Episode 600 | When to Hire Your First Manager + What You Should Be Focused On (A Rob Solo Adventure)

Rob: How many founders do we know, myself included, who burned parts of ourselves mentally, physically, and emotionally to be more successful at an action or to be more successful at our company? It is taking aspects of yourself, grinding them down, and giving it to this other entity so that it can succeed.

Welcome back to yet another episode of Startups For the Rest of Us. I’m your host, Rob Walling. I’m doing a Rob solo adventure this week. I’m going to talk through some thoughts and mental frameworks about certainty versus uncertainty. Which things should I be working on versus delegating, supervising versus leading? Might even touch on a concept called spell burn and talk about thought processes behind when things take iterations and how to know if you’re on the right track.

The first topic I want to cover today is a question that I’m asked relatively frequently. It’s something that I’ve just written down in my book that I’m working on. I’m working on a book about building seven-figure SaaS companies, mostly bootstrapping. This question of, what should I be focused on versus which things should I delegate, which roles, which responsibilities, and which tasks. The framework that I have around this is certainty versus uncertainty.

There are so many tasks in a startup that you’re relatively certain what the outcome will be. Email support is a certainty. You’re going to get some emails, and it’s a certainty you’re going to have a response to those emails, right? There’s not so much creative work or big levels of, is this going to happen? Is this going to work? I need to try a bunch of different things before I figure out what works.

In the early days, the first month to three months, yes, there are new questions. You don’t know what’s coming, but eventually, you get your canned responses. You’ve seen 80% of the tickets that are going to come through and you figure out ways to put stuff into KB and to make support a repeatable process. This is similar even with software development without actually writing the code. 

Unless you’re building something incredibly novel, incredibly difficult. AI, machine learning, or something maybe with VR—unless you’re doing that, the odds are that once you know which features to build, getting that feature built is pretty predictable. You know that you can build the page to have the checkbox with the setting that says whether people should send email or receive email. It’s a checkbox. You can build this.

You may be off on that time estimate, is it going to take a day or is it going to take three days? That’s a little uncertain, but getting that task done is pretty predictable. Thus, I would call it a certainty versus which features should we build in order to get closer to product-market fit or in order to satisfy more customers? Which features should we build next? How should we prioritize these? It’s uncertain, it’s kind of foggy. You do not have absolute data. You don’t know exactly which is going to work. Frankly, you’re probably going to have to make some mistakes along the way. You’re going to build some features that maybe you shouldn’t have built. 

We did that. I’ve done that before. You build them and then you think a year or two later, no one ever uses that. Why did I build it? But you need to get enough successes when you’re doing that, that you keep pushing the product forward.

Another big area of uncertainty is in marketing. When you don’t have any marketing approaches that are working and sending constant consistent leads to your site, it’s going to be some uncertainty of, we don’t have any data on which approaches we should try. The first thing I would do is go to my rules of thumb like what are the five main B2B SaaS marketing approaches. I will reveal those in my upcoming book.

I would pick one of those, I would dive deep on it, and you try it. You go months, you go all in, and you spend the time. It may work and it may not. The uncertainty there is kind of unnerving. But being a founder is making hard decisions with incomplete information. As you think about these two paradigms of certain versus uncertain, realistically, as the founder, you should be diving into the things that are hard and that are uncertain because you’re the best equipped to figure those out. 

There are some exceptions I’ll say. Could I just hire a marketing genius unicorn who can come in and take the uncertainty, try a bunch of marketing approaches, and figure them out? Is that possible? Yes. Is it likely? No, you are going to have to find the 1 in 10,000 marketers, someone in Asia […] or […]. There are a few other folks I’ve worked with who are that good that they can take the strategy, try a bunch of things, figure it out, and then make them more certain.

Once you’re six months into running ads and they’re working, once you’re six months into SEO and content and that’s generating leads and it’s growing your business, that becomes more of a certainty. At that point, that’s when you can start to think about handing it off. You hire someone, you bring somebody in who’s really good at that particular thing. You bring in an amazing content marketer and amazing SEO writer.

This is now a proven aspect of your business, just like your product is. Deciding what to build next is really, really hard before product-market fit because you’re flailing all over the place. You don’t really know. You see, I don’t have 80% of the features that I need. Flash forward to three years, you have product-market fit. You’re doing $2–3 million a year. It becomes a lot easier. From experience, it becomes a lot easier to look ahead almost a year and say, this is probably what we need over the next year. 

There’s always going to be stuff that makes its way in that you didn’t hear about. By that time, you’ve heard so many suggestions. You’ve heard the gamut of what someone could possibly want in your product because there’s maturity and it’s become a more certain piece of your business. In fact, that’s at the point where we hired our first product manager, the first time that the two co-founders of Drip did not make every single product decision about what should be built.

You know a lot about how it should be built—although we had designers helping us with that—the first time was when we were doing a few million dollars. We could have possibly done it a little earlier. I’m going to be honest, there was a lot more uncertainty before that point. 

The lesson I want you to take away as a founder or an aspiring founder is that the areas of uncertainty are going to be the ones that you don’t want to lean into. Your comfort zone is in areas of certainty because you know that you can do them. You can write the code and ship the code to make the app.

The uncertain piece is, do you know what to build to make the app viable, to make it into not just a hobby but a business? The answer is probably not. You need to lean into the uncertain. The riskier aspects of your business at the start because those are the ones that make you uncomfortable. Those are the ones that are going to help you. You’ll actually grow the business. You can use this as a guiding principle of the moment. I have enough money to hire someone, whether it’s a part time contractor, whether it’s a full time person. I would always be looking to essentially offload the areas of certainty. 

Customer support is an early one. Software development, it is more of a certainty. I know there’s craft to it. I’m a developer myself. I really used to be a developer, but I know the craft that goes around development, and that as a founder, you care more than anyone else. That’s true, but honestly, if you want to grow this business and you want to build something that people want, get there fast, and be an ambitious startup founder, you are likely leaving growth on the table by hanging out in areas of certainty for too long.

My second topic is about as a founder, giving everything to your business without taking the proper breaks or the rest to recharge. It is a recipe for burnout. This is also a recipe for not operating at a high level, not operating at your peak productivity. For this, I want to use an analogy from a tabletop role-playing game. It’s called Dungeon Crawl Classics. If you’ve heard of Dungeons and Dragons, this is a game similar to that.

You roll the dice. It randomly decides if you hit or you don’t a creature and how much hit points you do. There’s solving the puzzles. There’s exploration. It’s an interactive game. It’s a fun game. You can play in person or some folks play it online. The thing that I like about Dungeon Crawl Classics, which I’ve never actually played. 

I have the rulebook and I listen to some podcasts of people who talk about it, but one of my favorite elements of DCC is—it’s called Dungeon Crawl classics—this concept of spell burn. It’s this phrase they invented to define this mechanic of the game. What spell burn is, if you are a Magic user or a mage, follow me on this even if you don’t like role playing games, just follow me. I’ll get back to startups. 

Spell burn is if you are a spellcaster, you can burn some of your stats to add to your die roll. When you go to hit or cast a spell to roll back your stats. You have things like strength and agility and I forgot what they’re called in DCC. The DND words are strength, dexterity, wisdom, intelligence, constitution, and charisma. Each of those defines something. 

Strength is how strong you are. Dexterity is how agile you move around. Again, DCC has different names for them. I think it’s agility instead of dexterity, but with Dungeon Crawl Classics, you can burn points of strength, points of agility. I think maybe charisma is the third one. When I say burn, basically, these attributes range from 3 to 18. You can say, I’m going to take three of my strength points.

Let’s say, I have 15 strength points. I’m going to take three of my strength points, I’m going to add them to this die roll, and then your strength temporarily drops down to 12. That weakens you. It makes your attacks work less. It literally is taxing your physical form, but it’s like you’re pushing it into the spell you’re casting. Then you know you roll your die and if you hit it without the added three, then you made a bad choice.

If that three is the difference between hitting and missing, you only use this when you really, really need it. It’s going to be a total party kill or you’re going to get crushed. The concept here is that you are literally sacrificing part of your physical form in order to be successful at this action. I’m hoping you can see the obvious path to what I’m about to say about startup founders.

How many founders do we know, myself included, who burned parts of ourselves mentally, physically, and emotionally, to be more successful at an action or to be more successful at our company? How many of us sacrifice sleep, sacrifice exercise, sacrifice personal relationships, sacrifice alone time for emotional recharging? Startup burn, maybe that’s the term for it. I think of it as spell burn. It is taking aspects of yourself and grinding them down and giving it to this other entity so that it can succeed.

In the short term, it will work. In DCC, if you spell burn your points down too low, you eventually can die. You can sacrifice your life to die to cast this last spell. The way you recharge is you take rests. I think healing potions might also work. I actually don’t know. You can tell I like the concept but haven’t actually played the game. But long rests is what starts to recharge you. I think you recharge one point per day or whatever to give you an idea of how long if you sacrifice three, five, or eight points, it can take a long time to regain these back.

It’s the same with startups. It’s the same with your company. When you give all of your emotional energy and all of your time—your 40-, your 50-, maybe your 60-hour weeks if you’re doing that. You empty your bucket for your company or your product and you don’t have any left for the rest of your life, you have to eventually take a rest. You have to step away in a way that recharges those batteries.

Personally, we ran a tiny seed retreat about 10 days ago before I’m recording this and then we had MicroConf right after it. I always know for at least the first two or three days after a MicroConf, I’m going to get almost no work done. I’m going to barely be able to talk to any other human, my wife and children included. I basically strapped on a VR headset for two or three hours. I played a bunch of games. I read about tabletop RPGs. I listen to podcasts that have nothing to do with business.

I watch some TV shows. I don’t really watch TV but I needed to do something that I wasn’t thinking about, interacting with, or diving into the business because I had spell burned myself into a place of exhaustion, which is what happens and it’s okay. I know that going into it. In fact, I’ve talked to several people on my team, Producer Xander and others. Basically, it’s the same thing. We all felt that way because you put so much into it.

The lesson I want to say is, look, it’s okay to do that but know that you have to take this in seasons, and you need to recharge quite frequently, probably more frequently than you think you do. While you will have seasons of maybe working long hours and being really emotionally intense about it. If you do that for months or years, it will absolutely grind you down. It will lead you to burnout, it will lead you to unhappiness. It’s just not a long term sustainable approach. Anytime I can talk about tabletop RPGs and relate them to startups, I consider that a win.

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My next topic is around management. More specifically, it’s a question I received from a founder that was saying, when should I hire my first manager? As a startup founder, should your third hire be someone who manages other people? That was kind of the question we were getting at. To answer that question, I had to frame it with this framework that I have around management. I think there are two components to management, there’s supervising and there’s leading. They’re two very different things. 

The supervision is more of a mechanical approach. It’s taking care of vacation requests, it’s being a liaison between them and HR, it’s doing monthly or weekly one on ones, it’s annual reviews, it’s worrying about pay in terms of their salary, and that they’re well compensated, that they’re happy. It’s the mechanics of interacting with that person on your team versus leadership or leading, which is the way I define it is guiding them, mentoring them, and overseeing their actual on-the-job actions.

I want to give an example to illuminate this. If you’re a developer, it’s often that you’ll have a tech lead who is not your manager. That tech lead is probably doing code reviews for you, mentoring you in terms of software development, making sure the code base is great, guiding architecture. There are all types of things happening, but the tech lead is often not your supervisor or your manager. That often is a director of engineering or a manager of engineering.

In the case of Drip where I was the co-founder, I supervise the entire team. Everyone reported to me. That was because we never got more than 10 people. Frankly, you shouldn’t have more than six direct reports, let me just put it that way. But that’s what made the most sense. I had the most management experience. I was handling all the day-to-day operation and mechanical supervision of everyone.

The leadership—the technical leadership—specifically, was much, much, much more on Derek’s plate. He knew Ruby, I didn’t. He and I would architect things. We would talk about things. We would guide it technically, but he was the tech lead. That was his role, right? All the engineers look to him for technical guidance. Then they look to me for, can I take time off, what’s going on with my health insurance?

Similarly, with customer success, once we had two customer successes, Anna became the head of customer success. She was the technical lead of our other customer success person, but everybody still reported to me. So supervising versus leading. That’s how I want you to think about it. You could have a 10-person company and you could be the supervisor or the manager of 10 people, they’re all reporting to you.

I think at that point, you can’t possibly be a subject matter expert in all the areas and you have to have someone leading at least a couple of those areas. Usually, it’s product/engineering, customer success. I can imagine there being a sales leader. If we were a heavy sales organization, that would have been the case. I didn’t have the skill set to do that.

The reason I make this differentiation is I think the technical leadership or the customer success leadership, that can happen really early. You can have someone who is a good individual contributor be a good leader, but being a supervisor and providing that, I’d say it’s more advanced or more in-depth like feedback and giving critical feedback about performance, that often takes a lot of work. It takes some practice or having worked with a manager that you respect who’s doing a really good job.

I think really early on in your company, delegating leadership of development, leadership of sales, or leadership of customer success I think is an absolute win. I think by the time you’re at three or four people, maybe five, you should start thinking about that. If you have anyone who is a little more senior, delegating that without delegating the supervision, if they don’t have the experience. 

Then when you get to the point where you directly have about six direct reports, not including any founders, you should really start thinking about, okay, am I able to promote any of the leads that I have into a full-blown manager where they’re both supervising and leading? I hope that’s helpful for you in thinking through the concept of when should I hire managers for my company. 

For the fourth and final topic of today, I want to talk about iterating. I want to talk about how sometimes things take a lot of iterations, sometimes they don’t, and sometimes you nail them from the start.

For this one, I’m going to have another analogy and not tabletop role playing games, but is another one of my favorite topics, The Beatles. So my youngest son and I listen to all the alternate takes of Strawberry Fields Forever. I’m sure you’ve heard this song. The cool thing about The Beatles is they have so many great songs but then they also have all this outtake footage where there are literally at least 26 takes of Strawberry Fields Forever that were recorded. Then there are a bunch more that they were just doing in practice and not recording.

This is an addition to the demo version that John Lennon recorded at his house. The crazy thing about it is they’ve released takes 1, 4, 7, and 26. They’re on Spotify. You can find them on YouTube. Then there’s the final version. Then there’s a demo version. So there are literally six or seven versions of the song.

My son took to this one version that is very different from the others, and of course, these aren’t just takes. When you think of a musician doing 20 takes of something you think, oh, they hit the wrong notes. They were offbeat. But this is The Beatles. They’re genius musicians and almost every take is a full take-through that could have been pressed to vinyl.

That’s not what they’re doing. It’s not that they’re taking it because they screwed up. They’re adapting the song and they’re changing the song over time. When you listen to take 1, it’s a very stripped down almost acoustic thing with kind of a keyboard behind it.

“Let me take you down ‘cause I’m going to strawberry fields. Nothing is real and nothing to get hung about. Strawberry fields forever.”

Then they take six or seven, they’re adding horns in.

“Let me take you down ‘cause I’m going to strawberry fields. Nothing is real and nothing to get hung about. Strawberry fields forever.”

Then there’s the take 26 that has cellos. It has backward drum beats playing in it, it’s way faster. It is just almost a completely different song. The melody and the words are still there but the feel of the song has evolved from John with his guitar into this, frankly, incredible work of art.

“Let me take you down ‘cause I’m going to strawberry fields. Nothing is real and nothing to get hung about. Strawberry fields forever.”

All that to say they didn’t do that with every song, but they were willing to put in the time and they were willing to follow their gut to get to a vision that they had in their head. You know John Lennon, Paul McCartney, or George Harrison that they had a vision in their head of what that song maybe should sound like, but they didn’t know exactly and they just had to work it and work it and work it and get there.

Then there were songs like Yesterday that Paul McCartney woke up and the melody was in his head and he thought that he had heard it somewhere else but he remembered it anyway. He’s playing the song with different lyrics. Originally, it was called scrambled eggs. Really bad words. Not like “yesterday, all my troubles seemed so far away” is a good song. But it was like “scrambled eggs, oh, how I love your legs.” I think that was the original lyrics.

It’s terrible but he’s playing this for people saying, have you ever heard this? Have you ever heard this? Because I think I’m ripping this off by accident because it was just in my head. That was it. He wrote the lyrics. My understanding is there are two takes, literally two takes, that’s it, of that song. Because the song was done. He knew it had hit the vision and he knew it was amazing. I think it’s my favorite Beatles song. I think it’s one of my favorite songs of all time, to be honest.

It is, I think, still the most covered song ever, that has the most cover versions of any song ever written by anyone is Yesterday. I think there’s a little testament to it’s probably a pretty good one. Here, on one hand, we have Strawberry Fields Forever, with all this iteration over days and days and days, getting not a full orchestra, but most of an orchestra involved and having all these versions, and then we have Yesterday that pops into a guy’s head that he does two takes of and then it’s done.

There are other examples of this, not just The Beatles. I’ve been to several Picasso museums. It’s funny, Picasso’s art is fine. It’s not like I’m enthralled with Picasso, but Picasso’s creative process is incredible. There’s a reason that I have a Picasso guitar tattooed on one of my arms because I’m enthralled with the fact that he would paint the same painting in different ways 20, 30, 40 times because he was iterating trying to figure out how am I going to get this to work? How does this fit together to where this finally lives up to my taste of what I want this to be.

That’s how he invented Cubism. You can google that, but it’s an entire branch of art. It’s a style of art that just didn’t exist. He learned the basics, he learned the fundamentals, and he painted paintings like everyone else. Then he just started iterating and iterating. You’ll see there’s one room—I believe it’s in Barcelona, the Picasso Museum in Barcelona—where there are 25–30 versions of the same painting with different colors from different perspectives, with different views, and it changes each time.

I’m so struck. I sat in that room for 10, 15 minutes and just stared at these works of art that any one of them is a work of art and could be hung in a museum, but they didn’t live up to his tastes. It wasn’t what he wanted. He knew he was not getting the results that he wanted so he kept iterating.

Similarly, Einstein spent how many years iterating and developing relativity, it did not hit him instantly. I think that’s a long way of saying that in startups, it’s the same thing. Sometimes you will start a marketing approach to content, say SEO. It kind of works from the start, but it doesn’t really. I think founders who aren’t long term successful, they throw their hands up and say, this doesn’t work. AdWords, Facebook ads, they just don’t work. But they do and they can.

They may not work in your space, that’s true, but did you think that maybe you didn’t iterate enough? Did you think the execution is off, that you need to play around with it more? Maybe you need to get better at Facebook ads, Google ads, content, SEO, maybe you need to give it more time. There’s a balance here. You don’t want to do something for a year and spend all that time and have it not work.

Also, I think, giving a marketing approach a month or giving a product three months to find the product-market fit is too short. There’s someplace in between where you need to see the progress along the way that as you iterate, there should be some progress made. You should be getting some traction with it slowly. You start to see that light at the end of the tunnel. You start to see take 26 on the horizon or painting number 30 where you think I’m getting there.

I’ve said before, so much of being a founder is managing your own psychology. Part of that is knowing yourself. If you’re the one who tends to just skip from one thing to the next and you don’t iterate, you don’t improve it, and you don’t put in the time to figure out these hard things, then you probably need to stick with things longer than feels rational, longer than you want to.

You need to get reinforcement from a mastermind group, from a co-founder, from someone else who has some insight in your business because oftentimes we have blind spots. We need a different perspective to help guide us or to help push us when we want to skip to the next thing. 

Conversely, if you’re the person who sits and grinds on something for nine months—I tried Facebook ads for nine months and they didn’t work—probably too long then. You probably should have got some outside counsel before. Maybe you should have considered hiring a consultant. Maybe you should have just bailed on it and moved on to content SEO.

There’s this balance of knowing yourself and knowing what your tendencies are. But realizing that even geniuses, even the best there have ever been—people like Einstein, Picasso, and The Beatles, these names are synonymous, they are used as examples of geniuses. Even these inventors, artists, and musicians had to iterate over and over and over on their works to get them to be successful, to get them to live up to their taste.

I think to a lot of us, this is where we put our creative juices. This is how we get that feeling of building something. This is our dopamine rush. For some people, it’s writing a song or painting and for others, it’s shipping a feature or it’s building a multimillion-dollar company that changes your life. I hope that thought of sometimes needing many iterations, sometimes, though in rare cases, that kind of thought process or mental framework is helpful to you this week on your entrepreneurial journey.

Speaking of showing up every week for 12 years, this is episode 600. I debated whether to even bring it up because I’m just not sure how important that number is. It shouldn’t be any different than 599 or 601. It happens to have a couple of zeros at the end but you show up every week to build something like this. When these 100-episode milestones hit, I always think I should do something different and special. I should bring on these guests and we should reflect on things we’ve done and how we’ve done it.

We have done that, right? Mike and I had our wives on for an episode. That was probably episode 200. I’ve done reflection episodes, look back episodes, we’ve had people send in audio clips, we’ve had all that all the stuff. I think that’s great. Maybe at 700, I’ll do that again. I think it’s a good reminder to think about sometimes just showing up every week and putting in your time, whether it’s this podcast or whether it’s showing up every day to ship that next feature, celebrate your milestones, and I’ll be celebrating privately.

I’ll probably hang out with my wife and kids tonight and raise a glass to episode 600. But as you build your product, as you build your business, as you build your company, remember to think in terms of years, not months. Sometimes just showing up every day or every week and putting in the work is what you need to do to get to where you want to go.

Thank you so much for joining me this week and whether it’s for the last six or last 600 episodes, it’s been my absolute pleasure to get on the microphone and be able to think about these things and talk about them, and hopefully, these are helpful to you this week or this month or this year as you build and grow company. Signing off from episode 600. We’ll be back in your ears again next Tuesday morning.