Alright – so today we’ve got the honor of introducing you to Penny Goffman. We think you’ll enjoy our conversation, we’ve shared it below.

Penny , looking forward to hearing all of your stories today. Getting that first client is always an exciting milestone. Can you talk to us about how you got your first customer who wasn’t a friend, family, or acquaintance?

This is a story about how I landed my first 3 clients in the first 3 months that I went out on my own recently. The common thread of all 4 projects is CONNECTION. For 5+ years I was Head of Community at HeyMama, a private membership community for moms in business. During that time, I met inspiring, brilliant and powerful women across the country building incredible businesses. My role was forward facing and I had a unique opportunity to deeply connect with our members & partners. I supported them, introduced them, cried with them, lifted them up and above all did so with authenticity. It wasn’t until that business sold that I understood the magnitude of these connections. In January 2025, I leaned entirely into these relationships to guide me on this next career chapter. While connections are critical, your name, reputation and how you make people feel are everything. My very first client of 2025 was a previous HeyMama member, who remembered me as a ‘power tool’ (her words) and reached out almost immediately to help produce her summit. It was an incredible opportunity, especially as my first project on my own, that fell into my lap simply because I kept the lines of communication open over the years and my reputation spoke for itself. However, the next 3 came by a different path. I tapped deep into previous partnerships, those that I intimately was involved in, knew the ins and outs of, ran by female founders I greatly respected. How? I emailed them, yes that simple. I did not sit back and wait for more opportunities to magically appear. I directly emailed the founders, even those running huge national businesses with comprehensive teams. I slid right into their inbox, reminding them of the collaborations and previous events I had worked on with their brands. Again, replying on the connection & my reputation. The best part, in both cases I had a reply same day, setup meetings and thrilled to announce I’m working with one on an ongoing basis and just wrapped a beautiful oceanside curated luncheon with the other. The moral of the story, and what I’d love for readers to take away is this: 1. Creating an authentic community of contacts and support is critical in building a business at every stage. Stay in touch. Connect on a personal level. 2. You have the contacts but then what? Your name, your quality of work, your energy and what you bring to the table will carry those connections to the next level. Deliver your best self. One job well done, can lead to 10 new ones. 3. No one is off limits. Period. We are all human, and in this case building brands. Every smart founder, even that of a global business wants creative ideas and new eyes. Be thoughtful in your pitch. Be specific. Know the connection. Go for it!

Penny , love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?

Top level, here’s what you need to know:
I’m a mom. I curate experiences and events that connect women leaders to each other and brands. I’m hot. Happily married. I bring magnetic energy to everything I touch.

Intrigued? Then the details are for you:

Penny Goffman is known for her ability to connect and empower women. In January 2025 Penny Goffman launched a boutique consulting agency to curate bespoke experiences and position brands within their targeted communities. She is known for her ability to connect guests and empower audiences. She specializes in hosting dynamic curated experiences that create community around a brand, driving organic customer acquisition, visibility and brand loyalty. Her genuine ability to connect power players, leaders and guests to top-tier brands is what sets her apart.

For the prior five years, Penny Goffman was Head of Community at HeyMama, a private membership community for moms in business. She fostered community connections and member relationships across the country through engaging events and strategic communications, enabling them to grow both their networks and net worth.

An accomplished writer, Penny has published several articles on motherhood and community, including contributions to Bella Media. Previously, she founded Jolie Gotique, a creative mobile fashion pop-up boutique, which she successfully sold. Penny worked as head fashion stylist and MC, for high-profile clients like Bloomingdale’s, Lord & Taylor, Alice & Olivia, and Athleta. She regularly steps onto the live stage, moderating and speaking on panels nationwide, with a focus on motherhood, entrepreneurship, community, and HOT confidence.

Her expertise has been highlighted in popular podcasts, including That’s Total MomSense and That Greenwich Life, along with press features in WSJ, Greenwich Lifestyle Magazine, Greenwich Magazine, Westchester Family, HeyMama and News12.

Sounds interesting, what services do you offer?

As a Community-Brand Connector & Experience Curator, I specialize in creating meaningful connections and experiences that connect brands with target customers. By designing and executing meaningful local community events, building local event series, and securing sponsorship & media opportunities, I successfully help clients strengthen their brand presence and connect with their local target audience.
How?
– Curating local brand experiences around a popup, intimate lunch, fireside chat including aligned activations, partners and visibility opportunities.
– Facilitating brand education leading to business growth & retention
– Connecting clients with local high profile speakers, influencers, customers & media
– Strategically planning communications around events & experiences that connect with guests
– Sweet spot: Building brand relationships & connections with local women leaders

What’s a lesson you had to unlearn and what’s the backstory?

One lesson that I’ve had to unlearn over the years that seems small but has helped me tremendously in my communications, and business relationships is the power of listening more. We hear a lot about women shrinking themselves but the challenge in my case is that I never felt shrunk. There was a time, where I found myself to be taking over a meeting, jumping to conclusions or giving opinions without hearing the full story. My husband and kids would probably say this is still true at home, work in progress! Listening & pausing lead to strategic thinking & communication. How did I realize? When I started feeling shitty after work meetings. I had to really dig deep and think about how others are feeling on the call or in the boardroom if I’m voicing myself but not truly listening to their end. It derives from a place of passion, excitement and wanting to problem solve. I’ve learned that by listening & pausing more, we set the stage for deeper collaborations, authentic relationships and a more successful foundation forward.

Alright – let’s talk about marketing or sales – do you have any fun stories about a risk you’ve taken or something else exciting on the sales and marketing side?

A few months ago, I was at a female founder summit and the keynote speaker was an incredible global female founder & mom, who IPO her first business in the tech space, sold it for 500 millions in cash, and was now building her second business in the AI mom space. Impressive to say the least! Her keynote at the event touched my soul and I was actually crying. When she was done and stepped off the stage, she headed straight to the back of the big hotel conference room with her team to exit. The summit was far from over and a panel discussion was taking the stage. On an absolute spontaneous whim, without any prior planning, thought or strategy, I found myself getting up from my seat and following her & the entourage out the door. I hadn’t thought it through whatsoever, but something pulled me at that moment to introduce myself and further make sure she would remember me. Out the door, I walked right up to her from behind, tapped her back and in 45 seconds or less told her who I was, the business I worked for, the high profile members in my orbit and what I could do for her new business. With zero preparation, it happened in a flash, but when you really understand your value and what you can pr0vide, no preparation is needed. She thanked me, and told her PR assistant to take a photo of us together so she’d remember me, then told me to message her on LinkedIn. Of course I followed through immediately after the summit and she DM me back within 24 hours. Next thing, I have 2 meetings set up with marketing and the COO.

If you take anything out of this story, let it be this:
1. No one is off limits. As I mentioned earlier in this interview, every founder wants fresh, creative talent with a vision to execute. 2. Your name & reputation follow you everywhere. 3. If you don’t try, you’ll never know.

Contact Info:

• Website: https://pennygoffman.com/
• Instagram: https://www.instagram.com/thatpennylife_
• Facebook: Penny Goffman
• Linkedin: https://www.linkedin.com/in/penny-goffman-318b84338/

Image Credits

@bri.co.creates @brookroadphotography