Lauree Ostrofsky on Entrepreneurship, Community & Supporting Women Business Owners (Q&A) | Art of Business | Hudson Valley | Hudson Valley; Chronogram

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Lauree Ostrofsky on Entrepreneurship, Community & Supporting Women Business Owners (Q&A)

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After a mid-20s health scare shook up Lauree Ostrofsky's world, she turned her life inside out. She quit her job, moved cities, left her marriage, travelled around the world, and founded Simply Leap, a career coaching and consulting business.

Returning to her hometown of Hyde Park in 2014 after a six-month book tour and bumming around her parents' house for a few months, Ostrofsky realized she really needed to make some new friends. She knew she wanted to spend time with people who understood the life and grind of being a woman business owner. So she arranged a meet-up with four other local female entrepreneurs. After a successful evening of drinks, laughter, and commiseration, the group insisted on doing it again. And they haven't stopped.

That's how the Hudson Valley Women in Business community was born—with a standing monthly meet-up that's continued to gain members and momentum over the past four years. Recently, Ostrofsky shared her thoughts on the current climate for women business owners in the Hudson Valley and what it means to grow and support a diverse community of entrepreneurs.

Lauree Ostrofsky. - PHOTO: SWEET ALICE PHOTOGRAPHY
  • Photo: Sweet Alice Photography
  • Lauree Ostrofsky.

What's the origin story of Hudson Valley Women in Business?

Ostrofsky: The theory behind it is, "It's lonely trying to figure out things in your own head," because, as a business owner, it's on you. It's so nice being around other people who really get it, because they're experiencing that too.

And the level of honesty is different. We can really be like "OK, so this is hard," and there're these knowing laughs, but it's still supportive and positive at the same time.

You don't need to perform "Girl Boss-iness" for one another. You already know.

Right? We don't wallow, but it's like, alright, let's keep it real. That's a lot of what happens in our community: We ask a lot of questions. Not just for a referral to a great accountant or a lawyer or something, but also, "Hey, do you feel this way?" or "How do you manage when your kid gets sick and you still have to open your business?" We get to pose those questions.

Do you think that says something about how women operate generally? That sense of communication, community, and open sharing of information?

Yeah, absolutely. The philosophy behind our community is "women do business differently." Some of the ways I see that playing out in the community is that we're natural collaborators rather than competitors.

What are some of the specific challenges you're seeing among members of your community?

Nationwide, there aren't really systems in place to support women business owners who are moms, caregivers, and heads of households.

My members have mentioned that most people get into business ownership for the freedom and flexibility. Those two words come up so often when building a business. Like, "I want to work in the hours that makes sense for myself and my family and people in my life."

Hudson Valley Women in Business celebrating at Oak Vino Wine Bar in Beacon. - PHOTO: JACPFEF PHOTOGRAPHY
  • Photo: JacPfef Photography
  • Hudson Valley Women in Business celebrating at Oak Vino Wine Bar in Beacon.

But the thing that flexibility sometimes turns into—especially for mothers and heads of households—is "always on." So that's a reality of what it looks like to be a woman business owner.

How do you, as a community, support your marginalized members with challenging systemic privileges (e.g., the financial safety net needed to take risks in business)?

I think that the region itself could be better. Within our community, we're posting educational opportunities all the time. Whenever there's a program, a pitch competition, or some kind of educational thing, people are always sharing it, because the only way we're going to find out is by starting to spread the word within our communities.

The other thing is that Hudson Valley Women in Business collaborates with other organizations. We're always talking to other organizations to see what they're doing. We don't have to create all the programs ourselves; let's promote each other.

I reached out to a couple of people directly to ask specifically about trans and non-binary business owners to make sure that when we look at marginalized [community members], it's not just [cisgender] women. Who else are we hearing from within the community and what are the other needs and challenges that are there?

One queer business owner said to me, "I don't know any trans or non-binary business owners. If I can think of one, I'll let you know." And she said, "Maybe the fact that I don't know any and can't think of them, maybe that's the story." Because, again, we need to reach out into the community and say that this is possible.

How can community members be better allies to marginalized business owners?

I think that question says it all, which is to actually think about it—to think about who those business owners are, to think about the products and services that we're using, where they come from, and who's behind them.

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