Tzakhi (00:00.34)
Hi, Charlie. Thank you for coming. We're at Meetup Capital startup podcast with Charlie Lass. Very exciting guest to have. You're the founder of Humble .Inc, which is a new platform for startups, people building businesses around the world. And you've been a founder all your life. You've exited three companies already. You've written...
Charlie (00:01.326)
Hey, thanks for having me.
Charlie (00:25.326)
Yes, sadly.
Tzakhi (00:29.652)
You've written a book and you're writing a new book about entrepreneurship right now as we speak or when we get off the call. And I'm very happy to have you with us.
Charlie (00:40.174)
Thank you very much indeed and a good morning from the US. Thanks for having me.
Tzakhi (00:46.356)
Yeah. Thanks for coming in so early. So yeah, we're going to talk about founder well -being, a thing that, a topic that I know you care a lot about. I also care a lot about, and I think every founder at least secretly cares a lot about because it's tough and managing your own mental well -being is something that you're doing all the time, whether you're thinking about it or not.
Charlie (01:14.254)
Yeah, there's, um, this is a topic that's really, really important to me. And we, as, as founders, um, it can be a very lonely journey and the conversation is changing, but I mean, pre pandemic, I can't tell you how many founders who in private were really struggling. And then as soon as you, and you know, you, you meet someone else on your level or the similar level of experience and they then go, this, this is really, really difficult. And I'm.
not okay, but it takes like a long, close relationship or a private conversation. Now we are seeing people say this is difficult and, you know, I don't know what to do about it. A really prominent example, February 24, Nvidia having dominated the last year, 250 % up in a year, the founder said in an interview in November that he wouldn't do it again. If he had the choice,
of 30 years at the company and all the success he's had. He said that the vulnerability and the journey he went on was too difficult. And in hindsight, he wouldn't repeat the process. And coming from someone with that much success is pretty telling as to how difficult this journey can be.
Tzakhi (02:34.324)
Yeah. Yeah. Yeah. And I think, and I think people are more aware and I think it's also become has become in a good way, a trend to start thinking about your own wellbeing. And lots of founders are like into working out, keeping a schedule, meditating. I do all those things, of course, or maybe not, of course, I do all those things. And I think it's really important, but I think it's only part of the story.
Charlie (03:02.382)
Yeah. I mean, I, yes, everyone, everyone does. Everyone wants to, um, I know I heard, I heard someone say the other day, um, my routine is, you know, wake up at five, meditate for however long, eat a hearty breakfast, play with my kids, kiss my wife, goodbye and all this other stuff. And he said that probably happens once every six months. Like I've got these grand plans of how I have this perfect routine.
And even, you know, look at Tim Ferriss or Matt Gray or whoever, who are the strongest proponents of this kind of look after yourself first, pay yourself first, treat yourself first. It's a great idea, but the reality is that life gets in the way all the time. And so people, it's very easy to beat yourself up. I didn't do that. I'm a failure. I look at this other person, they've got their routine down to the 20 minutes. And sure, lots of people are able to do that. But
doing it consistently, not being able to do it consistently doesn't mean that there's anything wrong or you're not trying hard enough. And it brings me to a point where someone shared with me the day rule. If you've got a plan for a routine and you miss a day, fine, whatever, stuff gets in the way, try not to make it two days. And if you stick to the two day rule, then over the course of a month, which is what really matters a month and a year, you'll find that you have got a much, much more...
rigid cadence than you think before. But yeah, the two day rule is a little bit of advice that I learned and I think it's really good.
Tzakhi (04:35.892)
Yeah, I have something similar that I do for myself, which is the schedule is to work out every day, knowing that the actual number is five days a week. So I don't plan to break, but I just know that it just happens on its own sometimes. Like you had a very late night or you're traveling or whatever. And then rather than.
beating yourself up or trying to wake up after three hours of sleep or something to do the workout. It's okay. This is the day off. But generally it's every day. So that way you can skip a day. Yeah. Yeah.
Charlie (05:09.966)
Yeah, this is the day off. Let's hit the ice cream.
Tzakhi (05:18.164)
Yeah, I think a lot of it is also about kind of thinking of what is the founder's role and how the founders view themselves. And in the culture of the US and of Israel, the founders often is kind of Superman that does everything, understands the technology, knows how to talk to the investors, create the vision.
If there are a few founders, then they split this kind of Superman role amongst themselves. But often there's one that's like supposed to be the leader and really holding everything together and knows how to recruit and knows how to manage and knows how to, you know, be the face of the company and so many things put together that it's, I think it's just a lot for a lot of people.
Charlie (06:08.334)
It is a lot. It is a lot and trying to be Superman is impossible. And you end up, you've got to remember that founders are, they go from boardrooms to bathrooms. Like if you're running the company, you're changing the light bulbs and the toilet paper in your staff bathroom and you're doing with investor meetings. So you're doing absolutely everything. And the danger of trying to do everything brilliantly is that you're not doing nothing well at all.
And you've got to acknowledge that there are some things that you just cannot be perfect at. And that's the starting point of a lot of stress and the road to burnout, founders, is you're looking at other people's showreel and relating it to your backstage. And you look at other people and go, oh, they did that thing amazingly, and they did that thing amazingly. And you get the amazing versions of every single person you meet, and you expect yourself to live up to those standards. It's not actually possible.
Um, so taking it, the other thing to remember is that the journey that you're on isn't the same this month as it will be next or certainly not next to this time next year. So you don't need to do everything brilliantly all the time. Every year, every day, because some things, you know, you won't always be, well, I say you won't always be fundraising. You probably will be always be fundraising actually, but the, you know, the, the business will grow. Cadence will change.
and you don't have to worry about solving every single problem right then and there.
Charlie (07:49.71)
And I think that the conversation around burnout is increasing, which is brilliant. And entrepreneurs work in weird ways. We don't always have a nine to five structure. You may work, you know, one day you might find yourself really in the groove with something and you work until midnight and you take the next morning off. But, you know, let's say you're walking around the park or you take yourself for lunch or something and someone sees you like, hang on, you're just...
Tzakhi (07:50.9)
So what is... Sorry.
Charlie (08:19.342)
chilling out on a Monday morning, having lunch and you're not taking this very seriously. Like, actually, mate, I was up till three in the morning working on this pitch deck and now I'm taking a break. Like, you can't judge the process. In fact, it doesn't matter what other people think, it matters what you think. And you're the only one that knows whether you're giving it the right amount of, I don't want to say 100 % because 100 % is impossible. There's actually a lot of studies that suggest that 85 % of your effort is one of the most efficient zones to be in because you're not.
you're not going to burn out, you'll be able to go further. Yeah, recognizing that entrepreneurs live and work in different ways is really important. We are also much more susceptible to mental health challenges, anxiety, depression, suicide, substance abuse, bipolar, ADHD, like, pick. And the question I rattle around in my mind is, are we drawn to that because we had
the likelihood of getting, of developing those disorders or do we have them and then seek out this career? I don't know. But the point being that it's very common to see entrepreneurs who aren't able to work in quote normal ways. And so being around an entrepreneur, seeing them go through the stresses and struggles that are all encompassing sometimes. This isn't
It is a career, but it's not just a job. It's something that you, every waking moment, you are likely thinking about your startup. And that really takes its toll. If you don't make an effort to step away from that, you know, it can be destructive. And seeing entrepreneurs that you care about operate and try to look after themselves in ways, take a break, that you should actually be encouraged, not judged.
Tzakhi (09:58.164)
Yeah. Yeah. What do you think is a way?
Tzakhi (10:17.812)
Yeah, absolutely. I want to kind of tell you about the there's a I spoke about this with another friend of mine, but not so long ago. There's a completely different model of entrepreneurship that I've seen in my work in India. I was advising Israeli companies going into India and I have a lot of experience, a lot of work done there. And there, the model is quite different. The entrepreneur is not called the entrepreneur.
I mean, they know the word of course, but the word they use is the promoter. So there's a person that is promoting an idea or a vision and they're usually not the CEO. It's a separated entity. Whereas the usual model in the West is the CEO is also the visionary and the person that has the vision is pushing the company forward is also the one, like you said, that ends up.
doing the most mundane things, just keeping it all together.
Charlie (11:20.174)
I really like that. I really like that.
Tzakhi (11:27.476)
Yeah, I think it takes some.
Charlie (11:27.662)
I'm going to use that example.
Tzakhi (11:34.356)
Yeah, it takes a real ability to delegate and to let go of things from a very early part of the journey. And I think that's very hard to do. That's like a very big challenge to be able to kind of send things off right from the start and not be the CEO of what you're building.
Charlie (11:56.398)
Really interesting.
Yeah, and I can see that makes a lot of sense. And the equivalent might be a COO, but it should be there around. I've often thought that... So I don't like the founder CEO title that we always sort of inherit. I think that in the early stages, C -suite titles are pretty pointless. You're taking a bit of the few of the tasks. I'll do this, you do that. Off we go. Otherwise you end up in a...
sort of founder dilemma of nominative determinism. When you call something that thing, it becomes that thing. So if you've got one of your early team is good with numbers, he suddenly becomes the CFO. And then two years down the line, like he's not qualified to do this, but he's the CFO. And now you've got to undo that. And it can very, very quickly cause a hell of a lot of problems with early founder teams. And founder infighting is, is just,
a major, major cause of startups failing to the point where I've seen one of the companies that I have mentored in the U .S. was a coaching platform for founders paid for by investors. So if you've gone through a VC round with these guys, they will basically pay for couples therapy for the founders. Because it is a hugely valuable investment to stop these guys from falling out. We'll keep the company going.
Tzakhi (13:28.308)
Yeah, and also maybe make some better leaders along the way.
Charlie (13:33.678)
You know, and founding a business with, this is another thing that just blows my mind. You know, people will say, Oh, I need a co -founder. I'm going to go and look for it. I'm going find a co -founder on Y Combinator's meetup board. Like you, you're looking for a marriage, like straight up marriage on a meetup board. That's nuts. You're going to be working with this person, hopefully in lockstep for seven and eight years, maybe longer. And you're going to meet them on a messaging board.
Tzakhi (13:34.002)
Yep.
Charlie (14:03.662)
Like maybe, but you know, the co -founder issue, I've had issues with co -founders in the past and I've known them for 17 years before. It's not, you never know what's gonna work out, but assuming that you need one and going finding, especially with technical. So I'm gonna go find a technical co -founder, because basically you're saying you don't know how to code. You're the business guy.
the visionary and you need someone to build a platform or something. Fine. But I think that's definitely changing with AI. That the usefulness of raw coding effort and power has been greatly diminished.
Tzakhi (14:46.644)
So do you think that now single founders are the better way to go for most companies? Obviously not for everyone, but for most companies.
Charlie (14:58.51)
All right.
The single founder thing doesn't mean you don't have a close team of people who are doing things that are. So with Humble, I have co -founders, but it's not a 50, you know, equitable equity split because it's not the same level of risk. But they're amazing, amazing people that I couldn't do what I'm doing without. So there is ownership, there is accountability, and there is equal drive. But.
we determined early on that it wasn't gonna be, I mean, everyone within the startup is replaceable, including the founder. In fact, especially the founder. So you do need that team, that phrase, it takes a village, it does. But going into this with an equal split, I've never seen work properly. Especially when you've got like four people, like, oh, I will take 25 % each. Like, how are you gonna get a vote done?
How are you going to decide on things? At some point, one person has to be accountable for this because you can't all be equally, two people cannot be equally responsible for a decision, especially when you're involving other people's money. I mean, you will know this from your fundraising journey. Investors need to be able to look one person in the eye and go, what happened? And that person needs to go, oh, okay, well, actually we got this wrong and did this and this went right. Fine. But it's not two people ever.
And it may be very closely to people, but it's never 50 -50.
Tzakhi (16:32.532)
Yeah, okay, so there's one person that's leading the company and that person has also most of the burden of the success or failure of the company on them.
Charlie (16:43.182)
Right. Yeah. Which is why I quite like your promoter structure. That's quite cool. But yeah, the CEO, which is why I think it's a very difficult title. Because if you're the CEO of Pfizer, and you get, you know, $100 million a year, like, cool, you're gonna have to take the heat for the everything that 10 ,000 people do. Like, that's your fault, eventually, because you get paid $100 million.
And also you get paid $100 million or probably more because it's everything is eventually your fault. But in a really small team, calling yourself the CEO, okay, sure, go for it. In the eyes of other investors, a sophisticated investor will know that if you're in the first couple of years of your growth of your business, the CEO title means nothing. It's demonstrating that who's got the vision, who's got the passion, who's showing up. And that's why vesting schedules are so important. Because at the beginning,
Everyone will be like, oh yeah, I'm gonna work 100 hours a day. We're gonna be billionaires by next week. Fantastic. And then suddenly someone has a family or someone gets hurt. You cannot maintain the same level of involvement, enthusiasm, energy and input across a long period of time. It's just not feasible. And so vesting schedules that say, all right, should we make it to year five, we'll all get this. That's the deal.
And when someone drops off and they inevitably do at year three, you're like, cool, you know what you get at year three, it's not year five. So everyone's happy, it's in paper at the beginning. And I think that being really open about the likelihood of success and the inevitability of founder stress and infighting, being aware of that from the start saves everyone a lot of trouble.
Tzakhi (18:41.972)
Okay, so I get that the idea of trying to build a structure that will kind of account for troubles ahead and also kind of take care of the inherent imbalance between founders that there's one that's kind of leading the way and there are others that might come in, might come out.
Let's go back to talking about how to handle the pressure that's on usually the lead founder, but maybe the leading team. So you said that you're not a big fan of sticking to a strong schedule and more about forgiving yourself, dealing with the surprising schedule that you might have, which is full of ups and downs and.
unexpected events, et cetera. What else do you think is kind of key to keeping it together?
Charlie (19:41.55)
Um.
Charlie (19:46.158)
Well, there's a number of things. Support structure. Actually, we have a podcast as well. And we have a regular feature from a guy called Ryan Casey Waller, who's actually my therapist. And he does a mental health moment for our listeners. We did a long interview with him a few weeks ago. And one of the pieces that he said was most valuable to him about when he was coming up in, and he's been a lawyer, he's been a priest, he's a
practicing therapists, like the guys, you know, had an amazing career. And one of the things that he learned early on was that if, when he was dealing with, with, um, addicts and he was mentoring, he was being mentored by someone and this guy, you know, went to Johns Hopkins and had all of the degrees. And he said, if I can get these people to have a group of people where they feel a community and half this problem is done. And he was just like, just a second.
half of the people you're working with could be improved if they just had some friends. He goes, yes, that's exactly what I'm saying. The reason being that we are herd animals. We need a tribe. And the psychological and physical damage from isolating yourself from the pack is extremely severe. And so as an entrepreneur, you're taking yourself away from one of the...
the most impactful ways in which we collaborate, which is around work. You're taking that piece, that community away completely. You're stepping out of the nine to five, all of that stuff that we're seeing where millions and millions and millions of people are fine familiar. You're stepping away from that. And then you're doing it on your own. So you're doing something different and you're doing it on your own and you're doing it all on your own shoulders. That is incredibly isolating. And your body and brain will...
will crave community. So this isn't about finding other founders at the same stage as you, because we've all got different metrics. And there isn't a ladder. You can't suddenly make partner or something as an entrepreneur. Like there isn't, I've got my MBA in entrepreneurship or something, not MBA, masters, whatever. The point is there isn't a check mark or a process that you go through.
Charlie (22:11.342)
Even being in a co -working space can be incredibly helpful. That you're seeing the same people doing the same thing. You're working on totally different things. Maybe you could collaborate, maybe just go for coffee, whatever, but you have to have a little bit of community. Not even just to vent problems to, but just to understand that you're not completely isolated locking yourself in a basement and building something because there will be other damage. You may build the best app in the world, but there'll be others. When you emerge into the light, you know, it's going to be a different place.
So yeah, the community is very, very important because of who we are as animals, not just for our own intellectual relaxation.
Tzakhi (22:50.484)
Yeah, I think one of the challenges around that is that it's much easier to do when things are kind of going well. But what happens is that when things don't go very well or take longer, then it becomes increasingly, it's like a downward spiral. It becomes for a lot of founders, and I can attest to that too, it becomes increasingly difficult to share, to talk to others, tell what's actually happening.
And that's where I think a lot of the isolation happens. So when things are going well, people like to share about it. And it's also part of what the bias that we talked about earlier in the conversation, you see others, you know, doing all kinds of things or sharing on social media, they're obviously sharing usually the best parts. And it feels like everyone's having a party and when things aren't going well, that kind of makes that isolation worse.
Charlie (23:39.402)
Right.
Charlie (23:46.158)
That's, and so the social media piece, you know, let's not delve into the toxicity of social media, because that's been done to death. And if people aren't at this point aware of it, then who knows. But actually that's one of the things we're trying to change at Humble is, if you go on LinkedIn, very few people have had a bad day ever, it seems, on LinkedIn. And if they have, then there was a life lesson and I'm so blessed to get through it. Like, okay, fine. You're not doing it in real time. What you're not doing on LinkedIn is going,
Holy, I'm having a really, really miserable day right now and I'm desperate for help and what I want to do is to post here, God damn it, I need a job, but I can't because I don't want to ruin my professional reputation or something. Like you just don't talk about the really bad bits whilst they're happening. You talk about the life lesson afterwards when things are okay, if they're okay. And at Humble, we're trying to, we have this thing called Startup Funerals where...
someone's business or their idea tanked and we'll all have a little ceremony and talk about, you know, put it to that, bury it. That failed, it's dead, move on. And there's an increase in meetups on Fridays, F up Fridays. And we taught you when you, you'd know about these, right? And you just talk about what went wrong. Well, this is, this sucks. I'm terrible at this or whatever it needs to be just to get it out.
Tzakhi (25:09.414)
Yeah, that's a great thing, the StartupFuture. That's pretty cool. Okay, what else have you built into Humble to support startup founder well -being?
Charlie (25:24.878)
Could you repeat that? You cut out a little bit.
Tzakhi (25:28.34)
Oh yeah, what else did you build into Humble for to support startup founder well -being?
Charlie (25:34.798)
Um, that's great. So we have, uh, one of our taglines is it's everything a startup needs and nothing else. We're trying to be one place where you can go and see the, no, I want to build a website. Okay. What do I need? Here's a, here's a review of Wix and Squarespace and WordPress. And here are the tools, like every product or tool you might need at your various, various journeys, uh, is, is available with reviews and.
people to talk to about how good they are, but it's all in one place. Then you've got a community of people without trolling, without toxicity, that are talking about the challenges that they're facing and content in any format covering pretty much any topic of entrepreneurship. But the difference being on Google, you get 30 minute results. YouTube, you get a lot of really great stuff. And then suddenly I'm watching a cat video or a World War II submarine video, whatever it's something.
You know, I'm distracted on LinkedIn, you get sold to and on TikTok, you get lied to. And so we're trying to solve for all four of those things where there is no endless scroll. So you don't just sit there forever. You want an answer. You find the answer from someone who's been vetted. That's the other thing is that each of the creators, we have checked that they do know what they're doing. It's not some 19 year old giving financial advice on TikTok. Like this person knows what they're doing. Um, and it, and it works. It really, it really seems to help.
Tzakhi (27:07.444)
Okay, Charlie, where should people find you? Should they go to Humble to subscribe? Where should people connect with you and with what you're doing?
Charlie (27:17.806)
So yeah, humble .inc is the website. Charlie Lass on LinkedIn or on humble. And yeah, that's great. And I have one parting thought.
Charlie (27:35.502)
which is about people, there is this very prevalent and very obvious framing that we all do, that we say, oh, when I get to here, oh, everything will be fine. All I gotta do is just raise some more cash and everything will be fine. Oh, when I exit for 10 million, everything will be fine. There isn't this Halcyon moment, it doesn't exist, where suddenly, because of one thing happening,
Tzakhi (27:36.052)
Yeah, please.
Charlie (28:05.07)
everything is suddenly rosy. That's an outcome based thinking where you're relying on external factors to provide you with validation and satisfaction. Focusing on the process is much, much easier. And the way to think about it is that entrepreneurs are athletes and artists. And if an artist sells their first painting, they've got 50,
other ones in a shed somewhere that they're working on. They're thinking about, ah, you know, that one, if I'd only done that bit differently, then, but someone's bought it. Someone liked it. Someone cared enough and then they've done it. But that doesn't mean that person is then stopping. If the person is running a 14, 400 meters and they get a great time, that doesn't mean they're going to stop. They're using that as a learning process to move on. So this thinking of things as moments in time as outcomes and saying, right, this exit will change everything.
Now, financially, that may be the case, but you're not gonna stop. The only person I can think of that's ever actually stopped and got away from it is MySpace Tom, who sold MySpace for 500 something million and has vanished. And well done him. But for the most part, that doesn't happen. But that doesn't mean you're not a successful entrepreneur. And people, you know, not all entrepreneurs have to be billionaires. You know, bringing in, you know.
$500 ,000 a year and looking after your family and not being stressed. Everyone would say yes to that because it provides you with the satisfaction of having built something on your own, solved a problem that you care about, and created some freedom for yourself. So I would just think of it in those terms that it doesn't have to be, you know, mega yachts and things. It can be satisfaction of having done things your own way and reached a point that you're proud of and that your family and loved ones are cared for.
Tzakhi (29:57.844)
Yeah, and keeping it together by remembering that it's a process and trying to find your well -being and your mental stability unrelated to the recent outcomes of what you've done. So that's a challenge for everyone, I think, in every walk of life, but definitely for entrepreneurs.
Tzakhi (30:25.236)
Charlie, this was a wonderful conversation. Thank you very much. We can do it again sometime. Really appreciate it. Humble .inc is where to subscribe to Humble and be part of your community that you're building. And we'll put that in the show notes, et cetera. If you're listening to this, subscribe to the Meet That Capital newsletter where we give every week a summary of...
Charlie (30:27.436)
Yeah, it's fun.
Charlie (30:31.662)
Please.
Tzakhi (30:53.908)
what we've learned from our weekly podcast and a lot of great content for founders as well. So thanks everyone. Bye for now.
Charlie (31:02.318)
Thank you very much.
