Hi, I’m Howard.
I started my career on Wall Street at the turn of the century as an investment banker. However, it didn’t take long to realize I was more interested in building companies than analyzing or advising them. I moved into venture capital at VantagePoint Venture Partners, where I spent several years helping founders start, grow, and sometimes fix or salvage their VC-backed companies. That experience gave me a front-row seat to what actually makes businesses work — and what quietly kills them.
Eventually I stopped advising and started doing, and that’s what I’ve been up to the past 2 decades: I co-founded BrokersWeb, an insurance-focused online advertising marketplace that made the Inc. 500 twice before a successful exit, and then Healthcare.com, where I’ve spent the past decade building data-driven marketplaces and distribution platforms at the intersection of consumers, brokers, and health insurance carriers.
This blog is where I think out loud about healthcare markets, insurance, technology, and what genuine innovation in this industry actually looks like — along with the occasional detour into what it’s like to build a company and stay curious in New York City.
Work
Healthcare.com
Digital platform connecting millions of health insurance consumers with coverage through proprietary products and network of distributors and carriers.
Co-Founder → CEO → COO → CRO
Series A / B / C, $200M+ raised
Hard at work turning this into a big company & exit for shareholders
ContactUs.com
Customer acquisition SaaS tool. Better contact forms for better lead capture and post-lead marketing automation.
Co-Founder (2012–2015)
Bite-sized acquisition by WorkWave in 2015
MedicareSupplement.com
Started as a JV with one of the largest Medicare Supplement distributors in the country to build a digital customer acquisition engine for MedSupp enrollment. Eventually acquired by JV partner.
Co-Founder (2013)
Bite-sized exit for PeopleFund
BrokersWeb
Leading customer acquisition platform for P&C and Health Insurance reaching $100M in revenue.
Co-Founder & COO (2007–2012)
Successful exit in 2012
VantagePoint Capital Partners
Multi-stage, multi-billion dollar VC fund.
Associate → VP (2003–2007)
Great learning experience. Met great founders and people along the way who 20 years later have done awesome things
Merrill Lynch
Investment Banking Group, Global Media Group.
Investment Banking Analyst (2000–2003)
Beyond the financial, learned how to compress timelines, push for near-term outcomes, and work alongside high-potential, hard-working individuals.
Education
Wharton School, University of Pennsylvania
Finance — Class of 2000
English minor from the College of Arts & Sciences