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Being a founder can be challenging and lonely at times. Some of the curve balls that come your way will be unique to your business, but many are the same or similar to ones other founders have faced before. Our community of 150+ mentors, almost all of them experienced software founders themselves, can't tell you how to run your business but they can help you see a bit further into the future and share solutions to common problems. It's an invaluable unfair advantage for every founder of a calm company.

Here are a few highlights of what we have learned and conscious decisions we have made differently:

1. Every mentor has skin in the game. They are literally invested in the long-term success of your company and team.

2. Mentors have been selected for their deep experience in building businesses and willingness to help founders thrive.

3. We believe in founder-driven mentorship, not top-down advice.

4. We allocate substantial time and energy to building the connective tissue between founders and mentors, not just hoping it will work out.

Calm Company Fund thoughts on mentorship

Here are the things we broadly believe about mentorship.

- Mentors should focus on areas where they can nudge, not decide.

- Mentors who are also founders need help to consciously switch modes. Being a founder provides a ton of relevant experience, but being the primary decision-maker is a fundamentally different mode of thinking from mentoring another founder and it is key to consciously switch.

- Listen more. Literally, no matter how much a mentor is currently listening and asking follow-up questions, more is probably better. Mentors should step up and try to find practical ways to be helpful (“We need to hire a new designer can you help us find one?”) in addition to the fun high-level armchair quarterback stuff.

- Exact levels of success and/or personal brand does not necessarily correlate to a successful mentor relationship. Most entrepreneurs can think of one or two successful and famous rockstar founders they would love to have in their corner, but the most successful mentor may be the one that has more time and inclination to dig in deep with you.

First, do no harm

While almost everybody we spoke to was positive about the idea of mentorship, many had some profoundly negative experiences with mentors. Clearly, the first step to being a good mentor is to do no harm. Here are some common pitfalls for mentors.

- Being too quick to crudely pattern match. Mentorship is hard. Mentors have their own lives, problems and things on their mind. They then need to load all the context of a company’s history of priorities, experiments, and strategy into their brain for a 1-hour conversation. There is a natural tendency to crudely pattern match to their own experience—”When we faced something like that, we did X, it worked, so you should too”—share your experience but remember to work through the actual problem.

- Failing to acknowledge the full context. Startups are hard. There are constant trade-offs, uncertainty on prioritization, varying degrees of uncertainty, a long list of what has and hasn’t been tried before to crack the problem. Mentors need to continuously acknowledge that the founder is the one in the trenches, working through these problems night and day and acknowledge the limitations of their own understanding of the problem space.

- Not politely agreeing to disagree. Mentors get to be mentors because they are considered smart and successful. This can sometimes turn combative when a founder completely disagrees with a mentor’s recommendation on a key decision. In those situations, mentors need to mentally move all the way from “ok, try it and we’ll see who’s right” to “fair enough, this is your decision and I’ll support you in any way I can. How else can I help?”

The calm Approach

With all that in mind here is how we are approaching mentorship.

- Every mentor has skin in the game and is also an investor. This means every company we work with has an all-star team of operators who are literally invested in their long-term success.

- We don’t have all the answers. This is not a 12-step course where we teach you how to make money on the internet. It’s your company, your strategy, your life and we—Calm Company Fund and all the mentors—are just here to be as helpful as we can.

- Mentorship is “buffet style”… there is no curriculum and no prescriptive structure. We will provide as many great options and resources as we can, but founders, it’s up to you to tell us what you need.

- We will be investing significant time to build products to help with remote frictionless context sharing. Everything about Calm Company Fund will be remote, so it’s very important that we build and iterate on a system that makes it as easy as possible for founders to provide ongoing context about their business, challenges, strategy, and needs.

- We are the connectors, not the people with all the answers. The Calm Company Fund team views our main job in the mentorship relationship as taking the hassle out of connecting talented founders with great mentors, making sure everybody’s time is used effectively, and getting out of the way.

- Who mentors the mentors? We do not assume all talented founders will be great mentors. We plan to actively debrief and coach mentors, bring in experts to help them improve in the role with you. It’s not that we think we are experts on mentors, but there should be a central point of learning, best practices, and feedback collection. That’s our role.