Shannon Siriano Greenwood

There is this myth that I think many people believe that at some point you build enough confidence that hearing no doesn’t bother you. I don’t buy it. I hear no, I let it sting, I take a break and then I try again.


Shannon Siriano Greenwood knows first hand that the most powerful thing we can do is live life on our own terms.

As founder of the Rebelle brand – a national conference and community designed to help women think differently about how they live, work, create and connect – Shannon elevates the stories and experiences of people who dare to be different to inspire and guide others as they design lives they love.

A successful serial entrepreneur, Shannon has worked locally and nationally building her own business ventures and coaching others as they grow their own. She was recently named by Richmond Magazine as one of the top 5 influential change makers for her leadership in the entrepreneurial community. Connect with her at and find out more about her events and community at

Where did the idea for Rebelle come from?

Living a life that fulfills me is something that I have been truly focused on since my battle with postpartum depression. Before my depression, I was a work work work, hustle hustle hustle, bring on all the projects all the time, no need for downtime or rest or delegation.

It was not until I LITERALLY couldn’t do it anymore (my brain and my body was shutting it down) that I started searching for another way. I created Rebelle because I personally wanted to connect with women who were doing things differently; making their own schedules, doing work that they love, building businesses around their own unique skill sets, educating people about things they are passionate about, connecting, collaborating, protecting their time, and prioritizing their own development, health and happiness.

What does your typical day look like and how do you make it productive?

There really is no typical day and productivity comes and goes for me.

I have two little boys, so I am always awoken by one of my children screaming “Mommy”. I get up and try to patiently usher my boys through our morning routine, breakfast, get dressed, brush teeth, then put shoes on. (On the days that they refuse shoes, we walk to the car barefoot. This is a lesson I learned through entrepreneurship – i.e. pick your battles.)

After I drop them off at preschool, I take an hour for myself to shower, meditate, go for a walk (sometimes play a few rounds of candy crush). Having time to center in the beginning of the day, is how I stay productive.

Then I pack it up and head to a women’s only coworking space where I work, dedicated, out of the house workspace is key for me. I write down my goals for that day and do the needed email/admin before lunch.

I usually have lunch with a friend or potential partner for Rebelle and my afternoon is typically spent meeting with potential partners. These could be speakers, sponsors, contributors, or my Rebelle team members. I try to end each day with a plan for the next. This definitely helps with focus and with closing the day so I am not still in brainstorm mode once I get home.

How do you bring ideas to life?

Rebelle ideas come to life because of the team and because of really short deadlines. I love to brainstorm, but only for a very short period of time. I surround myself with action oriented people in order to get things done. We get an idea, we jump on it.

What’s one trend that excites you?

Diversity and Inclusion conversations becoming mainstream. More of this please.

What is one habit of yours that makes you more productive as an entrepreneur?

I literally have no chill. I wish I didn’t feel the need to execute all of my ideas, but once I have a good one, I want to make it happen whether it works out or not.

What advice would you give your younger self?

Keep going.

Tell us something that’s true that almost nobody agrees with you on.

You do not have to work harder than anyone else to become successful.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Keep showing up. People tell me no all the time. I take it totally personally. That doesn’t stop me from showing up again and again. There is this myth that I think many people believe that at some point you build enough confidence that hearing no doesn’t bother you. I don’t buy it. I hear no, I let it sting, I take a break and then I try again.

What is one strategy that has helped you grow your business?

Network network network. I am constantly connecting with new people and building relationships with those people. It is amazing to me how those relationships have followed me across industries. Students who took my classes when I owned a fitness studio are now the corporate partners for my women’s conference. Meet new folks and nurture those relationships, a good strategy for entrepreneurs and for professionals in general.

What is one failure you had as an entrepreneur, and how did you overcome it?

I had a terrible break up with my business partner when I was struggling with postpartum depression. It took me a very long time to bounce back from that. I grieved the loss of that business like it was a human. It was my first business and I learned a lot of lessons the hard way. The only way I overcame was through time and soul searching. I started working with a therapist who told me to go to a cemetery and cry at a gravestone to work through the grief. I did and don’t care how crazy that sounds. It was extremely healing for me. I learned that it is a very bad idea to make your business your identity, no matter how “successful” the business becomes.

What is one business idea that you’re willing to give away to our readers?

Can someone please create a “Yelp” style review site for Venture Investors? Would love to have Glass Door style feedback on the people investing in startups.

What is the best $100 you recently spent? What and why?

A months worth of Starbucks Chai Lattes. I am totally addicted. I know this and I was trying to quit and/or cut back on this “extravagant” expense especially since my organization educates women about personal finance and to many a finance expert a latte is a big no no. But you know what? I love them. They are overpriced, over sugared, but I love them. It’s my money and I will spend it on what I want. End rant.

What is one piece of software or a web service that helps you be productive?

Slack is my jam. I know this may be a no brainer, but it completely changed the way my team collaborates. We are a group of freelancers spread across the country. We like to send gifs and are definitely not using it to the full capacity, but it is so much better than a million emails with everyone CCd.

What is the one book that you recommend our community should read and why?

Currently reading Playing Big by Tara Mohr. This book changed my life and is a must read for women, especially those starting out to understand how your own self doubt and inner critic shows up in your work even when you don’t think she is.

What is your favorite quote?

It has to start somewhere, it has to start sometime, what better place than here, what better time than now. – Rage Against The Machine

Key Learnings:

  • All I can do is keep showing up
  • I am super grateful for the relationships I have built, they matter
  • My favorite thing to do is Rebelle