How To Take Care Of Yourself as a Founder

Hey, everybody. I thought this year would be a little easier. A little easier. If you look at most public company CEOs that had a challenging year last year, they didn't predict how tough this year would be, but they said it couldn't be worse because we're bouncing off bottoms. We're bouncing off the seat contractions, the app layoffs, the budget cuts. If you've cut 20% of your seats last year, there's no way you're going to keep cutting this year. And to some extent it's true. To some extent it is true. And. But somehow this is proving to be an even tougher year on many founders. We're off to a year where I have seen many leaders throwing the Towel, folks at 50 million, a hundred million, 150 million, 200 million in AR, I've seen several this week. Great leaders. I profoundly respect founders that are much better than me. Call it a day. Call it a day with nothing else lined up but catching up on Netflix and going for a run. And I get it. I get it. This stuff is hard. Maybe we forgot how hard it was in 2021 into 2022. We forgot. In the old days, being a founder was seen as insane and almost impossible. And then it became routine, and then it. And it seemed almost like a game. It's not a game. It's hard. So with that, I want to challenge you to not throw in the towel, to not give up, to not even quiet quit, to not start working 30 hours a week, to not blame the rest of the world. As a founder, it is a magical thing to take something to nothing. It is a magical thing to get from no customers to just 10 customers, 20 customers, a hundred. Even if it's not enough revenue, even if it doesn't seem like you'll ever have an exit, let alone an ipo, you've still done something magical. You've. You've taken some lines of code and some human beings and added value to this world. In software. It's special. And it's. When times aren't quite as tough, it's. It's even fun. And it's. It's certainly magical. So how do you take care of yourself as a founder? You've got to do it. And first of all, I worry about all the TikToks and stuff these days in the social media, telling you the way to take care of yourself as a founder is to work less hard. That's not true. The real answer, painfully, is to work harder. You've got to push through the tougher times. But that alone isn't enough. If all you do is work harder, if you work, if you truly work 80 hours a week, a hundred hours a week, you will burn yourself completely up. So it's work harder, but work smarter. And how do you do that? Okay, so let me give you five ideas on how to actually take care of yourself as a founder that will actually make a difference from the Saster post. Okay, the most important one of all, this one always works. It's worked for me again and again. It worked for me twice as a founder. It's working for me at Saster. Go hire one great vp, one great executive on your team. I can't tell you how game changing this is. In tougher times. Actually, in great times, hiring a great VP is nice. But sometimes there's so much momentum in the business, you don't even see an immediate lift. Sometimes when, when things are exploding. But boy, when times are tough or everything slows down, you can't get any features out, sales slows to a crawl. It doesn't feel like there's any leads or new customers. And marketing, all the churn goes up. Everything's tough. And one great VP can't take you from 10% growth to a hundred. I mean, sometimes, sometimes if the leads are there, it can happen, but in tougher times, but they can make an improvement. If you don't have a real VP of sales and everyone's down in the dumps and everyone, everyone's booking a hundred K a year and you bring a VP of sales in that truly believes that spends more time with the customers, that believes in not just both the problem and the solution that flies out there, that hangs out, you're going to close more. Not only going to close more, it will give the whole organization a boost. Anything VP of sales, marketing, product engineering, customer says one great VP not only gives the organization a boost, but it takes some of that off your shoulders. Those 80 hours a week, it's too much. And someone carrying the load, someone carrying more of the load for you. I find for founders is the number one way you can take care of yourself. It's much more valuable than a spa day or, or a cheat day or whatever. Get someone to take care of the load. And the way to do that is a great VP. So pick one. Pick one and just go hire 30 great folks for that role. And in fact, don't even worry about which one it is. If you want, go out to hire a VP of sales, which is usually the one we all go try to do. But you happen to find the most incredible head of marketing, the most incredible head of product or customer success, just hire her or him instead. Not only will they be accretive if they're great, which we've talked about in Sester, but they will take some of the load off your shoulders. So go hire one VP. If I had to just make 1.5 times, it would be that one. Okay, second one. The second one I do actually think we've gotten slightly better at. But take a vacation. And in fact take a vacation every year and every few years, take what I call a two plus two vacation. And in the old days, founders never took vacations. I actually find that folks take vacations now. It's just in the area of constant social media and even worse business social media. LinkedIn and Twitter, we never take a break. So if you can somehow take a vacation. What I used to do and then stop doing and then did again was solocation. Solocation. I know this sounds wacky, guys, but it really works. I would go. Go somewhere all by myself and get bored and get bored and not check email. I would check a little bit mobile. Okay? I mean, you can't. You can't avoid it these days. But I would only bring an iPad, not a laptop. And I would check out for just one week. One week. I did Palm Springs, I did Napa. I actually did Spain. When 0.9 had a founder event, I just went there and decompressed. I did four of these, and then I did Pacific beach in San Diego. And they were great. They were great. Now it's not enough. It doesn't change the course of your company, but that real vacation is much more powerful than a workcation. Okay? More importantly, most hunters don't get burned out the first year or even the second year. There's just too much going on. What you've got to do sometime around year four or five is do a two plus two and two. That means two real weeks off, two real weeks to go away. Because it's that second week when in Hawaii or wherever you want to go, the desert or the snow, when you. You. It really takes the second week until for the first time, you. Your body can physically decompress. And then when you get back, do two weeks of light work. Just, just don't. You don't have to make the plan that one month, okay? Reschedule the board meeting. Don't do as many meetings. Just participate and think. Give yourself time to think. A two plus two break. I don't find that this is Magical. But I do find it is the only thing that really refreshes you in terms of a break. Okay, the third one. The third one. Actually I've got six here. The third one, which is hard. But everything's hard, folks. Everything's hard. This one really works. Just don't forget it's never too late to find a late co founder. Sometimes I call these ex post facto co founders on Saster. But a lot of folks think you have to find a co founder on day zero. It's not true. It's not true. And in fact sometimes, especially if you're very technical and very smart, sometimes it's almost better to find a co founder later. Let's imagine you're a great technical co founder and you can hire a couple great engineers under you and you can get the whole product going and get to a few customers on your own. Maybe you don't need this great business co founder. Maybe you don't need her or him in the beginning. Maybe, maybe I always did better with a great co founder. But sometimes you're better off on your own than with a mediocre co founder or an almost great co founder. That's a mistake. That's a mistake. I have flown. I have flown when I had a great co founder but struggled when I had co founder conflict or co founder issues. Even if they were great. It's, it just, it just drags you down. So an alternative that's just under discussed is, you know, there's no rule that says you can't find a co founder on month six or month 12 or month 36 or month 60. And you can give them extra equity, you can give them some of your own equity. This is different than a great vp. This is like a super vp, someone that will truly own it with you together and you. And it's not too late. It is never too late. And whether they have the title or not, if you talk to some of the best CEOs out there, I've interviewed many at Saster and sometimes I ask this question, who on your team over the years did you hire that was kind of like a late co founder? Usually they leap to an answer. It was, it was Janine on my team. It was. It's often their CFO when they're later stage. Sometimes it's a COO in the early days, sometimes a VP of sales or VP of product, but they leap with that answer. Yeah, Iran wasn't quite my, my co founder but boy, he was close. He, he saved me in those late night conversations. And everything. So you can find a co founder that will not only carry the load for their functional area, but carry the load, cross functionally and pay up. It's worth it. It is. It is worth it for a late co founder. Okay. Fourth thing to do to take some of the load off is drop one thing. Just drop one thing. And this sounds silly or obvious, but it's a little more nuanced than that. This is a good exercise. A lot of folks will give you the advice. A lot of folks that are later stage CEOs at 100, 200 million IPO. We'll all talk about focus, focus. Do fewer things and that's great. When there's a thousand people on your team and 20 executives, sure. Then let, let Billy and Bob and Jane and, and and Jeanette do their thing. But what there's 10 of you or 15 or even 50. You can't just drop stuff or it just doesn't get done. It's not that simple. So, so you can't really like go from a million things to a few for real. But what you can do is this exercise of make a list of the 10 things the organization's actually doing that are a lot of work and that take a lot of mental bandwidth. Maybe 5. And drop 1. Just drop 1. Where there's an imbalance. It's so much team time, it's so many discussions, so much energy, but it's never gonna be. And this is key, 10% or more of your revenue. This is a classic old line of materiality. The SEC defines this as material as well for public companies. But it's a way to think about a lot of things as a founder. 10%. If something can't be 10% of your revenue someday, if it can't make 10% of your customers happier, if it can't impact 10% of something, no matter how wonderful it is, it's not enough. It's not big enough. It's not big enough. Or at least contribute to that 10%. So think about what's the one thing you're doing that's taking more than 10% of your 5 to 10% of your time that cannot have a 10% impact on the company. Just drop that one thing, move on for it, from it. Okay, five out of six. Five out of six. This one always works. And you can do it. Finally ship a game changing feature. I can't tell you as a founder how many times I've done that and recently is when the team is struggling, when they're down in the Dumpster and growth has slowed. Look, it's never quite this simple, but, but you know, I, when I, you know, the couple of things that you just got to get built to catch up or surpass the competition. When I interview founders to invest, it's always one of the first meeting questions I ask, especially the cto. But what are the top two feature gaps you have? And I listen, and I listen whether they're excited to go close them, why their feature gaps, what's happening? And founders that are struggling, like, ah, God, it's so hard. We just, we just can't ship the mobile app or the Outlook integration or the HubSpot. Integration's too complicated. There's a million excuses and I get it. And all this stuff is hard, but turn it around. When you ship a game changing feature, it really can change the game. Talk with your team and say, look, we don't have unlimited shots on goal here. We don't have unlimited arrows in our quiver, but help them pick. Let's force rank it. What's the one or two things we could do this year that would change the game, that would let us truly close more deals and somehow get your team to push it out faster and harder. Work with your cto, add a great engineer, do something and get a game changer out there. Game changers are fun. Game changers are great for the sales team because they can talk to prospects and customers and let them, hey, I know you're waiting for that SAP integration. I know you're waiting for the, for the Spanish localization. I know you were waiting for, for the API or this or that. We've got it, we've got it. And not just a rando fe, but a game changing feature. It inspires sales, which will inspire the rest of your team. It'll inspire customer success because they, they, they have something to talk about rather than just price increases. Again, not just a feature, but a game changing feature will rally the team. And by rallying the team, it will inflect the curve and it will take stress off your shoulders. It will take stress because you'll give them something that matters. You can even maybe take your vacation right after that. That game changing feature. Okay, the last point of six to take some of the load off, hang out with some founders at your stage or later. Now this one's a bit ironic because it's actually going to both add to your stress and reduce your stress. I find that founders that are too isolated struggle. They can't take care of themselves. And when you hang out with More folks at your stage or beyond. The folks behind you, the folks. If you're a 10 million error hanging out with a bunch of folks for one to two, it's nice, it's a good thing. Help them pay it back, Share your learnings. That can be a little cathartic. It has value, it can feel good, but it doesn't, it doesn't take the load off. Okay, it doesn't, it doesn't help you take care of yourself talking to founders below your stage. But cathartic dinner folks at your stage or a little bit later, it may not make you feel better, it may actually make you feel worse. Because you hear the other stories and the complaints and the issues. But when you hang out with peers or above, they tend to kick you in the arse the right way. And when you. When times are tougher and when we need to take care of ourselves, sometimes we just have trouble focusing. There's a hundred things broken in my startup. A hundred things aren't working. What do I focus on? What do I do? Even at Sasser, I mean Saster itself is reasonably successful, but there's so many things I want to do and fix. Sometimes I even can't focus my day or week. I struggle. But when I come back, spending time with folks better than me or at the same level as me, I focus. I focus on what matters. That's the key. When you hang out with other founders at your stage or later, instead of focusing on stuff that doesn't move the needle, you focus on what matters. And it doesn't give you the spa day feeling. In fact, you may feel some anxiety or ennui after that dinner or lunch or event. Come to sastranial, come to SAS Europa with founders at your stage or later. But it will inspire you to focus on what matters, kick you in the ass and help you do even better. That will help you really take care of yourself. Because at the end of the day, as founders, here's the thing, and we'll break on this point and this is what's different from founders, from almost any other role. Other roles you can always leave. There's always another startup, there's always another bus, and that's fine. Sometimes the best way, if you're not a founder, to reduce stress, is go somewhere else. Even if it's worse. Sometimes it just reduces stress and it's part of self care. But as you're a founder forever, whether you stay or go, whether you change your roles, whether you move to the board, you're the founder forever. You'll always be the founder. So simply checking out doesn't really reduce stress. What, what, what does reduce stress is leveling up the quality of the company, leveling up the quality of the product, leveling up the quality of the team, dropping things that don't matter, getting, making more progress on the journey. What wears us down as founders is when we feel like we're no longer making progress on the journey. That's the only ultimate way. Take your days off, take your two plus two vacations, go running, get healthier, get fitter, do all those things, take care of life at home, spend more time with family, friends. It's all good. But it's not enough for founders. It may be enough for other founders, it's not enough for founders. For founders you've got to improve at work to be happier and to be less stressed. And these are my best 66 ideas on just how to do it.