Entreprenurial Steve in Profile

While working for an Internet startup, our founder, CEO, and perhaps most importantly, boss, was a dynamic, unusual personality whom I’ll call Steve. Entreprenurial Steve.

A bundle of contradictions, in some ways I felt perfectly aligned, and in other ways, his thinking was so foreign to me that I couldn’t make heads nor tails of it. In all the time we worked together, for example, Steve never let anybody else pick up the check for a meal, and he was generous about inviting us out.  During a period where nobody in the company had any money and we were essentially working for free, Steve didn’t hesitate to take us to lunch every day, and often out to dinner.

Steve had (at least) two BMW’s, which seemed like kind of a status thing, except that Steve wouldn’t hesitate to loan them to whoever needed them.  Our secretary borrowed one and managed to total it in the parking garage (yes, I’m still unclear on how this can be accomplished) and Steve simply shrugged it off, saying, “It’s only a thing.  The important thing is if you’re okay.”

Yet, when I stopped on the street to hand some cash to a homeless person with a sign, Steve was completely baffled.  “Why would you give your money to that guy?  He’s not doing anything for you.”

“Five dollars means a lot more to him than it does to me,” I tried to explain.  “He needs it more than I do.”

“That’s crazy,” said Steve, shaking his head.  “I’m sure you can do something better with that five dollars.”  Weirdly, he handed me a five.  “Here,” he said.  “Don’t give this away.”

At times, it seemed that Steve held the company together through sheer force of will, when paychecks were bouncing and vendors weren’t being paid, his optimism and willingness to do anything to get it done for our customers was infectious, truly believing that our next sale would put us on firmer financial footing (which it always did, for a while) and that stability and prosperity was within our grasp.

Steve always seemed to know who to pay.  Starting, I suppose, with the lawyers.  “Get the most expensive lawyers you can,” Steve once explained to me.  “Even if you have to skimp on everything else.”

Our lights were always on.  Our Internet connection always worked.  Our phones always worked.  Other than that, I’m not sure anybody was paid at all.

Occasionally, a process server would come by, and Steve would invariably be gone.  Otherwise, he always seemed to be around, and I have no idea how he managed it.

Although clearly uncomfortable with kids, my precocious daughter asked him if she could use a computer.  Without hesitation, Steve handed her his personal laptop, explaining that he was going to a meeting and wouldn’t need it until the next day.  She dutifully returned it to his desk before we left.

The next day, we had a meeting with a potential customer.  Our presentations and servers were all online, so there was little prep necessary except for connecting to the Internet.  Steve booted his laptop, and instead of the familiar Windows chime, the room was treated to:

“Uh ohhhh!” from the Teletubbies.

A number of people in the room clearly had kids.  Steve was thrown off kilter, but shook off his utter mortification and made an excellent presentation.  (We got the deal, and I suspect the unexpected presence of the Teletubbies made us seem more human than slick and polished.)

A week later, my daughter asked to borrow Steve’s laptop.  Without hesitating, he handed it to her, but paused before letting it go.  “Try not to leave anything in the drive this time.”


Golden Age of the Internet Startup – Part 2

With a few sales under our belts, we packed up what little equipment we had, and moved to our new space in a downtown commercial high-rise, where we had an entire floor to ourselves.

An entire floor is a huge amount of space. There were ten of us now, including sales, marketing, etc., in a space that could hold 300. The space was fully furnished, and included a boardroom with a view, where all of us could sit, and have ample room for 20 more people.

This wasn’t unusual for any dot-com era startup, but perhaps it was unusual for one without venture capital funding. Bill explained that we hoped to expand quickly, and that more importantly, customers should be able to visit a place that inspires confidence.

One walked off the elevators into a large, well appointed lobby with leather seats and a stainless steel version of our logo on the wall, up to a reception desk, behind which was a glass wall displaying our opulent (and usually empty) boardroom, where one looked through it onto an expansive view of the city. From there, one could go right or left to weave through cube farms before reaching either outer wall, all floor-to-ceiling glass. The few employees scattered about and a few well placed plants and personal items give the impression that a large office had just gone to lunch, or is sequestered in meetings somewhere. You’d probably end up at a huge, well appointed corner office to meet the CEO, or perhaps the head of marketing, or the CTO, or the COO — there were four corners, after all.

Bill was right — the entire place spoke of money and confidence, without being too opulent. On the occasions when customers did come by, we avoided an empty look by using 3-4 cubes each, and inviting friends over to sit around for lunch. (Nobody would ask if all the people in the office actually worked there, but we certainly would not have lied if it came up.)

Along with the cubes and chairs came a big PBX system with hundreds of phones, handy partly since we were so far away from each other. This was in our full server room, where Bill invested in two racks full of servers, along with new PCs for everybody, plus a bunch for empty cubes.

None of the equipment was unused. For every empty cube with a PC humming under the desk, there was a system running tests, compiling code, copying backups, running competitor’s systems, providing remote access, and so on. In addition to selling our main line of software, we also did odd bits of consulting in order to provide the company with income — this included setting up and integrating competitor’s systems (which was handy for a number of obvious reasons) as well as odd jobs like data mining for grocery stores and other utterly unrelated technical tasks.

I sat in the back, near the server room, which gave me a unique view and made it easy to concentrate on writing code.

On the floor below us was a radio station, which we didn’t notice at all our first few months — then they either changed formats or management, or both, and suddenly it was apparent that my office was directly over some kind of listening or sound booth — and during the day, they started cranking up the noise so that not only could it clearly be heard in our office, it was hard to speak to somebody in the same room. I called the building management to complain.

“I’d like you to do something about our downstairs neighbors,” I shouted over the din. “We can’t hear ourselves think up here.”

“I can’t understand you,” said the building manager (a dour woman we’ll call Leslie.) “Maybe you could turn down your music.”

“That’s really my point,” I shouted. “That’s not our music. It’s coming from downstairs.”

“I’ll be right up,” said Leslie, lying through her teeth.

A couple hours and a few phone calls later, Leslie appeared. Perhaps coincidentally, but probably not, the music had been turned off moments before she marched up to my desk.

“I don’t hear anything,” Leslie told me, in an accusatory tone.

“Well, obviously you did when I called, since you complained you couldn’t hear me over the music,” I explained.

“That could have been anybody’s music,” said Leslie dismissively.

This seemed pretty disingenuous and odd, but this same pattern repeated itself a few times, before Leslie actually appeared in my office while a deep bass thump was still shaking my furniture.

“I don’t hear anything,” said Leslie.

“What?” I said, shouting over the noise.

“I said, I don’t hear anything,” she shouted. “I can ask them to turn it down, I guess, but I don’t hear any music at all.”

I didn’t know what to say at this point. I talked to our business manager later, who mumbled something about a possible dispute with the lease. Were they trying to make us leave? I’m not sure, but I was beginning to hate Leslie.

I once had a friend with the curious habit of jumping up in moving elevators, landing with stiff legs. This created a booming sound that resonated throughout a building, and he’d nonchalantly walk off the elevator to nervous stares of people waiting to get on, some of whom would think better of the idea.

With this in mind, I brought in a bowling ball. Next time the music started up, I ceremoniously dropped it on the floor, right above where the music seemed loudest, which was near the server room on a little bit of linoleum floor (the rest of the office was carpeted.) It worked better than I could have imagined — it sounded like the building had been hit with a wrecking ball, sending a BOOOOOM that resonated through the floor and walls. I did this a few more times before the music stopped, and put the ball into a desk drawer.

Leslie showed up a moment later. “Are you guys doing any construction up here?”

“Heavens no,” I told her. “Surely we’d notify the building.”

She eyed me suspiciously. “We’ve had complaints from the floor downstairs, the noise is interfering with their radio broadcast.”

“Is that so,” I mused. “Well, I don’t hear anything.”

She stood, listening, and looking around, presumably for signs of construction equipment.

“I said, I DON’T HEAR ANYTHING,” I shouted at her.

She left in a bit of a huff.

The radio station’s volume got loud a few more times, but a few drops of the bowling ball were enough to stop it quickly. Our downstairs neighbors seem to have quickly learned the cause-and-effect relationship, and the bowling ball became an ornament on my desk.

Leslie dropped by one day on an unrelated matter and noticed it, and appeared to connect the dots all of a sudden.

“Were you dropping that bowling ball on the floor? Because I have to warn you, that would be unacceptable,” she lectured. “I could hear something like that all the way on the first floor.”

Really? Awesome.

“Madam, that’s a valuable ball,” I replied. “Besides, I’m certain it would cause quite a bit of noise, which would be completely unreasonable in a professional office environment. It might be more appropriate for some kind of party floor with loud music. Do you hear any music?”

She ground her teeth a bit, but said nothing. We didn’t have any more trouble from her or the neighbors for the duration of our stay.


Golden Age of the Internet Startup

Y2K was a weird time for many in technology fields.  For my part, I was in charge of an e-commerce team at the time that many companies were just beginning to realize the importance of having a presence on the web at all.  Revenues for my brick-and-mortar company were just topping $1 billion…  then overnight, one of our biggest customers made a few dramatic changes, and as a company, we had to shrink to about a quarter of our size to match our wildly decreased revenues.

As the fledgling wing of the business, the e-commerce team bore a disproportionate amount of the downsizing effort, so I laid off most of my very large team.  Another round later, most of my considerably smaller team were laid off.  By the third or fourth round, I’d decided it would be better to taste the riches of the dot-com era than preside over a rapidly-dwindling department, and laid myself off.

Within a week, I had about a dozen job interviews lined up — the availability of dot-com money was in full swing, companies were paying a premium for barely-competent java programmers, and my Vice President of e-Commerce title placed me in demand.  I rejected most of them for various reasons:  I didn’t think much of their technology, or their business, or didn’t have enough control, or just plain didn’t like the interviewer — within two weeks, I settled on a company that seemed to have everything going for it:  supply chain software, capital provided by a consulting business, a foundation for a product, domain skills, and a fair (but not exorbitant) salary.  Perhaps even more important was the contagious enthusiasm exuded by the founder, whom we’ll call “Bill.”

Bill hired two people right away — me, as the Chief Development Officer, in charge of building and supporting our products, and “Jeff,” as the Chief Technical Officer, in charge of infrastructure, IT, and everything else.  Jeff showed me the clause in his contract that included a foosball table in the lounge — something I neglected to ask for — but presumably, we’d have the same lounge, so I wasn’t about to complain.

Our first offices were temporary space with Regus.  We had four desks or so, reception, internet service — a whole office presence.  Since it was shared office space, we rubbed elbows with other Internet startups, cheap lawyers, and a handful of dismal people doing god-knows-what, whom I’d notice carrying a paper lunch bag into their office, and sitting at a desk all day by themselves.  I never saw them with computers or on the phone, so I imagined them spending their waning years pretending to go to a job that no longer existed.

A few years earlier, when I worked for a company on behalf of the CTA, I was shown an empty room with four older people in it with computer printouts and those old adding machines with the crank handles.  It was explained to me that due to their seniority, they effectively could not be laid off, nor could they be forced to train for other jobs, but their skills were utterly obsolete.  So they were put to work verifying account spreadsheets printed by the mainframe, which was deliberately pointless and mind numbing work.  They were not allowed to read books, and had to be strictly on time every day and take only prescribed breaks, or be fired.  Meanwhile, they carefully ran their crank machines, their work destined immediately for the trash bins, waiting out their retirement clocks.  I couldn’t help thinking I might go insane first, or at least beg to be retrained for something.  Anything.

I was reminded of this every day at Regus as I walked past the office of a little guy with a moustache, who didn’t ever have anything on his desk but his lunch, and seemed to spend most of his time looking at a spot on the desk.  I’d flash him a sunny smile and wave, and I might get a half-hearted smile in return, if I was acknowledged at all.  I called him “Willy Loman” and looked forward to days when his door was closed.

We didn’t have dedicated connections or server hardware, so I set up web and email servers in my basement, which had pretty decent connectivity.  The old consulting wing of the company was based in California (with a few employees there) and a few more scattered around.  I managed to marshall these few people into building something we were able to sell to a large retailer, to manage their shipping process.  We didn’t have health insurance yet, but paychecks were regular and covered COBRA payments.

While Jeff and Bill sought funding, I used the few resources we had to build what we could, and put together increasingly ambitious plans based on our ability to secure funding, and our ability to sell what we already had to the burgeoning Internet retail market.

To put this in context, this is an era where a company could boost their stock price by putting an “e-” or a “.com” in their name, where startups would spend millions on waterfalls in their lobbies, Webvan and Pets.com were in full, inexplicable swing, along with Kozmo and Flooz demonstrating that startup capital and a dot-com model were the fast track to corporate success.

On the other hand, we were a down-to-Earth, hard working company, were careful about our spending, and didn’t yet have funding.  What we did have was part of a product, a handful of competent employees, and an office that after a while, nobody bothered going to.  After all, the servers weren’t there, the employees were remote, and venture capitalists were elsewhere — as nice as Regus was, it was clearly temporary, shared office space, not the place you’d bring venture capitalists to impress them with your waterfall, and god knows you wouldn’t want Willy Loman around.

The CEO called and said we’d leased permanent space — it was time to move.