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9 Lessons From an Accidental Entrepreneur

Andrea Kihlstedt reveals what she learned launching her online business Asking Matters — and how to make money on the Internet

By Elizabeth Isele

Andrea Kihlstedt of New York City had a highly successful career as a fundraising consultant and trainer and also authored Capital Campaigns, Strategies That Work and How to Raise $1 Million (or More) in 10 Bite Size Steps. Then four years ago, she began thinking about how to expand her reach.

"As a consultant," she says, "I was only selling my time to clients; I never thought of myself as an entrepreneur. I wanted to create not just more work for myself, but an online business I could market to new customers.”

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So Kihlstedt linked up with a partner — professional fundraiser Brian Saber — and they plunged headlong into launching, a site designed to teach nonprofit staffers and board members to ask for donations by identifying their own “asking style.”

A 10,000-Person Following

Today, Asking Matters is an online community with an email audience of nearly 10,000, plus a membership of 350 and growing. The site offers free and fee-based fundraising tools and services, including workshops, individual coaching sessions and even $4 motivational pens sporting such slogans as "Ask for the World!" The site recently began selling Kihlstedt's latest book, Asking Styles: Harness Your Personal Fundraising Power.

In just three years, Asking Matters has achieved a positive cash flow. Kihlstedt anticipates that in its fourth year, the business will yield a decent income for Saber and her.

Here, Kihlstedt lays out the nine lessons she learned when she became an "accidental entrepreneur." They could help you avoid pitfalls if you choose to follow her path to launch an online business.

1. Just start. "I love the Internet because it’s so easy to make a change to a website if you make a mistake. You can put an idea out there immediately and then simply correct it, if necessary. This gives me the courage to move ahead without feeling like I have to be perfect. ‘Perfect’ blocks your ability to simply dive in.”

2. Learn as you go. "I had no experience in business startups, never mind an online business startup. So I had to learn about Web design, how to manage a website, online curriculum design, social media marketing and videography. I found online resources for many things, hired consultants for others and often relied on messy trial and error. I was learning so much every day, I felt like I had thrown myself into some kind of Harvard/MBA super-accelerated training program."

3.Understand that having a business partner is like being married. "Brian is almost 20 years younger than I am and we each have different skills and temperaments. Like a marriage, it's not always easy to accommodate our differences. Brian is more organized than I am and values consistency and strategic planning. I'm more of an innovator and a free spirit. We're a great team, but it's certainly not always easy."


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4. You can find plenty of free Internet applications for your business. "I knew that I wanted to develop and market an online fundraising course but didn't know how. I started asking young, tech-savvy people I knew for the best ways to present a course online and one of them told me about the free open-source platform, Moodle. It lets me create and present the course calendar and discussion forums. I also use Moodle to post course materials easily, with the ‘Asking Matters’ logo.”

5. A social media pro can help connect your business with its natural constituency. "My first thought was that all we had to do to be successful was post a wealth of information on the site and people would beat a path to our door. But we hadn’t figured out how to make money online. So we hired a social media consultant who taught us about the value of blogging, newsletters, Twitter, Facebook and LinkedIn. We started social networking aggressively and gradually built an email list of thousands of people who buy our products."

6. Don’t be afraid to make mistakes. "I’ve learned how to shoot and edit video interviews of experts and they’re now some of our most popular pages. I’ve actually gotten quite good at it, but along the way I've made some embarrassing mistakes. Fortunately, everyone's been good humored about them and we’ve been able to correct the footage. Today, anyone can make and share a great little video with an inexpensive camera or iPhone. All you have to do is be willing to make a fool of yourself for a while as you learn — and even that can be fun."

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7. Put specialists on your site and the page views will follow. "I have found that engaging other experts for videos, articles and commentary increases our Web traffic. People who follow them come to our site and our followers go to theirs."

8. It’s not your name that counts, it’s your brand. "Brian and I initially thought we wanted to brand the business with our own names since we each had a following in the fundraising arena. But we're very glad we chose to name it 'Asking Matters' instead, because that will make it easier — when we are ready — to sell the business to someone who’ll keep the brand going."

9. Your age doesn't matter when you're on the Internet. "Ageism falls away with this medium. It's your energy and intellectual capital that matter. You could be 85 years old and people wouldn’t care."
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Elizabeth Isele is a serial senior entrepreneur. She is co-founder of, co-founder of, founder of and co-creator with Participant Media of the 2015 global summit series on Senior and Multigenerational Entrepreneurship. Read More
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