I had the pleasure of talking with Douglas Crets of the Microsoft BizSpark program about our work on mobile health for moms and OBGYN doctors at Pregnancy Companion, check out the livestream video interview.
Before I had kids, after taking a brief three-year hiatus from tech startups, I learned how to meditate. Every Monday night I drove over the Golden Gate Bridge from San Francisco to Spirit Rock, a meditation center in Marin where Jack Kornfield has held group meditation teachings (known as ‘Monday Night Sitting‘) every week for over twenty-seven years. I’d sit in a roomful of strangers as Jack would guide the group through vipassana meditation, or mindful awareness of breath, body, and whatever is arising in the moment. Cultivating awareness and quieting the chatter of the mind is (still) one of the most challenging internal battles one can take on. Try to quiet your mind for even five minutes, and you’ll hear what I mean.
Now that I’m back in the world of startups and immersed in an industry full of 24×7 social media and mobile chatter, the challenge of quieting the mind and the external noise is even greater. While I meditate for a few minutes every day, there is nothing quite as gratifying or soul-soothing as a forty-eight hour vacation from all external inputs. That includes a full-fledged media fast: no cellphone, email, Internet, Twitter or Facebook (gasp!). The one luxury I allow myself is a phone call goodnight to my husband and kids, my lifeline to human connection while I disconnect from the rest of the world.
My system has been on overdrive lately, and I can feel it in every cell of my body – a result of too many months of too much caffeine, working late nights, sleep deprivation, one too many work conferences and not enough moments of ‘just saying no’. Juggling startup life, two young kids, and a full social and family life can feel like a double full-time job. And as my dear friend likes to say, “when mom is not taking good care of herself, no one else gets taken care of well.” True!
I’m signing off for a few days to unplug, unwind and turn down the noise to take off on my annual ‘Me Retreat’. I’ll indulge in a good book, eat decadent lunches and dinners by myself, maybe get a massage or two. Perhaps I’ll get to sleep in one morning and work away at that sleep deficit I’ve built up. I know the world will go on without me, and that I’ll be just fine without needing to constantly ‘check in’ to the non-stop feed and frenzy. I know my husband will hold down the fort and appreciate my presence in my absence. I know my kids will miss me but be in good hands, since I’ve scaled myself well (hiring and training competent childcare). And I will be at peace. Even for just a short while.
It was the summer of 1999 and the last product I launched was the LinkExchange Store, the e-commerce site that enabled web site owners to buy ads on Yahoo!, Excite and LinkExchange with as little as $25 and a credit card. Since I loved throwing myself into the most pressing startup problems, I switched roles from product manager to ad sales lead to help monetize our ad network to agencies and branded advertisers. I closed one of our largest ad deals with Microsoft, who became my top advertising client and later acquired LinkExchange for $180M at the height of the Internet bubble. Predictably, the startup culture post-acquisition quickly disappeared with most of the early team members moving on to their next startup. Tony Hsieh, who recruited me to leave my job in Seattle and join LinkExchange as a lead product manager had quickly moved on to start Venture Frogs with Alfred Lin. All my favorite people were leaving en masse to their next startup, and there I was selling display ads and brokering partnership deals for Microsoft. I was itching to get back into a product-focused role and actually build something, so I started searching for the next great startup idea and team.
It was at this time that my brother, an undergrad at UVA, introduced me to Napster, the peer-to-peer music sharing service going viral at college campuses across the world. Although we were worlds and miles apart (me doing startups in San Francisco, he living in Charlottesville having a college experience), we quickly bonded over our music collections, which included a lot of Dave Matthews Band, U2, Coldplay, and Sarah McLachlan. I fell in love with the Napster product and found myself connecting with music fans all over the world and trading tips with my bro on what music to discover.
Sean Parker and Shawn Fanning had just moved to Silicon Valley and were working out of Napster’s office in downtown San Mateo. Shawn’s uncle, John was closely involved with the company and had recently brought on CEO Ilene Richardson to help the company scale. After a lucky run-in with my entrepreneur friend Bill Bales who was an early angel investor in Napster, I got connected to Ilene, John, Sean and Shawn to interview for the first product manager position and help them scale through the next phase of viral growth. I remember thinking just how young Sean and Shawn seemed to me, and while they asked intelligent questions during the interview, it was mostly Ilene and John who talked.
Napster seemed like the ideal startup to work for, as Sean and Shawn were young, smart hackers and co-founders (just like Tony and Sanjay from LinkExchange) and the company clearly had a viral loop and a product that could (hopefully) scale to millions of users. Millions of users meant millions in potential revenues, if only the legality of the software and music rights did not pose such a huge liability. I had a good feeling that I had nailed the interview and felt a strong rapport with the young co-founders, but I also had nagging doubts about the ‘grown up supervision’ to whom I would ultimately report, and whether the team could find a path to success from user growth alone, and despite the legal landmines and the lack of revenue stream.
I got the call from the CEO the next day who seemed thrilled to offer me the position of product manager at Napster. I think she was truly perplexed when I turned down the offer, almost immediately. Although a huge part of me wanted to join ‘the next big thing’ in music technology, I couldn’t silence the voice in my head and the magnetic pull in my gut that said the Napster path would be full of heartache and headache as a product manager and early employee. That was the day I turned down Napster, and surely an exhilarating and wild close-up ride on the roller coaster story that we know now.
At SXSW last week, Shawn Fanning and Sean Parker appeared on a panel with director Alex Winter to discuss the documentary created by Winter called ‘Downloaded’ on the story of Napster. I caught up with Shawn after the talk who asked me how I felt about not joining Napster back in 1999, “it looks as though everything turned out okay,” he said jokingly. It would have been an amazing experience to work with Sean and Shawn, even with Napster failing who knows what startups could have materialized after that experience. I told him my reasons for not joining, the legal mess being one of them. “It was probably the right choice from a product management perspective,” he said, “we did not innovate on the product AT ALL, you would have been very frustrated and not gotten anything accomplished.” That sounds like the ultimate hell as a product manager, watching a product you love not progress one single line of code beyond where you started – not because users didn’t LOVE it, or that there weren’t so many areas to innovate on, but because your hands were tied up in a titanic legal mess of David vs. Goliath proportions.
Either way, it’s an amazing story of what shall remain for the history books as one of the most disruptive forces in the music industry ever. Napster paved the way for products like iTunes and Spotify, and respect goes to the original creators of the first music sharing service for our generation. Can’t wait to see Downloaded on the big screen! If you want to join me for the San Francisco release, ping me on Twitter or below. It’s nice to reminisce sometimes.
I had never planned to attend a women’s college. Far from it. I wanted to join the big boys at Georgetown and pursue a diplomatic career getting my bass-ackwards country back into shape. I never realized that women’s colleges existed until I approached my AP English teacher Mrs. Timoney for recommendation letters. “I am extremely disappointed that you have not considered Smith College,” she said in her most dignified and disappointed voice. “Huh? Where is that?” I asked. [Look of utter shock from my most respected teacher!] Ooops. Wrong response. “Please, tell me more, I’m interested!” I said.
“It is a most impressive academic institution, and you would be doing yourself a disservice not to consider it,” she told me. She told me of her own daughter who had graduated Smith and more recently, Harvard Law School. She raved about the class size, the focus on academics and teaching over publishing, and the women who were “simply brilliant”. She talked about the amazing network of successful women who would act as lifelong mentors and advocates for my professional success. Who were these magical women and how could I be like them? It all sounded so amazing. I applied that same week and was accepted a few months later, in no small thanks to the glowing recommendation Mrs. Timoney wrote me (I saved it for sentimental reasons, and it still makes me tear up more than 20 years later).
After spending a weekend on campus during my round of college visits, I realized that I owed Mrs. Timoney a great deal of gratitude for pointing me down a path I never would have considered otherwise. For many reasons, Smith was the right choice for me. I probably wouldn’t have pursued economics or graduated early or entered the mostly male-dominated field of technology and startups, had it not been for my Smith education.
Today, on International Women’s Day, I thought I would take a moment to thank my first true mentor Mrs. Rosemary Timoney. She helped shape my life in the most meaningful way, she’s the reason I went to Smith College and why I’m so passionate about supporting women on their journey to success.
Startups aren’t for the faint-hearted, as anyone who has survived more than one will tell you. Startup life can be crazy, lonely, exhausting, and even heart-breaking at times — while also being exhilarating and fulfilling in the same day! Startup stress accumulated from long hours, all-nighters and ‘always on’ work pressures can challenge even the most solid relationships with family, friends and loved ones. Unless you’re actually in a relationship with your co-founder (like Eventbrite co-founders and husband/wife team Kevin and Julia Hartz) or with someone who is also in a startup or has been before, you may feel like your boyfriend/girlfriend/partner/lover/spouse just doesn’t understand you. If you’re lucky enough to be with someone who ‘gets’ you and your startup life, be thankful and be sure to let them know how much you appreciate them.
Before I met my husband (thank you founders of Match.com), i had already been through the ups and downs of five startups. Some successful, several failures. He was a serial entrepreneur who had also founded several startups, had succeeded and failed, and understood my passion for launching ideas that could disrupt the world. We found a kindred spirit in each other, someone who could empathize with the other’s passion while also providing emotional camaraderie after a hard week’s work in the startup grind. Neither of us ever felt neglected when we pulled an all-nighter or jumped out of bed at 2 in the morning to put out a work fire. That’s just what you do when you’re committed to making your startup successful.
Perhaps the craziest test of our relationship came when we decided to launch our family (and give birth to twins!) in the same year my husband became a startup CEO. We are lucky that we can both function on very little sleep, as we barely got any for two years. Our motto back then?: “Sleep is for the weak”. We survived that rough stretch with a lot of help from grandparents, hired helpers and our own resolve to keep our marriage together, no matter what work or babies threw (up) our way.
Our weekly date nights saved us from being too baby- or startup-focused and gave us at least a couple of hours each week to reconnect. If there’s one non-negotiable to keep your romantic relationship from flaming out while you’re in startup mode — keep your date nights sacred and make time for connecting one-on-one, just like you would with your co-founder, investors or team mates. After all, your team mate on your life journey is probably (and hopefully) more important than any of the people you’re working with, with greater impact on your lifelong happiness than whether your startup is successful – read Clayton Christensen’s How to Measure Your Life for more insights.
Our twins are now five years old and my husband and I have both been through three startups each since they were born. We couldn’t have tackled the challenge without a whole lot of empathy for each other’s passion, plus collaborative team work to manage our household, childcare and taking care of ourselves as well as our kids as true partners.
On this Valentine’s Day, I’m feeling most grateful that my life partner is also my greatest startup partner and supporter of my professional dreams.
Silicon Valley VC Vinod Khosla wrote an insightful post on TechCrunch asking the question ‘Do You Need to Be a Jerk to Be a Successful Entrepreneur?“. He contrasts Steve Jobs’ ‘jerk-like’ behavior with his phenomenal success, while explaining that being successful and treating people fairly are not mutually exclusive. While entrepreneurs are not always the easiest people to love, there are thousands of successful entrepreneurs who are not jerks. Take Richard Branson, Marc Benioff, Mark Zuckerberg, Aaron Levie, Sarah Blakely and Oprah Winfrey to name a few.
You don’t have to choose between success and being nice, good, fair or treating people well. “It’s a false choice,”says Khosla.
How much do you love your Monday mornings? If you are fortunate enough to be doing the work you love, you might approach Monday mornings full of excitement for what the week holds. Perhaps you’re the founder of your own company, or running your own small business.
If you don’t love your job, Monday mornings can be tough. How psyched you feel about going to work on Mondays is an important barometer for job satisfaction. If you’ve had years of unhappy Mondays, it might be time to consider a shift in your work or your chosen employer.
Imagine what it would take to love your Mondays again. Do you want to do your same job but work with different people? What if you had more job autonomy and the freedom to work from anywhere? What if you spent less time sitting at your desk, and more time connecting with people? What if you could hand-pick the team you want to work with every day? What if your compensation was based on your performance instead of based on office politics? What if you could be your own boss? What if you had full control of how you spend your time and who you spend it with?
If you’re exploring new opportunities and wish you could find a way to work for yourself but don’t know where to start — whether you’re in a job where you love your Mondays, or in a job where you don’t. Connect with me and let’s talk! I’m passionate about helping people grow to their full potential, and am recruiting a team of people to work with me as cloud consultants. Find out more.
Don’t let this be you for much longer:
I’ve been involved in over a dozen startups since moving to Silicon Valley in 1996. When I moved here in my early twenties, I had seemingly endless stamina to pull all-nighters. I was pretty much immune to both sleep deprivation and caffeine overload. This made it very easy to throw myself into startup life, which looking back — I think I was addicted to: the thrill of building products that could disrupt then-giants like Microsoft and Yahoo! (ha!) fueled many of us to burn the midnight oil for years.
After LinkExchange was acquired by Microsoft in 1998, I stayed on for a short while to see if the ‘Microsoft Way’ would suit me, and I soon realized the answer was ‘no way’. I longed for the fun and fast-paced startup culture that surrounded me in San Francisco, so I joined one early stage startup after another. One in the mobile space (when WAP handsets were the thing), and another in the e-commerce space (a predecessor to Wag.com – which is cool now that Amazon’s doing it!). Both ran out of money and steam so I moved on to an enterprise-focused mobile startup called SEVEN.
The company seemed full of promise, it’s founder Bill Nguyen had recently sold Onebox to Phone.com for $850 million. They were going to redefine how enterprises accessed their corporate email on wireless handsets — this was before the iPhone or Android existed, and the only way to get your email was through a Blackberry. As the company’s first program manager, I was sent to London to build out a custom product for a wireless carrier partner. My first job as an international wireless project manager made me ideally suited to working with operators and managing large-scale projects. This one required mobilizing dozens of people who didn’t report to me to collaborate across several timezones and deliver a product under insane deadlines. I liked a good challenge! I had also grown accustomed to falling asleep on long-haul flights while being able to wake up completely refreshed, so the travel didn’t daunt me. My secret? Melatonin and a good glass of port.
While I initially loved spending time in London, the cross-Atlantic trips and constant jetlag started to wear me out. It also became ridiculously expensive for the company to put us up in hotels for weeks at a time, so I volunteered to move my life to London, lease a flat, and stay until the project’s completion. What started out as ‘several months’ turned out to be more than a year.
As anyone from the West Coast who’s worked in Europe knows, the time difference is just convenient enough between London and San Francisco that you can practically work an entire two business day’s worth back to back! Just as my London day came to a close, the Silicon Valley office would open up and I’d spend hours on the phone or over email late into the night, collaborating with colleagues. It made for a gruelingly long work week, and ultimately my immunity to sleep deprivation wore out. So did my passion for startup life. There I was, in one of the most amazing metropolitan cities in the world, and all I wanted to do on the weekend was catch up on my sleep!
To console myself that I did actually have a life and this was all somehow worth it, I managed to take the train to Paris on the occasional weekend. When I had a particularly good week at work and was feeling upbeat about living so far from my family and friends, I took several spontaneous trips on LastMinute.com. My criteria for a getaway was If I could get to a destination in under 3 hours for less than a $300 ticket and spend less than $300 all weekend, I’d book it. I saw Reykjavik, Seville, Santorini, Istanbul and Rome. They were great adventures, but ultimately I missed having friends to share them with.
Then on September 11, 2001 while en route to a work meeting in a London cab, the first breaking news report that the World Trade Center had been hit by an airplane came over the radio. I remember the moments after that vividly. Instead of having our team meeting we gathered to watch the BBC News and agreed we would all go home and call it a day. It was from my hotel room that I watched in disbelief as the second tower was hit live on television. At that moment, none of the startup glory mattered. My international adventures didn’t matter. My bank account didn’t matter, nor did my glorified options. Even the feeling of being really kick-ass awesome at my job paled in comparison to the feeling of wanting to go home, be with family, and see my friends. Something big shifted inside me that day, and though I couldn’t quite place it in the moment, it felt like a layer of illusion had been torn from my whole perception and that somehow, my life would not remain the same. On some level, I was done playing the game that somehow work was all that mattered in order to define my self worth in the world.
Six months later, I packed up my London apartment to take what would be my last London – SFO trip for a long time. Having wrapped up the first launch of the company’s project, my heart, head and body were no longer able to give any more. I decided to take a sabbatical from startup life and give myself time to just be. I figured since I had graduated a full year early from college to save on tuition and to start making a dent in the Universe, I had ‘banked’ at least a year’s worth or more of time to figure out the next phase of life. I was barely thirty years old.
What advice would I give to my twenty-something self, knowing what I know now? While I wouldn’t advise her to change a thing about the journey she took, I would urge her to savor the moments more. To ‘pursue’ and ‘do’ less, and just “be” more. To pay closer attention to life outside of the working world. To breathe more and to be still. To be aware of her body and to take care of it — feed it well, exercise, and don’t be fooled into thinking it is invincible and can’t be damaged by lack of sleep. To be kind to herself, even when being tough seems expected by the men in the room. And to know that life is teaching her something even through the moments that don’t deliver happiness. Especially those ones.
In a future post, find out how I launched my own small business, became an expert in the wellness and maternity industry, then returned to startups on my own terms.