All Together Now!
I’ve been asked to write a founder story so often that I decided to write mine down, if only so I can tell people roughly the same story every time, which is more difficult than you’d imagine when under pressure, or under the influence.
The Plane-Crash Epiphany
I hate flying over the ocean — even the phrase “transatlantic flight” makes sweat pour out of the wrong parts of me (like my ankles). I can’t sleep, can barely read, and I hate drinking alcohol because shortly after I get off the plane it’s morning in London and I’ll be in front of a room full of people having to sell them on something… or not looking right when crossing a street (a non-trivial problem, as programmers say).
In the fall of 2000, as the NASDAQ started its violent, slow-motion crash, I boarded a plane at JFK, on my way to London. I had gotten married just a few months ago, my wife was pregnant and we were running out of money, even though I’d created one of the earliest high-scale, Internet time and expense applications, and we had Amazon.com, JPMorgan Chase, and several high-profile UK clients. I had been going back and forth to London for a year since launching Staffsheets.com (later Workplace Software), while writing code, selling, training and doing all the things a startup CEO did back then.
So I was already pretty sweaty as I walked toward my gate: married, broke, wife pregnant, tech stocks crashing, pretty sure I’m about to die in a crash… Before I boarded the plane I bought some magazines, including one with lots of high-minded advice for people who ran real companies. When I flipped through it, I noticed there were a bunch of blank white pages at the back — either a printer’s goof or a bonus for people who wanted to take notes.
The minute the door of that airplane closed, I started my normal sweating routine, so I grabbed that magazine and started doodling on those blank pages to relax me. It didn’t work — I suddenly had an overwhelming sense of doom. I was sure our plane was going to go hurtling down into the Atlantic. I panicked, thinking about my wife, and about my company. I knew I had most everything for the business organized and shared with the key people, but I realized my wife didn’t have all kinds of vital information, so I started listing everything she would need to know after I died in this crash.
Here’s roughly what I wrote down:
- Files — will, insurance, car title, the deed for our apartment, tax information, copies of bills
- Financials — bank accounts, eTrade account, Collegebound (for our daughter), etc.
- Insurance — Life insurance paid by my company, my life insurance, a policy my parents had taken out for/on me, car insurance, homeowners insurance, health insurance, warranties. How much did all the stuff we owned cost, had I paid all the bills?
- Assets — home, car, weekend home, furniture, computers, TVs, appliances.
- Health records — all the things we were keeping track of about ourselves, about our yet-to-be-born daughter, and everything we had learned about our family history.
- Contacts — insurance, banks, doctors, relatives, utility bills, friends, babysitters, passwords, good restaurants, and on and on…
- Photos — (This was pre-Picasa, iPhoto and the Facebook).
- Other — endless notes, lists, post-its, business cards, menus, you name it.
After an hour of writing all this down, I realized it was a system, a crucial system, the network of data that defined my family life. So I started drawing that system. I created one crazy sketch after another about how this whole thing operated, what the data looked like, how the parts connected, even a user interface. I filled up nearly all 12 of those blank pages, front and back.
By the time we landed, I knew this was the application I needed to build, my life’s work rolled into one neat interface. I called it Life Work.
For weeks my wife and I negotiated with a woman who had a small candle business who owned the web domain LifeWork.com, but she refused to sell, at any price. Our next name wasn’t quite as catchy, but appealed to me as an enterprise resource planning software geek: Family ERP. (I still own the domain, if you want it.) I would eagerly explain to confused-looking people that I was designing an ERP system for their family. They’d politely ease away from me. And yes, sometimes run.
But I kept pushing. We formed a team, my wife and I. We corralled a really smart Australian guy (Hi, Mark!), and my older brother, one of the world’s great enterprise application wizards. We met every few weeks and talked about our ideas. Finally our thinking was clear enough and we could nearly explain the idea to a normal person. We even had a long and promising call about funding with some people at Intel Capital.
But, as is the case with most side projects, this one remained a side project, and each of us put all our energy into our day jobs.
9/11
A few months later, my wife and I were asleep when the planes smashed into the World Trade Center Towers on September 11, 2001. We lived downtown, about 20 blocks away, and our newborn daughter was squashed between us, also asleep. We were awakened when my sister-in-law called from L.A., worried about us. We turned on the TV, saw the towers on fire, then went outside. Thousands of people were in the streets, looking downtown, wondering what was going on. I knew I had to get my team at work organized in case we lost access to our site and my wife was desperate to get our newborn out of town, so I started walking east, toward our garage. When I looked downtown through the arches in Washington Square Park, I saw the towers collapse.
It took me a very long time to persuade the FBI to let me get my car, because they had taken over the garage for a staging area. I had to call in a big favor (very long story) and we weren’t able to leave Manhattan until early that evening. Driving on the Long Island Expressway, it seemed like we were the only car going east. It was like we were the lone survivors of a nuclear explosion.
Family ERP came back to life that night. I became obsessed with how to create a living and breathing system that lets the whole family (even the extended family) communicate and share all their important stuff on a daily basis. I began to see that my mission was getting families to operate more efficiently and democratically. I became a zealot about this subject, haranguing friends and sometimes even strangers, pleading with them to start working together. I started to share all kinds of little systems and files, and books, and stored as much as I could online for my family to see. I also started to think about how to connect my parents, my brother, and other extended family, to form a family-to-family network.
The project eventually lost momentum again — we sold Workplace to a large Hollywood payroll company (which collapsed in a bizarre, Hollywood-like ending after I left), and I went right into another enterprise startup. But rarely did a day or two go by without my doodling about another feature for the family, or talking to someone about how they manage all this stuff, and whether they worry about it. I learned that nearly everyone does worry about it, and wants to manage their family life more efficiently, but it’s just too hard. Like this LifeWork — Family ERP project, families usually try a few things and then go back to their day jobs and their normal routine.
In Sickness and in More Sickness
In the summer of 2010, I was driving from New York to Connecticut with my father-in-law when my wife called to tell me she had breast cancer. Her father and I both tried to be cool (he’s a very macho guy), but we were both terrified. I had no experience with a medical crisis and no idea what to do next.
Fortunately, my wife’s uncle is a prominent cancer researcher, a Nobel-prize winner, in fact, and was president of one of the best cancer hospitals in the world. It was like having your Tesla break down and being able to call Elon Musk. Even with that huge advantage, my wife had a terrible ordeal. We had three kids by then, I was (again) running a startup that was (again) running out of money, and she had to undergo three surgeries, and six months of radiation. I was freaking out, but she was stoic, strong.
She’s totally fine now, and the healthiest person I know, but the chaos that process inflicted on our lives was awful. The paperwork alone was overwhelming. The costs, keeping track of every bill, the many appointments, all the doctors, the endless files and tests… She had to become an expert on all health administration, self-diagnosis, scheduling and communication protocols, to say nothing of handling the logistics of babysitters, grandparents, kids, and everything else a working mom has to deal with every day. We found ourselves again trying to hack together a family operating system of sorts.
In the late winter of 2011, I broke my right wrist sledding with my two young boys. That night, slowly then suddenly, the pain became unbearable. But when I got it X-rayed, the doctor couldn’t find anything wrong. “No,” I said too loudly, “I am positive it’s broken!” He gave me that look, strapped a wrist brace on me (to shut me up), prescribed some pain medication, and sent me away. But the pain didn’t go away. And then a strange thing happened: the pain moved to my left wrist. “Hmm,” my wife said. “Probably not broken.”
I made another appointment, and by the time it rolled around, my neck was “broken” too, or felt like it. Obviously, there was something very wrong.
It took several months to diagnose it but I finally realized I had a pretty aggressive autoimmune disease called rheumatoid arthritis. Unfortunately, it’s pretty common, but it’s a little unusual to get it as early as I did and for it to be as debilitating as mine was. By the end of 2011, I could barely get out of bed, could barely walk. And I had difficulty picking up my little kids to give them a hug. I also couldn’t run, play golf, or do hardly anything I liked to do without doping myself up with a fistful of pain medicine.
After two years of this, I too had become an expert on all the health-related processes my wife had just battled through: appointments, bills, contacts, files, insurance, x-rays, endless lists (everything I ate, drank, did), notes (follow-ups, recommendations). I was overwhelmed by how much I had to track.
A New Life, and Work
Early in 2013, I hired a personal trainer, because I had not exercised in over three years. He asked me that first day what my goal was. I said it was pretty simple: I wanted to get healthy for my family. I explained in some detail, that I had an important project to do, and in order to do it I needed to be healthy again. I told him it was a project for my family. For every family. I said it was something I’d been putting off for 13 years. Something I’d been doodling on, talking about, planning for ages. He listened carefully to my story and then told me he could fix me. I was pretty skeptical, but he did it.
I spent the next nine months going from barely walking to jogging to running, to lifting weights, to doing things I never thought possible. I dropped about 50 pounds. I started taking my wife’s advice on eating and exercise. I moved part of my wonderful software team from Connecticut to Austin, and we started full-time on this project. Stretch.
I built Stretch for my family, but your family is welcome to use it too. And you don’t have to go through the same sort of ordeals my family went through. Stretch is pretty useful just for staying in sync or for keeping track of the vital stuff like health and wealth. And it’s basically what I sketched out in the back of that magazine 16 years ago, but now it’s mobile, and it can be used by the whole family, every day. It’s still in beta, and it’s still evolving (like all software), but pretty soon, if we get a little bit lucky, it’ll be as great as I imagined it.
If you have an iPhone, give it a try:
Thanks for reading. My best to you and your family.
Darren Reid
