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Entrepreneur Kelly Hoey on how to network (and negotiate) like a pro

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Entrepreneur Kelly Hoey on how to network (and negotiate) like a pro

Kelly Hoey — investor, entrepreneur and networking guru — is a household name right now, but that hasn’t always been the case.

Before she became a successful investor and author behind “Build Dream Your Own Network” she worked as a lawyer. While she never had a “burning desire” to practice law she enjoyed it. Her ambition to continue working up the corporate ladder all changed after she met Janet Hanson — founder of 85 Broads, a global business network for women. The “visionary leader” inspired her to trade law for entrepreneurship and launch a brand new career.

Below the acclaimed business consultant dishes on how she’s managed to transform her career and how others can throughout their careers.

[This interview has been edited for clarity]

You’ve successfully reinvented your career over the years multiple times. How can others emulate your success?

 
Stay curious and stay connected to your networks. I’m a former corporate lawyer who has networked her career into becoming a published author. A professional milestone I never imagined adding to my resume. From my initial jobs as an attorney to my numerous career-changes (law firm management, president of a global network for women, consultant, director and co-founder of a startup accelerator) my career is only explained by my ability to network and build relationships.

You mention in your book that part of your professional growth and achievements is down to “marketing” and self-promotion.  Why is this important?

 
Your career is your best investment. Be prepared to put the time and effort into that investment. Venture capitalist Jessica Peltz-Zatulove outlines how she “cold-emailed” her way into the Madison Avenue advertising industry in chapter three [of my book]. And, one of my favourite case studies is Joe Styler a manager in the aftermarket department at GoDaddy. He shares in the book how he networked from an entry-level position at the company to a recognized industry-expert in a coveted role.

Another career networking lesson: Don’t overlook the possibility you can pivot and advance your career within the same company!

What advice would you share with  entrepreneurs who want to take their careers to the next level?

 
No one ever goes it alone. Our careers or projects or initiatives are propelled forward with the help of other people. Find mentors around you. Having mentors as well as being a good mentor is critical for learning how to master a new skill or navigate the dynamics of the business community.

Mentoring comes in a variety of forms – it can be one piece of advice, a blog post or a podcast. It does not have to be a 1:1 coffee date. It does not have to be a lifelong commitment. In reality, just as you don’t have time, that dream mentor may not have the time either for regular 1:1 coffee dates with you. Most people do have the time to answer a well thought-through email. Mentors are there to guide you through thorny work or professional challenges. If someone can help you sort out a work challenge by answering a question (once), well, why isn’t that considered mentoring?

STEM has received a lot criticism for its lack of diversity. What can insiders do to help change those statistics?

 
Again, be a mentor. Hire interns. Volunteer at hackathons at local libraries or community centers. Make it a career priority to expand your network and to share your interest in STEM with a more have a diverse group of people. [That means] industry, geography, tenure, experience, gender, education and whatever else you can think of.

A broad, diverse network is going to allow you to provide others with more opportunities (and you’ll get more ideas and feedback too). Keep in mind: the power of networking is not just the person you’ve just mentored or tutored or trained. [Networking] is all the people that person is connected to, too.

What books, tools or technologies would you recommend for people in the early stages of networking?

 
I always recommend Katharine Graham’s “Personal History”. Katharine led her family’s newspaper through Watergate.

Whether you want to be a fiction writer or not you should also read Stephen King’s “On Writing”. It is as much about how to dedicate yourself to your chosen craft as it is on understanding how you come up with new ideas and communicate them.

Watch Ray Anderson’s Ted Talk “The Business Logic Of Sustainability”. There’s also Phil Hansen’s novel called “Embrace The Shake,” too. Also, join the CreativeMornings breakfast lecture series community.

To hear more of Kelly Hoey’s advice, personal guidance or to ask her questions in person attend this upcoming event at the DMZ for free.

How to lure and hire top talent before your competitors do

Canada’s tech scene is on the rise.

Toronto, its largest city, is home to a booming artificial intelligence ecosystem. It also boasts an enviable research center that includes the country’s first technology supercluster and an entrepreneurial drive that’s second only to the U.S.

It also doesn’t hurt that Canada’s Global Strategy program helps fast track immigration for talented workers. The new law makes it one of the most liberal programs in the world. In as little as two weeks workers can get visas and working permits — making the talent search that much easier.

But, despite all this good news Canadian startups still have a difficult time finding tech leaders to help them grow. While the country has the right people on hand onboarding them isn’t always easy. That’s why recruitment strategies are playing a much bigger role than they ever have before.

Engaging with talent before they apply

For Dave Savory — co-founder of a startup called Riipen that connects young jobseekers with companies — finding the best talent quicker and more efficiently means shaking up how HR engages with talent. The old-school recruitment method that requires applicants to fill out page-by-page forms online just won’t do anymore. Engaging with emerging talent sooner through games, brain teasers or social media yields better results.

“Having a new entry point based on merit and skills instead of how many buzzwords you can fit in your cover letter is what you should look for. People are now trained on how to get passed automatic resume filters that companies set up,” he explains. “It ends up making more work for people at a company because they spend time interviewing people who may not be a great fit or miss out on really great people.”

Savory knows better than most about what companies look for in employees. Riipen, founded in 2013, works with 140 post-secondary schools and 7000 companies in North America to help students find work. His clients vary and include tech giants, like Microsoft, and food businesses, such as restaurant chain Joey Restaurants.

“It’s all about how good companies authentically engage with emerging talent,” he adds. “Companies know [young people] are an important demographic as older workers retire, so they need to find new ways to get their attention before their competitors do.”

Check out the weirdest interview questions Fortune 500 companies asked prospective employees last year, courtesy of GlassDoor.

Businesses suffer without HR innovation

Robert Sher — who works in San Francisco, a city with an unemployment rate of 3.5 per cent — put it best. “Flawed hiring processes” play a role in hiring and retaining the best people, which impacts a business’s bottom line.

“Companies that can’t find creative ways to find the employees they need can’t grow,” he explained. “Business leaders who can win the talent war (and it is a war) will be able to say yes to new business opportunities while their talent-strapped competition will have to walk away.”

Bryan Rusche, Soapbox’s marketing director, believes the hiring landscape has changed in recent years. While his company doesn’t directly work on recruitment processes, their platform allows employees to share ideas and feedback that can impact how companies attract new talent.

“The best strategy for attracting talent is having a reputation for being an amazing place to work,” he says. “The slickest recruitment strategy in the world isn’t going to work for you if your employees don’t back up your claims that you have something special,” he explains.

As times change, businesses will be forced to change their hiring policies as well.  They’ll increasingly need to rely on better ways (and platforms) to connect with talent if they want to succeed. “This will be the new normal in the next three to five years” says Savory. “Engaging talent through skill-based assessment or challenges will be the new starting point of the recruiting process.”

The kids are alright: How these entrepreneurs plan to beat diabetes

It’s 9:45 p.m. on a run of the mill Tuesday and Shaan Hooey is tired.

It’s been a long day for the Canadian entrepreneur who spent most of it talking to investors and answering media calls but you wouldn’t know it by how excited he is when discussing his medical startup, GlucaMed. The company has created its first prototype for an injectable pen that contains glucagon, a medication used to treat low-blood sugar in Type 1 diabetics.

From his home, Hooey describes over the phone how he and his partner, Sameer Jessa, managed to get the business off the ground in great detail. But, perhaps, the most compelling part of his story is that the co-founders behind this game-changing piece of technology are only 15 years old.

“Innovation is my motivation,” he says, with a laugh. “I was inspired to create the [Glucopen] because my sister has diabetes and I saw the pains she had to go through. I saw when she would have to sit on the sidelines [because of] low blood sugar and I thought there had to be a better way.”

Jessa agrees.“I’ve actually met with Shaan’s sister and I’ve seen how she’s struggled with her diabetes,” he says. “No diabetics should have to live with their life in danger.”

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Although current products on the market today work just fine, Hooey explains, they’re counterintuitive. The first time he practiced using one of the injection needles — his sister often carries with her for safety — it took him 10 minutes before he could get it to work. “That’s too long in an emergency situation,” he says.

But why did it take so long? Before contemporary glucagon injections are ready to be used, individuals need to mix together two compounds (a powder and a liquid) stored separately by hand. Most diabetes kits intentionally store the compounds separately because when mixed it has a limited shelf life and costs more than approximately $200 per kit making it too expensive to waste. However, this setup can also prove tricky for first-time users (or even experienced diabetics) under pressure.

GlucaMed changes that by making the mixing of the two compounds as easy as pushing a button — think of it like an Epipen for diabetes. In order to inject the device all a user has to do is pull off the safety cap and push a button to deliver the substance. No hard work required. It’s a great idea that has even garnered interest from some of the industry’s biggest names, like California-based entrepreneur Navid Nathoo, founder of Airpost, and Accenture consultant Alexis Tremblay.

Their idea behind the device is so popular, in fact, that the teen entrepreneurs now have an investor and impressive board of directors by their side. Their impressive list of cheerleaders also includes the duo’s supporters from Sandbox, the outreach arm for the DMZ an outreach organization based at Toronto Metropolitan University and The Knowledge Society, a student-focused tech incubator based in Toronto.  

For now, Jessa and Hooey are focused on clinical trials and bringing their product to market. Since they’re underage, working out trials is an unusual hardship as most labs won’t even let minors enter their facility. But, they’re not letting that interfere with their plans.  

“We’re going to keep working at this,” explains Hooey. “We think this could change the world.”


24 hours with real estate startup Casalova

The real estate startup is located in downtown, Toronto — one of Canada’s most competitive real estate markets — which means employees have to always be on their toes since local listings can change in the blink of an eye.

Unlike some of its competitors, Casalova is a one-stop shop that brings together prospective renters, landlords and agents all in one place. Users who sign up get access to new homes and a certified agent, while landlords have their properties listed and also get a $100,000 insurance package so they can rest easy knowing that if a tenant damages their homes they won’t go into debt to fix it.

Here’s an exclusive behind-the-scenes look at the inner workings of Casalova’s team and their founder.

The agent: Jennifer Meade (9 a.m. to 12 p.m.)

jennifer_meade

Jennifer Meade, one of the company’s newest agents, knows all too well how volatile Toronto’s real estate market is these days. She’s seen up-close-and-personal the city’s property market jump more than 20 per cent in the last year, and more importantly, the impact it’s had on prospective renters and buyers.

“Everything moves so fast now,” she explains. “If you want something in this market you have to be ready to move quickly because property can go just like that,” she says while snapping her fingers for added effect.

For Meade, most days involve checking her email to see which new clients she’s been matched with through Casalova or connecting with new renters through her own personal network. Today her client, a nurse moving from Barrie to Toronto, is looking for a condo to call home in the downtown core, which Meade confesses “can be tricky” since the prospective renter’s 14-hour job makes it difficult to view properties during normal hours.

Today her day starts at 7 a.m. when she scours local listings for new condos. When she finds one that matches her client’s needs (in this case parking and access to shopping and entertainment) she calls the property manager to book an appointment and waits for her client to make the long drive downtown.

Two hours later she shows the nurse around a lovely condo near the city’s waterfront while rattling of its impressive amenities — inclusive gym, pool and hot tub, to name a few. It’s a one bedroom, 778 square feet, home that overlooks Lake Ontario. While Meade thinks she may have found her client the perfect home although she isn’t so sure and wants to look at a few other places before making a final decision.

Keen to see her client view as many places as possible she hails a taxi that will shuttle both of them to their next destination. She also informs the condo owner over the phone that her client is interested in the property but needs a little more time to make a decision. “It’s important to keep every door open,” she says with a smile while juggling two phones.

Two hours and three condo viewings later (a cancelled showing due to a lost lockbox means the day ends early) just reinforces how much her client loved the first apartment she viewed earlier in the day. Meade later makes an official offer that day with help from Casalova’s customer service team and then make plans to meet tomorrow to follow-up on signing details.

“It always feels good when you find the perfect home for someone,” Meade explains.

The front-line staff: (1 p.m. to 3 p.m.)

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Naveed Marzook, Casalova’s vice-president of customer success, loves his job. It’s easy to see that he and his team shoulder most of the face-to-face customer and agent work the company deals with on a daily basis. Any questions about properties, or payment requests go through his team.

The customer service team also helps customers navigate the website if necessary and add new homes to the company’s growing list of real estate options almost hourly.

For all intents and purposes, Marzook and his team are like the swiss army knife of the company, although he refers to his team as the startup’s “helpers”. They go “above and beyond” what they’re expected to do all the time, he explains. “Everyone pitches in and we appreciate it.”

Marzook and his team believe that the company’s success boils down to the fact the team actually like working together. In an attempt to prove his point, he holds up a golden owl, fondly named Hooter, which is given to the employee who happens to “pitch in the most.”

Today it might be him, and the next day it could be Jess Shulist — one of his colleagues whose computer is decorated with Rihanna stickers and works with agents to get client documents ready.

“It’s a fun place to work,” Shulist says while looking fondly at Hooter. “I think it’s cool how we never forget to recognize how hard each other is working.”

The co-founder: Ray Jaff (3 p.m. to 8 p.m.)

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Ray Jaff wakes up at 6 a.m. everyday to workout. He works through company problems while running on the treadmill and brainstorms new solutions while lifting weights. “It’s what gets me through the day,” he explains.

The entrepreneur is dressed in a fitted oxford shirt and pleated pants, but says he would be just as comfortable in jeans and a t-shirt.

This afternoon he’s focused mostly on checking in with team members, going over the website’s latest updates and the company’s plans to move to a new office on the westside.

At a meeting with the team’s engineers, Jaff and the developers hunker down at their desk to come up with solutions and a tentative timeline for new product updates. Forty-five minutes later they’re done and the founder is already on his way to his next meeting. His phone blinks throughout the afternoon proving just how in-demand he is these days, especially now that the company has launched its services in Vancouver.

It’s a real coup for the startup, he says. “We’ve been working towards this for a while.” When asked how he manages to avoid burnout, Jaff merely laughs and shrugs. “It’s a team effort, we’re all working on this together and we aim to only hire A-players who are dedicated to the Casalova mission. It’s makes everyone’s life a lot easier.”

Later on the company’s real estate agents, front-line staff and Jaff convene to celebrate their quarterly wins at a complimentary lunch while munching on sushi, chips, cupcakes and champagne. Despite its seemingly small team, the event is an important way to show employees how much their hard work is appreciated.

“Casalova is like a family. We value everyone and just because the agents aren’t in the office with us doesn’t mean they shouldn’t be here with us to celebrate.”

The award categories include ‘Rookie of the month’, ‘hardest hustler,’ and ‘MVP of the month.’ After the awards are given out, Jaff motions for people to move to the front of the room for photos with the honourees.

Once the meeting is over, it’s back to meetups with staff, responding to more emails and later one-on-ones about Vancouver. It’s almost 8 p.m. by the time his day is finished.

As he readies his things to leave for the night the entrepreneur’s eyes are still glued to his smartphone.

Parent trap: Here’s how entrepreneurs with kids make it work

Being an entrepreneur is hard, but being a parent (one of the toughest jobs in the world) and running your own business at the same time is even harder.

While most people would assume that combining children and a career in tech could end up being a hindrance, it’s actually a boost to an entrepreneur’s bottom line if they can manage to pull it off.

Children and careers can make the perfect combination

 

The startup life usually comes with late nights, negligible pay and unpredictable schedules. That added stress can easily become overwhelming. For some founders being a parent is a boon because it forces them to be smarter, faster and better at prioritizing what really matters in life and work.

“The best part is that you get to cut the crap out of your life — no watching YouTube or on Reddit when I’m at work,” explains Matthew Karabela, co-founder of Fetchit. The DMZ-based startup connects businesses and Canadians with pick-up drivers, truckers and other hauling equipment operators from across the country.

“Having kids teaches you how to give [work] your all when you have free time and really focus.”

Karabela’s company – which he describes as an “Uber for pickups and deliveries” – is especially unique in the startup ecosystem because two out of three of its founders are parents. “Not many companies have one founder with kids and we have two but it hasn’t stopped us from being successful.”

Since launching last year, Fetchit has seen its membership increase to 1600 users, partnered with over 20 businesses in Toronto, and now has approximately 220 drivers using its service. Despite its early success, the father of two is quick to admit that his company gains didn’t come easy.

Having an eight month old and toddler at home means he’s missed a few bed night stories throughout the year, which has also coincidentally made him a master at multitasking.

Changing nappies with one hand while holding town hall meetings or working late into the night to accommodate sick kids comes with the territory, he says. “It’s hard work, that’s true, but I wouldn’t change anything” he explains. “When you think about it like a business, raising kids gives you a better return in the long run. My family makes me a better person.”

Benefits of being a parent: Advice from the other side

 

Sharn Kandola, cofounder of real estate startup Feed Duck and mother of two, believes the difficulties that go along with raising kids sometimes overshadows how beneficial they can be for a founder’s business.

In the startup world, where networking is a crucial part of the biz, being a parent can open up social and professional circles in a way that cocktail mixers and after-hour meet-and-greets can’t. “You meet so many people just by going to parent events or school activities,” she explains.

Parenthood also helps entrepreneurs stand out among the competition and be a better boss.

“Being a parent gives you a better perspective, because you know what it’s like to lead and guide someone else,”

Kandola later adds: “If you’re an entrepreneur and a parent you can help support other entrepreneurs and your business as a whole because you spend so much of your time doing it at home.”

Secrets to success

 

For Karabela, balancing both worlds and the responsibilities that go along with it requires hard work. Unlike at regular nine-to-five jobs, sick leave is poor and maternity leave almost non-existent. Understanding your personal limitations, leaning on friends and making exceptions in the short-term to help your business get ahead should be a given.

Kandola agrees. The entrepreneur wakes up early so she can focus on her business and get a head start on the day. A 5 a.m. wake up call during the work week might be daunting for some but it’s one of the few constants in her busy, hectic life that ensures that her business doesn’t suffer if her family needs her.

“You make sacrifices for what matters. It’s no different from what other entrepreneurs have to do.”

The startup lessons today’s top shows can teach you

Whether it’s a killer queen bent on reclaiming her ancestral throne or complex villains wrestling with their humanity, there’s a lesson for every entrepreneur in this year’s crop of popular TV shows. These programs are more than just entertaining; they provide inspirational examples (and in some cases cautionary tales) that will make any dealmaker, founder or mogul-in-the-making a better businessperson.

Here’s a look at the best fictional shows on right now and how they can help startups up their game before it’s too late. (Warning this post may contain tv spoilers).

Game of Thrones

Lesson: Find allies with similar goals

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It’s hard to imagine how a show about a medieval (yet magical) world inhabited by dragons and the undead could provide any real value for entrepreneurs at first glance, but the HBO show has a lot to offer.

Exiled princess Daenerys Targaryen, one of the main characters, is on a mission to reclaim her throne, which often pits her (and her army) against assassins, city uprisings and family betrayal. Her closest friends help her navigate dangers at every turn and without them it’s all too clear that this inexperienced warrior would surely have died long ago.

Like Targaryen, entrepreneurs should seek out experienced allies who can help guide, advise and nurture their ambitions. Forging alliances with the right people (and investors) is an important part of turning an idea into a million-dollar product.

Orange is the New Black

Lesson: Do your due diligence

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While betrayal, sleepless nights and poor diets perfectly sum up the day-to-day lives of the fictional characters on this Netflix show it could also easily describe the lifestyle of many early-stage entrepreneurs and acts as an important lesson for new startups hoping to find success.

The award-winning Orange is The New Black tells the story of inmates at Litchfield — a minimum-security, women-only prison — who must deal with everything from food strikes to abusive guards.

The show’s protagonist Piper Chapman is sentenced to jail for criminal conspiracy and money laundering charges early in the series and throughout her sentence learns, the hard way, how important it is to do her due diligence when picking friends and allies in jail. For instance, her failure to properly vet friends resulted in one later stealing her money from a short-lived prison panty business in season four and later time in solitary confinement. Entrepreneurs should look to Piper Chapman when bringing on new talent. It doesn’t hurt to make sure your staff are trustworthy and the people you partner with are worthy of your time.

Glow

Lesson: Don’t be afraid to reinvent yourself

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When you’re an entrepreneur and things don’t go your way it’s all too easy to end up wallowing in self-doubt. Failure, at any stage, is a gut-wrenching pill to swallow. Founders in need of inspiration about what to do if their company flounders should look no further than Glow, a fictional series about 1980’s female wrestlers in the U.S.

In the show failed actress Ruth Wilder decides to reinvent her career by taking on a role in a low-budget, traveling wrestling show. While wrestling isn’t exactly what she had in mind when she left her small town it turns out to be her biggest break thus far and finally gives her the success she craves. Like Wilder, entrepreneurs shouldn’t be afraid to pivot their business and use the skills they already have in their arsenal to start again.

Silicon Valley

Lesson: Always remain professional

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In an industry that’s consumed with power, prestige, and pride it’s easy to forget that one wrong move can throw an entire company into chaos. HBO’s Emmy-nominated Silicon Valley showcases just how complicated the startup world – and the individuals who work in it — can be. Egos can easily get in the way of success and threaten future opportunities.

The unforgettable Erlich Bachman is the perfect example of someone with an oversized personality that lands himself, and the company he represents, in hot water. His crude remarks and frequent off-the-cuff observations have alienated not just his coworkers at times but potential investors too. It’s too difficult to truly discern how successful Pied Piper — the company he works for — could have been if Bachman had been a little nicer in his dealings with investors and workers, but in a town where who you know is just as important as what you know it’s obvious it couldn’t have hurt the company’s chances either.

Westworld

Lesson: Keep employees happy and engaged

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Employees are the lifeblood of any company and Westworld knows that better than most. For most startups, it would be difficult to create, sell and promote any product without great staff, but for Westworld it would be almost impossible.

In this fantasy show about a futuristic amusement park where wealthy tourists can shoot, kill and otherwise abuse humanoid robots that act out western-influenced situations, employees represent more than just tools. They’re robotic staff who are the main attraction, keepers of the park and entertainment all rolled into one, which is why it came as no surprise to fans that they later revolted and attacked their creators.

When the park’s poorly treated robots go on a murderous rampage at the end of the series it’s an accurate, although unrealistic, representation of how a company call fall apart when its team aren’t treated fairly.

How Knix Wear founder shipped a million undies around the world

When Joanna Griffiths decided to quit her job at the ripe, ol’ age of 28 she never thought her split decision would one day lead her to launch Knix Wear , a Toronto-based lingerie startup, let alone net her over $2 million in sales, she admits.

But that’s exactly what it did and four years after starting the company on the floor of her living room she’s now shipping her high-tech, leak-proof underwear to women across the globe—everywhere from South Africa, to the U.S. and Afghanistan.

While her garments have garnered powerful praise from influencers since its 2012 launch—Metro News Canada, the Wall Street Journal  and New York Times, to name a few—Griffiths’ entrepreneurial journey is far less sexy, she confesses. The now thirtysomething encountered her fair share of problems during the startup’s early years and worked non-stop to get the business off the ground.

“It was scary,” she explains. “Being an entrepreneur is like a series of trade-offs, you’re always evaluating resources versus reward. The more prepared you can be for that type of lifestyle, the more you can think it through and know what your life will look like. I worked 24 hours a day and never stopped.”

The entrepreneur’s startup story is groundbreaking simply because through it she managed to create an apparel category that had never existed: leak-proof garments. Knix Wear was one of the first to market underwear to women who suffer from incontinence (light leaks), with company offerings later growing to include activewear clothing and period-proof panties for teens and adults.

A look at the breakthrough product that pushed Knix Wear into the limelight:

Her secret to success lies partially in capitalizing on the needs of what she felt was an underserved community. “I remember talking to women, who had kids, that would pick up Depends underwear because it was the closest thing they could find at the store and that resonated with me.”

Although her crowdfunding skills haven’t hurt her company’s overall success either. Since the company’s launch Knix Wear’s team has launched three online campaigns that have exceeded their crowdfunding goals. Her most recent campaign featured the company’s eight-in-one bra and raised more than $1 million on Kickstarter; the largest amount for any fashion project.

Despite her success, she’s quick to warn entrepreneurs about the perils of raising capital online.

“What I’ve seen happen is an expectation amongst entrepreneurs that if you put your product up it will sell like crazy. They underestimate the work it takes,” she says. “It’s probably the hardest work you’ll do in a 30-day period in your life.”

For instance weeks before the company’s latest campaign launched she and her team worked tirelessly to promote the company’s products, line up orders and respond to customers around the world within tight time frames.

In fact, if possible, she suggests new entrepreneurs avoid crowdfunding altogether until they have the capacity to fill large orders on demand. “We’ve learned the hard way from our early campaigns,” she says. “We had this amazing pre-market sales and momentum, but then spent the next nine months just trying to catch up and fill orders. People have to think long and hard about it. It’s not easy as everyone thinks it is.”

While the startup landscape has changed drastically since she launched her business, Griffiths is proud that her team has remained in the city she was born. Toronto entrepreneurs shouldn’t be too quick to leave the city behind these days, she adds. For anyone hoping to mimic her rise to the top she believes flying across the border is a must, but relocating isn’t necessary anymore and encourages entrepreneurs to explore options at home.

“There’s really nice growing and robust ecosystem that’s emerging [in Toronto]. There was definitely a time one-to-two years ago where we thought we had to move to the U.S. because I was getting that feedback from potential investors and now I’m not hearing that as much.”

Life lessons: Confessions from an entrepreneur who sold his startup

Life after an acquisition can be complicated.

For most founders, the possibility of landing a big exit is a good thing. It usually means a decent amount of cash and, in most cases, the chance to stick around as an employee or consultant long after the contract ink has dried.

While some end up missing the hustle and bustle of entrepreneurship, many find that working at a big company—after years of living the startup life—gives them time to regroup and tap into resources they could only have dreamed of when they were going at it alone.

No matter the outcome, the decision to sell a company can be an intensely personal and a difficult one to make. Robleh Jama, DMZ alumni and founder of Toronto-based app studio Tiny Hearts, knows the process all too well. The entrepreneur’s startup was purchased by Shopify in 2016.

After the buyout he and a few of his colleagues stayed on to join Shopify’s special project department where they now make experimental apps for new audiences. At the time of Tiny Hearts’ acquisition, Jama’s small, yet thriving, company had nine full-time employees and three part-time associates.

Before Shopify approached him about a potential acquisition he had never really considered selling the business. “It wasn’t really an idea I thought about,” he says.

His plan was to always grow with the company long into the future but as time went on, he noticed that scaling it would take more resources than his team had at their disposal. Shopify—an Ottawa-based company with offices in Toronto, Montreal, Waterloo and San Francisco—had connections around the globe to push his ideas to the next level.

“The acquisition was very organic,” he said. “[Shopify and Tiny Hearts] started off as a working relationship first and then grew from there. It was the best way to do it.”

Not everyone will find themselves in the same situation as Jama, but there’s nonetheless a few crucial things entrepreneurs should understand before taking an all-out company buyout, he explains.

Here’s his advice for entrepreneurs considering an exit and what they should know before signing on the dotted line.

Get your company ready by doing good work



A big payoff should never be the end goal for any entrepreneur, but if you’re looking to partner with or be acquired by another company you should make sure to create something of value on a regular basis, he says.

“It all starts with and ends with producing great work,” he explains. “You’ve got to think what value does a company want or look for. It’s better to think about it that way instead of reverse engineering an acquisition. That won’t work,” he explains.

At Tiny Hearts, creating great products meant making sure his company always stayed on top of new trends in the mobile industry and applied them whenever possible to upcoming projects. It also helped Jama, he admits, that he was personally invested in learning as much as he could about mobile-based applications in his free time.

Another piece of advice? Make sure to network with as many people in your industry as you can and stay grateful. “We met people at the DMZ that are still friends of mine to this very day and connected me with other people in the field.”

Wait for the right partner



Just because a company makes an offer doesn’t mean you have to take it, he explains.

Jama and his team worked with Shopify on several projects beforehand and were well acquainted with the company’s products and, more importantly, how they could help each other elevate the work they were already creating.

He also knew how he would personally fit into its company culture as an employee. A fact that he says founders shouldn’t be too quick to overlook. “I knew what they were like. I don’t think I could work at a company that wasn’t Shopify. I was looking to level up and learn to build products at scale and they were the ones that could do it.”

Not to mention that he’s also happy with the work he’s doing. Any role you or your team take on post-acquisition should be discussed in detail before any contracts are signed, he explains.

“Working at Shopify is like a honeymoon that doesn’t end because the team I work with is autonomous and doing what we used to do at Tiny Hearts—pumping out mobile products. We’ve been given the resources to do what we’re most passionate about so we can just focus on creating  innovative and experimental products.”

Seek out legal help ahead of time


There’s no shame in asking for help, especially if it involves money. Exits can mean a host of new problems, which can sometimes include doling out money or company shares to employees and should be taken seriously.

The best thing for companies to do is find someone who can help lay everything out in black and white and take emotions out of the picture, he says. “Find someone you trust and go from there.”

Last, but not least: Do your homework



Jama and Shopify executives made sure the buyout process went slowly. It took almost a year between initial talks to a contract signing.

“The idea was floated, casually, when we started working together, but we didn’t want to rush into. We said let’s continue to work together to see how it goes. After we worked with the team on an app called Frenzy we realized that Shopify was what Tiny Hearts could become if it were on steroids and were on board.”

Luckily over the years Shopify had acquired several local companies before Tiny Hearts, which made the process that much easier for Jama and his team. “Shopify had done this a handful of times of times so they made the process super smooth from the conversation to getting the deal done to transitioning, but we made sure to talk to people [clients, staff, industry professionals].”

Breaking the mental health taboo

The heavy toll business ownership can take on one’s mental health is a dark secret rarely shared. A fear of failure, constant pursuit of greatness and long days followed by even longer nights can push even the most ambitious entrepreneur to their breaking point.

In today’s world where the trials and tribulations of even fictional founders are idolized, it should come as no surprise that psychological health is often all but ignored. In fact, a recent study found that a whopping 72 per cent of entrepreneurs self-reported as having mental health concerns, not a surprise for many in the startup community that have already come face-to-face with high rates of Founder’s Blues.
However it’s one that Abdullah Snobar knows all too well. The executive director of the DMZ at Toronto Metropolitan University — the number one university-based incubator in North America and third in the world — and founder of TEDxRyerson is someone that many could easily describe as “successful” and ironically a strong proponent of (surprise, surprise) mental health services. More importantly, he knows how useful it can be for people like himself in the startup industry where appearance can sometimes trump reality.

“There’s a misconception that people who are Type-A and successful are free from mental health challenges. If a person has a busy, fulfilling life and looks accomplished and happy from the outside, they must not struggle with mental health issues,” he says in an op-ed originally published in the Globe and Mail.

“It’s a misconception that’s reinforced every time I browse my Instagram feed, LinkedIn profile and even walk past the sea of smiling faces at various conferences. Everywhere I look, I see no obvious signs of mental health stresses. And herein lies the problem.”

Enter: TranQool, a Toronto-based startup that connects patients with therapists for video chat sessions. The goal? By reducing physical barriers, costs and stigma that accompanies mental health counselling, the startup wants to give anyone the ability to seek out the help they need no matter where they are.

A lot of times we [entrepreneurs] actually hide ourselves in the work that we do and avoid the reality of life by working extra hours, which sometimes leads to burnout and depression,” said Chakameh Shafii, the company’s co-founder and CEO

Through the company, Canadians can set up a free customizable profile that lets them detail their concerns. Afterwards, patients are then matched with a therapist within five minutes.

Not everyone may feel comfortable with seeking out therapy online, but it’s a unique technological solution to a problem that has long plagued the startup space. For those who don’t have a personal self-care plan simply recognizing how crucial mental health wellbeing is to long-term success is the first step and a smart way to combat the dreaded Founder’s Blues before it ever takes hold.

If you’re a DMZ entrepreneur looking for more ways to improve your mental health, you can access the free counselling sessions the DMZ is providing through our community partner TranQool – an online tool connecting you with accredited cognitive behavioural therapists.

For other individuals looking for local mental health services there are a variety of local resources offered by the following institutions and the city of Toronto.

Mental Health Helpline
Information about mental health services and supports in your community and across Ontario.

Distress Centres of Toronto
Telephone call centre for people needing emotional support, crisis intervention and suicide prevention.

Community Resource Connections of Toronto
Search directory for addictions and mental health programs, housing, crisis services, and basic needs services.

Oolagen Community Services
For youth 13-18 years of age and their families who live in Toronto that require mental health assistance.

Steps to building a diverse startup

For more information on how your startup can build a truly diverse and inclusive company, check out the #ChangeTogether Diversity Guidebook, a collaboration between TechGirls Canada and TWG.

Below are some tips for building diversity and creating an inclusive environment for everyone.

Make it a priority… from the beginning

Building a diverse team is always easier when you start from the beginning. Take a look around you or on the team page of your website even if you’re part of a team of four or five. Ask yourself ‘how many women are there on my team?’ or ‘how many people of colour are there?’ These ratios can seem insignificant when you’re part of a small team, but it will be harder to attract and retain talented staff of various backgrounds, genders, sexualities and identity groups when you’re a rapidly growing team of eight and your plan to have a more diverse team results in a token hire.

Look outside your network

Are you in the middle of hiring and not seeing a diverse pool of applicants? Chances are you haven’t looked outside your circle. When growing your startup, it’s understandable that you don’t have time to play hiring manager, but you shouldn’t rely on asking a few friends if they know anybody. This only creates a higher chance of teams that look or think the same.

One of the ways to go outside your circle is by expanding where you advertise. Set a goal to post an upcoming position to at least five or more job portals. Before advertising this new position, make sure you review the language in the job description for inclusivity. The TechGirls Canada and TWG ‘Diversity Guidebook’ suggests adding an inclusion statement in the description. For example, “we encourage applications from candidates of colour, women, queer candidates, candidates with caregiving responsibilities, immigrant candidates, transgender candidates, and candidates with disabilities.” This can help you cast a wider net of applicants.

Values over quotas

An inclusive startup isn’t about filling quotas and following affirmative action initiatives. It’s about building a team that extends beyond what your startup sets out for its customer base. And when you foster diversity and inclusion, you bring a range of perspectives that can help encourage creativity and better connect to your clientele.

The #ChangeTogether Diversity Guidebook suggests creating strategies for increasing legitimacy within your startup. This can include creating safe spaces for discussion among marginalized employees and training a staff member to serve as a key source of support for your team.

Seek partners

Implementing steps to improving diversity and inclusion doesn’t have to be a solo effort for your startup. Organizations like TechGirls Canada work to breakdown silos and advocate for resources and funding to catalyze inclusivity. Their ‘Portraits of Strength’ initiative features women who’ve helped break down barriers for underrepresented groups in the tech sector. Many of these women are available to mentor other entrepreneurs who are looking to turn their inclusivity plans into actionable items.

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