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Caroline CummingsCaroline Cummings

Caroline Cummings

An entrepreneur. A disruptor. An advocate. Caroline has been the CEO and co-founder of two tech startups—one failed and one she sold. She is passionate about helping other entrepreneurs realize their full potential and learn how to step outside of their comfort zones to catalyze their growth. Caroline is currently executive director of Oregon RAIN. She provides strategic leadership for the organization’s personnel, development, stakeholder relations, and community partnerships. In her dual role as the venture catalyst manager, Cummings oversees the execution of RAIN’s Rural Venture Catalyst programs. She provides outreach and support to small and rural communities; she coaches and mentors regional entrepreneurs, builds strategic local partnerships, and leads educational workshops.

Recent Articles Published by Caroline Cummings

funding

How to Successfully Pitch Your Business Idea to Investors

Sometimes you only get 10 minutes to pitch your business idea to investors—and here's a pitch format that will help you secure funding. Read more »

managing

The Importance of TAM, SAM, and SOM in Your Business Plan

TAM, SAM, and SOM, are vital parts of your business plan, but what do they mean? Here's a breakdown, plus how they apply to your business (plus examples). 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

9 Things That Take a Pitch From Good to Great

Only a handful of business pitches are truly great. What sets those excellent pitches apart from the rest? Here are nine things that stand-out pitches have in common, and how to employ them to take your pitch from good to great. Read more »

starting

39 Things to Ask Yourself Before Starting a Restaurant

This article is part of our Restaurant Business Startup Guide—a curated list of articles to help you plan, start, and grow your restaurant business! According to a study published in the Cornell Hospitality Quarterly, approximately 60 percent of restaurants fail within their first year of business. If you are dreaming of becoming a restaurateur, you can... Read more »

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. 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 »

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 »

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 »

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

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 »