The First Thirteen

On January 13, 2006, I incorporated CI Web Group.

That sentence, on the page, is short. Behind it sits the longest single decision of my life. I was thirty years old. I had a seven-year-old son. I had walked away from a six-figure executive position with stock options. I had no co-founders. I had no investors. I had no office and no employees. I had a logo, a domain name, an LLC, and a working theory about who I wanted to serve and how I wanted to serve them. The working theory turned out to be right. Most of the rest, I was going to have to figure out as I went.

I want to walk you through what the founding of CI Web Group actually looked like, because the version most people who know me from a stage hear is the cleaned-up version. The cleaned-up version says I started a digital marketing agency for trades contractors in 2006, grew it, navigated the SEO industry through the Google updates of the 2010s, made an early bet on AI, and ended up at the front of the agentic-marketing wave in 2026. All of that is true. None of it captures what the first three years actually felt like.

The first three years felt like building a ladder rung by rung in the dark, while carrying a child, on the side of a mountain I was not certain had a top.

January 13, 2006

I did not pick the thirteenth on purpose.

That is the first thing I want you to know about the date. By 2006, my son had been alive for seven years. November 13, 1998 was on every birthday cake in our house. I knew, in some quiet part of my mind, that thirteen was a number that had shown up in my life in a meaningful way. But when I sat down to incorporate the company, I was not thinking about the pattern. I was thinking about the practical question of when the LLC paperwork could be filed and accepted, and the answer was the second week of January 2006, because that was when my lawyer had the documents ready and the state office was processing filings. The thirteenth was the day the paperwork went through. I did not learn that I had founded my company on a thirteen until later, when I looked back and noticed.

That is how the thirteens have always worked in my family. They have not been chosen. They have been received. The dates have arrived on their own and the pattern has only become visible in retrospect. My father would have appreciated that. He spent his career teaching machines to recognize patterns in data, and the patterns most worth recognizing are usually the ones nobody set out to create.

[PLACEHOLDER — Jennifer to fill in: the actual scene of January 13, 2006. Where you were when the LLC went through. Whether you celebrated, or whether you just kept working. Who you told first. What you remember about that specific Friday. If you do not remember the specific day, that is fine — the chapter can acknowledge that the founding day was administrative rather than ceremonial, which is also part of the story.]

The name was CI Web Group. CI stood for Central Intelligence — a phrase I had been carrying for a while because it captured what I thought a good marketing partner should be for a contractor: not a vendor selling them ad spend, but the central intelligence of how they showed up online. The agency was, from the very first day, named after a function. Not a person. Not a place. Not an aspiration. A function. That naming choice is one I am still proud of, twenty years later, because the function we were named for is the function we have continued to serve, even as the technology underneath it has gone through three complete generations.

Web Group was the practical part. It said what we did. We worked on the web. We worked in groups. The combination of “Central Intelligence” and “Web Group” was, in retrospect, an early signal of what I thought the work was supposed to be. The work was supposed to be the brain, not the hands. The work was supposed to be the strategy, not the production. The work was supposed to be the function that organized everything else a contractor had going on, online, into a single coherent presence. Twenty years later, the technology has moved from PHP-driven WordPress sites to AI-orchestrated agent networks, and the function I named the company after in 2006 turns out to be exactly what an AI agent does for its operator in 2026. Central intelligence.

I was, again, raised to be early.

The Decade Before

Before I tell you about the founding, I have to tell you about the decade that produced the woman who founded it.

I graduated high school in 1993. The same year Mosaic was released. The same year the visual web showed up on a screen in my father’s house and rearranged my sense of what was about to be possible. I was eighteen years old. I had a high school diploma, no plan beyond the next year, and a kind of instinct — not articulated, not yet — that the world I had grown up in was about to be replaced by a different one.

I went to college for one quarter. I quit.

I did not quit because I was bored, or rebellious, or unable to do the work. I quit because I had figured out, in the first ten weeks, that the version of life college was preparing me for was not the version I was interested in living. The version I was interested in was the one where you started doing the work immediately, learned the work by doing it, and let your performance — not your transcript — be the thing that moved you forward. So I left.

I went directly into corporate work. I started at the bottom.

My first job was at Lamonts Apparel, the Pacific Northwest department-store chain. I worked the floor. I learned what retail operations actually looked like at the unit level — the stockroom, the registers, the customer interactions, the daily inventory math, the small operational decisions that, multiplied by the number of stores in the chain, determined whether a regional retailer was healthy or in trouble. I was nineteen, twenty, twenty-one years old. The work was not glamorous. It also was not the kind of work that wastes your time if you pay attention, because the lessons it teaches you about how a real business actually moves through a year are the lessons most college graduates do not learn for another five to ten years after they leave school.

From Lamonts I went to Nordstrom.

If you have spent any time in retail, you understand what it means to work for Nordstrom. Nordstrom, in the 1990s, was the most operationally sophisticated customer-service organization in American retail. Its training program is studied in business schools. Its expectations of the floor staff are higher than any other department-store chain in the country, and its rewards for meeting those expectations — in compensation, in advancement, in cultural status inside the building — are correspondingly higher. Nordstrom is where I learned that the difference between an acceptable customer interaction and a memorable one is almost entirely a function of the operator’s attention. The chain was teaching me, without my realizing it at the time, the same lesson my mother had been teaching me my whole life: do the work. Pay attention. Outwork the room.

From Nordstrom I went to Tommy Bahama. The upscale lifestyle brand, also Seattle-based at the time, was a different kind of operation — smaller scale, higher-margin product, brand-driven retail rather than category retail. I learned, at Tommy Bahama, what it meant to sell a lifestyle rather than a transaction, and what it meant to operate inside a company small enough that the decisions you made on the floor were visible to the people running the company at the top.

Lamonts. Nordstrom. Tommy Bahama. Five years across three Pacific Northwest retailers. By 1998 I was twenty-three years old. I had figured out how to operate inside a regional chain, a national chain, and a brand company, and I had figured out that the people who got promoted in retail were the people who took on the projects nobody else wanted, especially the projects that had not been done before. That was the operating posture I had developed by twenty-three. Take on the complicated forward-thinking project. Especially the one that had not been done yet. Do it. Let the doing of it earn you the next thing.

That posture, more than any other single thing about me, is the spine of everything that came after.

In November of 1998, I had Torel. November 13th. A thirteen, like most of the dates that matter in my life. I was twenty-three years old, unmarried, with a newborn, working in retail in Seattle. The next move was to find an employer who could pay enough to support a child and who had room for the kind of operating posture I had been developing across the previous five years. The employer that came up was Fossil.

Fossil — the watch and accessories company — hired me out of Seattle and, when Torel was about two years old, relocated me to Dallas, Texas. The relocation was the move that took me away from the Pacific Northwest and away from my parents, who were devastated to see their only daughter and only grandson leave Washington for a city two thousand miles south. They never said so directly. They were the kind of people who let you go where you needed to go. But I knew. I have lived with knowing for the last twenty-six years. Some of what I have done in the most recent chapter of my life — the Greenlake home, the closing of the geographic loop — has been my attempt to repay that knowing.

Fossil is where I reached the executive level. By 2003, I was Executive Director of Supply Chain Compliance — the operational engine that ensures a global watch and accessories company’s manufacturing partners across multiple continents are operating to standard, that the legal and regulatory and quality requirements of every market are being met, and that the goods moving through the system arrive intact and on time. It is the kind of role most people outside global retail do not realize exists, and the kind of role that makes the people inside global retail look at you twice when you tell them what you used to do. Supply chain compliance at the executive level is operations engineering at scale. It is also exactly the kind of work that produces the operating instincts I would later need to run an agency.

Ten years from the floor at Lamonts to that title. Ten years of taking on the complicated forward-thinking projects — the ones nobody else wanted, the ones that had not been done before, the ones that would either work or fail visibly. Ten years of doing the work and letting the work move me forward. By the time I had reached the executive seat, I was a thirty-year-old woman with a child in elementary school, a corporate role that paid well, and a goal I had set myself years earlier that the corporate role was not going to satisfy.

The goal was simple. Be an entrepreneur by the time I turned thirty.

I had been carrying that goal on the calendar the way my father had carried his shipping calendars on the calendar — not as an aspiration but as a deadline. The deadline was running out. I was, by the end of 2005, about to be on the wrong side of the goal I had set myself. So I left.

The goal was simple. Be an entrepreneur by the time I turned thirty.

The week I walked out of Fossil, I was still inside the window of the deadline. By a small margin. But by a margin.

Three months later, on January 13, 2006, I founded CI Web Group.

The decade between the floor at Lamonts and the founding of the agency was not preparation for the founding. The founding was the natural extrapolation of the decade. The same operator who had taken on every complicated forward-thinking retail project at Lamonts, Nordstrom, Tommy Bahama, and Fossil, especially the ones that had not been done before, was now going to take on a complicated forward-thinking project that nobody in the trades industry had ever done: build an agency that helped HVAC and plumbing and electrical contractors win on the early internet. Same posture. Same operating discipline. Same kind of work, in a different industry, at a different scale, with my own name on the door instead of someone else’s.

That is what the decade before produced. That is who showed up at the founding.

Why Trades

People ask me, all the time, why trades contractors.

It is the question that comes up at every conference, on every podcast, in every introductory meeting with a new investor or a new partner. Why HVAC. Why plumbing. Why electrical. Why roofing. Why garage doors. Of all the verticals you could have chosen in 2006, why this one. The implicit question underneath is: why did you pick the unglamorous one. Why did you pick the one that does not get covered in TechCrunch. Why did you pick the one that the rest of the digital marketing industry was, at the time, mostly ignoring.

I want to give you the honest answer, because the honest answer is also the most useful one for anybody reading this book who is trying to figure out which vertical to bet their own career on.

The honest answer is that I did not pick the trades. The trades picked me.

In 2006 and 2007, I was running CI Web Group as a generalist digital agency in Dallas. We took whoever would pay us. My cousin Chris was already with me by then — not as a founding partner, since CI Web Group was an LLC I had organized myself before he came on, but as the technical force the agency depended on from the early early days. We were on the WordPress development committee — a small group of contributors helping shape the open-source platform that was, in those years, displacing static HTML and Flash as the dominant technology stack of the small-business web. Most of our work was migrating clients from Flash websites to WordPress, building search engine optimization on top of the new sites, and teaching the clients how to operate inside a content management system they could actually update themselves. The clients ranged across whatever industries needed the work. Restaurants. Local services. Regional retailers. Small e-commerce operators. We were a small-team agency doing the foundational web migration work that the early Web 2.0 era required, and we did not, in those first two years, have any particular industry focus.

Then in 2008, a man named Tony Jeary recommended me to keynote at the Mitsubishi Diamond Dealer Conference.

Tony Jeary is one of the most respected executive coaches in the United States — a coach to top CEOs around the world, the developer of the Strategic Acceleration methodology, the author of multiple books on Clarity, Focus, and Execution. He had become my coach a year or two earlier, after the agency had been operating for a while. I will tell you more about him in the next chapter. For the purposes of this section, what matters is that he was keynoting at Mitsubishi’s 2008 conference and he told the conference organizers they should book me too. He saw something in me that I had not yet seen in myself, and he opened a door I did not know was there to open. I walked through it without knowing what was on the other side.

On the other side were three contractors who raised their hands when I asked who in the room was running search-engine optimization on their websites. The rest of the room did not raise theirs. Those three contractors became some of my earliest trades-industry clients, and the dynamic of that single room — the three at the leading edge, the rest waiting — became the structural template I would watch play out, in different forms, in trades industry rooms for the next eighteen years.

I had no idea, at the time, that the trades would take over my career. I walked into that 2008 keynote as a generalist agency operator who happened to have been recommended by her coach. I walked out of it with a foothold in an industry I had not previously known. The agency followed the foothold. By 2015 the trades had grown into a majority of our business and we made the strategic decision to commit fully to the industry. By 2026 we are the largest agency in the trades that is fully aligned with the AI-era infrastructure most of the industry has not yet acknowledged is arriving.

None of it would have happened without Tony Jeary opening the door.

That is the truth of how I came to the trades. The strategic case I am about to lay out for the industry was the case I came to understand after the trades had already chosen me. It was not the case that drove me into the industry in the first place. The reader who registers that distinction will register the rest of this book more honestly: most of the most important career decisions any operator makes are decisions that are made for them by people who see something they have not yet seen in themselves. Pay attention to who is opening doors for you. Walk through the right ones. The case for what is on the other side will become clear once you are inside.

Now let me give you the strategic case I came to understand.

The trades are the largest, most fragmented, most under-marketed, most local-search-dependent, most recession-resistant, most actively-needed sector of the American services economy. There are roughly 600,000 active trades contracting businesses in the United States. The vast majority are small — fewer than twenty employees. The vast majority do not have an in-house marketing department. The vast majority are owned by people who got into the trade because they liked the work, not because they liked the marketing. They are exactly the kind of operator who needs a partner who knows what they are doing online, because they themselves do not, and because they are too busy doing the work to learn.

That is a market description. Now let me give you the human one.

A trades contractor is the person who shows up at your house when something is broken. The HVAC technician who arrives at six PM on a hundred-degree afternoon when your air conditioner has died and your kids are crying in the living room. The plumber who shows up on a Sunday morning when your water heater has burst and your basement is filling up. The electrician who comes at two AM when the lights in your hospital have gone out. The garage door technician who fixes the spring that just snapped while your car is trapped inside and you are late for work. These are the people who keep the lights on, the water running, the heat working, and the world functional. They are doing the hardest, most underpaid, most under-respected work in the American economy.

And they were, in 2006, almost completely invisible online.

Their websites, when they had them, were built by their nephews, in HTML 4, with stock photos of stethoscopes for some reason, and contact forms that nobody monitored. Their Google rankings were determined by accident. Their reviews, when they existed, were on Yelp pages they did not know they had. The most important investment most contractors made in their own visibility was a magnetic sign on the door of a truck. The internet was happening to them. They were not happening to the internet.

I looked at all of that and saw the same thing my father had seen in the late 1970s when he looked at a banking system that was still moving paper checks by hand. I saw an industry that was about to be transformed by technology, that had not yet realized it was about to be transformed by technology, and that was going to need partners who could help it through the transition.

That was the bet. The bet was that the trades would, eventually, need digital marketing as much as the rest of the economy did, and that the agency that was waiting for them when they arrived would be the agency that defined the category.

Twenty years later, that bet has been validated approximately once a quarter, every quarter, since 2006.

The First Three Years

I want to be honest about what 2006 to 2008 actually looked like, because the cleaned-up version of agency history skips over the part that matters most.

The part that matters most is that for the first three years of CI Web Group, the agency was a small operation — I had raised Torel alone since the day he was born, my young son came with me to the office every day and grew up around the work, and my cousin Chris was already in the work with me from the early days, with his small son Braedn on most days on that same office floor next to Torel, taking the toaster apart at our feet because his hands wanted to know how things worked.

I want to introduce Chris properly here because he has been with me since the early early days of CI Web Group and he is part of every chapter that comes after. Chris is my cousin on my mother’s side of the family. He is the agency’s CTO. He has been the technical force the company runs on for twenty years. My father taught him to code when Chris was younger — not because Chris was Kevin’s blood, but because Chris had the curiosity and Kevin was the family member with the depth to teach him. Kevin’s technical inheritance, it turns out, did not run only through the bloodline of his daughter. It ran through whoever in the family had the patience to sit at the keyboard with him. Chris had the patience. Chris is who Chris is in part because of what Kevin gave him. And much of what I have learned about technology over the last twenty years has come from working so closely with Chris — the daily texture of building an agency next to a CTO who came up through the open-source community and the U.S. military teaches you things about systems that no book or course or conference can teach. Kevin gave me the foundation. Chris has been the one I have been refining the foundation alongside, week after week, for two decades.

Chris also came to the agency by way of the U.S. military, where he had built weapons tracking systems — the kind of mission-critical, security-cleared, life-and-death-stakes software where the consequence of a bug is not a customer complaint but a missing weapon, an audit failure, or a service member at risk. He had been hacking, by his own admission, since birth. The military was the institution that turned that capacity into a constructive career rather than a high-school grade-modification problem. By the time he and I started CI Web Group together in January of 2006, Chris had brought to the agency two things almost no other agency in the trades has ever had at the technical level: open-source-community contribution depth from the WordPress development committee, and the kind of operational discipline that comes from having shipped software under conditions civilian software vendors do not face.

And his son Braedn was at our feet.

Braedn was about a year old when Chris started working with me. By two he was disassembling the appliances. By the time he could speak in full sentences he was asking the kind of questions about how things worked that none of us had answers to. He grew up around the agency the way Torel did — in the office, on the floor, around the keyboards, watching the adults build — because his father was in the work alongside me. He is now, at twenty-one, one of our top AI engineers, having joined the company in the last three years to lead some of our agentic-systems development. The boy who took the toaster apart at our feet became the man building agentic workflows for the agency he had been around since he was small. Three generations of family-trained builders — Kevin Bagley to his nephew Chris Heney, Chris Heney to his son Braedn Heney — have produced the technical capacity the agency runs on in 2026. The Bagley side of my family taught the Heney side of my family to code half a century ago. The Heney side of my family is now building the AI infrastructure of CI Web Group in 2026. Both branches of the family are inside the work, and both branches are part of the line that runs through this book.

That is who was in the room when the agency began — and who would be in the room very shortly after. Two cousins on the WordPress development committee. Two small boys at our feet. One of those boys is now twenty-seven and a senior AI engineer in our office. The other is now twenty-one and one of our top AI builders. The agency was, from January 13, 2006, designed for the long arc. We just did not yet know how long the arc would be.

Within the first year and a half, one more person walked through the door who would become structurally as important to CI Web Group as anyone in the family. Her name is Kathy Marshall.

Kathy came to me as a client in our early generalist era — the period when CI Web Group was taking small-business clients across whatever industries needed the work. Before she walked into the agency, she had spent her career in the medical field. She graduated from Baylor College of Medicine on November 30, 1992 as a Physician Assistant — the clinical role that requires a Master’s degree and licensure to diagnose patients, prescribe medications, and assist in surgery alongside physicians. She served patients for eighteen years across five specialties — Neurology, Infectious Disease, Medical Oncology and Haematology, Gastroenterology, and Internal Medicine. The Medical Oncology and Haematology rotation matters for this book specifically, because it means the woman who is now my closest professional partner had spent years inside cancer wards before either of us knew that cancer would later take my father and that Kathy herself would later face it. She had the kind of training and the kind of professional discipline that medical practice produces. She had been a clinician. She knew how to translate technical specialty knowledge to people who needed to understand what was happening to them, the way a good PA does for every patient she sees.

In September of 2010, Kathy came to work for me. She had been a client of the agency and decided she wanted to be inside the operation rather than across the table from it. That kind of move is rare. People do not often pivot from clinical medicine into early-stage digital marketing in their thirties or forties. Kathy did. The skills transferred more cleanly than any of us realized at the time — the PA who could explain a diagnosis to a frightened patient turned out to be exactly the operator who could explain a website strategy to a frightened restaurant owner, and then a frightened HVAC contractor, and then several hundred frightened contractors who would eventually become the company’s addressable market. Customer-facing translation is its own craft. Kathy had been doing it her entire career. She was just doing it now in a different industry.

And then, a year later, she did something that very few employees ever do.

In 2011, she felt so passionate about the company that she invested. She put her own money in. She bought a 3% equity stake — a piece of CI Web Group out of her own savings, made out of conviction, in a small early-stage agency that was running out of a rented space in Richardson, Texas with everything in front of it still to be built. That decision, made by a former PA with the financial sense to know what she was doing and the conviction to do it anyway, made Kathy my only equity partner. She is, in 2026, the only person in the company’s capitalization table other than me. The 3% stake is still hers. The conviction has held for fifteen years.

Kathy is the most loyal person I have ever worked with. She is the biggest advocate the agency’s clients have. She heads up our customer service team and has, in the years since the company has scaled, become one of the structural reasons CI Web Group retains clients across decades. Most agencies have customer-service functions led by people who came up through customer service. CI Web Group has its customer-service function led by a former Physician Assistant whose entire professional formation was about translating between technical complexity and human-scale communication, and who has been doing the same work for our clients for sixteen years now. The retention rate the agency has built is partly a result of what Kathy specifically does and how she specifically does it. The contractors who have been with us for a decade have been with us in part because Kathy has been with them for a decade.

There is one more thing I want to register about Kathy here in 2026, because it is the present-tense reality I do not want to leave off the page. Kathy is sixty-seven years old as I write this. She was diagnosed with Stage 1 uterine cancer. She had the surgery. The surgery was successful, and the oncology team made the deliberate decision to be cautious with the post-surgery treatment plan — chemotherapy after the surgery, then radiation after the chemotherapy, the full belt-and-suspenders approach that careful oncology teams apply when they want to make sure nothing comes back. She is on her last treatment now as I write this paragraph. She has been working through the agency the entire time. She has not stepped away. The customer-service function has continued operating because she has continued operating it. When I asked her to tell me what the experience has been like, she sent me a sentence I want on the page in her own voice: “CIWG has the best HR department that has selected some of the best medical benefits, which have gotten me through Uterine Cancer Surgery, Radiation, and Chemotherapy, allowing me to remain financially stable.” That is the testimony of an equity partner about her own company. It is also, structurally, the kind of statement most CEO memoirs cannot make because most CEOs have not built the kind of operation that produces it. The fact lands in this book as something distinctive because of what the rest of the manuscript is doing — my father died of cancer in 2019, and the medical chapter at the end of this book is partly a meditation on what oncology can and cannot yet do. Kathy is now part of the picture too. The same disease that took my father from me went after my closest professional partner and was caught early, treated thoroughly, and is being followed up cautiously by a team that wants to make sure she comes out the other side without it ever coming back — with the company’s benefits architecture making sure she remains financially stable while it happens. She is sixty-seven, on the last round of her treatment, and still running the customer service function of the agency she invested her own money in fifteen years ago. That is the kind of woman she is, and that is the kind of present tense I am operating in as I close this section.

And then there is Kim.

Kim is Kathy’s daughter. She came to CI Web Group at eighteen years old. The agency was her first real job. That was ten years ago. She is twenty-eight now. Across that decade, Kim has done at least six different roles inside the company — moving through functions, learning what each one required, building the kind of cross-cutting understanding of the agency that only people who have actually worked in multiple departments develop. The role-mobility is unusual. Most agencies do not let employees rotate that much, and most employees do not have the underlying capacity to absorb six different functions across ten years. Kim does. She has now landed in the AI work. She is one of our vibe coders. She learned the AI domain quickly — the same pattern Liz and Allula and Kimberly all share, which is the underlying intelligence that allows a person to absorb a new technical domain at the speed the AI era requires. The work is producing the people. The people are producing the work. The architecture is now legible across two generations of the Marshall family inside the agency.

Kathy invested in 2011. Her daughter Kim came on around 2016, roughly five years later, at age eighteen — her first real job. The Marshall family is, in 2026, a two-generation thread inside CI Web Group, parallel to what the Heney family has been across Chris and Braedn, and parallel to what my own family is across Kevin and me and Torel and Liz and now Dallas. Three multi-generation threads inside one company is unusual. Most agencies cannot make that claim. CI Web Group can. The reason CI Web Group can is that the people who chose the company early chose it again and again across decades, and their families chose it after them, and the work has held.

That is the foundation underneath the agency the rest of this book is going to describe. Two cousins on the WordPress development committee. A former PA who became my only equity partner and now runs customer service. Two boys at our feet. A teenager named Kim who walked in at eighteen and has been here for a third of her life. Eventually, my own son and his future wife and his childhood best friend, all of whom will arrive in later chapters. The agency was, from very early, never just an agency. It was a place a small number of people chose to build something inside, and then chose again, and then chose again, until the choosing became the relationship and the relationship became the company.

There is one specific stretch of that early period I want to register, because it tells the reader something about how far I was willing to go to build this thing. Somewhere in the agency’s sixth year of life — specifically, from roughly May through September of 2012, by Kathy’s recall — I made a deliberate decision to give up everything and put one hundred percent of my effort and money into the business. I did not give up the office. I gave up everything else.

I moved into the office. Literally. For roughly five months, the Richardson, Texas office where CI Web Group operated was where I lived. Torel lived there. Kathy was there with us during the workdays. Our dog Ty was there with us too. We were, in the technical legal sense, homeless. We showered at the local Life Time Fitness, ten or fifteen minutes from the office, on whatever schedule we could fit between meetings. Torel’s bed was placed under the conference room table — the same conference room table where I took client calls during the day. He pulled his bedding out at night, slept on the floor, and rolled it back up in the morning so the meetings could happen the next day. He was thirteen years old, deep in middle school. He was old enough to know that other kids did not live in offices. He was old enough to be embarrassed if he was going to be embarrassed. He was not embarrassed. He thought it was fun. He thought the bed under the conference room table was the most interesting bedroom any of his classmates had. The boy who had thought sleeping in the office during late nights with his mother was cool grew into the middle-schooler who thought living in the office was an adventure. Same disposition. Same boy.

I do not think anyone outside our small operating circle knew. The agency presented as an agency. The clients did not know. The vendors did not know. The people who walked in to the office during business hours encountered a working agency with a desk and a conference room table and a phone, and they did not know that the conference room table was, at night, the structural anchor of a small boy’s bedroom. The hiding was deliberate. I was not interested in being the founder who had a story about being homeless. I was interested in being the founder who shipped good work for clients. The personal-living-situation was the variable I had chosen to eliminate so that everything else — the work, the people, the company — could have all of me. The cost was paid in private. The benefit was paid in business.

I want to put one piece of verification on the page before I close this passage, because the kind of hardship I am describing could read as retrospectively dramatized by the founder who lived through it. Yesterday — the day I am writing this paragraph — Kathy texted me when I asked her if she remembered the period. Her text was, verbatim:

“I remember it was around May – September 2012? It was not so bad. Kinda fun.”

That is Kathy’s posture on the technically-homeless year, in her own words, fourteen years after we lived through it together. “It was not so bad. Kinda fun.” The former Physician Assistant who had given up clinical medicine to come work at my agency, who had bought 3% equity out of her own savings, who was sleeping in the same Richardson office I was sleeping in with my son and my dog — looks back on the period and remembers it as kinda fun. That is who Kathy is. That is also who CI Web Group has been at its best across two decades. The work was hard. The conditions were unusual. The people who chose to be there chose to find the cool thing in the situation and operate from there. That is not a posture you can fake. That is what was actually in the room during those five months in 2012, and it is what has been in the room ever since.

That year of living in the office is one of the most distinctive single decisions of my professional life. Not because the hardship was unusual — plenty of founders have done harder things — but because the decision was deliberate. I did not become homeless because I had no other option. I became homeless because I had decided that one hundred percent of my efforts and money would go into the business, and the cleanest way to enforce that decision was to remove the line item that was costing me the most. The line item was where I slept. The decision was to remove the line item. The result was five months in the office with my son and my friend and my dog, building a company that would still be here fifteen years later. That is the kind of thing entrepreneurs will do to accomplish their dreams. Some entrepreneurs will not do it. Some entrepreneurs would not even consider it. I considered it, and then I did it, and then I never looked back.

Some time after that year, I made the second decision in the same philosophy. I eliminated the office entirely. I never opened another one. The office that had been my home for a year became, by my own decision, no office at all — not relocated, not consolidated into a smaller footprint, not replaced with a different building. Eliminated. Gone. CI Web Group, from that point forward, operated as a fully virtual agency. Every meeting happened on a screen. Every project happened in shared cloud infrastructure. Every employee worked from wherever they happened to live. That decision — made years before the rest of the industry started taking remote-first operations seriously — is the structural reason CI Web Group is what it is in 2026. The agency has been able to hand-select talent across twenty-two states because we have not been constrained, for the last decade-plus, by the geography of a single office. The best account manager for a Pacific Northwest contractor lives in Oregon. The best AI engineer happens to live in California. The best graphic designer happens to live in the Midwest. The best operations director happens to live in Texas. Every one of those people is on our team. None of them would be on our team if I had built a physical office and required them to come to it. The technically-homeless year was the moment I gave up my personal living situation for the business. The office-elimination year was the moment I gave up the business’s physical anchor so that the business could operate at the scale the work required. Two decisions, one philosophy, fifteen years apart. Both were about resource allocation. Both were about the same thing: removing the constraint that was costing the most so that everything else could have the most.

Some context. Fossil — the watch and accessories company — had relocated me to Dallas, Texas in roughly 2000, when Torel was two years old. The relocation was the move that took me away from the Pacific Northwest and away from my parents, who were devastated to see their only daughter and only grandson leave Washington for a city two thousand miles south. They never said so directly. They were the kind of people who let you go where you needed to go. But I knew. I lived with knowing for the next twenty-six years. Some of what I have tried to do in the most recent chapter of my life — the part where I now own a home on Greenlake in Seattle, walking distance from my mother and five minutes from my son and grandson — has been my attempt to close that distance. That is a story for a later chapter. The relevant fact for this one is that by the time I founded CI Web Group, I had been a Dallas resident for roughly five years, and Dallas was where the agency was born.

By the time I left Fossil and went out on my own, I had a goal I had set myself years earlier: to be an entrepreneur by the time I turned thirty. I had been holding the goal on the calendar the way my father had held his shipping calendars on the calendar — not as an aspiration but as a deadline. I left corporate just in time. The week I walked out the door, I was still inside the window of the goal I had set myself. By a small margin. But by a margin.

As Torel’s only parent launching an agency, the timing was, to put it mildly, not ideal.

The first few years were hard in ways the cleaned-up agency history never tells. I lived in the office. Not metaphorically. Literally. The space I had rented to be the agency was also the space I slept in. I went broke getting the business off the ground — the kind of broke where the calculations about what to spend on what get made every morning, in detail, with the kind of clarity that comes from not having any margin for error. Torel and I showered at the local 24 Hour Fitness. That was where we kept our toiletries. That was where we got ready for school in the morning. That was the family bathroom for our first two years inside CI Web Group.

Torel’s bedroom was under the conference room table.

He thought it was cool.

I want you to register that, because the small boy whose mother had brought him from a stable corporate household to a half-built agency office did not interpret the situation as deprivation. He interpreted it as an adventure. That posture — *this is cool* — has been Torel’s posture for his entire life. The boy who could see the cool thing in whatever situation he had been handed is the same person who, fifteen years later, would be one of the three voices on the phone the night ChatGPT launched, calling his mother in Kauai because something had just changed and he could not wait to tell her about it. Same boy. Same disposition. He has always been a kid who could see the cool thing in the situation he had been handed.

Under no circumstance would I quit.

That is the sentence that defined the first three years of CI Web Group. Not as a slogan. As an operating constraint. I had a son to raise. I had a goal I had set myself by thirty. I had walked out of corporate. I had moved my child into an office. I had told my parents, two thousand miles away, that this was the right call. The only way any of those decisions made sense was if the agency worked, and the only way the agency was going to work was if I did not quit, no matter what happened in the next three years. So I built that posture into the operating architecture of the company. Quitting was not on the menu. Slowing down was not on the menu. Looking for an exit was not on the menu. The menu had one item: keep going, get the next client, do the next piece of work, sleep under a desk if you have to, shower at the gym if you have to, raise the boy under the conference room table if you have to, do not stop.

I did not stop.

There were no employees in those first three years. There was no office in the modern sense — there was a rented commercial space that was operating as a working agency, with a small boy spending most of his after-school hours and weekends inside it because his mother was the only operator and his mother was always there. There was a desk in the front room, a phone, a laptop, a conference room table where meetings happened, and a single owner-operator who was the salesperson, the strategist, the project manager, the copywriter, the SEO consultant, the analytics person, the client services rep, the bookkeeper, the late-night customer support line, and the morning lunch-packer. I was the agency. I was the company. I was, at the same time, the only parent the small boy in the room had.

I worked the way my father had worked. Late nights. Long hours. Whatever it took. I did not have my father’s twelve-foot ladder pointed at Saturn, but I had a desk pointed at a screen, and the screen was, in its own way, the same kind of thing. It was a portal to a part of the world that most of the people around me could not yet see. The trades contractors I was talking to in those years did not understand what I was doing. Some of them thought it was a scam. Some of them thought it was magic. Some of them thought it was a hobby. None of them, in 2006 or 2007, were treating digital marketing as a serious operating expense. They were treating it as a curiosity. An experiment. A favor I was doing for them in exchange for a check that, in many cases, was about the size of what they would spend on a single newspaper ad.

I did not mind. I knew what was coming.

The way I knew what was coming was the same way my father had known. He had seen the MICR encoder land in the banking system in the 1970s and known, instinctively, that machines reading text was going to be the foundation of every commerce system that came after. I had seen the Mosaic browser land in 1993 and known, in a less articulate way, that the internet was going to swallow every directory and yellow pages and printed catalog in the world. By 2006, I knew that local search was going to be how people found contractors, that Google rankings were going to be the new word of mouth, and that the contractors who got their websites and their listings and their reviews working in time were going to eat the lunch of the contractors who did not.

I was not selling marketing in those years. I was selling the future. Most of my clients did not know that was what they were buying.

By 2008, the agency was beginning to look like a real business. I had a few employees. I had a real office — a separate one, with no conference room table doubling as a child’s bedroom underneath it. I had clients who were paying real money for real work and seeing real results. The operating model that would define CI Web Group for the next fifteen years was starting to take shape. We did not require contracts. Clients owned their own assets — the websites, the domains, the content, the analytics accounts. We worked on a month-to-month basis and trusted that if we did good work, the clients would stay, and if we did not, they would not. The agency industry, in 2006, did not work that way. The agency industry, in 2006, locked clients into multi-year contracts and held their assets hostage. We did the opposite of what the agency industry did. We trusted our work.

That trust, twenty years later, is still the operating principle of CI Web Group. We have served some of our largest clients for fifteen and twenty years, on month-to-month terms, with full asset ownership the entire time. The reason they have stayed is not because they were locked in. The reason they have stayed is because they have not wanted to leave. That is the only kind of relationship I am interested in building. It is the only kind my father had with the publishers who shipped his Apple II software. It is the only kind worth having.

The Thirteen of 2008

In November of 2008, something happened that turned CI Web Group from a working agency into a real one.

On November 13, 2008, Daikin’s North American operation selected CI Web Group as a preferred digital marketing partner.

November 13, 2008 was Torel’s tenth birthday. Ten years to the day after he was born, Daikin signed the partnership that would scale CI Web Group from a regional digital agency into a national operator in the trades industry. The date was a thirteen. The decade-mark on Torel’s birthday was the moment the pattern stopped being a coincidence in my mind and became something I started watching for.

I want to take you through what the Daikin relationship meant, because it is one of the structural foundations of everything CI Web Group has been since.

Daikin was, and is, the largest HVAC manufacturer in the world. Japanese-headquartered, global, with billions in annual revenue and a North American market presence that touches nearly every commercial and residential HVAC contractor on the continent. When Daikin’s North American operation selected CI Web Group as a preferred digital marketing partner on November 13, 2008, it was the moment a small Dallas agency run by a woman who had been raising her son alone for a decade became, in the eyes of the trades industry, a serious operator at a national scale.

That decision was made on the same date my son was born. Ten years to the day. I do not know how to explain what that felt like, on the day the partnership was confirmed. Torel was turning ten. The agency was about to triple in addressable market overnight. And the calendar had handed both events to me on the same square.

[PLACEHOLDER — Jennifer to fill in: the actual scene of the Daikin signing. The meeting. The phone call. The handshake. Whatever specific moment captured the decision being made. If the decision happened over a longer period and there is no single scene, that is fine — the chapter can describe the cumulative weight of the year leading up to November 13.]

From November 13, 2008 forward, CI Web Group was a different company. We had Daikin behind us. We had Mitsubishi behind us. We had two of the largest names in the trades industry endorsing us as the agency they trusted with their contractor network. The agency was no longer a small consultancy with a handful of accounts. It was an institutional partner to the trades industry, and the contractors who joined us in the years after 2008 joined because they had heard about us through the most credible channels in their professional world.

We grew.

[PLACEHOLDER — Jennifer to fill in: a sense of the growth trajectory between 2008 and 2015. Approximate employee count by year. Approximate revenue trajectory if you are comfortable disclosing it. The names of any other major partnerships that defined that period. The specific turning points where the agency moved from one phase to the next. This is a place where rough numbers are better than no numbers — the reader needs to feel the trajectory.]

The Strategic Exit

Around 2024, I made a decision that, at the time, looked to most of my peers like I had lost my mind.

I exited paid search. I exited social media management. I exited two of the largest, most profitable, most rapidly-growing service lines in the digital marketing agency industry, in the year that those service lines were booming, and I told my team, my clients, and my industry that CI Web Group was going to focus on building our own web infrastructure, local SEO, AI search, and agent optimization — four years before that was even a thought in anyone’s mind.

To anyone watching from the outside, the decision did not make sense. PPC was a forty-billion-dollar global market in 2024. Social media management was a thirty-billion-dollar market and growing. The agencies that were riding both of those waves were the agencies that were getting acquired, going public, and ending up on the conference panels. Walking away from those service lines, in 2024, looked like walking away from money.

I want to tell you why I did it, because the reason is the same reason my father walked out of a warehouse on Bill Gates and Paul Allen, and it is the same reason I walked out of a six-figure executive track at twenty-eight.

The reason is that I could see what was coming.

Paid search and social media management, by 2024, were both about to be transformed by AI in ways that would make them either commoditized or extinct. Paid search was about to be eaten by automated bidding agents that would optimize ad spend better than any human could. Social media management was about to be eaten by generative content tools that would produce platform-specific posts at a scale and quality no agency human team could match. The work that was, in 2024, profitable for agencies because it required armies of specialists, was about to require almost no specialists at all. The agencies that built their growth on those service lines were building their growth on sand.

The work that was not going to be commoditized was the work that required deep operator knowledge of a specific industry, deep relationships with specific clients, and deep understanding of the strategic positioning of those clients in their local markets. That work was organic search, local search, brand authority, content strategy, and the orchestration of all of those things into a coherent presence that an AI agent on a contractor’s phone could rely on as ground truth. That work was going to become more valuable as AI got more capable, not less.

So I exited the work that was going to commoditize, and I doubled down on the work that was going to compound.

[PLACEHOLDER — Jennifer to fill in: the specific moment or quarter when you made the strategic exit decision. Whether it was triggered by a particular event, conversation, or product release. Who you told first. What the team’s reaction was. What the client reaction was. What revenue impact the exit had in the first six months and the first year. If the exit was a multi-step process across multiple quarters, the chapter can walk through those steps.]

The exit cost us, in the short term, several million dollars in annualized revenue. It cost us some clients who were not ready to make the same bet I was making. It cost us some employees who decided their careers were better spent at agencies that were still riding the waves we were exiting. I did not enjoy any of those losses. I also did not regret a single one.

Because I had been trained, since I was eight years old, to do the thing that was about to be true rather than the thing that was currently profitable. My father had walked away from a Bill Gates partnership because his philosophy did not match Microsoft’s. I had walked away from a corporate executive track because the work did not match who I was raised to be. And in 2024, I walked away from two service lines that the rest of my industry was riding to the top of, because I knew — the way my father knew — that the top of that wave was going to break in a place I did not want to be standing.

Eighteen months later, the wave broke. The agencies that had built their growth on PPC and social media management were beginning to feel the displacement I had seen coming. Automated bidding had begun to eat the margin out of paid search. Generative content tools had begun to eat the value out of social media management. The agencies that had not made my exit were now scrambling to make it eighteen months too late. The agencies that had made it earlier — a small handful of us — were already on the next wave.

I was raised to be early.

What CI Web Group Actually Is

I want to close this chapter with a direct answer to a question I get asked, in some form, at every conference and on every podcast and in every introductory meeting.

The question is: what is CI Web Group, actually?

The answer has changed three times in twenty years, and the changes have not been arbitrary. They have been the same kind of changes my father’s career underwent in the previous generation. Same instinct. Different decade.

From 2006 to roughly 2015, CI Web Group was a digital marketing agency for trades contractors. We did websites, SEO, content, local search optimization, and the operational support that turned a contractor’s online presence into a real business asset. We were good at it. We grew. We built an industry reputation. We became the agency that the supply chain trusted.

From roughly 2015 to roughly 2023, CI Web Group was a digital marketing agency for trades contractors that was beginning to integrate AI into its core delivery. We launched what we called Cortex AI — our internal AI-augmented SEO methodology — well before the rest of the agency industry was using AI for anything beyond chatbot widgets on contact pages. We built AI Local, our AI-powered local search optimization product, which is now deployed across hundreds of contractor markets. We launched Pulse, our AI-driven content production system, which produces market-specific authority content for our clients at a quality and scale that human-only teams cannot match.

From roughly 2024 to today, CI Web Group is something different. We are an AI-orchestrated marketing operating system for trades contractors, with HydraOS as the orchestration layer, MCP endpoints connecting our agents to industry data sources, the Synapse knowledge graph organizing what we know about the contractor industry, and OnePath.AI as the contractor-facing agent that lets a small business owner have a real-time conversation with their entire marketing operation. We still do the work we did in 2006 — websites, SEO, content, local search — but the work is now done by a coordinated network of AI agents that operate at a scale, speed, and quality that no traditional agency can match.

That is the technical answer.

The human answer is simpler.

CI Web Group is the agency that the trades industry has trusted for twenty years. It is the agency that has been there for HVAC contractors when their websites went down, plumbing contractors when their rankings dropped, electrical contractors when their phones stopped ringing, roofing contractors when their leads dried up, and garage door contractors when their search visibility evaporated overnight. It is the agency that has stayed when other agencies have moved on, that has held its month-to-month terms when the industry standard moved to multi-year contracts, that has let clients own their own assets when the industry standard was to hold those assets hostage, and that has refused to chase the profitable wave when the profitable wave was about to break.

It is the agency my parents would have built, if my parents had built a digital marketing agency in 2006 instead of a group home for developmentally disabled adults in the early 1970s.

Same instinct. Same operating philosophy. Different industry. Different decade. Same answer.

On January 13, 2006, I started a company. I did not know, on that day, that the company would still exist twenty years later. I did not know that it would have served thousands of contractors. I did not know that I would, eventually, be running the AI transformation of an entire industry. I did not know that my son would grow up at the agency. I did not know that my husband would join after twenty-five years in the Army. I did not know that the love of my son’s life would become the senior AI vibe coder rebuilding our delivery stack from the inside, or that his childhood best friend would be working alongside her on the same systems.

I did not know any of that. I knew one thing. I knew the trades were going to need a partner who could see around the corner, and I had been raised, since I was eight years old, in a garage with a twelve-foot ladder pointed at Saturn, to be exactly that kind of partner.

The first thirteen of my career was January 13, 2006.

Everything else has followed from it.