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Gillian Muessig, longtime tech entrepreneur and investor and founder of the Sybilla Masters Fund. (Brettapproved Photo)

Gillian Muessig seems to have acquired more than one life-time’s worth of connections, venture capital experience and insights into how to help women — and really anyone else — succeed in business, juggling family obligations and entrepreneurial endeavors. Her resume includes such skills as “startup whisperer” and “product visionary.”

And the best part is, she’s willing to share her thoughts and advice with others.

Along with her eldest son, Rand Fishkin, Muessig co-founded Seattle-based Moz 17 years ago. She left the search marketing software company in 2012. Since then, she has served as an advisor to various organizations and sits on multiple boards, including the board for the cannabis company Soro. She is board chair and interim chief operating officer for Brettapproved, a company focused on accessibility for people with impaired mobility.

Muessig is also CEO of the VC company Outlines Venture Group, and earlier this year she launched the Sybilla Masters Fund with Microsoft veteran Alka Badshah and Outlines Venture President Anne Kennedy. The fund, which is named for a woman who went to England seeking the first patent for a person residing in America, provides dollars only to companies with at least one woman in a leadership position. (For the record, King George I in 1715 gave the patent to Masters’ husband and not Sybilla, noting that the invention was “found out” by his wife.)

“The power comes with capital. In the first world, in the third world, it makes no difference,” Muessig said. “When you put capital in women’s hands, things move forward.”

For eight years, Muessig and her business partner, Kennedy, have also produced a weekly radio podcast called CEO Coach.

“I generally describe it as containing all of the mistakes that I’ve made so you don’t have to make them. In truth, it is much more than that,” Muessig said. “The show is an advanced course in startup management, scalability and operations. We cover a great deal of information about funding and finance, since that it is top of mind for almost all entrepreneurs.”

Gillian Muessig, CEO of Outlines Venture Group.

We caught up with Muessig for this edition of Working Geek, a regular GeekWire feature. Continue reading for her answers to our questionnaire.

Current location: “Home base is Seattle. Currently on the road, working with startup companies in my portfolio and raising capital for the Sybilla Masters Fund. Ports of call include: Redding, San Francisco, Silicon Valley and San Diego/La Jolla in California as well as Scottsdale, Arizona. Followed by: Germany, Macedonia, Albania, Croatia and the UK. Total length of this trip: 59 days, 8 days in Seattle and 23 days in Europe. Then I’ll be in Seattle through the spring.”

Computer & Mobile types: “MacBook Pro, iPad 2, Pixel 6 by Samsung, accompanied by a portable scanner and solar power brick.”

Favorite apps, cloud services and software tools: “Google owns my life and they are welcome to it. The promise of the web is personalization and Google gets it right. Privacy concerns? Consider that until very recently in human history, there was very little concept of privacy. Humans lived in groups and even by the Middle Ages they were still in clusters in towns. Only a few left a town or traveled to a new town; it was a big deal. Almost everyone lived their lives among their ‘pod’ and everyone knew them and their business. It was only when cities became large enough to afford the possibility of anonymity that the masses became aware of the phenomenon. Perhaps it’s just a temporary phenomenon in human history.

Seriously, I live and breathe by Gmail, Gchat, Google Calendar, Google Docs in-the-moment collaboration abilities, and the synchronization of all my apps, docs, emails, messages and texts across all of my hardware, anywhere in the world. If my phone, laptop or tablet is lost, I can open everything I own on a new machine in moments.

That said, I use DropBox for document storage. Google Docs and sheets are great for instant collaboration, but nothing beats Microsoft Office. So don’t count out good old Microsoft just yet. I am still frequently in places without strong internet access, so I use the downloadable version.”

Smith Tower
The towering black Columbia Center is visible in the Seattle skyline from the observation deck of Smith Tower. (GeekWire Photo / Kurt Schlosser)

Describe your workspace. Why does it work for you? “My office is in my laptop bag. All the items listed above fit into one slim bag that I picked up in Stockholm’s Arlanda Airport. Sadly, it’s beginning to give out; I’ve been looking for a replacement for months. Even when in Seattle, I work either in a coffee shop or my living room out of that bag.

When in Seattle, I hold meetings at the Columbia Tower Club. Located on the 75th floor of the Columbia Center, the kitchen is decent and the views are stunning — even when the building is socked in by fog. If you wait a bit, the fog will move or lift, revealing an awe-inspiring view on all sides. As my business partner, Anne Kennedy, says, ‘No one denies you a meeting at the top of the Columbia Tower.’

The Columbia Tower Club has work pods and a restaurant, as well as a general space for relaxing at tables or in comfortable chairs. Between meetings, I work at the tables or lounging in the chairs.”

Your best advice for managing everyday work and life? “It doesn’t work for everyone, but I meld the two deeply. Since I had a ‘happy exit’ from Moz, I have the leisure to work on the projects that are dear to my heart. I love to travel. I love to help companies build better ways to live and work together. I am passionate about improving the gender, ethnicity, racial and physical ability equity in venture capital funding. I am fortunate to travel the world, collaborating with others working on these and similar issues.

For advice, I’d dig back into the early days of Moz. I melded family and work then, as well. I co-founded Moz with my eldest son. My youngest son would come to the office after work and grew up ‘under the desk.’ He performed small duties early on and along the way became very good at SEO. My daughter worked after school in those days and spent less time at the Moz office. But she was an extraordinary comfort and my personal cheerleader, always assuring me that I’d come out victorious.

I did not do a good job of separating family from the business. But I think the experience informed their views on the realities of the entrepreneurial journey and the enduring value of loving support during tough times.”

Your preferred social network? How do you use it for business/work? “Twitter and LinkedIn. I use social media exclusively for business. You will rarely find personal or family photos on any of my social profiles. I use Twitter daily to keep up with dear colleagues in my previous world of search marketing and to learn more about my current field of venture capital and gender-lens investing.

I use LinkedIn to make first contact with investors, advisors, founders and colleagues. I move the conversation to email if there’s a mutual interest.”

Current number of unanswered emails in your inbox? “I use three distinct emails daily and the windows remain open all day, every day: my personal account, Outlines Venture Group and Brettapproved, where I serve as interim chief operating officer and board chair. As I write this at close to midnight on a Friday evening, I have 16 emails (mostly nonsense) in my personal email, 41 that really require answers in Outlines Venture — although I confess that I cleared out about 30 when I got to this question — and 25 require answers at

So I guess the short answer is 96.”

Number of appointments/meetings on your calendar this week? “It’s been a very quiet week. Only 16 appointments. The first week of May, when I return to Seattle, I’ll have 21 in-person meetings and will likely add about 15 phone calls to that schedule.”

How do you run meetings? “In the summer, I stack up meetings one day a week, generally Wednesdays, and two days a week during the other seasons. In-person meetings are set for 50 minutes, giving me enough time for pleasantries, a bio-break or just a few minutes to walk and prepare for the next meeting. Phone meetings are set for 20 minutes, with 10 minute breaks between.

I meet thousands of entrepreneurs, investors, advisors, directors of incubators, accelerators and more. I give any entrepreneur who is building a scalable company one meeting. I ask them to email me an executive summary and a pitch deck before we meet. If they haven’t developed one, I expect a synopsis of what they are building and what they want me to provide during the meeting, their ‘burning question,’ as it were.

If I don’t get the documents before the meeting, I generally shorten the meeting, wish them well, and close the relationship. What cuts the wheat from the chaff is the ability to deliver. Ideas are a dime a dozen. Execution is required for a company to survive. Thriving is an advanced business discussion. If the entrepreneur can’t perform sufficiently to meet my ‘survival’ requirements, we don’t move on.

For those who make the mark, I offer one more meeting and make connections if the next meeting proves to me that there is some serious value in the company and its founding team.

Across the board, before any meeting, I include an agenda and how to contact me in various ways in the Gmail Calendar invite. If the other party doesn’t accept the meeting, I reach out to ask them to confirm and to provide me with contact info. Preparing well for meetings makes them more productive and including mutual contact info such as cell numbers has saved me a month’s worth of time or more in missed queues over the years.”

Everyday work uniform? “Black slacks, black or white tee, and a sport coat or over-shirt if it’s an informal day. Color comes from scarves, which I wear year-round. Friends call my scarves my ‘prayer shawls.’ The monochrome wardrobe helps me pack light and the scarves and jewelry help me feel put together. I am something of a minimalist and own very few clothes or shoes. (Hence, my ‘office in a briefcase.’) But I own dozens of scarves that I’ve collected on my adventures around the world.

My most-used scarf is made of undyed cashmere in a fawn color. It was a gift from a colleague in Afghanistan. I wear it on airplanes or other long trips. It is very large and can wrap it around me like a thin, but surprisingly warm blanket. You can pass the entire massive scarf through a simple finger ring because of the nature of cashmere. I can wear it as a western scarf around my neck and I can throw it over my shoulder and wear it over a shirt or even a sport coat. It is always elegant and striking.”

How do you make time for family? “I take them with me! I travel often with my husband, who is now retired. I’ve traveled with my children to Europe or conferences or other events in the U.S. and abroad. And regardless of where I am, I stick to the same rule of business and family regarding phone calls. That rule is: children get through, grownups can take care of themselves. I’ve had the same cell number since the early 1990s. Whatever I am doing, wherever I am in the world, and whoever I may be meeting with at the moment, if one of my children calls, I answer the phone. I’ve made it plain to clients, colleagues, employees and everyone else that these are my rules and I encourage others to follow suit.

My children know that they come first, without exception. They do not abuse the process. If I am in a meeting, I say so and they are always gracious. We chat when the meeting is over. But in the event that something needs tending immediately in their minds (something that occurred more frequently when they were little and became very rare as they became highly capable adults) I am there for them. Everything else stops and waits.

In her last year, my mother made the ‘kid list’ and I would pick up the phone immediately whenever she called. These days, my parents-in-law, who are 90 and 91 years old, are on my ‘kid list’ and I am sure to answer in case they have a pressing need.

My husband and I have had a long-standing process: If we call once and there is no answer, we can leave a message or wait until we see each other later. If we call twice, it means something is pressing and the other calls back as quickly as possible.

We are not sticklers for holidays and birthdays. Since the children were little, we’ve said, ‘Holidays and birthdays are celebrated when family gets together.’ Our family members are often on the road. We wait for each other and celebrate when we are together.”

Muessig cycling in India with a friend in January 2014. (Muessig Family Photo)

Best stress reliever? How do you unplug? “I cycle. I bicycled in Uttar Pradesh India with my brother for a month in 2013 and we were seriously unplugged. We reprised the event with a cycling journey from Delhi to Agra a year later and took colleagues along with us. I generally cycle to and from my residence to meetings. Now that ride-sharing has come to cycles in Seattle and many other cities, I often grab one even if I don’t have my own cycle with me that day.

There’s nothing like a long ride to put one’s thoughts in order. You move at just the right speed. Not to fast so you miss the space; not too slow that you become impatient with slow progress toward a destination.”

What are you listening to? “Silence. Even if I’m driving, I love the silence. It’s so rare and I find I crave it more and more.

When I’m listening to music, it’s likely to be ‘long hair’ or music from the classical composers. From Gregorian chants to classical, baroque and right through to jazz, I love it all. Opera takes concentration, so I can’t work at the same time. I learned to read music before I could read words and I play the piano to relax when the weather is not suitable for cycling.”

Daily reads? Favorite sites and newsletters? “I have a lot of daily feeds related to global trends, general, technical, search marketing and startup investment news. I particularly look forward to the venture capital database CB Insights. The research and presentation of information is brilliant.”

Book on your nightstand (or e-reader)? “‘I’m a Failure’ by Akhil Sharma. Surprising wisdom and insights into the Indian startup phenomenon, woven into personal stories and experience.”

Night owl or early riser? “Both. Tonight, I am working late. When I am Seattle, my days start at the gym at 6 a.m. with a trainer. That keeps me honest. I have to go because someone else got up early and expects me to show.”

Where do you get your best ideas? “My business partner says: ‘Opportunity comes from loose connections.’ I certainly get a lot of great ideas from meeting new people or being among colleagues with whom I have ‘loose connections.’ But I also maintain a group of powerful movers and shakers around the world with whom I meet once or twice a year, either in person or via a meeting platform. From Hong Kong to Copenhagen, the Congo to San Paolo, I get a sense of the global trends across a broad variety of industries and interests. The longer I know these colleague-friends, the more valuable these exchanges become. We keep each other informed ad hoc as well. Getting input from all the corners of the globe helps develop ideas that have legs to run the distance.”

Whose work style would you want to learn more about or emulate? “Winston Churchill. The man could run free Europe during a global meltdown from his bed in the morning, drink like a fish and eat like a seasoned gourmand all day and night, all while wearing a top hat and formal suit. And he still wrote all of his own material!

I’m quite sure I’d be dead in less than a year if I tried that. But I love to learn ever more details about how he worked, because he was so extraordinarily effective in his endeavors.”

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