How to Build An Online Community

{Breaking my hiatus for this topic close to my heart ...}

On Saturday I taught a brand-new Dean Street Seminar on Instagram with Intention.

On Tuesday we kicked off the next round of #StyleMeApril.

I'm currently coaching 40 entrepreneurs through The Mentorship Coterie.

And next month {sneak peek!} I'm bringing back my group style class, Style & Styleability for the first time in 2014. 

These are four of the absolute favorite things I do as a part of Dean Street Society and they all have one thing in common: they're about community.

It's a topic I've been thinking about lately both because it's an part of my success, and so elusive to learn how to create. So when Rachel of The Yogipreneur asked me to be a part of the Heart Your Community Blog Tour and talk about how to build community, it was an easy heckyes to dive into this topic.

So whether you're a fellow entrepreneur or a Dean Street betty who wants a peek behind the scenes, read on!


From the very beginning Dean Street Society has been about community right down to the name. I knew I didn't want my business to be about me, my style, but making the typically exclusive topic of fashion, inclusive, and create an environment where everyone feels welcome and empowered.

I started off  working only with clients one-on-one, which I loved -- both in style and then as I got inquiries, entrepreneurship. Then in both cases I started working with small groups through my Style & Styleability class, and The Mentorship Coterie. Both include a Facebook group and live video calls and suddenly I was creating not just a relationship between me and my clients, but for my clients amongst themselves. I had no idea how much watching their engagement with one another with warm my heart! Now not only is Dean Street Society about learning from me, but being welcomed into a community of supportive peers who "get it", and are with you on taking your lives to the next level, whether through your style or business or both.

While I have Facebook and Google Hangouts to thank for building community amongst my clients, I have Instagram to think for building community amongst my followers at large. Two years ago I started the #StyleMeMarch Instagram Challenge on a whim. I had an idea at brunch, wrote down prompts with a friend and posted it the next day. My followers loved it, when I skip a month they ask me to bring it back, and every month I receive more comments about how powerful this little idea is in their lives, mornings, creativity and confidence all month long.

However, I believe in unabashedly showing the legit behind-the-scenes in my business so I'd like to data-nerdy on you here. Below are the stats for my first month of the challenge, and the recent one two years later:

March 2012: Instagram Followers: 181 // # of Calendar Shares: 5 // # of Photos Posted: 315

March 2014: Instagram Followers: 6K // # of Calendar Shares: 172 // # of Photos Posted: 5,643

My following and # of calendar shares have both grown my 34x, my participation photos posted by 18x. What that means is that when I launched this community {not even realizing that's what I was doing at the time, mind you} it didn't make waves. It wasn't large or fancy. It was small and intimate. Both have their upsides.

Those bettys who participated in the first #StyleMeMarch genuinely developed friendships. There was a small group participating, so they truly got to know one another, with a few becoming pen pals and even meeting up when they travelled to one another's countries -- myself included, as nine months later I met #StyleMe betty, Anna, who'd become a dear friend, in person when I lived in London for a spell.

I believe it was their relationships, their foundation of encouraging words, that set the tone for this to grow into a large community that nonetheless has maintained the "kindest tribe on the interwebs" reputation that's my ultimate goal. You can read our Dean St Community Credo here for more on why we're a "negativity free zone".

And now as we're growing, community begets community and it's of course become a blessing in bringing me new traffic, clients and revenue for my business.

In closing, I think community is a large part of what makes Dean Street Society special. It was both an intentional priority from the beginning, and also a serendipity I stumbled upon along the way.

Community is primarily free. Instagram, Facebook, Google Hangouts -- all the platforms I use are free, and those elements of my business, even for the paid products, are more of a bonus with the true cake being my teaching and the community being the extra frosting. Yet somehow that frosting is also our core, our backbone.


So if you too are on the journey of entrepreneurship my advice for you would be thus:

1) Know the type of community you want to create and lead by example. Start early and always keep your vision on the kinds of people you want to be surrounded by. Like attracts like.

2) Add community elements wherever possible. Test out new forms of conversation and engagement. I didn't know what gems I was starting when I tried any of the above, but I played around and made wonderful discoveries.

3) Be patient. Review my #StyleMe analytics above. Community takes time. You're growing something and that can't be rushed. Think of where you want to be in three years, not three months.

4) Use your words. I post my Community Credo, I have guidelines for how we interact inside the Style & Styleability Treehouse of Trust {even the name indicates my heart} and each month I post #StyleMe I remind people that we're here to encourage, not critique. While I acknowledge I can't be entirely in control, I intentionally articulate whenever possible to let bettys new and old know what this tribe is all about.


The world can never have too much community, goodness, empathy, friendship and conversation. Thanks in advance for adding to that. {wink}

P.S. Remember that you are welcome to join in this community, m'dear! Hop on Honor Society where you'll get the news of all the newest offerings. Plus, I've got two one-hour Dean St Seminars as my FREE gift to make you feel welcome. Join us inside now!

P.P.S. And speaking of community, check out what all the other Heart Your Blog Tour gals have to say about this topic including Anna of Curvy Yoga yesterday and Amy of The Path to Bliss tomorrow!

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Alt Summit 2014 Encore

Last week I was blessed to be able to speak at Alt Summit, one of my all-time favorite conferences, with one of my all-time favorite fellow entrepreneurs as my co-teacher. Whitney English and I spoke on "Overcoming Overwhelm" and I'm thrilled to say that throughout the conference bettys approached us to let us know how much value they got from the time.

Since we know so many of our readers couldn't swing it to join us live, and this content is so close to our hearts, we decided to teach this class one more time, FREE.

Click here to enter your name and email to join us this Thursday!


We only have 100 seats available to join us live so arrive a few minutes early!

Even if you can't join us live? Register with your name and email here, and a recording will be sent!

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One New Season on Dean St, Two New Choices for You!

Love, I've got a question that I would love for you to answer:

Do you come to Dean Street Society for style? Or do you come for business inspiration?

Are you more passionate about dressing in a way that makes you feel radiant? Or building a business that makes you feel radiant?

Or both?

Some Dean Street bettys have come across my style blog, desiring a more educated style, and think, "Why the heck is Hilary talking about her business? Why is her first book about entrepreneurship and not style?"

Many others have crossed my path because you're fellow entrepreneurs and bloggers who don't just want to pick my brain about style, but about small business, branding and blogging wondering, "Gah, why is the weekly blog post only ever about style? Why can't she share more about how to build a business like hers?

Whichever camp you're in, watch this video I made for Honor Society to hear how I'm restructuring to serve you more. You're invited to choose your own adventure. Telegrams or cocktails or both? 


Ready for the next choose your own adventure? You're the first to hear the title of my new book... {insert drumroll} ...

 The 4-Part Entrepreneur Cocktail!

Why is it a choose your own adventure format? What are the four parts of the cocktail? How can you join me for Camp Cocktail in January? 

All those gems plus extra teaching from me that you can get access to weeks before the December 17th launch, will be happening in Sunday Happy Hours so join us now!


Whether it's 2-Part Fashion Cocktails or 4-Part Entrepreneur Cocktails that you're passionate about, I want you to be a part of Honor Society so I can help you most.

Can't wait to see how much brighter you can shine, in style and/or in business, this fall and beyond ...


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P.S. Did you just skip right to the end? No worries, sometimes I'm in a rush too!

1) If you love Dean St for style. You want to be on the Thursday Telegram list to hear about style offerings, style classes, style blog posts.

2) If you love Dean St as a fellow entrepreneur or blogger, join Sunday Happy Hour! You'll get the news on Mentorship Coterie, Dean St Seminars on business, and my NEW BOOK that's just for you.

3) Love both? Join Sunday Happy Hour AND the Thursday Telegram! Neither will happen every week so I won't be overwhelming your inbox, and you can be sure to never miss a blog post, new offering or inside scoop. 

Hear more in the video. So excited to help you more and serve you better, love ...

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Marie Forleo's B-School

Yesterday one of the mentors I admired most in this entrepreneurial world, Marie Forleo, interviewed me as one of her "success stories" as an alumni of her B-School program. It was surreal. And a day I will never forget.


Marie's course will happen again in March {I'll be coaching a group through it via The Mentorship Coterie so hop on Honor Society if you want to hear more about that} and in the February roll-out you'll be able to hear how her program has changed my life.

Which got me thinking about the stories of those who I can humbly say have been changed be the programs I teach here on Dean St. Style & Styleability starts on Saturday, October 19th and I want you to hear what one of my students, Cecelia, wrote to me after our summer session:  


I have never, ever felt like I "got" how to dress myself stylishly, and I never understood how people could pull together outfits and looks easily. No matter how many fashion magazines I read or outfits I bought, I could never find clothing that worked for me. Inevitably, I would get frustrated, and simply wear whatever was most comfortable (sneakers and old jeans, mostly). I always assumed that I needed to spend more money, or be more prettier, or lose 30 pounds before I would ever look pulled together and attractive. HA!
Your course not only changed my mind, but it gave me confidence I didn't know I had. Somehow, your super-savvy style tricks changed the way I viewed outfits and clothing. I could suddenly SEE how proportions, texture, colour and pattern worked in new ways. Every day I made an effort to wear a fun outfit for different events (summer BarBQs, work meetings, dinner parties) and I couldn't believe the compliments I got. (And yes, I didn't lose a pound, get a facelift or dye my hair). 

Even shopping for clothing was something I hated, and found so stressful. But the course gave me such a boost of confidence that I was able to sail into a little boutique near my home (that I'd never gone into before), and happily select items to try on. I was really amazed to see that I knew exactly what to look for, and I could even estimate size pretty accurately and easily. I tried on several, and I was thrilled to find two dresses that were absolutely stunning. 

Since taking the course, I've re-organized my closet by colours (which makes my eyes sing happily every day - I had no idea I loved colour so much), and I've now got my "go to" outfits and accessories carefully laid out (even in the midst of a cross-country move). The simple act of dressing myself is now a pleasure, and I really notice that I take so much more care than I ever did previously, even when I select my earrings and necklaces. This level of self-care just makes me happy, which is so essential in a stress-filled world. 

Most importantly, I feel like I can walk into a room now for any occasion and OWN IT happily. I'm definitely not young, model-ish or skinny, but I know now that I can feel as polished and gorgeous on the outside as I know I am on the inside. 


Have you ever felt like Cecilia? Frustrated, exhausted, convinced that 10 less pounds or $1,000 more dollars would make the difference?

Are you ready to stop wishing you could feel stylish, professional and confident and starting BEING that? 

Love, we are going to make so much happen in just one hour a week, for one month. Read all about it here and join us!


I'm not sure which gets me weepy more quickly -- feeling overwhelmed that my life has changed so much in two years I'm my mentor's "success story" or seeing how much my students lives change in just one month of Style & Styleability

Either way, I'm feeling grateful for what capacity we have to grow, how we can help one another make it happen, and celebrate together along the way. Thank you for making my "success story" possible. I only hope I can repay you by helping you create your own "style success story" this fall ... {Make that happen right here!}


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P.S. As one more thank you, I'm hosting a style chat on Friday, October 18th at 1pm EST with a free look inside Style & Styleability!

Hop on the call with me from your phone or computer, ask me your style Qs, listen with your headphones in at work, pour a cup of tea and just enjoy the energy of being live with the Dean St bettys. One of the common threads in your emails to me is feeling like you're the only one who struggles with these style challenges, insecurities, confusions. Spend an hour with us and I promise you'll realize that you are not alone and closer than you think to genuine confidence and an authentic joy at being more beautiful than you ever realized you could feel.

Save your seat here now! Oh and it's totally FREE. Can't wait to see your name on the line ...


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Dean Street is Seeking Fall Interns!

The Dean St Betty Coterie {what I call my team} is growing and we would love to have you on board!  We're looking for a whooping FIVE interns to bring on for a short October-December assignment. Read on for more and apply!




Location: Anywhere

Compensation: Unpaid internship with potential for paid position in 2014

Hours/Expectations: 5-10 hours per week {flexible}

Duration: October-December


PR INTERN to assist in marketing my first book launching on December 17th. Reaching out to a variety of mediums for interviews and posts, as well as coordinating a blogger outreach effort and helping with a social media push. Strong written and verbal skills, as well as ability to match tone of the brand required.

GRAPHIC DESIGN INTERN to assist our talented graphic designer, Ana, in a continued website rebrand and creating materials for our first book launching December 17th. Illustrator and Photoshop experience required.

LETTERING INTERN to assist our graphic designer with the hand-lettering that appears throughout our brand. This position will have a very limited time commitment, yet is an integral part of our aesthetic. A great portfolio builder and exposure to our audience. <-- NEWLY ADDED POSITION!!

WEB DESIGN + TECH GURU/GODDESS INTERN to assist our web designer in a continued website rebrand and creating materials for our first book launching December 17th, as well as ongoing new technical additions. Squarespace 6 experience strongly preferred.

CHIEF OF STAFF INTERN to assist my incomparable VA, Nicole, in running the day-to-day business operations for a fast growing and expanding company. High level of trust and professionalism required.



Please send an email with the title of the position you're applying for (i.e. PR Intern) to answering these three questions. 1) What is your background and experience in this area? 2) Why do you desire to be a part of the Dean Street Society team in this capacity? 3) What are your other time commitments this fall and what are the days/hours you will be available? 

Please Include: Links to your website, blog, social media profiles so we can get to know you!

Application Deadline: ASAP, positions will be filled as soon as an ideal candidate is found!


Cannot wait to get to know you better and hear your story! 

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