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

Skye, appreciate you joining us today. We’d love to have you retell us the story behind how you came up with the idea for your business, I think our audience would really enjoy hearing the backstory.

I spent most of my career working in New York government relations, as a lobbyist, political consultant and on political campaigns. After serving as regional director on the Mike Bloomberg presidential campaign, which ended on March 4, 2020…. COVID shut down New York on March 13, 2020… so I was suddenly unemployed and locked inside. Not having anything else to do, I turned to Instagram, and contacted my friends in elected office, asking them to join me on Zoom for a 10-minute recorded interview I’d post on Instagram for a show I started called, “Life Before the Virus,” to document how their lives and jobs were changing in real time in March and April of 2020 throughout New York. In just two months, I had 70 episodes, including episodes with then-Lieutenant Governor Kathy Hochul (who is now Governor of New York State) and then-Brooklyn Borough President Eric Adams (who is now Mayor of New York City), along with dozens of other high-profile figures in New York politics. People were reaching out to me to be on my show. I thought, “how can I make money doing this?” so I decided to pitch the show idea to local newspaper companies. I said “no one is leaving their homes to pick up a copy of your paper. Hire me, and these are the types of people I can bring to your audience online.” I worked with a Long Island local newspaper group and conducted a webinar series for them, bringing not only electeds to the screen, but also experts and stakeholders from all industries – real estate, education, hospitality, healthcare, etc. – talking about how COVID was impacting their day-to-day functions. When 2021 rolled around, and we were still deep in the pandemic, I knew there were so many changes about to happen in New York City politics – we were about to get an entirely new City Council, Borough Presidents, District Attorneys, a new Mayor… so I spoke with a New York City-based media company and pitched the idea of interviewing on zoom every single person running for elected office, so voters could meet the candidates without leaving the house, and vice versa. Candidates weren’t getting their names out there doing campaign events or fundraisers or attending any networking events, parties or industry functions. So beginning in 2021, I conducted 450 zoom interviews with every single person running for elected office in New York City, for a second media company, which propelled my name recognition to anyone voting in local elections. I was then approached by a third media company, where I am now: City & State, which offered to hire me in 2022 to bring this concept to their audience, and as the world opened back up, I could do these interviews in-person. While this was all happening during the pandemic, it’s important to keep in mind what a politically partisan place our country grew into. This was a time when Trump was president, when Black Lives Matter protests broke out in cities across America, and all kinds of young people decided to run for office. The national political rhetoric was completely polarized, and my cute, fun “get to know you” style interviews entertained players on both sides of the aisle, and further expanded into interviews with not just public officials, but to all kinds of high level leaders who wanted to share their stories of how they came into power, and what they’re doing to adjust to our new normal.
My current show, Political Personalities with Skye, is known to humanize elected officials and community leaders so that we can get to know them outside of their places of work, with the hope that collaboration takes place – and it has. I’m not only doing one-on-one interviews, but I’m able to mix public sector and private sector individuals to have constructive conversations about heavy issues impacting the lives of all New Yorkers, Long Islanders and New York City residents. The media platform has lent itself to opportunities for me to host various events, industry summits and private dinners – even hosting a red carpet at a major hotel opening in Times Square, where yes, celebrities attract media attention and fanfare, but it’s our public officials who helped physically zone, permit and vote on its erection – where I’m facilitating relationships both across the aisle and across the public and private sectors.
It turns out, our elected officials are not experts on every topic – they need industry to come to the table and share community challenges – that’s how they’re steered into good governance. It’s a team effort, with all eyes on New York. To succeed, there’s no room for partisan attitudes.
One of the biggest complaints you hear from most people is that mainstream news commonly highlights the negative – and with controversial political figures at the helm, there comes a ton of opinionated media. Instead of giving my opinion or bias, I allow my subjects to explain themselves – their thoughts, where they come from, what they’re passionate about – and when people are open, honest and candid about their goals and desires, we can work together more easily.

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers

I’ve always been a people person. I received a full academic scholarship to attend the University of Miami, where I studied medicine. The president of the school was Donna Shalala, known as President Bill Clinton’s Secretary of Health and Human Services during his administration. She taught a course during college about health policy and brought President Clinton in as a guest speaker. It was in that moment I decided not to pursue medical school, but instead to pursue a career in health policy. I graduated college a year early, and came back to Long Island to get my master’s in public health which turned into a second master’s in public policy. At age 22 with two master’s degrees, I decided I wanted to “fun” internship before diving into my career. I interned at News 12 Long Island – a local broadcast station near my parents’ home – and was assigned a story covering a guy running for local office. I didn’t know anything about politics, but in doing the story, I realized I really like this guy… so I reached out to his campaign to learn more. He ended up bringing me on the campaign trail, going everywhere throughout the county and meeting with a variety of stakeholders across Long Island. He lost his election that year, but some of the people I met along the way offered me a job. And that’s how my career in politics began, which continued for eight years. Since the pandemic began and I pivoted to working in media, I’m able to showcase more detailed stories than are commonly broadcast on cable news. Stories that have political undertones or government goals – and shine light on all the moving parts and partners in bringing local legislation or regulations to fruition. In our lifetime, and with the help of social media, we’ve seen politics become more accessible. It seems as if everyone is an advocate for something. People are more aware of elected officials. On a national level, our country is super divided and partisan… but on a local level, people must understand that it takes both Republicans and Democrats to get things done. Sitting out of voting isn’t an option… and the more communication we have, the more successful we will be at moving forward.
From personal experience, I believe the best way to enter politics is on the personal or human side. By showcasing who people are behind their fancy titles, I am humanizing our leaders, and fostering public-private partnerships, friendships and business relationships. It’s what’s necessary to accomplish our goals, as a town, city or nation, and if we can share a laugh along the way, or bond over our family dynamics, pets, sports or hobbies – it helps.

What do you think helped you build your reputation within your market?

By working with a series of local media outlets, I’ve been able to build name recognition and brand awareness in the New York local media market for those following state and city politics. When I show up in-person, people frequently comment on my keen sense of style – and it’s something I’ve been able to lean into to help create my unique brand and be recognized as someone fashionable, friendly and fun, who works in politics. It’s entertaining to me, as I’ve never touted my fashion sense before. It feels too innate to me to consider it a talent… it’s simply just the way I dress. But if the people like it, might as well make it part of the brand! I’ve been able to bring a red carpet concept to political events where high-level officials are being honored – I often say our public officials are the celebrities we should be following and knowing, instead of some of the more widely known reality TV show celebrities out there. These are the people weighing in on legislation and making the world change! Why not offer them the mic at red carpet events?

I met a New York State Assemblyman who shared with me that he spent 15 years as a sanitation worker – i.e. garbage man – before being elected. I said, let me put on the sanitation outfit and ride the truck with you! We filmed an awesome episode, and not only did I re-wear the outfit for Halloween… but I also wore the trousers (with a matching neon orange blazer) when emceeing a summit event for 300 people who were shocked that my stylish pants were actually a municipal uniform.

Another way I’ve been able to build fashion into my brand is that I now have what’s become my “signature earrings.” When conducting 450 zoom interviews from my apartment during the pandemic, my interviewees began to point out the one accessory you could see during a zoom interview: my earrings. They’re pearl hoops I wore during most of the interviews, and not only do I continue to wear them constantly, but I sell them on Instagram as my signature earrings.

We’d love to hear about how you keep in touch with clients.

Sounds cliche, but by keeping honest, and putting myself out there. I am known to make politics fun and engaging. In March 2022, I noticed several New York City elected officials were posting about basketball on Twitter. I tagged a few of them in one tweet, asking if the four of them have ever played together, and the answer was no. I reached out to them individually, one of them, New York City Council Member Kevin Riley, from the Bronx, shared that he plays at the Northeast Bronx YMCA regularly, and connected me with the facility. We spoke, and decided to host a “Political Madness Basketball Tournament” where elected officials were invited to play ball with each other, and we invited the community to participate as well. This collaboration caught the attention of the New York Knicks who sent an alum to the courts. While watching our public officials on the court, he said to me, that he watches a lot of people play ball, and you can tell a lot about a person by their sportsmanship. Ha! That was basically the purpose of the event – besides for raising money for charity – it was to get public officials together recreationally, outside the legislative chambers, to interact and build relationships. It proved my thesis correct: the more we get to know each other outside of our professions, the better our working relationships will be. And that’s true in politics – regardless of party affiliation. I’m proud to share that we’ll be hosting the second annual March Political Madness Basketball Tournament in partnership with the YMCA in 2023 as well. To me, it’s my creative, out-of-the-box thinking that has created “brand loyalty” and fostered partnerships and client relationships. I’m also planning a Fall 2023 Fashion Show, whereby elected officials will model the runway wearing designers from their districts, as a community engagement show to elevate local designers and the local leaders who represent them. Across the aisle, and on the aisle.

Contact Info:

• Website: https://www.cityandstateny.com/topic/political-personalities-skye/
• Instagram: https://www.instagram.com/thepoliticalpersonality_/
• Linkedin: https://www.linkedin.com/in/skyeostreicher/
• Twitter: https://twitter.com/SkyeStats
• Youtube: https://www.youtube.com/@CityandStateNY