Lessons From A Founder: First Year Launching A Startup (Social Enterprise Version)
By: Nathan Gunawan
Tags: Startup, Lessons, Nonprofit, Social Enterprise, Founder

Team Learnings

Empower your team to own their work and thus build resilience and creativity

Your team is likely filled with brilliant people who are creative in their own rights. Use it to your advantage. Visionary leaders are great (and for the most part, that’s how I carry myself), but don’t let vision limit and hinder you from listening to the voices of your team. Oftentimes, especially in the beginning, I was so sure that there was one single way to do marketing/build the curriculum — that I was often shortsighted to the many fantastic suggestions and criticisms my team members brought up. As a leader, one thing I’ve learned is to help the teams understand “what constitutes success”, build metrics to capture success, distance myself from the outcome, and let my teams figure it out. Even if the team runs into struggles, another thing I’ve learned is to accept that as part of the process and let them figure it out on their own instead of turning to me/my co-founder for the exact answer. Allowing your team will grow will naturally also build organic leaders that will take the organization forward with their own unique life-insights and values. You definitely can’t do everything alone — and empowering workers to be leaders is something that will sharpen the organization in the long-run.

Empower your team to be their own Elon Musks!

Take care of your mental health so members know that you’re OK and are there for them. And build mental health into the DNA of the organization

In more than one feedback session, I was told by members of the team: “Nate, one thing I would say you could improve on is just taking care of yourself. Sometimes I really feel bad scheduling calls with you or take time out of your day because you just seem so busy all the time”. That’s when it clicked in my head that I wasn’t prioritizing my wellbeing enough — to the point where it was a detriment to those around me. Members would feel like they were inconveniencing me — which was never supposed to be the point, especially since I sought to create a culture where the organization was family. Immediately, this led me to restructuring and reflecting on the prioritization of my responsibilities, how I was balancing external work and stressors, and pushed me to just be mentally healthier. At the end of the day, building a company is a marathon and not a sprint and mental health can be institutionalized by creating a culture where that’s respected. What that means for us moving forward is that Cornerstone is not going to try to do 10 things at once. Specific KPI’s will be measured, sustainable goals will be set, and innovation will happen intentionally.

Don’t do this!

Create a culture of open feedback and communication

This was actually something that I stole from both IDinsight and Teach for America — two organizations I worked for that heavily valued the immediate feedback loops in day to day work. In Indonesia, there’s often a culture of “sungkan” — which means that people who are younger are often not willing to criticize elder members in any way. This culture permeates itself onto families, businesses, and even politics. Obviously, being sensitive to culture, but also knowing that feedback was immensely important to the growth of an organization — I make sure to always integrate it as part of the DNA (during meetings, after certain project lifecycles), even if it means holding individual feedback sessions for everyone on the team. This will allow everyone to have a voice in the development of the organization.

How I conduct feedback is also stolen from one of my favorite professors, Andrew Sykes at Kellogg (who taught Entrepreneurial Selling). If you have two people, A and B, you would take turns going through these two dialogues for the other person (1) what did you do well? And (2) what could you do better/what would I like to see more of? At the end of each “feedback loop”, the person that receives feedback says “thank you” as feedback is a gift. If my Professor’s six-year-old son can do it (literally the cutest thing I heard was the fact that the son gives my professor feedback each night), then so can you!

Doing feedback automatically also results in resentment not accumulating. Oftentimes, life in startups is stressful and work is fast-paced. Cornerstone has faced times before we realized this lesson that resentment can build rapidly, and results in people feeling unproductive in meetings where they feel their voice is not heard/they feel disrespected. Encouraging a culture where people are immediately doing this day by day (literally, for example, at the end of the meeting — someone who’s leading it can ask to get feedback) will improve the morale of the organization as well.

Build a sandbox where failure is accepted and growth is encouraged

Failure is an absolutely natural part of the startup process. However, failure is not something that many people — especially from more privileged backgrounds — face too often. We’re often spoon-fed the right answer, or are afraid of outcomes that are not exactly as planned — with fear of the negative consequences of being judged, or not living up to expectations. When you’re a leader, it’s important to let your team know that those expectations and judgements are out of the window.

It’s likely that you as a leader will not know everything there is to know about business. For example, for myself, before getting into Cornerstone my experience doing UI/UX design or digital marketing strategy was at best barebones. As a younger startup filled with about 40% students, 60% early graduates, obviously our skills haven’t yet been “polished” yet. But that’s exactly why it’s OK to encourage failure as that — once again, allows members to grow and to develop organically to be the ones that carry the organization forward. Also, sometimes shit doesn’t work out. That’s a natural part of life and so if you as a leader can show your teammates that they can move past it with confidence, they’ll be more likely to trust themselves.

In addition, part of growth is not hyper specialization from the get-go, but also giving members the opportunity to get their hands dirty with many different things. If a member in Business Operations wants to learn more about curriculum building, or product management, then giving members the opportunity to grow in the ways they seek allows them to also trust you and buy in more to the organization.

Part of the Cornerstone Standards document

Never stop learning!

This is something I believe in super heavily, and it’s the fact that even as a founder, or employee, or whatever — you should NEVER stop learning and make learning a part of your daily habits. The book Range by David Epstein was one that especially struck me, as Epstein mentioned the importance of being able to synthesize information from multiple sources as the key to innovation. For instance, InnoCentive is a crowdsourcing platform that asks regular people like you and me to contribute to the solving of some of the world’s most pressing issues. And guess what? In some cases, people who are so specialized in one field and only see in that lens fail to capture the things that an outsider can see. This even plagues some of the world’s best scientists.

Thus, in that spirit, always seek to engage and absorb new forms of knowledge and content. Read books, listen to podcasts (“How I Built This” by Guy Raz and the “Lex Fridma Podcast” are two of my favorites right now), take online courses, whatever you name it — even if it doesn’t directly relate to improving your “professional career”. Just being curious about the world around us will allow you to make analogies (like how Kepler used analogies heavily to make marks on the theory of gravity and discover the field of astrophysics — https://groups.psych.northwestern.edu/gentner/papers/GentnerBrem97.pdf).

Thus, I regularly and relentlessly post learnings from content I digest on our Slack group and always encourage our members to do the same! It’s something that does not just benefit the organization but the people around.