February Member Spotlight featuring True Wealth Ventures’ Kerry Rupp

 In Member Spotlight

Kerry Rupp is General Partner at True Wealth Ventures, an early-stage VC fund investing in women-led businesses in consumer health and sustainability. She also teaches for NSF I-Corps, helping university-based research teams identify commercialization opportunities, and sits on the Texas Health Catalyst Advisory Panel at Dell Medical School.  She serves on 3 company boards, and one non-profit.
 
Previously, Kerry was CEO at DreamIt, a Top Ten US startup accelerator and VC fund. She was founder/CEO of travel company Holiday Golightly and held VP positions at AllRecipes.com, Jobster, Classmates.com, and LexisNexis.  Kerry graduated from Duke and Harvard Business School.

How did you begin your career in venture capital? Have you always been interested in investing?

Perhaps surprisingly, it wasn’t an intentional foray into venture capital as a career – but came about as a solution to a business opportunity we saw in the market.  I was running one of the first startup accelerators (DreamIt), and we built a system where we had unique deal flow. While coaching startups during the program, we developed great insight into which companies would likely perform well.  Meanwhile, the companies needed funding.  So like a startup ourselves, we researched the market opportunity and ended up building a venture capital fund, because that was the tool that best met the needs of all the constituents.
 
If you’d asked me before I became a VC if I were interested in investing, I would have said no, because I would have likely associated “investing” with the stock market, and therefore financial ratios, S-1s and quarterly earnings calls.  But early-stage investing is about strategy, team, and intriguing new technological or business model innovations – and frankly not much that you’d consider traditional “finance” at all. 
 
If you could travel back in time to when you first got involved in venture capital, what is one piece of advice you would give yourself?

Well, I wouldn’t say that it ultimately held us back, but it took us a while to realize the importance of women investing in women… and I want to encourage more of that, so I’ll share it with others now.
 
When we started fundraising for the first True Wealth Ventures fund, we were mostly concerned with raising capital to get it to women entrepreneurs (as women CEOs are only receiving about 2% of venture capital dollars, even while women-led teams show outsized financial performance relative to all-male teams!)  So we weren’t particularly focused on raising funds from women (and in fact had been told that women were more risk-averse, and that wealthy women were perhaps more focused on philanthropy than investing, so they wouldn’t be good targets). 

Yet, when we did our first close on the fund, more than 50% of our investors were women (note: we counted couples or family offices where a woman made the investment decision in this category, but not other couples or families).  And then those women started inviting their friends to hear about the investment opportunity, as they realized they had both been those successful women in the workforce and had worked with them – and thought “if not us, who?” (given the weak performance to-date of existing, mostly male, investors in supporting women entrepreneurs).  So by the time we did the final close on Fund I, 80% of our investors were women – a statistic unheard of in venture capital to-date.  And with women apparently growing to controlling 2/3 of US investible assets by 2030, we think it’s a strategic imperative for the country that we get those women investing in innovation, in order to stay competitive!  
 
As a seasoned board member, what recommendations do you have for WBL members interested in serving on the boards of early-stage companies? What’s the best way for a senior executive to get involved with and learn about the startup community?

I think it’s always important to make sure you match your goals for board service with the type of board you should join.  So understanding what early-stage board service is really about is important.  Early-stage company boards are quite small, and usually originally consist of a few founders and the investors in the company, who may not have deep industry expertise and networks. They’re sometimes more generalist investors with value startup experience, but not healthcare expertise. 

As such, a company will value an outside board member who can bring knowledge of how things really get done within healthcare organizations and who can bring introductions from their network.  And at an early-stage company, those needs are often tactical – like helping secure a first pilot, or generating the first paying customer. They’re expecting you to get hands-on and really open doors for them. So it will probably be a better fit if your experience and networks are closely tied to the market segment or condition that the company is addressing (though it’s not a requirement).  Note that the company will also get credibility from the brand you bring from the employers where you’ve worked, especially if they’re leaders in their sector (and therefore possible future acquirers).
 
In terms of sourcing opportunities, you will want to get on the radar of the startups as someone who has knowledge and connections that they would really value.  A good way to both see deals and also establish your value is to volunteer as a mentor at accelerators or co-working spaces, either in your local community or virtually (via phone/video office hours), perhaps with programs that are more industry specific.  Another angle is getting to know VC firms who invest in a sector of interest to you and sharing with them your background and what you could bring to their companies’ boards. 
 
You’ll be moderating a panel at the upcoming WBL Summit featuring the founders and CEOs of innovative health care startups. What do we have to look forward to during your session?

Well, one of the most fun parts of my job is learning about totally different industries, and new science or technology innovations every day.  And so the audience will get a taste of that by hearing from the startups about the problems or opportunities they’ve identified in their markets, and their proposed solutions.  But they’ll also learn about the often unique challenges that startups face in staying alive long enough to get to market – especially in the healthcare industry, where there are so many different constituents, often with long timelines and strict processes, on top of regulatory hurdles, etc. My goal will be for audience members to resonate with a company or two and identify ways they can open doors or otherwise facilitate the startups overcoming some of these hurdles, by connecting them in the right way to their organizations.
 
Personally or professionally, what might the WBL network be surprised to know about you?

I love to travel and have visited all 50 US states and over 50 countries around the world.

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