20/20 Hindsight – Being Pioneers in a New Space
This is my site Written by Alora on April 24, 2009 – 12:07 pm

PioneersAsk anyone who got into an internet-based business prior to 2000, and you’ll hear nostalgic “good old days” stories, the way my grandparents talk about ‘when Kennedy was President.’ It’s hysterical to hear, and it saddens me endlessly to think about how long ago that was, but it really was an exciting time — and not just for the massages and catered lunches (which we had, too).

What was exciting was doing something new. Being a small group of people, pushing a boulder up a hill together was an amazing experience on so many levels.


On a purely personal level, it provided both opportunity and comradery that I absolutely soaked up like a sponge. There is no bond between co-workers like the bonds built while firefighting in the middle of the night for days on end. People are tired, punch drunk, but our brains were flying like trapeze artists trying to find solutions. And the best part? Every single time we eventually figured it out.

That built huge faith and trust in and among the team, because you quickly learned who was good at what, and who you needed to pull into a room when something was blowing up. I learned that technical trouble-shooting was an art form, and the fine-tuned dance we could do as a team when it came to examining the performance of complex systems would make the Bolshoi envious. To this day I find a kind of agonizing beauty in pulling together a talented team of people to trouble shoot a truly baffling problem; and to this day, I’ve never worked with full teams of people who were as gifted at it as the people I worked with in my early career.

And some of the most important people in my life to this day, were the people from that time and place in my life. I wouldn’t trade it — or them — for anything.


When you are trying to build something new that not everyone understands or cares about (or understands why they should care about), you have to learn to be very quick on your feet. You have to be able to discern what is truly important to them, and then draw them a map of why what you are offering will lead them to where they want to go. Sometimes it’s an obvious leap; other times it’s total bullshit. But either way, it’s an intellectual challenge that is invaluable to master, because you have to do it quickly, while you’re ‘on stage’ and you have to be sincere enough to be convincing.

It sounds like I’m saying that I learned to be a salesperson, doesn’t it? In truth, I did. To be sure, I don’t enjoy “sales” in general and I’d never want to make my career at it, but all business is selling. And if you want to be good at business, you have to learn this — the earlier the better. Whether you are selling yourself and your skills to a potential employer, or you are selling your product to a potential customer, anyone who can’t figure out what someone wants and how to give it to them won’t make it very far in business.

The sooner you learn this, the better off you’ll be.


When I first got online way back in 1993, the internet was still a playground. It had not yet become ‘the new frontier’ of business. But I loved it, and since the web was beginning to emerge as a viable business environment, I knew I wanted to find a way to do that professionally. I just didn’t know how or what exactly that would mean.

Being in ecommerce from 2000-2005 was a great time. And targeting the small- to mid-sized cataloger and retailer (which was our demographic) was what kept us alive when the bubble burst. It also proved to be highly valuable for other reasons.

While other ecommerce software providers were busy trying to sell into the top end of the market — the Fortune 1000, who had millions of dollars to spend on a site — we were aiming at a higher volume of smaller clients. Of course, this was one of the reasons that we couldn’t continue to be a services company — we had to have a product in order for our business to scale this way. But it also meant that we had a much bigger pool of potential customers. All we had to do was to streamline our own processes to be able to take advantage of some economies of scale.

What is still one of my favorite parts of this whole experience, though, is when I remember back to conversations that we used to have with C-level executives (usually either CEOs or CIOs) about setting up an ecommerce site. Many of them were still unconvinced that it was actually necessary. The old school, brick-and mortar retailers and catalogers were often not ready or able to see that their world was about to be completely transformed, and that the internet was going to be the heart of the future of their business.

Often times there was an internal evangelist (and in family-run businesses, it was quite often the founder/owners’ twentysomething kid who was working in the family business and trying to push things forward) who convinced the CEO to at least listen to the pitch. But even after they heard it, they were still frequently not convinced that the internet wasn’t just a fad that would go away in a couple of years, and that any investment made in the meantime would ultimately be a waste.

Looking back on it, these conversations always make me smile, because they are classic examples of adoption resistance that all new technology breeds. At the time they were highly frustrating and (from my standpoint) ridiculously short-sighted. But now I think about them and chuckle.

To be sure, each one of the reluctant CEOs did eventually have to cave to their internal evangelist and outside market expectations of their customers who truly wanted them to make their products available online — whether they chose our product or not. And, in the end, they did all come to recognize that, over time, ecommerce was essential to the health of their business. But in some case it took a while.

That experience was illuminating for me, though, and it is probably the single biggest reason that I have very little patience for the whining currently going on in the automotive and newspaper industries. To paraphrase Ricardo Semler: if you bury your head in the sand, not only do you miss vital opportunities, but you also leave your ass in the air as one hell of a big target. Those who’ve spent the most time and effort burying their heads in the sand end up screaming the loudest when they get shot in the behind. And truthfully, I have no sympathy.

Any thoughts on other value to being on ‘the bleeding edge’ of a new space?