Raise The Anchor
Raise the Anchor- is a transformative podcast hosted by Melissa Burbridge, where ordinary people share extraordinary stories of life-changing moments.
From overcoming health challenges like a life-saving liver transplant to bold decisions like a career pivot or adopting a life-altering diet, each episode dives into the pivotal moments that reshaped lives for the better. Through Melissa's thoughtful interviews and powerful narratives, "Raise the Anchor" inspires listeners to let go of what holds them back and set sail toward a brighter future.
Join Melissa each week for stories that will spark inspiration, ignite courage, and remind you that it’s never too late to rewrite your story.
Raise The Anchor
Cookies, Keys & Global Dreams: Jenna Ross Is Back!
Jenna Ross, serial entrepreneur and founder of the Nova Scotian Cookie Company, shares her journey from IT professional to managing three thriving businesses while raising teenagers and maintaining work-life balance.
• Nova Scotian Cookie Company began after a human design reading gave Jenna "permission" to be a serial entrepreneur
• Lighthouse-shaped shortbread cookies represent Nova Scotia and have taken Jenna to LA, Italy, Germany and beyond
• Attended the Golden Globes and Emmys gifting suite in Los Angeles where her cookies were gifted to nominees
• Connected indigenous designer Tracy Metallic with Cheekbone Beauty's Jen Harper for Halifax Fashion Week
• Models walked the runway wearing Nova Scotian Cookie Company aprons during fashion week
• Built strong teams across all businesses to handle day-to-day operations while she focuses on vision
• Manages property management company, real estate investments, and cookie company simultaneously
• Emphasizes the importance of "just getting started" rather than waiting for perfect conditions
• Learning to trust the universe rather than forcing outcomes
• Developing a new podcast focused on entrepreneurial mindset and balancing business with life
Follow Jenna on LinkedIn or on Instagram @happyplacepropertymanagement and @nscookieco to stay connected with her entrepreneurial journey.
Welcome to Raise the Anchor, the podcast that explores what happens when we stop drifting and start choosing. I'm your host, melissa Burbridge, and each week we dive into real, raw stories of transformation moments when people dared to raise the anchor and change course. Whether you're navigating chronic illness, burnout, big life pivots or healing from the inside out, you'll find inspiration and truth here on Raise the Anchor. This is your space for honesty, hope and the courage to begin again. Let's raise the anchor and set your course. This episode is sponsored by Capture Photography headshots for people who hate having their photos taken Highly recommend.
Speaker 1:Today on the show, we have brought back Jenna Ross, one of my biggest inspiring women. I so love having her back. She went from having an IT business to property management. She's grown a property management, has children, has a real estate investing business and you have a new venture which I can't wait to share with our guests on there. I have no idea how you do it. Welcome to the show. Thanks, melissa. So your new venture is completely different than property management. Can you let us in on that new venture?
Speaker 2:Yeah, so what you're speaking of it would be the Nova Scotian Cookie Company, and so it's an idea that came to me on October 15th of 2021. During the pandemic, I had my human design chart read and it gave me permission to be an entrepreneur. I realized I'm a serial entrepreneur and that there's a cookie company that was trying to get outside of me. So, immediately after my human design session with Don, I decided to start the cookie company.
Speaker 1:That's like, that's amazing, and it's so different. The real estate investing goes along with the property management. It's almost like hand in hand. Yes, so three businesses. Yeah, your husband works a lot as a real estate person and you have two very busy children and two dogs and two dogs. How do you do it? So what inspired you to want to get into the cookie Like? I know? You did your human design, but why cookies? I know.
Speaker 2:So it was. I was talking to the business partner that I started the cookie company with originally and we were looking at multiple ideas and we had some ideas for starting a real estate investing company together. That's what we both knew, that's how we met and that just seemed easy and it just seemed like we were forcing it and trying to buy a property just to to get that started. But we had also talked about a lot of different ideas and the one that really resonated with me was the cookie company which is modeled loosely after the Honolulu cookie company in Hawaii, so pineapple-shaped shortbread and you know. So it's modeled loosely after that because really, with the branding and everything, took it and made it its own unique thing. So sharing the love of Nova Scotia with the world is where it ended up going.
Speaker 1:And I love the shape. It's a lighthouse, yeah, which is perfectly fitting for Nova Scotia, with Peggy's Cove and some of our other famous lighthouses yeah, which is beautiful, and it has opened up so many doors for you. You have gone to LA, you've gone to Italy, you've just done so many amazing things with this cookie company. Can you walk us through that?
Speaker 2:Yeah. So I didn't know originally that it was going to take me traveling the world, but I kind of used it in that way to reach out to people around the world and share the love of Nova Scotia with the world, because I'm passionate about Nova Scotia, nova Scotia business, social enterprise. I had a contact in Bangkok, thailand, and he does work with CanCham, so we sent the cookies over to the Air Canada inaugural flight Christmas party there, and so Derek, my contact, helped me get the cookies there and that was an adventure in its own and super fun. And then from there was just, you know, opportunities. I was saying yes to opportunities that lit me up and so and it just kind of snowballed and the, the venture in LA that was like, so unique and amazing thank you.
Speaker 2:yeah, that was super fun. Yeah, so our cookies. I traveled with the family, the whole family came on that trip and we went to Los Angeles at the Lux Hotel and so got to give cookies away to nominees of the Emmys and the Golden Globes at the DPA Golden pre Golden Globe gifting suite.
Speaker 1:And I'm sure that was never on your bingo card Like one day I want to go to the Golden. Globes and Emmys to give them cookies, right yeah.
Speaker 2:And, and the interesting thing about that was that the actor-writer strike was happening and originally what I had signed up for which seemed pretty, you know, achievable was the TIFF, toronto International Film Festival. So that's where I was supposed to go, but because of the you know the situation they quickly pulled out of there for that year and and offered me the spot at the Golden Globes gifting suite.
Speaker 1:Toronto LA. I think that was a no brainer.
Speaker 2:Yeah, it was. It was incredible and I just I thought, wow, this is really, this is really exciting. I mean, obviously, when you hear an opportunity like that, you get your butterflies in your stomach, it lights you up. That's easy to say yes to and figure out the details afterwards.
Speaker 1:And I love that you listen to what lights you up With the human design. We've talked about it on a few of these episodes right now, and certain people have to listen to what lights them up listen to their gut listen to their head. Different things like that, so I love that piece. You've had a fashion show like where. So you went from IT to property management to doing your cookies that have taken you into a hosting a fashion show tell us about that.
Speaker 2:Yeah, so the I like connecting people, so that's one big theme through all of my life and businesses and my corporate IT career that I came from and IT was never meant for me.
Speaker 1:Um, I can't see you behind a computer all day. Well, you are, but in a different capacity.
Speaker 2:Yes, and I joke that the thing that I got through IT is my career and everything is that I met my best friend and she's like family to me, Catherine Ann. So that had its purpose. And then, yeah, when my girls were born, I needed to get out and, um, get out of the corporate world. It just wasn't working, um, with our youngest being sick, and so I did that. So it's been nine years that I've been fully self-employed, self-sufficient, on my own. What I I eat, what I kill kind of situation I love it, yeah and yeah.
Speaker 2:So you were asking about the fashion show. So Halifax Fashion Week and that was really interesting too, because I always loved fashion. I did for fun, just fashion shows in my high school. I did a for fun fashion show at University in Texas my first year. So I'm interested in fashion and the connection came because my osteopath I was still seeking recovery from my accident that I had, but my osteopath turns out that he's a fashion photographer.
Speaker 2:So when I went to, when I was getting ready to go to Germany and we went to Paris and things like that, he he happened to say, did you, did you, are you going to Paris fashion week? Because it's around that same time. And then we got talking and then I realized, oh, he's got friends that have fashion lines and things. And then when I went to Los Angeles, it was really interesting because I met Connections who I was able to introduce to him Blair and I was able to make connections for him and then some of the models ended up getting photos that he had submitted to a magazine in Los Angeles from the Connection and just really interesting connections. And then I met when I was in Los Angeles I met Tracy Metallic, who's an indigenous designer, and I connected her to Halifax Fashion Week, to Halifax Fashion Week and I said to Tracy, wouldn't it be interesting if Jen Harper from Cheekbone Beauty, she spoke at the Halifax Chamber, wonder Woman, is it Wonder Woman? Yeah, the Wonder Woman conference it was. I wanted to say Superwoman.
Speaker 1:Well, there are so many superwomen there are, yeah.
Speaker 2:So I saw her spoken, speak there, and I was just blown away and I said to Tracy do you know Jen Harper, um, who's an indigenous um owner, business owner of Cheekbone Beauty. And she's like, well, we might have mutual connections and I was like, how cool would it be if the models wearing your indigenous clothing brand wore Jen Harper's makeup? What would you think about that? And she was like, well, that would be cool. So I didn't know Jen Harper like, but I reached out to her and, um, I made that connection. Of course, I sent her cookies and the Indigenous Women in Business book that we sponsored and a little care package.
Speaker 2:And then we had a call, blair and Sully and Tracy and Jen, and right away Jen Harper was like yeah, I want to sponsor Halifax Fashion Week with makeup. Her grandmother is from Cape Breton, so she has a connection to here. And so that happened and a few more connections. And then the next thing, you know, soli and Blair said you know, we're so thrilled and we're partnered together, so the cookie company was sponsoring Halifax Fashion Week. And then somehow, the next thing you know, they ended up walking on the runway the models wearing Jen's makeup, cheekbone Beauty and wearing Cookie Company aprons, I know, and carrying suitcases, right, so yeah that was very maritime and unique and it was not expected.
Speaker 2:But it fit, it fit. Yeah, and I got to um, I got to sort of engage with a lot of the models and and they were selling um, they were using some of the cookie product and so I got to engage with them because they were doing some fundraising, so got to know everybody and it was it was really cool.
Speaker 1:Yeah, and you've gone to Germany for a trade show yes and from that fashion show you've also gone over to Italy and done some pretty cool things there. Like it's taking you everywhere yeah, and I mean it.
Speaker 2:I think when the Mastermind Roundtable, mastermind experience to Italy came up, it wasn't related but I was like, ok, like it was Lori and Chris Harder and I've been following both their podcasts for many years. One of the first podcasts I listened to was Lori's, because she has the earn your happy podcast and I've been following her for a number of years. And, um, when the opportunity came up for that um experience, it was again like a hell, yes, I want to go. And then there was the element of having dinner with the Ferragamo's family James Ferragamo and his wife and I thought, ok, it can't be a coincidence that there's fashion here and I don't know, and solely management and the models um were going to Milan, blair was going for Vogue and and they were doing a fashion show. So I was like I need to go for them as well as myself, like it was in Italy.
Speaker 1:How is that yeah?
Speaker 2:So I was sort of on a mission to try to get some connections made there.
Speaker 1:And the gown and the photos, like they're amazing.
Speaker 2:Yes, and the gown that I wore was Cush Massage. So Blair connected me to Cush and, yeah, she's got incredible designs. It was so fun. I felt like a princess um the opulence of that trip and the experiences where it was a trip of a lifetime yeah, it looks like it definitely yeah, screamed off your.
Speaker 1:Instagram stories and I'm sure your Instagram stories are only a snapshot of the whole adventure.
Speaker 2:Yeah, and you got to take Greg with you, which is amazing.
Speaker 1:Yes, and you've gotten to take your girls on some of these amazing trips too, yes, which is so inspirational and I'm sure they look at you and are like, wow, this is awesome, yeah. So you have a pretty decent support system because you run three businesses.
Speaker 2:Yeah.
Speaker 1:So what does that look like day to day? Are you like fully dipped into each business? Are you a step back? Because I know when I worked at Happy Place you were very much invested and you were trying to take a step back and let the business be self-run. Yeah, what does everything look like now?
Speaker 2:So, now, like things are different. I managed, you know, kind of out of necessity, to build a team and remove myself from the day-to-day stuff. It's hard to give up a lot of the tasks it is. It is hard to give up a lot of the tasks it is. It is hard, yeah, because when I started the business it was just me and I did absolutely everything.
Speaker 1:Even digging in the sewer.
Speaker 2:Everything yeah, like dirty things, yeah, just everything you can possibly imagine sales, marketing and administration, and so now the team handles most of the day-to-day stuff. So I'm really able to be the chief visionary officer that I call myself, managing the vision and also supporting the team. So I'll have calls with Vicki, who's the manager now.
Speaker 1:Amazing person.
Speaker 2:I know and so I'll have calls with her when there's things going on and yeah, and then team you know we have a weekly team meeting and go through, you know, and following along making sure everybody has what they need and as we're busy right now, that's really important to make sure that people's workload is manageable and that we are managing the stress that can sometimes, you know, helping them and looking when things are stressful to try to remove some of that and spread it across the team so that we're yeah.
Speaker 1:And what's it like with the cookie company and the real estate investing, because you also hold monthly meetups with your investors, so that's kind of crazy.
Speaker 2:Yeah, we've switched the meetups to bi-monthly but we still really enjoy that educating people and just educating our investors as things shift because the market has shifted a lot in the last five years and the real estate investing side it's been a little bit less Like. We just sort of are managing the portfolio that we've acquired. It's not huge, it's just an investment for the future. Greg and I have added a fourplex. We bought our partners out and you probably aren't even aware, but we ended up buying sort of like a cottage in Wentworth with a couple other families for skiing and yeah, so it's a, it's a rental and we've gotten the chance to enjoy it as well, but it's been a big renovation project for the last basically 12 months renovation project for the last basically 12 months.
Speaker 1:That must help in ski season, Cause I I know we've gone skiing or had our daughters go skiing together and it's a process, and then you're there for the day and then you're kind of tired by the time you want to go home. So now you can go back to the cottage.
Speaker 2:Yeah, it's a minute drive from the ski hill at Wentworth. So so that's been, that's been fun and it's been, you know, a little project to get our hands dirty and pick away at that and get it ready and um. So that's been, that's been nice, and we share it with um two other families, so we've been able to share the big project and um, and it's finally completed and and we have people renting it right now.
Speaker 1:So yeah, nice, and you have help with the cookie company.
Speaker 2:And help with the cookie company. Yeah, so I have. I have Donna. A lot of people who are aware of the cookie company will know Donna. She's everywhere and from day one when I told her about the idea, she was so excited. Businesses that I have, um, I have staff, um, who are like business owner mindset, that they really, um, they're passionate about what they do and um and enjoy it. So that's been, that's been huge.
Speaker 1:Yeah, yeah, no, I love that because you have so many things and you're so passionate and involved. It's nice that you have a team that can support that piece so you don't burn out. Yes, that you can be present with the girls because they're growing yes, they're older. One's in high school, yes, and the other one's in middle school, yeah, so that's like big changes 13 and 15.
Speaker 2:So two teenagers, isn't? It lovely Two teenagers.
Speaker 1:Yeah.
Speaker 2:And it's yeah, and you're, and I know you know like, uh, when you have teenagers, um, they're trying to get their independence, but they also need you more than ever. So it's like it's, it's fun need you more than ever.
Speaker 1:So it's like it's it's fun, it's precious, but it's also scary, very scary. We won't touch on that because I will cry again. If you could speak back to yourself before all of these businesses, before you left IT, or even just even with the property management, what would you say to yourself?
Speaker 2:I'm thinking back to when I graduated from university and I had a huge debt load and I was having a hard time finding full-time employment and I would tell myself it's all going to be okay, because financial stress can be so huge, and I guess part of me wishes that I knew that you can take the time and do what you want to do, because I went into IT and it was out of necessity for needing employment, but anyway, I mean, life has. I think I would tell myself that everything's going to work out.
Speaker 1:What unexpected lessons have come from your experience, good or bad?
Speaker 2:The lessons would be that when so when I already had a business, it was like, do I really need to start the cookie company? But there was a part of me that really needed to know and I think the lessons are that you know, just get started. That you know, just get started. Like life is too short to have any kind of regrets around something that you wanted to try, that you didn't try.
Speaker 1:No, I love that. One of our previous guests said even just dipping a toe in is a step forward. So how do you stay anchored now, even as you keep moving forward? You have multiple businesses, kids, a busy life. How do you stay anchored into your now and present?
Speaker 2:Yeah, I think I've sort of gone through a year of transformation with I have a business coach and she's very spiritual and she's been giving me a lot of guidance and so that's been keeping me grounded and like realizing that I don't need to force anything because I always want to make something happen, because I always want to make something happen, but to just kind of trust the universe and let things unfold as they will.
Speaker 1:Love that. What does a brighter future look like for you today, and how is it different from what you imagined?
Speaker 2:Yeah. So I think for me it's a lot about legacy and in that I'm like learning a lot about legacy being what you do right now like and it is. It does come down to being present with your kids, enjoying the journey, enjoying the businesses that I started. There's always going to be good and bad parts about it, Difficult parts, challenging seasons, but just enjoying the journey.
Speaker 1:I like that. Yeah, you also do a lot of public speaking more and more and I know you were very scared to get into it. I remember going to Corey's class about public speaking before and you were nervous to do it. Now I see your public speaking everywhere Every time I look at your socials. You're speaking somewhere. I love it for you. And how is that? What was that journey?
Speaker 2:So the journey has been interesting. So, yeah, I did take Corey's, I took a course with Corey, did some work with Corey and ended up going and speaking at Harvard and that was awesome. Greg and the girls came for that one. And I also took a public speaking course with Mark Black, who I went to high school with in Moncton and that, you know, kind of exposed me even more to kind of learn about the business of public speaking, and so I've been focusing a lot of my thoughts and energy around what do I want to speak about? And what I do want to speak about I've sort of discovered because I'll be launching a podcast and working on a podcast around it is the entrepreneur mindset and that's, you know, having having multiple businesses or even one and managing a life and kind of the full package of what that looks like.
Speaker 2:So, yeah, public speaking is interesting. It's something that I'm interested in and I will be doing more of in and I will be doing more of, and it's, for me at this point is more of a sort of something that I'm working on, dabbling in and trying, you know, trying to do more of it because I remember my mom saying she had a quote written down. A writer writes in her home because she wanted to write, and it's kind of like that a speaker speaks. So if you you know I had it on my LinkedIn for a long time that I'm a speaker, so you have to, you want to do the speaking. I don't want to just say it.
Speaker 1:Yeah, exactly, I absolutely love that you're getting back into the podcast world. Yes, because your old podcast. I listened to every episode. Yes, I had to, but I love it because you're such a good speaker. So I love to hear that you're getting back into that world with another season, but I'm going to do something completely different, to kind of marry the two different businesses that I have.
Speaker 1:I love that so much because I do think if you went back to the happy place, which I loved, that would pigeonhole you into the real estate investing. Yeah, yeah, yeah. So where can the Anchor Crew follow up or connect with you?
Speaker 2:So on LinkedIn you can find me, jenna Ross, you can follow my socials. So Happy Place Property Management on Instagram and Facebook and the Nova Scotian Cookie Company, ns Cookie Co, on Facebook and Instagram as well.
Speaker 1:Awesome. So who or what inspires you? I know you hate this question.
Speaker 2:I get inspiration from a lot of different people. Honestly, Like it's a lot of. I listen to a lot of podcasts. I would say that's where I get a lot of my inspiration and ideas from.
Speaker 1:Yeah, I love that you hadn't answered this time Last time.
Speaker 2:It took a little while.
Speaker 1:But I like that you have the time. Well, it's been an absolute pleasure catching up with you, thank, you, thank you.
Speaker 2:Thanks so much, melissa.
Speaker 1:Thanks for tuning in to Raise the Anchor. If today's episode spoke to you, share it with a friend or leave a review. It helps more people find their way to healing and hope. Follow along on Instagram, tiktok or YouTube for behind the scenes, extra content and real life moments, and be sure to join the email list at linktree slash. Raise the anchor so you never miss an episode until next time. Here's to calm waters, steady winds and the courage to chart your own course.
