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When Adam McIsaac started his company, Robin Media Inc., in 2016, he thought it was a sure bet. He planned to help music fans beat scalpers and ticket bots by working directly with musicians and concert promoters, reserving tickets before concerts went on sale and then selling them to fans for a modest additional fee.

Jocelyn Molyneux was just as bullish when she founded her company, Wastenot Farms. Her customers are offices and other workplaces in Toronto – she collects their organic waste and brings it to her composting facility north of the city, helping companies ensure they are being environmentally friendly (private haulers often send the waste to landfills).

Robin and Wastenot could hardly be more different in terms of their target markets. But both experienced similar misfires, pivots and lessons learned before they began to thrive.

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That’s no coincidence. Many entrepreneurial mistakes come down to a handful of classic errors. First-time entrepreneurs can learn a lot simply by looking at what others did wrong – and how, like Mr. McIsaac and Ms. Molyneux, they recovered.

Over-relying on intuition

Mr. McIsaac, a passionate music fan who had previously worked in the ticketing business, identified what he thought was a pain point that consumers would pay to resolve: combating scalpers and online ticket bots that scooped up tickets for shows the moment they went on sale.

Robin-Adam McIsaac.jpg Adam McIsaac, CEO of Robin HANDOUT

Mr. McIsaac’s idea was to offer music fans a chance to get those tickets before they went on sale. But his intuition led him astray: “Even though people wanted what we offered, they weren’t always willing to pay for it.”

Likewise, Ms. Molyneux’s background in environmental work gave her an encouraging early network of potential customers. But once she exhausted those, she hit an early plateau. “If we went wrong somewhere it was using my own biases to assume that this would be a hit right off the bat.”

Many first-time entrepreneurs avoid the hard work of basic market research, says Kristjan Sigurdson, associate director at the Creative Destruction Lab at the University of Toronto. When trying to convince investors of their market-readiness, they rely too much on their own experience or the testimony of friends and acquaintances. “If you interview a hundred people, but they’re all people at your grandma’s retirement home, they’re not going to seriously criticize you,” he says.

Entrepreneurs should instead devise a research methodology designed to invoke criticism. Canvass strangers in a public place, ask pointed questions about drawbacks, and don’t tell people it’s your product, instead presenting it hypothetically.

“It can be hard on your soul when someone says, ‘This is garbage, I would never buy it,'” says Mr. Sigurdson. “But it will save a lot of pain in the long run to ask why.”

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Ignoring your competitors

Instead, consult them. “Many will sit down and talk to you,” says Scott Bowman, a senior director with Futurpreneur Canada, a national non-profit that provides mentoring and financing to entrepreneurs. “People think everything is cutthroat. Sometimes that may be, but often not. So listen to what advice they give you and weigh it against your own plan.”

This is especially valuable in industries in which a rising tide is lifting all boats. Mr. Bowman points to one of his clients, a brewery in an area in which two dozen other brewers are within a 30-minute drive. They all share customers, insight and even equipment.

“Their competition isn’t each other,” he says. “It’s the big multinational beer companies.”

In Ms. Molyneux’s case, the competition was obvious. Recycling and organics are already being picked up from office buildings at no cost, though that waste is often sent to landfill because it’s cheaper for haulers to take it there. Ms. Molyneux would guarantee the waste be properly handled, but her early failure to reach sympathetic customers – workplaces who wanted to make sure their compost waste was actually composted – points to a related blunder:

Neglecting sales and marketing

It was easy to persuade environmental groups such as the David Suzuki Foundation to be customers, and that hid the sales challenge that would come after the low-hanging fruit was picked.

Jocelyn Molyneux, founder of Wastenot Farms

After she hit an early plateau, she went back to her small customer base to look for commonalities. She discovered that in many offices, younger employees were the driving force behind efforts to go green. So she began identifying youthful companies, especially tech outfits with a large millennial work force.

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That changed her entire sales strategy. Instead of looking at a whole workplace as a customer, she formed one-on-one relationships with employees within workplaces. A more fully developed sales strategy may have unearthed that nugget sooner.

Overlooking the rules

Too many businesses run up against unexpected obstacles thanks to some overlooked bylaw or regulation, says Mr. Bowman. He cites the example of a first-time restaurateur in Toronto who took over an existing restaurant space. He’d assumed that the exhaust fans in his kitchen were up to code, but when the space was inspected, the owner was told that he’d need to replace them – at a cost of $80,000.

“He was nearly in tears,” says Mr. Bowman. “It delayed his opening and pushed his budget very thin. It had a happy ending, but it was close.”

When it comes to highly regulated fields, says Mr. Bowman, make sure you understand the fine print, and never take “that’s probably fine” as an answer.

Not pivoting fast enough

This is how Mr. McIsaac started to turn things around with Robin Media. Last summer, he took a hard look at the company’s numbers and had what he calls a “come-to-Jesus moment of realizing that the product wasn’t providing much value.”

That inspired a painful deep dive into the business – and a potential salvation. “We spent a month being honest about the data and speaking to loads of customers,” says Mr. McIsaac, “and realized that those using it most were using it for corporate purposes. Buying tickets to gift to a client, or taking staff out for events.”

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So they began changing Robin from a business-to-consumer company to a business-to-business (B2B) company. It wasn’t Mr. McIsaac’s original vision, but it was close.

“Killing your babies really applies in the startup world,” he says. “The earlier you can move on, the better for you, your employees and your investors.”

Growing too fast

Mr. McIsaac made one mistake in the shift, however. He held on to some employees longer than he should have, and that complicated the pivot.

Great entrepreneurs can integrate new information and almost intuitively change strategies, says Jon Worren, senior director of venture and corporate programs at the business incubator MaRS Discovery District. But that’s harder if you have 20 employees than if you have two.

"A lot of companies scale [grow] before they’ve figured out what they’re really supposed to be, and that means they’ll hire the wrong people, scale up the wrong product, and so on.”

Today, Mr. McIsaac says he wishes he’d let those employees go sooner, both for the good of the company and for the employees.

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“It’s hard emotionally, but it was inevitable, so drawing it out wasn’t helping anyone,” he says. “When your business isn’t working, you’re not providing an environment for people to do their best work.”

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