February 23, 2023
 min read

Spotlight: Charles Oppenheimer ODA3


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Charles Oppenheimer


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Charles Oppenheimer
The post originally appeared on MikeWilner.com. It was republished with permission.

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Charles Oppenheimer


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At On Deck, we endeavor to build a digitally native and globally accessible community of ambitious builders of all backgrounds. We draw on our own ecosystem to unlock access for new talent to further enrich the potential of the community at large.

This mission is exemplified by the pay-it-forward model of the On Deck Angel Fellowship.

For Fellows joining ODA, an eight-week remote program that brings together angel investors seeking to increase their deal flow and tangibly improve the quality of their network, the tuition fee is actually a suggested donation to the Access Fund.

Each donation by an ODA Fellow serves to fund  two scholarships for qualifying participants of the On Deck Founders Fellowship. In addition, On Deck matches each donation generated by ODA fellows dollar-for-dollar as part of our pledge to match all donations up to $1M through 2021.

We are grateful to our ODA Fellows for their gifts, and we like to highlight their valuable contributions to our community whenever possible. One such donor is San Francisco-based angel investor Charles Oppenheimer, whose career experience included founding a startup, Prizzm, a social CRM platform for customer feedback, and nearly a decade of working at the senior level at Twilio.

We caught up with Charles to chat about his angel investing activity, the importance of looking for opportunities in developing countries to create more impact, and why strong networks can make all the difference in a founder’s chances of success.

What did you gain from participating in ODA3?

Charles: My ODA Fellowship came at this critical time during the pandemic isolation, and the social element of having access to a high-quality community while doing something business-related was really perfect.  

I had considered angel investing very much a side effort, lucking into some deals but kind of trying to avoid much of it. When I looked at On Deck I had been considering investing more and committing to my thesis of international investment in tech companies that increase credit and create property—along with API/software companies that is my professional focus.

I found in ODA an interesting mix of investors from different backgrounds, from total novices to professional investors, and it was great to mix it up with everybody. Even the idea of stating what my investment objectives are with ODA helped, along with the curriculum and some of the specific learnings and tools. Besides just learning from the other investors, it also significantly increased my deal flow by joining syndicates from several other ODA fellows. I became so familiar with syndicates from AngelList, for example, that I helped a group of API investors (mostly Twilio-based) start the 200ok syndicate- something they didn’t know about and I brought to the table.

The net effect of ODA has had the effect of me investing more. I'll tell you in 10 years whether that was valuable or costly—I'm cautiously optimistic.

What is your thesis around angel investing?

Charles: I am particularly drawn to tech-enabled businesses in developing markets like Africa and Latin America because I know their success can have an outsized impact. I studied international development in college and saw how it can famously backfire.  You can look at the dependency model where economies hope for more—and it doesn’t move the needle compared to a growing vibrant business that creates jobs and wealth. So I selectively invest in startups that are focused on changing systems, like increasing credit or property ownership.

A prime example is a company called Tugende in Uganda, which was technically my first angel investment back in 2012. Tugende has a program that facilitates loans for motorcycle taxi drivers, which they can then finance to own the asset. So after 18 months, these drivers are property owners where in many cases they had no assets before, and a higher income for the same work. Seven years later, they’ve just raised their Series A, and it’s been profitable the whole time while delivering impact. I was the first investor, and just love enabling the right companies by being the first in, with unsubstantiated hope and belief—the most satisfying part of angel investing especially if it is making the world a better place.

I have always worked for, started, and invested in software companies, most recently in the API category. My ideal investments are the combination of that, API companies in developing economies that create financial access or property. I have one in the pipeline I am super excited about, first money in again, that is going to go into fundraising mode soon. ODA helped me have the confidence to double down on what I believe in.

What was your reaction when you learned ODA Fellows support ODF Fellows through the Access Fund?

Charles: I knew there was a $5k fee going into ODA. When I heard that it goes directly to the Access Fund, I thought, “Okay. That's perfect.” It’s an excellent reason to do it. It wasn't just a fee, it was earmarked for improving access to underserved founders and investors. We work in a field with a known problem, where this same group has access to all the investments and startup capability, and not everybody else does. It fully mirrors my efforts to seek out underserved areas, like developing countries, and invest my resources there.

How important is a community in setting someone up for opportunities that impact their lives?

Charles: In effect, pretty vital. Thinking about strong networks, if you go through one of these programs, and this is the same pool of people that you reach out to when you need funding. Same for when you need co-founders, drawing on community has a huge effect.

People who don't come from traditional environments like Stanford or Harvard Business Schools have more access to it by being part of the On Deck community. And from my perspective, if I can help someone have opportunities, I will.

More Access Fund Spotlights:

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