Caroline Cummings

Caroline is a two-time technology entrepreneur. She's co-founded and held the CEO position for two internet companies, OsoEco (social bookmarking/shopping site) and RealLead (mobile marketing for the real estate industry). She's raised close to $1M in investment capital and has coached several other startups on their investor pitches. RealLead was recently acquired by IDX, Inc, and Caroline joined Palo Alto Software to lead their marketing and business development for the cloud-based business planning and management tool LivePlan. You can follow Caroline on Google+.

Recent Articles Published by Caroline Cummings

managing

How to Lose an Employee in 10 Days [Webinar Recap]

For our latest webinar, we discussed “How to Lose an Employee in 10 Days,” outlining major mistakes an entrepreneur or CEO should avoid if they want to hold onto valuable employees. I was joined in this webinar by Matt Rissell, the CEO of TSheets Time Tracking. If you’re not familiar with TSheets, they are a... Read more »

funding

5 Sure-fire Ways to Bomb Your Investor Pitch

Having delivered hundreds of pitches myself (and bombed a few), as well as coaching dozens of entrepreneurs on how to pitch, I’ve definitely seen some doozy pitches. I sometimes wish I’d had a video camera with me to create a funny compilation of all the bloopers—something I might have shared with entrepreneurs on how not... Read more »

funding

How to Impress Angel Investors and Make It into “Startup Heaven”

Ever wanted to ask an angel for advice? Now you can. Apart from a collection of tips direct from angel investors themselves, we're opening up our comment stream within this post. Got a question for one of the angels listed? Share it and they'll reply. Don't forget to use the hashtag #AngelTip on Twitter! Read more »

planning

How Big is Your Potential Market, Really?

Whether you’re a startup or an up-and-running business, you should know what your total potential market opportunity is for your products or services. I’ve coached many companies over the years, as well as judged several business plan competitions, and I’m always surprised by how most business owners can’t confidently tell you their total market potential.... Read more »

starting

How to Pick the Right Attorney For Your Startup

Picking the right attorney in your startup is as important as picking the right business partner. You can’t underestimate the importance of selecting an attorney who “gets” your business model, your market opportunity, and most importantly, your fundraising and exit strategy. Read more »

funding

How to Avoid Taking “Dumb Money” in Your Startup

You may think that when someone offers you money to fund your startup, you should find a way to take their money. But even more important than landing an investment offer is knowing when to say yes to investors and when to say, “Thanks, but no thanks.” Just because someone has money doesn’t mean they have... Read more »

managing

Ideas Make or Break Your Business

I don’t know about you, but I come up with a new idea every day. However, ideas without execution are merely thoughts in one’s own head. The writer Ralph Waldo Emerson said it best: “Ideas must work through the brains and arms of men, or they are no better than dreams.” Ideas are key to... Read more »

managing

How to Inspire Your Employees

Have you ever heard the following statement?: “If you want to build a ship, don’t drum up the men to gather wood, divide the work and give orders. Instead, teach them to yearn for the vast and endless sea.” It’s a quotation from the French writer Antoine de Saint-Exupéry, and Adam Bryant—The New York Times... Read more »

managing

Culture Eats Strategy For Breakfast

The New York Times' columnist Adam Bryant sums it up in his book by saying that “culture is the X factor that will determine who wins in the long run.” Read more »

managing

Top CEOs Reveal Their Secrets to Innovation and Growth [WEBINAR]

Join our free webinar with Adam Bryant, The New York Times bestselling author and “Corner Office” columnist, to learn the secrets of top CEOs and how your small business or startup can create a culture of innovation. Read more »

funding

9 Things That Take a Pitch From Good to Great

When I think about what set the excellent pitches I've seen apart from the rest, it turns out that they all shared some of the same qualities. Read more »

managing

Get Your Business in Shape in 2014

It's pretty funny, actually, how well weight loss and fitness advice translates to managing a business and "trimming the fat" out of your company's operations budget. Read more »

funding

My 13 Favorite Alternative Funding Options of 2013

Whether you’re a nonprofit, a new small business, a high-tech startup, or an up-and-running company, and whether you’re looking for a loan or a grant or an equity-sharing arrangement, there is an option for you. Read more »

planning

One Easy Trick to Get Your Business Plan Done in Under an Hour

Writer's block? It turns out that starting and finishing your business plan is a whole lot easier than you thought. Read more »

managing

Mentoring With LivePlan: Success Story

David Calderon, a California high school teacher, was the mentor to two of the BEC Boost competition's grand prize winners. I had the chance recently to ask David about his successful experience coaching his students. This is what he had to say. Read more »

funding

How to Make Your Gust Account Stand Out to Investors

These are my recommendations for how to help your company profile stand out on Gust, so you can successfully grab attention and raise capital. Read more »

managing

7 Interview Blunders and Bonuses

I’ve been interviewing several candidates over the last few months to fill positions on my marketing team at Palo Alto Software, and I am amazed at the number of people who show up for an interview unprepared. Some may say that it’s generational, but that’s not the case. I’ve interviewed candidates from seniors in college... Read more »

funding

The 10 Questions I Didn’t Expect to be Asked by Investors

If you're raising money for your company and you want to pitch to angel investors or venture capitalists, then there are a few important things to know that savvy investors care about. Read more »

managing

Slam Dunk Tips for Attracting and Keeping Fans

Everyone knows the value of word of mouth marketing. It’s a concept as old as dirt, but not something most businesses know how to embrace. The “social web” is a great avenue to allow the people that know and love you (aka, your “Fans”) to promote your business in a fun way. Fans are basically customer evangelists.... Read more »

funding

How to Pitch to Investors in 10 Minutes and Get Funded

Sometimes you only get 10 minutes to pitch your business opportunity to investors—this is a format I've successfully used and seen work for many other first-time start-up CEOs. Read more »