Leading a startup towards success is no easy feat. Leading a startup through success is even harder. But, that is the life founders sign up for. They are constantly pulled in different directions, from finding a viable idea to fundraising, hiring, and scaling.
Throughout (nearly) 15 years in Silicon Valley, with countless fails and a few successes, I’ve learned the hard way that in order to be the best CEO I can be, I need to make time for deliberate actions and habits to find balance in my life, this includes (but isn’t limited to):
- Defining what your passion is
- Focusing on balance and self-awareness
- Finding great mentors and asking for help
Frankly, these are not something a first-time founder or CEO usually makes time to focus on (I didn’t), but I encourage you to do so. The sooner you can understand how to be your best self, the more you can focus on building a well-rounded company and team.
Below, I’ll dive into how to find balance and build a viable product and successful company, while you and your employees remain happy and growing.
Define what your passion is
We tend to think about finding our passion in terms of happiness and pleasure, but there’s also another side to it. Passion can come from hardships and struggles as well–perhaps even more so. In order to be a good founder and (potentially) see the success you’re hoping for, you need to have some level of personal investment and experience in the actual problem you’re setting out to solve. You need to understand the problem, and believe that you have the best solution out there for it.
My first company, Kiko, was a web calendaring tool (before Google launched its Gmail Calendar). My co-founder and I were college students whose schedules consisted of two classes a week. We were not the ideal users of our product, and therefore, didn’t fully understand what someone needed in an online calendar, much less know the best way to build it.
Whether an idea is good or bad is dependent on a multitude of dynamic variables, and one of those variables is you, the person holding the idea, and your relationship to the problem it’s solving. Seeing and investing in hundreds of ideas as a partner at YC, I’ve watched a lot of the good ones fail because of a lack of passion or closeness to the issue. This is one of the biggest reasons I started Atrium.
I like to call myself an “involuntary power user” of legal services–through starting many companies, I’ve experienced a wide range of service quality. I investigated the reason behind that and discovered that even some of the biggest players in law don’t use a CRM or project management software. When I pondered my next move after YC, I talked to dozens of attorneys, founders, and investors, and came to the conclusion that the industry needed improvement. This challenge was something I felt strongly about because of my past experiences, and it offered me a path towards high personal growth.
So look for that in your ideas. Ask if you have a deep connection to the issues your solving and if there is room for personal growth through that idea exploration.
When I talk to founders, I often see them searching for their passion at an industry level: “I’m passionate about Healthcare.” Although this is good to know, it is not what will get you through the tough times of building a company. It’s more about the passion for the actual problem and belief that you have the best tactics to solve it that will motivate you forward.
My long-time friend and former co-founder, Michael Seibel, is a fantastic example of this. Michael’s motivation and passion around YC is such that if all the startups went out of business the day after Demo Day, Michael wouldn’t feel like he wasted his time. Michael enjoys the process of teaching and mentoring. I’ve always been super impressed by this, and consider it a really good example of product-market-founder fit.
In order to be a successful founder, you need to enjoy what you do on a daily basis. You need to feel like you are making a difference in the world. Michael does that at YC, and I do that at Atrium. But, we didn’t always.The difference in a mission-driven company is that you remain motivated even during tough times. Your passion fuels your desire to continue iterating and improving. Click To Tweet
This doesn’t mean you have to like every task you do – that’s impossible for anyone to achieve. Know that no founder is good at everything, nor should be. But founders do need to be passionate about what it is they’re contributing to the company’s mission.
Find ways to be more balanced
It’s easy for founders to not do the things we know we need to do. Stating the company’s mission before every all-hands meeting, or ensuring all decisions and roles are documented. These things are critical to success, but we can easily let them fall by the wayside. Why? Because we are often accountable only to ourselves. But, when founders are focused and deliberate in their actions, it radiates out to the company as a whole.
Today, founders, especially in Silicon Valley, are able to raise their first couple million dollars without evidence of prior success, a board, or any accountability for what they will do afterward. This leaves founders without reinforcement to stick to the company’s stated mission. After Justin.tv, I had a startup named Exec where this scenario played out. We raised a seed round, but we had no board. I didn’t really feel like I was accountable to anyone, and it showed. We didn’t succeed, and eventually acqui-hired out.
So, it’s up to founders to build in accountability. And, that accountability (or lack thereof) generates real results. Two ways I’ve learned to hold myself accountable:
- Develop self-awareness
- Deal with–not dodge–the stress
Self-awareness is a critical founder trait
By nature, people aren’t very intentional about being self-aware. They just do whatever’s the default, whether it’s taking a defensive stance to a well-intended question, or speaking negatively about colleagues perceived to be low-performing.
But as CEO, everything you say to your team most likely is taken to heart. If you haven’t been a founder and CEO before, this type of influence can be shocking and dangerous if you are the type who speak out based on gut instinct. Kevin Busque said it best, “Decisions are almost always better if you wait 15 minutes, and almost every decision can wait 15 minutes.”
When a founder lacks self-awareness, it’s easy for them to step on toes, or worse, burn bridges, without even knowing it. Everyone, from executives to employees, can fall prey to this trap.
It’s important to cultivate self-awareness, and continuously strive to improve yourself. Two examples of how I plan to continue improving in this practice:
Empathy. This year I’ve made it a point to approach every interaction with empathy. This might sound odd or even awkward but, I actually believe it makes my daily life MUCH better. I think empathy is a really important seed behavior to model, both in my personal life and professional capacities.
I am going to try to start every interaction I have with another person with empathy first. This sounds like some hippie shit and 10 yrs ago I would have laughed in my own face, but I actually believe it makes my daily life MUCH better.
— Justin Kan (@justinkan) December 30, 2018
When your actions begin and end with empathy, you are able to see your behavior from another perspective, as well as increase the likelihood your colleagues will feel comfortable enough to point out where you have room for improvement.
Feedback. On that note, as a founder, you must make it a point to find people who will tell you the truth, even when it hurts. If you build a culture of empathy, it is easier to also cultivate a culture of honest and open feedback.
Many people are scared to challenge a CEO due to the perceived risk, so it is important for founders to seek out those who will highlight the things you need to work on as a leader or person. Whether that feedback comes from your significant other, your direct reports, a mentor, your board, or a mix of all the above–other people’s perspectives are key to being self-aware.
As the founder, you must lead by example and hold yourself accountable. If you want a successful startup, you have to put effort both into your company and yourself. Remember, working at a startup isn’t for everyone.
Dealing with founder stress
In the past year, I’ve harnessed spirituality and mindfulness to alleviate and prevent stress. I’ll be honest: I was very skeptical about this approach before trying it. But, I’ve found that a lot of self-improvement exercises do work if you keep at them. It’s neither rocket science nor a secret.“Your company sucks. It's never going to be anything.” … Without that harsh reality, we may never have challenged ourselves to make Justin.tv a true success. Click To Tweet
It took me nearly 15 years in Silicon Valley–after immense amounts of stress whether from failure or success–to learn that I could get help. Big surprise: companies do better when their founders get help, too.
I finally learned that becoming spiritual, going to therapy, and just generally focusing on mental health are not practices to be embarrassed about. Drawing on different resources, such as people, practices, and even phone apps can help you deal with stress at critical junctures along your path to success. Creating a healthy environment and relationships eliminates a lot of the unneeded stressors toward success. Make it a point to invest in your own well-being to become your best self for the company and your employees.
The way to get comfortable at using these practices is through repetition. I’ve tried everything, and recently developed a handful of practices that have really grounded me:
- I exercise regularly, usually 3-4 times per week in the morning. I even built a gym in my house to make working out as easy and accessible as possible.
- I try to have context changes where I’m not thinking about work. That could be designated time with family where I don’t check my phone or email.
- I meditate for 40 minutes every day. I start my day with 20-30 minutes in the morning and then end my day similarly. I started my meditation practice using Headspace and am now doing Transcendental Meditation as recommended by Ray Dalio in Principles: Life and Work.
- I discovered an app called the 5 Minute Journal. It’s a simple concept of stopping and writing down what you are grateful for every morning and evening. After a week of journaling, I was noticeably happier. I’ve now bought the app for every Atrium employee!
As a repeat founder, I am just as stressed as I was during my first company. Many times, even more, stressed, because expectations (whether from yourself or others) are higher. Adopting these practices have changed my approach to managing this stress. I also don’t believe I have everything solved–I’m constantly trying new tricks.
You owe it to yourself, and your company, to create daily habits which alleviate your stress as a founder. I know the first step is always the hardest. I first started to become more mindful and self-aware by reading other people’s perspectives–before creating my own. Here are a few books that can get you started on this path:
- The Untethered Soul by Michael Alan Singer
- The Score Takes Care of Itself by Bill Walsh
- Leadership and Self Deception by the Arbinger Institute
- Principles by Ray Dalio
Find mentors and ask for help
Early YouTube and Facebook CFO Gideon Yu gave Michael and me the best advice we could have received on Justin.tv. To paraphrase: “Your company sucks. It’s never going to be anything. But you’re going to suck down a six-figure salary for a couple of years, and that’s fine.”
Hearing that was like someone turned on a light switch. Our co-founding team realized, “Oh, that’s the trajectory we’re on. We need to do something different.” Without their advice, we might never have buckled down and pivoted Justin.tv to Twitch.
Someone else’s perspective on your success (or lack thereof) or your best next move can be invaluable. Without that harsh reality, we may never have challenged ourselves to make Justin.tv a true success. Instead, we saw we didn’t have much to lose and decided to take the risk of pivoting our strategy to fully embrace gaming, which at the time was only 3% of our revenue.
Since then–beyond Twitch’s success and advising startups through YC–I’d like to think I’ve developed into a decent advisor. And, I still rely on my own set of mentors and advisors.
But finding a support system isn’t always easy, especially if you’re not well connected within Silicon Valley. To get started, first listen to the industry, and then get involved:
- Get active on Twitter–listen and speak up
- Go to founder meetup and networking events (like ours)
- Subscribe to industry thought leaders (like Andrew Chen or the Atrium blog)
Don’t cold contact an advisor
It usually does not work to Tweet, cold email, or go up to someone who’s successful and command them to “Be my advisor.” Once you’re active in the community, you should scope out who is best to advise you, and also how and where they engage with the industry.
Before reaching out, the first figure out what type of guidance you need that you can’t gather from talking to people on forums like Quora, at meetups, or by Googling.
Once you’ve identified where specifically you need guidance, also differentiate between the need for business and leadership advice vs. personal coaching or guidance. Over the years, I’ve developed a diverse network of people who guide me–I have a therapist, a CEO coach, as well as a handful of advisors, mentors, and peers. Make sure you use each wisely and correctly to ensure it’s an equally beneficial relationship.
Once you have a good relationship, think about what you can provide back to your advisor so that it isn’t just a one-way dialogue. For example, I like to be engaged in relationships where I am learning just as much as that person is learning from me. It could be a new industry to me, or I could be learning from my advisee’s contacts. Whatever it is, strive to provide advisors with just as much value as they give to you.
This topic of finding balance amidst the pressures of being a CEO is something I’ve focused on a lot over the past year. I recently went more in-depth on Twitter into some of my daily practices that have helped to increase my baseline happiness.
A few weeks I wrote out what I've been doing to improve my baseline happiness. I originally wrote it to send only to personal friends. Some of them encouraged me to share it publicly. I hope its useful to some of you! https://t.co/GLH1aMBpZ2
— Justin Kan (@justinkan) February 23, 2019
The key is to continually be getting outside perspectives on how you’re approaching things. As always, reach out to me on Twitter or in the comments and let me know if these concepts are helpful or share your own techniques–I’d love to hear them.