The first two Earnest Founders

Earnest has been live for two months and we have been slowly working our way through conversations with hundreds of amazing founders. We make investments on a rolling basis and have quite a few more founders joining soon, but we have also backed two awesome founders in recent weeks and just can’t keep it quiet any longer 🤗

HostiFi was founded by Reilly Chase. Reilly used to run an IT managed service provider in Grand Rapids (on the side with a day job as a security engineer) and noticed that 1) Ubiquiti’s wifi platform was becoming very popular and 2) their Unifi software platform is a pain to set up repeatedly for every client. So he built HostiFi, a cloud wrapper for Unifi. The business is B2B2B, so his customers are IT service providers who deploy more HostiFi instances with each client they set up. Reilly has plans for a small suite of services built around the same model—making open source software easier to deploy—for the same customer base. A really cool constellation of Micro-SaaS. CaptiFi for wifi portal software was just launched. FYI: Power users with Ubiquiti at home can use HostiFi for free for up to 25 devices. Reilly recently sold his house in Grand Rapids and went full-time on his business and has been documenting his hardcore year here.

Callingly was founded by Leon Klepfish. Leon developed a popular WebRTC click-to-call button that found a broad user base but struggled to build a business. So he asked his users what they would actually pay for and the result was Callingly which is a platform for distributed sales and support teams to manage inbound requests for a call back. The product sounds simple: when a visitor fills out a form requesting a call, Callingly dials the distributed team until it reaches an operator, then connects the call with the requester. But the real trick is building an intuitive UI for the complex routing rules and reporting requirements that large teams and companies demand. Post-investment Leon is going full-time on Callingly while he and his wife Tyler raise their 1-year-old Calvin in Phoenix.

Both of these businesses fit a broad pattern of B2B SaaS that we really love, where the founder has spend quite some time working with or in an industry, notices a niche problem that every business in the industry has, and launches a SaaS to solve that particular problem for the whole industry. Both of these founders are inspiring makers that we are excited to be working with.

Is Earnest Capital Live Yet?

Yep. We’re not much for big splashy launches but we have quietly gone live and are making investment decisions on a rolling basis. We expect to announce the first few very soon. Please apply here or say hi and start the conversation before you’re ready to apply. Check out our FAQ with answers to common questions.

If you’re new to Earnest, we provide funding and mentorship for bootstrappers, indie hackers, and makers. We invest via a Shared Earnings Agreement, a new investing model we developed transparently with the community that aligns us with founders who want to build profitable, sustainable, calm companies.

We invest in businesses of all kinds, though we are particularly interested in SaaS, e-commerce, and scalable online education. We also occasionally put out Request for Startups briefs outlining topics we’re particularly interested in like Remote Tools for Remote Teams.

Request for Startups 1: Remote tools for remote teams

Request for Startups is a series of posts outlining a few specific theses that we feel are likely to hold good business opportunities for founders that are aligned with our goals. It’s a list of ideas, some less polished than others, and isn’t prescriptive on what problems should be solved or what products should be built. It is just a few topics we are particularly interested in and we are “tapping a tuning fork and seeing who resonates.”

A lot of smart people seem to agree that “the future of work is remote” but most investors and accelerators are very focused on their local markets, most require or strongly encourage their portfolio companies to move to Silicon Valley, NYC, London, Berlin, or whatever city they have their open plan offices in.

Earnest Mentorship

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 Earnest Advisors are. So let’s dive in.

Funding for Bootstrappers 2: What we learned

Six weeks ago Earnest Capital soft-launched by posing the question: could we build a funding model for bootstrappers? We had been working for months 1 on the technical details of an early-stage investment structure that aligns an investor with a founder who wants to build a sustainable, profitable, calm company and doesn’t want to raise traditional venture capital. Here is what we learned.


  1. …and thinking about it for years

Shared Earnings Agreement: Digging into the numbers

We received a ton of good hard questions about the Earnest Shared Earnings Agreement, particularly around “how do the numbers actually work?” Well, we’re building a fancy web calculator for it, but I thought I would just pop the hood on the Google Spreadsheet (click here to access it directly) we’ll use for it and let anybody make a copy for themselves.

Want to watch me talk about the numbers, assumptions, and scenarios behind it for 35 minutes?! Great, here you go 👇

The Shared Earnings Agreement is the output of a great discussion and tons of feedback (we’ll be posting a “What We Learned” soon) from our initial Funding for Bootstrappers call for input.

This is v1.0 of a very simplified calculator, so it is possible there are errors or things we have glossed over. Please send us any question or feedback on Twitter @EarnestCapital or Email Us

Q&A with Justin Jackson on funding for bootstrappers

I really enjoyed this live-streamed discussion with Justin Jackson. Justin peppers me with questions about Earnest Capital and certainly caught me with a few I wasn’t prepared for. For some amazing background on the problem we’re trying to solve with Earnest, read Justin’s excellent, honest piece on the Bootstrapper’s Paradox.

Help design funding for bootstrappers

Huge thank you to Joe Wallin, Kevin McArdle, and Rich Thornett for their help with this post and project.

This is a post about the technical decisions we’ve made on a new “funding structure for bootstrappers1” and a call for feedback from the founder community.

But first, we need to talk about The Problem2.


  1. Yes bootstrappers – we know, oxymoron. We don’t love the turn of phrase and it’s a work in progress.

  2. Or skip directly to the term sheet details