February 23, 2023
 min read

Spotlight: Cara Whitehill ODA3


Avatar icon
Cara Whitehill


Avatar icon
Cara Whitehill
The post originally appeared on MikeWilner.com. It was republished with permission.

Avatar icon
Cara Whitehill


No items found.

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 instead 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.

Today, we’re highlighting one such donor: Cincinnati-based angel investor Cara Whitehill, whose extensive career in the travel industry included leadership at growth-stage startup Traxo and senior roles at Expedia, Travelocity, and Deem. She recently shifted to full-time angel investing and startup advising with Unlock Advisors.

We took the opportunity to speak with Cara about the impact of seeking out and supporting more opportunities for entrepreneurs from traditionally underrepresented backgrounds, and why unlocking talent lies at the intersection of global and hyper-local strategies.

What did you gain from participating in ODA3?

I wasn’t initially familiar with On Deck for the Angel Fellowship but had lived in the Bay Area for several years and had heard a lot about the Founders Fellowship.

I actually got scouted via cold outreach for the Angels program. I was still new to angel investing, only having done it on the side for the past couple of years. I thought the program was interesting and it really fit my career interests at that point—the nature and structure of the fellowship were malleable enough to balance with my other commitments. I was able to jump in and out, engaging in Slack and the other programmed events and recordings on my own time.

The breadth of the community I found particularly helpful as a newbie, because I was hungry for a framework around due diligence, finding deals, and handling inbound. That knowledge sharing from the folks who are a little more experienced was really beneficial for me. I received insight that helped me form the way that I want to approach deals and the types of founders that I want to back.

What is your thesis around angel investing?

With angel investing, you plant so many seeds and know it’s going to take several years for them to sprout. Impact is hard to measure, but I often think about it in two ways. One is to analyze the financial details. The second is to consider what kind of impact I can have with the founders and the teams that I'm backing.

I've worked in a couple of different startups, I know what that's like in the pre-seed and seed stage, where it can feel like you're wandering alone in the desert. Founders can feel that they have no support. I always thought, as soon as I’ve accumulated some capital, I want to jump in and be part of that, as more than just a check. I want to be a partner to these founders and help back them with my stories, my brainpower, and my battle scars. The things that I've learned along the way can help short-circuit some of the pitfalls that founders are likely to trip over early on.

In my angel activity, my first filter is whether it’s a problem I can help solve.  Next, I try to prioritize founders or teams who may be overlooked by other investors, whether that’s based on their backgrounds or because they are not geographically located in major tech hubs.

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

I love the concept. The reason I’ve shifted into angel investing is that I want to have a different type of return on where my dollars go. So one of the things I like about the Access Fund is that what would have been a standard tuition fee turned into a donation going toward another entrepreneurial-focused channel.

The startup ecosystem can be pretty insular, and for many folks outside that bubble, it can be difficult to find a way in. On Deck's effort to bring more talent from underrepresented backgrounds into the community really benefits both sides: it gives these founders a seat at the table so they can accelerate their growth both personally and professionally, while also benefiting the broader community with access to new and different ideas than they'd probably get to see otherwise. It's a win-win.

It’s also wonderful to receive the Access Fund Launch Report Updates, which give us statistics on where we’re parking our dollars. It's rewarding peering under the hood and seeing what kind of impact it’s having, particularly strengthening the connection between the Angels community and the Founders community.

Do you have specific areas of interest?

I'm involved with an angel collective here in Cincinnati called Queen City Angels (part of the Angel Capital Association), and I credit them with being super supportive of bringing in and skill sharing with newer investors like me.

There's a very strong emotion in these areas for getting local founders to think bigger. Venture capital is still evolving across the Midwest, so unlike in Silicon Valley, many founders here focus on bootstrapping as long as possible before considering the external investment. As a result, there are really strong ideas that don’t get the chance to scale as fast as they could.

By the same token, there is a lot of investor money in the Bay Area that could be put to great use outside of that bubble. I spent seven years in San Francisco and saw how narrow investors’ focus can be.

I’m passionate about using my “dual citizenship” to cross-pollinate ideas and relationships across these regions. Hopefully, these connections help drive some fantastic outcomes.

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

I’m interested in all the ways that broader access to community and distribution of opportunities is possible right now.

There is an intersection, for example with On Deck being global and digital, and the organizations using hyper-local, place-based strategies. I’m excited about a ‘both/ and combination’. That’s one positive outcome from the pandemic—we now have the tools and the frame of mind to be proximity-agnostic. Communities now can be simultaneously place-based (like OD Chapters) and place-unconstrained (with async tools like Slack). That shift has unlocked the power of what community can represent, making it easier for folks to tap into shared knowledge from literally anywhere, anytime.

More Access Fund Spotlights:

See more article

Inspired to donate?

Join a generous community of Fellows and Former Fellows who are demonstrating their commitment to access with action. Every dollar you donate will be matched by On Deck.