The Messy Parts with Maryam Banikarim

Episode: Vicki Freeman: Finding Your Calling Through Trial and Error
Date: July 7, 2025

Overview: Embracing the Twists, Turns, and Failures

In this candid conversation, Maryam Banikarim sits down with renowned restaurateur Vicki Freeman, co-founder of the Bowery Group, to explore the unpredictable journey of finding one’s calling. Freeman, whose celebrated restaurants include Cookshop and Shuka, shares how her path to success was anything but straightforward, marked by relentless trial and error, failures, resilience, and a continual search for “the fit.” The episode dives deep into the realities behind a seemingly glamorous career, demystifying achievement and celebrating the messy, unfiltered parts of professional and personal growth.

Key Discussion Points & Insights

1. Searching for a Calling—The Many Pivots

• Vicki’s Restlessness and Experimentation

  • Freeman attended nine different schools, trying on majors from child psychology to art history, but never feeling "the fit."
  • Throughout her search, she always worked in restaurants, initially just to pay bills.

  • "Never in my wildest dreams did I ever think in all of this that would be restaurants." (Vicki, 01:24)

• Financial Pragmatism

  • Driven by a desire for security, not wealth:

    • "I never had this thing where I need to be rich. But I definitely didn’t want to spend my whole life worrying about money and how to pay the bills." (Vicki, 03:28)

  • Supporting herself from 18, she enjoyed the entrepreneurial side of waitressing.

2. The Power of Initiative and Self-Belief

• Early Confidence at Ralph Lauren
  • At 19, Vicki proposed to Ralph Lauren executives that she could overhaul their inefficient buyers’ lunch system, despite having no professional cooking background.

  • "Something in me said, I can do this. Which is really crazy because I wasn’t a cook." (Vicki, 06:12)

  • This initiative launched her into 11 years running a catering business, though she realized catering wasn’t her passion.

3. Hit Bottom, Look to the Sky—Finding Openness

• After a restaurant closure and personal upheavals, Vicki describes a pivotal “Oprah moment”:

  • "I just remember sitting in the kitchen and looking to the sky and saying, okay, I’m open. Like, what is it?" (Vicki, 09:35)

• Serendipity and Saying “Yes”

  • The very next day, a friend offered her the chance to run a coffee bar, which quickly evolved into her first restaurant, Vicks.

4. The First Big Success and an Even Bigger Fall

• The Rise of Vicks

  • Vicks quickly became a celebrity hotspot, but Vicki lacked back-of-house business experience.

  • "So I thought this restaurant business thing is easy and I’m so cool and look who's calling me...it was just a crazy experience." (Vicki, 13:24)

• Hard Lessons from Failure

  • Only one year later, Vicks closed.

  • "It came crashing down so hard on me ... I really think I was, like, in a depression. I didn’t work for three months." (Vicki, 14:41)

  • She believed her shot was over:

    • "I had my one shot. I blew my one shot, and that’s it." (Vicki, 14:41)

5. Bouncing Back—Learning, Grafting, and Grit

• Mentorship and Skill Building (Columbus Bakery)
  • Jonathan Waxman prompted her to get back into restaurants, a move that Vicki likened to "witness protection" on the Upper West Side.
  • Four years managing Columbus Bakery provided “the best education” in finances and operations.

  • "What was great...was to have somebody really teach me the finances of it and how important they are." (Vicki, 17:30)

6. Reframing Money—‘Investing in People’

• Funding Five Points
  • Unable to raise large investments, a mentor advised her to sell small shares to many people:

    • "He said, you are giving people an opportunity...the more investors you have, the better." (Vicki, 20:05)

  • A pivotal investor contributed because he had witnessed her dedication:

    • "I invest in people. I don’t invest in businesses and ideas." (Investor, 22:13; recounted by Vicki)

7. Restaurants as Community Connectors

• Institutionalizing Hospitality
  • Vicki’s restaurants became neighborhood institutions, highlighted during the post-pandemic reopening:

    • "One of the best days of my whole life was the reopening of Cookshop during the pandemic...The neighborhood showed up. Even makes me emotional talking about now." (Vicki, 23:18)

8. Resilience Amidst Catastrophe (9/11, Pandemics, and More)

• The realities: she survived failures, natural disasters, major blackouts, the pandemic, and evolving industry norms.
• On the pandemic:

  • "There are times I’ve curled up in a ball...those three months of shutdown were actually...such a good thing for me." (Vicki, 26:17)

• Learned to value reflective silence and creativity in crisis.

9. Backing Chefs, Not Trends

• Every restaurant centers on empowering stand-out chefs.
• The story of Shuka: evolved from a failed concept, inspired by chef Ayesha’s Middle Eastern creations, to a shared vision that became a hit.

  • "Every restaurant I’ve ever done has been about the chef. Every single solitary one of them." (Vicki, 28:53)

• Key: Even big successes like Shuka started with uncertainty and risk.

10. Partnerships and Community—At the Core

• Works with five partners in the Bowery Group and her husband, Mark.

  • "Give up the money for…having all that support and going through a pandemic with partners." (Vicki, 34:01)

• Acknowledges the messiness and magic of working with a spouse:

  • "Our first year, we fought every night…But it’s been an incredibly long learning." (Vicki, 35:45)

  • "I don’t think we could have done what we did if one of us worked 9 to 5." (Vicki, 36:04)

11. State of the Industry—Persistent Financial Pressures

• Prices are rising dramatically, but restaurants can’t “outprice themselves" to customers.

  • "The price of eggs is the price of everything for us. And we cannot just raise our prices in conjunction with how much the prices are being raised to us." (Vicki, 36:45)

12. Continued Searching and Next Chapters

• Even now, Vicki wonders if there’s “something else” she’s meant to do, remaining open to possibilities.

  • "Is there something that for me, not that I won't do more restaurants, but is there also something else? ... It’s hard…to tell you I don't know, but I don't know." (Vicki, 37:41)

Notable Quotes & Memorable Moments

• "I believe that you should try things. I don’t believe that you sit around and hope something comes to you..."
  — Vicki Freeman (01:50)
• "Sometimes I still don't know what's good for me...That was the best thing that could happen to me."
  — Vicki Freeman, on Vicks closing (13:45)
• "He said, I invest in people. I don’t invest in businesses and ideas."
  — Investor, recounted by Vicki Freeman (22:13)
• "I have to get open…in the middle of this hellish experience…I felt like it was a place people felt a connection to."
  — Vicki Freeman, on Cookshop reopening post-pandemic (23:18)
• "But how do you keep going?…how do you not just be mad at an obstacle?"
  — Vicki Freeman (25:30)
• "Every restaurant I’ve ever done has been about the chef. Every single solitary one of them."
  — Vicki Freeman (28:53)
• "You are giving people an opportunity…you're giving them a chance to be part of something."
  — Advice from Michael Weinstein (20:23)
• "I actually now am at the point in my life that you have to have a vision. That much I do think."
  — Vicki Freeman (33:51)
• "I love partnerships. I love community. I love the community of restaurants. Like, I’m not a lone wolf in any way."
  — Vicki Freeman (34:38)
• "Just keep on trying things. Keep going. Don't just give up. Don't just sit there. Keep trying and keep doing things. But go for things you feel passionate about."
  — Vicki Freeman (40:44)

Key Timestamps for Important Segments

• 01:24: Vicki on constant searching and working in restaurants by default
• 03:28: On fear of financial insecurity
• 06:12: Telling Ralph Lauren she could do it better
• 09:35: The "Oprah moment" — looking to the sky for answers
• 13:24: The heady days of Vicks—and her business naivety
• 14:41: The devastating closure of Vicks
• 17:30: Columbus Bakery as a crash course in business fundamentals
• 20:05: The “investing in people” moment that made Five Points possible
• 23:18: Emotional community support re-opening Cookshop
• 25:30: Picking yourself up after countless obstacles
• 26:17: Pandemic shutdown as a (surprising) period of personal growth
• 28:53: Why she always backs chefs, not trends
• 33:51: On the necessity of having a vision
• 34:38: Power of partnerships and community
• 36:45: Financial challenges plaguing restaurants post-pandemic
• 37:41: Remaining open to future pivots and passions
• 40:44: Vicki’s core advice: keep going, try things, follow passion

Rapid-Fire Q&A (38:35–41:00)

• Karaoke or walk-on song:
  • Refuses to sing, but likes Paul Simon or, as offered by Maryam, “Girl on Fire”
• Potluck go-to:
  • Smoked fish and bagels from Russ and Daughters
• Alternate career:
  • Small grocery store owner, maybe fashion
• Current reads/watch:
  • Re-reading Eckhart Tolle’s New Earth; watched “The Order”
• Unexpected fact:
  • Has terrible stage fright

Advice: For Listeners Still Searching

"Just keep on trying things. Keep going. Don’t just give up. Don’t just sit there. Keep trying and keep doing things. But go for things that you feel passionate about. I really feel strongly that if you’re passionate about it, if you love it, it will probably work." (Vicki, 40:44)

Tone of the Conversation:
Raw, honest, and encouraging—full of warmth, humor, humility, and a “keep-it-real” attitude about success, failure, partnership, and perseverance.