Rick Winfield

Business Owner

2023 - Current

I'm Working on my next project, not quite ready to announce yet.

Angel Investor

2003 - 2023

***I am not currently making new Investments. Please don't send me investment inquiries via LinkedIn*** I invest in and advise startups and am an LP in several funds and syndicates. My favorite areas to invest in include: Online Marketplaces, Artificial Intelligence, Consumer Goods, HRTech, RestaurantTech, PropTech, and the occasional B2B SaaS company. I like companies that create efficiencies around major life decisions like education, real estate, employment, and food. My most successful investment to date was a chocolate bar company.

Investment Committee Member

2019 - 2021

Professor of Entrepreneurship

2014 - 2020

I was a member of the faculty at Sierra Nevada College, a private liberal arts college on the north shore of Lake Tahoe. I designed and taught classes about Entrepreneurship, Digital Marketing, Entrepreneurial Finance, Corporate Finance, and Leadership. I was the faculty advisor for team LIMIT, a student business plan competition team that won over $70k in prize money (see more under projects).

Adjunct Professor of Entrepreneurship

2014 - 2015

I taught Special Topics in Entrepreneurship: Entrepreneurial Marketing at UNR and Small Business Marketing at Truckee Meadows Community College.

Founder & Director of Technology

2003 - 2013

Veskritec was a lead generation directory website incubator that assisted in the creation of four lead generation businesses: www.BeautySchoolsDirectory.com (sold 2007) www.ElderLivingSource.com (sold 2008) www.AllPropertyManagement.com (sold 2010) www.ManufacturedHomeSource.com We identified and recruited business founders, provided a website technology platform and business development consulting, and assisted with the sale of three of the four websites. We invested in each website using a unique revenue-based finance model and realized a >6X return on our investment over 7 years.

Founder

2001 - 2011

Caution Media, Inc. was the business entity under which I explored entrepreneurial ventures for 10 years. Our biggest success was ComputerTrainingSchools.com (see below).

Founder

2001 - 2006

Founded ComputerTrainingSchools.com, a pioneer in online .edu lead generation. Built the website technology, hired a sales team, developed SEO/SEM/affiliate marketing campaigns, and oversaw day to day operations of the business. Grew the business to annual revenue of $3M before successful sale to Quinstreet, Inc (NASDAQ: QNST) in December 2005.

CTO

1999 - 2000

Recruited by company founder to lead the technical team in building a content-focused online business. workz.com was a leading provider of online information for small businesses, rated as a top 10 small business site by Fortune, Forbes, and Inc. Magazines. I hired a team of seven and acted as the liaison between the technology team and the editorial and business development teams. We built in-house, highly scalable content management and email list management systems to host the content, control editorial workflow, support content syndication, and facilitate ad revenue schemas.

Web/Ecommerce Developer

1996 - 1999

Original employee hired to develop and maintain the website for a children's computer game company. I built interactive and social features as well as an online store that quickly made the web team "profitable." Developed online presence for Cavedog Entertainment, a new game studio started by Humongous. Recruited by Humongous' parent company to build a company-wide e-commerce system. Assisted in the recruiting and hiring of ten additional employees for the web and e-commerce teams.