Starting the next chapter...

When you leave a company after twenty-one years, the change is exciting and refreshing- but candidly, the ambiguity of what’s next is somewhat intimidating. It’s now been six months since I stepped out of my role at Microsoft, during which time I’ve received many questions about what I’ve been up to, and what I might do next. So I thought I’d share this post.

The gift of time

I spent the first month with colleagues to say thank you for so many great memories. One of the most impactful discussions was with a good partner from France, Yves Maitre. His core message was that I was now “time rich”. He advised me to spend my time very thoughtfully and not lose control of this asset. I feel like I’m still digesting this feedback and learning how to live up to this wonderful advice.

On that note, it’s been inspiring to spend more time with the Seattle Foundation. I love the Foundation’s long term, 360-degree perspective on my local community. Few regions of the world have the wealth creation, innovation, social responsibility and pioneering muscle that we have here – but at the same time, we have some critical negative trends to address in income inequality, education achievement, and the opportunity gap so many kids face. I want to do whatever I can to help the Foundation lead us through this.

Likewise, I joined the Board of Visitors at Duke University's Pratt School of Engineering. I feel lucky to have chosen Duke for college, and grateful for the doors the school opened for me. The school has a new Dean, Ravi Bellamkonda, who really impressed me with his respect for what the school does so well - and the challenges ahead. We discussed how Duke alumni lead Apple (Tim Cook, Eddy Cue, Jeff Williams) and Microsoft (Amy Hood, Scott Guthrie, formerly myself), but Duke has so much opportunity to improve and lead in the computing experience students receive. Hopefully, I can contribute to this experience and give something back to the school which gave so much to me.

To the amazement of many (especially myself), I signed-up for the Honu Half Ironman unsure if I was really up for it. The hours of training helped reset the impulses in my brain to a more relaxed cadence (probably akin to doing several hours of meditation per day). After having gotten so out of shape during the peak intensity of my Microsoft years, it felt amazing to complete this race in seven hours. I know, it’s hard to believe even for me – here’s a picture for proof. ??

I was originally debating guitar or piano, but then I discovered Simply Piano, an incredible app to learn how to play… Piano! I always loved Rock Band on Xbox. Seeing that concept adapted to teach real piano playing is so impressive. My kids still find my playing “annoying”, but I think I’ve gotten “ok”.

But most of all, looking back at my time off, it’s been great to strengthen my relationships with friends and family. I find it crazy to consider that I have a son leaving for college in less than 2 years. There really is no substitute for just spending time with the most important people in your life.

So… what’s next?

Sometime early summer, I started thinking “I should do something when the kids go back to school.” I missed the flow of a team and learning something new every day. My golf game had improved, but I needed to get back into the real game.

I was fortunate that some great opportunities reached my inbox, and I responded to a few to learn about them, and frankly, to learn more about myself. After being married to Microsoft for 21 years, it was very interesting to get out and meet people on the outside, and see the diversity of opportunities out there. I realized pretty quickly from my discussions that right now isn’t the time to get married again to another all-in role. But, I enjoyed meeting new people and talking with each of them about their work.

Around that time, I reflected on one of my favorite things to read every year– the Berkshire Hathaway Shareholder Letters. I recall reading these letters for the first time twenty years ago, and how they were eye-opening about how the stock market and business really worked. I wondered if there was a role I could play as part of an investment group. I really liked the idea of thinking deeply about many businesses vs. going deep with one. So I started having discussions with many of them.

And now today, here I am sharing that I have joined two great investment organizations, complementary to one another, where I think I can make a big impact. Both organizations were able to design part-time roles for me so that I can contribute to each, while also continuing to give back to the community and be present with my family.

Venture Partner, Madrona Venture Group

I’ve always had a passion for entrepreneurship, and have been intrigued by venture capital. That said, when I was leading a startup, I found it hard to trust VCs. Fancy clothes, fancy cars, and stories of them stealing companies from the founders. When we decided to sell our startup, we had two paths, a term sheet from a VC that had earned our trust (Sonja Hoel, who was then at Menlo Ventures), or sell to Microsoft. Ultimately, we were wooed by Bob Muglia and Bill Gates and we joined Microsoft, but I’ve sometimes reflected what would have happened had we stuck with it and partnered with venture investors.

One of the first people to reach out to me when I left Microsoft was Soma Somasegar from his position at Madrona. I enjoyed working with Soma as he led the Microsoft developer division (Visual Studio, compilers, .net, and more). He was always a great partner, authentic about who he was as a person, and someone I could count on to deliver great software. When he reached out, I wasn’t ready. But then a month later, I was having dinner with a good friend who is leading a local biotech startup, Mitch Gold. Mitch raved to me about Madrona, and Matt McIlwain, a managing director there.

So one day this summer I visited Madrona and spent time with both Matt and Soma- and loved it. Madrona’s core idea is that if you are going to really partner with a company from day one, especially during the very earliest phases of a company’s growth, that is best done locally so you can support the new team. This resonated with me as true – and being the leading Pacific Northwest VC, with the biggest fund to invest here, and the best track record from Amazon, to four IPOs in the past 2 years – this started to sound like a great team to be a part of. I really liked the focus on the Pacific Northwest's ecosystem of innovation.

Soon after, they offered me a role as Venture Partner. I couldn’t be more excited to meet with entrepreneurs and work with them on new technologies which inspire them, and build great new companies in the Seattle Tech Universe.

(we should really update this very cool diagram beyond 2015…)

Operating Executive, The Carlyle Group

Last fall, Satya did an interview with the David Rubenstein Show. I recall watching this and then following links to several other interviews (his recent Jeff Bezos interview is great!). I loved his authenticity, humility, and humor. And then this past April, I visited Duke, and I noticed a few buildings named after a Rubenstein. Then walking past the exalted Cameron Indoor Stadium, I saw that the entrance had been named the Rubenstein Pavilion. I wondered “Who is this Rubenstein?” And I learned that David Rubenstein is one of the founders of The Carlyle Group.

So fast forward a few months, and I am talking with Renee James. Renee and I worked together across the Microsoft / Intel partnership for years. It was exciting to hear about the progress she has made with her new company Ampere, to build a powerful ARM server SOC. We also discussed the work she had done before founding Ampere, as an Operating Executive at Carlyle. The role sounded really interesting, to consider investments in much larger, global, complex companies, and contribute experience from operating large-scale technology teams to the consideration.

Soon after, I had great discussions with Patrick, Sandra, and Cam at Carlyle. Like Madrona, these were great people with a common interest in investing in great ideas to scale businesses to new levels, but there was a huge difference. Whereas Madrona likes to lead Series A rounds of brand-new ventures, Carlyle manages over $200 billion and considers investments of hundreds of millions of dollars (or more) behind strategies to scale existing great businesses. Their value creation strategies and scale of their investments fascinated me, and I wanted to be part of the team and learn more.

Soon after, they offered me a role as Operating Executive, working with their portfolio companies on the design and execution of their technology strategies. Whereas my role at Madrona challenges me to consider how to leverage the latest technical innovations, my role at Carlyle will challenge me to deliver software at scale in many diverse organizations. I couldn’t be more excited to work with the leadership teams of great Madrona and Carlyle companies to grow their businesses.

No, Rod Stewart doesn’t work at Carlyle, but he happened to be at the restaurant where I met Cam Dyer for the first time ??

Path Dependent

One of Satya’s favorite expressions is that “strategy is path dependent.” As I reflect on my journey the past 6 months, I see that so many of my choices have led me down a path to the next set of choices. My life has been very path dependent. If I hadn’t chosen Duke, I wouldn’t have met the team which founded Intersé with me. If we hadn’t sold our startup to Microsoft, I wouldn’t have come to Seattle and met my wife, and so many of my best friends. If I hadn’t worked with Soma and Renee, I wouldn’t be joining Madrona and Carlyle. And I write here today excited about the many more junctions and paths yet to come, investing in new companies and established companies, helping them achieve new levels of success and impact. And having some fun with new great teams along the way.

-Terry

(Thanks to the old team for shipping this beautiful new black Surface Pro 6 to write this post on!)

(Thanks to Johannes Plenio and StockSnap for the header photo which reminded me of Bliss.)