10 Years of Balsamiq: What I’ve Learned | Peldi Guilizzoni, Balsamiq | BoS USA 2018

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Peldi Guilizzoni, Founder/CEO, Balsamiq

In 2018, Balsamiq celebrated its 10th Birthday – an impressive achievement for any SaaS company. Founder Peldi has attended Business of Software every year since 2010, and has 5 BoS talks to his name. In his talks Peldi updates the BoS Community on the story of Balsamiq, and the ups and downs that come with running a growing, bootstrapped SaaS company. They are archetypal BoS talks: honest, full of insight, and give you a peek behind the curtain at the inner workings of a successful SaaS company.

In this talk from BoS USA 2018 he shared another honest update about his worries in Balsamiq’s milestone 10th year. On realizing he’s still too integral to the business, Peldi started the ‘Winter 2018 Injected Turbulence Project’ – delegated product design and engineering management, deleted Slack and witter from his phone, and stopped watching their internal wiki.

Video, Slides, & Transcript below

Like many BoS speakers, Peldi comes to the conference every year regardless of whether he’s on stage. He comes to be part of the community, to learn from others, and to hang out with his tribe. At BoS USA this year you’ll meet plenty of people like Peldi – incredible entrepreneurs keen to give advice and meet new people. Come and join your tribe at BoS USA this year.

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Transcript

Peldi Guilizzoni: Thank you. It never gets easier. I’m still nervous anyways. Thank you Mark for inviting me to speak again and share my latest batch of mistakes with you. So this was the title of the talk. We didn’t really know what to call this talk so we gave it this name. So we’ll try to find some other titles during the talk. So the first one is: “Ready for another group therapy session?”. If you’ve seen me speak before you know how it really it’s a bonding experience for everybody in this room. So I hope you’re ready. All right.

Previously on Desperate Housewives… this is where we left off. I spoke in London (I don’t know how many people saw that talk) but we talked about how we had this 25 person company and we were still flat and we had come up with this way to work collaboratively with no managers and we had projects and teams and people on projects and people have different roles within the teams – sort of like what Mikey was saying but much less organized of course and in a Balsamiq way. And so we were like hey it’s going to work. Yeah right. So that could be a title for this. OK. So let me remind you a little bit of this slide from 2012 which never really took off but I still I’m trying to push it some more. So the idea is that people think that learning is like a straight line the red line that you see there. Right. You learn you learn. You get better. But really I think that it’s more an up and down where you think you know what you’re doing and all of a sudden you realize how much there is to learn and you go down and you’re really sad and then you start learning again your confidence goes up again. And these are the times where I’ve spoken at BoS at different times and here we are right now. So. So that explains kind of my walk on music that’s kind of how I feel right now. So yeah. You know how sometimes here they have a stool or a desk you know and the lights go low. Yeah. So I asked Mark if we could get a therapy couch but it wasn’t available… But you know get ready. So let’s set the stage.

Balsamiq turned 10 this year. Yes. Which is amazing. Amazing. I never thought it would happen. I was always dreaming that it might happen. Since the beginning, my goal has been to build a long-lasting company and this double digit was kind of in my mind for the last nine years. Right. And we did it. And you kind of hit me because… now what? What do we do now? Coincidentally I was a few months ago doing some personal accounting and I added up all the dividends and the salary and the royalties that I got from Balsamiq over the 10 years. And I’ve made 10 million euros out of this little company. And I mean I’m just saying it’s weird. You know it was always a consequence not a motivator for me. But I have reached what people call financial independence which is such a foreign concept to me no one in my family or anybody really that I know has had this happen to them and so I really have no idea how to deal with this. Meanwhile my son who has to be in every slide that’s sort of a family rule he’s turning is turning 13 now and he only has five years of school before he goes to college somewhere. So we’re gonna be empty nesters in just five years. You know it’s gonna fly by and my wife and I are building a house in the countryside in Italy. With the idea that it’s gonna be our retirement home and we’re going to have rabbits and chickens and bees. So you know that’s gonna be ready next year. So you know this is how I think of being an entrepreneur. I’m sure many of you agree. It’s like Sisyphus pushing the boulder up the hill and then it rolls back and you’re answering one more e-mail one more e-mail and then 10 more e-mails arrive right. Now all of a sudden I’m like wait a minute I don’t actually need to work anymore. That’s weird but I like to work anyway. You’ll see.

So this talk could have been called “You Made It! Now What?”. And I can see a lot of you in the crowd. I get it I get it. This is totally awkward. Totally awkward. But I feel like if anyone is gonna make a fool of themselves and talk about these other things I’ll do that for you. So cause if you’re successful this might happen to you. I mean you’re dreaming of making it and then you’ll see. You know it’s not as easy. So we’ve lasted a decade as a company. Right now what do we do? I’ve been thinking how can we last another decade? Thinking that I’m not going to be here forever. There’s no way around it either you know take me out on a stretcher. I’m not going to be here forever. The market has given us permission to exist for 10 years. It’s likely that they’ll give us permission to last another 10 or another 20 to 30 and past my life if we do everything well, if we continue to execute well. And then I go back to this idea that I’ve struggled with since the beginning of whose company is it really? Because I wanted to start a company of one person. I wanted to be a micro-preneur, one person just me doing a little lifestyle business forever. No stress. Few customers, happy. You know that’s what I wanted. It was my dream. And then after a while I had to give up the dream because I was hiring too many customers so I had to. I had to hire employees. And then more and more and more and then now I think well it’s not just my company. All the employees we have 30 people that depend, their families depend on this company to exist. It’s their company. It gets worse – we have over half a million customers who want us to answer their email if they have a problem, who want us to build new features, who want us to keep going because we’re solving a problem for them – it is also their company. I feel a moral obligation to keep this thing going as long as we possibly can.

And so I realized that I think it’s still our revolves to much around me. It’s been 10 years. It should be better than this. And so the next question I ask myself is OK but really I had this feeling that it’s all too much about me. But what am I really needed for? What is it that if I don’t do it, things break. And so things are going well. Like I said after my last talk we were doing well we were firing on all cylinders. Very little drama. And so I thought sure time to inject some drama let’s inject some turbulence and so I started what I call the winter 2018 Injected Turbulence Experiment. I wrote this page for the team saying you know the fact that it’s too much around me it’s a limiting factor in the pursuit of our company’s mission. So here’s what I’m going to do. I delegated product design right, the product Balsamiq wireframes is my baby I’ve designed every single feature of it. I’m super proud of it. I think that it’s major reason for our success that it’s easy to use. People love it. I’m not going to do that anymore. And that was really hard for me to give up but I realized that I can’t do it. Someone else should do it better than me. Engineering Management another thing that I was good at and I’m able to keep a pace I do a lot of the things that Mikey mentioned without any numbers. So again very disorganized but I’m able to get good output out of all the engineers. Again I couldn’t do that anymore. I stopped watching the whole Wiki. I will get a notification anytime any employee touched any wiki page. Right. And so I knew what everybody was doing very I will get you know 50 or these or more a day – done, turned it off. Same for all the other notifications, people or trackers are kind of like our Jira/Trello. Get hub. I don’t know any commits anymore. I don’t know anything anymore. I decided to turn everything off. I even left a bunch of slack channels for different projects, different teams. Basically I closed my eyes. And I said why am I doing all these things at once? It’s pretty reckless to do it all at once. But I want to see how it feels. If I’m not if I’m not involved in the day to day operation of the company and also I want to know what we’ll break first. And I told the team keep calm and carry on and you know we can do it. You know the feminist poster I was trying to not doing a good job anyways. It should be a good test. Instead I’m going on vacation next week. I’m uninstalling Slack. I don’t want it. You know good luck. All at once. After ten years of doing all the work. You know so two weeks later I felt like this – I was eyes shut with my ears on the ground because I was terrified that something was gonna break and I wasn’t going to notice. Right. And so it was this very tense state of mind where my biggest fear was that we were gonna be maybe 10 percent slower, 10 percent lower quality, which are things that are hard to detect but we’ll kill the company in two years. Right. We can’t afford that. But how do I detect that? I went on a Twitter and Slack rehab. This was actually great. That hole that you see in the middle of the bottom that was Slack gone. I quit Facebook and I removed Twitter from the phone and I added New York Times and Wall Street Journal instead. And that was great because for 10 years maybe some of you can relate to this – How many times have you done this where you go to Twitter you search for your brand and you scroll and maybe you like… I’ve been doing this seriously four times a day for ten years. It’s a drug. It’s a total drug and so gone. Twitter has gone.

This was a good side effect. I never got an e-mail! Inbox zero, every day! Yes. And then I’m like wait a minute. People ask me how in a flat company, you’re remote you’re distributed. How do you know if people are working in their home. And I used to reply “You just know, you just know”. Actually you don’t know if you don’t watch all the Wikis and all the notifications. I have no idea if they’re even working at all. And that was weird, like Oh I see why people do OKRs or whatever, things that I hate because really I have no idea. Then there was this thing where you know we’re out and we’re not hierarchical we’re flat but really we’re not flat because I manage everybody. That’s kind of the idea. And 30 people is a lot. And you know what they say as well – at some point the CEO has to step back and take a strategic role so they have time to do visioning and look at the market and not be involved in the day to day of the operation. But if I’m the only manager, who’s flying the plane? If the pilot went back in and read a book during the flight you wouldn’t be so happy during the flight. And then I realized that there was a lot I needed to coach. I saw how people were working without my day to day input and I realized whoa we’re way behind. I even had to write a wiki page – how to do research on any topic – because I would see people getting stuck for weeks on a simple research because they just got lost in the Internet. You can find the infinite amount of things to read about any topic right. So how do you filter? How do you do it quickly. So I started doing sort of these things. And then I was like OK great what am I supposed to do? Why am I getting paid the most and I do nothing? That’s weird. So a couple of times I did fall off the wagon, I went back and I did a little coding and I did a little wireframing you know. But overall it was going OK.

One month later I got one new employee who said since you delegated engineering management to someone else everybody is so much happier. Great job. Thanks I guess… Great. Oh I’m glad. The not knowing what people are doing, you get used to that. I have no problem with that. I trust my employees they’re all bad asses. I don’t need to check on them that I spent too many too much time checking for no reason. I think that I did it because I’m interested in everything not because I wanted to make sure that people were working. I started changing my answer not fast enough from I can do this for you to I’ll help you get it done with coaching resources tools and time right. That’s the proper answer. It’s hard to do I still say come on let me just do it in five minutes. All right. But then we saw people started stepping up and really getting it and they’re like Oh crap. We have a problem. Let’s see how I can help fill that void. The idea of having a clear schedule which was one of the goals did not happen at all. I had a lot of meetings and most of my meetings ended up being the one on one quarterly meetings that we do which is where each employee looks at the last three months and makes a plan for themselves for the next three months and talks about the challenges and everything. So in the end all that I was left with was hearing people bitching and moaning about the problems that they have. Which was interesting… I still set all the salaries because we’re not even going to go there and the team is like No please don’t. Don’t spring this on us. We’ll deal with that later. And then we see that communication between teams starts to break down. You’re all nodding like of course you idiot. Of course he’s going to have but to me this was a surprise and then somebody in support was like I think we need a product manager because I don’t know what the dev team is going to prioritize and the dev team is like I don’t know what support people want what the customers want first. How do I prioritize the roadmap? Oh yeah I guess there is such a thing as product manager and I guess I was doing it without knowing. But overall nothing major broke. A month into it.

Two months into it something major broke. It was bad. It was a disaster. We deleted about twelve thousand projects for people on our web app. People who entrusted us with their data with their work of weeks and weeks… poof. I mean a company of ten years that makes a mistake so grave, you know I told my wife this could be it. We had a good run. But instead, we survived this event. But as the weeks went by. I started sort of monitoring my feelings because I had nothing to do. So that’s what you do. And so I started out in frustration because I would see things getting done not in the way that I would have done or not as fast or… But I also had to bite my tongue a lot because I really don’t know how to do this sort of coaching without interfering yet. Loneliness. You have to sort of be the rock for the whole company and I couldn’t vent to anyone because they were all part of the same experiment right. I didn’t want to influence the experiment that way. Plus I switched to working from home a couple of years ago and I always say that working from home is great for the first couple of years and then it kind of gets lonely. I do have an office mate but she’s kind of a slacker. She sleeps a lot on the job. Anyways and then I got bored and I’m like Oh crap. This is not a feeling I’ve ever associated with Balsamiq and I don’t like it. I cannot be bored with my mission in life. That is wrong. So I feel guilty. I feel guilty I was not enjoying myself anymore.

And it was a problem of my own doing and I was feeling like I was abandoning my baby and it was very I was very ambivalent about the whole thing the whole time, it was pretty tough. I started developing some curious side effects. I noticed that I started baking bread. Never in my life I would never thought of doing that! Every week I would make bread. I even took a bathroom in in the house and I painted it. I bought some from moving on and I printed a bunch of pictures and bought a bunch of frames. Who does that?! That’s insane. It’s insane. I bought a plant I bought and then I met another plant and then I fixed the plants and the terrace. I mean what’s happening to me. I decided I was going to rebrand. Sure. Whatever. I’m not a designer but I whenever I got time right. I went to Dublin for a conference and I was all alone and lonely and I would say oh maybe I’ll go to a museum. And I went to this museum and I went to this exhibition and I just started crying in front of a painting because it was so beautiful. Who is this person?! I can’t figure what is happening to me?! I started taking pictures of flowers… Something is weird right. You guys I mean clearly with the bread said there’s a creative volcano inside that needed some sort of output right. I even had several Pinterest boards. Several! Now I’m like I’m might becoming a woman?!

Then I even did the unthinkable. I thought maybe I could start a second company for just like five seconds and then stop it! You can’t think that can’t think that. I forgot to mention one thing. This is a Web site that doesn’t exist anymore. But it was my web site about how it was in the 90s. The number one Ultimate Frisbee related Web site in the world and I invented it. I made it I made it grow for 12 years of my life. Ultimate frisbee and this Web site was my life. I had sponsors I had an ad network I built myself everything that I learning college and my computer science I would throw it into here. It was huge because this was before Google right. It was huge I had interviews etc. and for a long time I thought this is it. This is my life’s calling. I’m going to do this for the rest of my life. For twelve years I remember my dad asking me about and I would say look it’s starting to make money this is my career already. And then my son was born and poof all interest in this vanished immediately. So I know that there’s this 12 year thing where nothing is forever even if you think you’re in the middle of it and you think this is my life’s calling. I’ve had this experience already and so then I’m like Oh crap. That was twelve years. This is Balsamiq. Does this mean that in two years I’m going to get bored of Balsamiq? More guilt, more shame because all I preach is I’m gonna be doing this forever. How can I have these feelings of not doing this right, my whole thing is no we’re not start ups we’re not going to sell ever. You know we are more like the butcher. So it was bad. It was bad.

Then some infighting started happening inside some teams, I sort of lost control. And then I realized that you know another drug that I have is every time I’m kind of sad I just get something done. You know I’ll make a web page, I’ll write a blog post, I’ll do something and it makes me feel better. My trusted source of endorphins to feel better and now I wasn’t letting myself working on anything day to day I shouldn’t do that. And so I didn’t even have this drug and then I had all these sleepless nights because I had all these meetings with the employees. And for them they were just venting their challenges their frustrations because we asked them to every quarter. But for me it was deep because it meant that something was broken. It meant there’s something I should fix. But now I wasn’t even allowed to fix it. And so I would lose sleep over it. They wouldn’t even notice that they said something minimal. But for me I was not sleeping. So in the end I burnt out totally burnt out. Well you know what that means you don’t want to get out of bed in the morning. I started taking two hour naps every day after lunch. Not good. Just like Jason Eckenroth who spoke in London says you know you feel tenderized and see there I am. That’s how I felt.

So after four months I said you guys let’s wrap this up. Great news, it was a success. I know the company needs. But actually… I mean every time I come and speak here I say I don’t know what I’m doing. It got worse. Now I know that I’m bad at what I’m doing. I wish I didn’t know what I was doing. I realized that I had spent too much time learning stuff on my own and not enough time disseminating what I had learned to the team. Which is kind of egotistical you know too much time doing stuff and not enough time letting other people do it or teaching other people how to do it. I ran into this video of the co-founder of Buffer and he says that the toughest feedback he has he’s ever received was when his other co-founder Joel who spoke here told him you know you’re really good at getting stuff done. But the fact that you get all this stuff done is actually hurting the team long term. You need to do less stuff. You need to do less of what you’re good at for the sake of the team. And no one wants to hear that, you think you’re killing it but actually you shouldn’t do what you’re good at sometimes, that kind of blew my mind. I realized that I had started this company to build a product, but really now someone else had to do that I had to focus on building a business. I had to be a business guy and it still sounds weird. And then I’m have to do the CEO thing. That’s not a very fun job. It’s kind of cliché you like saying that you’re a CEO but really it’s kind of a shitty job.

So that’s it. So I was like This is it. This is what I’m gonna say in Boston in a month this summer all summer I thought this is gonna be my talk, it’s going to be pathetic. I have no answers whatsoever. It’s gonna be great. People are gonna love it. Yeah I know. Imagine if that was right. So then I was like I can’t do this to people. This is such a downer. So let’s see let’s see if we can make it better. So some more time has passed and the team started getting the message. After I posted that wrap up page people totally saw through it they were like we got serious problems. And so this woman Natalie our CFO who’s been with us forever, she sort of took the initiative to organize the whole company except for me to go through what I was frustrated with and see if they could come up with a fix because they realized that I couldn’t help, I was too burned out I was kind of useless. And so they identified these tension points and you know not all teams feel unified or able to operate make decisions prioritize and so they gave me homework and then they made other projects to explore different things that we could do to solve these things. So that was great. One of the things that I realized was that what the company needed from me at this point was this roadmap document every six months. That sort of explains to everybody why each team has a right to exist and what they’re working on and how it all fits together. I never did this formally, but we did that. That’s easy. Then I also took back some creative projects. For instance we decided to refactor our Websites. We have 3/4 subdomains putting them all together into one thing. So this is kind of like a cross teams project that no one has the time to do but I had time to do and I enjoy doing this kind of stuff and so I took this on and this made me feel better because I was I felt productive again. Then thank God for GDPR! Nobody ever said that but I love it. Because it gave me something to do with a deadline and it was important and I had to talk to everybody on the team. What are we saving in this database. What why. Well and we did that and it was awesome. Yay GDPR! Then I bought an office. We know we’re all remote right. We have an office in Bologna but barely anybody goes to it. So why not buy a bigger office?! We’re 10 years old and I think that we deserve to have a place that we call home. Even if we don’t really go to it… I went to the Architect’s office and said you’ve got to build me the best office. No one’s going to go to it. That’s the future of architecture, trust me. She’s like okay whatever but this is a million details a million decisions and I just I’m doing it on my own. That’s what all does Pinterest boards were for with the architects and its super creative and I’m learning a lot and I love it. So I’m doing that. I stopped doing all those 1-on-1 quarterlies. They were not review quarterlies. We call them coaching personal professional development meetings and so some people do it with other people. As a coach you hire yourself a coach inside the company to help you through. And I said you guys I can’t do this anymore. How about we stop until the end of 2018 I do no more quarterlies. And so all of a sudden I wasn’t hearing all the challenges anymore. It’s not that they’ve gone away. I just don’t hear them. But right now that I can’t take them. So we’re taking a break like that. I joined a book club so that I can get out of the house and have a little intellectual stimulation outside the company. And that’s been fun. That’s my book club right there. Little fun fact – the woman there is a former Miss Italy so we even have a VIP in the book club. I picked up woodworking with hand tools only so that it’s nice and slow and I stay away from the computer longer. I built a workbench. It’s horrible but it’s mine and I made it with my hands. Finally instead of flipping bits for a living for ever you work with your hands. It’s super fun. And then I hired this sadist as a personal trainer. Every morning 8:00 I’m here. And he’s all happy and I’m finally taking care of my body and he’s all happy, I can’t even breathe. So I feel horrible while he’s there. I sweat for another couple hours after he leaves. Then I shower and then I feel good the rest of the day. And then I was like maybe I should start this Succession Planning whatever I don’t even want to say the word because I feel I still feel so bad about it but then I realize you know nothing is forever. I have to do this at some point maybe I’ll do it now and I’ll execute it when I’m 80 hopefully maybe I’ll do you know. But you got to be ready. You’ve got to be ready. It’s going to happen to all of you. Business owners. So what is the process for finding that new lily pad to jump to? How do I come up with a 10 year plan? Maybe we hire a product manager and someone to do HR to do the things that we have issues with? Maybe I hire or promote a new CEO and I become the product manager? What are my options. I don’t know. And then if I have to leave at some point if I want to leave. What are the options. You know ‘sell’ is very much a four letter word to me still. Selling means killing the culture means killing everything you’ve built. That’s how I feel right now. But who knows. To me a much better outcome would be that I leave the company, still own it, and the company does so much better without me, and I just get the cheques. Just like Mikey was talking about to me that’s the ultimate success because you’ve built something bigger than you that can outlast you. So there are options and then there’s this one. Okay. What I do when I leave what will be my identity. This thing has been my whole identity for 10 years and who knows how much longer. What happens next? And I always go back to Gail Goodman who came here and I don’t know if you remember, but during the Q&A she had this very moving moment where she was like – “How long can you be a ‘Former’”? you know her badge said former CEO because she had sold her company and she still hadn’t found her new identity and she was struggling. Struggling. Then I saw this tweet by Justin Jackson about how many friends are getting burnt out of digital work and they do permaculture, building, woodworking, photography, buying coffee shops all right. I’m like oh wait a minute maybe I’m not alone with these issues. Then I stumble into this – I watch a lot of YouTube the last few months, I had time. I stumbled on this on this TED talk about the longest study on happiness. So they studied hundreds of people for 70 years. Longest ever study and some started they were rich they were poor they were a mix of different people and when they started they all wanted money and fame. And then over time they checked who’s the happiest. And number one for sure reason for happiness is the number and quality of your relationships. Nothing else really matters. And I was like Huh okay. I have no friends right now. I got some catching up to do.

And so very very nervously I decided to reach out. So I sent this email to about a dozen people who had either sold their business or made it who were financially independent to find out more. And with the excuse of having a talk to write about I could have these conversations with people. And I was terrified about sending these e-mails because you’re the boss you’re supposed to have all the answers. This is being very vulnerable with people you look up to right where you all you want to say is like it’s going great it’s going great. Actually no. Right. So it was really scary thing to do. But I did and I got to speak to a bunch of people. Fantastic conversations very intimate too intimate to share unfortunately but I got some quotes from some people that I want to share with you.

So first I spoke with Neil Davidson who started this conference. Yes yes yes. And co-founder CEO of RedGate. And then after 15 years left and now does painting he’s an artist. Fantastic. He went to university for it and has a completely new career. And he had some nuggets of wisdom for me. This was actually a quote from another BoS talk. This is all very self-referential and I hope it’s okay. Clayton Christensen’s came up here and said sometimes in your life you have to execute, other times you have to explore. So give yourself that permission sometimes it’s just normal. If you burnout and hate your job you’re not doing the company any favors right. Crap you’re right you know. And then we were talking about my options. It was like maybe you need a COO not a new CEO, just keep the title just don’t do the job. And then if you want the title you can do whatever you want. These titles don’t mean much. There’s different kinds of CEOs. OK, interesting.

Then I spoke with Michael Prior co-founder of Fog Creek and CEO of Trello. He sold Trello last year I think to Atlassian, and still works there. And I asked why and he said still doing exactly what I enjoy doing. I’m scared that if I stop I’d feel unimportant and honestly I’d have nothing else to do. After a while, fishing will get pretty boring. So that’s interesting. So that’s why he’s still working there. He also pointed me to this white paper called Life After An Exit: How Entrepreneurs Transition To The Next Stage and I recommend it. It talks about you know a loss of identity and community and this is an interesting one how family friends and advisors actually change their relationship with you because they know you’re incredibly wealthy all of a sudden and it is awkward. I’ve seen that happen in my own experience.

Then I called Derek Sivers. He started CD Baby in the 90s and grew it and then sold it and then now is more of a TED talk speaker thinker philosopher guy. We had an hour long phone conversation because he loves the phone. That’s awesome I think. And here’s a few quotes – I could have a whole talk just about that conversation. But he says in hindsight I would have said set up more hierarchy. When I quit there were 85 employees mostly dumping their problems on me. Sounds familiar. When do you feel very frustrated don’t mistakenly think that are only two options. Some point he was so frustrated he said I’m either gonna shut it down or sell it. And that’s it. These are my only two options. And then his friends were like sleep on it for a few days and like oh maybe I could replicate it or I could change this process. I could do this so I could hire a grey hair manager and he did he tried for six months to do that – didn’t work out. But there are more options than you think. He was terrified that his tombstone was going to say Here lies Derek Sivers who made CB Baby and not much else right. And so we talked about how you can transition to a new a new career and making it out of sight as a side move for instance for him he’s becoming a speaker and it’s not like he’s starting from scratch. People like to listen to him speak because his resume he says he created and sold CD Baby and so you know you already have experience that you can draw on for your next career. It doesn’t have to be a restart. And then he talked about this book The 48 Laws Of Power. One interesting thing that he said is sure after you after you made it you can do whatever you want. And often the temptation is to do things that are easy. He said he’s tried to start some businesses but as soon as he hits some roadblock he will be like I don’t wanna deal with this again. Forget it. I’ll start something else right. And so here. One of the laws says if you attract attention it kind of brings the best out of you. So it’s not a great thing to want attention in general but it actually has the side effect of making you perform at a higher level. And that’s exactly why I’m here speaking to you right now. I don’t want to talk about any of this but it forced me to clarify my thoughts and reach out to these people.

Then I spoke with Jason Eckenroth. They tenderise guy. He loves this book. I don’t know if you know it called Traction: Get A Grip On Your Business. It’s for people who are kind of struggling who feel like they’ve lost control in their business. He says that he wish he had read this while he was still owning the company that he eventually sold. If you haven’t seen his talk it’s about these sort of post-tax it feelings and it’s from London 2017. I highly recommend it. And also he said something that stuck with me which is you only feel as wealthy as your cash flow. So if you know that more money is coming in in the future you feel great. The minute you sell now you’re like Oh crap this is all that I can use for the rest my life and my children. And so you become this sort of Scrooge because no more money is coming in. Right. So it’s not about how much you have it’s how much is coming in. That was interesting.

Then I spoke with Joel Spolsky, the other co-founder of this conference and founder of Fog Creek and sold it, founder of Stack Overflow. And then Trello et cetera et cetera. So you know he’s made it several times over in his career. And he challenged me right away said OK you’re struggling how about tell me why do you like bootstrapping. Why did you choose to bootstrap. Because like well that’s a nice challenge. And I was like Well I like to be my own boss not being able to make mistakes without too many consequences and learning a lot. And he said well do that just continue to do that somehow figure out how to do that. Oh interesting. And then again he said you have to have a real plan for what to do when you quit. You can’t just say I’m going to travel because while you’re really going to do is stay home and read Reddit all day. And then he said you know you’ve had a large impact already and you think the only way to top that is to go bigger. But it’s also by your personal journey it’s got to stay interesting. It’s got to keep evolving. It has to keep you feeling like you’ve lived every year of the few years we were given. That was nice it kind of gives you permission to. OK. You know it is about you too. It’s not just about the employees and the company. It has to fulfill you too. And then this I don’t have time but I’ll do it quickly. He gave me the algorithm for making friends in your 40s. Take a picture of this because I’m not going to talk about it but this is awesome. This is just what I needed so I’m going to start doing that quite a bit. And it’s worked for him. He’s made so many friends in the last few years with this simple algorithm.

Then I spoke with DHH of Basecamp. Right there everybody knows them. And they took a very Basecamp approach of saying it’s my company either whatever you want I’m going to make it whatever I want. I don’t care about anything else you know the design is malleable if you dare it to be. You can reconfigure the company vision scope and size. We’ve made it so that it’s basically Jason and I can get to do whatever we want, what we would love to do even if we weren’t working at base camp we carved our roles perfectly that way. OK.

Then I spoke with Natalie and Chris Nagele of WildBit. They spoke. She spoke here last year. They have a 17 year old software company. They do Postmark etc. And they had again some beautiful nuggets. Your employees don’t want you to be unhappy. You know they can see that you’re struggling. You’re not helping. You’re not helping. This was interesting. I asked what about hobbies? And they said well careful because if you have a hobby and you get so excited about the hobby then when you’re back at work you realize what a shitty job you have as a CEO. Is so much more fun to you know… Chris races race cars. There’s a lot of adrenaline there. Not a lot of adrenaline in answering emails you know. And then there were like It’s not fair either people get to switch jobs and careers if they want to why shouldn’t the entrepreneur why shouldn’t the boss have this freedom in life. Right. And then this is just these two books I started reading: Finish Big, really good really good stuff about these topics.

Then I spoke with Jason Cohen and you know him he started SmartBear. He sold that and then he started WPEngine. He came here last year I think. And he hired a CEO. Now he’s the CTO. He has no direct reports, kind of the Dharmesh model. He says it’s not true that the founder has to run the company forever. There’s only very few Steve Jobs and Jeff Bezos. These are the outliers. They’re not the normal. You don’t have to follow that same model. And he hired a CEO and ask him why not a COO. And he said because I wanted the best COO and those they don’t want to be COOs anymore. They want to be CEOs. And so to hire the best person you have to make them the CEO. And like I said these titles don’t really mean too much once you do them. And then this was a key concept of careful about running away from something versus running toward something and it’s similar to what Mikey was saying I guess. A lot of people quit or sell because they’re burnt out. They hate it. They can’t do this anymore, then you’re lost. instead if you line something up just like the other people were saying then you can get excited about something and that’s a much better transition. And he has a formula of course Jason: Burn out now is doing something the company needs and then you might be good at but you don’t enjoy. You have to have all three elements or you’re gonna burnout. And so here’s a link to his talk from last year where he talks about these things.

So let’s wrap up. Here’s what I found what motivates people to keep going after they’ve made it. One is actually I haven’t made it yet and this is the butcher. Actually if you think about it if the butcher had the chance to you know quit and retire early, they would. They’re not doing it because they want to you know most people don’t do it because they want to build a long lasting business. It’s just that they need the money. Then there’s those who are in the middle of a five year project and do and I’ve just got to see this through right. Maybe when this is over I’ll think about what to do next but right now I have this big vision and I want to execute it. Then there’s those who are like I’m never done. I want to see how big I can get. I want to be richest person in the world. You know I know a couple of these. And then there are those who say. I managed to carve out my role in my company and this you have to believe to a point. I’ve noticed from my conversations it might work for a while but maybe I’ll report back on that. And then there are those like I don’t have anything better to do right now. I don’t have anything to run towards until that shows up. I’m just going to continue working on this because I enjoy it. So for me my next three steps are make my job fun again. So I took some more creative projects. I get to basically step back from the brink a little bit. I got involved in some teams more heavily again because I need it to feel good. Otherwise it all falls apart. It’s not going to be my full time and it’s not going to take all my time but I am I’m doing some productive project stuff. Taking care of my mental health with exercise and hobbies. On next Tuesday I start a 60 hour woodworking class in Bologna I am super excited. Nighttime classes. And then the guys still shows up every morning. And also I’m gonna make new friends. It’s a project I’m going to use the formula. So if you want to be my friend please later come over and meet me. And then make Balsamiq stronger. It doesn’t mean I’m leaving. It doesn’t mean I’m planning on leaving but it means that I realize that this is not the right way to continue. We have to get to that next level where it’s not I’m not required as much. So I’ll continue working on it with the awesome team. I’m basically following their lead at this point for this next phase I’m watching what they’re talking about. They’re having all these meetings and I’m not going for it for fear of if I say something they’re gonna destroy everything. If I don’t say anything they’re going to think I hate it you know. So I just don’t go to meetings and then I’m going to read a bunch of these books that have been recommended and sort of clear my mind that way do a lot of introspection. What do I really want to be? Where do I get my kicks from? If it’s not from you know what does Balsamiq give me that I get so much pleasure from? And does it need to be from Balsamiq or you know at some point when I retire what will I do then I want to talk to a bunch more people because they worked made me feel a lot better. Yay, now I have a five year project to execute. I found what I can do in the next five years.

So the real title this thought could be that it’s actually not that lonely at the top if you make an effort and reach out. It was scary to send those emails, it was scary to come here and talk to you about all this stuff but I think it’s also worth it. So you guys are smart because you came here. This is the only place in the world where we can talk about these things you know in a intimate way in a meaningful way because people have had these experiences or will likely have these feelings and experiences so good on you for coming here. So use the rest of the conference time to really try and make new connections. It’s what makes people happy in life. We’ve learned right. Use me as a meeting point if you want to talk about these things. Come around me. We’ll be a roving pack of rich guys. It’ll be great commiserating with each other here. Thank you.

Mark Littlewood: Fantastic. Yeah. We’ve been talking a little bit about that talk and how it’s been going on over the year and just great. I’m so pleased you’ve got so much from BoS as well so keep coming Peldi! Questions!
Audience Member: I just came to ask Peldi this. Thank you for coming along and being as honest as possible. One of the things that I really struggle with is one of the reasons you set up a company is you get to do the things you like and you’re trying to build the coolest company on the world and you suddenly realize one day the only person is not happy at this really cool company and doesn’t get to do what they like is you. So do you still give yourself particularly if you’re a technical guy. Do you still give yourself permission to try to do things that you like. Even if you can’t justify them as a CEO or do you accept that’s part of growing up in life as a CEO that you don’t get to do those anymore.

Peldi Guilizzoni: So I am ambivalent about it. For many years I’ve kept some things that were fun right. The wireframe of the features was fun and fulfilling and I did that. Right now I have an internal tool that I sort of own the development of but those are things that are kind of easy to fall back on while instead I should be doing the frigging CEO job. And so I don’t know. I don’t know. Maybe if you are good you train enough people you put enough processes and structure in place so that you know you sleep well knowing that everything else is taken care of and then you do what’s fun for you. But I’m pretty far away from from that right now. So I think that there’s jobs that everybody has to. Somebody has to do them. My default is I’m the servant leader I’m at the bottom of the pyramid. I will take out the garbage all day so that the bad ass team can focus on what’s important right. And I did it for 10 years. And it was fun. Now I can’t even take out the garbage. It’s pretty sad. So I don’t know the answer is I don’t know.

Audience Member: Hi. Thank you very much. Really incredible to hear all of that disclosure if you like and relate to it and I’m sure all of us can talk about that and the coffee break as well about things that really resonated. But this might become a bit meta but one of the challenges that you have if you’re running a company and you start to feel that sense of disconnect between the perception everybody has about the success of the company and how you personally are feeling running it is it’s difficult to share that with your team because you don’t want to go to a team meeting and say hi guys just like let you know I’m failing, I’m failing personally and I’m down. And good luck because that’s obviously not a good motivating message. Good. So is it to avoid being a bit too meta about it. How have you reflected on this year and in building that talk knowing that your team are interested they’re going to be watching you right now right. Talking about it. So how much of this if you disclosed to them and what do you feel how are you going to manage that when you head back?

Peldi Guilizzoni: So I try to be pretty transparent with the team always. I try to set the bar pretty low and keep it there so that they can expect things like this from me but I’ll be absolutely honest. The reason I’m really nervous about giving this talk is because there’s four employees right here right. It’s not about you guys. Really good that I was bringing all this stuff on them and it’s gonna to spread the word. And you know it’s but to me that’s also an opportunity to start these conversations and none of this should be a big surprise. You know maybe I didn’t go into as much detail with them about what I was feeling until now. But to me sort of this is something that forces me to sort of come out once a year or so thank you. This is for me. That’s one of the jobs to be done of this conference. So I guess you know they don’t. They love me. I love them. We don’t they we shouldn’t keep things from each other even if they’re really tough. And overall you realize that the team kicks ass and they’re going to pick up the slack and even drag you like it’s happening to me right now. So do it even if it’s hard.

Audience Member: I was at the talk in the UK in 2000 17 minutes from a flat structure and I organized projects and we’ve actually gone a little bit down that path. So I’m curious when you took a hands off just the teams have they still aspire to the same lack of hierarchy and flat structure. And if they didn’t were you prepared for that because I think that’s something that you have very strong?

Peldi Guilizzoni: So the answer is yes they are still flat but they’re very much talking about all the confusion confusing point of our written policies because really there’s a big unwritten part about it which is if this doesn’t work Peldi is there and he follows everything when that is gone. It exposed all the limits of what we wrote down and what still needs to be written down. So now they’re having these meetings to sort of clarify that maybe we come up with a daisy or whatever it was called RACI system instead. Nobody has said we need managers now. As a culture we’ve been very very proud to be self organized and I’ve been trying to push hint every few years about maybe what we need is someone who does this sort of management thing. It’s not that bad but they’re like no not yet. Maybe we can try these things first then OK sure fine. Maybe it will work. We’ll see. We’ll see. But no not every team sometimes didn’t even notice any of this happen. Some things are kicking ass. They’re just doing their own thing. They’re excellent. They didn’t ever needed me anyways. And so they’re like that is this all about right.

Mark LIttlewood: So Gareth: if anyone’s looking for someone that knows the onions in terms of coaching Gareth was COO at RedGate for 10 years. This is free advertisement. So as long as you’re not going to come but put in some kind of pitch to say I’m a coach there you are, the floor’s ready.

Audience Member: Funnily enough Mark I am a coach and my question to you Peldi is do you have one?

Peldi Guilizzoni: I’ve hired Paul Kenny in the past on a suggestion from my wife which is smart. She should be running the company anyway. And we did a six or seven sessions to answer one question: What is the job of a CEO. Because I really needed to know like what am I supposed to be doing. And so we defined it to define that. And I’m still kind of executing on what he taught me a couple of years ago. But he came from the traditional answer which is well you’re not supposed to be day to day I don’t think that what he coached me I applied to a crazy company like us where it’s one man who’s over 30 employees. And so I don’t know there is a coach that is willing to do to figure that out. But I do feel the need for someone because I need to have someone to coach me and to vent to that’s kind of one step removed. So I’ll be looking into that again.

Audience Member: Peldi… The question everybody wants to ask. How did you delete twelve thousand… And still thrive and what backup solution were you not using?

Peldi Guilizzoni: So I’ll keep it very quick. We’ve had a web app for many years. We rebuilt it completely now. So we launched our new web app last October. So it’s a very sort of a young product. It’s taking off like a rocket and we’re trying to keep it going. You know we’re struggling with the operations because it’s successful and at some point we decided that some projects were too heavy to be in the database so they needed to be moved to S3. So we moved to S3 and forgot to turn on backups on S3. Simple as that. And I wasn’t being the Engineering Manager at the time anymore. I delegated that to someone who had never been an engineering manager ever. I didn’t give him enough coaching. All right. It is a result of this Injected Turbulence. I feel like if I were to have kept looking as closely as I’d been looking it might not have happened. It might have also, I don’t know. But yes as simple as that we forgot to turn on backups on a new storage system that we have used rarely in the past…


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