David Pachkofsky is a serial entrepreneur, mentor, and angel investor whose entrepreneurial journey started at the age of 15. With an impressive track record of founding 16 companies and three successful exits, David is currently focused on his most meaningful venture to date—Dapper Care, a healthcare innovation company. His personal experiences, deep-rooted family legacy in business, and unwavering belief in purposeful entrepreneurship drive his mission to create lasting impact.
What sparked your entrepreneurial journey?
Entrepreneurship runs deep in my family. My grandfather, who started with nothing after the war, became a successful entrepreneur by building his own businesses, starting with a butcher shop. Both my parents and even my brother have been entrepreneurs, so I guess you could say it’s in my DNA. I started my first company at 15, and I’ve founded 16 companies since. My family’s journey, especially my grandfather’s, has been my biggest inspiration.
What were the key challenges you faced as an entrepreneur?
Staying motivated and focused has always been the biggest challenge. Entrepreneurship is a rollercoaster of highs and lows, and it can feel lonely at times. You have to be your own motivator, especially when things get tough. Self-discipline and perseverance are absolutely essential to keep moving forward.
What has been your proudest moment so far?
My proudest accomplishment is definitely Dapper Care, my latest venture. It’s my legacy project—the one I’m putting everything into. I’ve self-funded most of my companies, and with Dapper, I’ve invested around $400,000 of my own capital. We’ve come a long way—we have Amazon as an investor, and the founder of Apttus from Salesforce is our lead investor. After losing my brother to brain cancer, I pledged to invest half my wealth into startups fighting cancer. Dapper is more than a company to me—it’s about making a real difference.
What are your thoughts on women in leadership today?
I think it’s incredible and inspiring to see more women breaking barriers in business. My mom ran an advertising agency for 37 years, so I’ve always seen women in leadership. But I know how tough it is to be an entrepreneur—and being a female founder adds even more challenges. Women who are doing it deserve tremendous respect because the journey isn’t easy.
What advice would you share with aspiring women leaders and entrepreneurs?
My biggest piece of advice is—don’t try to know everything. Surround yourself with people who are smarter than you in areas you’re not an expert in. Your network is everything; it opens doors you didn’t even know existed. Let your team shine—hire people you trust, let them do their jobs, and don’t micromanage. Success comes from collaboration, not ego.
How do you define success, both personally and professionally?
If you’re an entrepreneur just for the money, you’re doing it wrong—and chances are you’ll fail. You have to be passionate about what you’re building, and if your heart is in the right place, success—financial or otherwise—will follow. For me, success is building a company that makes a real impact on the world.
“True success isn’t about money—it’s about passion, purpose, and the positive change you leave behind.”
Connect with David Pachkofsky:
https://www.linkedin.com/in/davidpachkofsky/
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