Billed as one of Canada’s hottest 30-something entrepreneurs leading one of its most promising companies, Kashif ‘Kash’ Hassan bootstrapped a mobile integration firm into Wysdom, a wireless ASP riding the frothy whitecaps of the Dot Com tsunami.

After two multi-million dollar funding rounds, Wysdom landed a stunning $50 million USD ($70 million CDN) in February of 2000. The NASDAQ collapsed two weeks later. Starved for business, Wysdom ‘restructured’, Kash departed in 2004 and by 2006 the company was dead.

Red Canary caught up with Kash to talk about Wysdom, the crash, and his advice for today’s startups.

KASH ON WISDOM
What was the funding environment like in 2000?
If you look back at the first quarter of 2000, the Nasdaq was at an all-time high. Wireless was big, valuations were going through the roof—we did it at a time when the market was the hottest it’s ever been. I don’t think anyone expected the market to crash literally two weeks after we closed the deal.

Did you have to shop around?
We just happened to time it at a point where everyone was looking for deals. It took us about 30 days to get a deal done, there was a lot of interest at the time.

Was it the largest deal in Canada at the time?
If it wasn’t the largest it was one of the largest.

What about your products. Was the market ready for Wysdom’s application model and its map-OS framework?
We were early. I look back now and we were probably two or three years early.

If you look at map-OS, everybody’s talking about the same concept today, the concept of service delivery platforms, making it easy for developers to build applications…everything that we talked about in the early days people are doing now.

“I don’t think anyone expected the market to crash literally two weeks after we closed the deal.”

I remember when everyone was talking about 3G (cellular) networks and how it was going to revolutionize everything…yet we still don’t have 3G networks in Canada.
Yeah but in Europe it’s happening. A lot of the stuff Wysdom talked about doing…people came in later and started doing some of that stuff. When we were going people were taking opportunies and everyone was talking about growth, but once the market collapsed it was all about restructuring. The spend wasn’t there. The [telco] models hadn’t evolved.

So was there a tipping point? A day where you said to yourself “this company isn’t going to go the direction I thought it would?”
Not really, hindsight is always 20-20. I was looking at some old pictures of the events – just looking at the names, the faces, the times.

Looking back, I think I would have switched direction on certain things, but that was the direction we went in. For all the challenges we had I think we had a good team. (laughs) Gotta get the timing better next time!

ON CANADIAN STARTUPS
Do startups have something to learn from Wysdom?
I meet a lot of startups and everyone’s got all these great ideas, but I think people get in to startups and then realize that there’s actually a lot of work that goes into building companies.

It’s easy to build some basic code, but as you build a company you have to make sure you have everyone going down a straight path, making sure that you’re funded, that you’ve got real revenue – there’s a lot of pieces that have to come together for you to be successful.

What do founders need to do?
You got to start thinking about financing, you’ve got to start thinking about human resources, how to hire, how to fire, and so on.

“People get in to startups and then realize there’s a lot work.”

Was there one specific executive position that you can say you relied on the most?
The funny thing is…I don’t think there was one person specifically…Ian Collins [Wydom’s co-founder] was was my partner and we relied on each other for a lot, but the reality is it’s not one person.

How would you say your role in the company changed as you went from 5 employees to 175 employees?
It’s having to give up control, you let people do their jobs. At 5, you’re basically doing everything, at 175 you just can’t deal with everything.

That’s why you have to have people that you can trust to make decisions, to do the right thing for the business.

We went through two acquisitions.

What was that like?
You have to have the infrastructure to run and maintain everything….it’s details.

When you’re at 5 people you’re managing around a few pods, when you get to 50-100 people you’re managing a facility…when you get to 175 people after acquisitions you’re managing people in different facilities, in different time zones, in different countries.

You need more and more infrastructure to run your business.

“At 5, you’re basically doing everything, at 175 you just can’t deal with everything.”

What’s changed in Canada’s startup environment? How are Canadian startups doing things differently?
There are still a lot of Canadian startups, which is a good sign. Canadian entrepreneurs are waiting a lot longer before they go get money from a VC or wherever.

So It may get hot again, but probably nothing like what it was.

Never say never.

Is there a problem with funding?
I think startups are getting back to being startups again – without having to spend lots of money. They’re being more intuitive in terms of how they get work done. I think the collapse of the markets pushed a lot of people to start looking for profitability earlier in their business There’s also not as many angel investors as there used to be, a lot of them lost money during the bust.

“I think startups are getting back to being startups again…”

So development costs are lower?
I think that has changed but at the end of the day a company is not just software, it’s putting the software with the sales with the marketing and that still has an inherent cost to it.

Do Canadian companies not do a good job at those aspects?
I don’t think it’s that Canadian startups don’t do enough, it’s just that they haven’t gone through it enough, what you’re seeing is, second time around, people are able to do things quicker.

At one point Wysdom had 175 employees. What would you say to a startup with a good revenue stream that’s about to hit a growth phase?
It’s all the cliches, hire the best, hire the brightest, but at the end of the day you really have to manage your growth.

“What you’re seeing is, second time around, people are able to do things quicker.”

How do you do that?
I call it a soaking-in period. When you bring people in they bring their culture [with them] – if you bring in too many people too fast you lose the culture that you’ve got.

Make sure that the revenue isn’t just a spike…you’ll hire a lot of people and all of the sudden you’ll realize ‘hey that was just a spike in our activity and we probably shouldn’t have hired all these people”.

I would look at bringing in contractors, have the flexibility of full-time and part-time. Understand what you want long-term and what you want short-term.

And if a startup wanted advice with this kind of situation, who would they go to?
If they’ve got a resource like Red Canary it’s not a bad place to start. (laughs)

There are a lot of good VCs that add money but they also provide value from a networking and contact perspective.

ON HIS NEW COMPANY
Tell me about your new venture, ooober.
Being in the wireless space you realize how difficult it is to do it, so many different devices, so many different networks, no real standards. So our model is: let’s make it easy for anyone who has content to be able to buy and sell in an online marketplace.

A mobile content marketplace?
Kinda like what Ebay did for buyers and sellers, anyone who had stuff could sell it to anybody who wanted stuff. We’re doing the same thing in the mobile world, allowing people who have content to sell to people who want content.

We take care of the billing, the operators and the different devices.

What are you doing differently this time?
We were underground for about a year or so…just going through, trying to figure out the business model, building the technology, making sure things worked.

At the end of the day you have to build good businesses,we didn’t want to get out too far ahead of ourselves [with ooober].It’s like every business, you’ve got to keep your head down, keep focused.

IN RETROSPECT
What are you proudest of at WYSDOM?
We’ve got 100 entrepreneurs that were at Wysdom and are now out on their own. It’s kind of like an alma mater. These people will help create more companies in Canada, it will be good for Canada in the long run.

Personally, how would characterize the whole Wysdom experience?
I went through everything. Huge highs and huge lows, but at the end of the day you’ve to keep moving forward, you can’t stick your head in the sand.

Would you do it again?
Yeah, absolutely.