Episode 277 | Five Ways to Structure Your Startup Mastermind

Startups For the Rest of Us

Episode 277 | Five Ways to Structure Your Startup Mastermind

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Show Notes

In this episode of Startups For The Rest Of Us, Rob and Mike talk about five ways to structure your mastermind. They list some different formats to try and the pros and cons to each.

Items mentioned in this episode:

• ZenFounder
• Sherry Walling’s Retreat Book
• The Nights & Weekend Podcast
• Mastermind Jam
• The Productivity Project Book

Transcript

Mike [00:00:24]: In this episode of Startups For the Rest of Us, Rob and I are going to be talking about five ways to structure your startup mastermind. This is Startups For the Rest of Us, episode 277. Welcome to Startups For the Rest of Us, the podcast helps developers, designers, and entrepreneurs be awesome at launching software products, whether you’ve built your first product or you’re just thinking about it. I’m Mike.

Rob [00:00:25]: Hi, I’m Rob.

Mike [00:00:29]: And we’re here to share our experiences to help you avoid the same mistakes we’ve made. What are you doing this week, Rob?

Rob [00:02:16]: Well you know how at the end of every year I talk about how email had become such a problem for me. That’s kind of the one thing I’ve haven’t been able to fix. I feel like I’ve outsourced or delegated or figured out systems for so many things, but my inbox was always the one, it’s just hammering me non-stop. I finally might have a solution. Basically I hired a VA about, let’s see, six or seven months ago. And it was more like, I’d say maybe a step up from just a standard VA, and it was someone who called themselves an Executive Assistant so I’ll call her an EA. And Executive Assistants are more used to dealing with executives, in essence, and it’s not like I’m some high-powered executive, but they are used to managing calendars and going through email and evaluating things, and being less about – there is definitely some process there but it’s also a lot of pretty hardcore thought put into it. And so the one that I had before didn’t work out. It became a little too much of a process and she was basically just filtering my stuff into some categories and it wasn’t actually helpful. I let her go a while back, she eventually became not liable. And now I have a new one who’s been with me for about a month and I’m slowly ramping more and more up. I have notices a dramatic difference now. Instead of waking up to 70 or 80 new emails in my inbox every morning, and then I get another 50 during the day or something, it’s just way, way less, stuff that I’m processing. Because not only is she filtering things, but she is responding to podcast invites. I told her my criteria, my loose criteria for evaluating invites for interviews and guest posts, and even some partnership stuff and she’s starting to take some action on those and inquire for more information or to let someone know that not able to do it or to actually book the thing, and then she has access to my calendar and she’s booking that. A long way of saying this week I’m feeling finally good for a brief glimpse about the status of my email inbox.

Mike [00:02:21]: Cool. I just have one question about that. Are my emails getting directly routed past?

Rob [00:02:59]: They definitely are. I said one of my things is if someone seems like they know me and they’re emailing me, just put them into the ‘Today’. ‘Today’ is everything I handled today. I get a lot of cold pitches for different things and I’ve asked her that if they’re cold that either evaluate it yourself or if you don’t know how, let’s talk about how you can evaluate it in the future, and then she puts it into a ‘This Week’ label. And I check the ‘This Week’ label once, maybe twice a week. And that’s where I have some newsletters that I like to read and some other stuff. And it’s people asking for advice as well, if I don’t already know them. Stuff that I just want to do in a big batch. Yes, since you know me, you would go into the ‘Today’ label.

Mike [00:03:01]: Well that’s good to know, I guess.

Rob [00:03:22]: The other thing, too, is I’m not having her reply as me at all. For some reason that feels weird. I know some people have a VA or an EA reply as them and that, I don’t know that I will ever want to do that. I’d prefer for her to basically send it over to me and I reply or she can reply but signed as her just to let someone know.

Mike [00:03:28]: I was going to say you could just have her do that and do the reply but then also sign it as herself instead.

Rob [00:03:28]: Exactly.

Mike [00:03:29]: That would work.

Rob [00:03:31]: How about you? What’s new this week?

Mike [00:04:33]: I was reading a new book over the past day or two. It’s called the “Zen Founder Guide to Founder Retreats.” And that’s by Sherry Walling. We’ll link that up in the show notes. I talked about founder retreats in my book as well, but it was based on an interview that I did with her and also, obviously, she was the source of that idea. So this is probably the definitive guide, I would say. It walks through four steps to making sure that you have a successful retreat and then goes through various strategies and activities that you should use while you’re on that retreat. And then it also includes some worksheets along with it. Like I said, we’ll link that up in the show notes, but I would definitely recommend that anybody who’s out there who’s considering a retreat or even if you’ve already gone on a retreat, there’s a lot of good tips in there. I especially liked the strategy section where she maps out four different strategies specifically for how to answer some of the questions that you have in your head, or how to go about goal setting. Again, definitely worth a read. We’ll link it up in the show notes.

Rob [00:06:27]: I was pretty happy with how this turned out. I did absolutely none of the writing. I didn’t write a single word in this thing. I did read it over for her and give her a little bit of advice, but she really drove it. And this is the first product she’s ever launched so I’m excited about it and she’s certainly stoked about it. If you go to ZenFounder.com there’s a link to it in the right navigation and I think she’s selling it for $24.00 via Gumroad. If you’re interested in it you should check it out. I have another recommendation for a book. It’s something I stumbled upon from listening to the Unmistakable Creative podcast. And the book is called “The Productivity Project.” I’ve listened to a lot of productivity books over the years and I’ve become immune to a lot of them and they have a lot of suggestions and tactics that don’t necessarily work for everyone or they just become advice that you don’t take. But what this guy did is he did, I think, a 100 different productivity experiments over the course of a year or a little more, and he basically looked at all the best advice and some of the worst advice and just implemented it and then he recorded all the results and he published it on a blog. And later, that turned into this book. So the book itself, I think, is 20 or 25 of the ones that worked the best for him. Maybe I’m 20% into the book and I had to stop listening in the car because I wanted to take so many notes and I didn’t want to take notes while I was driving. It has really resonated with me in terms of actually having actionable stuff and things that I have implemented so far this week. I mean I’m only three days into implementing these, but I want to see if I can make them sustainable because I think his suggestions and his insights are worth doing. Again, I’m not a huge fan of these productivity books because once you read one, if you’re not implementing the suggestions, then you should not read another until you do. But if you think you’re at a point where you really need a boost in productivity and you’re ready to start building some new habits, and I think that’s the key, then I would check out “Productivity Project.” It’s obviously on Amazon and Audible. I’m listening to it on Audible myself.

Mike [00:06:40]: I was just going to mention that when you pick up those types of books, basically if you make the decision to go down that road, you’re creating work for yourself because you have to commit to doing those things otherwise reading the books doesn’t actually do anything for you.

Rob [00:07:13]: Exactly. And I think I’ve listened to three or four approaches and I’ve noted down one, one and a half. I made a variation on the second one. And that’s what I’m going to do, is filter each one and say, “Am I going to do that? Do I think it will work, and B, do I have the discipline and the head space right now to start doing that?” And my hope is not to come away with 20 new ideas, it’s to come away with about three or four, and then implement one, make it a habit, wait about a month and then implement the second, make it a habit, wait about a month. So that’s my plan with it. But hopefully it helps folks out if you decide to listen to it. What else is going on?

Mike [00:07:49]: We have a question that came into us from Don Falcor [ph] and he asks us about using Medium. And he said, “Hi Rob and Mike. I’ve recently noticed a slew of folks who are using Medium as their content marketing platform instead of their actual site. I noticed that Drip is also doing this. My thought process is that I’m now losing control of the platform and I’m not able to provide a Drip pop-up or email marketing opt-in form and cross promotion since I don’t own the platform. Medium’s rather limited, and though it’s a fantastic tool for writing and sharing content, I can’t get past the fact that I no longer own the platform and I essentially lose the extra opportunity to cross promote and upsell a reader. The question is why do you use Medium instead of your actual marketing site?”

Rob [00:10:29]: And the answer for us is that we started it purely as an experiment. I’ve got quite a bit of content, let’s say between two and four posts a week and some of those – we put a post out today on blog.getdrip.com. It’s essentially a 3,000 word teardown with a bunch of screenshots of Derek Halpern’s recent email sequence that he used to sell his seven figure course thing. So we’re putting out pretty big pieces of content like that, and what we found is if we didn’t experiment and we ran it on our blog where we send the tweets to send people to the blog, and when we email our list we send people to the blog, and we did all that and we looked at the numbers. Then we tried a separate experiment where we still posted to the blog but then we posted to Medium as well. At the bottom of Medium we have two things. One, we have a link back to our blog that says “This was originally published here,” and we then have a call to action, “You can get this free email marketing email course.” They have to click through and there’s a landing page and they have to enter their email, so it isn’t as nice as being able to embed an opt-in form there. But the whole Medium post is there and so far we’ve seen no Google content penalties or anything like that, having duplicate content. In addition, then when we do the tweets and we do the shares and we send the email we refer people to the Medium post. It still exists on our blog, people can find it. But we’re sending them over there and the idea there is that you’re basically using your network to get noticed within the Medium space. The more hearts and more reads something gets, the more likely it is to get onto Medium’s list of popular posts today. And if you hit one of those then your stuff skyrockets. You get 2X, 3X the traffic and the views and the reads and all that. So that’s the idea, is you’re trying to utilize some else’s network. I totally agree with Don in the sense that you’re losing control if you’re building it solely on Medium. We’ve gone back and forth and we’ve run different experiments and what we found is that we do definitely get more traffic and more reads over on Medium. We also have found that they tend to be, I’ll say less qualified. So we get less interest, less people clicking back to our site because they’re not on our blog anymore, right. So there isn’t a Drip logo on the header, we can’t directly ask for the opt-in. There’s pluses and minuses here. I don’t have a definitive answer. We have not made a decision to go solely with Medium. I wouldn’t make that decision because I still want stuff to live on our blog. We don’t want to be a digital sharecropper where you’re basically building this community and this reputation but you don’t own any of it like Don said. I guess that’s a non-definitive answer to what we’ve done and the experiments we’re still currently running. And we were just evaluating one today. I was evaluating with our growth marketer Zack about which way should we go? Do we need to make a commitment to these because some we’re posting on Medium and then some we’re not. I didn’t realize, that was a long answer. It’s probably the shortest answer I could give.

Mike [00:11:25]: So Don hope that helps. Thanks for the question. In today’s episode what we’re going to do is we’re going to talk about five ways to structure your startup mastermind. And back in episode 167 we talked about how to organize and how to run a startup mastermind. So if you’re not a member of a mastermind group or you’re thinking about starting one but you’re not quite sure, go listen to that episode and you can learn some of the basics of how to get started. But in this episode what we’re going to do is we’re going to talk about the pros and cons of some different formats that you may or may not have tried in your own mastermind groups. This came about because in my own mastermind group, what we’ve started doing is we’ve started experimenting a little bit and talking about what different things we can do and how we can continue to use the people that are in the mastermind group to drive our businesses forward, but also to do some experiments, to not just mix things up so that the format itself isn’t stale but to help identify whether or not there are other formats that would work better for our businesses.

Rob [00:11:31]: So today we’re going to be talking through five different approaches for structuring your startup mastermind.

Mike [00:12:28]: The first approach is to use what’s called the round table. In the round table, pretty much everyone speaks for an equal amount of time for each session. Let’s say that you have a mastermind group with three people and you’re meeting for an hour and a half, then each person gets about half and hour. There’s a couple of different reasons why you might go with this approach. We started using this approach very early on just because it was the one we came across first and it just made sense. But one of the benefits of doing this approach is that pretty much everybody gets to speak every single time so everyone has a reason to go there. Everyone has a reason to show up because they are going to be getting valuable feedback for their particular business. And another reason is that you always get an opportunity every single time you meet to bring up the problems and issues that you’re facing in your business that were a little bit different where, let’s say you were skipped on a particular week or you got less time then you wouldn’t have those opportunities to talk about the problems that you’re facing.

Rob [00:13:46]: And to be honest, this is my preferred approach. I wouldn’t say it’s the best one but it’s the one that I’ve found that resonates the most with me because since we only meet every other week in the two masterminds we do, I’ve always struggled with if we do a hot seat one or a rotating hot seat, that I may not get to talk about my stuff for four, six, eight weeks, and that’s just too long given how much is going on. I think it depends. It’s certainly a personal preference and maybe it depends on what stage your business is at and how fast things are moving and how often you meet. But I’ve always really like the round table approach. I’m trying to think if I’ve even ever tried any of these other ones. I don’t know that I have. I think we might have done a hot seat one at one point and I didn’t like it as much as round table. But I do know that some people swear by the hot seat approach. And one of the cons, or the con, I think, the biggest con of the round table approach is that you may not get enough time, you may not be able to dive in deep enough into specific topics most of the time if you have four or five people in a mastermind and you only have an hour to meet, then you have like 12 minutes. So you really need to focus on what you’re talking about. I think the way I’ve gotten around this if by keeping masterminds really small, like three people, and then meeting for 60 or 90 minutes so that you have apple time each time. There are some trade offs here, but that, compared to the others, that would definitely be the drawback of round table approach.

Mike [00:15:17]: The second approach that I came across doing some research was essentially doing a timed segment. In a timed segment, what you do is you divide the call into very short time segments for somewhere between five and ten minutes. Let’s say that you have five minutes allotted to you, you can talk for those five minutes and then you get one minute to ask and answer questions, and then you get about a minute to transition to the next person. Now, in this, the nice thing is that you get to speak multiple times. So if you’re meeting for an hour and there’s three people, you’re going to get four different opportunities to speak or somewhere along those lines. Obviously those extra one minutes in there, but you get to talk several times in a row throughout the course of the conversation. And one of the other side effects of this is that if you forget to bring something up, you can bring it up later. What I’ve found in doing the round table is that if I go first, for example, then I might speak for my half and hour and then a little ways into somebody else’s turn speaking I might remember something. It does give you the opportunity to come back and bring something up that you might have forgotten about. The other thing that it does is it helps to keep the call on track without meandering a lot. I have had calls where the mastermind group will go long or will meander into discussions which are sort of meaningless, but if you have a strict timetable that you’re trying to stick to, then this can help alleviate those. And it’s not to say that you shouldn’t have fun during your mastermind calls, but there are certainly times where conversation will meander a little bit and an hour and a half call can turn into two and a half hours pretty easily.

Rob [00:16:19]: What I also like about this format is in essence it keeps you from having to listen to the same voice for 20 or 30 minutes. Studies have shown that if someone sits there and talks for no visuals for a solid 20 or 30 minutes that people, you almost naturally tune out. Our attention spans are only so long when it’s just one person talking. And so this breaks it up more and gets multiple voices into the system. I think this is a cool approach. I hadn’t heard of this one before. Obviously there are a couple cons to this one. I think the first one is that you need to be really focused to talk about your topic in only five minutes. Five minutes goes very quickly, and so if that’s all the time you have then you need to present an update and then maybe ask a question, and then you just have time for one or two people to weigh in and you have to move past it. And maybe the other con is that someone needs to be keeping track of time because if someone doesn’t have a timer going that beeps, you’re going to go long every time because five minutes is so short. You would have to be more structured and be willing to cut people off with this approach, but there’s the only two cons I can think of.

Mike [00:16:32]: It seems like you have to be much more, not just structured, but it’s very much more business like. It becomes less of a, I don’t want to say less of a peer scenario or friend scenario, but you’re a lot more businesslike about what you’re doing, what you’re talking about because you have to stick to that timer.

Rob [00:16:34]: Yeah, a lot of discipline to get this one going.

Mike [00:17:29]: The third way to structure your mastermind group is to have a short hot seat. This is similar to the round table in that every person still gets a chance to talk during that session, but one person is going to get extra time on the hot seat that week. And everyone else who is not on the hot seat is going to provide smaller updates. Let’s say that you’ve got three people in a mastermind group that’s a 90 minute call, one person might get an hour and the other two each get 15 minutes, so that would carry you through that 90 minutes. One of the benefits to this approach is that you get to have longer between your sessions in order to focus on your goals, and then during your hot seat you would provide larger updates when you are on the hot seat. If you have three people in your group and you’re meeting every other week, then it’s going to be six weeks to focus on your goals and buckle down, and then come back to the group and be on the hot seat about what you were able to accomplish over those past six weeks.

Rob [00:18:08]: There’s a couple pretty solid pros with this one. First is that you get longer between sessions to focus on your goals, and so you’re able to provide larger updates when you are on the hot seat. Because, as you said, you have a gap of like six weeks or eight weeks between times you talk so you can get a lot done during that time. The other pro is that you get to do one or two deep dives during your turn and get more detailed feedback. Because if you’re really on the hot seat for let’s say, 45 minutes or something, you can cover two topics, even three, pretty in depth. And you can explain a scenario, ask for feedback, get a good discussion, and then move on. There’s just a lot more time here to dive into some things that you might need help with.

Mike [00:19:08]: There’s also a number of downsides to this approach. The first one is that there are obviously higher expectations for you when you’re on your hot seat. For example, if you didn’t perform and it’s been six weeks since your last hot seat session, it’s really hard for the other people in your group to let that slide because you’ve had a number of weeks in order to work on that stuff and to get things done. The second thing is that it takes a lot more preparation for when you are on the hot seat. You really have to spend some time in advance of the call and make sure that you’ve got all your numbers laid out and you come to the group with some very explicit questions along with the data that you can present to them that will, essentially, give them some context about why you’re confused or why you’re not sure what to do at that point. So those two things definitely factor into the cons list. And this is an approach that we’ve tried in our own mastermind group. We’ve tried the round table first and then we went over to a short hot seat. And these are some of the things that I’ve brought out of that as cons for this particular approach.

Rob [00:19:40]: I think another couple cons to this approach are, one, that it can be easier to let things slide a bit during the weeks that you’re not on the hot seat. If you’re really going after strong accountability, then having six or eight weeks between each time you talk might not be optimal for you if that really is what you’re looking for. And the other con I can think of is that you might not get the ongoing attention you need if you run into a serious problem right after you have a hot seat because of the delay between them. Obviously you could always have email exchanges and get around that through other means, but that is definitely one of the cons.

Mike [00:20:42]: The fourth structure that we have here is a dedicated hot seat, and this is different from a short hot seat where a short hot seat, you still get an opportunity to speak every week. With a dedicated hot seat, each session is focused on a single person and that’s the person who’s the focus of the entire session. Obviously the benefit here is that you get an entire session that’s dedicated specifically to focusing on your startup and the problems that you’re having and being able to really dive deep into a lot of the issues that you’re facing. But that also comes with the drawbacks. And the drawbacks are that it could be several weeks before you give any kind of update to the group, and a lot can happen during those six or eight weeks. If you’re going to do an approach like this then it would seem to me like you’d probably want to also have another mastermind group that you’re part of that is not doing a dedicated hot seat approach. That’s where I think this would probably best fit in. I don’t think that it’s something that you can do alone. But if you do this in conjunction with some of the other mastermind formats then it would probably work out quite well.

Rob [00:21:15]: This is taking the rotating or the short hot seat approach to an extreme, I think. Obviously you get a lot of good time dedicated to your own startup and your problem when you’re on the hot seat. I think the cons here are again, there’s going to be several weeks between giving any kind of update. So that could be, I think, a real detriment to you. Also, it’s easier for someone to justify skipping a session because they’re just contributing ideas and really not getting much out of it. I think you’d have to have a certain kind of group and attendees if you’re going to do this, because if people start skipping sessions then it really isn’t going to work. It isn’t going to be an optimal mastermind at that point.

Mike [00:22:57]: And the fifth way to structure your mastermind group is to use a moderator. And if you’re using a moderator then I think what you’re going to want to is you’re going to want to bring somebody in from outside the group in order to moderate the call and drive those discussions forward. There’s a number of different benefits to this approach because that moderator can be used to ask the hard questions and help push for results from people. Sometimes it’s very difficult to put pressure on your peers because you don’t want to come off as being overaggressive or overbearing or even taking hot shots at somebody who came back to you and said, “I think this thing that you’re working on here is a terrible idea.” You can essentially have those things piped through the moderator and the moderator can help do those things. They’re also there to help mediate any personal conflicts between people, which hopefully in a mastermind group you wouldn’t have, but those things do come up on occasion. The moderator can help with that stuff as well. The last thing that a moderator can really do is they will do a better job than you probably would of tracking people and holding them accountable to their goals. And what I found that is in the mastermind groups that I’m part of, I tend to focus on the things that I’m working on and keep track of those things very well, but when it comes to what other people are working on, unless they bring it up, it’s very easy for me to forget something that they commented on or that they said that they were going to do a couple of weeks ago or a month or two ago because I’m so focused on all the different things that I have to do. Unless you’re very regimented and disciplined about keeping track of lists or checklists where people can literally check-mark things off and say I did this and I did this and did this, unless you are doing that kind of thing, it’s very easy for somebody to just let something slip through the cracks and then not notice it for weeks or even months at a time if you notice it at all.

Rob [00:24:34]: I think this is an interesting approach and I think this is the old style of running mastermind. There would be an info-marketing guru in the ’90s or the early 2000’s and they would say we’re going to have a mastermind and they’d get eight or ten people together and then I think they would moderate it or they would get one of their minions to moderate it, and then they would charge for it. And they’d charge a lot for it, to be part be of it. And I think there are arguably some value there to be given advice by someone who’s ahead of you, as well as to be around other folks. I’ve always had an issue with A, the overcharging of this stuff and, B, the fact that there’s eight or ten people in the group really is beyond me. I can’t imagine that actually being that productive. Since I haven’t participated in one, I don’t want to speak too strongly about it. With that said, I think there’s maybe a more modern approach to this in having a moderator in a smaller group of, let’s say, between three and five people. And still compensating that moderator, because I think that if you really are going to moderate, which means you’re not going to be one of the participants, then you need some type of compensation. And that may be monetary and it may be something else. But it has to be worth you spending the time to do all of these things that you said, tracking the meetings and asking the hard questions and mediating personal conflicts and all that. I don’t think it’s a sustainable model. I don’t think someone’s going to do it for a year or two if they’re just doing it as a volunteer thing. But I definitely see the advantages of using this approach, especially if you really do want to be all about business. Like you said earlier, it’s less of a discussion and maybe a hang out time and conversations between friends, and it really is a hardcore moderated business discussion with someone keeping it on track.

Mike [00:25:05]: I think one of the downsides that I can think of for this particular approach is that if the moderator ever is unable to make the call then the call is probably going to get canceled at that point. Because if you’re so used to having that moderator around to drive the conversations, you may very well find yourself a little bit lost if they’re not able to make it for whatever reason. And then there’s the obvious things of being able to compensate that moderator for their time. And then the other problem of some people are just really not qualified to be moderators so you have to have the right type of person who is filling that role for your group.

Rob [00:25:50]: I think another con to it is scheduling becomes slightly more difficult because there is another person involved in the mix. Easy enough to work around, but it is something to think about. I think another con to it is I don’t know anyone who’s doing it today. And so there’s no model for it. It would be experimental and you would have to spend some time to find that moderator and the experiment with it and figure out if it’s going to work and you’re kind of pioneering it. So it’s less about listening to what others have done and more about pushing into some new territory, which is not a bad thing, but it’s going to take time. It’s going to take adjustment and it’s probably not going to be optimal at the start. To recap, we talked about five ways to structure your mastermind group. The first was a round table, second was timed segments, the third was a short hot seat, fourth was a dedicated hot seat, and the fifth was using a moderator.

Mike [00:26:18]: And we mentioned it earlier on that if you’re not a member of a mastermind group, check out episode 167 where we talked about some of the basics of finding a mastermind group and setting it up and finding people. Something else that you can do is you can head over to a Web site called MastermindJam.com. We’ll link that up in the show notes. It’s run by one of the MicroConf attendees named Ken Wallace who also cohosts the Nights and Weekends podcast, which you can find over at nightsandweekendspodcast.com.

Rob [00:26:35]: And we don’t get any type of commission or anything like that from using Ken’s service. We just know that he’s a smart guy, working on this problem and trying to solve it for the community. And if I was looking for a mastermind today I would either go to my network or I would go to MastermindJam. This is a place you’re going to want to do it in the bootstrapping circles.

Mike [00:27:02]: And what he does with that service is he actually puts you together with other people who are in similar situations and who, based on the data that he has available to him, are probably going to fit well because they are in similar market verticals or let’s say, if you were building a SaaS company he would put you with other SaaS founders with similar revenue numbers. And he does that work on the back end to make sure that the group that you end up with is a good fit for what it is that you’re trying to achieve.

Rob [00:27:23]: And with that, we’re wrapped up for the day. If you have a question for us call our voicemail number at 888-801-9690 or email us at questions@startupsfortherestofus.com. Our theme music is an excerpt from “We’re Outta Control” by MoOt, used under Creative Commons. Subscribe to us in iTunes by searching for startups and visit startupsfortherestofus.com for a full transcript of each episode. Thanks for listening, we’ll see you next time.