I am reluctant to call someone a ‘friend’ unless the relationship has crossed the threshold honoring the depth of commitment behind the designation. By that framework I started out as a ‘fan’ of Javier Soltero way before we became friends. It was his mobile productivity startup Acompli (later acquired by Microsoft) which first caught my attention. The state of email and calendaring apps at the time was depressingly basic despite the importance of them in day-to-day work, so I was an enthusiastic adopter of whatever developer was building for power users and not simply ‘making an app version of the existing web interface.’

Our journey from ‘fan’ to ‘friend’ had a substantial time lag – an intermediate period of friendliness – but I’m comfortable we moved to the F word a few months back after a nice walk in Marin. It was our first time outside of DMs, emails, texts, and we learned a lot more about one another. That increased my desire to continue probing, and, share it here, via Five Questions. There are some real gems about technology careers, entrepreneurship, and so on. Enjoy!

Hunter Walk: We both started our Silicon Valley lives in the late 90s, you most notably at Netscape, which was obviously important and influential. Did it feel that way in the moment – that you were at the origin point of something quite transformational – or more so only in hindsight? 

Javier Soltero: Short answer is yes, it felt like something amazing was happening and it was great to be a part of it. On a personal level, the idea that I had started my first professional job in an industry and an area that I had been so passionate about since I was a kid growing up in Puerto Rico. I suspect a lot of people my age who entered the industry at that time and who were not from California felt similarly. 

More broadly, that time represented an interesting time for the industry and its relationship to its enterprise customers. My time at Netscape coincided with the moment where almost every company in every sector had determined that it needed to invest heavily in internet infrastructure (email, calendaring, proxy servers, application servers, and more). However, as I spent my first year working in Netscape’s nascent professional services group, it became clear that most companies were neither ready to embrace this big change in their approach to technology nor particularly clear as to why they were doing it in the first place. It took at least another 5 years and the dot com crash for this to sort itself out. 

HW: I’m sure you get hit up for career advice all the time. Are there things you tell people to consider, or frameworks you recommend, which apply almost regardless of the circumstances? For example, I believe it’s really important to know what you’re optimizing for when thinking about the next phase of your growth. 

JS: The most general yet useful bit of career advice I often give is for people to look at the progression of their career as a story, and do their best to make the story compelling. This applies to the decisions that people make about future opportunities as well as the way they talk about and derive wisdom from their past experiences. 

I’ve noticed that many people who are evaluating new opportunities understandably focus on the specific change between what they’re doing now and what they’d be doing next. I encourage people to think through their larger story, how they developed their interests and specialties, how they evolved as leaders/managers, what they learned from their own mistakes as well as those of others around them. Whether they realize it or not, everyone has or is developing an interesting story. It’s critical to learn how to tell it and how to evolve it over time.

The most of the critical choices I made in my career were made with a healthy amount of emotion and gut and would not likely survive close, rational inspection. Yet each step in my career, from my early mistakes in college all the way to the work I’ve done at Microsoft and Google all tie together in a way that, at least to me, tell a much more interesting story about how I’ve developed over the years. 

Years ago after Microsoft acquired Acompli I was asked to come tell my story at Carnegie Mellon. Their initial expectation in extending the invite was that I’d go up there and say something along the lines of “well, I went to this great school, got great grades, moved out west, started and sold a couple of companies and now here I am”. As I reflected on what I really wanted to say I ended up having to warn them that my story was a bit more complicated, starting with the fact that I got such horrible grades my freshman year that I was asked to take a year off to “re-evaluate my goals”. In the end, I got my act together, returned to CMU and moved on from there, but I could not pass on the opportunity to tell the story in a way that to me really highlighted the lessons. 

The talk ended up being about how at each step of what looked like a perfectly planned and well executed career, there had been doubt, mistakes, and irrational risk taking that really provided the lessons that are worth sharing. The talk was called “I never learned to spell successful” (which is true, as a non native English speaker I often drop an extra L at the end). 

HW: You’ve been a startup founder as well as an executive at larger tech companies. When hiring into teams in each circumstance how do you assess fit differently? Especially if, say, it’s someone who has only done startups making the case they now want to be at a BigCo, or even more commonly, the BigCo person wanting to join a startup. Do they ever really know what they’re getting into?

JS: I’ll start by saying it’s absolutely critical to know whether someone has or hasn’t worked in a startup before and to understand whether the majority of employees at a startup have prior startup experience. I don’t believe that lack of startup experience should rule someone out from a job at a startup. People who have the right skills and experience can be successful in both environments and just need to have their expectations about the job calibrated accordingly on their way in.  

Even more important, the hiring manager and the founder/CEO should ideally be aware of the implications of having an employee base where a large number of people have never been through the experience of being in a startup. The uncertainty and risk are obvious factors, but perhaps even more important is the level of visibility and information that employees at startups tend to have about how things are going. The founder/CEO has to make a choice about how/when/if to be transparent about the things that are happening (good and bad) and the level of startup experience within the group will be a critical factor in whether the decision to be transparent turns out to be a good one. 

Here’s a couple of examples of this from my personal experience:

As a first-time CEO of Hyperic back in 2007 I had made the choice to be very transparent with our growing team about the financial objectives of the company and specifically the quarterly sales target. As the company continued to grow and meet or exceed these targets we chose to celebrate the progress openly with the company like many other companies do. At some point I noticed a change in our culture. People in the company seemed to be behaving in a way that suggested we had somehow “already made it” and were starting to show signs of entitlement and lack of perspective. As a person who bootstrapped the business with my co-founders for the first 2 years, this did not sit well with me. I ended up choosing to ask two simple questions at the following all hands: 

One, who here has worked at a startup before? 

Two, what percentage of our paycheck comes from customer revenue vs. investor dollars? 

I learned most people had never worked at startups and pretty much everyone thought more than half their paycheck came from customer revenue. Both of those questions and the conversation that followed proved to be a very effective way of preserving the drive and energy in our culture while keeping folks grounded in the reality of early stage companies.

Years later as CEO of Acompli, I knew I had hired an excellent team of startup veterans, but crucially none of them aside from the founders had seen success. In fact most were quite jaded about prior startup experiences that resulted in companies going out of business. Once again I chose to be as open and transparent with the team as I could from the very beginning and when the time came where we were in active conversations with Microsoft about an acquisition, I made the tricky choice to level with the team about where things stood throughout a pretty unique negotiation process. Through the negotiation, we passed on offers that would have been very consequential to every employee but did not reflect the real value of the company. As we discussed this with the team (something that is HIGHLY risky) I was surprised by how strongly the team felt about the decision to only sell the company for the right amount and the right terms. In that same conversation, I was open with the team about how difficult it was to ask for so much money for a pre-revenue company that had only existed for 18 months. Our iOS lead weighed in with a simple observation: “Javier, how many Microsoft apps do you have on your home screen? Answer: None. How much do you think it’s worth it for Microsoft to get a slot on the home screen with our app?” The rest, as they say, is history and I’m proud to say that hundreds of millions of people have Outlook Mobile on the home screen of their iOS and Android devices.

HW: Google’s former CEO Eric Schmidt (who, disclosure, led the company for most of my tenure and was someone who really helped me along the way) was recently quoted in a class at Stanford as basically saying the company had gotten soft (although he clarified this later) You were at Google HQ during a pretty charged 2019 – 2022 period – was Eric’s critique fair?

JS: I only experienced 2019-2022 Google, so it’s hard for me to compare that against what Eric and many others experienced in its first decade of existence. I will say that a lot of tension arose from Googler’s expectations that the company’s culture had to be exactly the same as what it was when the company was one fifth the size. Even people who never witnessed that era of Google seemed to have a strong allegiance to customs and norms that simply don’t scale to a company of over a hundred thousand employees. Yes, there are elements of a company’s culture and values that endure even after decades of spectacular growth, but the way those elements are manifested and the way they influence the day to day operations of the company has to constantly evolve. 

To put it in perspective, I joined Microsoft at a critical time in its history, within the first year of  CEO Satya Nadella’s leadership. It was a time of tremendous change and tension within the company. As a leader who came from outside, I encountered plenty of tension and resistance and even more support and curiosity from even the most tenured Microsoft employees. In the end what made those first few years possible and gave us the Microsoft that exists today is simple: Satya made it clear to the company that we had to change. Microsoft’s culture enabled that message to be heard loud and clear and made the space for many important changes to occur. Google, by contrast, has not been as clear about that. 

HW: One last, more personal, question. What’s something you care about that you wish more people understood or supported? 

JS: Simply put, the impact of technology and device use in children and teens. I know this is a topic that many people are at least hearing about, but I truly wish this was better understood. As a career technologist, I am and always will be fascinated and supportive of any technology that can help us live better lives, achieve more, be entertained etc. However I also bear witness both through my own children as well as those I see around me that the use of devices as a distraction for children requires real discipline and a better understanding of how to employ the parental controls in order to avoid the many negative effects that excessive phone and tablet use can have on kids. 

Most parents agree that they’d love to be in more control over the technology used by their children but few I’ve come across are even remotely familiar with the basic things you can do to control the amount of time spent on the phone as well as the apps they have access to. I’d know we’re making progress when we see Apple and Google highlighting screen time/parental controls in their commercials with the same level of energy they devote to the quality of the camera in their phones.

Thanks Javier!