Episode 720 | How to Prioritize Your Focus (In Both Your Startup and Personal Life)

Rob Walling:
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Welcome back to Startups For the Rest of Us. I am Rob Walling, and today, I’m joined by Craig Hewitt, the founder of Castos and the host of the Rogue Startups Podcast. In this episode, Craig and I talk through several topics. One of which is prioritization, and we went pretty deep on that, both prioritizing things from a marketing or growth perspective, in general when you’re working on a startup, how do you think through what’s a framework for prioritization, and also, we talk how to prioritize balancing work and life. I also talked to Craig a bit about what it’s like to be a founder and to start doing some coaching of other founders, and we also talk about what it’s like to have a podcast with a co-host and then suddenly be a solo host. 

Before we dive into that, you should check out MicroConf Connect at microconfconnect.com. This is our online community and forum. We host it in Slack and we’re approaching 7,000 members. They’re bootstrapped and mostly bootstrapped SaaS founders. Recent conversations in Connect, including a debate about magic sign-in links, how long you should spend diving into a niche before deciding on the product offer, how to safeguard your product from misuse during free trials, at what point in your journey should you invest in a conference booth and more. It’s a vibrant and highly moderated community, very high signal to noise. 

If you’re looking to find and hang out with other misfits like you and I, head to microconfconnect.com. It’s a great episode today. I hope you enjoy the conversation. The Craig Hewitt, thanks for joining me on the show.  

Craig Hewitt:
Yeah, man, thanks for having me.  

Rob Walling:
I hear from a lot of folks that they really enjoy the episodes of Startups For the Rest of Us that you’re on, so it’s good to have you back.  

Craig Hewitt:
Yeah, man. Likewise. It’s not a lot of opportunities to riff and BS on startup stuff, and you’re one of my favorites to do it with. So, this is awesome.  

Rob Walling:
Yeah, thanks. Yeah, it’s nice to go deep with other folks that you have chemistry with. This is what people tell me about these types of episodes. There’s the Derek Grammer and the Rubin, where it’s like you just have a rapport is what they say. You have a common language and you get there real quickly and you go deep really fast on things because there’s not a presupposition of, “Oh, I need to be really polite and walk on eggshells here,” or “I can’t say what I really think.” It’s like, “No, we’ve known each other for a very long time.” Oh, more than a decade. It’s probably like 10, 12 years, I would think.  

Craig Hewitt:
I think so, yeah. Yeah.  

Rob Walling:
So anyways, I came up with a few topics to chat with you about and then I realized that last week I had some success just tweeting out, “Hey, what do you want me to talk about with Derek Grammer?”, who was on the show a couple of weeks ago when this airs. So, I did the same thing for you, and what I thought was funny was you responded with one of my favorite topics. I was like, “Wait, the guest responded with the topic.” So your tweet said, “I want to talk through how you think about prioritization both from a marketing growth perspective, but also work-life balance and stuff outside of work with only so many hours in the day.” You want to give more context around what you’re thinking there.  

Craig Hewitt:
Yeah, I think part of it stems from just being a busy founder, have my own podcast, have content I’m doing, have a family, try to take care of myself and exercise, and try to have a garden. It’s summer and find myself looking at the calendar sometimes just being like, “This doesn’t add up.” So something’s got to give and I sometimes think I’m not doing the “right things”. So, I think that’s more so it’s like there are enough hours in the day if you prioritize the right things, and that’s within the eight hours of a workday and that’s within the whatever, however many hours we’re awake during the week. So, I don’t know. I would be very curious to hear how you think about it and I can share a little bit of what I think too, if that would be helpful.  

Rob Walling:
Yeah, for sure. I think we should both dive in on it. There’s a few things here. There’s a quote that I had in a talk one time that resonated with a lot of people, and I’ve said it a few times, but in your personal life, money saves you hours. In your business, money can save you years. What that means is if you have money in your personal bank account, you can pay someone to mow your lawn, your dishes, do your laundry. We have someone who comes to our house 5 or 10 hours a week and does errands and does basic stuff, $30 an hour, and then they’re local. They handle all kinds of returns and just anything you can imagine that an admin can do in person. It’s a hundred something dollars or 300, whatever it is. 

Sherry and I are two busy working professionals. We both have successful businesses for us at this stage that I’ll just say it’s a rounding error compared to we’ll go out to a really nice dinner with friends and spend that. So, it’s like that’s something that, and I’m getting it. I’m not saying everyone in the audience, you have $300 to waste on an assistant who comes in, but it’s like at a certain point, even early on, I started paying someone to mow my lawn. I remember I had friends who made fun of me for that and said, “You don’t want to put in the hard work,” or like “Oh, you’re a real bougie now, aren’t you?”  

Craig Hewitt:
Sideways.  

Rob Walling:
Yeah, these were the friends that I had to distance myself from to become an entrepreneur because they had this old script. Let’s say I was 25, 26 and I was making $60 an hour as a developer hourly. It was contract. I could work 10, 12, 14 hour days back then and I would get paid for 10, 12, 14 hours a day times 60. So, really the math was there. So, instead of me buying a lawnmower, maintaining it, and doing all this stuff, I would do that. I started hiring more out and I was really guilty about it for a long time of like, “Am I wasting money? Because I could just go do that on the weekend.” Same thing with cleaning my house, that was a tough thing for me to get over. 

So, that’s a very basic first one, but I think people don’t delegate or outsource enough in their personal lives. To be honest, man, is it easier to find someone to come into your business and do support, customer success, and train them on that, or is it easier to find someone who can run errands and do laundry and do a few things and the cost might be similar or less? So that’s a super tactical one to start with, but I want to toss it back to you in the sense of how you think about trying to prioritize these things.  

Craig Hewitt:
Yeah, so totally on the money buys you freedom or time. Dan Martell’s book, really good, Buy Back Your Time. I know he’s been on the show, really, really good book from a business perspective. I’ve been on and off with assistants. Actually yesterday, two days ago, I signed back up with Zirtual. That’s how I had my assistant before, signed back up with them. I think they started like 500 bucks a month for 12 hours a month, so a couple hours a week. For me, it’s just like, “Can you take care of this notice from the State of Virginia that I literally have no idea what to do? Can you just please go take care of this?” They’re pretty senior level folks to where you can say, “I just don’t want to think about it until it’s done please. Here’s the SOP and the documentation, but solve this problem for me.” 

Outside of work, what I have tried to start doing is just less. Instead of just saying, “How can I possibly manage all these things?”, I’m just like, “I’m not doing that.” A good example is I was going to CrossFit for a while and it’s a really great workout at 44 now. It’s maybe a little too much for my old ass, but one of the challenges was it’s at 5:00 or 6:00 in the morning. So, then that’s very fixed and the rest of my day has to fit around that. So, I’m like, “No, because what I need is a thing that can fit around my schedule.” So it’s like let’s break down the rigidity and the barriers to where I can just do my stuff whenever and however I want. 

So, I think that it gets at the same concept is like how can I bend the reality to fit more what I want? That’s been away from work. Something I’ve really tried to do is just optimize for convenience as much as possible. We haven’t gotten someone local, but that’s probably the next step is get somebody a couple hours a week to help with the house or stuff and groceries and things like that.  

Rob Walling:
So I actually contacted Zirtual and four other VA agencies and said, “Do you have anyone? I want someone local and I want an EA level person, but I want them in Minneapolis,” because I want them to be able to do the stuff you’re saying, which is this tax notice. Or I got something from my insurance company the other day, and again, it’s like, “I need you to make a phone call and I need you to figure this out,” or “I need you to change this plane flight. It’s going to be like 30 minutes on the phone with Delta. Can you just do it? But I also want you to be able to run these errands because there’s just enough in a week with us around.” 

We actually found a friend of a friend who’s doing it for us now, but more than that, I like what you said, it’s not just about hiring stuff out. It is about doing less. This is the thing I realized is again, going back to when I was 25, I would sometimes code 12 or 14 hours a day because it was just like, “I’m going to make money because I need to make money to pay the rent and to be self-sufficient.” Sherry and I were married already at that time. Then as I started becoming an entrepreneur, I transitioned into that mode where I’d work all day and then I would entrepreneur all night till 1:00 in the morning or something. So, I would work a lot and then even as I became an entrepreneur, I was like, “Well, I will just grind it out. That’s how I will win.” 

That was perhaps a good choice early on, but there’s a question mark on there because grinding it out and working 12, 14 hour days, which again, I did as both a contractor and then doing products for a while back when I had time, no kids, all this stuff. I worked on a lot of the wrong things. I wasted so much time, so much time. I mean probably half my time was wasted, maybe more where I just didn’t know what I was doing. I wasn’t asking for advice. I wasn’t following rules of thumb, didn’t have a plan. I just flailed around and did the next thing because I was like, “Well, I’m going to keep working. I’m going to keep working. I did stuff.” It took me a very long time to hone that ability to say no to a lot of things and pick. There’s no one right thing to work on.  

Craig Hewitt:
There’s a whole lot of wrong things.  

Rob Walling:
But there’s a whole lot of wrong things. If there’s 100 ideas, there’s probably like three or five that are probably in the 80, 90% correct. It’s in this direction. How do you identify those? How do you do that? Do you think about it?  

Craig Hewitt:
Yeah. So, I have a really good one there. So, this is on the work front. I have several people that I work with, I actually wrote about this in my Founder Insights newsletter last week. It’ll show up as a blog post on craighewitt.me if you want to go check it out. But what I’ve started doing is really leaning into having several different coaches in my life. So, I have a wellness coach from My Body Tutor. Amazing. Check it out if you haven’t. I have a sales coach now and I’m a sales guy, so I should know what I’m doing. But I think it’s a testament to even if you are the subject matter expert, having an objective third party unbiased person to bounce ideas off of and say, “Hey, I want to grow this part of my business. What do you think about this or this or this as an approach?” 

They with probably a whole lot more experience and context and perspective would say, “Well, obvious just do this.” Then I have a founder coach who at a higher level strategically, I’m able to say, “Hey, we want to do this,” or “We want to acquire this company,” or “We want to raise more money or whatever.” He’s able to really give me the same really honest feedback. So, that’s something I’ve really benefited from a lot in the last year or so is just not putting all the pressure back on me because as founders, you got to make so many decisions every day that especially as a solo founder to say, “I got to make this other decision,” and then it’s the next one and the next one and the next one. 

Some of them are really important and you have a mastermind group or you have a mentor or whatever, but you got to have somebody to talk to, I think, is the point. To me, paying someone who has actually done the thing is way more valuable than pretty much any other peer group because that is then the answer. You have a relatively high confidence that that’s right.  

Rob Walling:
If you can find someone that you trust in a domain to give you their best advice, and here’s the thing, if you trust them, it’s likely they will say things like, “I feel very strongly that you should do X” or… I’ll do this all the time with tiny C founders. I’m on the fence. I’m going to be honest. I think you have two viable options. Let’s name the other. There’s five total. I think these three are garbage. I think you have two, and I’m struggling to know what you should do, but it’s pretty obvious it’s one of these two and then I’ll pass it back. What do you think? What’s your gut? Because you know your business better, you know your customers better, you know whatever this space better than I do. I know the best practice is probably better than you do, and we’ll do that. 

I think a good mentor, advisor, or even friend, mastermind, whatever, couches things like that. They’re not so certain of everything, but then sometimes, sometimes it’s really, really obvious what you should do. It’s like, no, I’ve seen exactly this 10 times and 9 out of 10 times that this was the right, that type of thing. You can get to that point of certainty. That’s a huge win. These days. I try to think about how I make decisions. Well, A, I try not to make a ton of decisions all the time, and that might sound weird, but it’s like you have to make a lot fewer decisions than you think. The key phrase, have to. There are a lot of things you just don’t have to decide. 

I think in the early days of a startup, you have to make a lot of decisions quickly of, “What am I building? What are we doing? ICP, I got to move faster.” TinySeed was like that. MicroConf was like that. Drip was like that. But you get to a point where it’s like, “Oh no, we don’t need to decide about that. We’re just going to let it run. What’s working is working. We’re going to keep doing that.” That’s a skill. They often talk about retail investors, just consumers who day trade and they buy this stock and then they buy this index fund and they sell it because they read something in Bloomberg and then they do this and that. It’s flailing. It is tax disadvantaged. Almost no one does that. You have no advantage in that. 

I feel the same way about some founders who are like, “What’s working is right now for you, it’s like SEO and cold outreach or whatever it is, but it’s a grind.” No, shit. It’s always a grind. I don’t care if it’s a grind. Is it working? Yeah, yeah. We’re growing two grand MRR every month. Then why would you make any decision? Just keep doing it. It’s like I know that you want to day trade. You want to do something more exciting. The most exciting thing is new MRR.  

Craig Hewitt:
So I have two things around this because this is really hard. We are at the point in our business where it’s getting a little boring in a good way, to your point, and that the challenge, one, is you as a founder accepting that like, “Hey, just tune out all of that stuff and focus on the stuff that’s working.” You have to get over that. Then what I’ve found is you have to get over this next hump, which is you have to relate to your team that that’s how they need to think too. Because hopefully, your team is like, “Oh, hey, what if we do this? What if we build this feature? What if we support? What if we do this?” I think about this movie, the Yes Day, but in the movie they’re like, “I’m the fun guy, and you’re always the one that’s saying no,” the parents. 

I feel like the parent that always says no to the team because they’re like, “Hey, what if we do this? Hey, what if we do that?” I go, “No, what if we don’t do any of that stuff and just focus on this really narrow thing?” What you’re saying to the team is like, “Hey, we have to focus and prioritize.” If you do it wrong, which I think I might have at the beginning, what you say is let’s just dial back the intensity a little bit. That’s not exactly right, but it is, right? Because what you’re saying is we’re going to do less. We’re going to do it better and it’s going to be better for the company. It’s a very different mindset as a founder for sure. But even I think if you have entrepreneurial team members, they go, “Whoa, I only have to do this one thing. That’s crazy.” I have a little bit of insecurity around that.  

Rob Walling:
Yeah, I could see that. I am guessing that’s where sprints were invented. We’re going to do a sprint. Whether it’s two weeks or three months, you hear marketing sprints are sometimes two or three months and development sprints are two weeks. Lock it in. Can’t change it, pretty much unless there’s a [inaudible 00:16:56].  

Craig Hewitt:
Yeah, put one the blinder.  

Rob Walling:
Yeah, because everyone has ideas and some of those ideas are good. There’s this Steve Jobs quote I mentioned offline, but I think that I quote him in my book, whatever. I don’t like it when people use Steve Jobs as an example, blah, blah, blah. He’s such an outlier. It’s like, “I’m going to use it to justify his really dumb thinking. Oh good.” But Steve Jobs says, “Focusing on stuff and building great things is not about the focus. It’s about saying no to hundreds of really good ideas.” I think about that quote so often of, “What is the one or two things that I should really be focusing on?” And then my next step if I’m going to do something in the business is how can I find someone who knows more about this than I do? 

So when we were going to start YouTube, we futzed around with it for a while, and I realized pretty quickly I have to be able to pay someone who just can get us there faster. We did. We hired a consultant and they were not cheap. They were several grand a month for advice, which I struggle with as a total cheap ass, a guy who grew up without money, but I’m like, “Dude, if I can grow this channel, it’s worth it.” It did, right? We’re at 80,000 subscribers or something. We grew very quickly, and there’s other stuff I’ve looked into. It’s like, “Oh, should we do TikTok? Should we do LinkedIn? Should we do whatever?” These are decisions I have to make, but I make them very slowly until I’m pretty damn sure that it’s the right one.” 

Then I’ll go deep and I’ll go really fast. I will spend a lot of money to have someone tell us exactly how to do it, maybe even to do it for us, depending on what it is that needs to be done. Then I will go all in. YouTube for us was I was shipping 52 videos a year at relatively high quality if you go watch them and 15 grand, 18 grand a month spent it on that, which is a lot. You might say, “Wow, that’s a lot of money.” It is a lot of money, but I deemed that I was either going to do it or I was not. What I wasn’t going to do was take that 18 grand, split it among, well, let’s try three or four things because guess what? Really low probability that any of them would’ve worked.  

Craig Hewitt:
It is what’s a good idea that you can execute on and that’s your skills, the people on your team, the people available is you, the money, all that stuff. This makes me think of is this book, Who Not How, and I’m blanking on the name.  

Rob Walling:
The author.  

Craig Hewitt:
Yeah, but that’s it, right? It’s like when there’s a problem at a point when you have the resources, who can I hire to help me solve this or solve it for me? And then your goal is just to define what good is and let them go.  

Rob Walling:
Dan Sullivan.  

Craig Hewitt:
Dan Sullivan.  

Rob Walling:
Just looked it up.  

Craig Hewitt:
Amazing guy.  

Rob Walling:
You recommended that book to me a couple years ago and I got the Audible version of it.  

Craig Hewitt:
I think that one’s from Rubin.  

Rob Walling:
Is it? This is what happens.  

Craig Hewitt:
Rubin, the press, yeah.  

Rob Walling:
Rubin has the A method for hiring. That one came from Rubin. There’s a few. There’s a few of those. Yeah. So, it’s interesting. A, I make fewer decisions than most people these days. I used to make all the decisions. I’m going to do the stuff and flail around. It’s like that was something that as I matured, I realized, “Oh, that was not the right way to do it.” I should make fewer, more important, more focused decisions. As a result, my decisions are bigger and tend to have bigger consequences, I’ll say. Because when I committed to this money and this recording these videos, which is a lot chunk out of my week every week, and I wasn’t very good at it. It took me a long time when I started. So, I knew I was investing. 

But when I make those decisions, I think I mull it over for a few months usually if I have that luxury. Sometimes you don’t, but several weeks and then I start going to people. What do you think about this whole thing? We have this idea. So, Rubin, what do you think about that? Each of them has a different perspective. So, Sherry, what do you think about this? It’s like I get all these different inputs, mastermind, co-founder, whatever it is. I’m talking to a listener right now of how to make hard decisions. It’s like who do you have in your life? If you don’t have someone, then you might need to hire someone. Like you said, you have coaches. I have a therapist. I’ve been seeing a therapist for years on and off. 

There’s this stigma around it of like, “Well, you’re seeing a therapist, you must have (beep) wrong with you.” A, all of us have (beep) wrong with us, so please don’t kid yourself to think otherwise. For me, it’s self-reflection. She’ll tell me, “Here’s what I’m hearing you say.” I’m like, “Huh, why did I say that?” She’s like, “I don’t know. Let’s figure out why you said that. You obviously are programmed to have this limiting belief maybe.” So sometimes I’ll talk stuff through with her as well. I wouldn’t talk through a YouTube launch, but I would talk through a hard decision that I think has a mental component. Sometimes you know what’s the right decision? But you can’t do it. You won’t do it and you’re avoiding it because it’s making you uncomfortable. That’s when I’m like, “I need to talk through why I’m uncomfortable and figure out-”  

Craig Hewitt:
This is okay.  

Rob Walling:
Is it because the way I was brought up as a kid? Is it because I didn’t have money in my 20s and I’m scared of always going back to that or whatever? Are those the reasons? We’ve talked a lot about decision-making in professional context, which I think is helpful. I know people often like to hear, especially the folks who listen to this podcast that are further along where it’s like, “Oh, I’m doing a million a year, five million a year.” This type of stuff, we all struggle with it, but let’s talk about the work-life piece. In terms of family time, we both have families. When my kids were younger, I definitely struggled. My kids are older now. They’re almost 14 and 18. So, they’re self-sufficient. It’s having a roommate rather than a kid. You know what I mean? 

They put themselves to bed at the time that they should go to bed and they wake up in the morning. If I make breakfast, they eat it. Otherwise, they make it for themselves. So, it’s different with younger kids. That’s one thing I will say is if you have young kids now, realize it won’t be there forever. They will get older and you will be able to leave them alone overnight for multiple days at a certain point. It’s mind-blowing when I say that, right, but we haven’t hired a babysitter in years because it just changes. You can, right? But it’s like realize that this time is only a few years, however that few is. 

So, with that caveat, I will say that much like making fewer decisions and focusing in my professional life, when I’m with my family, well, A, I try to have really interactive, meaningful time with them where it’s like, “Dude, let’s play a game together.” My 17-year-old, he’s almost 18, is home from college for summer. I’m like, “I’m off calls at 3:00 today. You and I are walking somewhere.” We’ll go on a walk for an hour, 90 minutes. We’ll go somewhere. We’ll get ice cream. It’s a great day here in Minneapolis. I’m just very deliberate about that. We don’t need five hours together tonight. That one hour, we will have so much conversation about so many things about our lives, about what I’m thinking about. He asks me about work. What’s going on with this and are you stressed about that?  

Craig Hewitt:
That’s cool.  

Rob Walling:
You know what I mean? It’s not all perfect. It’s not all amazing and it’s harder. If my kids were two and four, it would be a different story. Both of us can weigh in on there because we’ve been there. But I think that’s been my realization is it’s similar of if I’m going to spend time with them, focus it in a way that is very meaningful. 

We watch movies or watch YouTube or play games or do other stuff. I’m not saying it’s all just this intense conversation, but if I start feeling myself distracted or not wanting to be there, then I’m like, “Okay, check yourself. Should you just switch to something else and come back to this? Come hang out with the kid in an hour when you really are able to focus on them, or do you have something going on that you need to deal with?” So how do you think about this? You have younger kids.  

Craig Hewitt:
So I have 11 and 13-year-olds, and they’re getting to this point. We haven’t hired a babysitter in a while, but they can’t stay by themselves overnight. A couple hours, we can go to a dinner or a movie or something. Absolutely. The biggest improvement for me has been this intentionality and separation of there’s work time and then there’s just hanging out together time unstructured. There’s me being more intentional like, “Hey, let’s go play basketball” with my son, or hey, let’s go walk the dog after dinner with my daughter or something. To boot, my wife started working again about four months ago for the first time in 13 years since our daughter was born. That’s an understatement. 

That’s been a really big change in our life and family dynamic is wow, for several days a week now, she’s just gone and I’m the only one. I’m working and responsible for the kids. So, I’ve just had a lot more this is it. At 3:00, I’m at least flexible because the thing is the kids come home and they’re fried because they’ve been at school for six or seven hours. They just want to hang out and play Fortnite or whatever. So, I will mix that time is I’ll just grab my laptop and go downstairs and sit on the couch and futz around. But what that means is the really super important (beep) has to get done in the beginning of the day because I know I got to create this proposal, I got to follow up on this email. That’s just leisure, work time. 

So, that’s how I overlapped the two. Then at 4:00 or 4:00, cool, done, put the computer away. The computer comes back to the office. So, it’s not physically in the space where we are as a family and then we do stuff. We’ve started cooking together a lot more. That’s a really cool thing. Then yeah, same here, we have a garden and my son is in charge of getting the salad every night from the garden. So, there’s just little stuff like that. Empowering them with chores and activities that we can do together are really cool. So, as much as you can extrapolate that out, I think, into your life, it’s positive.  

Rob Walling:
Yeah, that’s really good. Those kids will remember that for probably the rest of their life. Not every moment, but they will remember, “Oh, I remember getting stuff from the garden.” If they do it 20, 50 times, whatever, it’ll just all be an amalgam of a single memory. But for sure, I have a bunch of stuff like that from my childhood. I don’t want to paint this as like, “Oh, if you have a two and a four-year-old or four kids under eight or whatever-”  

Craig Hewitt:
You’re screwed.  

Rob Walling:
It is just a lot more challenging, but it’s even more reason to focus relentlessly and try to figure out the right things to work on. In a business, to me, it’s this dichotomy of risk versus certainty. It’s like what’s the riskiest part of the business that needs founder-level thinking? That’s what I’m focused on. Anything that has certainty in a SaaS company, it’s like if you’re two years into a SaaS, you know that someone can answer support requests. There’s an SOP and most of them can be answered. There’s a knowledge base, whatever. Frankly, writing code, I know it’s a craft. I loved writing code and I was a craft person when I did it, but someone else can build that feature, but most other people can’t design that feature. That’s the thing. 

Designing it or crafting it or saying exactly how it should operate, product-level work is quite hard to find because your knowledge of your customer need there is founder-level need until you can hire. I mean the first product person we hired, we were doing several million in ARR, and his salary was $165,000. I mean it was really expensive. He makes more than that now. It’s like that’s the level of product person who can take stuff off your plate who’s been doing it, but there are always elements of risk and always elements of certainty in a business. I think that the certainty is that’s where your comfort zone is. 

So, unprodded you will slide into the comfort zone because it’s like, “Oh look at so much work I’m getting done” and then you work 12 hours on something that really should have either not gotten done or should have been delegated to someone else.  

Craig Hewitt:
Yeah, I mean the rule of thumb I use there is… This comes from my coach, Mike Del Ponte is like, “Do the work that’s as close to the customer as you can.” Typically, that’s sales that. That’s the best, right? It’s like, “Can I go talk to this person and sell them a thing?” After that, I agree. It’s probably either marketing or UX product design because that’s more of a one-to-many. Then the things that are way down on the scale are like, “How do I grow my falling on Twitter?” Even should I start a podcast? I don’t know, maybe, but only if you think there’s real potential direct impact. I think a lot of the time that we waste as founders are on brand marketing. If you’re at a few million, maybe you can allocate 20% of your marketing budget to brand marketing, but until then you got to be hand-to-hand.  

Rob Walling:
Yeah, yeah. You’re not a media company, right? That’s not what we are as bootstrap SaaS companies and thinking you can do that quickly and it won’t be a waste of time. It’s pretty rough. Same thing with, “Oh, you should build an audience in order to build your…” Oh, that’s a real long way to do it. I built an audience. I built multiple audiences over several years and it’s 15 years or whatever. It’s way more time than sales you will make if it’s for SaaS, but if you want to sell info products or courses, that’s another thing.  

Craig Hewitt:
I say it for all the people who are yelling at their phones right now, I say that because we made that mistake. We thought, “Hey, we’ll do a bunch of brand marketing and it’ll really result in a lot.” It didn’t. Now we’re much more one-to-one and we’re growing faster than we were when we were a team of 15.  

Rob Walling:
So let’s switch it up. This is a great topic and I didn’t want to cut it short because I think there’s a lot to be said about it, but we did have other folks weighing on Twitter about stuff, and I want to get to their questions. Christopher Gimmer asked, “I’d like to hear Craig talk a bit more about the coaching he’s doing, the pros and cons of it. When he felt confident enough to start offering it, would he recommend other founders do it on the side? Does it attract from the main business, et cetera?”  

Craig Hewitt:
That’s like four questions.  

Rob Walling:
It is.  

Craig Hewitt:
How did it come about? A bit of the focus that we talked about is we had just said no to a whole lot of things and I found myself with a little bit of time. I didn’t have that thing where I said, “Ooh, if I had 10 more, I could spend these 10 hours in the week to do something and it would move the needle.” So I said, “Well, I can spend these 10 hours in the week doing this other thing that I really enjoy. I’m pretty uniquely qualified to do and it would be helpful and I can make a little bit of money.” So that’s how it came about, and it was just very, very, very slow. I think I wrote a LinkedIn and a Twitter post about it maybe. I sent an email to the 200 people on my newsletter about it and got a couple of clients, got a couple of referrals from that. 

So, at this point, have a handful of folks that I’m coaching and it is the ICP’s founders, typically SaaS founders who are looking for help growing their business, so sales and marketing. We work together every other week for an hour and I want them to come with the biggest challenges they’re having. That can be anywhere from review my cold email sequence to how do I think about managing this sales rep to here’s my org chart, where do you see the holes to I helped someone go through an acquisition where they were acqui-hired. That was super cool. So, I mean, all the (beep) that I did, that you and I’ve done is I’ve done this for folks who are looking to do it, just like we talked about before. 

It’s like, “How can I pay a little bit of money or how can they pay a little bit of money to get a few years ahead?” Is it a distraction? Actually, I think I’m a much better founder now because of doing this, because part of it is I see a lot more, right? I see in the market how people are doing things, and so you have a lot of visibility through TinySeed of all the companies. I have a much smaller percentage of that, but also, I got to walk the walk when I am talking to a founder and they’re like, “Oh, I was thinking about doing this and I’m thinking about doing that. I’m thinking about doing the other.” I go, “Do the thing that’s as close to the customer as you can,” and then I hang up the phone and I go futz off to do some SEO thing. 

I’m like, “Whoa, Jack, that is not what you just said. So, you got to walk the walk.” So yeah, I think it’s not that much time. It’s definitely not that much mental overhead or stress because it’s just a call and I really, really, really like it. So, there’s that. It’s like sometimes you got to just eat the ice cream and that’s a bit of what it is.  

Rob Walling:
Yeah, I think that makes a lot of sense. I would guess for some founders, it would be a distraction if they were in super grind 10 hour, 12 hours a day, all consumed with their business and they’ve never done coaching, because just because you can do something doesn’t mean you can coach other people on it. I’ve seen some coaches who are so sure of their point of view because they had a success or whatever, and they’re like, “No, everyone should do it.” So then every call, it’s like, “No, you should do this. You should do that.” It’s like that’s not coaching. 

Coaching is more asking questions and figuring out, “Hey, what is really the best option?” Usually, there is no one best option. There’s a couple options that are viable based on criteria, but I do think that you were in a spot, you are in a spot with Castos where you’re five years, six years in, seven years, depending on how far.  

Craig Hewitt:
Seven. Yeah.  

Rob Walling:
At a certain point, as the business matures, it does require I think less. If you’re doing it well, you are delegating and it requires less and less. Even if it requires eight hours a day from you still, less and less founder cycles because it comes back to risk versus certainty is how much risk is left. There’s a few areas of risk, meaning uncertainty, or just founder level thinking, but you’re not making the same number of decisions on a day-to-day basis now than you were four years ago, five years ago, right? It’s that good glucose, as Dan Andrews says, to be able to coach, because I tell you what, coaching is… I don’t know if you find it this way. It’s very tiring. I say that in a good way, but it grinds me down in terms of you’re going to present me… 

The only problems I get, because I obviously do this through TinySeed. The only problems I get are ones that talented, gifted, handpick founders don’t know the answer to. So, it’s all the hardest problems. I consider that an honor and an amazing thing, but damn if it does, it just burn through my brain cells because I’m like, “All right, tell me again and let’s get it all in.” Then I’m like, “Oh, this is hard and it matters.” So I’m not going to half ask this decision, so let’s dive in. I’m taking notes, I’m thinking through. It’s like whiteboarding a new feature where you’re going deep and you have a mental model in your head of ba, ba, ba, right? 

So for me, coaching is exhilarating. It keeps me in the game, exactly what you’re saying. I have 192 companies and I’m like four, five, six, seven conversations a week depending. But those ones I end and I’m like, “I need to go for a walk because I’ve just expelled a lot of good…” Talk about decision making fatigue almost. It’s like I’m in that helping them make hopefully the best decision. So, that comes back to if I was 8 to 10 hours a day on a startup and I didn’t have that energy to do it, I wouldn’t coach, but again, I feel like you’re in a pretty good spot where you were ready for it and you’re highly gifted at it as well.  

Craig Hewitt:
Yeah, it’s interesting. I don’t find it draining at all, which is a really good sign. I think I did a bit of it for free and found I really liked it. I learned a ton about this whole giving advice versus asking questions. I’m like way, way better coach now than I was at the beginning, but yeah, it’s exhilarating in a very healthy, appropriate way. So, to me, that’s a really good sign that it’s probably a pretty good place for me.  

Rob Walling:
Sounds like it. Yeah. Our last question from Twitter comes from Matt Paulson, longtime listener of the show, and I presume of Rogue Startups as well because he says, “The thing that the two of you have in common is you both used to have podcast co-hosts and now you don’t.” I think the implied question there is maybe what was that experience like? I don’t know you need to say better or worse with a co-host or without, but is that maybe hard? Was that a learning curve? What was it like for you to transition?  

Craig Hewitt:
Yeah, so just for context, I have a podcast called Rogue Startups where started as just me, and it was an interview-based show. My third guest I think was Dave Rodenbaugh, who then became my co-host for the next 290 episodes, for the most part, over six or seven years. I mean, we’re a very long time into it. I just published episode 314 this week. Yeah. So, Dave and I largely had just a co-host show where we just provide updates on what’s going on, a lot like you and Mike did, sometimes interviews, all this stuff. Then really through COVID, it was really hard for everybody. A little bit after, Dave was like, “Man, I don’t care to continue anymore,” is I think what he would say. To me, maybe to you, this is super important to me. 

If you want to use the term brand, it is probably my biggest aspect of my personal brand, which has some importance. So, I was like, “Cool, man, I want to continue. Are you okay with that?” He said, “Yeah, this is just not for me, so not for me anymore.” So that’s the context. Yeah, it was super hard. It was super hard. In a way, I was really excited because I was like, “Cool, I get to continue doing this thing that I really like that has been the catalyst for a lot of my business stuff.” But then I was like, “Whoa, when you have a co-host, it is that mirror of energy a lot,” right? Hey, let’s just hop on. I don’t have a lot to talk about, but (beep) Dave just did this thing. Cool. That’s the episode for the week. 

Now, I don’t know what to do. I got to find a guest, I got to find an interesting guest. Because the last thing I want is to get whoever to come on and talk about SEO again. I always say when we’re advising our customers at Castos, like you got to find the person, you got to find Rob Walling, who everyone has heard on podcasts to talk about something you’ve never heard him talk about, which is pretty challenging. Or you got to find the person who no one has ever heard about that’s going to blow their mind. That’s slightly easier, but still pretty challenging. Both those things just require a lot of effort. 

So, I’m fortunate to be networked pretty well in the entrepreneur podcast community, have probably taken a lot of similar steps to you of don’t have as many guests as rotating co-hosts. Then I get the most good feedback from my solo episodes. So, aside from my episode with Jason Cohen that went out two weeks ago, I only get positive responses to my solo episodes, but they are soul sucking and I can only manage about one a month. So, having a co-host to your podcast is by far the easiest way to have a podcast. Not doing it is really hard, but I’m glad the podcast is continuing on. I guess that’s the short version.  

Rob Walling:
I think I feel the same way. I agree fully with you that having someone else on the mic is you can show up with almost nothing to talk about and fill time with pretty intelligent and entertaining things. Doing that solo, like you said, if you don’t plan for it, you’re on your own and what are you doing then? You are either answering questions or you’re just coming up with a topic and then talking to nothing for 20 minutes or 30 minutes or whatever. You’re right, those were really hard for me. They’re less hard now. Now, I have more confidence in my voice or there’s just something that shifted where I was like, “Okay, I am just going to say…” I used to filter a lot more if I’m honest. 

I was like, “Oh, what if I have shown my real personality?” or “Maybe I shouldn’t be so opinionated, but maybe this will make someone mad.” I’m not going out with super scathing hot takes or anything, but you might notice that over the past, probably four years, five years since I went solo, I have just become more opinionated about certain things, about certain anti patterns and certain success patterns that I see over and over. That makes it almost easier because I don’t have to censor myself as much on the solo episodes where I used to start, I would say a whole paragraph. Then I’m like, “Oh, what if that makes someone feel bad? Editor, just cut that whole thing.” So it was just a start, stop, start, stop. It wasn’t that fun. 

I was always worried, “What am I going to talk about? What topic can I possibly talk about?” Now I have this huge Trello board because stuff just hits me. As I consume things, I listen to audiobooks. I hear other podcasts like yours and the other ones I listen to. Oftentimes it’s something completely outside of startups like the Comic Lab Podcast where it’s these two artists that are independent comic guys and they publish their own books, not through publishers. They do Kickstarters and Patreons and all that. They’ll say something and I’m like, “Oh, that totally applies to startups, and I’ve never heard-”  

Craig Hewitt:
Oh, that’s cool.  

Rob Walling:
Yeah, I’ve had three of those probably in the past six months where I brought it on the show. Then there’s even Dungeons and Dragons podcasts or metaphors with games or something. I’m like, “Oh yeah, that is a thing.” The thing I’ve really enjoyed about it, I think, is I definitely wanted to experiment with a lot of formats and just experiment with things. I mean, if you’ve listened to this show for any length of time, you’ve heard me bring in Beatles music and I forget who else I brought on, but different. I’ll talk about a song and then I’ll bring the song on. It’s super cool when you listen to it, but it’s a weird thing to do on a startup podcast for the first time. 

It was something when I had a co-host, I was like, “Oh, do I check with him? Is it weird to do a solo episode if I have a co-host? Is that pulling the spotlight?” There was all this stuff that I was concerned about experimenting with, and I think that was maybe to the detriment of the variety of the show. Because after Mike stepped back, I tried a lot of stuff and actually a bunch of formats that I don’t do anymore, but I tried them. They were forgettable, the formats. People just weren’t that interested. The ones that stick are the ones that people comment on and they say, “Oh, I really like that.” Similarly, the solo episodes always resonate. It resonates with somebody.  

Craig Hewitt:
If I could, I think the thing that brings this full circle to business is nothing’s forever. You won’t do this podcast forever probably, or you won’t be the host of this podcast forever. I don’t know. Maybe I’ll run Castos forever, I don’t know, but you won’t be at your job forever. You won’t have the same co-founder forever. Maybe you’ll stay married forever. That’s cool. I hope I do, but I think to go into most of these things expecting it to be forever is setting yourself up for disappointment. Going into it a little eyes wide open and setting expectations with a co-host or with a co-founder, you talk about, “Hey, if you go into a co-founder agreement, have (beep) in writing.” 

Maybe with a podcast co-host, it doesn’t need to be a legal document, but an email to say, “Hey, this is it. We’re going to check in once a quarter. If anybody wants out, that’s cool. This is the process.” I didn’t have that because Dave and I just started podcasting and backed our way into a partnership. If I did it again, I would be a little more intentional to say, “This is the situation now. It probably will change, and these are the parameters around how it can change.” Just there’s no hard feelings and there weren’t with Dave and I. I don’t think there were with you and Mike. It was just the right time to start doing something different, but it doesn’t always work out that way.  

Rob Walling:
Yeah, I like that. Nothing is forever. Everybody sells eventually. Everybody sells eventually. Never thought Mailchimp would sell. You’re right, podcasts either fade or they change, different co-hosts. Like Calacanis on This Week in Startups had Molly Wood as a co-host. Then Molly Wood disappeared and there was never anything mentioned about… I mean, I shouldn’t say she disappeared. She stopped being co-host suddenly, and there was never a conversation about it. Now I think he has a new co-host, but that’s a thing, but what is he, like 1,200 episodes in or 1,300? I don’t know. He’s a lot of episodes and it’s like that’s just how things happen when you do them for 14 years. They do change, and this podcast is episode 700, whatever, 19. 

It’s 14 years, about 14 years in, similarly. So, just expect that you roll with it or you quit at some point, and that’s okay. There’s a pretty good book called Quit. What’s her name? She’s the poker player, Annie Duke. It just came out. I will admit, I could summarize the book in about a three-minute Loom. There were some key takeaways that I thought these were really good, and there was a lot of stuff that I was just like, “Eh.” But if you can read a summary or listen to the audiobook or whatever, it’s interesting and not a justification, but a defense of like, “Hey, sometimes you should quit.” 

There are times when you should stop doing things, and it’s a good reminder because society somehow has this big stigma around it, but I know some people where them quitting either a business or a relationship or some other effort they’ve done for a long time was actually the kickstart of a whole new chapter in their life. So, it’s always something to keep in mind. Craig Hewitt, thanks so much for joining me, man. You are @TheCraigHewitt on Twitter and craighewitt.me if folks want to check out your email newsletter. Thanks again for coming on.  

Craig Hewitt:
Yeah, man, thanks for having me.  

Rob Walling:
Thanks so much to, Craig Hewitt, for spending a few minutes with me today and providing you with your weekly dose of Startups For the Rest of Us. I hope this is an amazing week for you both on the personal front and also in terms of your business goals. Thanks for listening this week and every week. This is Rob Walling signing off from episode 720.