I’m a first time CEO and I’m documenting things that I’m learning on my journey of creating and running my startup. In this article, I’m going to cover a lot of ground related to culture — and the inner work it takes to run a startup. Culture has a deep impact on experience of running a startup and being a part of it. If this interests you, read on.

Is it important?

A lot of people might question whether it’s even important to have a focus on culture at an early stage startup — there are so many things that have to be done, like raising capital, getting the product built, finding and supporting customers, hiring the right team, and on and on — and the runway is finite! How important is it to get this ‘culture’ thing right? Is it a froofy thing? Should people just work until they drop, for the promise of success one day?

I’ve always been fascinated by the idea of creating work spaces where special people can do special work. And I’ve recently had the opportunity of exploring a lot of different paths — prototyping, iterating, and learning from failure — to figure out what works and doesn’t work for me.

I just started my first company in Apr 2015, which has been my dream for as long as I can remember. I’d started a few companies before this, but not in Silicon Valley, they were self funded (which led to it’s own misadventures). trnql (pronounced tranquil) is a VC funded company in Palo Alto. Prior to starting this company, I spent a few years working for Google, which gave me such a different perspective about how to run companies than anything that I’d been used to prior to that.

Personal growth / inner work

The biggest challenge that I’ve faced while starting this company is personal growth. This has impacted the culture more than anything; culture has just been a reflection of this to a large degree. It’s been about really coming to terms with who I am. And who I want to be. And what choices do I make on a daily basis. And to own these choices, and be clear about them with everyone else around me.

For the longest time I was an overachiever who channelled his inner fear and insecurity of not being good enough into a very social acceptable (“productive”) outlets, and worked very hard. I just worked all the time. Whatever project I was working on, I would internalize it completely, and give it my all. I didn’t really spend much time being in the moment with anything or anyone, especially myself. And this type of behavior was applauded by society. It was all about achieving outcomes, without realizing that experience of the outcome is but a moment, and living in this way sacrifices all the moments that lead up to the outcome, and extend past the outcome. By missing all these moments by fixating on the outcome, life doesn’t hold much peace or happiness.

This bias towards burnout came to an end before I started my company. I actually ended up taking some time off from Google. I forced myself to do no work for 4 months that I took off, after I had launched design workshops at Google IO14 & a Udacity class on Mobile UX design.

It was one of the most difficult things that I’ve ever done. To wake up every day and just do nothing that is related to work. Go on a walk, think, spend time with people, do yoga, drive at the track, invest time in relationships with other people, and be myself (what is that?) Anything except for working. So this was a bit extreme, but I had been stuck in the overwork and burnout cycle for so long, that I needed some harsh medicine to restore balance.

I had deluded myself into thinking that I was a “human doing”. This pause helped me hit the brakes on this and start switching to becoming a “human being”. What does it mean to be a human being? To try and live every moment in a way that is true to self; doing things that resonate with self. To do what you love, and to love what you do. To be authentic and truthful and see yourself for all that you are (the light and the dark) and accept it; and don’t hide from yourself or anyone else. And just let go of the outcomes — they don’t help the experience of this moment. In fact, they are detrimental, because the attention we give them, takes away from this moment (which is all we have) and actually gets us farther away (ironically) from achieving that outcome.

A lot can be gleaned from what I named my company. trnql — tranquil — or peace 😀. There was nothing peaceful about my existence prior to taking these 4 months off and just settling. What followed was a period of tremendous inner change and radical shifts to the middle (for about 12 months). I have been working on restoring balance in everything that has been my life, and trnql and its culture are merely a reflection of what has been happening on the inside for me.

Values

It’s really important to have a clear vision of what culture should be at the early stage of a company. Who you are, how you show up, what you believe in are the fabric of this culture. It’s important to have the confidence to fight for this vision as more people join the company, and use this vision as a way to find the right mix of people who will make the collective greater than the sum of its individual parts. For me this meant the following things:

  1. believe in what I do, and find others who believe in it as well,
  2. focusing on building a healthy relationship with self and others,
  3. allowing myself and others breathing room to run experiments and fail — ie, play,
  4. stop focusing on the outcome — let go of the ‘exit’, let go of whatever external validation or status I was seeking; basically let go of ego, control, and righteousness (the belief that the world owes me anything).

Preventing burnout

In my mind, failure and learning are synonymous (if you’re doing it right). Just like wisdom and pain :). Startups are risky. That is by definition. We don’t exactly know how the unknown is going to present itself. So, to bring more fear and insecurity (which feeds ego, and this idea that we have control) into this situation is just very dangerous. There is too much fuel there already for an explosive mixture. I believe in what I do. And I want to work with other people who believe as well. That was one of the most important elements to get right at trnql, to ensure that the right mix of people are joining the company.

I also found people who are very hard working and dedicated naturally. The key with motivated people like this is to ensure that they don’t burn out! Our culture really encourages this idea that people should just work themselves to the ground for short term productivity gains. So many studies have shown that you can operate in this way for about 2 weeks and then productivity just starts to plummet, and the harder you push, it just keeps going down. This is a not a good way to live and is not a good relationship to have with oneself, or with anyone else. And how do I keep burnout away? Make sure that people have space to breathe and not become overly fixated with deadlines and specific outcomes, which leads me to the next point — play.

Play vs Depression

At the start of the company, I was pushing hard as usual and trying to get things done, and everything was a mad dash to the finish. This is how things operated for about 4 months, and it was awful.

This wasn’t the way in which I had envisioned running my company, and this isn’t how I wanted to live my life either. So I really had to find the strength to fight for what I truly believe in. And I changed things. And made it so that everyone at the company knows that they are empowered to run experiments on their own or as a team, to bring in different perspectives and insights that would have been lost otherwise.

We also know that there is no punishment for the failure of these small experiments — only things we learn from and iterate on to make things better. Aka, play.

By play, I don’t mean having foosball tables, and playing ping pong. I mean that people are empowered to bring their ideas to life in a way that they see fit, once we have talked about the parameters of the experiment they are running, what the scope is, timeline is, and what results we may or may not expect.

Honestly, we are just being realistic about how venturing out into the unknown works anyway. We don’t know how a piece of technology is going to work out exactly — not until we try and tune and tweak it.

This culture of play has really unlocked so much innovation at trnql. Eg: we discovered that we should invest in this online challenge to find interesting developers who can discover our technology and make great apps for end users. Eg: we tried different things at our meetups and realized that some formats didn’t work at all, which was a great gift, because we tuned our formula so that we know how to reach what audience and for what goal. And it turned out at the end the answer was for trnql not be involved in these meetups at all!

These are things that are impossible to learn without trying experiments and learning from their failures. Success often isn’t a good teacher, but failure can be, if you know how to handle it 😀.

Focus vs distraction

Another element of effective play is to kill distractions! When folks are fixated on outcomes rather than the journey, they tend to optimize for local maxima, and just make really short sighted decisions. Removing these outcomes from the mind releases it, and allows it to be more creative, focused, effective, and more efficient.

The creative process isn’t driven by outcomes — it’s driven when it’s nurtured and given some space. By clearing things that hinder the journey, which includes this outcome-driven mentality, distractions are also cleared. And we can focus on what is truly important in the moment. And the next moment. And so on.

We are optimizing the process for maximizing the moment, rather than sacrificing the moment for some outcome (that won’t be achieved on this path anyway).

Another aspect of removing distraction is having a clear vision of what you do want. This doesn’t have to be crystal clear, but there has to be enough there, such that this vision doesn’t look like everything and the kitchen sink thrown in there. There’s a lot of discipline and pruning and saying “no” that goes into crafting this clear vision, and communicating it to everyone; along with saying “no” to all the needless distractions.

For trnql, I have a clear vision of what I want to do, and how I want to do it (without really thinking about an outcome like an exit) — which might not be the case with other companies. I have a unique background because of my skillset — coding, advocacy, sales/marketing, etc. which has allowed me to remove distractions, and also look at the high level and low level at the same time; my team is benefiting from past work and experience.

Empowering people

When you give people the space to play and a clear idea of what is expected of them, and the leeway they have to fail, and what scope of things they are allowed to try, then you have effectively empowered them! By rewarding the willingness to fail, to learn from failure, and to try again, by being an example that they can follow, you can cultivate empowerment in the team. This is what leads to great process efficiency, since so much needless communication and collaboration is cut out. When people are empowered and they take on the role as an owner or leader, then they are able to do so much more in their role, than they would if they didn’t have this feeling of empowerment.

This is difficult for some founders or micromanaging CEOs to do. A lot folks want to retain control (since this is tied to their ego), and this is not really empowering for the team. By giving up direct control, but retaining diffuse control, and being clear with expectations and the vision, it allows the right mix of chaos and planning to maximize creativity and efficacy of execution. It’s a delicate balance and I can’t say there’s a fixed formula for this. Depends on you, on your team, on your product, etc.

Mistakes made and lessons learned

I made a lot of mistakes with hiring early on. I worked with friends and family and all this ended badly (as it was difficult to set clear boundaries and expectations with them). I had to let people go, which was painful, but I learned quickly the importance of getting the right people. Not people who are spectacular individual contributors. But people who are willing to work with the team, willing to grow, and also very good at what they do — but are willing to learn. This is counterintuitive at times, since it’s easy to think that simply adding more spectacular individual contributors will get you there. Nope. Less than spectacular contributors that work well as a team, under good leadership, will get you there much more quickly & smoothly than you ever thought was possible.

Full circle

So the culture at trnql paid huge dividends in the last few quarters with our big push to get both Android and iOS SDKs out of beta and into general availability! We worked really hard for 9 straight weeks. No one got sick. No one took a hit on their relationships. No one lost a weekend. No one had a sleepless night (not due to work anyway). And we ended up doing the smoothest product launches that I’ve ever experienced in my career!

And all of this was from a commitment to play — to not freaking out when something didn’t go according to plan, and having the patience and resilience to pivot and come up with something different (and sometimes even better) that what we had originally envisioned.

It’s about finding this delicate balance between exerting one’s will, but keeping ego out of it, so that we can bend with what the universe puts in our path.

Human being and not doing

And this all comes back to me. The company’s culture is a reflection of who I am. If I want to see something in my culture then I have to do the inner work to make it happen in myself.

My team of 5 looks to me for direction, and mimics my behavior. When I endorse something and encourage it by doing it, and leading with my example, then it becomes part of what everyone does.

Eg: we had gone back and forth on adopting slack for months. Then I saw the CEO of slack speak at a VC event that trnql’s investors held (we have the same investors as slack), and I loved the story of slack. Later on that week we were using slack, because I set the example that we get off of Google Hangouts and move to Slack, and favor it over IM and email! And it took about 24 hours for everyone to get on board (the advantage of a small team).

Along the way, I’ve been pushing boundaries and getting out of my comfort zone:

  • I’ve taken up dance as a way to understand how to embody mindful movement and communicate with people without using words.

  • I drive at the race track as meditation, to understand that everything changes all the time and the way is to adapt and leverage in order to build forward momentum; and not to let some bad moments stall the momentum or break the rhythm/flow.

  • I practice Yoga and Chinese Internal Martial Arts (TaiChi, HsingI, Pagua) and healing arts, as a way to make sure that my body is healthy, and that my mind and my body are in sync.

  • I focus on being a more sociable person, and am focused on people. I used to think I was a technologist. Now I think of myself as a humanist. It’s all about nurturing the right relationships, and showing up as your authentic self (which isn’t easy and takes courage). To this end, I’ve even started a group of like minded people who are looking for community and deep connection in Silicon Valley called SV life hackers. It’s an in person group where we can share lifehacks and other wisdom that we have gained by experimentation and experience that can benefit others in concrete things in their current lives.

  • I make sure to create space in my life, by not being overwhelmed with work and become overworked and burnt out. And this is a daily practice, and while it gets easier as new habits are formed, there are always challenges, and new twists and turns that show up on the journey. But if you can fixate on enjoying the journey instead of constantly thinking about when you are going to get there, then play and building relationships, then investing in self and others will naturally come into focus and become a healthy way of being. It’s easy to get distracted by the big payoff, and just burn everything to get there. But there is more than one payoff in life . There are a string of payoffs, and unless we look at life as a string of small to large payoffs, instead of a bunch of emptiness until we get to one big payoff, then imbalance and burnout are going to result.

What’s next

I know many challenges lie ahead. I have many tools to tackle these challenges. I have a great team. I have great friends and family that can help me be the best version of me. I’m investing in myself and treating myself in the way that I want to treat others — with acceptance and love. It all starts with self. If you feed the beautiful parts of yourself, rather than putting all your attention on the ugly bits, then you will become the best version of you. It’s the universal law of attraction — whatever you put your attention to, will be drawn to you, and you to it.

I will write more posts on this topic. And document the journey I’m going thru at trnql as a young CEO.

Don’t stop believing. And hold on to that feeling.

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