ST1 | Joe Rhew On Using A Sabbatical To Build Your Business

• When should you take a sabbatical?
• How to get opportunities and doors open for you
• Explore a way to build an actual income stream
• Package your portfolio and show tangible work

Transcript: Joe Rhew On Using A Sabbatical To Build Your Business

Well, meet Joe Rhew who’s trying things a little differently. Today he’s going to share how you could test your idea via a sabbatical or mini-break and how you can also overcome the dreaded resume gap in the process. But before I hand it over to Joe, may I request you to subscribe or follow ShopTok so you can continue to get such practical tips and advice from business owners around the world? Thanks a lot!

Hey Joe, thanks for joining us today. Before we get into it, would you like to spend a few minutes to introduce yourself?

Yeah, for sure. So I’m Joe. I am a career generalist. I used to be a little bit shy about sharing this back, but now I probably shared it with everyone. So I’ve worn a lot of different hats in my career, starting with the Korean military investment banking, and co-packing a couple of startups.

Eventually, what I found out was that I really liked being a generalist and startup operations, it seemed to suit that really well. So, you get to wear a lot of different hats, work with a lot of different people and learn a lot of new things in operations. So naturally settled into an operations role at Uber. Most recently I was a chief operating officer at a seed-stage company that was backed by YC. And I most recently left that this summer and now I’m on a mini-sabbatical.

Wow. Okay. So you’ve done quite a bunch of things recently and honestly, we’ll have to talk about your YC experience sometime. But maybe for today, tell us about your sabbatical and how you’re thinking about it.

Yeah, for sure. So, I’m no expert, but I’m on it right now. So maybe I can speak a little bit about it. The way I define this mini-sabbatical is that it’s usually a short sabbatical, maybe less than a year and you use that time to really pursue your personal interest and curiosity, and maybe start a project on a sort of full-time basis but knowing that it’s going to end at a certain point. So, before I can tell you a little bit more about mini sabbaticals and how we think about them, I do want to acknowledge that there’s a fair amount of financial privilege that comes with it. So, I was lucky enough to have worked quite a few years without any sort of family obligations and so forth. And so I have a few, I have a bank account with some savings, which then extends the runway for me to be able to go on this mini-sabbatical. So I do want to acknowledge that and make sure that not everyone was privileged enough to be able to do that.

Now, having said that I think there are a few characteristics that I’ve learned about that make a mini-sabbatical, a fulfilling and successful one. And so I think there are really three points. If I have to tell you, Hey, what makes a good mini sabbatical?

1. The first one would be that you actually have to have genuine passion or interest in what you’re pursuing during your mini-sabbatical.
2. The second is that you have to keep a very open mind during it and be very flexible and agile.
3. And then the third is that you have to have a good, realistic plan around it in case it doesn’t work out the way you thought it would.

Okay. So. I mean effectively, that sounds like the basic characteristics of a startup. Just that, I guess it’s time-bound which makes sense because, after all, you actually are trying a startup of some kind. So, what’s your passion then? What are you working on?

Yeah. Yeah, exactly. So, you know, maybe a sabbatical is something that you intentionally decide, Hey, I’m going to quit, leave my current full-time job, and actually go pursue this thing on a full-time basis. So you better be really excited and passionate and curious about it or else it’s just not going to work out. So if you’re, for example, burnt out, and your current job and you’re just looking for an exit, that might actually not be the right time to go into sort of doing this mini-sabbatical. For me, it was around no code, right? So as I shared earlier, I went from Uber, which had grown up to be a public company with a ton of engineers and so I had all the internal tools that I needed that were built and customized for Uber’s internal operations to use in my day-to-day work. And then I moved to a seed stage company and everything changed. So there were not enough resources, not enough engineers to work on internal tools. All the engineers were busy working on stuff that faced the customers because that’s the most important thing when you’re a fledgling startup.

And so as an operations person, I actually had to cobble together different no-code tools like Integromat, Airtable, Webflow, whatever it was to make the internal operations kind of flow. And as you know, working at a startup. I just don’t have the luxury of time to dive into these things and learn. You’re just trying to stay afloat and you’re, you’re doing whatever it takes to kind of keep your startup going and so. I realized during this time at the startup really, I would like to learn a little bit more about no-code because I felt like it could really give me a leg up in terms of doing another sort of early-stage, startup operations, which I’m very interested in. And so, the plan had sort of formed in my head and I said, okay if I leave the startup, I actually want to take some time off to just learn No-code, pursue my curiosity. Without necessarily a specific goal to parlay it into another job or anything like that. I just want to learn no-code because this is fascinating. It’s really interesting to me.

Right. And actually you, I guess that’s a good way to also segue into your next point, which is around open-mindedness and flexibility. I think you mentioned that it sparked. You were interested in the accord and you were trying to do something around that. So did this then actually spark into what you’re doing right now and it actually became the start of your journey?

So, my initial plan was, you know, let’s take this no-code boot camp put on by maker pad, loved that it was about five weeks. It was on a sort of part-time basis, afforded me the time and space to learn through code and as I was going through that Bootcamp, they were asking, Hey, you should really start a project, to practice your no-code skills. So, what I started out with was a newsletter to sort of share my learning or other operators, because I knew from my personal experience that the No-code skill would actually be really helpful in terms of operations.

I started the newsletter. I got a bunch of signups and then people started kind of calling me about their tips on no-code and stuff. And I was learning from them – from my subscribers, from my readers. So then I was like, Hey, I just started a community around this because these people clearly know more than I do.

And I want to learn from them. So it should be a bilateral type of communication, not just me sending emails one way. So I started a community and then after I started the community I had to find a way to get more people to join the community because a lot of the value of the community comes from more people joining and sharing their experiences and learnings. And so then I had to go to LinkedIn and start building a personal brand. And so that I could tell people what I’m doing, and this is why you should be excited to join this community that I’ve built, which then led to another opportunity, and another opportunity in terms of consulting. Then, I started looking into web three because web three is very much at the forefront of the movement around communities and creators. So really, you know, he started with a seedling of an idea of, Hey, I really want to learn about no code. But then it’s allowed me to take the next step and the next step. So it felt like I didn’t really know where I was going, but every step I took, I was able to see, you know, a couple of steps ahead of me and I think because I went in with the mindset of, I have no idea what’s going to happen out of this mini-sabbatical, I just want to learn no code, I was also willing to play ball with being really flexible and I was like, this is super interesting.

I want to learn about how to create a community. I want to learn now how to build a personal brand. Like web three, it is really leading the movement in terms of creators and communities, I’m gonna learn that. So, it’s really, going in with this sort of open-minded flexibility that has actually turned this mini-sabbatical into something that’s much greater than I had initially anticipated it to be, which was just learning around no-code.

Yeah. And actually, may I just say, I think that’s part of the attraction of your whole sabbatical approach because let’s say you were doing this as a side hustle. You would never have had the opportunity to be flexible because it would take you a few hours just to get your main thing done. And so you’d have to shut down opportunities versus exploring them. So, in fact, what all the stuff you’re seeing is actually making me feel even more like this is probably the best way to try and explore different kinds of ideas, anything that is not something that you know absolutely well, and you just are going to go in a straight line. Having the time has led you to explore all of this. So that’s great. I also want to pick up on one point, you mentioned somewhere in passing something pretty interesting, which is the consulting opportunities. I think you said something like, you know, people might’ve been reaching out to you about jobs and then you try to flip them into consulting opportunities, which is pretty cool. So, could you tell me a little bit more about that?

For sure. So. as I mentioned, I was building a personal brand on LinkedIn, really to fuel the growth for my community. So, I wanted to find operators at early-stage startups to join this community because we were missing a great group of people that we’re talking about, sort of the similar interest and shared and supported each other on their sort of entrepreneurial journey. And so my content on LinkedIn had to be around that and so I talked a lot about no-code. I talked a lot about operations. I talked a lot about, finding the right job opportunities and so forth on LinkedIn to appeal to the type of demographic that I wanted to be part of the community.

And as sort of a by-product of that, I started getting a lot of inbound messages from a bunch of different people who are like, oh yeah. I kind of have forgotten about Joe or maybe they didn’t know me. And they sent me a connection request and they’re like, Hey, by the way, I represent company A and we’re looking for someone to fill this role, X, would you be interested? It looks like your profile is very much aligned and what I would say to that was because I had set out to do this mini-sabbatical, I would usually say I’m not interested and that worked. And then they’re like, okay, cool. Let us know if you ever change your mind or if you can pass this opportunity along.

But there are some opportunities that are really interesting to me, but that I can not take on in a full-time capacity because I’m doing something else. So for those companies, I tell them, Hey, look what you’re proposing sounds super interesting, but I’m just not in the mind space or have the wherewithal to take this on a full-time basis because I had this community that I’m growing but the community doesn’t take my full time. So would you be interested in, you know, working out the arrangement where I can work on a part-time basis as a consultant to you? What I found through that experience, this approach never really works with large companies. So if you’re talking to Microsoft or any of the fan companies. They can easily go out and find other candidates somewhere else that are more than happy to join them on a full-time basis. For smaller startups which is actually what I’m more interested in. They are a lot more flexible. Like I said, they’re just trying to stay afloat and they need someone to come in and fix this problem. So, there are a lot more accommodating and willing to work with you. They’re more flexible, just like you are.

Going through this experience with smaller startups, I’ve also learned a few things about sales, which wasn’t something that I wanted to learn about when I first set out to do this mini-sabbatical, right?

1. So, one – I’ve kind of identified what’s my ideal company demographic or size that I need to talk to in order to land the consulting role.
2. Two I started thinking about, how I structure my initial call with them to get as much information from them to see whether it would be a good fit for both me and the company.
3. Three, I started thinking about who’s the right decision maker. Who can actually say yes – we can bring you on as a consultant instead of a full-time employee? Usually, it’s the CEO or the COO, some C-level executives.

And then. Lastly, I started really honing my pitch. In order for them to make it easy to say yes. Right? So, I would do a lot of research. I would think about, Hey, these are some problems that I experienced in my career, I think given where you are in your growth stage, you probably have similar problems in terms of your growth and so forth. Would you be interested in me looking at this? So, the short answer to that is, you’re going to have misses, you’re going to have hits, that’s part of sales. So that’s another thing that I learned but just taking that leap of faith and asking people, Hey, I’m not interested in a full-time job, but I can work on a part-time basis, I actually can open a lot of doors for really interesting opportunities as well.

Yes. Thanks a lot, Joe. I think this is a really valuable side point to what we were discussing, but, it was really worth dwelling on this because that is, again, I think it’s a function of the fact that you have time, you’re willing to explore, all of that. And it’s a way to build an actual income stream. I mean, that’s the whole side hustle, dream Entyvio which is you have a second or third income stream which means, you’ve de-risked your career to an extent. So, I mean, in this case, number one, maybe extend your runway. So, if you plan for six months, you now have a little bit more or it might even turn out to be a career. So, you know, if enough people have said yes to you, maybe if you’re a startup idea going nowhere but at least you become a consultant and you can work on a flexible schedule. So speaking of which, how did you plan this out? You said right at the start that you had some runway in mind and you had a bank account, had something in it, and so on, but taking a break is obviously there’s a level of stress attached to it anyway. So how did you plan it out? So you could do it without too much.

Yeah. I think when I was first starting it out, there were really two main risks that I assessed. The first was financial, obviously, you have certain financial obligations, you have to pay the bills to make sure that numerically that this plan will work out. I think that was easy, but then there was another risk which was sort of a career risk because I think it is a pretty contrarian move and you don’t see a lot of people do this where they willingly and intentionally take a resume gap of six months, right? Because I think the conventional wisdom is you don’t want any more than maybe a month between your two jobs, because that’s going to look not good in interviews.

So I think on those two fronts, I had to have sort of a thorough plan to make sure that I was hedging my risk. And so starting with the first one about financial risk, that was a little bit easier because I have an operational and maybe banking background. I do track my finances on a month-to-month basis. I sort of know how much our household spends in a given month. And knowing how much we had in the bank account and then projecting that out with some cushion, I was able to say to my partner, Hey, I think we can realistically afford me going on this mini-sabbatical for six months without any sort of major risks to our ability to kind of continue living the way we want. Are you okay with this?

So, I needed her commitment and her buy-in on this as well. And then I think in terms of, the sort of consulting opportunities that came along, those are sort of the bonuses that came into your point. They extend your runway, they give you more room in time to explore, to dive into different curiosities. Had I not gotten some of those consulting opportunities, I think I would have had to probably start looking for sort of the next opportunity. Fortunately, because some of the consulting opportunities worked out, I can continue to do this for a little longer which is great because I’m still learning about a lot of things. I’m soaking in everything, which is great.

So it extends your runway a little bit, right? So that’s something that I think you need to treat as sort of a bonus that you’ll take if it comes along but plan for the scenario where that doesn’t matter in your lives right and then the second thing I think was what happens in terms of my career, how do I explain this on the resume and I think this is something that I feel really strongly about which is that you want to build in public and this concept of building in public is that you’re fully transparent about what you’re doing and you actually engage your audience to give you feedback to share their tips and ideas for what you’re building in public. So, you would write about it maybe on Twitter or blog or medium, in my case, on LinkedIn a lot and I have a newsletter. So, what I started doing was I started learning and building in public. I started sharing all of my learnings and what I’m building and my failures and what I’ve learned through that and how I’m pivoting and I’ve started documenting in all different types of formats.

So I have a website for Ops Hacks, the community that I run. I have the community itself with a lot of high-caliber professionals in there ready, that know exactly what I’m doing. I post on a daily basis on LinkedIn about what I’m learning. I have a weekly email that I send out on operations on things that are learned and then I’ve also started dabbling into DAO, which are short for decentralized autonomous organizations, which are sort of the latest kind of craze in the web three-space. So I’m putting all of this work out into the public and borrowing a web three-term again, there is this concept of proof of work, right? And what proof of work is that it proves that you’ve done the work and usually the work actually to do is really, really hard, but to prove, it’s actually very easy for other people to read that proof and say, okay, you’ve done the work right.

And I think it’s the same way here. Right? Like I put a lot of work into creating that content and really distilling all of my learnings into sort of more crystallized little nuggets of wisdom. And that takes a lot of effort, but for other people to see that and then think, okay, Joe actually has done the work. it’s relatively easy. So I can actually package that up as almost like a portfolio for myself. If this runway eventually ends and I have to go work, find full-time employment again, I can just say, Hey, look, this is everything that I’ve put out over the last six months. I would argue that perhaps I actually worked harder than some of your employees, maybe because I was actually pursuing my passion, but this is everything that I learned and this is not a resume gap. I worked on Saturdays. I just wasn’t getting paid for it.

Yeah. By the way, this episode is going to shoot to the top of the charts, because somehow you’ve managed to attach crypto and sabbatical together. It’s like the ultimate thing to kind of stitch together. That’s incredible, man. So, actually this whole proof of work, I really liked the explanation that you gave there. It’s a really good one and I’m sure it hasn’t really dawned on a lot of people that building in public actually acts like a resume. And in fact, like you said, better than a resume because you have something tangible to show. And there’s actual proof of the process, not just, two bullet points on a resume that says I did X and it’s a really good way to take a potential resume gap and make it into something more than, again, like a couple of bullet points.

Just getting back to a point that you mentioned earlier. You said at the start that all this began with no court, right? And it’s a topic that’s been gaining traction, the concept of building your product just by assembling tools and stitching them together with basically no code requirement. And we use tools as well. You mentioned Airtable, which is something that we use for our ops as well. So does that have a bearing on your sabbatical? Because maybe it makes it possible for you to get more done in less time. And so maybe a break can be shorter or something of that.

Yeah. I might be a little bit biased because I am very passionate about no code but I think, really to me, it feels like no code gives you superpowers, right? It makes you and enables you to create stuff on the web and it enables you to automate a lot of stuff, a lot of manual processes, which I think happened all the time in operations, which is a personal interest of mine. And so the way I think about no-code is, yeah, it’s a tool that you can if you leverage it the right way, can save you a bunch of time. And I think in the context of taking a mini-sabbatical and trying to get as much value out of that time off as possible, leaning on no-code tools is really effective because you’re able to create things a lot more quickly than if you had to code something. It might not be as perfect but you can get an MVP out a lot more quickly and then you can automate a lot of processes on the backend using no code again. On that point, I’ll just say that being able to automate stuff is actually I think an underrated skill in the corporate world.

So for example, right now, I’m involved in a couple of DAOs where people are figuring everything out and it’s all happening on a discord channel, and being able to automate a certain messaging and archiving on this score actually is like a superpower. So that’s what I’m kind of realizing. So I would say this is definitely a self-serving bias pitch, but if you’re going to go on a mini-sabbatical, and you want to experiment with creating things or, automating processes, definitely, think about starting with no code as your starting point because I think that’s gonna open up a lot of opportunities and doors for you.

Yeah. Thanks for sharing that because number one, it’s obviously good to know but number two, it should give a lot more courage to those who think that their idea is going to take forever to execute, or it’s going to take 10 people. And I mean, most of them should be engineers to make this thing happen and what you’re saying is that actually you can do a ton of stuff just by yourself or with very few people and in very little time. So, this is pretty insightful and hopefully, it’ll give some kind of confidence to people who want to try doing this. So I think maybe as a last point over here if you had to summarize all the learning for our listeners, what would you say? What should they keep in mind if they want to follow in your footsteps with a sabbatical-fueled launch?

No. Sitting down here today and talking with you, made it sound like I kind of knew what I was getting myself into, but in reality, I didn’t. So I think, this has been a good opportunity for me to kind of reflect back on my journey so far and the learnings that I’ve taken away from that and if I were to kind of maybe do it again today, I would really focus on four things. So I think the first is to start building and learning and go public as soon as possible. Start growing your audience because what’s going to happen is some people are going to be so interested in what you’re doing. They’re going to reach out to you and you can actually forge meaningful, interesting connections that might lead to other opportunities. If not, then you’re going to make friends along the way, which is always a good thing. And two from a more realistic perspective or pragmatic perspective, you’re going to be able to start building your portfolio in case the mini sabbatical doesn’t pan out until sort of a full-time opportunity for you. The second is you should, whatever you’re doing lurk and watch for as long as you can because the tendency for anyone who’s worked in a full-time capacity, as soon as they stop working, the momentum is there for them to want to pick something else up and start working on it right away.

But oftentimes what I’ve learned is that when you jump on those very first opportunities that you see, those actually turn out to be sort of fake opportunities that are not as actually very exciting after a few weeks. So it’s important to sort of resist that urge to jump into something immediately and to give yourself time and space to kind of breathe, reflect, and watch because then the really interesting opportunities will start merging in front of your eyes. At which point you’ll have the mental bandwidth to actually pursue them.

The third is to always think about creating quick feedback loops and I think this applies to context outside of mini sabbaticals as well. But giving you sort of my example, what I started doing was I started with a newsletter, which went out once a week and it was sort of a longer medium that took maybe a few hours per week of my time to write and what I started learning was that some emails would bomb, but then I wouldn’t be able to pivot or iterate on that the next day, I would have to wait until next week. So what I started doing was instead, posting on LinkedIn on a daily basis, and if any sort of topic, any certain topic really takes off and if any posts get a lot of engagement, then I know that was really good. Now I’m going to actually take more time to develop that post into a newsletter or an email. that requires more effort. Since I’ve built in this quicker feedback loop on LinkedIn, that tells me what I can do, and where I can allocate more of my resources.

And then I think the last and perhaps the most important point is that you have to enjoy the journey. There are multiple times on a weekly basis, for me, even now, where I asked myself, like, what am I doing? Is this something reckless? What do people think about this? There’s all these like self-doubt that creeps up, especially when you don’t have a company name that you can attach yourself to, or that you can absorb into your self-identity. But I think what helps in that instance is actually understanding that this isn’t just about how I up-level my career or how do I find that perfect dream job after this mini sabbatical. Treat the mini sabbaticals as a sabbatical where you’re actually taking a break. You’re actually learning time. You’re pursuing learning because it actually brings you joy and satisfaction because it fulfills your curiosity and whatnot. Treat it like that and actually enjoy the journey. I think that’s probably the most important thing because your mind tends to wander when you start thinking about three months ahead or six months ahead. But I’ll always focus on the present and just enjoy the ride, and see where it goes. Be open.

Wow. Thanks a lot, man. This was really fantastic. And at least for me, I feel like I learned a lot in this conversation. A lot of really good ideas, and a lot of very good tips as well. Actually for even those who may not be really going to do a sabbatical and, you know, take this in a semi-full-time, whatever their idea is.  But many of the points that you advanced actually could be used for people who are trying to do a side hustle as well. So really, all very good stuff. And I’m sure our listeners have a lot to think about as they mull over their respective business ideas. And really, we appreciate you very much, thanks for being with us here today.

And, for our audience, thanks for tuning in. Do remember to subscribe or follow to hear more such practical action-oriented talks from people who are actually doing it. And, so It was Joe and Amit on ShopTok. Thanks a lot, Joe, for being here today and, we’ll see you all next time.