Portfolio Companies

I focus on early stage investments primarily located in the Washington, DC Metro area. I sometimes invest as an individual or occasionally lead rounds where I syndicate the deal with other investors. I limit my activity to 3-5 new deals per year. I typically sit on the boards of my portfolio companies. Range of investment varies with the opportunity and stage of the company. Historically we have invested individually or as a group between 50k-1million in first rounds. I tend to co invest with other experienced angels or early stage venture funds. My goal is an accelerated exit for both investors and entrepreneurs. I take a portfolio approach to investing trying to equally divide my interests between the following:

1. Venture returns of 3-5 times in 3-5 years.
2. More mature businesses with cash flow predictability (ie. Five Guys Franchises) (Potentially held for long term).
3. Swing for the fences. Companies that show potential for 10x returns. Higher risk – higher reward.

Submit Your Plan:

If you have a business that meets one of the categories listed above, I would invite you to submit a one page executive summary to cal@calsimmons.com

To get a feeling for the types of companies I have invested in previously, see the portfolio companies listed below.

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  Nationally famous hamburger joint started in Alexandria, Virginia. Investor in parent company as well as franchises in Arkansas and Tennessee.
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  Provides education technology platform to teach, assess, and certify students in financial literacy, loan management, and more
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  Innovative new pizza franchise originating in Atlanta, GA. Customers build their own pizzas & salads, assembly-line style.
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  Offers feature content and deeper analysis of industry trends and major events.
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  Developer of Skylight, a software platform that companies use to create smart glasses applications for business scenarios who wants to transform their operations using next generation wearable devices
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  National security technology company that delivers innovative systems, solutions and services in support of mission-critical initiatives on behalf of the Intelligence Community, Department of Defense, Department of Homeland Security, Department of Justice, and Department of State.
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  Provides interactive audio advertising for Internet radio stations, that connects consumers with brands through mobile audio apps.
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  Private biotechnology company that uses proprietary cell culture technology to develop cell therapies to treat insulin-dependent diabetes.
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  Technology company which has pioneered a model for combining big data and psychographic survey studies to develop a sophisticated understanding of consumer motivations, values, attitudes and beliefs.
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  The leading provider of cloud-based social and customer engagement solutions that empower organizations to deliver more efficient and effective customer service and support across more channels including social media.
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  Revinate is a software platform designed exclusively for the hospitality industry that makes it easy to take control of your online reputation by using online reviews and social media to learn from and connect with travelers.
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  A premier online travel agency for luxury hotels worldwide.
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  A website dedicated to providing the best travel contests, deals, and blogs in an easy-to-access format.
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  Bank centered and primarily located in the D.C. Metropolitan area.
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  Provide political strategy, global and local in-district campaigns, interactive services, outreach, grassroots technology, PAC compliance, and government services. DDCA serves corporations, associations, and non-profit organizations in different industries such as energy, managed care and defense.
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  The Distributed Solar NetworkTM is Distributed Sun’s (D-Sun) program to partner with EPCs and developers to finance construction-ready projects, co-develop early-stage projects, or acquire qualified projects.
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  Guest relationship marketing for restaurants.
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  Offers personalized destination recommendations in an intuitive format powered by expert travel guidebook authors’ advice.
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  Aspire Lifestyles - strategically integrated concierge, personal assistance and customer relationship engagement services.
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  Beer brewing company founded in Ashburn, Virginia.
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  Provides organic, easy to make meals for kids. Available in 3,000 stores across the country including Whole Foods, Sam's Club, Harris Teeter, and may more.
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  The hot new way to rate today's fashion trends and get advice on yours. Upload yourself wearing any outfit and see if others around the world share your style.
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  Helps travelers maximize their number of travel points.
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  Social Toaster helps you engage your fans and makes sharing your content over their social networks easy.
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  Zero emission commercial electric vehicles.
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  Easy to use cloud-based database.
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  The Zignal Labs solution embodies the logical evolution of the traditional communications war room by capturing thousands of content sources in real time including news articles, blogs, tweets, public Facebook posts, and social videos.