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In Startup Talk episode 14 I speak with Emily O’Brien founder of Cons and Kernels about growing up entrepreneurial. Emily gives us 3 great Instagram tips and talks about how losing everything turned her life around. We also discuss how she got a Dragon as an Advisor, the Dragons Den audition process, and the importance of being authentic.

Direct from The Six, world renowned, Canada’s largest city, with Canada’s biggest thinker, visionaries and hustlers. This is Startup Talk Episode 14, featuring the founders, funders, innovators, and community leaders who’ve led Canada’s start-up ecosystem right here in Toronto. You’ll hear the challenges, the failures, the successes. Toronto’s Startup podcast gives you the full story direct from the entrepreneurs and influencers who’ve made a difference. Now, the host of Startup Talk Episode 14, the founder of Toronto Starts, the Startup coach.

Startup Coach:  Welcome back to Startup Talk Episode 14, it’s the Startup coach, and on this episode, I talk to Emily O’Brien, of Cons and Kernels. What it’s like to be flying high and lose everything, building a business from prison, getting a Dragon as an advisor, getting on Dragons Den, and Instagram TV and more, all on Startup Talk Episode 14.

Startup Coach:  Welcome back to Startup Talk, this is the Startup coach here. Today, I’m with Emily, from Cons and Kernels. Welcome Emily.

Emily O’Brien:   Hey, thanks Craig. Good to be here. Bright and early.

Startup Coach:   Bright and early, yes it is. The sun is shining on a lovely spring day finally.

Emily O’Brien:   About time.

Startup Coach:  Why don’t you tell all the entrepreneurs about Emily growing up. Where did you grow up, were you a handful for your parents?

Emily O’Brien:   Sure. I grew up in Hamilton, Ontario, so it’s about 45 minutes west of Toronto. I went to Catholic school originally and then, once I got to high school, I actually switched from Catholic to public, because I was struggling there, and when I went to public school, I got my grades up and got into university. When I was a little kid, I always had lots of energy, was always willing to learn, and always going to camps, things like that. Then once high school hit, I did the high school thing, and got into the drugs, the booze, the bad crowds, things like that, but I’m here now, and made it out alive, so that’s good. I’ve also done a lot of great work in my life, so …

Startup Coach:  Absolutely. You were always had an entrepreneurial spirit.

Emily O’Brien:   Always.

Startup Coach:   Because I’ve seen you, you’re always doing three or four things. Tell me how that affected your life when you were growing up. What did you do to make money?

Emily O’Brien:   When I was really young, I knew I wanted to buy a lot of junk food, because my mom didn’t have junk food in the house, so I was like, I really want chocolate bars, so that’s what prompted me to get my first job. I think it was maybe 10 or 11. I got a job delivering flyers around the neighbourhood, so I’d haul out this wagon, and drop it off, and then I actually got fired because of one day I decided the people always told me not to drop them off. They didn’t like the flyers being delivered to their house. They had signs that said no flyers please on their window, and so I ended up throwing them out and I guess they saw me throw them out. So I got fired.

Startup Coach:    Well, I think there’s many a story. I used to deliver papers as a boy, and all sorts of things like that, yes. And we do stupid things when we’re young. Cons and Kernels not your first business …

Emily O’Brien: No.

Startup Coach:   So what would you consider your first business?

Emily O’Brien: My first business was a company called Gather, that was based out Of Liberty Village in Toronto. After I graduated university, I worked for various marketing companies. I even worked a corporate job. I really figured out there that I was great with human interaction, and just building human relationships face to face, and so after I did marketing jobs and worked corporate, I decided to actually start my own business in Toronto, because I loved seeing other people’s reaction to when they got a new follower or they’re posted really well online, and it made them really happy, and it encouraged them to keep building their business, so I liked helping them do that. And that was in 2014, so I did that for about three years, I would say.

Startup Coach:    So you’ve done a lot of work helping companies with social media, Instagram in particular. What types of things did you find that most companies did wrong?

Emily O’Brien:      Over posting for sure. And not structuring the copy of their posts properly. They would often jam in together too many hashtags, and that really explained the picture, and also sometimes not even humanize the account enough. They would just make it all about the product without trying to build a human interaction, human experience with other people on there.

Startup Coach: That brings us around to three tips for startups building a brand and engaging people on Instagram. What is your Instagram tip number one?

Instagram Tip #1

Do more outreach than posts

Emily O’Brien – Cons and Kernels

Emily O’Brien:   Would be to do outreach more than posts. I think by writing … and actually writing authentic comments on other people’s posts, not just like smiley faces and emojis, and love this, even if it is you, try to actually write something that the person will remember as opposed to just an emoji.

Startup Coach:   Great. Tip number two.

Instagram Tip #2

Use Instagram TV

Emily O’Brien – Cons and Kernels

Emily O’Brien:   Yep. Tip number two is use Instagram TV. Instagram is actually rewarding people that are using Instagram TV because they’re trying to compete with YouTube, so if you have little mini-episodes about how you run your company, or just little tidbits of information that are short. It has to be under 10 minutes. My Instagram vidis have done very, very well, and so combining that with still images, and they actually show up, the preview of the IG TV episode shows up on your Instagram feed.

Startup Coach: Nice, Instagram TV is tip number two. What is tip number three for Instagram?

Instagram Tip #3

Use Humor

Emily O’Brien – Cons and Kernels

Emily O’Brien:   Tip number three for Instagram is … what am I doing right now? Use humor.

Startup Coach:    Humor.

Emily O’Brien:     Humor.

Startup Coach:    Can you give us an example?

Emily O’Brien: I like to make fun of the challenges that I go through. And I think too many people online, they post this picture perfect image of how great they are and how awesome things are, but they don’t actually shed light on everything else that’s going on. And I think once you actually share maybe a little bit more … I’m not talking about oversharing, like sharing where you buy your underwear from, but maybe share some of the obstacles, because going through obstacles is how you get the most growth as opposed to just learning how to lose I find, has been so important to me, and it propelled me forward as opposed to just like, oh this is how you win at something, or this is why we’re the greatest. It’s like wow, this is how we messed up, or this is what we learned from this thing. So I think shedding light more on your struggles, and your difficulties, without being pessimistic and negative I think is important.

Startup Coach:   So self-deprecating, letting people know that it’s a journey. Life isn’t fantastic, and make fun of yourself once in a while.

Emily O’Brien:   Yeah.

Startup Coach:   Awesome. When did things change for you? You said you had to get used to losing. What happened?

Emily O’Brien:   In 2014, after I moved to Toronto in 2013, I got mixed up in the partying scene, like it was part of my work, that’s how I justified it. I ended up going out just about every night, and I really didn’t like being alone. I was going through a family issue, and I’d always drank and used drugs, but never to the extent that I used them when I moved to Toronto. Because it was everywhere and then when my family started going through something, this drug use was exasperated. But I still somehow ran a business. Definitely not to its full capacity for sure. I didn’t really have any tools for growth, or I didn’t really want to grow it, I was just kind of happy where I was because in 2015, I actually was in a relationship and ended up being convinced to go on a trip to bring drugs back over the border from St. Lucia to Canada.

I actually was in a relationship and ended up being convinced to go on a trip to bring drugs back over the border from St. Lucia to Canada.

Emily O’Brien – Cons and Kernels

Emily O’Brien:   This was a terrible choice, not only because I loved my traveling the world, but also because it was very dangerous. And I put my family through a lot of hardship and grief, and I was on bail for two and a half years, and that was really long. I just wanted it to be over with, but when you learn these lessons, you don’t necessarily learn them very easy. Sometimes you’ve got to suffer through the hard parts. That was definitely long.

Startup Coach:   How did you turn this down time into something positive?

Emily O’Brien:    By quitting drug use and alcohol use for good. Not thinking about using in the future, and really having gratitude for what I have because there’s so many people in the world that don’t have that. When I got arrested, and then when I finally actually did prison time, I had so much support. My family lived close. Not everyone even has family that wanted to visit them. And then my professional network always writing letters, and offering to hang out with me and things like that. And also developing empathy for why humans do things the way that they do, like when I went to prison, I met so many people that had maybe made one bad decision, and it’s not because they had evil intentions and they were trying to cause harm. It was more of an emotional decision, trying to protect themselves or protect their family. So it really helped me understand human behavior and abandon any grudges that I had against people for doing things maybe in the past. So that really gives me strength and … should I talk about losing now?

Startup Coach: Yeah, sure.

Well, when I got arrested, I lost a lot of things. At this point, when I got arrested I was drinking nearly every day.

Emily O’Brien – Cons and Kernels

Emily O’Brien: Okay. Well, when I got arrested, I lost a lot of things. At this point, when I got arrested I was drinking nearly every day. But once I was put on house arrest for bringing drugs into the country, after I learned that this is one of the most serious offenses in the criminal code, little did I know. I lost my freedom, so I had to have notes written for me for my mom, and I didn’t like that, so all of the time I didn’t really listen to those rules, which led me to being arrested again, and thrown in jail for the weekend. After that I smartened up, but also lost my dog, I lost a lot of money, and I lost time. I would say I didn’t lose time. By going to prison I actually gained time. I think the time on bail was just like time spent in limo, where I wasn’t really ready to change, but I wasn’t ready for what was coming, either. So I was stuck in this place.

Startup Coach: And when did that change?

Emily O’Brien:   That changed after I got arrested the second time, and then I realized I would not be getting back out of jail, so I was staying in a jail in Hamilton and then I eventually went to a federal prison. My mindset changed actually before I went in, that I was going to make the most of this opportunity and I was going to pull together as many resources as I could. Not just a manageable time, but actually a productive time.

Startup Coach:              So how did you do that?

I actually ended meeting someone by chance at one of your TorontoStarts events, and I think it was a blessing from God, … and I was like, oh my gosh, this is like, holy, holy crap.

Emily O’Brien – Cons and Kernels

Emily O’Brien:    Well, I actually ended meeting someone by chance at one of your events, someone that worked for a company called Klink Coffee and I think it was a blessing from God, because I just happened to be at this event, and they happened to be there, and someone that was working at this booth happened to just get out of the same prison for the exact same crime, and I was like, oh my gosh, this is like, holy, holy crap. I have to be friends with this person. She was so helpful. She was a good mentor to me, and coached me about what was to come. Then when I got there, I just started reading, and I knew I was going to go there and create something, based off my experience, because I knew I couldn’t just be the only one.

Emily O’Brien:    I knew that I was raised in a way that … my mom taught me to always fight through things, no matter what, and that’s what I did, and to just never give up, and I also knew that I was a good person. I did a bad thing on one day of my life, but I knew I had done amazing things for other people, all the other days. So I knew that that was worth something. I knew I had a lot of potential if I just stopped being mad, and took responsibility and then eventually, just ditching the alcohol and the drugs.

Startup Coach:    So you’ve made this decision to change, and now you’re inside.

Emily O’Brien:   And now I’m inside.

Startup Coach:   What happens?

Emily O’Brien:   On Super Bowl, on March, 2018, we had a party, and this is a very PG party. You don’t have beer or anything like that in prison, so we had pop and chips, and prison parents, AKA correctional officers, that was cool. And then I noticed all the girls, we were popping popcorn, and then they were making their … we had a food budget, an allowance for food in there, and we can pick what we want from this item list, and people would order spices and put their own spices on the popcorn. I thought it was super creative and how it brought women together, encouraged a sense of community, and it was a blank canvas for creativity, for culinary creativity. It’s a healthier snack too.

Emily O’Brien:    There’s limited exercise and the anxiety levels are high, which then increases … it’s a breeding ground for rampant eating disorders. It’s a stressful situation. Prison is stressful. I thought maybe I’ll start a popcorn company, because it’s such a simple thing, but can build it so that I can hire people that have been to prison, because if I didn’t have the resources that I had, I’d be having a much more difficult time, so I want to spread the resources that I do have.

Startup Coach:   So similar to what Klink Coffee tries to do where they’re rehabilitating people back into society with jobs, you’re hoping to do that with Cons and Kernels?

Emily O’Brien:   Yeah, because unfortunately Klink Coffee is, they closed down. So they lost some of their funding, that’s why I wanted it be like a social enterprise. You’re more self-sustaining. You’re not dependent on handouts

Startup Coach:  Indeed, and a lot of people want to run social enterprises and change the world, and I think that’s admirable and great, but the business needs to be around a year, two years, three years from now if you’re going to change the world. You still have to make revenue somehow. Selling popcorn, great. You’re making popcorn inside, how did that turn into a company?

Emily O’Brien:    One of my friends Ryan, who I did work with in the past in Toronto, he had been a great support for me, really good friend, and I told him about this. He’s like, “Oh my god, let’s put together a marketing plan,” so he helped me with market research. Because obviously, popcorn business is great, but it’s only worth finding the investment if you know there’s a space in the market. We did some more broad research, and he would also send me recipe ideas and I would experiment with these cool, new, more 2019 foodie recipes as opposed to just the regular stuff that you see on the shelves, the sugary stuff, because I wanted to make it healthier. And then we sketched together logos through snail mail, talked about it over the phone, and then he would send me something, and then eventually we got a graphic designer to do it up. Then I did my first event actually as an inmate, so I had to go back to the prison that night, but the warden actually let me out. Pretty cool.

Startup Coach:    I what was your first event?

Emily O’Brien:   It was an event called Take Back the Night, a women’s empowerment event for people that had been victimized or marginalized, or just had some sort of struggle, which I definitely did. I know my role in this was significant, but I also didn’t create this plan. I know that my substance abuse had made me a target, as well as other things. I had extensive travel experience, and I was free spirited, and I’d traveled with other people before, so the person that asked me on this trip clearly knew this, and so it was a number of factors, but …

Startup Coach:    How did your first event go?

Emily O’Brien:   Went really well. All the samples were gone, so I couldn’t actually sell anything, because I was still an inmate, so I wasn’t allowed to handle money. But no, it was really good. I had little postcards to hand out, and I basically said, “Launching spring, 2019.”

Startup Coach:    Did you get emails from that. Is that when you started your email list?

Emily O’Brien:   Yeah, we had the email account set up, so Ryan managed that, and so we would go over it over the phone, me we had a little website set up called Cons&, and that’s where my prison blog was, so people really liked reading about the stories behind bars.

Startup Coach:   You weren’t able to sell, but you’re building your following on your blog, Cons and Kernels, which is great. I always tell people it’s never too early to start building your following, even if you’re not quite sure what your product is or you’re in stealth mode. When did you actually get to start selling?

Emily O’Brien:   When I was granted day parole. That was December 3, 2018. I just jumped right in. When you come out on parole, your parole offices wants you to have a normal job. Typically inmate entrepreneurial ventures are not … like what I’m doing. They’re usually some sort of sketchy thing. It took me a while to prove the business to my parole officer, but she supports it now, which is great. It’s nice to be able to get along with her. December 3rd, and now we’re about $8,000 in sales currently.

Startup Coach:   A month or total?

Emily O’Brien:    Total.

Startup Coach:    All right. That’s only been four months, so …

Emily O’Brien:    I know.

Startup Coach:   Yeah, that’s pretty good, and you’re out running this business, and somehow you ran into Dave Chilton of Dragons Den. What happened there, and how did it get him on board as an adviser?

Emily O’Brien: When I was in prison I did a lot of reading. I was like, I’m just going to curate my own degree, and one of the books that I read was The Wealthy Barber, and I also watched Dragons Den a lot when I was in prison. I was always watching it at 11 a.m. on CBC during the week, and I always thought to myself maybe I can take this popcorn company and get on this show and set an example for anyone that’s coming out of prison to show them what they can do if they just abandon all the BS, and don’t get involved in prison subculture and everything like that. Then I ended up reading Dave’s book, and I wrote an article called The Relatively Wealthy Inmate.

Emily O’Brien: He found that, and asked and to come into his office to meet him, because he loved it, and his assistant actually was the one that read my website, and she’s like, “Dave, you’ve got to check this girl out.” She’s the gatekeeper and her name’s Maureen, and she’s just absolutely fantastic. Really good friends now. Then Dave was like, “I’m going to help you.” I’m going to help you, and so we talked every day, and he’s helping me prepare for Dragons Den. He’s the one that actually encouraged me to apply, because I didn’t think I was ready. Because I’ve seen so many people go on that show and just get shredded for being too young, or too fresh, or …

Startup Coach:  That’s half the fun of the show, I think.

Emily O’Brien:   I know. It’s entertainment value, but I don’t want to be entertainment value.

Startup Coach:    No, I work a lot of startups who’ve been very successful on that show, and hopefully you will be as well. You handled the audition. When was the audition?

Emily O’Brien:   The audition was in the end of February. February 23rd. How did that go, and what was that like?

Startup Coach:  Tell the audience what it would be like to go down for the audition process.

Emily O’Brien:     You have to do the online application, and it’s about nine or 10 pages, so you have to have an approximate … you want to talk about your business, your website, your numbers. Just approximate. Then they’re going to call you into present to two producers, and it’s about … they time it to be about seven minutes and then ours went longer, because they kept on asking more questions. We had a scripted thing where we answered the cookie cutter questions that they normally ask on Dragons Den, and then we just let it go from there.

Startup Coach:   Obviously it went well? You passed the audition as it were, and you’re back to be recorded. We don’t know if you’re going to make it on, we understand that. At least you get to present in front of the Dragon, so when’s that happening?

Emily O’Brien:   That is this Friday.

Startup Coach:   And then you’ll be under lock and key not to talk about it after that until the season ends and whatnot, so it’ll be interesting hopefully. After that you can tell us a little bit about that experience as well. Do you have any advice for startups seeking advisers? You found Dave, Dave found you. Advisers are very important. What advice would you have for startups who are seeking advisers?

Emily O’Brien: For me it was using a different method of communication. Also, one of my writing mentors is author Lawrence Hill. He wrote The Book of Negros, he actually lives around the corner from me. For me, it was writing letters, and writing authentic letters about their work and how it impacted my very unique journey. Everyone opens letter mail. If it’s hand written, one thing with letters is that the font is unique, because it’s your writing. And the paper is unique. You can use your own customized envelopes. It’s another way for you to stand out, whereas emails just add up and so even writing and then calling I think, is … write an actual letter and that’s how … I know, I still get letters now from prison, people that have read the article, and love reading them. I think just being unconventional, yet authentic. It’s very important.

Startup Coach: How important is being able to pitch for an entrepreneur?

Emily O’Brien:    Being able to pitch?

Startup Coach:   Yeah.

Emily O’Brien:   Very important. If you want to grow your business. I think presentation skills, and just being honest with yourself and not too confident. Being humble and acknowledging that you don’t know everything all the time. And that you do need help is important, because some people go up there, they’re like, “I’m great at this, I’m great at this, you can trust me.” For me, Dave also said it was great for me to recognize that I needed a partner, that I needed someone who was good at the things that I wasn’t very strong at, so that I could focus on what was strong at. That’s actually a strength is having other people to work with. It’s not a weakness.

Startup Coach:  Absolutely. Entrepreneurship is not a solo sport, so you definitely need a team. What’s your favorite book for entrepreneurs?

Emily O’Brien: I would say right now, This I Know, by Terry O’Reilly, and he actually has a show on CBC. It’s all about marketing, and now also my second favorite one is called This is Marketing by Seth Godin. It’s fantastic.

Startup Coach: Two great books. I’ll have to check out the first one. I’ve checked out the second one. What tools would you recommend that you really think are great or trending right now?

Emily O’Brien: I think a lot of people are really caught up in analytics and the numbers, but for me it’s been nurturing the people that I have. Sending direct messages, using your personal account to send messages to your followers who you already have, and asking them what they want to see.

Startup Coach:   What you’re saying is instead of using a tool, you’re saying nurture your existing network and work that as much as possible and get as much information as you can out of those relationships and building those relationships.

Emily O’Brien:   Yeah, because the most powerful tool is word of mouth.

Startup Coach:  Where can people find out more about you and Cons and Kernels?

Emily O’Brien:   My website is www.cons& My Instagram is @cons&kernels, and my personal Instagram is @territuesday. So I’m actually having a new Instagram. I use IGTV a lot. Before prison life on bail, just all the questions that I got asked, and even just life after prison, because it’s … I feel like this journey is just beginning. The worst is over, and now my parents can finally breathe. Being on parole is still relatively stressful, but not as stressful as the unknown of when is this huge thing going to be done with.

Startup Coach:   Well, thank you for taking the time to be part of Startup Talk Episode 14 Emily, it was great to have you.

Emily O’Brien:    Thanks Craig.

Startup Coach:    And this has been Startup Talk Episode 14. I’m the startup coach. We’ll talk to you next time.

This has been Startup Talk Episode 14, Toronto’s startup podcast. For more exclusive content, the episode vault, and to be part of Toronto’s start community, visit Get your name on the newsletter mailing list, check out our upcoming events. For more episodes, subscribe now. And please recognize the time and work behind the scenes put in to connecting you with the biggest visionaries, entrepreneurs, and innovators in Toronto, by leaving a five-star review. Join us for more next episode, from Toronto’s most active entrepreneur and startup community on StartUp Talk.

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