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Dr. Lindy Ledohowski on Imposter Syndrome & Running a Tech Company - The ROI Online Podcast Ep. 31

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On this episode of the ROI Online Podcast, Dr. Lindy Ledohowski shares the challenges she faced in transitioning from a professor to the CEO of a tech company—and how that transition has transformed her personal identity.

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Running a tech company can be a challenge. Running a tech company when you don't have experience operating a business? Even more so.


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Lindy Ledohowski has always struggled with something many of us relate to: imposter syndrome. Even after receiving a 5 on her Advanced Placement assessment for English (the highest score possible), she still found herself wrestling with insecurities. She went on to pursue a master’s degree in English, but that feeling never quite went away. 

While going through school, she decided to get a job she knew she would enjoy more than bartending. She worked as a high school English teacher, where she discovered her passion for teaching others. Along the way, she discovered a hole in the education system: No one teaches kids how to learn. As a result, they turn to memorization. 

Memorization and learning are two very different things. Even if they manage to score good grades, students find themselves struggling to get through college or losing the knowledge they fought to retain for finals. They never truly master the skills they need to reach their full potential. 

One night, she and her husband shared their frustrations about how no one teaches students how to learn. Then the thought hit her. Why didn’t they spark the change? It was the perfect way to push themselves while addressing this overlooked gap in the education system.

Lindy and her husband started a software company focused on writing, EssayJack. While it may have started off as a hobby/side project, it quickly became their primary business. She began to see herself as a business owner, not just a professor or a writer suffering from imposter syndrome.

Lindy has had to deal with the world of sales, customer support, and all the details that go into running a SAS company. The transition has been far from easy but has left her with a new appreciation for being a business owner and a deeper understanding of what it means to teach.

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You can learn more about Lindy here:

www.essayjack.com
Twitter: @doctorlindy
Facebook: @Essay Jack
Instagram: @doctorlindy

Read Lindy’s book:

Unbound: Ukrainian Canadians Writing Home

Get your copy Steve Brown’s book, The Golden Toilet. Also available on Audible for free when you sign up for a 30-Day Trial Membership!


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Topics: Marketing, Podcasts

Lindy Ledohowski : 

Know, you are smart, and we can help you to build your confidence. We can it's not rocket science, we can decode things for you like you got this, we want you to feel confident, we want you to feel that you're not alone. We want you to feel that you can do this, all of those sorts of things are the kinds of feelings that you want. So that now we've got, you know, when when students use sa jack, they say things like, Oh my gosh, it helped me to feel smarter. You know, and that's what you so, you know, that's the feeling that is a marketing or branding feeling as opposed to them going into. It helped me to articulate my ideas and as persuasive away as possible, you know, even though that that's ultimately what it's doing.

Steve Brown : 

Right?

Lindy Ledohowski : 

It's them feel smarter, it makes them feel confident, or it makes them feel that this task, the scholarly task is something that they can do.

Steve Brown : 

Hi, everybody. Welcome to the ROI online podcast where we believe you, the courageous entrepreneur. of our day are the invisible heroes of our economy. You not only improve our world with your ideas, your grit and your passion, but you make our world better. I'm Steve Brown. And this is a place where we have great conversations with winners just like you while we laugh and learn together. So Dr. Lindy letta hausky Welcome to the ROI online podcast. I'm going to introduce you But first, I need to confess something to you. Okay. One of the most. I just remember that one of the most embarrassing moments of my educational career was right out of high school and my first composition class when the teacher handed me back my paper and it had so much red marking on it, that I felt compelled an odor or a red pin But it was in an embarrassing realization that I was the worst at writing composition. I didn't know what I was doing. And I just felt like such a loser. And getting that paper back was a confirmation about

Lindy Ledohowski : 

Oh, no,

Steve Brown : 

I felt and so when I learned that you have a company that you're the CEO of sa jack Incorporated, and at first I was going s s a, what is s stand for? And then I realized, oh, that essay, jack. And Had I known about this. I could have had more self esteem probably would have gotten more dates. And I'm the teachers wouldn't have been like looking at me askance. Every time I walked by, why is he even enrolled, he should go and learn like my mom used to say, you want to grow up and dig ditches. is like, here's your confirmation.

Lindy Ledohowski : 

Well, I love that anecdote, Steve. And I mean, okay, nowadays we don't use red pen so much. Because exactly, it can be very discouraging. Whereas feedback is all part of the writing process. But But yeah, I mean, you're, you're, you're certainly not alone with that sort of initial like, Oh my god, I didn't know what I didn't know. And now my heart is broken when it comes to writing at a particularly, you know, college or university when, you know, the expectations differ. So yeah, that that, you know, in a nutshell, that's kind of some of the kernel bits of why we started sa jack in the first place.

Steve Brown : 

Yeah, I love your your story. So somewhere along the way, you, you found out you enjoyed writing them. So that was the first indication you were weird, right? Yeah.

Lindy Ledohowski : 

Yeah, absolutely. And I think they made probably Not the first like, I'm sure my parents would be able to tell some stories of even pre writing Lindy, which, where they were like, well, this kid is a bit weird, but definitely, I mean, I was I was one of those, those kids who is writing stories, like, you know, I think my first story I wrote in grade one and it was, you know, I had heard that this notion of like a deserted island, and of course in my six year old brain that became a desert island. So my first story was about an island that was a desert island and it was covered with candies and chocolates and all the rest of it so so yes, I was weird from the get go.

Steve Brown : 

I loved that. I always thought they were hysterical markers as we were traveling down until I realized later after I started paying attention. Oh, historical.

Lindy Ledohowski : 

Yeah. Sometimes they can be quite hysterical. But

Steve Brown : 

you know, you write you believe if we have mastery over the written word, then we have mastery over the world. What Why Why do you say that?

Lindy Ledohowski : 

Yeah, thank you because that is really like one of those things that I sort of deeply and truly believe and i think that you know, if we can name things, if we can understand things then we can respond reasonably to them. So for instance, if I can appropriately name a feeling so if I if I'm feeling upset and I'm like I'm upset, but am I angry upset? Am I sad upset, am I hurt upset, you know, there there are all of these kinds of nuances to naming things and understanding things and the closer we get the better than we we can control ourselves and the world around us and feel a bit empowered. So if I can, I'm just kind of feeling upset. If I can then go Oh, actually, like I'm, I'm hurt upset because I got all this red marking on my very first essay at yesterday, and it's now sort of destroyed my confidence and I feel a bit hurt and I feel a bit embarrassed. Tonight, I'm not sure what to do next, that's very different than like, I'm upset and my teacher is an idiot and I need to go see her car, you know, and so I so I really do think that language is the way in which we can, we can start to make sense of what is otherwise a very confusing world. And then, you know, in my case, that sort of love of language and the way in which I think it can be a really empowering vehicle, finds its expression in the written word. So, you know, some people may still be communicating with words and language but but maybe it's with song or maybe it's even, you know, running a podcast where you interview people and then you have conversations. And and for me, it's, it's the written word and so so that's really I really do think that if you can give people the tools to write well, then then they can achieve whatever it is that their their dreams might be.

Steve Brown : 

So when did as a kid or as a student, when did it pop into your head that you started to see yourself is, hmm, I'm kind of good at this. I am. I like this.

Lindy Ledohowski : 

Haha. You know what, like, when that happens, I'll let you know. I mean, I think I think a lot of people and I'm going to be I am going to admit this because because this might actually apply to some of your listeners to think we all feel a bit of the imposter syndrome and we all kind of think other people are better at it than than we are. And so, you know, when I was a high school English student, you know, we all take our sort of literature classes in high school and I thought, like, I knew I liked reading books, but I like to read about like dragons and adventures and you know, whatever, not not the things that were necessarily communicated to me as like have high literary value when I was a teenager. And so I thought, you know, okay, I'm okay in English class, but you know, there there are, you know, the people in the class who tend to describe what's happening in the poem really well, and they seem to, like have that key. And I'm sort of going, Oh, really, that the poem was about death and rebirth. I thought it was about a bird, you know. And, and so I really didn't know. And then it turned out, and I was, I scored very well, I was taking Advanced Placement ingression advanced placement is a set of exams, it's run by the College Board. And in the final year, you you take an external exam, so it's not marked by your teacher, it's marked by a group of people. And there's a scale out of five, so five is the top and then for debt, you know, three is a pass. And if you score five most universities in North America, so in Canada and the US, they'll accept that for university credit, some will even accept a grade of a four at a university credit. So I'd written my exam, of course, imposter syndrome. I thought I did horribly. I was like, whatever, it's out of my head, it's done. You know, and then it was months later. So I hit sort of graduated and the mail came in. And this is back in the days of snail mail. So my mom comes home Monday, there's mail for us, I opened up my my letter from the AP College Board. And I had scored a five. And I remember, I was dumbfounded. I sat down on the kitchen floor and my mom costume. What kind of, you know, devastating news Did you get like, did you fail, and you're, you know, you got the red mark for the red marking everywhere. And so that was probably the first at least external validation, that maybe I could do this. And then, you know, as I as I've gone on at every step of the way, you know, I did an honors English degree, and I did an education degree, and I did a masters and they did a PhD, and I did a postdoc and I became a professor and wrote a book and you know, those and at each step, I still thought I was a loser who didn't know what she was doing. I started a business focused on writing, I still wake up thinking I'm a loser, and I don't know what I'm doing. And so all of that is is a very long answer to say. I don't know that any one gets the moment where they're like, actually, yeah, I'm, I'm good at this. And I should keep going. You may have those moments, where it's like, Yeah, wow, that was great. And then you may have the moments like, I'm an idiot, I need to do something else. And I think it's just a matter of kind of plodding forward and not not getting too high at those great moments and not getting too low at that at the down moments. And you can kind of chart your pathway through at least that's that's kind of my take so far.

Steve Brown : 

So you become a teacher. And I see a lot of teachers they do it because they not only want to just get a job, pay the bills, but they're wanting to add value to some some bodies life and a way so you become a teacher and you do that for a while and then you become a teacher of teachers. And you teach them how to teach.

Lindy Ledohowski : 

Yeah.

Steve Brown : 

Walk us through that. Hello.

Lindy Ledohowski : 

Um, so when I was doing that, that undergraduate degree In English, so I was also very mindful of like, you know, at some point, you've got to get a job. So I waitress throughout my undergrad degree and sort of paid the bills and collected tips. And I sort of thought, well, I need to do something else. So that you know, at least now I know I can always waitress, so the world is filled with, with places I could work and I can be a waitress so that I will always be employable. Of course back then I couldn't have imagined COVID where things get shut down, but back back in right there there were always going to be places for people who could waitress then I was like, Okay, well and if I want to build up on Okay, maybe I should train to be a teacher. So then that was really the motivation like okay, I've got an English degree. Let's do it. I know in the US, I think you could teach high school simply with a first degree in Canada, you need a second degree, so a Bachelor of Education. So I went and qualified and did my Bachelor of Education and then I taught high school English and I really liked teaching high school English. So that Now my first full time job as a high school teacher was 20 years ago this year, I'm still in touch with some of the girls. It was an all girl school with some of the girls I taught back 20 years ago. So that goes to show you that, you know, I liked it. And they seemingly, you know, like me, maybe it was the fact that I didn't use too much red pen. You know, so that was that was good we got along was really great. And then, for me, I really thought, well, I want to challenge myself more. So, as my high school students were graduating and going on to university, I actually felt myself being quite envious of them. You know, they were going off to interesting universities to study new things. And I thought, Oh, this is quite a warning sign. If as a teacher, I'm jealous of these 18 year old kids going off to start their university career. I think I might have more University in me that I need to kind of work my way out because otherwise I'm going to be here as a teacher, and I like them and I like teaching But as time goes by, I'm going to get more and more jealous and more jaded. And then, you know, that's not good for anybody. So then, and it was quite I remember what I saw, I applied to do my Master's in English. And I remember what I got accepted. And then I had to come and tell my, my grade 10 homeroom class that I wouldn't be there next year that I was giving in my notice, and actually got teary and cried and everything. So um, so I did quite like teaching high school then I went off and did graduate work. And as a Masters and PhD student, I also taught writing at the university level and taught teachers how to teach, as you say, and I really liked that kind of give and take and seeing people learn how to learn and seeing people learn how to awaken learning and other people. So I really like to facilitate that process. You know, I really think that there's something very empowering about that. So when people start to see like, Hey, I can learn how to learn or You know, it's not just about opening my brain and having content dumped in that I memorize, but they're like these tricks and tools and things that I can do and, and I can get better at something and with practice, I can get better at this other thing. And so I quite like that and again, you know, got a job as a full time, English professor and that and I and that was an years ago, 11 years ago, 10 years ago. And, and again, we love teaching those students It was really you know, I had really great undergraduate students, you know, had some doctoral students I worked with smart, interesting, capable people. And it was out of that experience really, that the the seed was planted for what has now become, SAE jack. And so largely it was in these University classrooms where I'd have smart, interesting students, and they'd say things in class and be like, Oh, fantastic start.

Steve Brown : 

get jealous.

Lindy Ledohowski : 

Yeah, no I wasn't jealous. I was happy for them. So this was great. This was a win win. I wasn't jealous. They were smart. But then they submit those written assignments and I'm like oh my goodness. I know you're capable of so much more. And somehow you've not been taught the foundational stuff, right? And so I used to think it was like, if you show up to first year calculus, but you can't add and subtract, you know, your professor still has to trundle forward with teaching calculus, and you have to figure out how to fill in those gaps. And so in, say, a first year English class, I have, you know, I was teaching five novels and you know, so I couldn't stop and be like, okay, we gotta, you know, break this down and teach basic, you know, you know, persuasive argumentation and scholarly writing. And so I started to see like, well, then I started because I'm a big nerd. Obviously, I started to sort of do some research into like, Well, why is it that people aren't prepared? Especially because in the university often there's this like professors that around biller who knows In high school, high school teachers are terrible. And, you know, I was a high school teacher, I wasn't terrible. Like, I don't think that's the problem. I mean, there. And then I started to as I say, I was a big nerd. So I started kind of research, like, why do you know, people run into this, this issue? And, and there are lots of complicated reasons. And I mean, yeah, sure, in some cases, it can be a bad high school experience, in some cases, like there's all kinds of systemic sort of reasons as to what's happening in the home access to, you know, parents and families who have familiarity with post secondary education, then, you know, if you've got international students and they may have been top of the top in an entirely different education system, where the expectations were different and then they find themselves saying Canada or the US were you expected pull different set of things. They're like, No, but I was really good at the memorization and give you stuff back. Right? And now you want something else for me, you know, so and so it was out of that, but I thought, Okay, well, you know, let's let's see if we can get software to kind of play in this and provide some help. So that's, you know, a very long answer to a good question about that journey from sort of teaching at the high school level, and then right up through through university to now running a software company.

Steve Brown : 

Yeah. So let's, let's go there. What in the world gave you the idea that you could start a software as a service company? That's a tough competitive, and so you weren't like watching Shark Tank or something in that. I'm jealous. I could do that. Or, wow. Where did that come from? And why? Why would you even believe you could do that?

Lindy Ledohowski : 

Yeah, you know what? It temporary insanity. Probably. Yeah, I can't answer. But I mean, realistically, it was. You know, I don't think we really thought of it as a business at first as my husband and I who started the company? But at the beginning, we really started what we thought was a product. It was like, well, let's create the thing we wished our students had. And it was only by sort of create, and that, you know, we, you know, hired a software developer out of our savings account and sort of paid him to build, like, we literally cut up pieces of paper, and sort of moved it around across the table to be like, and then you would click here, and it would move this way in that way. And that was how he described it sort of being the non coders, ourselves. And the guy that we found to sort of build us the prototype, he's like, yeah, I kind of see what you're doing. Okay, I'll go off and build that. And so then when we had a thing that works better than the cut pieces of paper moving around on the table, and we started to show it to students and teachers and professors, and, you know, we did a whole bunch of sort of testing with that first early thing and everybody loved it. And nobody had seen anything like it. And this was like from grade eight to university, you know, hundred Have people that we were showing it to in that very early stage were like, Yes, I want this like, Okay, let's go take a little bit more of our savings and see if we can build something that's a little bit better than just this kind of really rough. And so so we did that not I mean, it took maybe nine months. And then we said, okay, well, now we've got a thing, let's, let's see if anybody will pay for this thing. And so we launched it, and we sort of tagged on a pay gateway for subscriptions. And you know, within three weeks, we had our first paying customer who just sort of randomly come to the website, tried it, loved it. And so it was at that point that we started to realize all of the complexities of a software business. So the thing like again, as I say, we were really focused on the product. So we thought, Okay, well, you use your savings, you build a thing, then the thing is built, and people like it or not, I had no idea that, you know, browsers were continually being updated. And so you would need to have continual tech work at the basic level just to make sure that you're solving Work continued to be compatible with the upgraded and changes to the browser, something as simple as that, let alone all of the different coding languages that you use, which are currently on consistently being upgraded. Then as well the notion that once you have a product and that you're asking people to pay, you do kind of need some customer support, and like, helpdesk, and you know, all those sorts of things. And so it was, as we were then trying to backstop and fill in that we started to really think about the business side of things. So in our case, the product came first and then it really kind of drove the ship. And now we've been building in the business to support the product. And so now I can say, you know, I am the CEO of an edtech business, but in the early days I was just like I don't know I created a product.

Steve Brown : 

So your your self identity changed from that and being a teacher you're also an author, you wrote him a book by the way, we need to mention but but you You change the way you saw yourself. And now you see yourself differently talk about that transformation and how you maybe you, you struggled with that, or maybe it was easy for you? I don't know. No,

Lindy Ledohowski : 

no, it wasn't it wasn't easy, Steve, that's a really good question. And I think a ton of people will will identify with this, like, our professional identities become so enmeshed with our self esteem, our sense of ourselves in the world or whatever. And so, it was very easy when I could walk around in the world and be like, I am a professor, that is my identity, and even simple things like you know, when you fly someplace, and you have to fill out the customs form and it asks you for your occupation. Bring down professor. That's the thing that makes sense. And I was Yeah, like I was very, sort of, Okay, that's, that's who I am. And I published scholarship. I am a scholar, you know, all the things I was, I was starting to feel quite comfortable about But with as part of my identity, and then I quit my job as a professor before essay jack was really like had legs and was really a thing. And so there was that intermediate time where it was like I am a person frenzies thinking about a thing and you know, and that was really hard. And then even once, you know, we had, we had, say, jack is a product and market and we were growing in and all the rest, I think I was still very resistant to identifying with myself as being an entrepreneur. So as an academic what, you know, your social media, people, you know, like, they're all academics too. And you and you share book recommendations, and you talk about like, Oh, it's the time of year where we have to mark essays, and everybody complains about all that. And I had sort of, I was still in that world. And every now and then when you know on Twitter or whatever, you know, entrepreneurs The startup world VC world and all that would post things. I kind of poo pooed it like I think I, you know, now I can say I, at the time, I didn't know this, but I think I probably was a little bit up on myself. I think I was like, you know, I'm an academic and you know, these lowly investor, VC, crass entrepreneurial types, or whatever it is that, you know, was was was in my head, as I say, I needed to name it in order to kind of come to terms with it. I hadn't named it I was just sort of, I think, kind of looking down my nose at these sort of crass commercial, blah, blah, blah, whatever that sort of package of ideas was. And it was only once I started to be like, okay, no, no justice, you threw yourself in with both feet into being an academic and a professor and you took it seriously and you published and you know, you now are in this other place. So you have to jump in with both feet you need the people that you're engaging with, whether it's on social media, the conferences, you go to the thought leaders you're interested in, it needs to be within the entrepreneurial space. You'll and you'll find your place in that like so. So as an academic and English scholarship, you know, I can find my, my folks who do the things that I used to do as an academic sounds like so you have to put in that same amount of work to find the types of entrepreneurial communities that work for you. But you do have to take it seriously. And so that wasn't an easy transit. I think I've made it now. Like now, particularly, I find, I take a great degree of pride in being involved in a number of organizations that focus on sort of women led initiatives. So, you know, we've got a number of women developers on the sajak team. And so there's a whole sort of network of like Girls Who Code and things like that. So dealing with sort of gender representation and equity. Finally, recognizing that actually, being a woman in business or running a women lead tech company is itself something that other people find valuable or interesting. And so as I say, that's one of the Kind of niches or areas where where I've found comfort in this new identity as tech entrepreneur. But yeah, it took a while.

Steve Brown : 

I want to pause here just for a moment and talk to you about a program that we have just released called the ROI quickstart Academy for authors every day, I talk to business owners just like you who struggle with quickly getting their fundamentals in place. We want to create a great foundation, and we want to grow our business, but the things that are in our way, our lack of knowledge about the specifics, we should put in place, what kind of technology what kind of messaging and what kind of campaigns and that problem exists for authors as well. And we just chill so good with authors because, well, I'm an author, and I understand everything that you struggle with. You have a great idea you have a great book, but what do you want to do? You want to get your book in front of more people If you want to make it easy for them to find you learn how they can schedule a time to talk with you hire you for a conference, or maybe sign up for the services that your book promotes. So what is the Quickstart Academy for authors? Imagine working with a small group of like minded authors, and the experts from the ROI quickstart team. It's a great way to get your messaging clear to be confident with the technology in your marketing automation, and how to run a strategic campaign to get you more of what you want from the investment of your book. To learn more about the Quickstart Academy for authors, you can visit ROI online.com or click in the link in the show notes below. And now, back to this episode. Yeah, I love that. So here you are. You're finally starting to go okay, I can I can see myself as one of these. These red printers that run businesses I can start to be that right? But then then you run into this thing called marketing and branding. And this other big hand that slaps you and makes you feel inferior. And you got to bring your writing game to there. Tell us about that.

Lindy Ledohowski : 

And you know, what's surprising is that, like, I thought I was a good writer, you know, I published scholarship as a writer, and, you know, I won award I yeah, I used to do running races and cycling races, and I have a sporting blog that people read. And so I was like, you know, I got this writing thing down. But your point there that like marketing and branding, they're very different than other types of expression. And so you kind of have to learn a different audience and a different set of expectations and So when you're writing in an academic context or for readership that is expecting certain conventions and those are the ones that I was really comfortable with, those are the ones that you know, say jack has a platform really decodes and provides you a system to work through with ease. But then I didn't have you know, the essay jack for marketing or the sock for branding, you know, that was very that was, that was a world that I kind of had to figure out on my own. And, and it was a bit hard. Because to go back to you know, your original point, like I'm a bit of a weirdo and so the way I see the world is different than the way than the way other people might see it. And so as a result of that, I learned, you know, you I couldn't use myself as the template from which to build expectation. So for example, to illustrate this, obviously, I'm very comfortable with text. I can read long emails I can read long but I none of that is overwhelming to me. And it took me a really long time to realize that that is not standard. So lots and lots of people will not read a long email will not read a long blog will are aren't interested by long chunks of unbroken text. And so that's fine. You have to know that and then you have to do the work to break down your messaging into small bite sized chunks. And then one of the other sort of ways in which I can illustrate this weird transition from being somebody who thought she knew about writing to somebody who had to learn about marketing and branding, that in academic writing, and even other forms of journalism, often you are making an argument. So you're trying to persuade your reader with evidence and you're trying as much as possible to be an objective authority over the content. So I will I will provide evidence from the text and maybe there's data or statistics or whatever, right whereas in in marketing and branding It's about feelings. So what do you want the people at the other end? Whoever your audience is, what do you want them to feel? And you are not going to make them feel anything if you're making a very objective persuasive case, you know, and and again, that took a while for me to realize that I can have all of the data and statistics about how essay DAC improves grades and essay deck reduces writing anxiety, and essay jack reduces the time it takes to complete an essay, all of that, and all that is good and persuasive. And obviously, it's important to know that your product does what you say it does. But people won't be convinced to try it. If that's your your marketing, you know, your marketing needs to sort of go where they are. So, in your example, that student who has submitted his first piece of writing at university get something back and is like, Oh my god, I'm an idiot. Why am I even here? I'm gonna go digging ditches.

Steve Brown : 

I'm still not over it.

Lindy Ledohowski : 

Exactly. So it's a it's like, No, no, no. You are smart, and we can help you to build your confidence. We can it's not rocket science, we can decode things for you, like you got this, we want you to feel confident, we want you to feel that you're not alone. We want you to feel that you can do this, all of those sorts of things are the kinds of feelings that you want. So that now we've got, you know, when when students use essay jack, they say things like, Oh my gosh, it helped me to feel smarter. You know, and that's what you so, you know, that's the feeling that is a marketing or branding feeling as opposed to them going, you know, it helps me to articulate my ideas and as persuasive away as possible, you know, even though that's, that's ultimately what it's doing. Right? It's them feel smarter, it makes them feel confident, or it makes them feel that this task, this scholarly task is something that they can do, you know, they're not alone. They, they, they have the tools to to master this and and so, you know, that from a marketing and branding perspective, like I it took me a while I mean it To be fair, it's still it's, we're still in this process of refining it and, and getting that messaging, right and realizing that, you know, you want to you want to live in the space of feelings, not in the space of reason, when it comes to marketing and branding, you know, obviously, that's a bit crass. But you know what I mean, right?

Steve Brown : 

It is, like, that sounds and typical to legitimate business process.

Lindy Ledohowski : 

Yeah. And, and, and you need to inform the feelings based messaging on the data and the stats, you need to figure out, you know, why do people use whatever your product is, you know, in our case, you know, we track you know, what features are more successful and who, what age grade age range and you know, things like that sort of figure out exactly who our best customer is. But then on the back of the data, you kind of like, Okay, what do you want to feel about your writing, you know, and that's something that that matters. And again, to go back to that commitment, I really do feel that You know, if you can master writing, you can feel empowered, you can feel that you have control over what can otherwise be a very overwhelming world in which we all live. And so that feeling of being empowered is also really, really important. I think

Steve Brown : 

it's huge. It's, I think it's one of the biggest competitive advantages of the leaders that we admire. They figured out how to communicate succinctly, to have declarations and beliefs to have these sayings and and the way that they tee it up, and walk it through and then put a little bow on the end of the right presentation or the conversation or whatever. It's beautiful. But what you're doing is you're helping students facilitate, there's a journey you have to go on and you have to learn it in writing. And putting those thoughts together and being able to, to work through them and then present them in a way that your peers can pick it up and then be pushed back a little bit and have a discussion. That's huge. Would I be correct to saying that you have teachers that, yeah, that suggest this or recommend this?

Lindy Ledohowski : 

Yeah. So we've got sort of, it's basically the sajak platform has kind of two ways in one is just the individual student and any student can go and sign up. And then we have an institutional extension, and that has a bunch of like educator functionality. So teachers can do things within within the sajak platform. So the way essay jack works that sort of breaks a writing task down into its component parts, so it's like smart templating. So if you have to write an essay, it breaks the essay down into small chunks. So what do you need in your opening sentence and it has tips and prompts and sentence starters. Okay, now you've got your opening sentence, you need a bit of background, what do you need in your background, you know, and it kind of walks you through so that you don't have that, like, blank page, right? You. So yeah, where to start? And so as an educator, what you can do is you can go in the into your dashboard and you can Customize everything entirely. So let's say you know the tips and prompts for the off the shelf essay jack, first sentence, maybe that's not what you say in your classroom, maybe in your classroom, instead of saying, you know, what's your topic jump right in. Maybe in my classroom, I say, you know, always hook your reader with an engaging first sentence. So if that's something that that I say, in my class, I can go in and customize the platform so that it will say that and my students will have my guidance with them whenever they're at home writing, or if they're in the library writing or on the subway, on their phone writing. You know, there's that kind of functionality. And then as well, as an educator so often, particularly in high school, one of the key things that you do as an educator is you you model the task that you want your students to learn. And so you often model, essay writing and so you can have, say, a smartboard or something, you know, and you can use the SA jack platform, to model the component parts. So you need your introduction. You need your body, you need your conclusion, okay, what goes in the introduction and you can sort of work through that in the class. And then the students actually have the platform to take home with them and to work on their own. Or if you're a school that has sort of one to one devices or something like that. So you're absolutely right. There's the you know, just come at it cold, and use all the off the shelf stuff if you're a student. And then there's the if you're an educator, this is how you can just recommend it to your students and be like, use the platform. Don't bring your bad writing to me, my red pen has no ink. Or you can say okay, actually, I'm going to use this platform to and use it as a teaching tool. So you've got that kind of double functionality.

Steve Brown : 

So talking to not Doctor lendy. But But business person then the app. Yeah. What's your biggest most embarrassing mistake you've made as a business person?

Lindy Ledohowski : 

Oh, goodness, me. I only have to have one. You know, to be honest, there are so many other I think so one of the big sort of errors that we made. So I'm very naive, broadly speaking, I'll sort of admit that. And it's taken me a while to realize that ultimately, like, so I've made sort of partnerships with other companies or you know, we had an investor who was going to invest, and you may have all those sort of legal language contracts and all the rest. But when push comes to shove, if somebody doesn't deliver, you know, there's not that much you can do about it, you know, so if you have a partner, and they've given you projections for how much they expect to sell, and they don't hit those targets, are you really, really going to sue them? You know, as a startup, you know, and in our case that, you know, the answer is, you know, and in those situations as we've had them know, we just kind of go Okay, well, I guess, lesson learned that wasn't the greatest partner and you kind of move on, but I think so. So what that means In terms of the biggest mistake is really truly believing that other people have their, you know, their most honest and best foot forward. And realistically, in business, there are lots and lots of people who may themselves be making mistakes, who may themselves be telling you a good story but but actually have no intention of follow through who may have competency issues in their company that you have no insight into. So there's a whole combination of just as there's a whole combination as to why some people show up at college or university and can't write, and you can't boil it down to one day. There are also a whole combination of reasons as to why partners or potential investors may not work out. But if you go in there thinking, well, all of my students can write or if you go in there and think, oh, all of these partners are going to deliver perfectly and don't build in some sort of contingencies in your planning then then that's probably a mistake. And so that's, that's certainly, you know, where we found ourselves and we've we've emerged happily and successfully out of some of those partnerships or that didn't bear the fruit we expected them to. But But yeah, I think I think I'd be a little bit more cynical now.

Steve Brown : 

What is surprised you? So when I'm, I always got pigeon holed in the seals, sales, because that's what those companies needed the most that I worked for. But then when I started my company, as all these different things that I started to get to do that I never done before, and I figured out I'm good at this. I'm good at that. And I would never know what surprised you about what revealed itself that you got. Wow, I'm good at that. I never would have predicted or expected that.

Lindy Ledohowski : 

Yeah, you know what, interestingly, I would have to say sales. So I if you had asked me I would have said in a million years I am not a salesperson. And again, that's probably my you know, big headed academic self thinking and sales is like a sleazy used car dealership. All right, I like that. I think I had a lot of ignorance that that good sales is actually about conversations and good sales, I think is listening to your your potential prospects and then trying to give them what you hear it is that they need. And if in all honesty if the thing that you're offering isn't going to be what they need, don't tell them don't force that, you know, you can use it you will achieve more as a salesperson by keeping that relationship warm and healthy. By not selling them by by making sure that they know Okay, actually, you know what, our products not a great fit for you. And then they'll recommend you to somebody else where it is a good fit as opposed to me just continually being like, Hey, you and I say jack, how about now john, so jack just doesn't work. So that was a surprise to me, because I as I say, I really You know, wouldn't have pegged myself as a kind of salesy person?

Steve Brown : 

That's a great answer. I love that. So

Lindy Ledohowski : 

you tell me, am I am i right on sales? Is it about relationships?

Steve Brown : 

Totally? Well, you it's an important part. And a lot of people call themselves sales people aren't. They're just, they, they're avoiding other positions, and lots of companies will go, they'll go, are you a salesperson? And they'll go, yeah, I'm a salesperson. Well, we found the salesperson come on board, and then we figured out later, they're not a salesperson. They're a visitor. They just go and visit people waste their time and they're not selling our stuff.

Lindy Ledohowski : 

They're a meeting goer.

Steve Brown : 

Right. There's a point you have to risk the relationship to ask, are we going to do business or not? And if they can't get past that, so relationships there, but it can't be the main thing that you're good at. So you're running a company obviously employees vendor Yeah, those people come into play there. Yeah. Yeah. How's that working for you?

Lindy Ledohowski : 

Yeah. So, again, one of the things I could probably even have equally answered this to this sort of surprising skill set that I didn't know I had that but that has is emerging that I do have is is working with employees. And one of the things that I think is surprising that emerges out of finding yourself in kind of a leadership or management position, when you know, you didn't come into it that way, is that for me, I take all of my teaching experience, and it comes into play in terms of leadership. And in some ways, I'm a way better teacher now because the stakes are so much higher, like in a classroom. If you don't reach 100% of the students and they fail. Well, they fail, you know, obviously, you're sad read their life. Whereas if you can't get your team to work your business fails. Yeah, the failure is not an option. You know, if if Jimmy or Susie on your team are underperforming, it's not Jimmy or Susie that fail. It's, you know, the company can tank as a result of that. And so that's been kind of interesting and really interesting dynamics, how do you get team cohesion and work well with teams and and then find people who have complementary skill sets to you and then give them the freedom and the autonomy to do the things that they do well without micromanaging them. So that's been actually a really fun part of growing as a jack as a company and sort of developing all of those components and dealing with sort of vendors and partners and like invoicing and, and payroll and accounting and bookkeeping and all that. Like that, I would say is not My passion in life. That's the sort of, like kind of necessary evil. And I think, you know, if you if you start a business and you're in the sort of early startup stages, you do it all. So I think it's important that I do do it all because I have visibility on all parts of the business. As our team likes to joke, I'm the, say jack of all trades. I do have that kind of window into you know, obviously the educational piece in the marketing piece and the digital platform piece and product development piece, but also the finance and the accounting and the banking and human resources and all of those component parts. And so again, it's been a learning but I don't love it.

Steve Brown : 

So why the name sa jack might not like sa whisperer. What's the thinking? Where did jack jack

Lindy Ledohowski : 

who is jack You know, that's the key question who is so jack is your reader obviously so but when We first started and we again, as I say, we're originally thinking of it as a platform, we have this platform, and we were testing it with those initial sort of hundreds of students. And we were originally thinking of it as like the essay hack, you know, this is weak, you can hack your essay. And that's sort of the very basic terminology. And then when the students really started to like it, we were like, Oh, well, we can't like trademark essay hack, like essay is just a common word hack is just a common word. And, you know, so so we need to find something that's a little bit more precise. So we searched for around a bunch of things in essay jack, simply just because it sounded like sa hack was one that we were testing. And then it started to have a life of its own. So the students would be high. They'd be working together, like, Oh, you know, jack is asking me for evidence, what is your evidence for me? Thanks, and how, you know, say jack is becoming this kind of person that that is reminding the writer that they're always writing for a reader. So that was really Like setting, and then we had other feedback where they're like, Oh my gosh, this is amazing. It's like, you know, the Jackknife of essay writing, it has all these different pieces that you can, gosh, I never heard, you know, I never thought of that, you know, so it started to have all these fun connotations. And so it stuck, if you know, and again, to go back to the marketing and branding, I don't know now that it's the name that I would have chosen, or even if it's going to stay forever, because the platform now does so much more than just essays. So we've got templates for TED talk and persuasive speech and lab reports. And, you know, whereas, because essays in the the name of the company, and therefore the name of the product, people tend to think like, Oh, it's just essays. And I mean, that is certainly, you know, our starting point, but there's so much more so I suspect, you know, if I were a betting person, you know, and in the next you know, years to come, it'll probably be some I don't know, some other great name that some marketing and branding guru will come up with and then it'll be powered by Yes, Ajax, so, so there. So that's also, you know, exciting because like as a as a teacher, as a writer, as a scholar, I do like the creative part of the business. So I liked creating essay jack. But now, some of the puzzles are like creating marketing campaigns that work or creating branding ideas that can take you to the next level. So I I'm this new phase where you know, the product itself is pretty great. And now it's sort of Okay, what can we do around the marketing and the branding? And how do we engage with our customers in that in that way to have them feel the things that that we would like them to feel that is sort of the new creative puzzle ahead of us. And that I can kind of sink my teeth into which is a bit exciting.

Steve Brown : 

Exciting. So where in the in the lifecycle of a startup SAS company? Are you like, you're over the first hump and now you're starting to iterate a little bid and you're getting more fine tune. You've got employees, how many? How many people have signed up and are using it? You know, I'm yeah, I'm curious about that stage.

Lindy Ledohowski : 

Yeah, yeah. So and and I always, it always feels like we're still super super at the beginning but but we're not really so I've now realized there there are kind of three phases. So there's, if you think the initial phase is kind of the product and the validation, and then niche market and all that, so then there's a lot of building iterating at that point. So what is your product? Who are you selling it to? How are you selling, you know, all of those kind of things, and are you improving the product and all that so so we spent a good chunk of time, probably in total, I would say about two and a half years really there and had probably about 5000 si jack users in that bucket of time. Then, in 2018, based on sort of a lot of that feedback, we rebuilt the platform or 2017 2018 we read Build the platform. And that's where as I say, it's become this like, expansive. You know, it does all of these wonderful things and has this new shiny interface. And it's like infinitely scalable. And, you know, we, we move the architecture into the cloud. So it's a Google Cloud Platform hosted products. So as we, you know, go viral, which is just gonna happen any day now, then. Totally, yeah, exactly. After this podcast, you can handle the millions and millions of users. But no, so we're sort of like at the second phase, which is really that refining that go to market strategy and product market fit. So who exactly are you selling to as I say, in the beginning, we were testing with like grade eight, right up until University, so that's a pretty big swath, and so SAE jack applies everybody. But so now, so how do you narrow it down? What is that pain point that transition from high school to university right now what we're seeing with a lot of kids who have been out of school due to COVID, but then they've got whatever's coming next and there may be gaps in their knowledge. So it could be that they're trying Transitioning from middle school to high school, and their parents are freaking out. They may not be freaking out because they're teenagers, but their parents like oh my god, you know, you you just haven't been at school for three months, are you going to be prepared for grade nine grade 10? In some cases, it's the the graduating class. So there are all these graduates of 2020, who have had this entire virtual experience, and then they're gonna go off to college or university in the fall. And they themselves might be like, Am I prepared? You know, again, their parents are probably also like, make sure you're prepared. And it's this whole new world where a lot of stuff is happening online. So that's kind of as we're narrowing it, that's okay. That's that product market fit. It's those those kids who are feeling that pain of that transition, often and wanting to make sure that they're prepared. And then the third phase of a startup is like, okay, you're ready to sort of grow exponentially and we're in that second phase. Yeah, having ready to move into into phase three, so we're gonna be by the end of this summer, we'll be doing a seed investment round. So that's Exciting. So that's our first external investment. And we've been running things we bootstrapped. We've had revenues, we've had grants. And you know, we begged, borrowed and stole from whoever we could, you know, we did a friends and family round to get us off the ground. And that took us really quite far. And now we can sort of confidently say, Okay, this is an edtech business, we have a side for myself, there's five staff, we've got over 30,000 people in the platform, we're seeing continual year over year growth. During the teaching semester, we have month over month growth. So all of those kinds of like metrics that matter from a business perspective, as opposed to like, when I started in the metrics that matter to me, it was like, does it make people write better? I now have those a handle on those business metrics, you know, what is the lifetime value of a customer? How do you put $1 point? How do you figure out your customer acquisition costs, in terms of the percentage of time your team spends to acquire a customer and all of those sorts of things? So now I'm like, Okay, I got that. We're We're ready to sort of take this to an external investor. And then, you know, on the back of that external investment, and obviously this podcast, we're gonna go viral and then phase three.

Steve Brown : 

I'm telling ya, this is exciting. I'm so happy my audience got to meet you. This has been an awesome conversation. I've had to really work hard to pump and get information out of you. But I'm telling you, Dr. Lindy you you've your fun conversation. I've enjoyed it so much.

Lindy Ledohowski : 

Oh, thanks so much, Steve. This has been great. Like you're you are a great interviewer. I can say that's what

Steve Brown : 

I've been telling my dog ferns. She listened to all these conversations and I, I have to she's the smartest dog in marketing. I say you know, she knows it all. And she's like, I could ask these questions. She looks at me, you know, and and she's grading what I said there. You know, you could have said that a little bit better Steve, but She leaves me alone when I fumble and don't don't give her a red pen just don't ever read. I get these emotions over red pins. So if First of all, if people want to contact you and learn more about se jack or maybe they're they want to be a seed investor. what's what's the best way to connect with you?

Lindy Ledohowski : 

Yeah, so there there are a couple so obviously one quick way is through the website. So that's just www.sh jack calm so there and there are a bunch of you know, there's contact forums and everything if you just want to get information. I'm on Twitter, and it's at Dr. Lindy and I think my DMS are open it's easy to get in touch with me that way sh jack is on twitter at sh jack. I'm also on LinkedIn and Facebook and Instagram and as as I say jack so definitely we can be found we can be connected. We are like real people behind this. So yeah, that's the message we will we will absolutely get it and then and Then move things forward, whether that's going to be through like a zoom conversation as now nobody's meeting in person or phone call or an email or whatever. So So yeah, easy to get in touch with.

Steve Brown : 

Love it. Great conversation. Great guest Doug and Lindy thank you for me and on the ROI online podcast.

Lindy Ledohowski : 

Thank you for having me, Steve.

Steve Brown : 

My pleasure. And that's a wrap. Thanks for listening to another fun episode of the ROI online podcast. For more, be sure to check out the show notes of this episode. And feel free to connect with me on LinkedIn where we can chat, and I can help direct you to the resources you're searching for. To learn more about how you can grow your business better, be sure to pick up your copy of my book, The Golden toilet at surprise, the Golden toilet.com I'm Steve Brown, and we'll see you next week on another fun episode of the ROI online. podcast