And so I realized when I. When I was in that environment, I was like, I kind of miss that. So it made me go back to being like, is there another startup that I can be part of or, like, work on? And so I kind of stumbled upon realizing that I had more of an entrepreneurial spirit than I realized.
B
And now that you've been an entrepreneur for seven or so years.
A
Seven, yeah.
B
Yeah. What do you miss about the corporate life or world? Or do you not. Would you ever consider Going back to.
A
It, I, I mean, I, I would say I do, I do miss the benefit. The benefits are better, you know, like, the health benefits are much better. You know, sometimes you do miss having an office to go to and having all of like the perks of like free coffee and all of that fun stuff. You can still have that, I think, in an entrepreneurial space existence, but we don't have that. So I think there's aspects of community and there's certain just perks that are really nice to have when you have a corporate entity. But other than that, I don't miss the work at all. I felt like I worked on a lot of things that were just nice to have but not very much necessary or I would work forever on something and it just like nothing happened with it. So I'm like, my work doesn't even matter. Whereas literally every decision we make as entrepreneurs makes a huge difference somewhere. So all of a sudden everything matters. And it's, it's kind of nice to work knowing that.
B
And those fringe benefits can come as your profitability increases.
A
Yes, exactly.
B
Have you taken anything, I imagine that you have, so I should rephrase that. And saying what have you taken from your past professional experience, whether it's the acting or it's the investment banking into your business world, what came with you, that's been the most helpful.
A
Oh my gosh. Okay. So like very practically speaking, the most helpful thing was for my investment banking days, like learning how to be very spreadsheet literate and create financial projections. When you're an entrepreneur, like, and money obviously matters because it determines whether or not you have a business or not, it's helpful to have those skills. It's helpful to know how to project things. Like, I can weirdly do that in my sleep. It's like a weird thing. It's like knowing a language. I'm like, oh, gosh, every time I look at a spirit, I'm like, I don't know if I can do it. And then I'm like, well, I can do it. Like, it's so strange. Strange. So I appreciate that.
B
Right?
A
Because if I had to learn it now, it would be like pulling teeth would be terrible. So to that end, like I having your, you know, and how to make a presentation, all of those things, it's really great to have. And then how to write, business writing, like getting all of those skills out of the way, really, really great. I would always recommend that people have that. And then from my acting days, I think what I really pulled from that is how to give people notes. So everything's hypersensitive in the acting world, and you have to know how to give people notes because people hear differently. And I see that in play so much as a people manager now, how to give notes, how to speak to people if they respond poorly, how to kind of tactically deal with all of that.
B
What do you mean by give notes?
A
Give feedback. Oh, feedback, Sorry, yes, it's called giving notes in acting. But when you give feedback to people on your team, it's also still touchy, right? It's the same thing. Like, people get defensive, and how do you talk through people's bs and how do you, you know, how do you kind of get people to do what you need them to do and have them grow and have realizations and all of that stuff? There is a sensitivity to that, and there is kind of a strategy you can have when you really understand the people on your team, which is important to have so, you know, seeing the people as the people they are.
B
Okay, so give us some tips then. Teach us what you know about giving notes. What's the best way to do that for the outcome that are hoping for?
A
How would I articulate this? Let me see. So I would say people are motivated by, like, they. They are both motivated and understand things very specifically. So, for example, I had a team member that you could tell them prescriptive things, but they couldn't understand it until you gave them, like, the overall rubric of like, hey, we're telling you this because, like, so if you were like, hey, just do A, A, B, C, and D. Like, they were like, I. Okay. And so then we were like, hey, we're asking you to do this for these particular reasons. This is why it's good for strategy, Whatever. Then they can contextualize what they're being told and be able to do it. So that's. That's one type of person. Another type of person. We would then try to talk to them as, like, from a contextual point of view, hey, it's really important that you do this because, you know, we need better oversight. We need to be able to share work streams. We could say all that stuff, but it wasn't until we, like, dictated A, B, C, and D that they could even do any. So knowing the difference between people. And then similarly, like, we have some neurodiverse people on our team knowing that and being like, okay, I know how you hear and I know what things suit you best. Like, this is how we're gonna try to come to this. Together and making it seem like teamwork. So I think understanding that everyone is different from each other and from you and figuring out how to problem solve that together, making them feel like they're part of that process and making sure they feel safe in that and not just criticized. A lot of people just come from AB background where they don't know how to take criticism. I think there's a lot of examples where criticism is only meant as a destructive force versus a constructive. Right. So knowing that there's already that kind of sensitivity there, like being able to plan and budget around that is really important.
B
That is such a good skill to have just in life, but then also in leadership and management and one that I wish was taught to everybody.
A
It's really hard.
B
It's like a very compassionate way.
A
Yeah. It's an EQ thing. And not everyone has the same definition of EQ or feel its importance.
B
Right.
A
And then. And then it's also about judgment because, like, you could read things one way, but somebody reads it a different. And then like, how do you bridge that in a way that. That again, feels like you're on the same team versus, like against each other, navigating all that kind of stuff. That's the soft skills that will really build or destroy your team for sure.
B
Yeah. And to keep moving forward without the judgment.
A
Yes.
B
So that everybody can communicate in a stronger fashion.
A
Yes.
B
So with the building of your team. So first of all, how many partners did you have going into this business?
A
I mean, it's changed a little bit, but like, we originally started with around three people. And like, some people jumped on, some people jumped off. And then we. I think we were always around like three people in the very beginning stages. And then we slowly started adding from there. So we added somebody to do customer service. That was like the first kind of like team member beyond the original team members on it. And then we started adding more and more people. So, you know, then we have more customer service people. We have a tech team, which we didn't really have until year, like three. And then we added somebody who does recruiting for a photographer or somebody who manages our locations or our partnership. So, like, we kind of added as we went, and oftentimes we took people who had much more seasonal jobs. So because we're fourth quarter heavy, we would need a lot of customer service people in fourth quarter. But then we'd have to let go of them or like furlough them from January through August, which is a long amount of time. So we're like, can we use These dedicated people in different ways. So then we gave them hybrid roles. So we actually have quite a number of people with hybrid roles. So we can make them full time. So our full time stays constant through the year. So that there's about 12 people. And then we have anywhere from like an extra one to six people handling customer service. Six being like the most additional, you know, the highest amount additional for fourth quarter. But that's kind of that Flex is really in that customer service portion. One of my co founders is my primary advisor, and he's a serial entrepreneur. So in the beginning, it was a lot of his guidance to be like, I think you should focus on this, I think you should focus on that. The more years that we were in business, we kind of figured that out for ourselves. We're like, hey, we need this, we need that. So we're like, how big is the need? Like, you have to prioritize kind of the needs that you have, and then you're also looking at the people that you have and seeing if there's a direct match. So, for example, if, like, I could get somebody, I was like, oh, God, we really need someone for partnerships. And we're like, hey, this resource of ours is really good with clients, so maybe they'd be really good with partners because it's kind of the same skill set. So then we kind of float that and trial that. And I do think, especially when you're doing something like adding skills to somebody, you can misjudge that somebody has a certain skill set or that they would like the additional work. Some people might not. Right? It's not exactly the best way. So I would always at least try it a little bit, see if they like it, see if they're good at it. And then if they are, then, you know, make that official.
B
With everybody being remote, what's your structure around keeping your team on the same page?
A
Yeah, so we have like an all team operations meeting on Mondays, and then separately, the tech team has their own meeting on Monday. And like, we kind of compare notes and look at things, and then everyone kind of goes off on their own. And then, you know, there's kind of this. Our customer service lead then tells the rest of the team that he has their his own meeting with them. So we also provide like email updates where like, hey, these are the development, what we're focusing on. These are the things that we've achieved. These are the things that we're looking at. I'll admit though, like, I didn't realize until maybe like this year or last Year I'm like, oh, it would be so much more beneficial if we had even just like one or two days in an office where the osmosis would be much more natural. Because now we have to be so purposeful about being like, who knows what, because sometimes we'll make a decision and forget to tell people, like, it's bound to happen. And also people might not really like that and feel left out. So, like, it's really important for us to be really conscientious about that. We basically do go through meetings, email updates, and then if anyone ever has any questions or anything where it's like, hey, you can always book a time with us. Like, you see the full availability of our calendar, just like we're usually online anyway, so you can happen to join one of our calls to ask us any questions. So we make ourselves super accessible in that way so the rest of our team doesn't ever feel like they can't find the answer they want.
B
And your normal workload like a regular week for you, what does it look like?
A
There's no real, like regular work week for me. We just do what is the most important thing of the day and we kind of go through that way. And so there's definitely no set thing. Like, I think the markers that are the same are the meetings where we talk strategy and we figure out, like, what we're going to do and if there's any changes we need to make to our understanding of how the business is running. And then we may have to deal with legal one week accounting, one week taxes. Like, it just updates and we just have to do whatever's the most important and time sensitive.
B
That's kind of what makes being an entrepreneur fun though, isn't it? That it's just always changing.
A
Yeah. So you can't. You don't get bored. I'll say. Like, there's never a day where we're like, oh, I'm so bored. But you know, there are weeks where you're like, I hate taxes. But you're like, but the nice thing about hating taxes is that the season is over. Like, you know what? I'm. There's like a kind of a finite amount of time that you suffer through each one of those things and then you move on to something else. So that makes it very palatable.
B
What do you wish that you had known before you started this? Seven years ago? So what have you learned the most about doing business or running a company or managing a team that you didn't know prior?
A
I would never want to Kind of tip off my past self, because I think learning all of those things happens for a reason. And you only learn by making mistakes. And so I don't ever regret my mistakes. But I will say I took a bad piece of advice early on when somebody had told me that, like, oh, your accountant doesn't really matter. And I was like, okay, I don't have to prioritize that so much. Right. Of all things, I'm like. In the beginning especially, I'm, like, taking everyone's. Everyone who's done it before. I'm, like, taking their advice much more literally. And then I realized that that was really not good advice to take, and it was a very costly mistake. And so that one I regret. But I think it's only through trial and error and working on things yourself that you realize who you can trust. It can be like you overall trust a person, but they can be biased about this or that. And then you just learn that over time.
B
And people love to give advice, even if it's not necessarily wanted.
A
Yeah. And people give biased advice, and you can't be like, well, they know so much better than me, so I'm gonna listen to them at 100. Like, I think you have to learn to listen to people at, like, 75, and then take what's useful to you and throw out what's not. And don't take anything personally and take.
B
Everything with a grain of salt, because their experience.
A
Yes.
B
Is probably.
A
It's different.
B
Very different to yours.
A
Yeah. And, you know, a lot of what you're going through is normal because it's gonna be normal the first time you do something that everything's super confusing. And just try to find mentors and other people and other sources of information to validate your experience, because you'll find it. If you really look for it, you'll find it. And finding a community where you can bounce ideas off of their people. Like, you know, when we were having a hard time hiring, quote, the right people, I'm like, why is this so hard? Is it just us? And people are like, oh, my God, we complain about this all the time. And so when you know that you're in the same boat, you're like, oh, okay, so I don't have to. On top of experience how hard this is, feel shame about it. You know, that makes it easier. So it's things like that.
B
I agree. A lot of what you learn, you kind of just have to learn by doing. You know, people listen to this podcast and they can get a lot of information from others. Who have done what they want to do before they're starting. Ultimately listening is a very different thing to doing.
A
Absolutely.
B
So how are you currently using AI in your business and do you have any concerns over the impact of AI on photography?
A
So the way that we're using AI right now is we use it a lot for content creation and just like pulling up a first draft of anything. So if we have like a blog post where like, hey, these are kind of the ideas that I have, it just helps you coagulate all of your ideas much faster and I love that. So across the board, like we do use it for a lot of writing just as like again a first draft, we'll always put our own spin on it afterwards. But like, like the first ideas and first research. Really great to have AI do that for us. No, I think our tech team also uses AI to help code some, some stuff and have shortcuts that way too. In terms of how I feel like AI is going to affect the photography industry, there's a lot of editing tools and other tools that help just some of the workflows for photography that we want to introduce our photographers to. Just so it, it saves time when they're doing the post production stuff. So like when they're actually photographing, like they have them and their camera and that's one experience. But then their stuff afterwards, whether it's culling, editing, whatever, there's a lot of AI that exists that helps them edit photos in their style much faster so they're not burning so much time in things that are very admin oriented. Those kinds of things we want to share with them for sure. And then in general, I just don't think that you can substitute real photography with AI photos. Now that's not to say there's some really great AI photos out there. So like, I think it's really great for some things like, like headshots if you don't really care. Like if you're, if you're like, I don't want to have to hire a professional photographer and there's actually a number of platforms where you can upload like 5 to 10 selfies and it comes up with a pretty photorealistic headshot, that's fine. But I feel like you would never want an AI generated photo of your family for Christmas where you're not in a real place. Like you want your actual family, does that mean like you want an actual memory? And so I feel like to that end I'm not concerned for what we do since we do portrait photography. It's about your relationships, it's about milestones. Do I think like AI could come in and take the same family and put them in a photo with like the Taj Mahal? Yeah, that's fine. Like I don't care. If you want that, that's fine. But like you still need at base the real photos of real people. That's I think, what people want.
B
Yeah, I think that people will want that for a long time. From how I've seen it and from photographers and videographers that I've spoken to, it seems like the custom style work where you're interfacing with another human is just not really going away.
A
Yeah.
B
Where do you see shoot going, say a year from now, two years from now, five years? Like what would you like to see for the trajectory of your company?
A
Yeah. So like, ideally I would love when people say like we should get photos taken of our family, that the first brand that comes to mind is Shoot with two T's. I want to be like the brand name that people think of when they think I want a trusted platform that gives me high quality, affordable photos that helps benefit local photographers. Like I want all that entire narrative to be in the concept of when they think about shoot. And so, you know, we want to definitely grow our brand in the us so many people still don't even know that we even exist. And so there's so many families out there and we want to just have more market share in that way. And then I think, you know, looking longer term out, we want to figure out how to be international. So expanding first to English speaking countries so it's easier for our customer service team like Canada, Australia, New Zealand, England, all that fun stuff. Like I think we would love to be able to expand our footprint that way because I think our technology and our platform can support that. And also creating more robust solutions for the photographers and also like better bundles for our clients so they get photos and they can get whatever photo products they want with that. I think we just want the entire universe to be a little tighter and better.
B
What about the talent that you bring in? How do you decide who gets to be on the platform and who doesn't?
A
So we have a really rigorous screening process so people apply on our website and we look at their portfolio first and we also look at their equipment. We need to make sure that their equipment is of a certain quality and level where it's going to create high enough megapixels so that if people want to blow up their photos and really enlarge them that it doesn't lose quality. So that's kind of the first order of business. We look at their portfolio to see, hey, from the photos that they're generating and showing me, do they look like they can photograph in the style that we currently have our photos looking like on our website and our Instagram? Because that's why people book us. And then if they pass that, then we invite them for a video interview. We interview them to make sure that they have the technical skills, the personality as well. Because having your photos taken is inherently a very vulnerable process and a lot of people are not models. They don't know how to pose. So having someone really be able to dictate that and make people feel comfortable and make people feel feel seen and confident, we want to see that that person understands that that's part of being a photographer. Right. So that's also a part of it. If they pass that stage, then we go on to having a test shoot where we have them do a trial Test shoot over 10 minutes to see if they can photograph in our style. Like what kind of variety can you do in a 10 minute session? Because our sessions are 30 minutes. So it's kind of like a slice of that. Once we decide that they should join our team, we then do a background check and then we onboard them and then they, you know, they take a test, they understand our policies, they join our team. So it's a lot of different steps to make sure we have the right people on the team.
B
And how many photographers do you have on your team now?
A
Yeah, we have like a little north of 750 right now.
B
Oh my gosh.
A
Across the U.S. yeah.
B
Have you had anybody discontinue because their photography brand is growing independently and so they, yeah, they tend to focus on that.
A
Yeah, we've had cases where people have stayed for the seven years that we've been in existence and we've had people who feel like they graduate and we fully welcome everyone at every stage. Like, we don't take it personally. We are here to support you. So if that means that you're like, hey, my wedding photography business is taking off and I don't want to be in your platform anymore. We're like, we're sad, but go ahead, fully support you if you ever want to come back, we're always here for you. And then we've had other people leave for other things. Like we. One of my favorite photographers was a great photographer, but really wanted to grow his tattoo business. So he used us to make enough money to start his tattoo business and now he tattoos most of his time. And I love that for him. We just want to be a really reliable source of supplemental income for people who are talented photographers.
B
This is such a unique business model that serves a very niche need. Whether you're using it as a stepping stone to a different business or need supplemental income, it is a very unique business model. So. So just to wrap this up, what life wisdom would you give to somebody who is coming out of college right now?
A
My life wisdom is that you should get as much experience as possible. And I say that because there's been this trend where people are like, get paid what you're worth. And I agree with that. But I think asking for that too early kind of cuts you off at the knees. Like, you need to make sure that you are coming in as leveraged as possible. Meaning, like, I remember I would do work for free. I would do work as an intern, I would do all types of things just so I could learn. So that when it came time to contribute, I was really confident about what I could contribute and how. Because like, no one can take your confidence away from you and your confidence comes from competence. One of the things I really promote is having a broad based experience. That's what I had, right? I did investment banking, I. I planned weddings, I whitened teeth, I tutored, I also produced a documentary, I did corporate. Like, I did all of those things. And it. And when you're older, it helps you synthesize information in a strategic and creative way that other people can't because they only ever did one thing. So all of a sudden their ability to contextualize different systems and processes is much more limited. So that's my personal advice for people maybe a little more like me. I didn't always know what I was really good at, but I knew that I loved working on problems, solving them, making order out of chaos, and the ability to synthesize all these different things and look at it together and be like, no, these are the priorities that we need to look at. This is how we solve this problem. That skill not everyone has, and that comes from getting as much experience as you can in all different types of ways.
B
I think that is really good advice. That is such good advice and so relevant for today. It's just there's been a cultural shift where maybe the expectation is that the time shouldn't be given away for free, but when you give your time away for free, you're not really giving it away for free because you're learning something in the process.
A
Yes. So I think the mistake is thinking that you're only valued by a dollar, like a dollar amount. And I would say that that's just like really not true. Right. Being able to learn something. Normally you have to pay to learn something. Right? And, and like you're learning something and you're learning something in context. You're learning how to practice it, you're learning how it works. I know that people are afraid of being taken advantage of and not getting paid what they're worth, but like, when you don't know a lot of stuff, you, you can't contextualize things and so you're not as effective. Whereas like I can hear different people say things to me and I can, I can understand where they're coming from a lot faster because I understand the 10 different ways of looking at something, if that makes sense and what might pertain to them. So it's about, it's about that kind of like you can, you know what I mean?
B
Well, and it's not like you're, it's not like you're working free forever. You may have a full time job, but then after your job you might go and pick up some experience that you are doing for free just so that you can broaden your options for later on.
A
Yeah, and I've had a lot of experiences where I or I started underpaid and I was like, I know I'm really underpaid, but let me see what happens when I do a rock star job for them. So I go in, I do the base what they want, and then they are like, oh, you're really good at this. And then I'm like, hey, I kind of want double what I was paid. Usually people will give it to me because they're like, I am so reliant on you, or I trust you so much that I can see that you're actually worth that. So whatever you think your value is, you have to agree on that. You can't go in and be like, I think I'm worth a hundred dollars an hour. And they're like, I don't even know you. That's insane. Do you know what I'm saying? Like, I don't care what your degree is. I've, I've met people that have really crazy degrees that are, can't do certain things right. So we have to agree on my value. I'm going to prove it to you. I'm going to show you that like I can respect the way that you work and people will just generally give it to you because they trust you.
B
Yeah. Prove it first.
A
Yes.
B
And then earn the right to get that promotion or get that raise or get paid more because now they already know that they're not taking a gamble on you.
A
Yeah. I've never been told no when I've asked. Like, there's always like this. Yes, you deserve that. And then you also know you're working for the right people because if you think you've proven your work and they're like, now, then I'm like, oh, I don't want to work for you because my upside is limited. Because I'm giving you my best and you don't appreciate that. It's almost. It's like a dating relationship. Everyone should appreciate each other on the same level.
B
Yeah. This is real wisdom. Anybody that's listening in, please listen to what Jen is saying. Jen, thank you so much for coming on and sharing your business model with us. The very innovative approach that you're taking. Love the way that you think, and I really appreciate your time.
A
Yeah, thank you so much for having me. It's been an honor.
B
Today's key takeaways. Build win, win, win models. Start noticing problems. In figuring out a business model that solves a problem for a certain subset of the population, many creatives avoid the business side of their work, which leaves wide open opportunities for entrepreneurs who can bridge that gap. Start small and prove your mvp. Stay scrappy. Test your idea within your own circle to validate demand. Before scaling. Make sure you forecast your cash flow. Low margin. High volume models can look great on paper, but if you don't forecast cash flow properly, they can sink you. Make sure your operations and pricing support the pace you're aiming for. Make sure to watch your marketing expenses like a hawk. Run lean tests, look at each platform and make sure you know what your ROI is. And if you can't track what's happening with your dollars, try other avenues. Having a remote team can save significant dollars, but comes with other challenges. Removing overhead expenses for office space can help you reach profitability sooner. But one or two days a month in the office with your full team could be highly beneficial. Manage your team with emotional intelligence. How you give feedback can make or break members of your team. It's about knowing how people hear things, not just what you say. Not everyone has experience receiving constructive criticism, so try and see people as the people they are and understand what motivates them. Some people are motivated by understanding all of the steps in the process, while others need to understand the why behind the steps. Every person is an individual and as a leader, you have to figure out how to problem solve together as a team and how to motivate people to want to do what it is that you want them to do. The corporate world can provide more stability and benefits, but sometimes the work can feel boring, unrewarding and feel like your efforts have little impact. Entrepreneurship can be more exciting. Every day has a new challenge, but stability isn't usually immediate. If you like your health benefits, free coffees and need stability, working in corporate America may be a better fit. Learn some basic business finance and accounting. Being spreadsheet literate and being able to create financial projections is really helpful when starting a business. Numbers are like a language. The same goes for business writing and understanding how to craft a professional email that connects whether it's to partners or clients, this style of communication is handy. Advice is biased, so trust your judgment. Learn to take advice at 75%, not 100%. Find a like minded community meaning if you're a small business owner, build connections with other small business owners, whether in your niche or in your local area. Being able to bounce ideas and lament on similar problems can provide emotional support and also help you solve problems. This next key takeaway seems like common knowledge now, but I'll say it anyway. Use AI as a force multiplier. If you aren't, your competitors likely are and you'll get left behind because they'll be able to achieve more work faster and for less expense. So if you haven't yet started, jump in and learn how Experience is worth more than early pay. Get as much experience as possible. Your confidence comes from competence and your value becomes undeniable when you've earned trust through results. So accumulate skills and be willing to forego the pay a little bit. When you learn something and experience something new, you might also learn something about yourself. Don't get so hung up on maximizing the value of your hour when you're starting out, because this can actually hinder your growth. So you may feel like you're starting out strong but then get cut off in your trajectory. Instead, get a broad base of experience and in all different types of ways. Don't just value your time by a dollar amount. You know that education usually costs money, so if you're learning, there's value. If you want to increase your pay, try this first. Go above and beyond to deliver more than what you're being paid to do. Prove you're worth more, then go in and ask for more. Once you've established that trust of your work ethic, you and your employer need to agree on your value with matched appreciation. So if you're proving your worth yet your upside is limited, perhaps you're in the wrong job. That's it for today. I release episodes once a week, so come back and check it out. Have a great day.
Summary of Episode: "Jennifer Tsay - Free Photo Shoots to $9M Revenue: The Surprising Business Model of SHOOTT"
In this compelling episode of How I Built My Small Business, host Anne McGinty sits down with Jennifer Tsay, the co-founder and CEO of SHOOTT. Together, they delve deep into the innovative business model that catapulted SHOOTT from offering free photo shoots to generating over $9 million in revenue within seven years. Jennifer shares her entrepreneurial journey, the challenges faced, the strategies employed, and the invaluable lessons learned along the way.
Jennifer begins by providing a glimpse into her diverse professional background. Growing up in Allentown, Pennsylvania, she spent 20 years in the New York area, navigating through various industries including investment banking, corporate finance, nonprofit work, and the creative sector as an actor and producer.
Notable Quote:
“I produced a documentary, took acting and writing classes, and was an actor for over a decade. That’s how I ventured into the creative world.”
[02:20]
Her transition from the corporate realm to the creative industry laid the foundation for her entrepreneurial spirit, ultimately leading her to identify and address gaps within the gig economy for artists.
The inception of SHOOTT stems from Jennifer’s desire to create a sustainable business model that supports artists, particularly photographers, in the gig economy. Observing the struggles of actors in securing consistent work, she pivoted to photography, recognizing its potential for aggregating demand.
Notable Quote:
“Shoot came about because I wanted to figure out a business model that solved the gig economy for a certain subset of artists so that they could stay artists.”
[03:01]
By positioning photographers in fixed locations for specified time frames, SHOOTT ensures a steady stream of clients, thereby amplifying demand and providing photographers with reliable income sources.
Jennifer and her team initiated SHOOTT with a Minimum Viable Product (MVP) approach in New York. They launched rudimentary websites and advertised free sessions where clients only paid for the photos they desired.
Notable Quote:
“We trialed it with our own community and realized there was enough demand. That was really exciting.”
[04:25]
This initial testing phase was crucial in validating the business model, leading to the development of proprietary systems and scaling operations.
Achieving profitability was a significant milestone for SHOOTT, reached five years into operations. Jennifer emphasizes the importance of balancing pricing, advertising costs, and client volume to ensure financial health.
Notable Quote:
“It took us five years to become profitable. We hit break even in 2023 and 20x that profitability in 2024.”
[05:10]
This disciplined approach to financial management enabled SHOOTT to sustain and accelerate its growth, expanding services to over 60 cities across the U.S.
SHOOTT’s business model is designed to benefit the company, photographers, and clients simultaneously. By offering free photo shoots where clients pay only for desired photos, SHOOTT attracts a broad customer base while ensuring photographers earn a minimum guaranteed income per session.
Notable Quote:
“We have a 100% minimum guarantee per shooting hour, so photographers are making money no matter what clients pay.”
[06:22]
Clients enjoy affordable, high-quality photography sessions, many of whom are booking professional photographers for the first time. This approach not only creates new demand but also empowers photographers to focus solely on their craft without the hassles of client management and marketing.
Operating a high-volume business model entails managing significant marketing expenses and seasonal demand fluctuations. Jennifer discusses the necessity of effective digital marketing strategies and constant optimization to attract and retain clients.
Notable Quote:
“Marketing is a huge part of it because we have to really balance getting enough clients for them and optimizing what does it cost to get them.”
[10:12]
SHOOTT employs a combination of in-house marketing and external agencies, utilizing platforms like Facebook and Google, which have proven to be the most effective. Additionally, they experiment with emerging channels like connected TV to diversify their marketing portfolio.
With a fully remote team comprising 12 full-time and six part-time members, SHOOTT prioritizes clear communication and emotional intelligence. Jennifer emphasizes the importance of understanding individual team members’ motivations and tailoring feedback accordingly.
Notable Quote:
“Managing your team with emotional intelligence… it’s about knowing how people hear things, not just what you say.”
[19:36]
Regular meetings, email updates, and open-door policies ensure that the team stays aligned and productive despite the geographical dispersion. Jennifer acknowledges the challenges of remote management but highlights the importance of purposeful communication to maintain cohesion.
Jennifer candidly shares the lessons she’s learned over seven years of entrepreneurship. One pivotal mistake was undervaluing the role of an accountant, leading to costly repercussions. She advises aspiring entrepreneurs to critically assess advice and trust their judgment.
Notable Quote:
“Advice is biased, so trust your judgment. Learn to take advice at 75%, not 100%.”
[27:45]
She advocates for accumulating diverse experiences, highlighting how her varied background has enhanced her problem-solving and strategic thinking capabilities.
SHOOTT incorporates AI primarily for content creation and streamlining operational tasks. Jennifer views AI as a tool that complements human creativity, particularly in post-production editing, but remains confident that authentic photography retains its unique value.
Notable Quote:
“I don’t think you can substitute real photography with AI photos… people still want actual memories.”
[29:15]
Looking ahead, SHOOTT aims to expand internationally to English-speaking countries and enhance their offerings with more robust solutions for photographers and clients alike.
Maintaining high-quality standards is paramount for SHOOTT. Their rigorous screening process assesses photographers’ portfolios, technical skills, and interpersonal abilities to ensure they align with SHOOTT’s brand and client expectations.
Notable Quote:
“We have a really rigorous screening process… we want to see that person understands that that’s part of being a photographer.”
[33:06]
Despite some photographers moving on to grow their independent businesses, SHOOTT remains supportive, viewing departures as natural progressions and opportunities for alumni to thrive independently.
Jennifer imparts invaluable advice to recent graduates and aspiring entrepreneurs. She underscores the importance of gaining diverse experiences, building confidence through competence, and valuing learning over immediate financial rewards.
Notable Quote:
“Experience is worth more than early pay. Get as much experience as possible.”
[36:01]
Jennifer encourages young professionals to embrace opportunities for growth, even if they come with humble beginnings, as these experiences lay the groundwork for future success.
Anne concludes the episode by summarizing the essential lessons shared by Jennifer:
This episode offers a profound exploration of how innovative business models, coupled with strategic management and a focus on community, can drive substantial growth and create lasting impact. Jennifer Tsay’s insights provide aspiring entrepreneurs with a blueprint for building a resilient and profitable business in today’s dynamic market landscape.