10 Questions with Cyndie Spiegel, founder of The Collective of Us

This is the tenth post in a weekly series called “10 Questions with” that will feature creative entrepreneur profiles and small business owners who have incredible stories and advice to share. It’s the perfect series to follow for budding entrepreneurs and creative people who want to know more about other people’s creative processes. Check back here every Wednesday to see who will be profiled next.. The interview is below the images.

10 Questions with Cyndie Spiegel, creative entrepreneur profiles | Read more at blog.cuteheads.com

10 Questions with Cyndie Spiegel, creative entrepreneur profiles | Read more at blog.cuteheads.com

10 Questions with Cyndie Spiegel, creative entrepreneur profiles | Read more at blog.cuteheads.com

I recently wrote a post about some of the things I learned in 2015 as a small business owner. What I didn’t mention in that post is that a lot of what I learned was a direct result of my joining a pretty incredible group of women, spearheaded and led by creative entrepreneur and business coach Cyndie Spiegel. She’s the founder of The Collective of Us, an insanely awesome group of entrepreneurial ladies who get together in small groups via Skype once every 2 weeks to discuss goals, challenges, and how to help each other grow.

There are TONS of business coaches out there, some legit, some not. But anytime people ask me what the biggest changes have been in my business, I always give credit to The Collective of Us and Cyndie for being two of the biggest change agents for me last year. Cyndie is honest, straightforward, no BS, but incredibly supportive and passionate about helping others become successful. That’s why it was totally fitting that she be the first feature of 2016 in this series. As each of us begins anew with a fresh start, I thought it would be helpful to hear from someone who has inspired so many.

Glad to chat with you! First, tell us where we can find you online.

Cyndie Spiegel, Cyndie Spiegel Inc.: cyndiespiegel.com

The Collective of Us: thecollectiveofus.com

What inspired you to start your own business?

I spent most of my fashion career on a successful, but traditional, path. I worked at an enviable brand in New York with an office overlooking the water and a team reporting to me. But I woke up on a Sunday and knew that the career I’d spent over a decade building wasn’t one that I was truly passionate about.

It took a few years of not-quite-right international consulting opportunities to understand where my passion truly lies. Through these experiences, I was able to dissect what my strengths are and recognize where I felt most fulfilled: connecting with and empowering women who run artisan businesses, and making personal connections on a smaller scale and one-on-one.

From this place, I launched my coaching practice in addition to The Collective {of Us}, which is an empowered group coaching and strategy community for women small business owners.

What inspires your work and what sets you apart from everyone else?

My day to day experiences inspire me to write my Instagram posts, or hop on Periscope and talk about; whether it’s on a call with a ladyboss, working with my students at Parsons, taking a yoga class, or even just walking in my Brooklyn neighborhood. We all have things the drive us, deter us, or make us wonder if we’re making the right choices. It’s about getting into action ANYWAY that makes a huge difference and I help my tribe cut through their own BS and tap into their badassery instead.

I suppose what sets me apart is my background. I’m a business coach that comes from the global fashion business and yoga world. My style of working with others is very much represented by that. Plus I’m known to throw in a sassy swear word or two in almost everything I say, which has become a huge part of my brand. I have a wide lens because of my own varied background, so I’m able to intuitively support other women in business in kicking ass in whatever they are working on..

What is your background and how did you develop the skills to start your business?

My career has been an inspired swirly road that got me to this awesome place. I graduated from the Fashion Institute of Technology in New York with a Masters in Professional Studies with a focus on global business. Formally, I’m a multidisciplinary accessories product developer with a focus on global relationship building and strategy. I did that for 15 years before launching my coaching practice. Along the way, I also received my 500-hour certification in yoga teaching and became an adjunct professor at Parson’s. Strategy and teaching is where I’m most comfortable and when I finally tapped into that and launched my coaching business; I knew I was doing the work that I’m meant to be doing.

What has been your biggest success to date?

I am not really impressed by big names or the PR stuff. I never have been, even in my former career. Though I’ve had a lot of awesome opportunities like being interviewed by the Huffington Post, featured in a campaign for The Limited on the new face of women leadership and even a feature in Design Sponge, my greatest success is when a woman that I work with emails me (sometimes in tears) because she realizes her own power and badassery and attributes some of that knowledge to having worked together. THAT is beyond my own comprehension and THAT is what inspires me to do the work I do every damn day.

What has been your biggest challenge?

My biggest challenge has been letting go of the result of the work that I do. The most challenging component of coaching is that ultimately, the accountability for these businesses relies solely on the actions of the owners and sometimes, those decisions aren’t in alignment with what I’d recommend. Over time, I’ve learned that my role is to coach with integrity and then let go of the end result. This has proven incredibly successful in work and in other aspects of life.

Describe your typical work day.

I work from about 10am -8pm give or take a few hours and I move between my Brooklyn apartment, cafes and an office in Manhattan. Every day is different, but I often start with a morning meditation or Morning Pages to set the tone. Then I sit down and outline the 2 or 3 major things I HAVE to accomplish that day, plus the rest of my to-dos. Oftentimes, I’ll either hop on Periscope if I have something important to share with my tribe or I’ll likely get on a call with my Project Manager. I teach a class at Parson’s so I’ll usually spend a bit of time preparing or teaching.


Lately, a lot of my time is dedicated to content for my Bold Business online course and The Collective {of Us}. When I’m not working on that, I have collaboration meetings around Brooklyn or I’m on coaching calls with my clients. As often as I’m able, I’ll squeeze in a yoga class between working, which keeps me grounded from all of my day to day work. It’s a busy schedule but I love what I do so it doesn’t feel overwhelming, thank goodness!


Which small businesses are you inspired by?

I’m most inspired by the women of The Collective (of Us) who’ve truly created major shifts in their business through encouraging and supporting community while building kick-as businesses (erghmmm, Esther of Cuteheads!).

If you could go back to the beginning knowing what you know now, what would you have done differently?

Failure is part of the growth process so truly, there isn’t much that I would do differently. However, I do think, given the opportunity again, I would’ve been more financially prepared. Fully committing to starting a business can be an expensive venture. Success doesn’t come overnight so having 8-12 months in savings would be a really smart place to start. I’ve heard some people recommend 6 months savings in order to to quit a job but starting your own business is a very different timeline.

What’s your best advice for someone who wants to start her own creative business?

The number one piece of advice that I offer women business owners is to build a network of support amongst other women. If you can’t find an existing network that feels authentic, then create one. It will grow. Supporting, uplifting and sharing with one another is the strongest way to grow a business. More than ever, collaboration is overtaking the concept of competition in the profitable small business world. I founded a group called The Collective (of Us), which is based on this exact principle because together, we all rise.

To read more creative entrepreneur profiles, follow the entire “10 Questions with” series.

10 Questions with Cyndie Spiegel, creative entrepreneur | Read more at blog.cuteheads.com

50 thoughts on “10 Questions with Cyndie Spiegel, founder of The Collective of Us

  1. Awesome interview and such an inspiring person. I appreciate other women who are working to effect change and bring about meaningful impacts in the lives of others. Very good stuff!

  2. That challenge: No matter what you do, a person’s success depends on how they apply the knowledge and wisdom you share. This is a mother’s challenge too! As I watch my kids blossom into adults, I am often elated, but sometimes, seeing them “learn the hard way” is heart-breaking.

    As a businesswoman: I am applying this tip — set 2-3 goals per day — hopefully, that will help me set a more reasonable pace without guilt. I’m still a mom first, and businesswoman second, so I need that balance. Thanks!

    1. Karen, I love that you can take this interview and apply it to both motherhood and business. Thank you for allowing me to see things differently TOO! x

    2. KAREN! Thank you for your comment. And, Yes! I don’t have kiddos of my own but exactly as you said – watching others “learning the hard way” can be so tough.

      Kudos to you for trying out the daily goals – let us know how it goes!

  3. I’ve enjoyed your “10 Questions With” posts and this one is excellent. It’s refreshing to see women like Cyndie Spiegel lead the way for women to go after what they want in life. I especially liked what she said about not being impressed by big names. Great read!

  4. This was such a fabulous interview. I love reading about women like this who are encouraging other women to pursue their dreams and become successful in business! This is a very inspirational interview!

  5. So very inspiring! I love the idea of The Collective Us. What a great way to communicate and interact with other like minded women. This was a great interview with Cyndie Spiegel. So honest and uplifting.

  6. I loved your line “The number one piece of advice that I offer women business owners is to build a network of support amongst other women.” That is SO important. Women need to build each other up! Fabulous post!! 🙂

  7. Cyndie sounds like an amazing woman and this Q & A with her was such an inspiring read! I love reading about creative entrepreneurs and small business owners, they are what keep me moving toward my dream!

    1. Vicki – YES. Keep yourself in environments like these and face your fears each and every day. Thank you thank you for reading!

  8. I am inspired by this interview. I’m still trying to weed through where money is well spent in building my business and what I want my work day to look like. I am energized by community and feedback. It’s something I know is missing currently. Thank you for this insight!

    1. Thanks so much for sharing, Kallie! You’re not alone, I promise. Community is huge – see if you can start by asking a few ladies in business you trust if they’ll join you for an informal mastermind or call so you can support and hold each other accountable!

  9. It’s an interesting read! I love the fact that the importance of collaboration is emphasized in building small businesses. Her comment on biggest success is inspiring!

    1. Thank you Emmanuel! Collaboration has been huge in my business and in that of my clients, that’s for sure. Truly appreciate you taking the time to share your thoughts.

  10. This was a great read. I am going to hop over to check out her site! I can’t wait to read your next installment!

  11. I love reading these! What a great story – love your thoughts on failure, building a network, and preparing financially before jumping into starting a business! And Cyndie you are gorgeous!

  12. Oh my! Is Cyndie amazing or what!! I love her phrase ‘badassery’ she is a take no prisoners, pave your own road kind of lady, I can totally relate to that! I need to follow her immediately. I have come across so many ‘business coaches’ in my blogging career, but she is the real deal!

    1. Alissia, thanks for reading and do follow along! I’m mostly over on Instagram @cyndiespiegel. Please pop by and say hello!

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About Esther

The Cuteness: sharing daily inspiration, kids fashion, work/life balance + small business how to's from mom & business owner Esther Freedman