Caroline Cummings: Startup Lessons from Failures

We chatted with Caroline Cummings, serial entrepreneur and VP of Marketing at Palo Alto Software, over a G+ hangout last week. It was a great conversation and Caroline shared some very useful tips for entrepreneurs that are lessons from failures.

Caroline Cummings started her career in corporate America and decided that a 40,000 employee organization was not for her. Even while in the corporate world, Caroline built a foundation working as an “intrapreneur” within her organization, learning all about writing a business plan for new products, seeking funding and developing a market for her project.

After her move to the west coast, she wanted to pursue her passion in sustainability and entrepreneurship. As the former co-founder and CEO of two technology companies, she’s experienced both start-up failures and successes, and has raised close to $1 million in investment capital.Her first venture, (healthy social shopping), dissolved in 2009. Her second venture, RealLead (mobile marketing for real estate) sold in early 2012.

While talking about her startup experiences, Caroline wants to stress on the lessons she learned:

  • A wrong team just won’t work: Caroline says this is the biggest reason that startups fail. A lot of times cofounders have a similar backgrounds and diversity is key. This also extends to choosing the right legal and finance team.
  • If you cannot measure it don’t make it: Caroline is a big believer in metrics and measurement. Measurement helps companies engage better and react to their customers. Think about the Key Performance Indicators (KPI’s) for your business? Include them into your business plan software like LivePlan and work towards it. Measurement should not be an afterthought.
  • Don’t stay stealth too long: Another reason startups fail is because they stay stealth too long, either because they do not want to hurt their IP or they think they are not ready to launch. Caroline recommends entrepreneurs to share your plan with trusted mentors and launch lean and fast.

Caroline is a big proponent of mentorship. She says, “Take the advice of the people you trust and bounce ideas off of them.” Caroline currently mentors several young women and is also the immediate past president of the Big Brothers Big Sisters of Lane County’s board of directors.

Listen to the entire talk here:



About the Author

Hi there! I am Priti and I specialize in strategy and communications for impact organizations that aim to create social, environmental and economic wealth for all stakeholders. Working from the ground up, I help these do-gooders craft effective programs for community engagement, outreach and profitability. Follow my work covering do-gooders, cleanweb, start-ups and Web 2.0 businesses on Ecopreneurist and at Crowdsourcing Week. I enjoy traveling with my boys, cooking up a gourmet meal from scratch and entertaining! Join my community for Social Entrepreneurs on G+ Follow me on Twitter, on LinkedIn and Google+