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Caroline's Holiday

January 22, 2014

Caroline Cummings isn’t comfortable unless she is uncomfortable. And that’s just fine by her.

Remember the scene in the 1953 classic Roman Holiday where a royally repressed Princess Anne (Audrey Hepburn) seizes the handlebars of that iconic Vespa? In two spectacular seconds her eyes animate the full breadth of human emotion — from dread to anxiety to joy. She revs it; feels it quiver and pop into gear. And as she thrusts forward, she lets out a cathartic welp! When Joe Bradley (Gregory Peck) jumps on and attempts to take over, she says “No!” But what she’s really saying is “Yes!” This isn’t fear. It’s bliss…

Caroline Cummings ‘01 simply adores Roman Holiday — and Audrey Hepburn, too. Sometimes, when she’s mentoring or pitching an idea to investors, she deliberately channels Audrey. There’s Audrey the elegant actress and Audrey the gracious UNICEF ambassador. And then there is Roman Holiday Audrey: the blossoming star. Caroline loves that the film was Hepburn’s coming out — and that she nabbed the Oscar for her first major role. The theme is more important than any scene, though. It’s about getting out of your comfort zone, she says. It’s those daily reminders of just how vast the world is — and how sometimes you need to push yourself to find your place.

Caroline Cummings didn’t find success on day one, but she’s earned herself royal status within Oregon’s startup community. And she has accrued enough cathartic moments to make Princess Anne jealous.

“My Roman Holiday breaking out was going to Drexel,”

Cue the opening credits. We fade in on a tomboy — the kind of girl who actually pretended to be her brother to win a BMX bike race — standing on a sidewalk in Mays Landing, N.J., a town not far from the boards of Atlantic City where Caroline will one day labor. Caroline is 9 years old, and she’s hustling her neighborhood friends on the sidewalk. The prize? Baseball cards. The collateral? Doritos.

“You had to know the market and know your audience,” she remembers. “I knew that Brooke down the street wanted Doritos, so I dangled my snacks as the carrot. We were dealing, and it felt great. We didn’t realize we were doing business. But I got my Mike Schmidt and Pete Rose cards.”

OK. Now is a good time to let you in on a secret: Today, Caroline Cummings might very well be the most charming woman in the world. She’s classically beautiful — and there is even a hint of Hepburn in her features. But her lure is her voice. The way she talks. How she puts you at ease with tone and timbre. “Sit down,” she’ll say. “Relax. Let me get you some coffee.” And she means it. She wants you to relax. Talk to her for five minutes and you’ll feel like you’ve known her for a decade. Spend an afternoon with her and she’ll send you a care package of wine. So imagine her at age 9: Pygmalion’s uncarved Galatea. All talk, none of the polish she will one day radiate. She might have been armed with snacks, but her mind did the dealing. Caroline Cummings speaks headlines. She makes idioms like the rest of us make carbon dioxide.

Here’s one: “Life comes down to three things,” she says. “Knowing when to take an opportunity that comes your way, knowing when to pass on an opportunity and knowing when to offer one.”

The minute she says it, you think you’ve heard it before. Caroline leans back, watches you digest her words. Because she knows she’s got you. She just grabbed an opportunity and ran with it. And you can either eat her dust or hop on that Vespa. Because it’s going to be one hell of a ride.

In 2008, Caroline stood alone on a stage in Portland’s Governor Hotel and persuaded more than 400 angel investors to award her fledgling startup, OsoEco — a social networking community for sharing green products and services — $57,000 in seed capital. That’s right: Caroline Cummings talked her way to victory in the annual Angel Oregon competition held by the Oregon Entrepreneurs Network — the largest conference of its kind in the Pacific Northwest. And she did it pitching an app that didn’t even exist yet — with nothing to show but wireframes and screenshots. OsoEco had already raised more than $400,000, though. She was dealing.

Caroline had moved to Eugene, Oregon, with her husband, James, four years earlier, and it had taken years of false starts and hard-knocks to get to this point. She was unemployed for the first time since her early teens and hungry to make her mark as an entrepreneur.

So she volunteered. She mentored with Big Brothers Big Sisters of Lane County (she still does and is a past-president of their board of directors). She networked with entrepreneurs and even solicited the advice of a change management expert from the University of Oregon. Soon, she ditched her Philly business suits for jeans and paved her own way.

“You have to go get it,” she says. “When people ask me the definition of entrepreneur, I say it’s two things: Making something from nothing and being comfortable being uncomfortable most of the time.”

By 2008, Caroline was gloriously uncomfortable. She had become an influential voice among Oregonian entrepreneurs — and she did it by remaining humble enough to ask for help, while believing so thoroughly in herself that she inspired others to follow her lead. She co-founded SmartUps, a group of entrepreneurs, investors, service providers, mentors and community leaders who meet regularly for Pub-Talks to pitch new ideas. She has since gifted SmartUps to the Eugene Area Chamber of Commerce. She also created the Southern Willamette Angel Network, a group of investors who meet regularly to review emerging growth business plans.

At its height in 2009, OsoEco, which strove to be an eco-friendly Pinterest years before pinning was in vogue, had six employees — with Caroline at the helm as CEO.

“I knew I was doing something right because I was scared to death,” Caroline remembers.

But OsoEco failed. And it hurt. Caroline immediately entered into a two-year period during which she became a self-described “entrepreneur in recovery.”

“We don’t want to say failure,” she says. “We don’t want to say the F word. And in our culture, we think melancholy is a bad thing. But I think it’s more important to have and embrace those moments of melancholy.”

So she called other CEOs and asked them why she failed. And she found out. Chalk it up to due diligence and importance of forming the right extended team. Or, as Caroline says: “If you need to be a BMW, don’t be a Toyota.”

“Through self exploration I discovered all the things we did wrong,” she says. “But I also discovered what we did right. And I realized from the help of others that I want to be that kind of mentor who can provide other people like me with similar advice moving forward.”

During her recovery period, Caroline started her own consulting agency and was hired by the Eugene Area Chamber of Commerce and the Oregon Entrepreneurs Network to start new entrepreneurial programs and angel investor groups. She circulated a presentation called “the Top 10 Reasons Why Startups Fail” — which she hopes to one day adapt into a book called The Power of the F Word.

With Caroline’s growth, so grew Eugene’s startup community. She willed it with her Pub-Talks. And she knew she was on the right track because she was scared every day. Investors took notice. Behind closed doors they told her: “Let me know about your next gig, because I. Will. Fund. You.”

Caroline’s second venture, RealLead, a mobile marketing application for real estate that uses QR code technology to capture authentic, quantifiable leads for realtors, sold to IDX Broker in early 2012.

The operation, which Caroline co-founded, was set specifically to scale quickly for acquisition. It was a marvelous moment. Caroline hasn’t looked back since.

In 1999, a 29-year-old Caroline Cummings came to Drexel as a nontraditional freshman. She had already attended the Art Institute of Philadelphia out of high school, as well as community college — followed by a five-year hiatus during which she worked the casino floors, retail stores and restaurants in Atlantic City. She grew up working class, but she was ready for a different set of lapels.

“My Roman Holiday breaking out was going to Drexel,” Caroline says. “Until then, I lived this life working in food, beverage and retail. I’d work all day running the store, and then at night selling drinks on the floor. I had to break out. Moving to Philly and enrolling at Drexel all on my own made me a better, stronger person.”

She majored in corporate communications, but it was business that eventually won her heart. She took on two co-ops at Bristol-Myers Squibb. She didn’t live in the dorms, but rather at the haute corner of 17th and Walnut, less than two blocks from Tiffany’s. “This was important because I love Audrey so much,” she remembers. “It was my therapy.”

Her best friend at Drexel was Chimamanda Ngozi Adichie — a Nigerian-born aspiring writer who has since become an internationally renowned poet, novelist, MacArthur Foundation Fellow and Ted-talker. To this day, they remain close.

“Caroline was more experienced than the average student. She was better dressed and very pretty, too” Adichie remembers. “She was warm, intuitive, and she didn’t have the slightest bit of the kind of arrogant ignorance that I had encountered in some American classmates. She asked questions if she didn’t understand something, but always in an open and honest way, with no baggage. I loved her sense of humor. She had what I like to call a good B.S. detector.”

It was while on co-op at Bristol-Myers Squibb (Caroline was hired after graduation) working as an “intrapreneur” — responsible for inward-facing projects and internal fundraising — that Caroline encountered her first mentor: Susan O’Day, then-CIO for the company’s IT department. Caroline made an unsolicited call to ask Susan O’Day out for coffee. She never expected her to pick up the phone.

“I had no idea I was looking for a mentor,” Caroline says. “I thought I was looking for an advocate. However, it was strategic. I was calling for a reason. I knew I wanted help from a woman in the top tech position in the company. And she became an excellent mentor who helped me navigate the hierarchy and get hired after graduation.”

Cut to Caroline at a desk, or at her kitchen table — sitting across from a young girl, or even a teenager. Maybe they have their laptops out. Maybe Caroline is brushing the girl’s hair.

They’re talking about life: dreams, passions, failures, triumphs. They’re laughing. Trading funny stories. Caroline isn’t wagging her finger and dispensing wisdom. It’s just a conversation. If an opportunity arises for Caroline to offer advice, she takes that leap. This is what mentorship looks like. Spend an hour with Caroline, and she’ll try to mentor you. You won’t even know it’s happening until it’s too late.

“Where do you want to be in five years?” she’ll ask. And before you can answer she says: “Do you have a plan? You have to have a map!”

Since attending Drexel, Caroline has been a passionate mentor to more young women than she can count. First she offered after-school homework assistance through a nonprofit started by Philadelphia Phillies legend Garry Maddox that supports education for urban youth. She hasn’t been able to stop since.

Today, she is mentoring an 8-year-old girl through a program called A Family For Every Child that is devoted to foster children awaiting their forever homes. She has also been mentoring a 23-year-old named Whitney for the past five years through Big Brother Big Sisters, as well as several other young women she met while guest lecturing at the University of Oregon.

During the spring of 2012, she traveled with Mercy Corp, a Portland-based top-100 nongovernmental organization, to post-revolution Cairo, Egypt, where she delivered a series of workshops on raising capital, angel investing, and due diligence to a group of Egyptian entrepreneurs — many of them women.

“They’re not weaving baskets,” she says. “They’re creating iPhone apps and really cool stuff. But because of the culture, once their businesses become successful, some of their husbands want them to close down. So, I went over to do some mentoring.”

Among the long list of her own mentors is Mike Edwards ’83, executive vice president of global merchandising for Staples. Edwards was present when Caroline won Angel Oregon, and he was there when OsoEco failed.

“It never crossed my mind that Caroline wouldn’t get right back up,” Mike says. “Great entrepreneurs know how to fail fast and succeed fast. I found it personally motivating to be around someone who was that passionate about creating a company and creating opportunities. So, she inspires me. Today, our relationship is still strong as it ever was. We have great conversations.”

Says Caroline: “He stuck with me through all the failure and success. He has mentored me all along. And now we mentor each other.”

Today, Caroline is vice president of business development for Palo Alto Software, the developer of LivePlan, an online tool that helps entrepreneurs create pitches and investor-ready business plans. LivePlan integrates with accounting systems like QuickBooks and Xero, and displays management metrics. It provides for small businesses what does for personal finance.

Caroline was already familiar with the product when she came on board just weeks after the RealLead acquisition. In fact, she used LivePlan to write RealLead’s business plan. She’s got a beautiful office in a prototypical startup headquarters full of exposed brick and steel beams in the heart of downtown Eugene. She makes a point to always keep her door open.

So, back to Audrey and that Vespa scene from Roman Holiday. As Princess Anne navigates through those crowded Roman streets, her welps turn to joyous screams. She takes a couple of wide turns. She starts and stops. But just as she whips through the Piazza di Spagna by the magnificent Spanish Steps, she finally … safely … and most certainly … hits her stride.

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