256: Behind-the-Business: 1:1 Voxer Coaching Summer Pop-Up—Structure, Systems, and Pricing (Listener Q&A from Renee)
8 Dec 2025 · 25 min
Jenny Blake breaks down her summer Voxer coaching pop-up: cohort-based, 12 weeks, $1,500/month paid in three installments. She uses Notion to track questions submitted Monday through Wednesday, replies by Friday in 15-minute voice messages. Early joiners get 30-minute calls, and community members get grandfathered pricing.
Questions this episode answers
11 spots (maximum for that summer).
Between Monday and Wednesday each week.
By end of day Friday (weekly).
Voxer caps replies at 15 minutes; Jenny typically replied 10–15 minutes.
Three months (12 weeks).
Chapters
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My philosophy with Voxer coaching is to be an open book and that's true for anything I do, but especially when somebody engages with me one on one. I give everything I have. I have no holds barred of sharing sample contracts or templates. I've used systems I do looms for people. I'm a giver and I really love when somebody shows up to work with me. I love giving super generously in return.
This is your time. How can we earn twice as much in half the time with joy and ease while serving the highest good? That is our guiding question here at the Freetime Cafe, your home for heart based business. I'm your host Jenny Blake. Join me for conversations with authors, friends and fellow business owners as we explore ways to free your mind, time, time and team to do your best work. Now onto today's show.
Happy New Year Free Timers. Today I'm super excited to bring you a listener submission. You know I love these. You can always submit A question@itsfreetime.com ask today is a question from Renee Rubin Ross who runs the Ross Collective on Inclusive Conversations. She's asking about my summer Voxer pop Up coaching. I've done it two summers in a row now and I've learned so much. Every subsequent time that I've done it. People also ask me, well why don't you just offer it year round? And there's a reason for that. But first I'll turn it over to Renee for her question. Over to you Renee.
Hey Jenny, this is Renee and and I'm just a fan of your podcast. I love what you share. You mentioned Voxer coaching and that that was something that you offered this past summer and I was curious if you could share more about how you set it up, how you let people know about it, what the parameters were, all of that, how much it cost. I have done some voxer coaching with someone in the past and was thinking about offering it potentially for my clients since people have reached out to me with different questions and I'm figuring out how to be responsive to them. So thank you and have a great one.
Thank you so much Renee. Thanks for listening to the podcast and for the kind words and for prompting an episode on one of my favorite business activities of the last few years. Let me start by saying if you're listening and you want to get on the waitlist for a future Voxer coaching cohort, you can visit itsfreetime.com Voxer that's also a good link to see how I word this program, what I would call the invitation letter page. So Again, that's@itsfreetime.com Voxer.
One of the big free time principles is to design experiences that you would want to have when the pandemic hit in 2020, a coach offered me three months of Voxer coaching. I left at the chance because I love keeping my calendar free. That's why I wrote a whole book about smarter systems to help all of us do that. And I was so excited about the opportunity to invest less than what typical coaching costs. And I would get to frame one question a week and she would answer with one voice memo, no follow up. And this is a coach who was really good at strict with her boundaries. I had so much fun that summer pondering what my big question would be. And of course sometimes I got stuck and I didn't know what to ask. But I loved listening back to her reply. I loved that it was asynchronous so neither of us had anything on the calendar. I loved that I could listen while on the go. We spent a lot of time outside of New York City that summer. I remember walking Ryder through the woods and listening to my coach's response and then reflecting on what she had said. I loved it so much that I decided to try it as my own Voxer coaching pop up a following summer. Maybe it was a year or two later. I really didn't know how it would go in terms of my own energy, in terms of interest from my community. But I knew that it was worth trying because I had a feeling that clients as well didn't necessarily want the investment of regular coaching or again having all the what my friend Sarah calls tiny boxes on the calendar. I also stopped taking one on one coaching clients in 2019. So it's not like I offer regular one on one coaching where we get on the phone and nowadays everyone's on zoom or video, which is even more exhausting. So I also knew that doing it as a pop up and not year round would allow me to work closely with people again in a really intimate way, but a little bit different than what I had previously done. People because to be honest, for the last few years, as I've focused on working on my business and not in the business, as Michael Gerber famously said in E Myth Revisited, I didn't quite have the same energy to hold for my one on one clients if we were working really intensely together for an hour at a time on the phone. And the last few years, just the kind of toll it's taken on my energy and holding space for so many people in so many different ways. Voxer coaching was another way that I could serve and do what I feel I do best, which is help people with systems and strategy and big picture thinking, but in a more compressed way. Still super powerful though. So the first summer of Voxer coaching, I had a handful of people sign up, maybe just four or five, and we all loved it. They got so much out of it. Many participants said, oh, I have so much from these last three months that it's going to take me a year to implement. And in fact, many of them, when I followed up the following year, offered them the first crack at the summer of 2023's spots. They said, I'm still implementing so much of what we talked about. My philosophy with Voxer coaching is to be an open book and that's true for anything I do, but especially when somebody engages with me one on one. I give everything I have. I have no holds barred of sharing sample contracts or templates. I've used systems. I do looms for people. I'm a giver and I really love when somebody shows up to work with me. I love giving super generously in return. Let's first talk about structure, then we'll talk about systems, then we'll talk about pricing. Although I'm always hesitant to release that here on the POD because it's always subject to change. And I do try to raise the investment over time. As far as structuring the program. In 2023, I expanded to include 11 spots. That was definitely a maximum. That kept me pretty busy. Two full days of the week. Participants would get to submit their question between Monday and Wednesday of the week once we kicked off, and then I would reply by end of day Friday. So that meant that two days of the week I was pretty busy. I was letting the questions roll in Monday through Wednesday and I would look at them early and start crock potting. But I spent almost all day on Thursdays and Fridays recording. If you think about it, it was like recording 11 solo podcast episodes every single week for 12 weeks. So there's no way that I could sustain that level of energy and attention year round. I don't even know that I'd have that many helpful things to offer if it would last a full year. But I knew that I could really add a lot of value and help people tremendously in three compressed months that again, they could work on throughout the year. Some people ask why Voxer and not Telegram or Marco Polo or anything else? I like how simple and streamlined Voxer is. I like that if you pay for Voxer Pro listeners or participants and recipients can transcribe the audio. It just does exactly what I need. No more, no less. I don't want the pressure of video. I don't want to be on video. I don't want the Voxer participants to feel that they need to be on video. I really like just how clean, simple and streamlined it is. It is so important to set the boundary that participants should submit the question between Monday through Wednesday because I didn't want to be scrambling last minute and I also needed to make it clear that their questions do not roll over from week to week. So it's use it or lose it. Now, that said, sometimes, and it happened a couple times, it was kind of common that at some point many of the participants got question block. They just didn't know what to ask. We had covered so much ground and when that would happen, I would often just tap into my intuition and leave them a 15 minute reply. Anyway, Voxer caps the reply at 15 minutes, which is another thing that I like. So it kind of kept things fair. I would reply 10 minutes if I was including a lot of extras, links, looms, etc. Or 15 minutes was kind of the max. I never did more than that. Another parameter that's really important to give to participants up front is they have got to bottom line the question for you. Because sometimes people are really excited and they want to give a lot of updates of the previous week and context and they're kind of feeling around for their question. But it sometimes could get confusing for me. They might ask a whole series of questions and then I knew I would only be able to give them a kind of watered down, wide ranging response. And it actually wasn't going to be the best use of their Q and A that week. So I would need to quickly reply and say, can you put your number one big question in big blinking lights for me? And what ended up transpiring in the second year that was really helpful is that sometimes people would leave a voice note. Again, their voice memo can be up to 15 minutes, but that they would actually type out the big question. That would be our form of blinking lights for me to answer. Now some people wouldn't give any updates and that was cool too. Some would just record a one minute voice memo. It was super crystal clear. It was there one question, boom. And so I think one thing to modulate as the coach is just figure out what your guidance is going to be around. How much content do you want the coachees to be sending you in advance? Would you accept three 15 minute voice memos? That's a lot to take in. That's a lot to listen to. Do you want to do pre work? Are you going to engage in any email in between? For voxer coaching, I find it most joyful that the boundaries be really clear just to keep it fair across the board and also so that I'm not doing too much other than answering the one question. Every now and then I would take a look at somebody's website or landing page of course, because that was part of what we were doing. But I think it's just something to keep an eye on again to keep it fair for participants and fair for you so that you're not going to too far out of scope in terms of going beyond the context of the voxer coaching itself. Now, a lot of these logistics I included in a kickoff email. So it was really important to me that everybody start at the same time and end at the same time. I didn't want to have rolling clients throughout the year because it takes a really intense form of attention and listening and holding space. Even though it's asynchronous, I'm still thinking about everybody's business, what they're working on. I'm sending resources when I can find them. I'm making connections to any other resources or people as I think of them. So for me again, ever since I stopped one on one coaching as an ongoing practice, it would just be too much for me to try to hold and juggle along with all my other regular work if it were happening in a rolling basis all throughout the year. What's nice about summer is that nobody wants to be in front of the computer in summer. So it's a good time to have clients pondering and submitting a question. And then I can be on the go or sitting outside or on the terrace playing with Ryder with the hose and answering in locations that are kind of joyful for me too. I just really feel increasingly stuck when I'm having video meetings at the computer. So voxer coaching is kind of the opposite of that when you launch in cohorts like this, you can send a very clear here's how this works. Email to kick off or now most likely for me, if I do this again in year three, I would have a notion page that they could refer back to because email sometimes gets lost. So every year I refine this page of what I want to say, how to make it clear, what pointers to give them. I also encourage participants to set a reminder on their phone so they don't forget because I although I say up front, it's use it or lose it, I don't want people to miss a week. It's monthly recurring three payments and it's okay to skip a week and sometimes that's a good thing and you just need the extra space. But I wouldn't want them to forget just because of a systems problem. For example, from a setup perspective, I also gave the group a chance to opt in to a triad if they wanted to be part of a small group that I wouldn't be actively listening or responding to, but I would connect them in voxer. You can create groups with three or five other people who are all working on similar things or at a similar level in their business. This was hit or miss. I've offered it both years. I would say one out of three or four potential cohorts really was off to the races in terms of corresponding with each other. But that group completely hit it off. They've had one on ones they were piloting ideas with each other, they were giving and receiving feedback on aspects that they were working on, like a sales email or a survey to their community to understand what to build or even walking through the types of services that they wanted to offer with each other, which was amazing and they may still be even in touch. That's a nice way to add value to the group and to each other without you being the bottleneck. So I'm really happy to offer that. Even though again, it can be kind of hit or miss who actually is most engaged with doing that? Because as with everything I do, everything's a low pressure sit. I don't want to add things to people's life unless it really is soul filling for them. So I don't want to just give them another to do to feel guilty about. So it's definitely optional, not required.
We'll be right back just after this.
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From a systems perspective. You know I have a very intricate notion page where I have all things related to Voxer coaching and this got way more sophisticated even in the second year. I keep every link, registration links, discount links for the BFF community, let's say all kinds of things. I even have a feedback survey at the end where I have a delightful surprise if they finish it. That's partly where I'll ask for testimonials to share with future potential clients. And I also save every single email that I send to the group check ins or during the enrollment process. So I have every email saved now. I also have a Voxer coaching tracker. Now this got super intricate. In the summer of 2023 I set up a zap so that anyone who enrolled was automatically added to a notion database. And in that database I tracked every single person. I had a checkbox did they submit their question that week? And then another checkbox did I answer the question that week? Then I even had an open text column for what was their question that week? And I had an open text column of how I answered it that week because 12 weeks times 11 people. I didn't want to repeat myself. How annoying would it be if you were one of the Voxer clients and I gave you some answer? Well, I had already said the same thing to you three weeks prior, but I jenny forgot because my systems weren't good enough. So I was very intricate with my tracking. If you look at this database, just data not sorted in any fancy way, it's so wide it just scrolls and scrolls and scrolls because that's four pieces of data that I was tracking for every single one of 12 weeks. I also could keep notes down below so if they sent me something to look at or I wanted to make more intricate notes about what they were working on that can go at the bottom of their notion card. And then I even kept for myself what are all the different resources that I recommended throughout the summer, what kinds of topics and challenges were coming up? What were the templates I was sending out most frequently? What were the podcast episodes and books that I was referencing? Those I then kind of pulled out of the tracker itself so that I had a quick way to say, oh, okay, now so and so is working on the best practices for setting up team systems. Okay, here's a little snippet that I can copy and paste for resources. I don't have to go find the same link to the same book or podcast episode or template. Again, that was really helpful. And I think that would only be increasingly helpful with each subsequent year because there are patterns of what people are working on or most interested in, or what their biggest challenges are. Finally, let's talk about pricing. So if you were a Voxer coaching client, I would just tell you exactly what I charge for different types of programs or parts of my community because this is on the podcast. I'll give you the broad strokes, but it changes over time. So just if you're listening to this, know that nothing is ever set in stone. The first year I offered this because I had no clue of what I was doing or if I would like it or if I would be any good at it. I charged 9.97 and I offered it to the BFF community at a discounted rate of 750. Now it's important to know that I always try, when I can, for any of my programs to let people know that if you sign up at this rate, you will be grandfathered in at that rate for life or grandparented in. That's my way of thanking the early people who are willing to help me test something and build the plane while flying it. So I don't mind that the following summer when the price doubled, the sticker price was 1500amonth that some people who were returning were going to pay 750. That feels totally joyful to me because again, they were there in the early days when I didn't really know what I was doing. And so I don't mind that they're coming back also because I have all the same context. We're not starting from scratch of working with each other. This last summer the sticker prize was $1,500 a month. But again, I always give discounts to people who are already paying for different programs in my community. So if you're a paying free time subscriber on Substack, if you're part of the BFF community, those parts of my business always get first crack at enrollment because it's a limited number of spots and a discounted rate, and that's really important to me. It's a way to say thank you for being in the inner circle. The payments are set up as three monthly recurring payments, and I'm not a super stickler if someone really needs to cancel for financial reasons or life reasons midway through, there's no refunds. But I'm not going to hold anybody hostage if they do two months of boxer coaching and they feel complete or again something happens and they just are not going to be able to proceed with the third month. No problem. In general, I try to not encourage that only because it's taking a spot for somebody who might have wanted one for the full duration, but I'm flexible in that way. Again, not trying to hold anybody hostage. I know that life happens when voxer coaching ends. I always like to give people options for continuing on with me in different ways. So there again, I'll try to offer a discount to say, okay, and now if you want to roll into this other program or thing that I'm doing, here's a coupon code for that. I would love to keep working with you or being in community with you in any of the following ways. In terms of duration. I asked the participants in the post survey if they felt that it should be longer or shorter, if they would prefer one month, two month, three even more. And just about everybody said that three months was ideal. It gave them enough time to get into a groove, but it wasn't so much time that they ran out of things to ask about. So we were able to make real substantial progress. And in fact, many participants said, this is the first time that I've actually gotten this thing off the ground or that I've worked with a coach and I made so much progress, which I wasn't expecting because we were never on the phone live. That was so fun for me to hear. I think there's just something about investing in yourself and having to ask a question every single week kind of keeps people accountable, keeps them moving forward, and it also helps participants break things down into small enough chunks. All the while, I'm again sending looms of anything that they can ask about. In my business, I'm happy to show or share anything that I can, as long as it's not confidential client information, and I do. So they're also kind of accelerating progress by just getting things that I've already created as much as I can give. At the end of the three months, I think everybody's Relieved. Okay, we feel complete, myself included as the coach. I just remember that Friday that I finished responding and I was joyful the whole way through. It's not like I ever got sick of it or wished I wasn't doing it, but when I sent that last message on that last Friday of this past summer, I collapsed onto the couch. I had recorded something like 126 one on one replies, all while producing 14 episodes a month for my two shows. So summer of 2023 was definitely busy. You could even hear my voice kind of scratching now partly because of a medication I'm on. But I would say longer than that is not necessarily better.
Last but not least, if you want to kind of get the enrollment kick started, you could offer for the first X number of people to join the Cohort would get one or maybe even two 30 minute one on one calls with you. This is something that I did and that I talk more about in the bonus episode on the free time substack for paying subscribers. Episode 100 on Ways to increase launch momentum. You might not be able to give away a one on one coaching session to everybody who enrolls, but it can be a great way to get enrollment started and get to know people even better. So when I did this in the past, when I've done this for any program, I'm actually quite happy that I get to do, let's say the voxer coaching for the 12 weeks, but also that we have one or two live touch points on the phone in that window of time because we create a lot of connection and a lot of warmth and it's definitely more bi directional than voxer coaching, which as somebody astutely pointed out, could maybe more so be called voxer mentoring or voxer consulting because it's not true coaching in the sense that you're asking powerful questions and mostly listening and facilitating thinking. It's kind of more of an exchange of information. So I would say if you're pure coaching and you're not such a fan of doing what I'm doing right now, like sharing, instructing, bouncing off of with your intuition, you know, bouncing off of things that they've said. If this is not your style, it won't scratch that pure coaching itch. But adding in one or two bonus sessions with you can be a real win all the way around. I hope that's helpful. Renee, thank you so much for asking this question because it really is something that I've continued to refine and learn so much about year over year. And we'll see. I never promised that I'm going to offer the next one, but if I do for summer of 2024 and you or anybody else who's listening wants the first crack at those spots, I doubt I would open up 11 again. But you never know. Visit itsfreetime.com Voxer and click the button to add your name and email to the wait list. Thanks again Renee for the great question. Thank you so much everybody for listening. Hope you have a beautiful rest of your day.
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