The Purpose & Theme of the Founder Summit

The theme and purpose of the inaugural Founder Summit is: having the conversations we’re not having. As founders we are fire-hosed with tactical and strategic advice on acquiring customers and building products. We have enough books, blog posts, and podcasts to fill every waking moment with tips for building a company. But there are still some conversations we are not having. These are often the kind that can only be had with other founders in an environment of candor and openness. Conversations like:

  • What does it mean to live a mindful daily life as a founder?
  • How do I fire employees with grace and keep a team motivated through change?
  • How can founders balance their identity as an entrepreneur with their other identities? How can we strengthen those other identities in a way that helps our company and team?
  • How can we be better mentors to our employees and communities, and better coaches to our peers?
  • What kind of personal finance strategy makes sense for founders?
  • Why… really… are we actually doing this?

Does that mean this will be non-stop tough, heart-wrenching conversations? Absolutely not! We believe that the best substrate for these conversations is… fun. Most attendees will be flying to Mexico City, many for the first time, and expecting an adventure. We intend to deliver. Venues, experiences, food, culture… we’ll do our best to create a genuinely fun environment that creates the space for openness and connection between founders.

How will you know you’ve had a successful summit? Actually this one is easy. The reason for having these conversations in a large gathering of founders, rather than say in a 1-on-1 coaching session, is that the goal is simply to create meaningful relationships between other founders. One of the conversations we’re not having (at least often enough) is that being a founder can be lonely at times, doubly so if you’re running a remote company. The real goal of Founder Summit is for everybody to open up and in a relatively short period of time create or reforge lasting relationships with other founders.

Why state the purpose here? To help guide the rest of the decisions but also to help folks determine if this event is not a fit for them. If you are looking for non-stop tactical content on SEO, agile development, content marketing, or Facebook Ads, you will not find that at the Founder Summit. If you’ll be meticulously calculating the ROI based on the number of warm leads you bring back or business cards you’ve handed out, you’ll be disappointed. If you want to have an experience that will reinvigorate you for the whole year, have discussions that will affect you and your company’s trajectory over decades not quarters, and make a new founder friend or two, Founder Summit is for you.

You can read more about the Founder Summit here or start the pre-registration process below. We’ll begin releasing the first batches of tickets on Nov 3rd. If you’re interested to come please pre-register now as we already have substantially more pre-registrations than total tickets available and will be releasing them on first-registered, first-served basis.

PS – this post was inspired by the excellent book The Art of Gathering which I highly recommend for anyone planning an event.

Why we invested in MemberSpace

At Earnest Capital, we are big fans of platforms that enable entrepreneurs to build profitable, scalable, remote-friendly businesses. MemberSpace enables nutritionists, personal trainers, educators, and entrepreneurs of all kinds to build a membership business on any website.

Although the category of enabling members-only sites is not particularly new, we think MemberSpace is unique in a couple of interesting ways.

Build a membership business on any web platform and take it with you

Like so many great products, MemberSpace began as an agency focused on building Squarespace sites for businesses. The co-founders, Ward and Ryan, listened to their clients and heard loud and clear they needed a way to build membership businesses on Squarespace. They productized the results, and as they perfected the product, slowly transitioned their team to a full-time focus on MemberSpace.

But they cleverly built their technology in a way that is decoupled from the underlying content management system (CMS). Around the time we invested, they began rolling out support for Webflow and Weebly, and will imminently support Wix, WordPress, JAMstack static sites, Carrd and basically any web platform out there1 . Customers of MemberSpace can easily switch between platforms, much to the envy of folks running complicated PHP plugins deeply integrated with their WordPress sites. Being able to switch platforms or even combine multiple platforms (ie a CMS, podcast host, private group, and download library) into one comprehensive membership business will be so powerful for their customers over the long-term.

Profitable, calm companies supporting each other

I don’t think the founders mind me sharing that MemberSpace is currently profitable on a team of nine full-time employees and intends to stay focused on building a profitable, sustainable company.

Why should customers care about this? Two reasons:

  1. Fair long-term pricing. We all know the story by now. A platform that creators and entrepreneurs rely on to run their business raises a giant pile of venture capital, tries to grow too fast, and eventually is forced to massively hike prices to their customers’ dismay or implode. MemberSpace is optimizing their company to never do that to their customers and we support it whole-heartedly.
  2. World class support. Profitable companies don’t optimize for growth, they optimize for retention. They want every customer that walks through the door to stay with them forever. I constantly see the founders intentionally holding back expansion to new platforms to make sure they can maintain the extremely high level of support that MemberSpace customers love.

Relentless focus on supporting their customers and community

The founders understand deeply that the key to their long-term success is a thriving community of makers building membership businesses. From their podcast highlighting awesome Member Makers, to their support of underrepresented founders at conferences, to their excellent guides to building a membership business… MemberSpace gets that community is the key.

  1. Note: technically through their “Custom HTML” integration they already work with all of these platforms if you don’t want to wait for the official integration.

Help Design the Earnest Opportunity Fund

These days it’s common for venture funds to raise an “opportunity fund,” a separate fund that sits alongside the main fund so they can invest more cash the performers in their portfolio. These funds are about opportunities for the fund. I want to talk about opportunities for founders.

We are designing the Earnest Opportunity Fund, an early-stage fund with the same investment thesis as Earnest Fund 1, but solely dedicated to backing underrepresented and underserved founders.

One year ago, we posted our draft ideas for how to design “funding for bootstrappers” and got tremendously helpful feedback from the entrepreneurial community on what became the Shared Earnings Agreement. We’re here today in the spirit of transparency with the same intention in mind. To put forward our best ideas on how to tackle a challenge and to solicit feedback so we can be better aligned with the founders we end up working with.


We often talk about ‘bootstrapping’ but very few founders actually build a business with literally no outside capital, savings, or help. In our personal experience, from asking lots of founders in private, a large portion used their own accumulated savings from a high paying job, had a spouse that covered the bills, had a windfall or inheritance, or relied on loans and help from family members. Every one of these is systematically harder in some way for founders of color, female founders, LGBTQ founders, and founders from underprivileged geographies. Note, none of these are insurmountable and we all know folks in every one of those categories who has successfully bootstrapped a business, but bootstrapping as we know it is systematically tilted against underrepresented founders in a way that we believe justifies a countervailing strategy.

The world of capital allocation is not much better. Statistics abound, like these from the Kauffman Foundation, showing that all-female founding teams and founders of color are able to access dramatically less investment capital from across the spectrum of venture capital to bank loans to credit cards.

Our experience with Earnest has led us to believe that we are still ‘downstream of privilege’ in a lot of important ways. We expect founders to find a way to build and launch a product, get some amount of revenue traction, and have a roadmap to build the company profitably without relying on too much additional outside capital. Perhaps unsurprisingly, as I’ve tweeted before, the vast majority of the inbound applications have come from all-white-male founding teams. We don’t officially collect this data at this point but anecdotally I would say it’s 85-90% of the 1,000+ opportunities I’ve seen this year. To date, Earnest Capital has not had a mandate to invest in diverse founders. We have tried to pick the companies that most closely matches our funding for bootstrappers thesis and those that showed the most traction and trajectory. So our portfolio looks a lot like our inbound: full of amazing founders, but predominantly all-white-male founding teams.1

We had roughly the same experience with the process of buiding our mentor group, largely as a result of our “skin in the game” rule that requires mentors also be invested in the fund, and thus in the founders they are mentoring. We’ve gone over that in more detail in a previous post.

It’s become cliche to say that “talent is evenly distributed but opportunity is not” but it’s correct. The point here is we have an opportunity to do better.


So here’s what we’re proposing, drafting, and looking for feedback on.

Earnest could launch a second fund with the same thesis and stage of investment as the main fund: still early stage, $50-250k checks, business models with a focus on capital efficiency, profitability, and sustainability.

We’ll be investing concurrently out of both funds, in some cases from both into the same company. We may not even make it obvious which fund is investing—though it would probably be impossible to completely obscure that even if we wanted to—or may leave it up to the founder to decide if they want that information public.

Founders would have undifferentiated access to mentors and the community. This would not be a separate cohort or have a separate mentor group (though we would also love for this process to expand the diversity of our mentor group as well).

One big open question is what is an appropriate, fair, technical, and legal way to define who exactly is an underrepresented founder. If anybody has some well-tested best practices to share, perhaps from another industry, I would love to hear them.

So why bother having a separate fund?

One question we’ve been asked, and asked ourselves, is: why not just make a concerted effort to invest in more underrepresented founders out of the main fund? It’s a fair enough question. Here’s our current thinking on it:

1/ We raised money for Earnest Capital to prove a very specific, altogether different set of assumptions around investing in early-stage companies, that were not on the VC track, while still generating an appropriate risk-adjusted return. Earnest as it exists today does not also have a mandate to invest in underrepresented founders, so to date, we just haven’t taken it into account in our investing process.

2/ Whether in investing, recruiting, or conference organizing, everyone who does this well seems to agree, it takes work to build a network and a pipeline of underrepresented people. It doesn’t just happen. We are practically bootstrapping Earnest ourselves and operate with an extremely lean team. It probably makes sense for well-funded established funds to try to make efforts to move the needle across their entire operations, but for us it has felt like balancing too many different priorities with too little bandwidth.

3/ Based on tons of discussions on this, our current position is that to make a difference here you need to really plant a flag. As we launched Earnest, and we noticed the lack of diversity in folks applying and would occasionally reach out to underrepresented founders with interesting side hustles and ask why they hadn’t applied.

One of the things we heard most commonly was “Oh, I just thought this isn’t for me.” Well… this is for you. So let’s get to work!

Is this a publicity stunt?

No. But it’s a fair question and one we want to be held accountable to. To be clear, the Opportunity Fund is not live (yet) and may never get there. Launching funds is extremely challenging and the more constraints you begin to stack up—funding for bootstrappers, Shared Earnings Agreement, underrepresented founders only—the less likely it can be to get it off the ground. We’ll see what happens.

Who will run it?

The current plan is to have one or a small group of folks in a role modeled on “venture partners.” Here is a good explainer on how these roles typically work. The gist is they are part-time roles focused on sourcing and vetting opportunities, working with and mentoring founders post-investment. The compensation is primarily (though not exclusively) in the form of carry on the profits of the investments we make out of the Opportunity Fund.

Some have suggested that if we’re going to do this, we should add a dedicated general partner for this. We agree it is the right goal, but finding a new general partner is not something to rush into and not something that should hold up this process. Ideally the Opportunity fund is a huge success and one of the venture partners becomes a full general partner in the future.

Are we, at Earnest, even the right people to run this? Honestly maybe not. We’re still going to try this but if somebody else wants to take the idea and run with it, we’ll help.

We’ve already had a number of conversations here but it’s very important to break out of our filter bubble for this process. So, who should we be talking to?

Time for feedback

We’ve turned on comments for this post and would love to hear any and all feedback. You can leave a comment below, tweet at us, discuss on Indie Hackers here or Hackers News here, or email me directly.

  1. Although interestingly Earnest is far more geographically diverse than any venture fund portfolio we’ve ever seen.

Our new head of platform and newest portfolio company

We have some bittersweet news at Earnest. The inimitable Ben Tossell is going full-time on Makerpad and stepping down from his role running platform at Earnest. Fortunately he’s not leaving us as I’m thrilled to announce Ben and Makerpad will be joining as the latest Earnest portfolio investment 🙌

When Ben came on board last year, Makerpad was still an experiment spun out of his previous startup newCo. Over that time he’s done an amazing job balancing growing Makerpad with making himself available for weekly founder 1:1s and creating a vibrant community of mentors and founders and generally rolling up his sleeves to help our founders in all kinds of useful ways. But as the no-code movement kept building up steam, Ben kept cranking out the best tutorials, content and community for it anywhere. With new no-code platforms and tools launching every day, Makerpad just kept growing like a rocketship.

In his great interview on the Indie Hacker podcast, Courtland asked him frankly “why is this still a side project for you?” It was a good question (thanks Courtland!). Ben and I had frank conversations about this all along and it became clear that the opportunity was too big to not have his full-time attention (plus a team… did I mention he’s hiring?) focused on it.

So this means two things:

1/ We are hiring a new head of platform. Is that you? We are going to run a public process for the role this time so please apply here or forward this to the person you know most likely to love working with our founders and mentors, and building our community and tools.

2/ If you haven’t checked out Makerpad yet you should, it’s the best resource on the web for building tools without code.

For Investors: What is a Shared Earnings Agreement and How does it compare to a SAFE?

This post will answer some common questions from investors looking to use a SEAL themselves or considering co-investing with us. If you are a founder looking to raise capital you will probably find the main Shared Earnings Agreement page more helpful.

Relevant excerpts from our public term sheet are pasted inline but the full document is viewable here.

Earnest Internships

Earnest is growing and we need your help. We are opening 1-2 internship positions starting in September. These positions are remote, part-time/flexible, and paid.

You’ll be helping out with

  • Organizing and joining weekly check-ins and meetings with our growing portfolio of founders.
  • Helping founders solve problems, connect them to our mentor network.
  • Researching new markets and investment opportunities.
  • Sharing what we learn in our community by creating more content to help other founders.
  • Connecting the (mostly no-code) tools we use to run Earnest.
  • Planning some upcoming IRL events.

You don’t need to be an expert in all this, just willing to work hard, be creative, and stay open-minded. Honestly we’re making a lot of this up as we go.

Some things you should know about Earnest

  • We are a fully remote team. Get ready to spend a lot of time in Basecamp, Slack, and Zoom.
  • We love experimenting, trying new things, doubling down on what works and ditching what’s not. Be ready for some fun and also some flux.
  • We’re generally fan of calm, deep work. There’s plenty of emoji and fun weekly calls, but if you need constant face time to stay energized, this might not be the best fit.

Follow-on opportunities. Earnest is growing and we do have a few open positions coming up, but we are still a very small team and this internship is not necessarily an on-ramp to a full-time position at Earnest. Many of our portfolio companies are actively hiring, but if you absolutely need this to convert into a full-time role, candidly there may not be one. That said, we will do our absolute best to ensure working with Earnest is a launchpad for you.

Practical Items

  • Being +/- 5 hours from US Eastern Time will be a big help unless you’re a serious night owl.
  • We envision this to be a part-time flexible role (10-20 hours/week) that can be done alongside other work but if you’d prefer full-time let us know.
  • For your application please send anything but a resume, CV, or LinkedIn request. Send links to things you’ve made or written, a video, your best Tiktok, or just a simple well-written email.
  • Send an email with the subject line “Earnest Internship: {your name}” to

Wholesale Gorilla: the best wholesale app for Shopify

Earnest Capital is proud to back Wholesale Gorilla, which allows any Shopify store to seamlessly serve wholesale customers.

Matt and Hallie, from Louisville, Kentucky, founded Wholesale Gorilla in a classic scratch your own itch story. Hallie launched Graymarket Design, a scarf and textile vendor on Shopify. When wholesale buyers started inquiring they found Shopify was not able to support the key features wholesale customers need like bulk pricing, minimum orders, freight shipping, NET30 payments, and so on. Rather than bolt on a separate wholesale portal, they built out a custom app to allow logged in wholesale customers to use their existing store. After using the app to run their own business for two years, they made it available to other merchants. With zero marketing they have accumulated a huge waiting list of customers that they have been diligently working their way through.

At Earnest Capital our core thesis is around enabling distributed entrepreneurship and any time we can back a company and double-down on that we love it. Wholesale Gorilla enables a literally seamless—the product actually transforms the full shop UI for logged in wholesale customers—transition from DTC e-commerce startup to growth via local retailers and wholesale distribution. We are excited about the Wholesale Gorilla team because as avid customers of their own product, the team is always going to stay a step ahead for their merchants than the inevitable dev shops or copycats.

Shopify merchants should check them out directly on the app store. Merchants not on Shopify but looking for a powerful wholesale engine should say hello directly to stay in the loop for future announcements.

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.