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Laura Thompson is a strategic go-to-market and product marketing leader with 15 years of experience. Laura started her career as a Product Marketing Manager at Google before transitioning internally to X, The Moonshot Factory, where she prepared moonshots for contact with the real world. At X, Laura led all things non-technical and worked directly on products like Wing, a delivery drone service and now a multi-billion dollar company, and a smart contact lens for diabetics, which was licensed to Novartis.
Laura then went on to become an investor at GV before joining a couple of startups as an executive. Most recently, she built the Execs On Deck community at On Deck, which helped hundreds of top leaders 10x their careers and impact through executive coaching, resources, and a supportive peer community.
Kieran: Hi Laura, thanks for joining me. Do you want to introduce yourself?
Laura: My name is Laura Thompson. My career obsession is turning innovation into viable companies. I spent almost a decade at Google. As part of X, The Moonshot Factory, I launched radical innovations like self-driving cars and delivery drones. I then dove into the startup world, first as an investor at Google Ventures and, most recently, building the Execs On Deck community. Throughout my career, I’ve worked with hundreds of companies, big and small, on go-to-market, user discovery, and building experiment-led companies.
Kieran: I want to start a little bit earlier. I saw you started a company in college called RUNA, which made clean energy drinks. What did you learn from that experience?
Laura: I started RUNA with four friends in what was really the only entrepreneurship class at Brown at the time. Our professor, Danny Warshay, still a fantastic friend and mentor, was obsessed with user discovery, user research, and getting out of the building. So, my biggest lesson from RUNA was falling in love with the power of user discovery. My memories of that time were getting kicked out of Whole Foods multiple times for loitering in aisles and asking people questions. We also flew to Ecuador and did this crazy multi-day hike (I ended up in the ER in Quito, but that’s a longer story!) to build the first partnerships with the Quechua people and get it off the ground. Since then, I’ve worked with tons of companies around user discovery. I always get pushback from people saying we don’t have time, or Ford said people would’ve asked for faster horses. The reality is, if you want to create something radically innovative, you don’t need to make exactly what your users ask of you, but you must deeply understand the psychology and needs of the people you’re building for. That was key to RUNA’s success, and doing that hard work upfront was key to everything else I’ve done since then.
Kieran: After graduating from Brown, you started your career at Google. What influenced that decision?
Laura: Two things. One was that I knew I couldn’t stay with RUNA. We had good momentum, but only two of the original five folks stayed on. I had come from very humble beginnings. By the time I graduated college, I had lost both my parents. I needed to support myself fully financially. There was no safety net. If you have some co-founders in that position and some who are not, it’s just not going to work. So, I knew I had to get a job. Two was, like many college kids who don’t know what they want to do, I was very focused on consulting. At the time, Google was a weird thing. It wasn’t a typical career path. I applied for Google because I thought the interviews would be good practice as they were the week before my McKinsey final round interviews. Then, when you get the job offers, they fly you out for the weekend. I was super impressed with the intelligence at Bain and McKinsey, but when I got to Google, my mind was blown by the obsession with impact at scale. I got to trail around Jason Toff, who has had an amazing career, unsurprisingly, since then. He was a year ahead of me, and he came up and launched this whole program by himself. They had to pull me off campus at the end of the weekend. I was like this is it; I’m in.
Kieran: You eventually worked at X, Alphabet’s moonshot factory, creating radical new technologies to solve some of the world’s hardest problems. Many people who work in startups don’t think you can innovate within a big co (example). X, the moonshot factory, seems to be an exception because many projects have been successful and spun out as independent businesses. What do you think Google got right when they set up X? What can other large companies who want to innovate learn from them?
Laura: The biggest thing that X did well was incentives. If you ask most people if they want to work on something innovative, high risk, where you will fail and be encouraged to experiment — people will nod their heads vigorously as if they’re in. But the reality is that failure is painful, and we are conditioned to avoid it. X was very thoughtful about that early on. They constantly reminded people and demonstrated that they were serious about wanting people to experiment and, at times, fail. Google is not going to ding you for it. Instead, we’re going to celebrate it. On a small scale, we did things like calling early drafts of documents v0.crap to encourage people to share their ideas as early as possible. We had these crumpled paper stickers you would get if you killed an idea that were like badges of honor for your laptop. On a bigger scale, for all the projects I launched there, I think I’m most proud of leading the first extensive shutdown for X. Essentially, the team themselves decided to shut down their project; we gave everyone a big bonus, had a big party, and helped them all find new jobs. The difference between companies that say they want to innovate and those that really do is almost exclusively incentives.
Kieran: X builds projects outside the scope of Google’s product offerings. So, X doesn’t leverage Google’s distribution advantage. I think that was a big risk when they set it up, but it seems like it’s working. Can you talk more about some of the challenges and advantages of the setup and if there is anything you would have done differently?
Laura: X is 13+ years in at this point, but it was always a long-term bet. So, in many ways, the jury is still out on whether this model works. I think being separate from Google was very helpful in that most people at the company, whether big or small, should be working on something that has a reasonable chance of success. The projects at X, by design, do not. Regarding projects, some of the earliest ones got moved into Google, like Google Brain, which is the basis for a lot of the AI work at Google right now. One challenge was that people were skeptical or worried about Google’s affiliation at times. I saw that while working on Wing, a drone delivery company. There are pros and cons, and the reality is that it’ll take another five to ten years to figure out whether that was the right call.
Kieran: While you were at X, you delivered more than 100+ speeches and presentations to executives and leaders about how to think radically differently about their products, companies, and even career trajectories. What were some of the key topics or findings that you shared?
Laura: One theme that came up a ton was the idea of measuring success by units of learning. The reality at X was that most of the things we worked on would not work out. Our success depended on how quickly we could figure out that something wouldn’t work, whether due to tech, regulation, or the laws of physics, and move on to the next thing. So, we needed to work on the hardest parts first to learn that as fast as possible. Astro Teller, who is the Head of X, had this very memorable analogy that we came to call the #monkeyfirst principle where he would say “If you were going to teach a monkey to recite Shakespeare while standing on a pedestal, please do not start by building the pedestal.” So, we talked a lot at X about whether we are doing #monkeyfirst here and what the hardest part of the problem is. I think the reality is that it is true for sort of just about anything. There is a huge upside for people willing to learn the hardest lesson first, whether in life or careers – startups or big companies.
Kieran: Later in your career at On Deck, a startup building communities for talented and ambitious people, you helped executives and leaders find opportunities that could lead to a more impactful career. What were some of the exercises or frameworks that you used to help guide these individuals?
Laura: So, I started Execs On Deck to solve my own problem when I left Google and jumped into startup executive roles. I loved the intensity, pace, and mission, but I missed having a peer community to learn from. I found that there were tons of communities and resources for founders, but there’s nothing for senior leaders in startups who are critical to the success of companies. So, the idea with Execs On Deck was to bring together hundreds of the top, best-in-class leaders from around the world. We had coaching and resources, but most importantly, we had this incredible peer community to ask things of. Regarding frameworks and resources, I think the reality was that 99.9% of the benefit was that it was a place where people could talk about anything—so, starting an LLC for consulting on the side, hiring, firing, where to go on vacation, how to make time to take a vacation, really anything. One of the earliest things people struggled with was leveraging and making time for community. Fellows came in with killer networks already, and then they joined hundreds of other people keen to network and build community, but it’s tough to make the time with a big job and a busy life. So, something that we did right upfront, actually based on something I’ve been doing for a million years, is I have a calendar hold for 15 minutes every single Friday with myself called “Touch Base.” I use that time to reach out to someone I haven’t talked to in a long time. There is no ask or specific goal, it’s just an opportunity to reconnect with someone I want to keep in touch with. That is something that I shared with them, and started by encouraging fellows to add a small amount of structure to how they leveraged your communities both inside and outside Execs On Deck. Simiarly, adding a small amount of structure to things that are sort of nebulous like career development and the job hunt, is very useful. So, something that we talked a lot about within EOD was doing one thing for your job hunt a week — commit to a coaching session or a workshop or one touch point with someone — as a way to progress and the same with career development. To make what felt like more linear progress out of what are inherently messy and non-linear processes.
Kieran: What is something that is maybe underutilized by executives when searching for a new job? What is the number one thing you’re recommending to these people?
Laura: This may be a hot take, but I will stand by this: I think storytelling is the number one unlock for the executive job search. The reality is most people are terrible, understandably so, at telling their own story. This is especially true for executives because you’ve had a much longer career and accomplished an interesting mix of things, and many want to pivot because they want to find a steep learning curve again. It’s tough to get good at telling your story. You can do that by practicing with peers or with a coach. The solution can be any number of things. But I think getting serious about killing your storytelling piece is the unlock for most executives.
~ three broad questions to close us out ~
Kieran: You’ve accomplished a lot throughout your career and worked with startups in various ways – as a founder, incubating at X, investing, advising, etc. — which aspect has been the most enjoyable and exciting for you?
Laura: If you ask a bunch of people what the best moment in their career is, they will inevitably describe a time when they were part of a small, high-trust team working really hard on something that felt big and meaningful, even potentially impossible. Since I graduated college, my north star has been to maximize my time in those types of moments. Because I had that clarity, I could sort of pursue, to your point, a wide variety of opportunities, see things from various angles, and ignore some of the stuff that I don’t care as much about, like job titles. I don’t know if I’ve had a specific career highlight - the early days at X were certainly magical and unique. I also feel that way about RUNA and even the early days of Execs On Deck. So, I cherish the moments when I’m building something new and important with brilliant people.
Kieran: I think everyone tries to find the balance between career trajectory, compensation, and finding something that they enjoy doing. It is often very hard to find all three. How have you tried to balance these things at various points in your career?
Laura: My focus in my career has been on meaningful work. For better or worse, I have been less worried about trajectory and other things. I think one thing that’s worth noting is I’ve always been a bit of a personal finance geek. I taught personal finance workshops for about ten years at all the big tech companies and many startups. Because I came from humble beginnings, I was very focused on it. At Google, I lived on less than 20% of my income for the first six or seven years and invested the other 80%. Now, that approach would fall under the FIRE movement. At the time, people just thought I was very weird. It’s impossible to talk about money without talking about privilege and luck, and yes, Google’s stock did well, and that was helpful. But, for people I mentor, I really emphasize getting personal finance right early in your career and investing. It buys you much more freedom to create a career you’re excited about, even if it’s not vast amounts of money, just due to compounding.
Kieran: Yeah, I wish I got into personal finance way sooner. I started only three years ago, but I wish I had taken a class sooner, which would have opened my eyes to just how important it is to start early.
Laura: And the reality is it’s never too late. I’m also still learning. I took the CFP classes during COVID-19 and still do a ton of informal counseling around personal finance. I think people are surprised because in Silicon Valley, we talk about lottery tickets and big exits and being employee #3 at Facebook and whatever, but the reality is for most people, you can buy yourself a good amount of freedom by just being diligent about it over a chunk of time.
Kieran: Last question: what career advice you learned along the way still resonates with you today?
Laura: I think a lot about consistency and the value of compounding. I wrote something about this on LinkedIn the other day. Years ago, when I had just started in VC, I was at dinner with a colleague, Tyson Clark, who’s an amazing VC who has since passed away, unfortunately. Honestly, I was ranting to him about how frustrated I was seeing, up close, all the VC dollars go to essentially white men. I couldn’t do anything about it; it was incredibly infuriating. His advice at the time, which I kind of rolled my eyes about, was look, you and I are not going to be able to change the system, but at least what you can do is commit to a small, repeatable action, that will make things 1% better over the long term. I ended up taking his advice and committed to doing 2-3 calls with diverse leaders every week with things I could help with — go-to-market, storytelling to raise money, and navigating non-linear careers. I realized the other week that I’d been doing that for seven years! I’ve kept that promise for seven years. I ended up looking at my Google Doc, where I keep notes, and it’s 150 pages long from those conversations. I’ve had more than 600 conversations. I’ve met so many interesting people, and it gives me an endless supply of anecdotes that I can use in my work, and it’s been really meaningful. Something people tend to forget is that lives and careers are hopefully quite long. We tend to overemphasize hacks and underemphasize the power of doing things consistently that compound.
Kieran: Yeah, I love that advice, and it’s also something that I’ve been thinking about every day. Half the battle is just showing up and getting a little better, and it will pay off over the long run. So, thinking long-term about your career is super important for everyone. Thank you so much, Laura, for joining me; I really enjoyed this.
Laura: Yeah, thanks so much for having me. It was fun.