Hey @michaeljamescalkins it’s funny, you’ve reminded me that I really need to update that landing page. 
Thanks for the reminder!
In talking with my customers, it’s been overwhelmingly clear that many entrepreneurs agree with you. But it’s not that black and white in deciding which features to offer.
Specifically:
Scheduling: At first, I hoped I could code this problem away for my customers.
Last year, when I launched MastermindJam, I started working on an extensive scheduling tool with a simple UI. I built an API integration with a fantastic service that helps suggest ideal meeting times across time zones and disparate calendar tools, built that into an app that I’d link up to my onboarding and badda-bing, badda-boom you have a few ideal times to choose from.
But…
Before I put the final touches on the code, before I launched this fantastic tool, I decided to poll my customers. See if such a thing would even be useful.
When I asked people—paying customers— what kind of tools I could offer that would help them schedule meetings, the overwhelming response I get back from customers was “Look, I’m running a $10M/yr business: I can schedule a meeting. Especially if it’s for something as important as my mastermind group meeting. When it’s important, you MAKE the time.” Okay, fine, I get that. Personally, I kind of agree with that sentiment, really.
Yeah, yeah, I know what you’re thinking: why didn’t you ask this question before you started coding?! Great point. And a lesson I haven’t repeated since.
Since then, I’ve watched a lot of groups schedule their first meeting. I’ve observed that many of my groups (let’s say 30-40%) have a tremendous amount of trouble coming to consensus on the timing of their very first meeting.
So there’s clearly a disconnect between what the customer wants in this respect vs. what they need.
To combat this, the first email which introduces new group members to one another now shows a simple calendar to let people see at-a-glance how their availability preferences overlap.
If that simple availability overview doesn’t help enough, I suggest they use a tool like Doodle or GroupAgree or Vyte.in or WorldTimeBuddy to get in sync (there are a myriad of tools that solve this problem). Some groups have even used a Google Sheet spreadsheet to coordinate availability (which, to me, seems like too much tool for such a simple problem) but, hey, to each their own.
And, that’s really the extent of the simple scheduling tools.
I mention all of this to illustrate that a good number of people starting mastermind groups do experience scheduling hurdles.
Next, after each group is formed I send out brief, conversational training emails with suggestions on how to get started, how to coordinate the first meeting, how best to structure the agenda of the first meeting, how the agenda for the second and subsequent meeting should differ from the first, and so forth. And from there, I’m just available if any groups need assistance.
Reminders There are no reminders (yet). Back when I started, in my hubris of coding up a bunch of stuff before talking to customers, I built tech around making reminders a core part of the value of the system; including a Twilio based-SMS reminder system, and I built a slack-based chat bot. When I talk with customers about this, I get an overwhelming “meh” in response, so I never launched those tools either. More wasted time.
Slack Group There is a MastermindJam slack group, but I’ve never invited a single customer into it. Why? Because unless there is a certain member count to these slack groups, they become sad ghost towns with little engagement. I’m really on the fence about this one, because I think there is a lot of value in small group discussions. And, since during my onboarding I collect over thirty facets of data about each entrepreneur, with nearly 500 customers in the system today, I can segment them into really tightly targeted private channels within slack.
And there’s another advantage of slack, which is similar to the advantage that comes with a private login-protected discussion forum…
Privacy.
Forum A private, login-protected, non-Google indexable discussion forum is nothing like Reddit. Nothing like this forum here on discuss.Bootstrapped.fm. Because it’s private.
Entrepreneurs who are working on a side hustle hoping to leave their day gig don’t want to post something too revealing about their secret quest for freedom in a public, indexable forum like this.
If such a post is discovered by their boss, it becomes your letter of resignation.
No one wants to get escorted to the door of their day job for some offhanded remark they made in a progress/accountability thread on these public bootstrapped forums. But, it can happen.
Not so with a slack group, and not so with a private forum.
All that said: there already exist many really great private discussion forums and slack groups where you can talk business without being under the watchful eye of Sauron—er, Google*—and I’m not sure the world needs one more.
Video Courses I’ve had many customers ask for these, so I’m making them. Period.
Just very simple, short courses that are available if needed. There’s over 1,300 people who paid $49 for one of the leading mastermind group video courses on Udemy (and it’s one of dozens on that platform alone), so someone, somewhere is interested in buying a video course on getting the most out of their mastermind group (even if that someone is not you or anyone else on this forum).
All of these things are optional, really. Take what helps you, and use it to grow your business, leave aside all the rest.
My struggle from day one has been to offer the right cocktail of value to my customers in this space.
As in all products, there is no one-size-fits-all mastermind group program that will satisfy everyone, but I just honestly hope that the customers who trusted my product to get them into a mastermind group have found that trust well-placed, and have gotten real value out of their group.
* I, for one, welcome our new Google overlords.
