20 years of bravely leading businesses across the Hudson Valley
Q+A with Lauree Ostrofsky
Lauree Ostrofsky is still scared but she’s doing it anyway. She’s introverted but she’s showing up and networking anyway – on her terms. In her 20s, she was diagnosed with a brain tumor, but not only did that not stop her, that motivated her: For the past 20 years, as a business and career strategist, Lauree has guided small businesses across the Hudson Valley, founding Hudson Valley Women in Business (HVWiB), a network of over 3,000 members around the region, serving as an executive coach for non-profit leaders with NYCON and consulting small businesses as they navigate loans through her initiative with the Rondout Savings Bank.
This week, Lauree will officially celebrate 20 years of helping others take the plunge with their business ideas and careers during a special event on Tuesday, September 29, 2026 from 10:30am to 12:30pm at CoWork Kingston, 8 North Front Street. There will be snacks, beverages, interactive activities and a ribbon cutting at 11am.
But before we get to cheer for Lauree on Tuesday, we caught up with her to reflect back on her work across the Hudson Valley over two decades:
Niki@HVNY: As you look back on your 20 years of shepherding others, how does it feel knowing you have guided so many others in their careers?
Lauree Ostrofsky: Thrilling. How lucky I’ve been to live vicariously through thousands of businesses and career paths different from my own, and to be witness to so many a-ha moments.
HVNY: How did having a brain tumor impact your path?
LO: It was a tremendous catalyst. When big things happen in your life — divorce, job loss, health scares, etc — they can wake you up to what’s really important. The next step though is yours to take. So I’ll say I took a lot of steps toward the way I live my life based on the giant wake-up call I had at 28 years old.
I realized first hand how precious life is and that being in the ICU is truly scary. Not the survivable "scary" things like speaking on stages, publishing books, starting a business, standing up for what you believe in, going first to say vulnerable things in relationships. I could be brave and do those things.
HVNY: What tips do you have for someone thinking about starting her own business?
LO: Don’t assume your business will immediately pay your bills. In other words, make sure you have a steady stream of income somewhere else first. Get a side job, keep your current one a little longer, fill your savings account, move in with family.
When you feel safe and secure, especially financially, you can be more creative and thoughtful about what you build. When your business needs to provide for your stability right away, it puts too much pressure on you and it. You need a runway to figure out how this new idea is going to work for you.
HVNY: You have said you’re a shy introvert — how does that impact not only running a business but consulting others?
LO: I share often how shy and introverted I am, because I want to remind others (and myself) that we can do things in ways that stay true to who we are. For instance, you don’t have to turn yourself into an extrovert to talk to people in a crowded room. When I’m networking, I take quiet time before and after to save up energy and I give myself a reasonable goal. Talk to three people, and then if it feels like enough I can leave.
HVNY: One of the mottos you share is “I’m scared & I’m doing it anyway” — what is something recently that you’ve been scared of doing and did it anyway?
LO: As a business owner, maker, writer, musician, entrepreneur in any sense of the word, pretty much every day has a scared & doing it anyway moment. It’s because so much of what we do is taking on a new challenge or question we hadn’t anticipated before, or proving to other people that what we’re doing is worth investing in / buying / telling other people about.
My biggest one in recent years was becoming a full time stepmom to two now-teenagers. I was scared on a daily basis that I’d mess up who they were becoming. But they needed to move in with my partner and I, that was so clear to me at the time, so every morning since I’ve had to wake up and figure it out all over again. The dinner when I told them I was scared and doing it anyway was actually the most liberating, because at least then they knew I was trying.
HVNY: Are there any local businesses you’re really cheering for lately?
LO: SO MANY. It’s my favorite past time to walk into a new business and tell the owner how excited I am for them. Right now, I’m loving my collaboration with Midtown Business Alliance serving small business owners and professionals working for themselves in midtown Kingston down the street from where I live. And of course the board and members of Hudson Valley Women in Business, my heart is always with them.
HVNY: Where are your favorite places to relax or find inspiration here in the Hudson Valley?
LO: I grew up in Dutchess County, so the grounds of the Vanderbilt Mansion are my favorite views in the region. I also love biking along the Ashokan Reservoir in Ulster County from the second or third entrances. It’s so quiet and still there.
Celebrate Lauree’s 20th anniversary in business on Tuesday, September 29, 2026 from 10:30 to 12:30pm at CoWork in Kingston. Details in the calendar and at https://www.eventbrite.com/e/20-years-of-career-business-leaping-tickets-1996517531682
Learn more about Lauree’s services at https://laureeostrofsky.com.
“When big things happen in your life — divorce, job loss, health scares, etc — they can wake you up to what’s really important. The next step though is yours to take. ”
"Simply Leap" is a happy how-to book sharing the seven lessons learned by Hudson Valley Women in Business founder Lauree Ostrofsky’s most-successful clients through the years.
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