marketing connoissuer

S1E5: Behind the Scenes of a Marketing Connoisseur’s Business

In this episode of the Candid Conversations small business podcast, your co-hosts Dan and Sagan interview Charmaine Jennings of Strategic Charm Boutique. Charmaine shares what it’s like behind the scenes of running a solopreneur marketing connoisseur & copywriting company, how she went about starting her own business, the lessons she’s learned, and how she’s grown her business in the first year.

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Show Notes Want to start a solopreneur business? Get solopreneur business tips & find out what life is like for this marketing connoisseur after her first year as a small business owner! Click on over to listen to the small business podcast episode now

0:00 Introduction to the podcast

00:40 Update on our business

Get an in-depth update on our business, Juxta Communications, by clicking here.

1:20 Introduction to Charmaine Jennings, Strategic Charm Boutique

2:00 Why Charmaine decided to get into the marketing industry

3:35 Why Charmaine decided to start her own business

“For me, being an entrepreneur is all I ever wanted to be. So even as a kid, I knew I wanted to run my own business. I just liked the idea of being my own boss, having my own rules, doing whatever I wanted (which I realized is not how it actually works). But even as a kid, my earliest memory of entrepreneurship was when I was running a mini talent agency in grade 3! I’d sell tickets and market the event; it’s always been on my mind to be an entrepreneur.” – Charmaine

5:00 What does a typical day look like for you?

“The very first thing I have to do is clear my inbox; I can’t start my day unless it’s cleared.” – Charmaine

6:10 On organizing email inboxes

“It’s interesting how, in some areas of your life, you can end up being so meticulous and such a perfectionist, and then in other areas, just not at all! Especially when you own your own business” – Sagan

7:10 Some of the biggest lessons Charmaine has learned from starting her own business over the past year.

“One of the best pieces of advice that really stuck with me was from Devan Danielle, a business coach in the States, and she said, ‘don’t wait until you’re ready to start your business; just go ahead and do it, and you can learn as you go.’ A lot of people are waiting until they get more knowledge or more contacts or more inspiration, but I feel, when she said that, that you can just jump in and work through it as you go, that kind of struck a chord in me and the next week I was planning out how I’d launch my business.” – Charmaine

“There’s never going to be a perfect time to do anything in life, so if it’s something you really want, then why not do it.” – Sagan

8:40 How Charmaine transitioned out of her 9 to 5 job and into working from home full-time.

“I thought, I’m working days, I’m working evenings, I’m working weekends, so how am I going to find time to work on my business? But somehow I made it work.” – Charmaine

11:25 How Canadian businesses can get support from the government for starting their own business Thinking about starting your own business and becoming a marketing connoisseur? Get the inside scoop on how this solopreneur started her business, the lessons she learned along the way, and more -- click on over to get the goods!

12:50 Shopify ad:

13:50 What challenges do you face as a solopreneur?

“Trying to find the balance between doing client work and taking the time to take care of my own business has probably been the biggest challenge for me. Also, trying to organize my finances is a challenge! I’m trying to be more mindful of that when I make income; it didn’t occur to me to save money to reinvest in my business or pay bills in the beginning! I’m working on it.” – Charmaine

15:10 What do you enjoy the most about your work?

“One of the things I enjoy most is that I can do pretty much whatever I want with my business. I can add services as I like, I can add online products as I want, I can launch new initiatives, I can take away things that I thought I’d like and decide I no longer like. Just having that freedom to mold it into whatever I want it to be, I think is the most fun! Also working with my clients — I’ve been lucky; most of my clients so far have been amazing.” – Charmaine

16:05 What type of clients do you work with?

18:00 The challenges that come with working with clients who live on different continents

19:00 What kind of advice or helpful tips can you give our listeners?

“If you’re flirting with the idea of starting a new business or launching a new product or service, the best way to see if it’s going to work is to just get out there and do it. Not every idea you have is going to be golden! Just go out and test the waters. Utilize all the free resources that are out there. Dive in, learn what you can along the way, and that’ll get you to where you want to be eventually.” – Charmaine

20:10 About the Hustle & Charm Community

“Hustle & Charm is primarily for female Winnipeg bloggers and business owners who feel alone in your business. Being an entrepreneur is hard; not a lot of people understand what we go through with having your own business. I wanted to create a space where us women can meet on a regular basis face to face and share ideas, expertise, concerns, and resources.” – Charmaine

“I love this idea of connecting with other Winnipeggers, because so often it feels like as bloggers and small business owners, we are just sort of alone in Winnipeg and there’s no one else who does what we do, but that’s not true! There’s a whole bunch of us.” – Sagan

23:50 Why we decided to start a Winnipeg-focused business podcast Solopreneurship isn't easy, but when you know the tips & tricks of the trade, YOU can be a successful solopreneur, too! Get solopreneur tips in this small business podcast episode featuring Charmaine of Strategic Charm Boutique -- click on over to listen now

“There is no other podcast really talking about other Winnipeg businesses; a lot of business podcasts are American-based.” – Dan

24:55 On finances and bringing on additional team members

26:00 Next plans for Charmaine’s business

“By the end of the year, I want to start a lifestyle blog…  All my ideas seem to be big ideas, and I want to do them all at the same time!” – Charmaine

27:30 On entrepreneurs taking on big projects and implementing new ideas

“You can learn so much from trying things out and seeing how they go. What I found was, when I launched my Twitter chat, my biggest problem was sticking to a weekly specific day and time — I didn’t like knowing that I was forced to do something on a specific day and time. So I realized that from there, I needed to start my own Facebook group instead. So you can test things out, see how you like them, and put it on the backburner or scrap it if it’s not the right fit.” – Sagan

30:30 How to learn more about Charmaine

Visit Charmaine at and @StrategicCharmBoutique on Instagram

30:55 About shadowbanning on Instagram

32:55 Thanks for listening!

If you enjoyed this podcast episode, give it a like and a share. It would mean a lot!

33:25 Outtake 🙂

Awesome Resources + People Mentioned In This Episode:

Don’t Be a Stranger!

Hang out with us! We’d love to chat with you.

For example, you could…

  1. Tweet at us (@JuxtaComms) to let us know what you thought about this podcast
  2. Email us ( with any small business questions you’d love for us to answer
  3. Review this episode on iTunes and share it with your friends so that even MORE people can benefit from the amazing guests we feature!

Pssst… want to grab Dan and Sagan for an interview on YOUR podcast or blog? We’d be honoured! Shoot us an email and let’s chat.

Find out what Charmaine’s up to now in our book, A Year in the Life of Candid Conversations: Behind the Scenes of Creating a Podcast From Scratch.

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