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The six toughest small business Challenges of 2014
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From left, Ryan Dingman, Nima Pazouki and Reza Saljoughian are partners in a virtual dry cleaning business called Clean It Online. (Galit Rodan For The Globe and Mail)

Web-based dry cleaner has an analog dilemma

We bank and shop with the click of a few keys, yet dry cleaning remains one of the few tasks that has resisted the switch to a primarily online convenience. The founders of Clean It Online are hoping to end this analog anachronism. Their cloud-based service operates entirely on the Internet.

But how to deliver the clothes – that’s what needs ironing out. Read the story here.

Mike Pinkesz, co-founder of Breakup Gems. (Christinne Muschi for The Globe and Mail)

Headed for splitsville? Jeweller has a ring for you

The founders of Break Up Gems are not interested in happily married couples, but rather divorced women who now have a ringless finger. They hope that once people remove their wedding rings, they’ll want to buy something new to put on.

But the company has had trouble getting the concept across to potential customers. Read the story here.

Macadamian Technologies was relying on clients’ e-mail addresses for marketing and outreach. Canada’s anti-spam law has curtailed that, says Brooks Riendeau, senior manager of market development. (Dave Chan for The Globe and Mail)

Anti-spam law is a pain in the marketing plan

For years, Macadamian Technologies, a software company, used e-mail addresses to cultivate relationships with customers and woo prospective ones as well. But then one of Canada’s most comprehensive and strict privacy bills took effect, making things more difficult.

How can Macadamian find other ways to reach out? Read the story here.

Danny Crossman, co-founder and CEO of Impakt Protective Inc., has developed wireless helmet sensors under the brand Shockbox. When attached to a sports helmet, the sensor sends an alert – via wireless transmission to a tablet or smartphone – telling a coach or parent when a player has suffered a hit to the head, and how hard. (Blair Gable For The Globe and Mail)

Concussion sensor gets a cool reception from sports helmet firms

You’d think a screening tool designed to make contact sports safer for children would be a slam dunk.

Not so, says a founder of Impakt Protective Inc., which developed smart wireless helmet sensors. When attached to a helmet, the sensor sends an alert – via wireless transmission – telling a coach or parent when a player has suffered a hit.

But instead of being embraced by helmet manufacturers, the Ottawa company has encountered roadblocks. Read the story here.

Justin Davies’ ATM machines can be found in such businesses as bars and convenience stores, where the owners encourage or require cash-only transactions. (Kevin Van Paassen For The Globe and Mail)

ATMs driven to the fringes as technology advances

Is cash still king? For 10 years, Justin Davies has been installing and maintaining automated teller machines in Toronto-area bars, convenience stores and ice cream shops. Despite the declining need for cash among consumers, Mr. Davies remains optimistic.

“Cash is more resilient than most people think,” he says. How can he adapt to these changes? Read the story here.

Sean Neville is the owner of Healthwick Canada, an online retailer that provides home delivery of adult diapers in discreet, unlabelled boxes. (J.P. Moczulski For The Globe and Mail)

An e-tailer’s dilemma: Marketing the unmentionable

Businesses that deliver what they promise can usually rely on word-of-mouth marketing from satisfied customers. But when you’re selling diapers for grown-ups, even the happiest are likely to stay mum.

How can Healthwick, which delivers diapers to customers in plain packages, reach out to people who don’t go on the Internet much and would rather not discuss their needs? Read the story here.