Welcome to Chicago North Shore Moms weekly Meet a Mom series where we feature one local mama, what they’re up to both personally and professionally.
Introducing to the community a bad@$$ female founder who built a multi-million dollar community out of an idea she couldn’t shake, $500, a stack of business cards, grit, bravery and the belief that, “yes, she could.” Then she sold it, started over, and built something even bigger! Lindsay Pinchuk is the powerhouse behind Dear FoundHer…, a podcast, mentorship program, and thriving community that is actively changing the way women build businesses. I had the pleasure of hearing from Lindsay about all things entrepreneurship, motherhood, and why your story might just be your most powerful business asset. So, whether you’re in the just thinking about starting a business phase, just getting things off the ground, or seasoned and maybe feeling a little stuck, you will not want to miss a single word in our interview.
This interview is packed with nuggets of actionable advice, and loads of favorite product shoutouts – the woman knows her stuff and she’s passing it forward. Welcome, Lindsay!
Photo credit: Shay James Photography
Hi Lindsay! Give us a quick snapshot of you and your life right now.
Life right now is BUSY. In addition to being the mom of two amazing teenage girls, I am running a business with two different revenue streams. I host my podcast, act as a mentor to hundreds of women small business owners and manage/consult a couple of clients on their marketing strategies. I also accidentally fell into activism on behalf of the Jewish community post October 7th, and have that to keep me busy as well.
When I’m not working, I’m driving my kids anywhere and everywhere, making dinner for our family (I try to a few times a week depending on schedules), walking the dog, watching a show or lately I learned how to play Mahj, so I’ve been trying to get better at that.
Work also often takes me out of town; I often joke that I go to New York City more often than Chicago, but honestly, I don’t mind that at all.
Life is busy, but full, and I am incredibly happy. Probably the happiest I’ve been in my adult life.
Sounds like your cup is full and I love that for you! Where are you from originally and why did you move to Chicago?
I grew up in the suburbs of Detroit, MI and will always call Michigan home. I moved to Chicago for a job in advertising that I never started in September 2001. But a few months later I landed a job at Time Inc. After a decade in ad sales, I started my own company, put down roots with my husband and ultimately we ended up deciding to call Chicago home.
Now you’re a mom to two teen girls! What does motherhood look like in your house these days?
My daughters are turning 13 and 16 this fall and motherhood is honestly amazing. I love spending time with my girls (even if they don’t always want to spend time with me…). We love going to concerts, taking trips downtown, or just hanging out and watching movies and TV together. I love how independent they are, but at the same time relish the fact that they still want to spend time with me and my husband. I try VERY hard to have dinner together a few times a week. Some seasons it’s hard with activities. But we do our best to make it happen, or just to pick up or go out so that we can be together.
My oldest is an incredible artist and my youngest a talented softball player, so their activities keep us all busy and our calendar full.
What’s something about you that might surprise people outside of your work and mom life?
I love Bon Jovi. This summer I will see him at Madison Square Garden and it will be my 38th Bon Jovi Concert. I’ve met him, hugged him, and gone on stage with him. I am counting down the days to this show as its been years since he’s been on tour.
Where are your go-to spots right now?
Bean Bar in Northbrook and Double Cup Coffee in Highland Park (depends where my day takes me)
Bright Bowls in Highland Park or Lolo’s Bowls in Glenview (again, depends where my day takes me.)
Bloouts in Highland Park at least once a week (this is the one thing I do for myself.)
The Beauty Library for manicures (ok, the two things I do for myself.)
Dr. Julia Milman for Diamond Glow Facials (this is a real treat a few times a year.)
Ami Jerusalem Street Food (my favorite for pick up and the Chocolate Babka is TO DIE FOR), Ema, Bluefish and Guildhall for date night and girls nights.
What are you loving lately? Any books, other podcasts, shows, products or routines you can’t stop recommending?
I listen to: Call Me Back with Dan Senor, The Mo News Podcast, and Question Everything with Chicago native, Danielle Robay
I have been telling everyone they need to read: The Little Liar by Mitch Albom
I’ve been trying to go to Pvolve 2-3x per week as I know that weight and strength training are imperative for me at my age.
I’ll always love riding my Peloton. I ride with Jenn Sherman all the time.
Photo credit: Fine Photography by Stephanie
I love to recommend female founded products, here are some of my current favorites, there are so many more where these come from:
- Perfectwhitetee Ziggy Sweatshirt
- Dagne Dover Landon Carryall (I do not travel without this carry on)
- Petite Plume Pajamas (founded by local mom, Emily Hikade)
- Inspiro Tequila (founded by local mom, Mara Smith)
- Joy Creative Shop Personalized Stationary
- Jones Road Miracle Balm
- Jennifer Zeuner Sivan Charm, paired with my Sophia James Evil Eye necklace
- Fenty Lip Gloss
It’s time to get down to business! You’re a female founder with many hats, running national networking communities, offering fractional consulting, and hosting a bi-weekly podcast. Tell us about these hats!
I do wear a lot of hats, and honestly, I would not have it any other way.
The foundation of everything I do is Dear FoundHer…, a media, education, and community brand I built for women business owners, with a particular focus on women building businesses in their 40s and beyond. I launched it as a podcast right after selling and exiting my first company, Bump Club and Beyond, which I had grown from a $500 investment to over 3 million monthly users and 7-figures for six years straight, before it was acquired in 2019. I knew after that experience that I wanted to give other women the network, the support, and the marketing know-how that I did not have when I started out.
So the first hat: podcast host. Dear FoundHer… has over 350 episodes and counting. I have had the privilege of sitting down with founders like Bobbi Brown, Peloton’s Jenn Sherman, Rebecca Minkoff, Dr. Becky Kennedy, Gail Simmons, and Leah Solivan from TaskRabbit. Every conversation is built around real business, real strategy, and real stories from women who are building something meaningful.
Peloton’s Jenn Sherman and Lindsay Pinchuk.
The second hat: community builder. I run the Dear FoundHer… Forum, a paid networking community for women business owners. It is not just a Facebook group or a Slack channel. It’s a place where members collaborate on partnerships, book each other on podcasts, hire one another, and co-host events. Every month I am inside it hosting workshops, Office Hours, and networking events designed to help members actually move the needle in their businesses. I always tell the women inside, I need them as much as they need me!
The third hat: marketing mentor. I teach a 12-month group mentorship program called Marketing Made Simple for Small Businesses, built around my original framework called SWEEP: Social, Website, Email, Events, Partnerships, and Publicity, with your stories as the foundation underneath all of it. From time to time, I also take on a small number of one-on-one mentorship clients for more personalized, intensive work.
The fourth hat: marketing consultant and brand manager. Right now I only have time for two clients in this realm. One is a non-profit whose work I am incredibly passionate about. I work with them to manage their influencer relations. My other current client is a large notable personality in the fitness space. I manage her personal brand including her public appearances. This work is so fulfilling as she was a former guest on the podcast, turned incredible friend and last year she asked me to join her team.
And running through all of it is nearly 25 years of marketing experience, a business I built and sold, and a genuine belief that your story is your most powerful business asset. That is what I bring to every hat I wear.
Chicago native Kareem Wells, Lindsay Pinchuk, Activist, Tessa Veksler and TV Personality, Donny Deutsch. Photo courtesy of Anti-Defamation League.
Your origin story begins with a very well-known parent community, which you started in 2010, bootstrapped to success and sold. How did Bump Club & Beyond pave the way towards your current business models?
The sale of my company was not ideal and I talk about that all the time. People often ask me if I regret it, and the answer is absolutely not. My experience founding, building and selling Bump Club gave me the experience to do what I am doing today. And like I said, I am the happiest I have ever been.
Bump Club and Beyond taught me everything I know about building a business, and none of it came from a playbook.
I started it in March 2010 with $500 and an idea: bring expectant and new moms in Chicago together through in-person events. I didn’t have investors, a marketing budget or a million followers (social media actually didn’t even exist then.) What I had was a willingness to show up and ask. Before I had a single member, I was driving around Chicago with a stack of small cards in my passenger seat, walking into barre studios and maternity boutiques and prenatal yoga classes and asking the owners if I could leave them on the counter. Women picked up those cards and showed up to my events. That was my first lesson: you build community one real relationship at a time, not through ads.
From there, I discovered the power of partnerships, which has become the backbone of everything I do. I started working with brands on gift bags, offering them access to a highly targeted community of expectant moms in exchange for free product. Within months, those same brands were asking what else they could do, and offering to pay for it. That trade-to-paid framework built the entire business. It eventually led to a national activation program inside Target stores across the country, a six-figure partnership with The Honest Company, and ultimately an acquisition by Advantage Marketing Solutions in 2019 after growing to over 3 million monthly users.
Photo credit: Josh Schwartz of Josh Aaron Photography
What Bump Club gave me, beyond the business itself, was a proof of concept for a way of building that I now teach every day inside Dear FoundHer… I built that company on simple, repeatable marketing practices:
- telling my story
- showing up consistently
- hosting events
- building partnerships from the ground up
No funnels, viral moments or massive ad spend. Just a real community, built one relationship at a time.
When I sold Bump Club, I stepped back and looked at what had actually worked over nearly a decade, and I realized I had a framework worth teaching. That framework became SWEEP. And the knowledge that women building businesses deserve a real network, real mentorship, and real community became Dear FoundHer… Bump Club did not just pave the way. It is the living proof of everything I teach.
I have a feeling you wouldn’t change anything about the way your career has been shaped. Having said that, entrepreneurship and the life of a founder can be lonely and isolating. From bootstrapping to acquisition, what’s the one thing you wish someone had told you before you started Bump Club?
Find your tribe. Seriously. I had not ONE female founder friend when I started. It was incredibly lonely and I had no idea what I was doing. It wasn’t until I started working with other business owners and created a network for myself that I understood how important this was. Many of the women I worked with then, I am still friends with today. This was the reason I started Dear FoundHer… and in particular the Forum. I never want another woman business owner to have to build by herself again.
Lindsay Pinchuk with Chicago North Shore Moms co-founder, Ellie Ander
In your virtual entrepreneurship program, Marketing Made Simple, your SWEEP framework breaks marketing down into six tactics; which one do you think most small business owners are leaving the most money on the table with?
Partnerships. This is the single fastest way to grow your business. When you partner with entities you support and who support you, you are borrowing their community and growing yours. You also get the trust of their endorsement (and they get yours) right away. Creating the right partnerships will grow your business faster than any other form of marketing. It’s the premise I’ve built both of my businesses on over the last fifteen years.
Partnerships are not necessarily paid, they are truly collaborating with others to bring awareness and visibility to what you’re building through shared content (podcasts, social, press etc.), events, email trades, giveaways etc. Every single day I watch the women inside the Dear FoundHer… Forum create partnerships with one another, and that is part of the reason I created this space in the first place.
You give invaluable advice to your community members about how to grow their business. One thing that has really stuck with me is the call to action: “Tell your story,” and “People buy from people.” What does “community” mean to you, and how do you know when you’ve really built one?
Community, to me, is not a follower count or a subscriber number. It’s not an engagement rate. Those are metrics. Community is something much harder to measure and much more important to build.
Real community is a two-way street. It’s not a stage where you perform and an audience watches. It is a relationship where you show up for the people around you, and they show up for you. You engage with them, and they engage with you. You support them, and they support you. The moment it stops being reciprocal, it stops being community.
I learned this the first time around with Bump Club and Beyond. Long before we had a social media strategy or a PR firm, I was showing up at our events sharing my life as a pregnant woman and then a new mom, the good, the bad, the exhausting, the hilarious. And the women in that community did the same right back. They shared it with me. They told me what they needed. They brought their friends. They showed up every single month because they felt like they belonged to something, not just something they were consuming, but something they were actually a part of.
That reciprocity is what built the business. Not ads or a big launch. A community that felt genuinely invested in what we were building together.
I carry that exact same principle into Dear FoundHer… I tell my story, including the hard parts, and my community tells me theirs. When I go quiet, they check on me. When they go quiet, I notice. When a member lands a new client through a connection she made inside the Forum, I celebrate that as loudly as I would celebrate my own win, because it is my win. That is what happens when community is working the way it is supposed to.
And here is what I tell every founder I work with: your community is your single greatest business asset. Not your product. Not your social media following. But, your community. Because when you have a real one, your people become your marketing. They refer you. They vouch for you. They show up to your events and bring a friend. They buy from you again and again, not because of a discount code or a retargeting ad, but because they trust you and they want to see you succeed.
The phrase “people buy from people” is true, but I would take it one step further. People buy from people they feel connected to. And that connection only happens when you are genuinely invested in them, not just in what they can do for your bottom line.
You know you have built a real community when your people start doing things you did not ask them to do. When they connect with each other without you facilitating it. When they defend your brand publicly because they feel ownership over it. When they send you a DM just to say they’re rooting for you. I still hear from women who were part of the Bump Club community years, seven years after I sold that company. That is what real community does. It outlasts the business model. It belongs to the people in it.
This is the standard I hold myself to every single day with Dear FoundHer…, and it’s the foundation I help every woman in my community build for her own brand.
What do you want our readers to know that we have not already covered?
It’s never too late to do the things that you want to do. Whether its learning a new skill, starting a new business, or traveling to see a place on your bucket list. If something is keeping you up at night, act on it. We get one shot and it’s up to you to make the most of it.
Where can we connect, ask questions, book a consultation with you, start the Dear FoundHer… FORUM or the MMS program, attend in-person events, etc.?
Connect with me on Instagram:
http://www.instagram.com/dearfoundher
https://www.linkedin.com/in/lindsaypinchuk/
Subscribe to The FoundHer Files: http://foundherfiles.substack.com
Join the Dear FoundHer… Forum: https://www.dearfoundher.com/dear-foundher-forum
Listen to the podcast: https://podcasts.apple.com/us/podcast/dear-foundher-real-founder-stories-for-women-small/id1591976277
All information about Dear FoundHer…, our podcast and community can be found at http://www.dearfoundher.com
About Our Spotlight Partner
Chicago North Shore Moms is supported in part by Mary Gregory Gifford, a Lake Forest mom of three and owner of Gifford Law, a solo Estate Planning Firm (wills and trusts). Mary, we appreciate your support of local moms in our North Shore communities! Learn more about Mary by visiting her Meet a Mom spotlight here! Contact Mary directly here: [email protected].
