HOW EMILY O’BRIEN BUILT A SUCCESSFUL BUSINESS, AND A 29,300 PERSON INSTAGRAM FOLLOWING IN LESS THAN 7 MONTHS

Emily O’Brien is not your average 27 year old. In the past 7 months she’s launched a business (Gatherr) grown her Instagram following to 29.3k people (@territuesday) hired three staff, and adopted an adorable puppy (Pounce).

We sat down for a latte at Bugigattolo, a restaurant owned by one of her Instagram partners, to talk about Mad Libs, old school hip hop, and what it’s like to be a successful female entrepreneur in an industry our parents’ generation might never understand.

EMILY AND HER TEAM AT GATHERR ARE ON A MISSION TO TAKE OVER THE INSTAGRAM WORLD, ONE CITY AT A TIME.

Gatherr, is a social marketing secret weapon. They do everything from full account management to providing clients with the licence to use proprietary software to help them accelerate their growth.

We jumpstarted the interview by attempting to play a round of Emily’s favourite 80’s throwback game:

MAD LIBS

People describe me as: <wild> and <forgetful, hyperactive and mysterious> because <I’m always happy all the time and people are like “I don’t understand you’re life”>

Alexis Dean (AD): Hold up, we need to pause the Mad Libs. Why do people say they don’t understand your life?

Emily O’Brien (EO): I’m very good at making things work out, at making things fall into place so everyone can benefit.

AD: I think that’s a common entrepreneurial trait: just make it work, no matter what “it” is.

EO: I’m an awesome multi-tasker

AD: Back to the Mad Libs…

EO: Yesterday was an amazing day because

<I met up with my friend from Columbia. He has an elite concierge business. I met him last year when I travelled down there with a couple of friends. My one friend Lindsay, who does wellness coaching for Tony Hsiu and works on Richard Branson’s Island, she introduced us. My friend was up here to visit, but it wasn’t like when we were in Cartagena. He has this crazy business where we got picked up in helicopters down there, it was a wild trip. I couldn’t sleep last night, so he told me to watch The Secret. I got about fifteen minutes into it before I switched to Dragon’s Den.. I love Dragons Den. I’m not sure about The Secret yet.>

AD: Ok, that sounds like an average Tuesday for… no one. That sounds amazing. So the Mad Libs didn’t last too long. I’ll have to work on reigning it in for the next interview.

EO: I’m asking my friends to fill out Mad Libs for my website bio. (author’s note, you’ll be able to see the Mad Libs bio soon at gatherr.ca)

HOW SHE LAUNCHED GATHERR

AD: So let’s take a trip down memory lane to when you launched Gatherr just seven months ago. What were the first few steps that you took to get your business up and running?

EO: I did a lot of research. Basically living and breathing Instagram for the past two years. I had a business partner who helped me build the app, but he sold his half because he’s busy making too much money with his Google Adwords business. Throughout the two years before I launched the business I researched everything: I really wanted to find out what I could do differently.

“I READ A LOT OF BUSINESS BOOKS, BUT NOT TOO MANY BLOGS. I CAN’T STARE AT A SCREEN ALL DAY, I DON’T WANT TO BE BLIND BY THE TIME I’M 30.”

AD: In those two years before you launched, when you were researching, were you still working at a day job?

EO: My business partner actually paid me a salary to do the research for his company. I got paid to learn and travel the world. I started to work on the program, it was my responsibility to get beta testers, learn what was working, what wasn’t working. I didn’t build the app and do the coding myself, we had someone in Florida do that part. I was very very lucky.

AD: “Lucky”sounds like an understatement! That’s incredible! How did you find your business partner?

EO: I met him at an entrepreneurial event. It was actually more of a program, called the Strategic Coach. It was founded by a gentleman named Dan Sullivan, and he created a program that helps you find your unique ability, and grow your business using your skill set. I was in that program and that’s how I found my business partner who’s a little bit older than me. He was in the 10x program. I also have a couple of friends who are, like, 30, and they’re millionaires right now because they took the Unique Ability course. In the highest level of the program the fee is $20,000 for the year, for four sessions that are four days each.. You basically end up paying $5000 a day for the sessions, but at that point you’re making so much money that it’s worth it.

(Author’s note: you can learn more about the Strategic Coach here, but I should warn you that you need to earn a minimum salary of $100,000 to enrol in any of their programs. Not $100,000 gross revenue for your company, $100,000 personal salary… so, this might not be the best program for every startup entrepreneur, but if you can afford it, it comes highly recommended!)

HOW TO FIND MENTORS AND FREE LEGAL ADVICE

AD: Do you have a mentor?

EO: I work with Startup Toronto a lot. Gabriella, the founder is a lawyer, so I go to her for my legal advice. Craig the director is also a mentor, and he helps me with the annoying things I don’t like doing. I didn’t really want to write a business plan but he motivated me to do it.

AD: Your mentors sound fantastic. I’m going to ask a direct question that lots of people will want to know the answer to, but you don’t have to answer it if you’re not comfortable: Are those paid mentors? Are you getting free legal advice from a qualified lawyer? (Author’s note: this is like the holy grail for entrepreneurs. Lawyers are $$$ expensive but essential to every startup)

EO: I’ve been getting most of my help for free. I manage their social media accounts, and once a month I run the Startup Drinkup, where founders get together and hang out. (Author’s note,  Startup Drinks usually held second Tuesday of every month)

AD: Bartering for services has worked for me too. I think if you can make that happen, it really helps when you’re first starting out.

“YOU’VE GOT TO HUSTLE FOR IT THOUGH; IF YOU DON’T ASK, YOU DON’T GET.”

ON FINDING HER FIRST CLIENTS (AND HOW YOU CAN TOO)

AD: How did you get customers, and how do you continue to attract customers (aside from the obvious 29 thousand people who already follow your personal Instagram @territuesday)

EO: Just by being friendly and getting out there. I always want people to try new things. I’m very encouraging. I’ve always been a very nice person, for the most part, except for when I was kind of a dick in high school. I lived in Liberty Village for a long time. When I lived in Liberty I’d just always go out and be very friendly, I’d refer people to stores, I didn’t even know what I was doing or how it would pay off in the long run. I was able to establish a lot of relationships that way.

“I SEE MOST OF MY BUSINESS RELATIONSHIPS AS FRIENDSHIPS.”

AD: So, would you say most of your clients come from real social interaction as opposed to social media interaction?

EO: Oh yeah. Your real life social presence is way more important. I go crazy if I’m sitting inside for too long, I need to be out making face to face contact.

“SOCIAL MEDIA CAN BECOME ANTI-SOCIAL IF YOU’RE NOT DOING IT RIGHT”

HOW TO KILL THE COMPETITION WITH KINDNESS

AD: What’s your UVP (Unique Value Proposition)? What makes your service better than the competition, and how have you grown your business so quickly?

EO: I believe in having a very friendly personal connection, all the time. I visit my clients, whereas a lot of companies won’t. They’ll just call or email. I think it’s really important to get to know not only the person making the decisions, but also the employees at each company. So you can learn from them, and build a stronger strategy for their Instagram accounts.

AD: Real interactions with real people. I love it.

ON NEVER MISSING A MOMENT, KNOWING YOUR PERSONAL MISSION, AND STAYING TRUE TO IT

AD: What’s your mission statement?

EO: Never miss a moment. I don’t want my company to miss a moment that other people should see, that other people need to see.

AD: You could put that on the wall

EO: What wall?

AD: Any wall. Like the bathroom, or the living room, or just the office. You know, any wall. It’s a good quote.

EO: I like it. I have a passion for helping people capture moments that matter.

“INSTAGRAM’S NOT JUST ABOUT THE PRODUCT, IT’S ABOUT THE PEOPLE, AND CREATING AN EMOTIONAL RELATIONSHIP. PEOPLE BUY FROM PEOPLE, AS OPPOSED TO A BRAND.”

People also want to buy from brands where people are treated well. So it’s important to showcase the happy employees, showcase the freedom that they have, and their ability to express creativity within their organization. If you’re hiring, people are looking at your brand. It’s so important to make people feel included and important, and I think that makes a really cohesive and happy team.

AD: I feel like you just wrote a manual on how to develop a positive company culture.

EO: Sweet.

AD: Autonomy, inclusion, importance, relevance… you’ve got it all going on at Gatherr.

AD: What’s the long term plan? What’s your vision?

EO: I want to expand to Montreal, then Calgary, then Vancouver. And then find other people like me to do the same thing all over the world.

ON MOTIVATION & HOW TO LIFT YOURSELF UP WHEN YOU’RE DOWN

AD: What motivated you to start your business in the first place?

EO: The desire to express my creativity. I’ve always been someone who has a lot of ideas, and I always knew that I didn’t want to work a 9-5 job doing something that I didn’t really love. I have no problem working, but I only want to work hard if it’s something I’m passionate about.(Author’s note: THIS completely describes the Millenial workforce: passion for our work is essential)

AD: How do you motivate yourself on days when you’re really struggling. I don’t know a single entrepreneur who doesn’t have those moments of wondering what the heck we’ve gotten ourselves into. What do you to lift yourself up and get back to work?

EO: I play loud music, have a glass of wine, dance around my apartment. I really like to hang out with my dog, so I’ll take the dog for a walk. It’s nice to take a break from talking about work, and just go to a hip hop club and tear up the dance floor. I also like rap battles. And Mad Libs. I love Mad Libs.

ENTREPRENEUR IDOLS AND HOW TO BE FRIENDLY WITHOUT BEING A PUSHOVER

AD: Do you have an entrepreneur idol? Who is it and why are they worth idolizing?

EO: Arlene Dickinson from Dragon’s Den, and Jordan Belfort from “Wolf of Wall Street”. Did you see the great company culture in that movie? (culture development jokes, lols) Arlene really cares about helping other people and helping people’s businesses grow. She’s on the show to help the viewers learn too. I get tons of advice just from watching that show. I want to be able to do that down the road, to help people like that. She’s funny and smart and she has just the perfect amount of toughness.

“YOU CAN’T BE A PUSHOVER IF YOU WANT TO RUN A POWERFUL COMPANY.”

AD: There’s definitely a common perception that as a woman in business you can’t be too nice, because you’ll be considered a pushover, but you can’t be too tough, because you’ll be called a bitch. How do you find the balance?

EO: It’s hard. People will take advantage of you if you don’t play your cards right. I was definitely too nice in the beginning but I’m more careful now. Even if I’m nice I still mean business. I don’t mess around anymore. I use a little reverse psychology – I think you should let people think that they’re going to be able to take advantage of you, even though you’re already preparing to prevent that from happening. And you can do it all with a smile on your face.

AD: You definitely need to know where your line is and how to behave when the line is crossed.

EO: It’s way too easy for guys to suddenly be like “calm down, you don’t need to be such a bitch about it” as soon as you assert yourself. It’s a totally ridiculous double standard. It’s just something that you have to learn to deal with over time. I learned from experience, and I think everyone figures out their own balance.

ON KNOWING YOUR SH*T AND JUST GETTING IT DONE

AD: What’s the most challenging part of running your business?

EO: Doing the things that you don’t want to do, but that are really important. I hate accounting. I hate all of the legal things. I know I have to though, because it’s really important to really know your own business. I didn’t pay attention to it for a long time but now I’m actually on top of it. When you’re a creator your mind just wants to create, you don’t want to do the back end. It’s frustrating, but you really have to learn how to do that stuff before you pass it off.

“YOU CAN’T JUST BE LIKE “OH, MY ACCOUNTANT WILL DEAL WITH THAT”, WHEN YOU DON’T EVEN KNOW WHAT YOU’RE DEALING WITH. OR ELSE YOU CAN GET COMPLETELY SCREWED OVER.”

I know people who’ve been robbed by their accountants. Also, insurance is just so important. Even in social media, you need to have insurance in place, even something minimal. I’m always thinking about how things will scale too.

AD: Preach.

ON HER BUSINESS PHILOSOPHY, PASSION FOR OLD SCHOOL HIP HOP, AND LISTENING TO YOUR HEART

AD: Do you have a business philosophy?

EO: hmm… it would probably be like a Tupac quote. Or another hip hop quote. I just wrote an article about how classic hip hop shaped my life (Author’s note: You can read this stellar piece of writing here). Here it is:

“STAY FAR FROM TIMID, ONLY MAKE MOVES IF YOUR HEARTS IN IT, AND LIVE THE PHRASE ‘SKY’S THE LIMIT’”

– NOTORIOUS B.I.G., SKY’S THE LIMIT

AD: I’m feeling so inspired already. Rap for entrepreneurs, I love it!

AD: Is there anything else you think it’s important for new entrepreneurs to know?

EO: Don’t worry about what other people think, especially people who aren’t entrepreneurs themselves. Don’t let them tell you what they think won’t work, especially when they can’t prove it. If there’s one thing that will stop you, it will be believing them.

EO: It took a year of me battling my parents for them to understand. They work in jobs from the 80’s and 90’s, they don’t know how money can be made now, but they still questioned my work and my schedule. That’s part of why I blog. It’s your own brand, your own body.

“DON’T LET SOMEONE ELSE TRY TO TELL YOU HOW TO LIVE THEIR LIFE IN YOUR BODY. IT JUST DOESN’T MAKE SENSE.”

AD: That’s some of the best advice I’ve ever heard. Thank you for taking the time to hang out and share your entrepreneurial wisdom! I’m so glad I met you, and I can’t wait to see what’s next for you and Gatherr.

EO: Thanks, this was so much fun!

Author’s note: I loved Emily’s old school rap quote so much that I’m going to end this piece by quoting another amazing rap artist, featured in Emily’s gatherr.ca blog about old school rap:

“IF YOU’RE SCARED TO TAKE CHANCES YOU’LL NEVER HAVE THE ANSWERS”.

– NAS, TRUST

You can reach Emily at emily@gatherr.ca, check out her Instagram account @territuesday, and learn more about her business at www.gatherr.ca  You can also join Emily on one of her infamous photowalks for mentorship, advice and fun.

Alexis Dean is the founder of Dovetail Team Building and Training, where she and her team of Directors of Culture For Hire help people authentically connect with their colleagues, have fun at work while still making their business profitable, and make a difference in their communities.

Alexis is also the author of What If You Fly, this website and blog for intrepid and aspiring entrepreneurs. You can reach her at: alexis@dovetailteambuilding.com, and see her Instagram account @dovetailteambuilding.