Buckle up for another addition to our popular mini-series, let’s dive in. PaSH is centered around sharing inspiring stories, breaking down stereotypes, and sharing the authentic, behind-the-scenes moments that make entrepreneurs so amazing. Let’s get started with, “Plentyi for Everyone: Andrea Geiger on Turning NYC’s Parking Problems into Community Power”.
Can you share the story behind starting your business and what inspired you to take the leap?
Plentyi was born out of the everyday frustration of circling blocks in NYC, losing time, money, and peace of mind just to find a parking spot. As native New Yorkers, we experienced parking tickets, towing, booting, and the constant struggle of limited spaces and limited options. We also saw how underutilized driveways, garages, and lots could be transformed into community assets. What inspired us to take the leap was a simple but powerful idea: parking shouldn’t be a stress point — it should be a shared resource. With Plentyi, we wanted to give people more than convenience; we wanted to give them back time, flexibility, and opportunity.
What’s one piece of advice you wish you could give your younger self before starting this journey?
Pick your business partners wisely!
Some key tips when choosing a business partner:
1. Look for long-term alignment, not short-term convenience.
Choose a partner who shares your core values and your vision for the future. It’s not just about where your business is today—but where you’re going. You need someone who is equally committed to the mission, even when it’s not easy.
2. Prioritize value over familiarity.
Partnerships should be based on what each person brings to the table—not just personal history or emotional connection. Evaluate what skills, resources, or insights they offer that can genuinely help your business grow. Avoid decisions driven by nostalgia, imagined potential, or unspoken expectations.
3. Invest in trust, transparency, and accountability.
A great business partner is someone you can communicate openly with—especially when the stakes are high. Establish clear roles, shared goals, and mutual accountability early on. The right partner should be someone who is invested in both your success and your sustainability.
Can you discuss any partnerships or collaborations that have particularly impacted your business?
Partnerships are what Plentyi is all about! Collaborating with local NYC garages is our biggest partnership to date. When we launched nine months ago, we started with smaller parking garages because we wanted to build trust in the parking industry and with homeowners. This partnership was eye-opening as I gained a better understanding and appreciation after realizing that many small garage owners started as parking attendants, worked their way up to managers, and eventually owned their garages. They are small businesses too, facing the same challenges and pain points as other entrepreneurs. That perspective has shaped how we approach our role in the industry, and we always keep our community first!
How do you handle competition, and what sets your business apart from others in your field?
I keep one eye on the competition and one eye on our vision. What sets Plentyi apart is our community-first approach. Other apps focus only on transactions. We go further — we educate our hosts on how to list and price their spaces, giving small businesses new revenue streams, and we reward drivers through our loyalty program.
We’re not just a parking app; we’re a conduit connecting drivers, homeowners, businesses, and event planners in ways that uplift everyone and help them find easy and affordable parking.
In a world full of trends, how do you keep your business authentic and true to your vision?
We stay grounded by listening to the community. Every time a family member, friend, or customer asks a question, makes a suggestion about our web app, we take it seriously because they are our community. We don’t want to copy others — we want to provide real solutions to real problems and make our customers’ lives easier.
Homeowners are worried about liability, small businesses are squeezed by rising costs, and drivers are tired of paying $600+ a month for garages. Sometimes pricing in the market is outside of our customers’ budgets, but we offset it with loyalty rewards, early-bird specials, and seasonal discounts. By addressing real struggles directly, we stay authentic. Our vision has always been simple: more time, more space, more opportunity.
Plentyi holds ourselves accountable to that vision, even when trends shift. The brand wants every customer to have an exceptional experience and walk away satisfied. We see Plentyi in people’s homes and businesses — not just on their maps.
What’s your go-to mantra or quote when the going gets tough?
“Remember why you are doing this.” I never want to lose sight of the reasoning behind the vision and mission. If I lose that, I risk becoming discouraged, doubtful, and giving up. There are nights when you lay in bed questioning yourself, the purpose of this business, and why you’re continuing — and in those moments, I remind myself: “Remember why you are doing this.” For me, it was never just about the money; it has always been about the people and our community. The Plentyi people.
Meet Andrea Geiger
Founder & CEO, Plentyi
Andrea Geiger is a Brooklyn-born entrepreneur, technologist, and community builder dedicated to bridging the gap between technology and urban communities. As the Founder and CEO of Plentyi — New York City’s on-demand parking platform — she connects drivers with unused parking spaces, turning underutilized spots into steady income for residents and small businesses while making parking more affordable and accessible.
Under Andrea’s leadership, Plentyi has expanded to include partnerships in EV charging infrastructure, revenue-sharing programs for local businesses, and smart parking solutions that integrate curb management, IoT technologies, and AI-powered innovations. The platform is a certified NYC Minority and Women-Owned Business Enterprise (MWBE) and is growing rapidly, enhancing its customer experience through white-glove service, strategic partnerships, and community-driven features. Beyond parking, Plentyi is committed to empowering its community through education — actively developing a curriculum for both youth and adults focused on technology, entrepreneurship, and AI.
Andrea’s career spans leadership roles in cybersecurity, IT risk management, and critical infrastructure protection for major transportation networks, federal agencies, and national organizations. She has developed cybersecurity programs for complex infrastructure, led enterprise-level threat, vulnerability, and risk assessments, and delivered innovative technology solutions that improve security and community access.
Guided by her belief in “Plentyi for Everyone” — representing plenty of money, time, space, and flexibility — Andrea is passionate about sharing her expertise and vision through speaking engagements, panel discussions, and collaborative forums that explore how technology can drive community growth and improve everyday life.
Thank you for reading, “Plentyi for Everyone: Andrea Geiger on Turning NYC’s Parking Problems into Community Power”, part of our mini-series. To read more amazing Q & A’s click here or check back next month.
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