Co-Founder of Outlines Venture Group and General Partner for the Sybilla Masters Fund, Anne founded the world’s largest digital marketing consortium. She is also the author of the seminal book on international search marketing, Global Search Engine Marketing, a speaker and advisor to multi-national internet brands.

Anne Kennedy is a serial entrepreneur with decades of experience in online branding and PR. She improved Hearst Newspapers, Philips Lifeline, Dunkin Donuts and other household-name brands online and directed the stunning online launches of dot-coms Zillow, Jib-Jab and Avvo. Also, she serves as a co-host of CEOcoach podcast and a mentor at Ben Franklin Tech Partners in Philadelphia.

Q: Could you share your story with us? What have been the best moments of your career?

In a career of nearly 50 years, there are so many, but I would have to say being part of launching new industry in digital marketing and making many friends around the world while we invented SEO were memorable. We have always been the first.

Publishing my first book “Global Search Engine Marketing: Fine Tuning Your Search Engine Results” (Que Publishing: 2012) was certainly a high point, as was launching Zillow and watching it race to #4 in six weeks for the search term “real estate”.

Producing CEO Coach has been a special joy, where Gillian and I can explore hot topics and voice our observations and opinions. I am thrilled when I hear from listeners or when one says “I know your voice”, when I meet them.

Most recently, mentoring entrepreneurs from Central Europe for the U.S. Department of State (Young Transatlantic Innovation Leaders Initiative) has been extremely rewarding. At one time, it pleased me to launch my own businesses; now, I am happy to advise founders, sharing what I know, largely from my own missteps — of which there were many! I am happiest when I travel far and wide, meeting entrepreneurs, hearing their stories and supporting their work. When Gillian Muessig and I formed Outlines Venture Group to do just that, I knew I had arrived at the right place at the right time.


Q: What motivated you to build your company and what made you decide to become involved in venture capital?

With my expertise in search engines, I earned a seat on the board of directors of a content start-up platform called Helium which had a successful exit (25x revenues) after only five years. Though a white male founded company with white male PE funding, I learned a lot sitting on that board, the only woman at the table for the first three years. The lead investor was a very good teacher. I saw what was possible.

The sale of Helium to RR Donnelley provided enough cash to allow me to do as I pleased. Anyone would call that a happy moment. Most important, this was my opportunity to support my life-long belief in diversity: multiple points of view and experiences lead to richer life and to more successful outcomes.

At the same time, my business partner Gillian Muessig had a successful exit herself from Moz. We admired each other’s work and we had become good friends traveling around the world for SEO conferences. We knew we wanted to work together, we were excited by entrepreneurs and we wanted to give a helping hand to start-ups. We began with a small portfolio of investments, in both cash and mentor capital. When one start-up, for which I was an advisor, thanked me for meeting with them, I said “No, you have it backwards. I own shares in this company, so your success is my success. Now go make me some money!” As I left that visit, I texted Gillian “we’ve found a business model.”

After several years as angel investors, we realized our sister founders are receiving a pitifully small access to venture capital, crippling their ability to scale. We decided to change that and bring gender parity to venture funding. Further, as angel investors, we observed faults in the current system that needed tweaking, most notable a large gap in post-seed funding that needed filling.

Q: You are a very inspiring woman with an impressive track record. What motivates you to keep going? Do you have a formula for becoming a successful entrepreneur?

My career started in 1970, now nearly half a century ago. I am keenly aware that time is now limited and I firmly believe in leaving the world a better place — at least my small part of it. Economic prosperity is the key to peace and security — doing well by doing good and doing good by doing well.

Plus, entrepreneurs have a zest for adventure and risk and are fun to be around. Most of the ones I know are decades younger than I, and that keeps me from feeling my age.

Q: VC funding is a heavily male-dominated area. Have you ever felt discouraged working in this field and what advice would you provide to women who want to follow this path?

Ah, the Old Boys Club, the Bros, most of them are white. Where to begin? A few weeks ago I reviewed a response from an investor to a woman founder and itCo-Founder of Outlines Venture Group and General Partner fo was filled with multiple reasons why he would not be investing, all in an effort to cover up that he would not invest because he believed a woman was not capable of success. Sometimes I hear questions a man would never get, such as how are you going to raise $100 million? Disappointingly, some of these questions come from women who work in male-led VC firms.

I have no time to be discouraged, so I push it away and reframe such comments into action steps. The boys’ rules are tired, producing inflated, over-subscribed investments, as well as billions of dollars in capital that sit on the shelf, contributing nothing to progress. How many products and services that would clean up the world’s water supply provide more effective cancer cures, and help raise healthier babies are going unfunded because their founders proposing such advances are women?

On the bright side, I observe a growing core of women innovators stepping into the venture capital arena, many with fresh approaches unencumbered by old rules. The Women’s Venture Capital Fund has been active for ten years. Backstage Capital, Chloe Capital and BRAVA Investments are newer. My advice to women who want to become VCs is to seek out the groups of women VCs who are running their own shows, join with them and make your efforts stronger together.

Q: How will the world of venture capital change in the next 5 years and what role will women play in this industry?

If I have anything to do with it, there will be gender parity in funding. It has been said that at the rate we are going today it will take 170 years. I am not waiting that long!

Q: What are the 5 most important skills an entrepreneur needs to master to be successful?

The 5 most essential skills are:

Time management, Communication, Planning, Financial modelling, Product development

As a bonus, these 4 necessary key attributes:

Persistence, Patience, Optimism, Vision

Q: What advice would you give to your 20-year-old self?

First, delay marriage till you are 30 — this is what I told my sons since I was married at 20 and divorced at 35. All that took a lot of mindshare, but my sons are extraordinary grown men, so I am glad I went through that.

Second, believe in yourself, even as the world tells you you are not worthy, for so many reasons, not least, because you are a woman.

Q: Looking back at your career — if you were to do it all again, would you do anything differently? If yes, what?

Not much. Each step has been on my journey to where I am today. I evaluated each opportunity and decided whether to take the leap. And then leapt.

Q: What is next for Anne Kennedy?

A legacy: gender parity in VC funding, which will lead to more women entrepreneurs funded to successful exits! And a world commitment to diversity in all its forms. Only then, I will “retire” to a beach somewhere to write trashy novels under a palm tree.


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