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

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 »

growing

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 »

growing

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 »

growing

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 »

growing

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 »

growing

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 »

growing

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 »

growing

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 »

growing

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 »

growing

How to Align Life Goals with Business Goals: free webinar

Yesterday’s webinar enjoyed quite a crowd, and author Pamela Slim presented some truly thought provoking questions to help entrepreneurs align their life values with their business goals.   We recorded it in case you missed it! Read more »

planning

Boost your business with $10K

If you haven’t already – you should register your LivePlan business plan into the $10,000 Boost competition. It’s open to US residents. Watch the video below for some inspiration! We look forward to seeing your winning business plan! Also – register to attend the FREE live webinar on August 7th, 10am (Pacific Time) to learn... Read more »

growing

TAM, SAM and SOM – huh??

Having viewed several business plans over the years, a common (and very important) item missing from most plans is a breakdown of the company’s TAM, SAM and SOM in the marketing section of their plan. Wondering what these acronyms mean? Well you’re not alone – many entrepreneurs are not familiar with these terms. Here’s a... Read more »