Diary of a Founder: The Story, The Layoff, & The Future Part 1

Welcome back to The Canopy, the view from above where we talk GEO, founder life, and growing your visibility in AI search. I'm Jen Shannon, your host and founder of Clemelopy. And if you're listening, I just want to give you a quick shout out. Thank you so much for listening and supporting this podcast. Today is not only our first episode of Diary of a Founder, but it will be a two part episode, of course, today being the first.

I'll be taking you back to the very beginning when I decided I wanted to work for myself, my businesses along the way, where Clemelopy's story began, which was of course in my head, and what has led me here today. So buckle up. This one is going to be a history lesson.

This episode of The Canopy is brought to you by Clemelopy, helping small businesses grow their visibility in AI powered search. Learn more at Clemelopy.com.

Just kidding. But, seriously, back in my day. I had known I wanted to work for myself someday, and I didn't know what I would be doing, only that I wanted to work for myself. And it was because the idea of working for myself gave me this freedom to be able to live my life the way that I wanted to while also doing something that I loved. So there I was.

It was March twenty fourth two thousand eight. I was living in Chicago with my husband. At the time, I was a contract negotiator for Aetna and a work at home employee. I was also going to school at Columbia College Chicago at night and sometimes on the weekends, depending on the semester. We had just bought our first home a few months before then, and I was sitting on the couch with my laptop, working on a school project. And my husband was installing some new baseboards in the living room.

I had this feeling that had been building inside of me for a while that I wanted a way to earn an income on the side so that maybe one day I could work for myself. At the time, I was studying graphic design and photography, and I remember making the decision right then and there that I was starting a graphic design business. I looked up and I said to my husband, whose name is Colby, I'm starting a graphic design business. What should I call it?

And just a sidebar, my husband has been nothing but one million percent supportive of everything I have ever done. He is also, however, my voice of reason. And so when I get a new idea or something, before I jump on it, I always talk to him about it and try to get his take, thinking through things to make sure I have a clear sense of all of the obstacles that I could be facing. So just keep that in mind.

So after we talked for a little bit, he and I came up with the idea of Starlight Art and Design. And I'll spare you all of the nitty gritty details, but let's just say what was supposed to be a graphic design company turned into a photography company. And then that turned into from Starlight Art and Design to Jen Shannon Photography. Then that turned into Jen Shannon Creative Atelier, and now we are here. I still have Jen Shannon Creative Atelier, but that's more of a fun way to sell my art without the pressure of it being my livelihood.

I was a successful photographer for ten years, eight of which were in Jacksonville, Florida, where I was from. And I mentioned this because in two thousand ten, two years after I started my business, I had gotten laid off from Aetna, which I will go into later in this story. So eight of those years were here in Jacksonville, Florida after we had moved back here.

The last four to five years of my photography career, I focused solely on portraits, specializing in modern women's portraiture, but probably better known as the Sue Bryce style of portrait photography. I had opened a studio and it was a dream I had had since two thousand and eight. And in late twenty seventeen, when I was pregnant with my son, who was our last child and our fourth, I realized I didn't want to do it anymore. We were fortunate enough that financially we could make that decision, but it wasn't until a couple of months after that realization that I finally talked to my husband about it. I had my best friend by my side to vouch for the fact that I had been thinking about it for a while.

I remember sitting on the back porch wrapped in a blanket because it was freezing cold outside. My husband and I miss Chicago, so we like to sit outside when it's freezing and just bundle up. There was a constant breeze blowing. The sky was clear. You could see all the stars. And my husband just said, okay. He said he could tell I wasn't happy, and that just made me feel so supported and loved. With our son about to be born in a few months from that time, he knew that I was already spread too thin and adding our fourth child to it was going to be even more difficult.

So I officially closed my studio on April thirtieth twenty eighteen, and my son was born at the end of May of twenty eighteen. And our lives were turned upside down when he was born because, unbeknownst to us, he was born with a heart defect. I could talk for hours about this time in our lives, but that's not the point of this podcast. But it's an important piece of the story because needless to say, the next few years were spent raising our kids, taking him to doctor's appointments. He had multiple inpatient stays, and it just seemed, looking back, to be a blessing in disguise that I wasn't happy doing photography anymore because we had no idea what was to come, and I certainly wouldn't have been able to continue the studio during that time.

After the dust settled from my son's birth, I had time to contemplate a lot of different things that were happening in that time of our lives. And one of the things was always wondering why, if being a successful photographer was my dream, why was I not happy doing it? Well, my friends, hindsight is twenty twenty. But I think the main reason was that I had, quote, unquote, made it as a photographer — but still there was a ceiling to just how much I could earn by myself, especially having three little ones at home and eventually our fourth.

And I wanted to be there to raise my kids while also building my studio. But the reality was none of my kids were in school when I first opened my studio, and yet working more wasn't an option for the lifestyle my husband and I were creating together. I'd need to hire an assistant, which I actually did at one point and got burned by that. And I would need to hire a nanny, which I already was doing a couple of times a week so that I could be at the studio doing work and portraits. So the hindsight is that the picture I had in my mind was not the picture I had created, and I wanted the recognition and reputation of being a successful photographer with doing it all on my own. But doing it all on my own was never going to be realistic.

After my son was born in twenty eighteen, we focused primarily on his health. But once the outpatient visits slowed, I found myself still itching to try to earn an income. It's just ingrained in who I am. I am an Enneagram three wing four, and if you're familiar with Enneagram, the three is an achiever. And, boy, if being an overachiever is a thing, that is definitely me. It's always been ingrained in who I am. And so for whatever reason, building a business has always been something that is just deep within me. I love turning nothing into something.

So I started creating art and trying to sell things on Etsy. Eventually, I moved into pouring resin during the pandemic and kind of started combining that with some woodworking and doing some surface pattern designs and so on and so forth. And that turned into doing art markets, which were actually pretty lucrative in my first year, which was twenty twenty three. But my second year, twenty twenty four, was awful. Each market felt like I was paying more to just be there than I was earning.

The fall came, and I saw a job opening for a company I had followed for a long time. I applied for it, and after three phases of interviews, I accepted the position. It really was a dream job, and I loved it. And I loved the people, and I loved the benefits. And I loved especially that I could still work at home and still be there for my kids. And for once, it was nice to have a steady paycheck because I hadn't had one since I got laid off from Aetna in twenty ten.

So creating out of a place of having to make a living really sucks the joy and fulfillment out of the actual act of creation. Because suddenly, instead of creating from a place of inspiration, you're creating from a place of — I don't wanna say desperation because that's too strong of a word, but you're forced to create when you're not feeling creative. And you have that worry, like, am I going to get paid putting all this time and effort into creating this piece? And so there's just a lot that goes into creating art as a living, and I know a lot of people do that. But for me, it just took the joy out of creating.

And so I felt like I could relax and exhale and really regroup after getting this job so that I could figure out what I wanted as an entrepreneur. And the company I was working for fully supported side hustles, so I was fully supported to do whatever I wanted on the side, but I just couldn't figure out what fit.

I wanna pause here to talk about something that a lot of people usually shy away from, and that is money. I used to have a really stinky attitude about money, getting angry at people who bought stupidly expensive things like their own helicopters or Lamborghinis, because it just felt like such a waste and that they could be helping so many people and causes with that money that they spend on those things. But then I had a shift in my mindset around twenty ten.

These people worked hard to get where they are and to be able to afford what they purchase. Maybe they earn what people could call a gross amount of money, but you know what? Kudos to them for building something that gave that to them. And truthfully, a lot of these people are giving back as well. So part of my dream of being a photographer was the hope of creating wealth for our family. But the reality is that without sacrificing things that were important to me, I was never going to build wealth as a photographer. I wasn't going to build wealth going to art markets every weekend and sometimes during the week. And maybe some people could challenge that, and I'm not saying it's impossible, but I'm saying for my story, I would have to sacrifice being the mother that I wanted to be to my children in order to work even more to make that happen. And I would have to hire people, and I didn't want to trust someone with my business after having been burned.

But to build wealth, the idea is not to be able to just go out and purchase whatever you want whenever you want. It's to leave a legacy for my children, and that's generational wealth. And for any of you who are big Dave Ramsey fans, I am a huge Dave Ramsey fan. And so we follow him to almost a t. And so for us, we really want to build something that we can retire with comfortably and we can leave and pass on to our children.

So during this time, I was working for this company in twenty twenty five. I was listening to Diary of a CEO. It was an episode that had Alex Hormozi, Cody Sanchez, and Daniel Priestley. They were each given a suitcase with a specific amount of money. One at a time, they would open their suitcase and describe what they would do with that amount of money to build a scalable business. And that led me down a rabbit hole of Alex Hormozi's videos on YouTube, and I'll never forget what he said. He said he would pocket the thousand dollars, learn as much as he could about AI, maybe work for someone for a year to learn as much as he could, and then start his own business implementing AI for other companies. And that got me thinking. AI really is the future, and I'm already quite knowledgeable about it. Maybe something with AI could be something that I create a side hustle with. And that thought didn't really go anywhere for a while.

So during that time that I was working for this company, I had also been tasked with researching generative engine optimization for the company that I worked for. I researched every single thing I could find about GEO, how AI models worked, what large language models liked and disliked, and how websites can be optimized to show up in search results. And I put together a presentation and realized it was filled with technical jargon I knew my boss wasn't going to understand, and if she couldn't understand, neither would anyone else in the company. So I came up with an idea to try to relate it to nature because I knew that was a language my boss at the time understood, though at the time, it was not related to an orchard.

But fast forward to October twenty twenty five, and I was feeling ready to begin exploring what my side hustle was going to be. I knew it was gonna be something AI related, but I wasn't totally clear on what my vision was. So I remember, and this may be TMI, but that's okay because I do TMI. I had gotten out of the shower and sat on a chair in my room, wrapped in my towel, drying off, when I grabbed my phone, opened ChatGPT, and said, I wanna start an AI company. What should I do? And literally nothing it recommended seemed good, sustainable, or interesting. So I put my phone down feeling a bit defeated.

But as I got dressed and ready to go downstairs to cook dinner, my mind wandered back to that presentation I was putting together. And suddenly, I had this idea to create a company that teaches people how to optimize their websites for AI search. I had literally just spent weeks researching how it all works and how the pieces fit together. And if I could make it understandable without a lot of jargon, then this could be really valuable, especially to small business owners, many of whom run their own websites.

So October eighteenth twenty twenty five, I decided to start a company, and I wanted to name it Clementine with a y. I have a Clementine tree out back, who I know I've mentioned before I have an oh so original name for. Her name is Clementine. If you know me, I name everything. My van's name is Vesna. No, not Vecna from Stranger Things. Vesna from a board game called Scythe and the Scythe expansion. Did I mention I'm a Board Game Geek? And my husband's SUV is named Finn McMissile after the movie Cars. And I also have a rechargeable fan in my purse I named Estelle because perimenopause started hitting hard this year.

Anyway, so I think Clementine with a y would be cute and maybe available. But let me tell you how wrong I was. Not only was it taken and already trademarked as a SaaS company, which is a software as a service, every other name I came up with and tried over a course of two days was taken. And now I understand why services like Lyft are spelled with a y or why some company names are just weird because literally everything is taken. So it took me two days to decide it was time to approach it differently. I was going to give it — wait for it — the celebrity couple name treatment. The only problem was trying to decide what the other half of the name was gonna be. Well, since clementine is a plant, I decided I had to name the other half after a plant. And I only have one other plant with a name. Her name is Penelope. She is a polka dot begonia I got during the plant craze of twenty twenty one and is my longest living houseplant. She sits perched on my bathroom tub and is quite happy there. At one point, I propagated her and named her baby Marjorie and gave it to my sister-in-law who eventually killed it. And, Lindsay, if you're listening to this, how dare you? But Marjorie will now only live on in our memories. I guess you could say what died didn't stay dead. If you know, you know.

So that settled it. The celebrity couple name of my new business turned out to be Clemelopy. On October twenty third after work, I filed the paperwork to form the LLC, get a tax ID number, and register for sales tax in the state of Florida. So, again, there I was thinking this would be a great side hustle to work on the nights and weekends while my kids were out with their friends and during their practices. I could just take my laptop and work from the ball fields. It was gonna be great.

But then Halloween came. Now Halloween is actually my mom's birthday. We typically have my brother and sister-in-law, Lindsay, over. We celebrate Halloween with trick or treating. And afterwards, we have dinner together and cake at my house. At that time, two people had left the company I was working for about a month and a half prior or so, and we were supposed to be redefining our roles within the company. I was excitedly looking forward to the call that was booked for that discussion on the afternoon of Halloween to learn what the new role would entail, but instead, they were downsizing and my role was being eliminated.

I was devastated. I truly loved this company and my coworkers, believing I would be there for the long haul, and in a ten minute or so Zoom call, all of that shattered. If you've ever been laid off before, it is emotionally very difficult. In twenty ten, I got laid off from my job at Aetna because we had been awarded the TRICARE contract, and I had moved into a position that involved negotiating contracts specifically for the new TRICARE business. But then the company that previously had the contract, Health Net, appealed the decision to give Aetna the business, and we lost the business. So I lost my job. I happily welcomed it, though, because I was ready to move back to Jacksonville, live by my family and friends, and have a chance to go full time with my photography business, and that's exactly what I did.

But this layoff — this layoff was different. I honestly didn't see it coming. While I wish I could be as bold as a fellow previous coworker who left the company to speak my truth about the aftermath of the layoff, to preserve the integrity of that business, I'm not going to speak publicly about it. But what I will say is that I left with more questions I will never have answers to and complete silence that still somehow echoes loudly in my ears.

I felt awful trying to cover up my sadness and devastation all through Halloween. I found myself staring off into space several times and hoping no one saw it. I felt embarrassed and ashamed because regardless of why the layoff happens, you analyze everything you've ever done for that company and wonder where you went wrong. What was it about me or my work? Could I have done something better? Am I going to be perceived as lazy? Will I be hireable elsewhere, or does this put a black mark on my record? What happens if I run out of savings and still don't have full time employment? Can I get Clemelopy off the ground fast enough to earn some sort of income?

What I needed was a plan, some time to think and ground myself, and to put all of my feelings, confusion, and frustration surrounding that layoff aside in a little compartment so I could forge the road ahead of me, at least for the next couple of weeks, and then process that compartment later.

And that's where we will end episode one about how Clemelopy came to be. In the next episode of Diary of a Founder, I'll continue the story of Clemelopy. This is where it gets strategic. I talk about all the solutions I tried and what I eventually settled on. And honestly, I feel like this first episode really sets the stage for what's to come. So I hope you enjoyed listening to the beginning of my story here and that you will be just as excited to listen to the next part of this story because, like I said, this is where we get down into the nitty gritty. So with that being said, thank you so much for listening, and as always, keep growing forward.