I recently kicked off a series of Career Q&As with successful leaders. The goal is to provide practical advice and insightful lessons you can leverage to further your career. Next up is Scott Smith, CEO of CloudApp. He has a lot of good nuggets throughout and I particularly like his advice on spending as much time as possible feeling uncomfortable, how he balances work and family life, and the power that comes from assuming positive intent.

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Scott Smith is CEO of CloudApp, whose mission is to enable instant business communication through quick shareable videos and images for its 3 million users. Before CloudApp, Scott spent three years at Facebook developing and launching the ‘Workplace’ collaboration tool. He joined Facebook through an $85m acquisition of Parse, a YC-backed developer tools platform. Before that, he spent three years at Dyn building its sales and partnership channels. Dyn would eventually be acquired by Oracle for $600m. He’s a dad of three of his own, and foster dad too. You can find him on Twitter at @scotcha1.

What’s a book that has influenced your career or life, and why?

“The Hard Thing About Hard Things” by Ben Horowitz. In the book, Ben tells a story about when he joined a brand new startup. His daughter had just been diagnosed with an illness, and he was extraordinarily busy and stressed. He spent a lot of his time thinking about his job, and himself. One day his father came over to visit, and as they sat and talked, his father said: “Ben, do you know what’s cheap?”. Ben replied, no, and his dad said flowers. He then said “Ben, do you know what’s expensive? Divorce.” 

His father was reminding him to refocus on what was most important — his family and their well being. This idea of family as a focal point in life has always been important to me. The idea that “No other success can compensate for failure in the home” is something that motivates me, and Ben’s book really resonated with this on a very practical level. 

My family keeps me grounded and focused. But frankly, the idea of family is often understated or shied away from in Silicon Valley. Most of us here are desperate to win, succeed, or to gain some level of notoriety. I loved the honesty and vulnerability that Ben showed in sharing that story. And it’s helped me throughout my 10+ years of marriage to always be reminded of how I got to where I am, and what’s most important.

Was there an experience you had before age 21 that shaped who you are? What was it?

When I was 19 I left the United States for 2-years to do a service mission in Birmingham England and Cardiff Wales. I can still remember my very first day as a full-time volunteer. I was picked up from our training center and I was immediately taken to the Birmingham City Center “Bull Ring”. The ‘Bull Ring’, was a popular shopping center booming with tens of thousands of people walking around. My leader said “Okay, go find someone to talk to” and he quickly disappeared. I looked around shocked, and very concerned, but made the decision to say “Hi” to the next person who walked by. From the moment I entered the UK, I was perpetually in a place of discomfort being asked to do hard things. And while it was hard, this experience allowed me to learn to embrace discomfort and try things that made me uncomfortable.

How has a failure, or apparent failure, set you up for later success? Do you have a “favorite failure” of yours?

At the age of 11, I tried out for the 11 & 12-year-old Milburn All-Star baseball team. For years I had been a well recognized, and fairly successful pitcher throughout our local little league, but when the list came out showing who had made the team — my name was notably absent. That team went on to play in the Regional Championships just shy of the Little League World Series. The team traveled all over the Northeast Region, stayed in hotels, were featured on TV, and they played against some of the best teams in the nation. 

I was really discouraged and disappointed to have not made that team. It was one of the first times in my life where I really felt the weight of what a future could look like where you might not be good enough despite your best efforts. While I can’t say that moment was the catalyst that led me to be the greatest pitcher in MLB history, that memory and moment has left an indelible mark in my mind and life of a feeling I just hate to experience. Failure is important, and it helps us grow, but I absolutely hated the feeling of coming up short, and ever since then it’s motivated me to work harder.

What advice would you give to a smart, driven college student about to enter the “real world”? What advice should they ignore?

My advice would be to spend as much time as possible feeling uncomfortable. Stretching yourself to try new things, and to say yes to things you might not have all of the information for.  One of my favorite moments as a very new sales rep at Dyn (my first full-time job after college) was when they invited me to work at their booth at a conference in Santa Clara, California. I had only just recently joined the company several weeks earlier, knew almost nothing about the product, and the first person I spoke to at the booth was a high ranking technology officer at Cisco (I’m pretty sure it was the CTO!). 

As I looked around me, hoping to receive help, no other team member was jumping in to help me, and I realized I was all alone. I stretched the knowledge I had about the product as far as I possibly could, and surprised myself when we ended the conversation several minutes later. Reflecting back on this experience, it all started from saying ‘Yes’, when my VP Sales, Kyle York, asked if I’d be willing to attend this conference last minute and fly across the country.

What are the bad recommendations you hear in your profession or area of expertise?

I hear bad recommendations all the time. But I also have a career behind me full of perspective. I think the worst kinds of recommendations are given without any context. These are recommendations that someone you are meeting with tells you before they understand your situation. Silicon Valley is full of thought leaders and ‘yogis’ who tell you their way is THE way. 

I think rather than providing a list of bad recommendations, and the ones to avoid, I’ve always tried to follow a relatively simple process that my dad suggested to me years ago when I started playing little league baseball. While I was young, every year I had at least one new coach. Each coach had different suggestions. Some would tell me to throw curveballs, others would tell me to carefully avoid them because they would hurt my arm. Other coaches would recommend I change my batting stance (move forward, or backward, change my hand grip). All of the suggestions came from a place of good intent, but if I changed my approach to the game as quickly as I was asked to, I wouldn’t have been able to keep up and it would have severely affected my game. 

In the professional world, any time I hear what seems like a great idea that might require me to change, I write it down, think through it for a few days, and consider how it could fit into my current approach. I also always tend to be a Googler of new ideas. I love to find other people who might have tried out the approach and to hear their experience. But what I’ve found to be the most compelling and powerful, is to, over time, build a group of people I respect and trust, who I can ask and solicit feedback from. So my recommendation is basically to take recommendations carefully and thoughtfully but to always be open to them.

If you could go back in time to when you were entering the workforce and give yourself one piece of advice, what would it be?

Always assume positive intent. This is a philosophy that I now live by, that has largely changed my work experience. By positive intent, I simply mean, when someone does or says something, choose to believe that they are acting with the intent of good. That they are trying to provide good feedback, or they are trying to help improve your product. Never choose to be a victim. Rather than spending time or energy believing that the person hasn’t put in their best, or that they are trying to do something that is hurtful to you, spend your energy and time believing that they have your or your companies best interests in mind.

What’s one of your proudest professional accomplishments? (while this can include an obvious accomplishment, feel free to include a more personal one)

On April 25, 2013 Parse was acquired by Facebook for $85m. This felt like a significant event for me because it demonstrated that we, as a small 20-person team, had built something so incredible that one of the largest companies in the market wanted us to join them. We even received an email from Mark Zuckerberg welcoming us to Facebook, expressing his desire to include us in his larger vision for the future of their developer business. But, maybe even cooler, and on a personal level, was that Parse was mentioned during a segment of Facebook’s quarterly earnings call. On that day, I received a call from my father in law who had mentioned that it was ‘pretty cool to hear about your company in the Wall Street Journal today’. 

What’s something unexpected that has happened in your career, and how have you responded?

When Parse was acquired by Facebook, we were all very surprised. We were brought together at a small all-hands meeting, and our CEO, Ilya Sukhar, excitedly (and a little anxiously), described that we would be joining Facebook. The team instantly had a million questions. Would we need to move our office from SF to Menlo Park? Would Facebook shut us down, like so many companies before it? Did we all have jobs still? The questions were many that day, and even after our CEO patiently answered many of them, our team was unclear about our future, and you could sense a general feeling of discomfort. 

After joining Facebook, it became very clear that there were some incredible opportunities in different and adjacent parts of their business. Facebook, for example, had a larger, and more mature, developer partnerships team. Rather than trying to go about everything alone at Parse, developing relationships and partnering with that team seemed like an obvious way to continue to grow Parse within Facebook. 

While on a developer relations trip in Europe, I had dinner with a Facebook director named Julien Codorniou. He was charismatic, energetic, and I felt like he had a great grasp of Facebook and its future. After meeting him, I reached out over email, and we developed a relationship that led to me joining his team. While my initial experience going through the Facebook acquisition was unexpected, I was able to leverage Facebook’s strengths to provide myself and Parse with a larger platform.

Since entering the workforce, how have you changed or transformed?

When I was in high school and college, I tended to frequently just ‘show up’ at classes, and tests. By ‘show up’ I mean to say that I either did little or no preparation. Looking back now, I’m not sure why. But I wouldn’t be caught dead doing that today. One of the biggest changes for me has been to realize that doing your best work takes an immense amount of effort and preparation. The workforce is a grind. You commonly hear the phrase, “Choose a job you love and you’ll never work a day in your life.” I don’t agree at all with that phrase. Work is a grind, and you need to be ready to grind. While I regularly get to experience the excitement and love for my work, I also regularly have to experience the deep troughs of failure, regret, and discouragement, and I still need to press on, prepare, and deliver what’s expected of me.

When have you felt stuck in your career? How did you break out of it or push forward?

9 years ago, I moved from the Manchester New Hampshire Dyn office, out to San Francisco to open a small west coast branch. I had, in large part, moved from the East Coast to the West Coast to be closer to family. My dad recently had back surgery and I wanted to be closer to support him in his advancing Parkinson’s Disease. 

Dyn provided a wonderful experience for me, but when I moved out West, I admittedly had underappreciated how hard it can be for a small branch to feel important to a primary headquarters. Not to mention the fact that I found it incredibly hard to transition from an incredibly beautiful 20k+ square foot office in Manchester to a literal 15×15 foot room with white walls and no windows. Just a small box for me to work in. My team and leadership were now remote to me, and it was a challenge to feel included, and supported. 

I pretty quickly felt like I was on an island, and I felt like over time there would be few opportunities for advancement given the low interest in growing that office by Dyn. As I started to go on more local sales calls, I frequently heard from the CEOs that were my customers that they would be interested in hiring me. I was admittedly a little surprised to hear this, but I started to become open to the idea of finding something better suited for my career track and interests. 

What habit or practice helps you manage stress? (the more specific you can be, the better)

For the entirety of my 10+ years of marriage, my wife and I have gone on a date night nearly every single Friday. The date night is pretty simple, and it usually follows some kind of template: whether it’s dinner and a movie, games and dinner, visiting a bookstore, or occasionally knocking off a few high priority to-dos at Home Depot. 

The main ingredient that I feel that is critical, and honestly the priority of the night, is the personal, devoted, and focused time spent building a relationship with my wife. We have 4 kids all under 8, and life can sometimes be pretty wild at home after work and there are few opportunities for quiet and peace. Quite literally, they seem to try and interrupt any and every conversation we try to have. 

The date night allows me to end the week, put down my phone and computer, and to begin to release and put down some of the stress I’ve been carrying. It helps me connect with a person that provides me with so much love and support, and it helps us put the week into perspective, and go into the weekend a little more slowly. Plus, and I think this is most important, it gives you time to find out how your spouse is doing, to find opportunities to do things with them that they love, and to remind them that even if you’ve been distracted a bit earlier this week, that this time is just for them, and you can show them how important they are to you.

For more Career Q&As, click here.