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An overview of how we approach mentorship here at the Calm Company Fund.

Calm Company Mentorship

Written By:
Tyler Tringas
December 6, 2020



For the last six months, I’ve spoken to 100s of world-class founders, investors, and operators. One question I have asked them all is to tell me their thoughts on mentorship: what worked and what didn’t from either side of the table. Not all of them had a strong mentor relationship in their journey, but all agreed that it was or would have been a huge boost to their trajectory.

We have made mentorship a cornerstone of our strategy but haven’t spoken much publicly about how we will approach it or who—read to the end for a preview—the Calm Company Fund mentors are. So let’s dive in.

With platforms like this, there is a strong temptation to ask every successful person you know with a big following or strong brand to be a mentor, slap their faces on your marketing material, and assume that they will figure out how to be effective mentors. We’re fighting that temptation by creating strong filters for who can be a Calm Company Fund mentor, getting a ton of advice from experienced mentors, but also making decisions from first principles designing the kind of mentorship we, as founders, would want. Here are a few highlights:

  1. Every Calm Company Fund mentor has skin in the game. They are literally invested in the long-term success of your company and team.
  2. Calm Company Fund 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 are allocating substantial time and energy to building the connective tissue between founders and mentors, not just hoping it will work out.

Calm thoughts on mentorship

First, after 100s of conversations, here are the things we broadly believe about mentorship.

  • Mentors should focus on areas where they can nudge, not decide. This is a blatant rip off of Brad Feld’s principle of Guide, Don’t Control but we agree.
  • Mentors who are 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 at Earnest.

  • Every mentor has skin in the game and is an investor in Earnest companies. 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—the 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 invested significant time to build products to help with remote frictionless context sharing. Everything about the 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. We view 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.

(A preview of) Calm Company Fund mentors

Earnest is still a few weeks away from launching, so this list is subject to change, but enough founders have been asking us who the Earnest Advisors will be. We’ve chosen to call them advisors because like a typical advisor in the startup world, they will be invested in the success of your business for the long-term.

I’m incredibly excited about this list of experienced founders and operators, all of whom have built, invested in, and in many cases sold, successful, profitable businesses. So with that in mind here is an early list of Earnest Advisors:

A note on diversity

When we started the process of bringing on the Calm Company Fund mentors, we reached out to broad and diverse group of entrepreneurs but it is no small task to find a group of folks like this with the experience, time, personal wealth, and interest to join us. It didn’t dawn on me until I first drafted this post, and several of the advisors pointed out, that we ended up with a group almost entirely composed of white men. In retrospect, we should have expected this as function of our commitment to advisors having ‘skin in the game’ and paid closer attention to this from the start, but it is also, sadly, in some ways representative of founders who have reached the top tier financial success in the bootstrapped tech world. We hope that changes.

Before publishing this post, I spoke about the issue on Twitter and got tons of excellent feedback that I’m thankful for ? (mostly in private but some in the thread below).

In light of that discussion I want to highlight a few things:

  1. I want to reiterate that the Calm Company Fund strongly encourages founders of all backgrounds to reach out to us for investment. We may not currently be a particularly diverse group but we are committed to backing talented founders of all kinds.
  2. We will be building another group we are calling the Calm Company Fellows. This is a larger “friends of the fund” group with a lower level of time and financial commitment to portfolio companies, but that we will rely on for guidance for both the Calm Company Fund team and our portfolio companies. We are already building that group, but please send us your recommendations. The Fellows group is about adding diversity of perspective in the broadest sense. In addition to having mostly white men involved we also have mostly bootstrapped founders who have already built or sold a successful SaaS businesses. That too represents a narrow view and we want folks with a much wider view involved.
  3. A central thesis of the Calm Company Fund is that access to capital at the earliest stages is something that will unleash a tidal wave of entrepreneurs who don’t come from the backgrounds that enable bootstrapping. Clearly not all, but many founders who build a business without raising capital are able to do so because they have some degree of family wealth to rely on, a spouse with a good income and health insurance, no family members to support financially, or confidence they can easily walk into a high paying tech job if the business fails. These are advantages many talented founders don’t have. We hope Earnest can move the needle on this in our own way.

Founders, if you’d like to work with this team in your corner, the Calm Company Fund is launching soon, but let’s start the conversation here.

Like everything on the blog, this is a transparent window into our in-progress thinking and not set in stone. Feedback is always welcome via email or @CalmFund.

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