In Conversation with Jaclynn Brennan of Fylí

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Describe your business in a few words?

Fylí is a female master-mind group started by myself + close friend Summer YL in 2019. We help female leaders RISE (Renew, Inspire, Support, Empower) in all aspects of their lives.

Fylí was created to bring together a room of diverse thinkers and dreamers who can shift conversations, contribute new opinions + feedback, and bring different perspectives with clarity and directness that moves the needle. Magic happens when you feel open, connected, present, vulnerable and safe. We learned early on that success is only limited by our mindset, habits and the people we have access to within our network. When you UPGRADE your thoughts, daily disciplines/habits and relationships, you begin to upgrade your life.

What made you take the leap to start your own business?

Over the years I had the opportunity to work with so many amazing female leaders that empowered me to be strong, to make bold asks, to go after what I want and that inspired me to take the power into my own hands and carve out my own path. I always considered myself an entrepreneurial person, after years of helping others build their businesses, I discovered my true passion of combining connecting others + branding. I started Creative Duality, my consulting company first.

After joining a predominantly male lead fashion tech start up- I saw a HUGE need for an organization that caters to female entrepreneurs. Not just another “networking” group, but a true master mind that combined education with REAL resources and accountability. I met my business partner and best friend Summer at a female founders pitch event, and after lots of brainstorming, research and iterations we created Fyli out of our own personal needs.

What was your background prior to starting your own business?

Prior to starting my own business I worked in the fashion industry. GIRL I started out doing 5 unpaid internships after college!! I didn’t come from a prestigious or “well-connected” family in New York, and knew that I needed to work hard to get to where I wanted to be. I wasn’t the smartest, or prettiest, or most connected BUT I would outwork anyone. My work ethic and drive helped me propel in my career at a young age. By the age of 25 I was named Creative Director for a prestigious fashion jewelry company based in NY had had the opportunity to expand their business to handbags and eyewear.

After that, I worked for an accessories brand that eventually pivoted into a 501c3 non profit organization focused on girls education and empowering artisans around the world. I had the opportunity to meet so many amazing women, to be around incredible leaders, and to build my own relationships with women I greatly admire. I am forever grateful to the amazing mentors and role models in my life who opened the door for me and helped me believe in myself.

Did you always know you wanted to be an entrepreneur?

YES! First of all, I always wind up rewriting the rules (or breaking them and doing things my own way). I have never been afraid of taking risks or rolling up my sleeves to do the work. Being an entrepreneur is HARD AF- you often see all of the glamorous galas and events and fun photos. You don’t get to see the long nights, weekends of work, or roller-coaster of emotions that go along with it. Although it’s never easy, I wouldn’t trade it for the world.

Take us back to when you first launched your business, what was your marketing strategy to get the word out and did it go as planned?

Summer YL and I first launched FYLI through a partnership with Soho House New York. We used our co-working space as a “soft launch” test market to see how many women were interested in what we were offering. After attending Brendon Bouchard’s High Performance Academy conference, I learned the importance of master-mind groups and how so many people are not even aware of that term. The original term “master mind” was coined by author Napoleon Hill in 1925.

At our first launch event we had over 100+ women (capacity was only 75) and it was the most attended Soho House event of that quarter. We realized then and there that women WANTED Fyli to level up and invest in themselves and their futures. That evening our inbox was filled with application forms for women who wanted to be a part of this community.

What is the accomplishment you are the most proud of to date?

I am so proud of our small and mighty team: Summer YL (my partner & Fyli Co-Founder), Catherine Sypert (Fyli’s Head of House & 1st full time employee), and Kate Kelley (Director of Partnerships) for what we have accomplished in just just 1.5 years. We started out as a community of 380 women in New York and now we are 6,000 (AND GROWING) globally! We opened our second cohort November 2020, and launched a new product called the “Fyli Tribe” subscription in August.

I am proud of the amazing partnerships we have cultivated in a short amount of time including: GOOGLE, Lyft, Soho House, CORE:Club, The Well, Boxed Water, and WW (formerly Weight Watchers).

I am also extremely PROUD of the founding Fyli Cohort members who helped structure and create programming, who leveled up over the past year, and who really stepped into wonderful leadership roles and led their teams into success despite a global pandemic.

When hiring for your team, what is your go-to interview question? Please share any hiring tips you can share from your experience?

When hiring for our team (whether full time, contractors or interns) I ALWAYS believe that action is better than talk. I like to learn about people’s core values and motivations, but more importantly I like to see their passions and skill sets in action. I always give a little test project to put their skills to work before making a hire.

My tips are to be completely HONEST and transparent about the role. To be a passionate and kind leader, take time to hold space and be present for your team or new hires.

How has your business or industry been impacted by the COVID-19 pandemic?

The past few months have been HARD. I think we only had 2 options: 1. To feel sorry for ourselves and shut down 2. To Pivot and pour everything we have into our community.

Within 24 hours of lock down Summer and I started calling everyone in our rolodex to amp up virtual sessions to almost 2/3 per WEEK. We knew we needed to do something more for our community who was 80% in NYC and in lock down.

No more in person events, no more dinners or panel discussions, no more round table bonding breakfasts. We worked extremely hard to create authentic and unique 360 virtual programming and events that inspired or tribe and brought everyone together. We even offered FREE programming for the past 5 months as we knew so many founders were struggling and business was suffering. We simply wanted to add value and lift everyone’s spirits. Fyli is now a global community.

What’s next for your business? What can we expect to see over the next few years?

We are opening our second cohort in November 2020, and you can apply by visiting or join our TRIBE subscription (low fee monthly no commitment virtual community). Our goal is to have 4 cohorts running by the end of 2021.

Within two years we hope to expand with physical Cohorts in NYC, LA, ATX, and San Fran. Our dream is to start a fund to support female entrepreneurs and empower the next generation of strong female leaders.

What do you know now that you wish you knew when you were first starting your business?

There are a few things I wish I knew:

1. Let go of ego (it’s not important)

2. Don’t be afraid to ask (the worst that can happen is someone says no)

3. Get comfortable being uncomfortable (difficult conversations are worth having early on)

Do you believe in work/life balance? What are some of your best tips?

I believe in setting healthy boundaries and setting expectations for teams, employees, clients and partners. My best advice is to go at your own pace and OWN your day. Someone’s “emergency” is NOT your urgency.

I am lucky enough to make my own schedule and I structure it in a way that truly works for me. Monday’s I try not to schedule ANY meetings or calls. This is an internal day of of preparation and execution for my week. Tuesday/Fridays I stack my days with meetings and calls and Wednesdays/Thursdays are my days to create & design for my clients.

What’s something our audience would be surprised to learn about you?

That I grew up in a small town in New Jersey and always felt out of place. I HATED high school, I never felt like I “fit in”. I went to a VERY small all girls school and didn’t really “find myself” until college. My dreams were so big that people would say “who do you think you are”?

What are your top 3 tips to stay productive each day?

1. Success starts the night before. Each night before bed I PREP my to-do list for the morning, confirm my day, and start visualizing how I want my day to run.

2. I have a pretty solid and structured morning routine that I try my best to stick to: exercise 1st thing, mediation, journaling. Try my best to allocate 2 hours each morning before I start my work day. This doesn’t always happen, but I feel my best when I take time for myself in the morning. I also set 1 hour time blocks to structure my day efficiently.

3. Giving gratitude throughout my day. To the universe (or god), to my family and friends, to my team/clients/employees, and most importantly to myself. This helps me not only be more productive, but to feel “in flow”.

What does being an Entreprenista mean to you?

An Entreprenista is a strong, kind, and determined leader who is not afraid to carve out her own path in life. She is a woman who cares about others, who uses her influence for good, who empowers others around her to do and be their best.

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