The Final Deadline... Or: A Deadline, Finally.

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Welcome to Arvid and Tyler catch up. I'm Arvid.

I'm Tyler. Let's catch up.

That's right. Yeah, let's get you up. How's your week been? I think we've been missing yet another week or I always phrase this in a negative way.

I think we just decided to give ourselves one more week between episodes, right? To accumulate interesting things to talk about.

How about that? Is that the better way of phrasing it?

It's been two weeks. Just three, you know, just ask.

It is now two weeks later. I'm still glad we're still doing this because I think this is episode number 12 if I'm not completely wrong.

And I think that was the amount of conversations that we initially kind of committed to.

Right. That's that's what I remember. So I'm glad that we made it here and I hope we'll make it way further than this in the future.

But already being here is so cool. How have your last two weeks been?

They've been good. They've been good. Yeah, really busy in a good way.

I think like, you know, if folks have been listening from the beginning, they know that my day job running the company fund has been kind of all over the place the past couple of months in terms of just a lot of work and decisions and stuff that is not the core business of just meeting with founders and investing with them and then, you know, helping out the portfolio companies as best I can.

And these past two weeks, more or less the last kind of five to six weeks have really been almost entirely that, which has been great.

So I've been spending a lot of time just reviewing reviewing companies to invest in meeting with some actually writing a couple of checks, which is great.

We've got new companies joining the portfolio imminently or rather already closed.

So, you know, they're in the process of being on board and all that sort of stuff and, you know, keeping the LPs up to speed and all that kind of stuff, which has been which has been really good.

It's been kind of interesting to see some of the conversations with founders have surfaced an interesting kind of conundrum right now, which is for folks who are not that plugged into the investing world right now.

There's been this really dramatic change in that world over the last kind of six months or so, which is we transitioned from this period where there was just lots of capital out there.

Valuations were kind of crazy.

Everybody was able to sort of founders were able to sort of raise money and access capital markets in a way that almost felt like a no brainer.

You know, you say, OK, I want some money, whether it's equity or debt or whatever.

And the terms were such that it was like you didn't really feel like you were giving up hardly anything.

Right. So you go like, sure, I'll take some money.

And now we're entering this phase because, like, you know, interest rates are rising and capital is less available that it's kind of coming to more of a normal thing where, you know, when you want money from investors in some format, you kind of have to give something up.

You have to want it. You have to feel like there's a trade happening here.

And that's fine if you're coming in fresh, whatever.

You don't know. But what's happening is there's founders who sort of have gone across that time period are having a really difficult time kind of switching gears.

Right. It's almost like you got this car that's going in six gear and you're going super fast and you've got a downshift to second gear.

And it's just really hard to do that.

So I'm having a lot of conversations with founders where, you know, they built a great company.

They built a cool SaaS business.

They've got, you know, let's say 30 K and M.R.R.

But, you know, and it's growing and I'm really excited about it.

But, you know, they just a bunch of angels got excited like 14 months ago and they've raised like one point five million dollars.

So their burn rate is like one hundred and twenty five K a month relative to the 30 K.

So, like, even though they've got this business and it's growing, they just have way too much staff.

And so now they're trying to they're trying to do the sequential thing. Right. OK, you raise one point five million. Now you've got to go raise three or four.

And it's just there's no market for them to raise three or four.

And so I'm kind of having these tough conversations with them where it's like probably you're going to have to bite the bullet and normalize your burn rate, which probably means like laying off half the people that you just hired in the last nine months.

It's super hard to swallow that kind of a change so early on in the business cycle.

So it's like, you know, it's just a very difficult thing to navigate as a founder.

And I'm trying to having a lot of those conversations, trying to very delicately help these founders navigate these tough decisions.

So, yeah, it's an interesting market right now for sure.

Yeah, I wonder. Well, let me let me respond to this first, because I really wonder something.

I had a couple of conversations over the last week's mostly about mental health and expectations.

I was talking to Dr. Julie Gerner, who is on the podcast today that I released about, you know, imposter syndrome and those kind of things.

Yeah, she's awesome. And she just got to a hundred thousand Twitter followers as well.

I love the fact that there's somebody who works effectively as a psychologist, like helping people understand mental health issues.

And they have like a six figure Twitter following. That is that is what we need in our community.

So talk to her and about a lot of, you know, the self preservation things that people do, projection things that we do, even, you know,

she said imposter syndrome is something that not everybody has.

Some people think they have it, but it's really just like depression or it's something that is, you know, like a self kind of analyzing where it's really just your own unwillingness to deal with your parts of your psyche that you haven't yet explored.

Right. And your projection of other people's capacity into your own life.

There's a lot going on with imposter syndrome. So I had a lot of conversations with her about this.

And I feel founders that have nobody to talk to, they often struggle with even the most basic things because they have nobody to really understand, just to kind of bounce this back and forth with to understand themselves with or through.

And the week prior or I guess next week when it's being released, I talked to Paul Millard, who we've mentioned many, many times on the podcast.

And we talked about also with VC funding and that the kind of this hamster wheel of having to raise round after round that is effectively a narrative.

That's kind of common knowledge. He calls it that common knowledge, which is us thinking that we know what other people know.

That's what common knowledge is to him. Right. Our expectation that something is known by other people, other people's ideas.

That's kind of the larger term. And I feel in particular around the successful startup founder being able to sustain the choices that you make from the start is part of your identity of success.

Right. Hiring people and not letting them go. Success. Hiring people and having to let them go.

Massive failure, even though the business is still around. Right. But in our minds and I'm kind of kind of putting them together.

And I do wonder what kind of responses do you experience when you talk to people about that being a necessity?

How do people react if you can divulge that? Obviously. Yeah, generally, I think you're right that there is a very strong intuitive need to stick to the narrative of success.

And it's really hard to stray from that, even though you're right that there's no rules that say you have to follow this particular thing.

There are many different ways to success. And actually, if you go and start to reverse engineer a bunch of different folks pathways to success, you often find that it didn't follow this totally smooth kind of just like success compounding on success, compounding on success.

There's often the sort of valley of despair or whatever the trough of disillusionment, whatever you call it.

Like a lot of this stuff often happens, but it's very hard to reckon with it.

And I guess what I am finding pretty frequently is just that there's a sort of it's just difficult to grapple with it.

And there's a little bit of kicking the can down the road, right? Sort of a perspective of, OK, well, we still have a good amount of runway to keep working on this, et cetera, et cetera.

And so I think that it's going to have to get closer to kind of the day of reckoning, right?

Before folks really start to just say, OK, I have to actually grapple with this question, because if you can sort of just hold out hope, there's a very, very, very strong incentive to do that.

And I think that's compounded a lot by you see like something that I kind of will often chime in on when I see it on Twitter or something like that.

Somebody will share some story of like, you know, Jeff Bezos pitched 300 investors before he got his first.

Yes. So like, you know, hashtag just keep going or something like that.

And I often will pipe in and say, like, you know, the reality is that like most of the time you get to like two hundred and ninety nine knows you have like a no.

Like, you probably should have actually stopped at maybe like one hundred and seven knows.

That was probably like enough. You know?

And so there's just this like real, you know, a complimentary narrative to what you're talking about of the idea of just like brutal.

Just don't accept any other outcome kind of persistence that we really sort of valorize entrepreneurs for having.

And that is one that I think folks are picking up in this moment right now, which is like that's going to be me. Right.

I understand everything you're saying, but I'm going to be the one that gets to 300 knows and gets the three hundred and first.

Yes. So that I don't have to rationalize the business in this moment.

And it's very hard to, you know, to try and take that away from someone.

Right. You know, and to some extent, that's not my responsibility.

Like these founders have to make their own choices and, you know, I'm not in charge. So I just kind of am trying to advise them as best as I can about, you know, what probably makes sense.

And then, you know, they're going to have to navigate this kind of weird environment as best they can.

You know, yeah, that makes sense.

What's up with you? Well, I've been I've been having a fun time.

I I'm preparing for my parents to arrive here in Canada, my German parents who speak not a word of English.

It's going to be the most hilarious time that I ever had.

Canada, the calls are coming. Yeah, it's it's the Germans are here.

It's going to be it's going to be fun because like with Danielle's family, that's quite sizable.

There's so many people. They all are really, really looking forward to meeting them.

But between us and like between them and the Germans, there's going to be a lot of translation layer that has to constantly happen.

So both Danielle and I are going to be the translators for a good week and a half, mostly me, I guess, because I'm going to stick with them all the whole time.

Danielle has other things to do living a busy life.

So can't you just, you know, give them some sort of this reminds me.

And this is another story that involves Danielle, because most of the good stories in my life involve my partner with with her as as we build feed by Panda.

Right. The business that we then sold to the wonderful people at the company that you sold your business to as well.

As we built this, we went to a conference in China.

We went to like an online teaching summit that was really, really cool, hosted by one of the companies that we actually integrated into our product.

So that was a big deal. I think it was called Get G.E.T. Global Education Technology Summit.

So we flew to to China. We flew to Beijing.

And it was my first time in China ever. I never thought I would go there.

Getting a visa and all that was interesting and arriving there was interesting and seeing China was it was a lot of interesting stuff.

It was really cool. We went we went to a hotel and the conference was in there, too.

But they had organized something for a couple of people that came there and like an additional little visit to Beijing visit to companies in Beijing.

So we went to all kinds of like education technology companies and technology companies.

That was twenty eight, seven, seven or 18. So it was like before the big AI push in the West.

We went to I think I flight tech or something was the name of that company in China.

And they were they were literally presenting that device that you just said.

They just held it up. Speak into it in any language and it will come out English.

And we did. And it did. It was bizarre.

Like the technology you think does not exist.

It exists and it's somewhere in a Chinese lab that they actually make it happen.

So it was really cool that they showed us like the stuff that now scares us looking at the privacy perspective of it because this thing probably also, you know,

detects everything being said in the room and automatically translates it into some database.

And in China, everything you say kind of has an impact on what you're allowed to do.

There was one company where we went to.

There was a school like a teaching company that had like a camera essentially set up and everybody pointing at everybody and they would read.

Obviously, your face recognition kind of stuff.

But it wasn't wasn't only recognizing your face, it was recognizing your mood.

And it would put the score on top of your face, telling people just how happy you are, where you are right now.

If you said if you're confused, if you understood the things that people told you just now or if you need more help, that's the idea.

So you pointed at a class of 30 kids and you get a little score like a percentage in green or red on top of every kid's head telling you about the thing.

You just try to teach them if they got it or not.

Yeah, from the privacy perspective, this is horrible because it kind of infringes into your own internal world that you sometimes externalize through your face.

But it is technology that exists.

And in a country like this, it will be used for many, many different purposes.

That's as far as I'll go. Right.

It was just an interesting glimpse into the technology as it is being built in a country that we don't really get that much information from.

That also impacts a lot of things that we do, right, because most of our stuff is produced there, too.

So that being said, I don't have that device.

My capacity to translate between German and English will have to suffice for the visits of my parents here.

But we're going to have a good time.

I think there are some pretty good ones out there.

I've seen some launches and stuff you should you should like do a little outreach to some of you know, they're still in beta.

Right. I think that would be like great content.

You know, like there's family and Danielle's family just like beta testing some, you know, both looking at iPads.

Yeah, I think you're really cool.

I mean, that would actually be really cool.

I'm going to spend a couple of hours before they come.

Thanks for that suggestion.

I thought we could handle it.

But why not also make it fun?

Involve technology.

Well, the thing is, I've been I've been preparing for this, obviously, right.

With people coming from from the other other side of the Atlantic, I needed to make a couple of preparations.

That's what most of the last two weeks have been for me.

I've been trying to kind of ramp up the production of what I do, my writing and my recording and my editing.

So I would be able to spend 10 days with my family going to Toronto.

We want to see the big city, right, because we live in the countryside a couple of hours away from it.

They're going to land in Toronto.

We're going to spend some time in Toronto.

Then we're going to go to Niagara Falls, the Canadian side, because there is some some family history that almost happened there.

Like it's there's a lot going on.

But we wanted to see the falls.

We want to spend some vacation time there.

And then we're going to do the whole family.

We're going to bring them here to the countryside and have I think there's a pork pork roast involved somewhere.

Yeah, they got half a pig or something.

And it's going to be like 50 people and they're going to be so confused.

I'm already looking forward to that a lot.

It's like a glorious disaster.

That was my first experience.

I kind of married into a super, super huge family, just a lot of people, a lot of wonderful, every single one of them amazing people.

And I got to meet almost all of them on my first day that I ever came to Canada.

That's that's the experience that my family will also get.

And I'm kind of happy about it.

It's just it's just a different world.

But yeah, I've been I've been recording a lot.

I've been writing a lot just earlier today.

I finished editing the episode with Paul Miller because that's that's the one that's going to go out next week while I'm not even home.

Just preparing everything, scheduling everything, getting my sponsors on board.

There's a lot of stuff to do if you are not on your regular schedule.

So that's what I spend most of my time.

Like for for if you need to get two weeks ahead all of a sudden, like what does that week look like for you?

I mean, do you just have to work a lot?

I mean, how much flexibility is there in your you know, your your current sort of schedule?

I'm actually curious.

It's not we should talk about this a bit more extensively.

Yeah, I think that's that's a good question because I only can tell you really in retrospect now because I didn't really have much of a plan for it.

My plan that I have on every single week that hasn't changed really is on a Monday.

I write on a Tuesday. I kind of write if I still need to on Wednesday.

I do this with you have this conversation and I maybe I pre edit or pre fix certain things for my recording, which is on Thursday.

And Friday is the day that I just push it all out.

And that's order of right, right.

Random stuff record market.

That is my five days a week that I always have every single week.

And what I did this week was really just do twice as much every single day.

And I did the way I did this was by reducing my YouTube consumption by 50 percent.

That's really what that was because I tend to watch a lot of stuff just on the side while I think while I allow my brain to just pull in things.

And this time it was like, no, I'm actually going to write this one article that I really want to write.

And then the other one dates also to happen today.

But I can get an hour of just mental relaxation in there, but not two hours as I usually would.

So that's kind of how that happened and kind of extended into the evenings to with Danielle being doing her her sound engineering stuff.

She often works like late at night as well, or it just does work some projects.

We both sit in here. She sits over there and I sit here.

We both type of way, the little puppies at our feet.

It's a little family workation in our our office here.

But I just did twice as much at any given day.

So I didn't shift anything around because I I don't want to minus minus the actual recording and editing of this week because tomorrow I'm going to be in Toronto for a little conference thing.

But usually I would would have done this recording of everything tomorrow just as regular just do twice as much.

That's how I work. I need my structure.

And the moment I shift like my general structure and in that I can be flexible, but I don't want to be flexible with the structure because I know that my brain is just going to be.

It's just if it's Tuesday and I haven't been writing, then that's kind of how I feel.

It kind of irritates me. So I've developed this over the last couple of years.

I never had that before. How is that for you?

Like how structured is your life, your business life, I guess?

I would say pretty unstructured in that kind of way.

Like I don't have a lot of like on Mondays I do X on Tuesdays.

I do why sort of thing. I think I guess the main thing I do is I try to avoid having meetings on Mondays and Fridays to try and trade those.

So like my calendar, you count Lee will pretty much always block those out so that at least I have kind of more unstructured days or at least on calendar days on Mondays and Fridays.

But otherwise, you know, historically, I've really not had much structure to that.

I tend to tend to just kind of do a mix of, you know, a lot of stuff is fairly time sensitive.

Right. So for working on closing a new investment or all of a sudden something pops up in the portfolio that, you know, companies trying to raise another round or they need advice on something.

Or they have an acquisition offer that they need an opinion on, you know, evaluating these kinds of things.

I haven't like no real control over. They just come inbound.

And so keeping some flexibility there to be able to kind of react to those and have time to respond to those is pretty important.

And then with like larger projects, I tend to really just try to follow the things that I have like real passion for and and let that kind of flow.

So, you know, if I'm feeling like I really have the itch to work on a writing project or put out a blog post or, you know, do some sort of long tweet thread or something like that, I'll just follow that.

And if it's more like it's time to do some maybe less company specific but more just like market research, maybe it would be like digging into A.I.

and looking at what's going on there or thinking about, you know, what's going on in the venture world or these sorts of things.

I'll just kind of follow those threads. But, yeah, I'm not I don't have a week to week structure.

I am trying to work out a little bit more of like a quarterly or almost.

I'm thinking more like an every six weeks sort of flow where I have a bit more rotation there.

But it's kind of a mix of both like not a great fit for me personally and not a great fit for the market that I'm operating in.

Right. Because it's like, oh, like we're only going to review companies on these two weeks. But then like some amazing company comes through the door.

You don't want to say, hey, we'll get back to you in six weeks, you know, kind of thing.

So kind of keeping keeping your options open by not like predetermining specific days or weeks or months.

Yeah, exactly. Yeah, I think so.

Because I just don't control when those interesting work opportunities kind of come on my plate.

Right. It's better to be at least I think it's better to be responsive to those.

It sounds like you have a lot of things to be responsive to.

I would you say like I do wonder because most of the stuff that I do is really just like being active on Twitter.

I mean, that could be things there that I should be responsive to.

But they are like non critical. Like somebody sends me a DM offering me something or wanting to do something for or with me.

Great. But, you know, if I don't reply within an hour, it's still going to be there.

Right. It's like for you, that might be different.

Like how much of the stuff that you do is like both urgent and important if you put it into the Eisenhower matrix there.

Yeah. Yeah. Yeah, I think so.

Yeah. I would say like a high degree of urgency and depending on I mean, urgent is a sort of, you know, extreme word, but time sensitive for sure.

Yeah. Most most stuff is time sensitive.

Yeah. Is that just that the nature of the beast or is that something that you could if you really wanted to delegate or delay or something like that?

Yeah, I think I mean, so investing is pretty time sensitive.

That's the nature of the beast. Right.

You know, you usually don't have a sort of open ended window in which to invest in a company.

You know, there's kind of this general sense of around is happening or just the company's at a moment where they want to fundraise and then, you know, they're either going to have raised the money or decided not to and, you know, a month or so and they might not be there.

So there's that element.

Helping portfolio companies with stuff is also pretty time sensitive.

Right. I mean, a lot of the stuff is, hey, we need to hire someone.

You know, we need to make this kind of critical business decision kind of is pretty time sensitive most of the time.

So, yeah, I don't know.

I'm asking this mostly because it's very opposite from the things that I operate on as a writer.

The only thing that is time sensitive for me and even that is really not that time sensitive is that I send my newsletter where other people have sponsored stuff in there so they can, you know, get their money's worth in terms of exposure to my audience.

But doesn't matter if I send it at nine or five or nine fifteen or if I forget at eleven maybe or maybe the night before because I click send instead of schedule.

Nobody really cares. Right. And this has all happened.

So the criticality doesn't it's not in time. It's more in to do it at all at some point. Yeah. Do you get a lot of like just sort of inbound email with folks, you know, readers or something like that kind of asking you for questions or advice or something that would, you know, like not like just like practical stuff.

Hey, can I get a discount or, you know, whatever? I want to refund that kind of stuff like like real like, hey, I want your advice on my startup, that sort of thing.

Do you get that kind of stuff? Oh, I get it all the time. I get it mostly through Twitter because I tell people wherever I go. My Twitter DMS are open. If you have a question, I will get to it. And I do get to it.

Most of the time if I follow them, they follow me. I get to it almost immediately because that's just I can't see the DM, you know, little notification thing without clicking on it.

And then it either either is like a couple minutes of me typing or record a little video and post it in there because that's easy for me. I turn on my lights, turn on the little button that I have on my stream deck here and then it records so I can just post it.

That makes responses very easy because I could just ramble on for like 10 minutes and it's awesome. Don't have to type. It's spectacular. I highly recommend having a one button only recording set set up for yourself because that just makes async but visual audio visual communication super easy.

So yes, we get a lot of that. What do you record? I record through OBS just on my computer upload to YouTube and then I give people the unlisted YouTube link. Oh, okay. That's pretty good. It's very simple.

Like you can. It could probably build something where once it's done on OBS, it automatically uploads and it copy and paste the link into my clipboard. I don't even have that, but I could do that. I don't.

I just you know, that's one more step where I can, you know, write something nice and nice little personal message for people. But yeah, I do that. And if the video is short, I uploaded straight into Twitter into the DM as an integrated video.

But the moment it's like a 500 megabyte gigabyte worth of a nice, you know, resolution kind of video YouTube tends to be the better place to do it.

So I do this a lot. I do the same in emails. People send me an email, I respond to the email. So I get a lot of those. I get a lot of like semi semi cold emails like cold emails that are also questions.

It's like, hey, we have this product. Wonder if you would be interested. And if so, sure. Here's the link to get your free account or whatever.

And another thing because we've been reading your blog or we've been listening to your podcast. We're dealing with this pricing issue right now. What should we do? What would you pay? Right. It's kind of it kind of meanders into each other.

I tend to respond to every single thing that is not just a cold email trying to sell me your weird SEO stuff that I spend. Yeah.

How do you prioritize that? Where does that fit into your Monday, Tuesday, Wednesday protocol?

I tend to scan my email every two hours or so just for new things. And the moment I see something that I definitely don't want to respond to, I just market scene and it's gone.

I use So I filter it out immediately. If it's somebody reaching out to me for the first time, like they are blocked for life.

That's just not because I don't want good offers for something. But if I get like one of these, you know, these templated cold emails, hello first name kind of stuff. It's just not going to happen. So I don't like that.

And I don't want that. But I just attend. I use the other feature that Hey has, which is what is it called bubble up? Have you have you used that?

Or have you seen it before? It's kind of a the email kind of vanishes for a couple hours and it comes back at 6 p.m.

Or if you do it late in the day, late in the evening, it comes up the next morning at eight. So the idea is that this email is interesting enough for me to eventually respond.

I just don't want to deal with it right now. Push it towards tomorrow. I have a couple of emails in my bubble up that I've been bubbling up for a couple of weeks at this point.

It's just stuff that's not critical, but I kind of want to deal with it. He also has this surprise me feature. So we'll come back at a random point.

So it's just it's really cute. Like they've pulled a nice little email client here. And I have this more as a to do list than anything else.

These emails and anything once a week or so. I just go through all my emails because I get a lot of them, a lot of transactional ones as well.

Like your day on Twitter. Here are the best tweets, that kind of stuff. I get that from Blackmagic or what else I get.

I use Sifton S Y F T E N right to highlight things where my name or my products are mentioned.

So that comes in every day or whenever something happens. So I respond to those. I'm you know, I'm working with the guy who helps me write the book proposal.

So all the emails that that person is writing, they come back to me immediately and I try to interact with that.

There's a lot going on. But prioritizing is every now and then I check and if it's interesting, I do it right now or I bubble it up for the for the next day.

Nice. I like the video suggestion is a good one. I think this is exactly like on topic here.

But I I recently just been recognizing that like I actually get just legitimately too many emails where like the questions are just kind of hard.

So it's like, hey, you know, I want advice on my startup or should we be fundraising or something like that?

And it's like I have to read the deck. And I started timing these things.

And, you know, each individual email was taking me like 40 minutes to, you know, review the relevant material and respond to it.

And I'm getting like 15 plus a day of these. And it's just like, OK, this is actually like not a sustainable system here.

That's interesting. The video response, I think, might might speed it up. That's cool.

I've been doing these Twitter tear downs for the last couple of weeks. Right.

That's my new big thing that I've been doing. It's been quite enjoyable.

And that's really nothing else than me opening up somebody's Twitter profile on this monitor over here, pressing the screen capture button on my stream deck, my Elgato stream deck, not sponsored, but should be.

But that I used to switch between scenes and OBS because I did one live stream once and I set up a whole thing for it.

Maybe a bit of overkill, but it's really useful now because I can just put my little face in the corner like you would have on a loom.

But I stream it as a high quality recording to my local local hard disk or something.

And then I record myself going through their profile in like 15 minutes. That's the idea.

That's what I sell like a 15 minute thing for 100 bucks.

And you get it a couple days after you sign up for it or you pay for it. That's kind of the idea.

After our conversation today. Yeah, it is pretty cheap, but it's also a lot of fun.

So I think we both get something out of it. And it has purchasing power parity pricing, too.

So some people get it even cheaper. People from India or Afghanistan or other places, right, where there is a discrepancy.

Anyhow, what I'm saying is I and that's maybe something I would recommend to you in the sense like if you do video, you can do like the reading and going through the material at the same time as the response.

You don't need to read through it and then start typing. You can literally read through it in a capture as you capture yourself, your little face in the corner and the rest is on your screen and you can mark stuff.

You can highlight stuff right for the person to see you intellectually engage the work.

I think that's what people really enjoy about the data on set.

I'm doing because I click on stuff and I say, what is this from the perspective of somebody who goes to somebody's Twitter profile for the first time?

And then I click around and I try to understand what it is.

Most of the time it's the link that they have in that bio or their header image.

I try to inspect and figure out what it means. And I think that gives people a clue as to how confusing their Twitter profile can be by somebody who just doesn't know what to do with it.

And that is so clearly conveyable if you do it as a video. It's harder to describe this in text.

So, yeah, I would I would maybe install Loom, get the get the Loom professional plan or something is going on or 20 bucks a month or so.

And it's just a little little recording button and you got it. It's really cool.

Yeah. I recommend it. Okay. It's really easy and shareable. It's really nice.

And transcripts. I guess the other thing, because I have I built a little Apple script here for myself because I am into a stuff a little bit like just experimenting with it locally.

And I use whisper opening eyes whisper, which is their audio to text conversion tool.

And I found like I think it's called whisper CPP, which is the CPU bound version that works even if you don't have a good graphics card.

It uses the CPU and apparently it does a minute of audio in like 10 seconds or so of of computing time.

And then you turn it into a transcript. So it was an Apple script that will automatically pull up or instruct a computer to generate a transcript for any given audio file or movie file doesn't matter.

So that whenever the video is done recording, I just right click on it, say run whisper and it automatically generates the subtitle, which all of a sudden makes the whole thing searchable, which is it's kind of like it.

And I wrote an email just by narrating it into the computer. So now you have the audio, you have the visual and you have a text version of the thing you were saying.

If you were writing an email, it would take you like four times as long and it's only text and the other ones are missing. So I hope I'm selling this to you, but it's really useful.

A little how to summary here. That sounds pretty good.

Yeah, it took me a while to get to this point because there's a lot of steps manually that you would need to do if you don't have it automated. But hey, if you need the Apple script or whatever for your own system, I can hand that over.

It's really fun, fun to build these little tools. It's kind of it is effectively no code.

No coding in the original way by just gluing tools together. The GNU way, the Linux way, but just using really basic tools and just intermingling them. But that is my process for communicating and that has saved me a lot of time and actually made me quite some money because I used the same tech for those videos.

So just having all of this in place allows me to, I mean, I promised 15 minute videos and they turn out to be like 25 or 30 because as you could tell right now, I cannot stop talking for some reason. So whenever I'm excited about something or I have something else I want to say, I still finish my initial thought and that may take me 10 minutes.

People tend to get like 20 to 30 minute videos even though they pay for 15. I think that's fine, I guess. But I just have a lot of fun and I learned a lot. I think I ran like 20 or 25 of these now, which has been a lot of work just going through and talking through each of these things.

And this week I'm going to put a blog post out as my regular content going through the three main things that I found. So I'm trying to, I have some paid stuff that also surfaces information for my free stuff. It's all that kind of flywheel, which is my process.

My process is to never do a thing if it doesn't also empower everything else that I do. And my structure is built in that way. I write, I record, I publish, and in publishing I get responses that empower me to write more.

And during recording interviews that I do, I get new ideas for writing and I get new channels for publishing and you know it's all kind of working together. If it's not so energetic, I'm not going to do it.

Mm hmm. Yep. It's a lot to unpack there.

Yeah, sorry. That was one of those 15 minutes things that I do.

Didn't even cost me $100. I love it.

That's right. You got it for free. Yeah. I'm just having a lot of fun doing this kind of media stuff. I really, really enjoy it.

Yeah, no, it's very cool. I would definitely like to see a little more like behind the scenes about how you're actually executing on a lot of this stuff because I know it's quite complicated. I think just even getting like a good audio visual setup and stuff like that was like a very big lift for me and I'm still only like maybe a B minus level.

Oh, you're great. Yeah, there's a lot to be done there.

We're finishing the basement. I think I've mentioned this every single time, every single episode. People are probably going to be super bored with the basement but that's why I want to live. I'm a basement dweller by design, right?

Like I'm a come from the development community. We love our basements and yeah, we're so close to getting it painted and then I can get it set up and get my railing on the ceiling where my microphones and my lights and my camera are going to drop down from because I don't want things on the ground. I want them up and you know, it's going to be a whole studio and I'm really looking forward to building this and Danielle being an audio engineer, she's going to help me like figure out the sound proofing and sound, you know, the absorption panels.

And all the weird diffraction things that you need to put in a room to make it sound good. So that's just going to be a fun little thing and now I'm sitting in a different room and I kind of want to go down there but we're not done yet.

It's just I'm so excited for this whole process. I think for somebody who likes tools and toys going into media is both incredibly fun and super expensive. You don't want to know how much money I spent on equipment that is mostly unused but you never know if you might need it, right?

Like I think I have like six or seven camera lenses right here that may or may not be used in the future, just because I want the shot a little bit tighter or a little bit wider.

Yeah, yeah.

For something that will never happen. Yeah, it's, yeah, it's a lot of fun to build this this little business but it certainly requires a lot of restraint, because I could spend time on all of this all the time.

But I, that's why I'm saying and I do wonder that's one thing I wanted to ask you, like, how do you keep yourself accountable to actually get things done? Because for me, that is having subscribers having readers having viewers having people that expect me to deliver every Friday, so I have my structure in place to make it happen.

But how as somebody who doesn't have that much structure, minus the, I don't want to have meetings on Monday or Friday. How do you set accountability goals and how do you reach them for yourself?

It's a good question. I mean, I, I have never been one to set kind of goals in the form of milestones, really. I often find that I focus more on the pace and the direction that I'm heading in.

So, other than sort of saying, okay, I want to get to, you know, X six months from now or whatever. I tend to just sort of look at, okay, what kind of pace am I setting in terms of like, you know, a typical week, a typical month, a typical quarter, do I feel like I'm getting, you know, enough done?

And then I think about the direction, which is, you know, am I getting enough done? And is it the right kind of thing that's moving me in the right direction? And that's kind of how I focus on it, which is just to have like a retrospective.

So if you can almost think of yourself as like a runner, right? It's just like you're looking down and kind of checking your watch, right? Getting your pacing, right? And saying like, okay, pace feels good.

All right, like definitely headed in the right direction. Let's keep it up versus like, oh my God, I'm, you know, I've got three and a half more miles to go until I hit my goal, right?

Which, you know, I mean, I know that works for a lot of other people, you know, really like to set very structured goals. But the way my brain works is it's much more in that sense.

So I'll and then, you know, I'll adjust, right? So very frequently that it will say, hey, you know, like actually, you know, the pace is not what we want. Why is that? Okay, well, you know, we had some distractions. We had some things that had to get changed, etc.

Or, you know, reevaluating the direction as well. So, hey, got a lot done, but seems to sort of be not quite headed in the right direction. So let's, you know, recalibrate this week in terms of how how I allocate time. So that's usually how I how I do it is kind of like course correcting over time on both of those counts.

Interesting. So to me, this this kind of two camps here, and it's probably more than this, but there's alignment, just what you were saying, right? Like people where do I, where am I pointing the engine? Right? And then people like me, who need motivation, because the engine sometimes stutters, right?

Like, am I alignment is, I think fairly clear for me, I want to do what I like, and I want to help people do what they like. That's the most general direction. And there are specific things in there as well. But I don't I don't feel like I need to reprioritize, I found my stride, but I need to maintain the stride.

And that is more the problem that I have than than my alignment. So the judge, are you just like, genetically somebody who just keeps moving forward, like, like that the motivation and stuff? Are you a disciplined person? Do you consider yourself a very disciplined person?

I think not. But I think, um, for me, oh, man, how do I unpack this? Joy. I think motivation for me comes in the form of, first of all, being very a bit like what we were talking about with the kind of like, you know, other people's narratives and things like that, like, continuously reminding myself that I am free of those narratives that I could really be.

Doing anything that I want, right? And I kind of remind myself of that a lot, like really stepping back and saying, okay, technically, I plan to do this over the next month because I have currently got this job and I've raised this fund and I have this obligation.

These investors, et cetera, et cetera. But, you know, just remember, like, you could change all this if you wanted Tyler, like you could write a note to everybody saying, like, hey, I'm giving the money back.

You could tell all your portfolio founders, like, you know, you guys are great. You're on your own. I'm going to go be a tour guide in African safaris because that's what I want to do now. And like, nobody could stop me. Like, I could do that.

You know, so I kind of remind myself of that. And then I basically, like, consciously re-opt into what I'm doing. Right. So then I say, like, okay, I could totally go and do that.

Do I want to do that or do I want to keep doing this thing that I like? Is this actually like the most fun, important, interesting, you know, all of the right adjectives thing that I could be working on right now?

And most of the time I say yes. And some of the time I say no. And then I change what I'm doing. So, you know, that's why I think, like, you know, I would say, I guess I've got maybe about 15-ish plus years as like a professional.

Adult at this point, like I'm 37. Right. So you say maybe so early 20s, you got 15 years. You know, I've made some pretty big changes over that. It's not been 15 straight years of linear progression on the same goal.

And that's because, like, I am very willing to just say, like, nope, I'm done with all this. I'm moving on to something else.

And so that kind of continuous reminder of I could do something else, but actually, like, of all the possible things, I want to be doing this, then I'm choosing to do this is kind of where I get motivation to keep the pace up and keep pointing in the same direction, I guess, if that makes sense.

Perfect sense to me. That's awesome.

I'm very wary of those traps as well. You know, I think, like, there's all kinds of forms of like, you know, the term like golden handcuffs, right? Like you get stuck in a job that just like pays you really well and then you get like a really big mortgage because you have this job and all of a sudden you're sort of like trapped in this situation where you have these golden handcuffs.

And you're like, life is pretty good, but you just can't really do something else. I tend to like steer really clear of these like golden handcuffs situations or get like very suspicious of them.

Because, you know, I find that I like I need to have the I need to remind myself that I could be doing anything else in order to feel motivated about the thing that I'm doing, if that makes sense.

Yeah, one thing that is that is very pleasantly absent from all of this reasoning that you just shared with me is money. Like, I didn't hear a single word about like, you know, making money or, you know, building wealth, even though it's kind of a layer foundational layer of all of this, obviously, because we have to still like build stuff right built built security or whatever it may be for ourselves or the people we love or just ourselves.

Right. It's just for ourselves to feel value to feel valuable. That to me is what I hear and not money, not the kind of financial thing. I kind of have to recur to what Paul was saying, Paul Millard again, he calls these people hoop jumpers, right, people who jump from hoop to hoop to hoop, because that's the hoop that somebody else places there for you to go through the career on the default path, right? If you follow the regular progression, the narrative that other people put out there for you. And I think that's where the golden handcuffs come in.

Because every time you jump through a hoop, you get elevated into another group. And that group has to kind of be maintained. So it gets constricted and restricted from the outside. And that's that's where the expensive lifestyle that comes from something that I also don't see in my priorities. But I think we both operate from a relatively, if not extremely privileged foundational layer, right? Having sold businesses having financial security, if not stability, if not more than that, right?

it? So I guess for us, it's easy not to talk about needing money because the necessity

has just been mostly reduced to this is okay. It's okay to make more. That's kind of, that's

how I feel about it. But I live in a house that is very small in many ways compared to

what other people live in. We only have, have, you will be surprised, two bathrooms in this

house, only two bathrooms because we're just two people. Why would we need more bathrooms?

So, you know, that's, that's kind of how I approach these kinds of things. My priorities

are equally, I think, or similarly to yours in what do I enjoy the most? What is the thing

that I want to fill my time with the most? And that kind of, in a way that is a highly

structured approach. It just is not structured in the same sense that, you know, most processes

or calendars are structured, right? Like if you kind of, if you chase the thing you enjoy,

you can't really schedule these things because that kind of makes you enjoy them less, but

you can make room for them. And that's, I think, the one thing that I'm just going to

throw this out here, see what you think. Like to me, I kind of categorized, but empty calendar

is the best kind of thing. Like I want my five days, they each have a theme, but like

other than the theme, I don't want anything else in there. I want to be able to fill them

as things happen. Is that similar for you?

Yeah, I think so. I mean, it just even, I mean, I think it's basically yes, and a little

bit even more emphatically, right? So that I don't even really choose the topic for the

day. It's more like my ideal day and where I think, you know, some of the clear most

important and impactful work, the sort of like 100X, you know, days where like, and

this is something I think that is, you know, you and I have talked about in the past about

how like, there's certain kinds of careers, especially once you build a certain amount

of leverage where, you know, every hour, every day is not treated equally. And it's possible

to have a single day's work that is 100 times more valuable than the average day's work.

You write something, you make some connection, you, you know, do something that, you know,

it's just going to move the needle so dramatically. And most of those, for me, most of those 100X

days or pieces of work have come from either a pretty blank calendar, or sometimes I get

a hunch that it's coming on, and then I just clear the calendar. So like a good example

would be maybe two years ago, I wrote this really long thesis for our fund. And that

was that the idea sort of just started, I've been working on the ideas like on Twitter

and in bits and pieces, sort of atomized versions of it. And I could just see it kind of all

starting to come together. So it's like early January, like the first weeks of January.

And it was back in like post holiday work stuff. And I just said no. And I just nuked

my calendar for a week, I told everybody like, leave me alone, like, you know, and I just

sat down and wrote that thing. And that was easily like 100 times more valuable than,

you know, almost any other week that I had put into that business so far. So yeah, it

is, it does typically come from that that kind of situation. And it's tricky to think

about that to know that and then to say, well, shoot, shouldn't like every single day and

every single week like this. Like, you know, like if I could have 600X days in a year,

that would be like incredible, right?

See, that's why we don't optimize for these kind of things, because it just gets you into

this incredibly self-defeating, I need to optimize, optimize, optimize state where most of what

you just said is about giving yourself the opportunity for serendipity. And that's something

you just cannot optimize for because by nature, it is unoptimizable. It's summonable. You

can't just summon serendipity. It falls or it doesn't. What you can be is prepared.

I think that's what I see as the opportunity surface, right? You have as big a surface

as possible for opportunities to strike. And then you have the capacity, the skills and

the judgment to see them as opportunities and go after them and actually implement them

or face them or turn them into something. Because what do people say success is when

luck and skill meet each other or something like that is kind of you. If you want to take

an opportunity, you have to recognize the opportunity. You have to be able to do something

with the opportunity and you have to just have time to even deal with it. Right. And

all of this requires, I think, a little bit less structure and more willingness to embrace

it as it comes. I think I'm similar. I have these days too, particularly my interview

days with people like Patrick Campbell. The conversations like this, they will serve me

forever as an anchor into his world and as a means for me to communicate that I'm serious

about like teaching the community stuff that I find inspiring. And that was an hour long

conversation, but probably one of the strongest ones I ever had. And it's a friendship. I

met Patrick at MicroConf in Denver. We had a real good chat and now we're just chatting

back and forth. And this stuff just, you know, it happens because there was this one day

where I actually sent that Twitter to him and asked, right. And that was probably one of

the most high leverage things I ever did. It's just asking people questions. So you're

100% right to leave room for this. Well, we've been, I kind of want to pivot to the thing

that this whole podcast is about, supposedly. 12 episodes in. I kind of want to pivot to

the Comm MBA a little bit, because we've been having, you know, back and forth between a

lot of structure, very little structure. I think we've now found kind of an initial schedule.

I think that's what we call it for what the Comm MBA and its very first iteration is about.

Do you maybe want to give a really, really concise, I mean, this not because you're verbose,

but you know, really short description of where we're at and then maybe what else there

is for us to decide before we actually get started?

Yeah, totally. So, I mean, the entire idea and in some ways the genesis of this podcast

was you and I talking about how, you know, there is a need for more paving of the path

of building a kind of bootstrapped business, calm company, etc. You know, we were talking

about, I think I was kind of contrasting it with, you know, venture capital and the Silicon

Valley approach is really not a fit for like almost every business, but they've done an

amazing job of creating what feels like a sort of paved path. They said, hey, there's

angels and there's AngelList and then there's Accelerators and then there's Pre-Seed and

Seed and Series A and all this kind of stuff and they give you a sense that there is a

path you can follow to build a company this way. And so that tends to lure quite a lot

of companies and in many cases companies that probably should not go down that path because

like it's kind of one of the only paths that's really well paved and really articulated on

how you can build these companies. And so the genesis of the idea of a Comm MBA was

let's start creating something for folks at the idea stage to convince them that there

is at least one, if not many other alternative paths to build a company. We wanted to do

that in the form of kind of exploring a variety of ideas around how to think about markets,

how to build a company, how to think about hiring, like all the basic blocks of starting

an early business, but through the lens of the outcome being build a calm company versus

a you know well versus any other kind of company really. And so we started this because we

felt like we had a lot of raw material on the topic and we really were not finding how

exactly to get started with folks. There's a lot of interest from a lot of would-be entrepreneurs

in terms of you know consuming some of this but we were like should this be a cohort course,

should this be an accelerator, should this be this, that, the other thing and we said

let's just get on a regular call and work through this. Where I think we have landed recently

is that the nature of trying to find a bundle of founders at exactly point A that want to

go from point A to point B at any given time is incredibly difficult. You're going to have

people who are idea stage, who are you know a day away from quitting their job and super

stoked to people who are thinking about doing it three years from now and getting those

folks at exactly the right moment to put them in some kind of cohort or course or whatever

is just too challenging because it's just a coordination challenge. We might have you

know hundred of thousand people that are super interested and only you know seven of them

are all clustered at exactly the right point in that timeline. So what we decided is to

basically take each of the topics that we would do and just start creating the content around

that in the form of either stuff that we're going to produce, interviews, etc. and not

even necessarily doing it linearly from you know point A to something in the later stage

company but just picking topics off and starting to create that and then once we have much

of that kind of catalog of material really organized then we can start to apply it more

to different things like a cohort based thing like a course like something like that. So

that's kind of where we landed in particular the last episode and I think where we are

now we were just talking before we started which is like I think we're ready to start.

So I think maybe we can just talk about actually in light of this discussion we've just had

around sort of mix of spontaneity and kind of structure you know how do you want to go

about sort of starting to pick things off the to-do list and starting to create the

content. What do you think? It would be really nice to keep the whole building and public

thing going here and just making this something that our potential prospective audience has

kind of a say in right because for us I guess it really doesn't matter if we start talking

about pricing or funding or market like we can only speak for myself but I have something

to say about everything right it's kind of I've thought about this stuff a lot I have

opinions about all parts and so do you like you've been involved in this so intensely

so it really doesn't matter where we start I think it would be interesting with the people

that we already got you got the survey and I have a couple people in my DMs you probably

have several in yours maybe we should really just talk to the couple people that we've

talked to and give them a list of like three four different options for the I don't know

first month that we would like you know talk about it once a week as we probably would

plan to and just have them select the one that they care most about and then kind of

rank it by that or make a list of ten different things that we have a list in our little document

here the the module topics the table of contents right and maybe just put that list in a in

an actual either Twitter poll or a straw poll or something that can have more than four

options and have several people if not everybody in our audience vote about it because it doesn't

really matter to us in which order we do it might just as well do it in an order that

is attractive to the people who might want to consume it that's my idea okay what do

you think too open too public I think the idea I'm almost inclined to say let's divide

and conquer on this topic because my inclination is basically I want to go through this list

and pick what what I'm like most excited about and start there okay go ahead that's also

fine yeah we could do that too like it's uh yeah I mean yeah yeah why not both tends to

be the the answer here like pick a pick a topic and we'll do it with the rest or pick a couple

topics yeah that's that's also fine to me honestly the the question is like when do

we start kind of holding ourselves accountable which is why I brought up the whole accountability

thing earlier because I know that I could do a lot of things in a lot of different ways

but I am a deadline kind of person I need to know that by July 5th or whatever let me

pull up my calendar it's not to promise too much I want to have the first thing ready

to be put into whatever tool kit we choose for it to be made accessible right that is

a whole other conversation that we are kind of and have been kind of having but there

are so many options that we just need to pick one and we can always migrate it back and

forth anyway if we ever make a choice but let's just let's just pick a date because

my I mentioned my parents coming here mostly because during those next 10 days starting

on Monday next week I guess I will be completely inaccessible because I'm going to be somebody's

personal translator for the whole time yeah so that's just gonna gonna make make it two

weeks that I won't be able to do anything but begin beginning July um I could and would

very likely really want to get started with this because man I really want to get this

to a point in 2023 where this is an actual thing yeah like we've been pushing it so far

so what do you think of um well let's let's make it a Friday it's always fun um or do

you think we should put like one of the the first days and the first full week of July

as our deadline for delivery of whatever that looks like the first topic from the list great

each of us let's do it Friday the seventh okay but then my calendar yeah because then

both of us you pick one you mark it in a little document and I mark mine in a little document

and we we get going at it I think that's a that's a wonderful idea I'm really looking

forward to this let's do that I think we can chop it up in in notion we basically can have

the outline and we'll just have a sort of like running database of what we're actually

going to work on and when and you know we can just keep an eye on that and um you know

we'll we'll use that and we'll just get going one day we're going to make that notion document

publicly available and that's going to be fun people can watch us work I mean that's like

that is super advanced building in public that's not necessarily start with that let's

get into you know a certain kind of regular cadence here but I think that would be fun

to watch like I bet people listening to this would be like they'd be glued to the notion

document just to see like how much time do we really spend on this like do we really

do a lot of work or is it just like us typing whatever yeah that would be interesting to

watch I think yeah the seventh is a is a good date I think the seventh of the seventh month

in the third year of the decade yeah that's cool I'm I'm very much looking forward to this

and um yeah now that that's settled it's it's really not much more we can discuss isn't

it kind of sad like we had so much fun not doing the work and just talking about doing

the work and now we actually have to do it oh man let's do the work yeah no I'm excited

do we do you have any anything you you want to share like before we end this here episode

that is now officially an hour long any shout outs because I might have one you go okay

so there was this thing I kind of wanted to mention in the beginning but apparently Denny

Postma one of the very public indie hackers like I think frenemy of Peter levels like

they both built effectively AI products and stuff he had something happen yesterday where

I think you could you could notice like how upset he was about it like somebody effectively

cloned his business the whole photo or not photo AI but like AI headshots kind of thing

that he has and somebody cloned it to the letter like with the copy on the landing page

and everything and then started a Twitter thread about how they are running an experiment

cloning somebody's product and hopefully then he wouldn't be pissed and then kind of involved

him in the conversation it was really bad somebody just somebody burning their reputation

to people from Austria I think building this product and building their reputation in our

community forever or burning it forever by just outright cloning a product and then kind

of in the most cringest of moves publicly speaking about it on Twitter inviting the

person they cloned the product from so what I want to give him a shout out for is I had

a little like private conversation with him around it during the process he was really

mad at it because why wouldn't you be you built these things and somebody just kind

of swipes it and tries to make money off of your work effectively he got mad and he kind

of pointed out how what a shitty move that was and wrote his own tweet and then a couple

like half an hour later after that happened Danny like deleted all of his interaction

with those people and I was thinking this is a confounder he was a bit aggravated for

a couple minutes but then he said hey this why should this bother me right why should

I even give them the attention that they are seeking by making this a public thing so he

removed all of his amplification all of his interaction with these people and now they

were sitting there like getting like three likes on the little Twitter post of their

clone well Danny could finally focus back on building the things that he's actually

good at building so big shout out to Danny Postma for being you know slightly angry at

in the beginning but then calming down again and doing the things that really matter which

is doing the work that we're good at and not complaining or getting aggravated about other

people trying to steal our stuff which people always try to do anyway so that was something

that I found if you want to be a confounder take that as an example like calm calm calm

this is about staying calm when shit hits the fan right that's that's kind of what it is

and that's a good example that I think is worth a little shout out I like that a lot

yeah awesome that's a great share and we should definitely put on our list for future discussion

to discuss copycats because that's something we've seen a lot in our portfolio and talk

to a lot of founders about and it is a very tricky topic that I'd love to talk through

but way too big of a topic to tack on right now yeah that is a whole other thing that

may also be a thing where we want to have a guest and interview somebody else who's

been dealing with this a lot like a person that I may have mentioned just now right like

we can talk to a lot of founders that are dealing with this on a regular basis due to

their public exposure of their work and their personality so yeah that that is a big topic

and probably something that a lot of founders want to know about from the start right in

our very public sphere this might be a big deal but another topic for another day thank

you so much for spending this hour with me having a nice little chat and doing more planning

and a big exchange about structured and unstructured approaches that was a lot of fun looking forward

to talking to you again not sure if I'm gonna hit next week or even the week after because

you know I might be speaking German the whole time and that would be pretty weird for a

podcast like this but July is it's definitely when I'll be be back in full swing working

on our stuff together have fun with the family thanks so much have a good one you too


Creators and Guests

Arvid Kahl
Arvid Kahl
Calmly building in public. Helping founders and creators to find their own way.I write, podcast, and make videos at kind.
Tyler Tringas
Tyler Tringas
Investing in and supporting calm companies at Bringing them together at
The Final Deadline... Or: A Deadline, Finally.
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