Work and Family, with Matt Wensing

December 23, 2021

Matt Wensing (https://twitter.com/mattwensing) joins Aaron to talk about sacrificing time early on in hopes of having more freedom later.
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Transcript

Aaron
00:00:01 – 00:00:32
Okay. So today it's just me, Aaron, and I have a guest that you probably all know, Matt Winsing. He's a fellow bootstrapper friend, somebody that I've known online for quite some time now. We've talked many times. He's a great guy, and he has a product, called Summit, which is forecasting modeling, something that I actually use at my day job to help model out some of our growth stuff.
Aaron
00:00:32 – 00:00:41
And then he also has a podcast, called Out of Beta with Peter Soom. So I'm sure you're all familiar, but Matt, did I did I miss anything? And welcome to the show.
Matt
00:00:42 – 00:00:54
Thank you. You did not. And it's, I love the I love the podcast and I'm looking forward to diving into this topic today. I think we have a topic of the day.
Aaron
00:00:54 – 00:01:08
We do. So I okay. So you have tons of experience. We could talk about growing and selling startups and raising money, but here's the thing that I actually wanna talk about. You've been on a bunch so people can go find those.
Aaron
00:01:08 – 00:01:42
Here's the thing that I wanted to talk to you specifically about. So I think last week or the week before, it was just Colleen and I, and we were chatting. And something that I've been thinking a lot about and my wife and I have been talking a lot about is this, like, this concept of so so I have a full time job, and I'm also trying to do this hammer stone stuff on the side. And I have twins now. They're 7 months old, and I, you know, want to be there, like, all the time.
Aaron
00:01:43 – 00:02:22
And so the question is, how do I, like, how how do I become okay with sacrificing time to work on stuff on the side in with the hope that in the future, I'm able to break free. Like, I'm able to reach escape velocity, drop the day job, and have even more time to spend with the family. But right now, I have less time because I am trying to, like, reach escape velocity, and so I'm doing these two things at once. And it's tough, man. And so that's kind of like, I figured you had been there.
Matt
00:02:22 – 00:02:46
Yep. Yeah, I have. So my my story was I had a job out of college, and we had kids young, real young. So we were married at 22, and Emma was born in 4. So I was 22 and something, about to be 23 when we had our first.
Matt
00:02:47 – 00:03:08
So, and then I started working on Stormpulse, my first startup in 2,004. So about a year, well, actually no, a couple of months after she was born, I had the idea for it and started working on it. And I didn't leave my day job for 2 years. Okay. I just worked on it nights and weekends.
Matt
00:03:08 – 00:03:36
So I basically went through this phase 17 years ago. 17 to 15 years ago, basically. And it was I didn't make I didn't always make great choices. I think, you know, my life is definitely the, you know, looking back in hindsight, like, wow, I'm glad some of these things worked out. Mhmm.
Matt
00:03:36 – 00:03:44
Because if they hadn't, the price tag would have been very painful. Too high. Too high.
Aaron
00:03:44 – 00:03:51
Yeah. That is exactly, that is exactly how I feel on the other side. You're on the good side. I'm on the unknown side.
Matt
00:03:51 – 00:04:25
Yeah. Yeah. And it's not only and so like, let's maybe, you know, I think we can spoil the I'm going to spoil the ending and say there's no way to predict how the, how it's going to work out. And so, unlike a lot of other things where you get many at bats or many swings of the club, you get one swing of fighting.
Aaron
00:04:25 – 00:04:29
Yes. Yes. And you get one swing at early childhood with the kids.
Matt
00:04:30 – 00:05:03
Terrifying. That's that's right. And so you you have to decide if you're going to do this or not, and you don't get to, know if it's going to work out, and you don't get to judge whether or not it was the right choice based on the outcomes. It is independent of that because, you know, I don't believe that, I don't believe in fate. I don't believe in, you know, determinism in that sense.
Matt
00:05:03 – 00:05:57
And I think that you have to imagine that there are other worlds, if you will, in which you could have done the same things and things would have turned out differently, which I find very comforting that like not everything's your fault either. Right. It's not to absolve you of responsibility, but it's like saying, you know, I there's some things that you made the right choice and it didn't work out the way you had hoped, but it would have been wrong for you not to try because you have to try and you have this gift that needs to be that should be expressed. Mhmm. And if you're among people who are supportive, and I think that's the key, one of the keys is, are the people around you sharing that hope and supporting that dream, And are you being sensitive to their appetites and tolerances as well?
Matt
00:05:57 – 00:06:00
Because they're different than yours. There were 2 things
Aaron
00:06:00 – 00:06:12
there that I, I want to dive into. 2 things. 1 was, are the people around you supportive? And the other one was, are you sensitive? I assume you're talking about spouse, family.
Matt
00:06:13 – 00:06:14
Yes. Okay. Exactly.
Aaron
00:06:14 – 00:06:44
So I wanna hear from your perspective and your experience what the conversations were like with your wife. Did you have, like, did you have guidelines and deals? And then how were you careful to be sensitive to her appetite, which I don't know what her appetite for risk or storm pulse was. So how were you careful to be sensitive to, whatever her appetite was? Because those are things that I'm thinking about.
Aaron
00:06:44 – 00:07:17
Like, my wife stays at home with the kids, and so it's basically all on me. And so I want I want to, like, be a good, like, financial family steward and make sure that I'm not taking outsized risks. But her appetite for me working all night is pretty small. She doesn't love that, but sometimes it's okay. So, from your perspective, from your history, what was what were y'all's conversations like, and how did you either do a good job or bad job?
Aaron
00:07:17 – 00:07:21
You know, anything I could learn from. Yeah. I think,
Matt
00:07:24 – 00:08:27
I'll start with a I could have done a lot better and maybe work backwards that it was and I think different peoples, including our spouses or partners appetites for risk have multiple dimensions. So there's the financial element and and there's the personal quality time element. And then there's the presence element with a c, like, are you present? And, you know, finance and financial goals and presence and risk, these are all different factors. So it's good to separate them out because you could have people in your life that are even more comfortable with risk than you are on certain dimensions, and then but they might not be, you know, in the same ballpark as you on other dimensions.
Matt
00:08:27 – 00:08:50
And so for what you can easily do then is you can take for granted, you know, their, you know, willingness to sure sacrifice the salary for a while or do this. But and so you don't because they're so quiet about they're quiet about that, that, you know, it's no big deal. Like, you just roll forward. So you take it for granted. That's one thing.
Matt
00:08:50 – 00:09:32
And then, like, you don't really check up on it because maybe they're silent about it, but maybe you do exceed that at some point. So like sensitive is like this, this thing that you can just be probably 10 times better at than you are now, and I'm speaking for myself that it's the knowns and the unknowns and the constant willingness to, like, check back in and talk about these things. And I gave up a lot of personal income and advancements from 24 to 37, let's say. It's like with my first That's so long. Company.
Matt
00:09:33 – 00:10:06
Yeah. Yeah. I mean, because I don't think there's any years in there where if I had been working at Google or Facebook or wherever else I may have been able to get a job, let's just pick like some ones that are well known and and pay well. I mean, heck, the job I left to join my first company, they were just empty you know, it's a profitable private business that was just sort of emptying, you know, emptying trucks of of money into our banking on a yearly basis. And I left that to Yeah.
Matt
00:10:06 – 00:10:28
I left that to start the startup. So so I gave up a lot there. And I think when you're young and excited, it's easy to skip over that. But like 3, 4, 5, 10 years in, that calculus changes because now you've left behind all these compounding vendors, and you're starting to see friends of yours who
Aaron
00:10:28 – 00:10:28
took
Matt
00:10:28 – 00:11:24
a different path, bearing fruits that you can't, like that ski vacation on top of the new car is not really possible because you have a startup and all of your net worth, you just watch that pie chart evolve from, how much net worth is in savings and cash and, you know, mutual funds to, oh my gosh, you know, 99.9, because illiquid and, mostly speculative still because something's only worth something if somebody else is willing to pay that for it or reward you that way for it. So you can't eat options or equity. You can't Nope. Use them to pay for the Send the girl to summer camp. Exactly.
Matt
00:11:24 – 00:12:15
You can't send kids to summer camp. It is the most illiquid thing you can have. And so like the financial part has these, initial risks that you take, but then keep in mind the compounding distance between you and like that other version of you that stayed where you were and kept doing those things that were proven and fruitful and a sure thing effectively. And that gap gets wider and wider over time. And I think your job as an entrepreneur is to take steps as often, not as often as you can, but when you can take steps to close that gap, so that it's bearable again, so that you're not, you know, this is for a limited time and then some reward.
Matt
00:12:15 – 00:12:52
So, you know, my personal income kept going up at least over time, but that gap was wide still. And I, I mean, if if if my first startup hadn't been acquired, I never would have been able to make that up. Like, that would have been just opportunity cost lost, forever, probably. I would have a ton of experience and lessons learned, but nobody was gonna nobody's gonna hire me and back, backfill my pay for 10 years of income. But that's effectively what we got to do because of the sacrifice.
Matt
00:12:53 – 00:13:06
Right? So it was, the way it ended up working out is it was as if I had been saving all of that money year after year after year. And then somebody one day showed up and said, where do you want us to put this?
Aaron
00:13:07 – 00:13:09
And that's awesome. Yeah, exactly.
Matt
00:13:10 – 00:13:44
And that's awesome because then, you know, you didn't spend it, right? You were forced to save it and, you know, that's pretty awesome. It's like the, it's delayed gratification and a forced savings plan, if you wanna look at it that way, in a positive scenario where we couldn't spend this for 10 years, 7 years minimum. Right? And I can't, and I'm skipping over a ton of tools and techniques that you could use to find liquidity sooner, you know, setting your company
Aaron
00:13:44 – 00:13:44
up and
Matt
00:13:44 – 00:14:06
doing, there's a lot of stuff you can do there. But I don't think the fundamentals change very much is that you're stepping off of the much more lucrative path and hoping that it pays off. If it doesn't, there's a lot of pain there because you you don't get a redo, right? You don't. You just
Aaron
00:14:06 – 00:14:46
No. And what was the so sticking on the financial side, before we go back to the being present side, on the financial side, what was it like in those intervening 10 years emotionally for you thinking like year 5, year 7, when your friends do start to hit those compounding returns and they're now partners at law firms and whatever, and you're like, man, I could have been a whatever at Google, staff, whatever. And so what was it like, you know, year 2, 3, 4, maybe you're excited. Year 8, you've got maybe 1, maybe 3. I don't know the timing of your kids.
Aaron
00:14:46 – 00:14:47
But
Matt
00:14:47 – 00:14:48
you're 8.
Aaron
00:14:48 – 00:14:54
How does that feel? And, like, how did you how did you handle that? Oh,
Matt
00:14:58 – 00:15:05
it was I mean, I hate to say it this way, but it was pretty it was sort of excruciating. Right? Like Yeah.
Aaron
00:15:05 – 00:15:09
Well, that's that's honest. That's what I wanted. Yeah. I mean,
Matt
00:15:12 – 00:15:36
there's no easy way to, I'll pick a different topic. Who is this? This is a, I think this is Televism, author of the, of the Black Swan among others. And he talks about how, you know, you're that person who comes to the Christmas gathering with your family and the brother or the cousin or the sister became a lawyer. And what do you do?
Matt
00:15:36 – 00:16:24
You work in a you work in a cancer research lab, you know, making an honest living as a scientist, and, you know, you're living within your means and all this, but like, you're basically saying, like, I'm either going to have this breakthrough and it's gonna be completely worth it. I'm gonna contribute to humanity in this amazing way, and then everyone's proud of you. But until then, you're like your your brand, your personal brand is this person who's maybe not even that like, you're ambitious, but in a different sort of way. You're not ambitious in the way of showing up with all the presents and opening up the trunk of the Mercedes. You're ambitious in the sense of like opening up the minivan and it's like and and and making do because you have this dream, you know.
Matt
00:16:24 – 00:16:58
And and that's fortunately within America, at least, we have the cultural sort of privilege of entrepreneurship and founders being at least a cool thing. And so there's that, you can ride that, you know, that banner or have that pride of, being that. And so it's not, I wouldn't say it's, it's not shameful the way it is maybe in other cultures. However, it's also, as Tevye says, I love this line. It's like, it's no shame in being poor.
Matt
00:16:58 – 00:17:34
Then again, it's no great honor either. And, you know, it's, you know, maybe you're not poor, but you're also not that person who everybody can easily see those external validations that you're being smart with your time and money and talents. You know, you might, you might be a little, a little, crazy or wrong about things. And that's hard. And I think the other thing to keep in mind, and I would recommend that people think about this before they take the leap.
Matt
00:17:34 – 00:17:57
If your first act can be at a Google or a Netflix or a Facebook or a fill in the blank brand name blue chip company, I would strongly consider that. I didn't do that. I wish I had. You know, I did my 2, 3 year stint out of college at a company that was phenomenal, but not well known. Mhmm.
Matt
00:17:57 – 00:18:10
And that's also something that's hard to get back because you're probably not gonna go back to corporate life if your startup, whether it works or doesn't, you're probably, you know, on that treadmill. Maybe. So that would
Aaron
00:18:10 – 00:18:15
give you some more optionality if you took a big name brand early on? I think having that
Matt
00:18:15 – 00:19:08
on your resume early on, it builds trust in you and your brand, your personal brand, that's gonna pay off in a variety of ways, you know, because you, maybe you've had some stock in that company, you know, that it ends up doing well, or you just have that on your resume, and you can always fall back on that. But that's not a bad insurance policy or or golden parachute. So, I always knew I could go find a job, but it was, it was it was increasingly painful because I really had no way of justifying the sacrifice at some point without an exit. Like Yeah. And that's not something you can just easily conjure up, at a multiple, perhaps that you find exciting, you know.
Aaron
00:19:08 – 00:19:17
Man. So you got so far in that it only would have paid off with an exit, and then you exited. That's right. Oh. Yeah.
Aaron
00:19:17 – 00:19:21
That's, that is, that's a boss measure. That's super intense.
Matt
00:19:22 – 00:19:39
Yeah. Yeah. And it and and shifting away from the financial, like, that intensity had had a cost. So, you know, the lack of the lack of prep you know, we stayed a small team. I was required to contribute on so many fronts.
Matt
00:19:39 – 00:20:06
I was mentally disengaged from a lot of family life and personal life for a long time. And, you know, that showed up in just the inability to be proactive about things. It wasn't that I wasn't there. That's one of the nice things about working full time in a startup is you're there, you're around, but that doesn't mean you're there there. And that is really dangerous.
Aaron
00:20:07 – 00:20:16
Help me understand that, because I want to learn so that I can do some of the same things, but that's what I want to do differently.
Matt
00:20:16 – 00:20:17
Yeah. Yeah, exactly.
Aaron
00:20:17 – 00:20:23
You said not be proactive. What did that look like, for you and your family?
Matt
00:20:24 – 00:21:01
Yeah, it just meant that I, all of the, all of my mental horsepower that had the ability to think about the future and have a vision and strive towards something greater was going into the startup. And that just means that you're not sort of, you know, thinking about, you know, what what are we gonna do this summer? You know, what do we need to do this weekend? What's going on? So all of that burden falls on your partner or your family, whoever.
Matt
00:21:01 – 00:21:38
And that's a very, that's a silent, heavy load that, you know, is, is exhausting. Right. And, it's easy, you know, it's really easy for me. I tend to have maniacal focus on the thing that I'm trying to achieve because you have to. So I think, you know, special honors are reserved for the partners of entrepreneurs because we kind of have this like Olympian, like I think we have to have like this Olympian like obsession with our trade, with our craft to be one of the ones that succeeds.
Matt
00:21:38 – 00:22:06
You know? You just can't you can't be mediocre and survive for 14 years running your own company and get an exit. Like, it's just not it's not possible. So so then, you know, the the tough thing is you can end up, you know, where, okay, I either continue to pay this high price so that we can finally get the reward that we're looking for, or I stop and we don't. And that's now it's all for naught.
Matt
00:22:06 – 00:22:24
Yeah. Right? Yeah. Now it's all for naught. So so one thing that I did do is, I actually stepped back from the CEO role of my own company at one point, and that was really helpful because I was able to just be more of an employee and a contributor.
Matt
00:22:26 – 00:22:54
And I also had sort of a co CEO. He wasn't that, but he was our executive chairman. He carried a lot of the carried a lot of the load that I might've carried alone otherwise. And so I found sort of in steps around 2 starting in 2015 and then again in 2,000 17, I found other people to lead the company in ways that I was doing solo before, and that was smart. You know?
Matt
00:22:54 – 00:23:22
So, I had a co founder, but it's different when you have a team and most of your time is spent managing, and now you need people who can just do more, and that really helped. That started to help. But one thing I did have to do a lot of is because we were an enterprise sales enterprise SaaS is I was still our top salesman for years. And, you know Brutal. Pre COVID enterprise sales, you're not doing that over Zoom.
Matt
00:23:22 – 00:23:32
So I was flying from Austin to Portland, to Denver, to Boston in the same week. And So
Aaron
00:23:32 – 00:23:37
you were physically not present for a good portion of time as well.
Matt
00:23:37 – 00:23:58
Yeah. I mean, exactly. There were, there were, you know, I, it often it was once a month, where I was gone for a few days a week. Some months though, it was 3 times. Some months so, you know, you you have some months look more like a Deloitte consultant's life.
Matt
00:23:58 – 00:24:18
Yeah. And you have, you know, children. It's, it's just you gotta be aware of like the the this the sacrifice that other people are making for you to be able to do that. And I think, in some in some ways, the better our family and friends are at supporting us, the less the easier it is to take that for granted. Right?
Matt
00:24:18 – 00:24:20
Yes. So, that's kind of
Aaron
00:24:21 – 00:24:24
When there are no signs of fire, you don't feel like you have to attend to anything.
Matt
00:24:24 – 00:24:51
Yeah. It's like this weird fact that like the best people, don't complain about it and Mhmm. And that makes it really easy to take things for granted. So so I did that and I, you know, wish I could not have done that. But at the same time, there's that maniacal focus of just saying, but we, this has to pay off, this has to pay off.
Aaron
00:24:52 – 00:25:35
So, looking back, are there things you talked about your spouse partner being extremely supportive and carrying a lot of that load. Are there things now that you look back and say, I could have, like holding constant the fact that you had to be maniacally focused on making storm pulse work and getting to the exit, Are there some easy, small, tactical things you could have done with regards to relationship with your spouse that would have, that would have helped? Holding constant the fact that you couldn't just, like, shut your brain down at 5 o'clock.
Matt
00:25:36 – 00:25:45
Yeah. I would I'd probably look at the things that I started to do that did start to help and just say I could have done those sooner. Okay.
Aaron
00:25:45 – 00:25:46
Go on.
Matt
00:25:46 – 00:26:19
Yeah. So, I mean, and this almost sounds, this almost sounds a little weird. It sounds because they're tactical, they sound a little just mechanical, I guess they'll say, or like cold. It's like, oh, that doesn't give me warm and fuzzies, but like, that's not the point. It's like, I started to so I have one on ones with my, with my executive team well, with a specific member of my executive team at each day.
Matt
00:26:19 – 00:27:00
I started to really treat and realize that my family, my spouse, my wife was a member of my board and executive team, if you will, in life. And say, like, I need to have a 1 on 1 every day with her in addition to my team and do that, you know, at this time each day so that I can set so I can jog my memory, look at the calendar, remind myself what the heck's going on today. How can I help today? What can I do? And even though it's, like, coldly practical in that sense It
Aaron
00:27:00 – 00:27:03
is it is practical. Yes. It's not a date night stuff.
Matt
00:27:03 – 00:27:08
That's not that's not what that's not what the family needed. Right? It wasn't like, hey. We need you to spend, you know, sure. Yes.
Matt
00:27:08 – 00:27:59
That too. I'm not saying not that. But I think the logistical and just practical presence and help could have been assimilated into my work life sooner had I treated it more like a, oh, my team this is a teammate, if you will, that's not just gonna do everything without me or doesn't want to just do everything without so, sure, I can just show up at home at a certain time and then, like, oh, yeah. This kid's got this game, and this kid's got this, and then there's this practice, and I have to do this, and I can, like, see all this. But that's like, it was it was stupid that I didn't realize sooner that, no, obviously getting ahead of that even by 8, 12, 24 hours, 5 days.
Matt
00:28:01 – 00:28:14
That's actually really not hard to do once you just make the routine. It's an atomic habit, if you will, of just saying, okay, it's 8:30. Let's talk for 15:30 minutes about what's going on today and tomorrow.
Aaron
00:28:14 – 00:28:25
And that would help take some of the the burden off of her of you being always like just in time, like showing up and being like, oh, there's a thing. Okay. I guess I'll go. She kind
Matt
00:28:25 – 00:28:50
of knew you knew. Yeah. And and that, you know, I would if I had done that sooner, I think it would have helped more. I think, you know, not having done it sooner, it was sort of like showing up to a busy, you know, showing up at a busy kitchen and you're in the, you suddenly you're in the back of the kitchen and everybody's already doing everything without you. And you're like, you know, how can I help?
Matt
00:28:50 – 00:29:05
Sort of like, we gotta figure out how to run all this without you. So I don't really know if there's much you can do, but I mean, I don't know, look around. It's like, you know, don't wait until the kitchen is working without you. Like, get involved.
Aaron
00:29:06 – 00:29:10
Super extremely helpful, especially for me specifically at
Matt
00:29:10 – 00:29:24
my stage. That's extremely helpful. Yeah. Cause I was a member of that kitchen staff that, what's it called, you know, sort of the back, back office, if you will. I was a member of that team before back of house right before.
Matt
00:29:24 – 00:29:38
And then, at some point you're like, oh, I just, I just show up, you know, dressed in the uniform and I act like I'm a member of the staff, but I'm not really contributing. Right. And that's a problem. Right. So I should have done that sooner.
Matt
00:29:38 – 00:30:00
And I think the nice thing about that, it was just so practical. It's like, but why not? You know, we had 4 children and we have 4 children, so we have a bonafide squad of people at our house. So, you know, 6 people is enough to need a sort of offensive and defensive coordinator and a team captain. Yep.
Matt
00:30:01 – 00:30:03
For sure. So, so be that A little bit
Aaron
00:30:03 – 00:30:04
of a planning meeting goes a long way.
Matt
00:30:04 – 00:30:10
Exactly. So be that, be that team captain or co captain as soon as possible. And don't wait.
Aaron
00:30:11 – 00:30:43
Yeah, that is exactly the kind of thing I was looking for because it sounds like it sounds like, yeah, that's easy. That that's a nothing, but that can make a huge difference and it doesn't fundamentally change the fact that you had to go all in, you could do both. Like, you can you can be extremely focused on storm pulse, but still have a conversation with your wife every night about what's coming up. Like, those things can happen together. Yep.
Aaron
00:30:43 – 00:30:53
So that's really helpful for me to understand as I'm trying to think about how do I balance this time right now.
Matt
00:30:53 – 00:31:34
Yeah. I mean, your relationship health is like other kinds of health and it's easy to stop exercising, start eating badly, stop sleeping, all those things, and stop talking to the people that matter to you about the things that are both like big and also small because the small things accumulate. So, so it's a health thing. And I think that's the biggest challenge with obsession is that people tend to let go of their health relationship, mental and otherwise, and physical. And so treating that like a health matter where you can just stop exercising, but that will catch up with you, it was the same thing.
Matt
00:31:34 – 00:31:49
You know, your body doesn't complain until it's really late in the game Right. Sometimes, and neither will the people that love you and are supporting you. So Yeah. Don't take your body for granted. Don't take your those systems for granted in the same way.
Aaron
00:31:50 – 00:31:52
Yeah. Yeah. That's really helpful. And then
Matt
00:31:52 – 00:32:21
if you, you know, if you fill those things first, you'll know what to say no to to the other stuff because the other stuff will fill a 100% of your time. So, like, I listed out the things I'm not gonna do with the 2nd startup. I have a lot more slack in my second start up intentionally because I learned a lot of those lessons, and also I I don't do speculative meetings. You know, if somebody wants to chat, it's a DM. You know, if somebody wants to meet me for the first time, great.
Matt
00:32:21 – 00:32:49
Maybe one day when we're in Austin, you know, whatever. But it's, you know, that all stuff gets a no because this stuff fills first, and it turns out that a lot of the stuff you're gonna spend time on with your startup is a total waste of time. Yep. Absolute freaking waste of time. You don't know what it is, but it turn if you trim the bottom 30%, you probably aren't gonna miss the thing that matters.
Matt
00:32:49 – 00:33:10
Like, if you do 70% of the experiments or 80% of the experiments, you're probably fine because a lot of them, you were stupid for even taking those on. They're not gonna work. The customer is not gonna say yes. So flying to Delaware just to get a face to face meeting with them before Christmas is stupid anyway. Yep.
Matt
00:33:10 – 00:33:28
So don't do it, you know, and you won't have the time to do it because you are doing these other things first, and that's okay. And like realizing that you're actually not a good manager of your time, so sacrificing the stupid
Aaron
00:33:28 – 00:33:28
part Yeah.
Matt
00:33:29 – 00:33:50
Or the speculative part is completely worth it because a 30 minute meeting that might turn into a big deal one day is way less it's a much poor use of your time than 30 minutes on, you know, the rower or 30 minutes with your spouse or 30 minutes with whatever it is. Like, you can, you'll be better. Trust me. You know, give yourself some slack.
Aaron
00:33:50 – 00:33:58
Yeah. Yeah. So with Summit, obviously things are completely different. You're much older. No offense.
Aaron
00:33:58 – 00:34:05
I mean, 14 is a long time. Yeah. You're much older. You've had the exit. Your kids are much older.
Aaron
00:34:05 – 00:34:27
How you've listed a couple of things, but how are you navigating? Like, are are you just did you downshift? Are you just taking everything slower? It seems like you're still maniacally focused, but you've learned all these lessons over 14 years. And frankly, you're not as dependent on making it work because you made the first one work.
Aaron
00:34:27 – 00:34:39
So Right. What's your life like now? And are you trying to specifically not do some of the things you did the first time besides like speculative meetings and stuff, but like on the family front?
Matt
00:34:40 – 00:35:03
Yeah. I'd actually say, not having a co founder has was a decision that I made that's really helped. The co founder's need for my time and attention and the natural vice versa. Like, that's a competing relationship that needs a lot of energy and time to work as well. And so this time around, I was like, I'm not doing that.
Matt
00:35:03 – 00:35:16
I'm willing to take the risk of missing out on the benefits of a co founder professionally, so that I don't have so that I can not be there when somebody on my team needs me, and I say, no. I'm going to this thing. Mhmm.
Aaron
00:35:16 – 00:35:16
You you
Matt
00:35:16 – 00:35:30
can't say, no. I'm going to this thing to a co founder as easily as your first employees. You know, it's just a different relationship. So that was one big stone that I did not put in the bucket this time around. Seriously consider it.
Matt
00:35:30 – 00:35:45
I know we need help. We need a team, but there are different kinds of team members. So just something to keep in mind, or at least maybe have just such a great understanding with your team members that they are like, we're co founders, but we're not we're we're not married, if you will. Right.
Aaron
00:35:45 – 00:35:47
We're not beholden to each other.
Matt
00:35:47 – 00:36:10
To me sometimes, and that's fine. Right? Yeah. So that's one thing. The other thing is, just going back to that pie chart, I'm now, you know, naturally inclined, even with the obsession the maniacal obsession, I'm naturally inclined to hold onto and take care of the things that we now have because of the change.
Matt
00:36:10 – 00:36:19
So what do I mean? You know, we got a house. This is where we live. I'm invested in it, literally. I'm emotionally invested in it, and it's where we live.
Matt
00:36:19 – 00:36:48
I want to invest in it, and that makes me more present, and it's we all benefit from that. So I'm actually diversified mentally and diversified emotionally a lot more than I was the first time around. So again, the landscape is different, and that really helps because I enjoy investing more broadly, and I can invest more broadly and justify even from a financial standpoint. It's not that double or nothing, triple or nothing situation anymore. Right?
Matt
00:36:49 – 00:37:11
So that's that's another, like, just sort of tailwind that I get to ride. And then the other one is just yes. I I believe like, so yesterday is a good example. I didn't work a whole lot yesterday, probably just a couple hours, which the previous time around would have I would have been so stressed out. It would have been just stroke curve.
Matt
00:37:11 – 00:37:27
Crazy. Like, how can you possibly do that? But then I just replied, I'm like, okay. What did I do though? Well, you know, a podcast episode on indie hackers came out, and I got, you know, I I got the new environment working that we're gonna move to off of Heroku.
Matt
00:37:29 – 00:37:30
That's a pretty good couple hours.
Aaron
00:37:30 – 00:37:31
Pretty big day. Yeah.
Matt
00:37:31 – 00:37:50
From a delivery standpoint. You know? I I crushed it. I I I just crushed it compared to, like, 99% of the American workforce. How many other people can say, like, I told my I shared my story with 70,000 people, and I got a new cloud environment working.
Matt
00:37:50 – 00:37:56
0 percent of the American workforce. That's right. So it's like, that's enough. That's enough. That's enough.
Matt
00:37:56 – 00:38:18
And frankly, it's enough to move the business forward, not every day, but on days like that, let go of like, well, it would also be good if I could ship this feature. It's like, really? Do you have to ship a feature on top of like So like you crush the marketing piece, you made a You move the needle on DevOps. You also have to ship a feature. No, you don't.
Matt
00:38:18 – 00:38:38
Like, that's ridiculous. If you can, if you can have days like you just described 5 times a week, 4 times a week, you're fine. You're fine. You're fine. And this is the lesson that goes back to when you were sick as a kid and you stayed home from school and you suddenly didn't have to go to 8 hours of school and you just did your assignments.
Matt
00:38:38 – 00:38:49
And you were fine. And you were done by like 10:30? Yep. Good for you. Like, you don't have to fill it until 3.
Matt
00:38:49 – 00:39:16
Like, you don't have to fit a month into a week. You just have to do the right things today. And so I actually just aim to get one valuable thing done a day, is my minimum bar for success. Three things is like super achieving, but and I do aim for 3 each day. Usually it's like, hey, if I can do like an hour, 2 hours, 3 hours, and I can do 3, get 3 big things done, like that's now you're talking about what, getting 15 big things done a week?
Matt
00:39:16 – 00:39:20
That's 60 things a month? Yeah. Enormous. It's insane. Right?
Matt
00:39:20 – 00:39:42
So if it's only 30, you're also probably fine. The challenge is you just don't know which 30 things to work on. Exactly. So, get better at that. The time is such a poor, the time is what your family and your personal life wants, but time is actually not what your startup, is not what fuels your startup, actually.
Matt
00:39:42 – 00:39:43
That's correct.
Aaron
00:39:43 – 00:39:47
A fantastic distinction. The time is what your family wants.
Matt
00:39:47 – 00:39:47
Mhmm.
Aaron
00:39:47 – 00:39:58
The time is not the time is not the measure of success in in startup and working. That's right. That is extremely, that is very insightful.
Matt
00:39:58 – 00:39:59
That's the arbitrage.
Aaron
00:39:59 – 00:40:16
You don't you don't go to your family and say, well, I I pushed you on the swing 10 times today. That's enough for today. It's like, no. I wanna lay in the grass and look at the clouds for 4 hours, and it's Right. They they want time, and I want to I want time with them.
Matt
00:40:16 – 00:40:17
Yep.
Aaron
00:40:17 – 00:40:24
But then at work, you just doesn't matter if it takes you an hour or a 100 hours. If you get the thing done, the thing is done.
Matt
00:40:24 – 00:40:42
That's right. Oh. Yep. So be more effective is is the answer to both of those, I think. And And if I send out an investor update and it has there's too many valuable things that got done this month to even list, everyone's fine.
Matt
00:40:43 – 00:40:59
Yeah. Nobody thinks of me as not having achieved the the failure. I there's so much slack in the in the American 40 hour week, And, you know, it was easy for me the first time around to think that I could just I should just fill it. Mhmm. No.
Matt
00:40:59 – 00:41:14
Don't don't fill it. See if you can do a 25 hour or 30 hour work week, and give that time then to others. And I've been doing that a lot more lately, and I'm not saying I'm the greatest at it. And mentally, it's still hard. You know?
Matt
00:41:14 – 00:41:27
Am I thinking about this? But I've, it's it's nice. I've caught myself not thinking about it for periods, and that's what people need. So, yes, relentlessly prioritize. Be effective.
Aaron
00:41:27 – 00:41:43
Yeah. That's that's wonderful. Being able to break that built in, narrative of you have to work 40 hours a week, otherwise you're some sort of, you know, slack, like you're a slacker.
Matt
00:41:43 – 00:42:07
So No, you'll actually do better work if you work fewer hours. You'll, you know I set aside, I think, an hour on Monday this week to write out the, 10 most important things of the week, one thing per day, and then like one other thing each day. Mhmm. And if I look at those and, like, I concentrate, I can get all of those done every day by noon. Now that I'm doing this week lighter than normal on purpose.
Matt
00:42:07 – 00:42:14
Mhmm. But like concentrated effort for deep work for 4 hours is probably enough for you to get done.
Aaron
00:42:15 – 00:42:15
The
Matt
00:42:15 – 00:42:21
2 or 3 valuable things you need to do each day because you're procrastinating and wasting time on Twitter or whatever else anyway, Matt.
Aaron
00:42:22 – 00:42:31
Because you think because you think you have 40 hours and the thing you need to do is only, you know, however many hours. And so you're like, oh, I'll just dork around for a little bit before I get started.
Matt
00:42:31 – 00:42:35
Totally. Totally. Yeah. That's the biggest thing is getting rid of those hobbies.
Aaron
00:42:36 – 00:42:43
Yeah. Well, we're almost out of time, but as the king of the Twitter hot take, I wanted to see if you had any
Matt
00:42:43 – 00:42:45
Oh, boy. Anything you you wanted to grill
Aaron
00:42:45 – 00:42:51
me on or any questions about anything that we're up to or my life personally or anything like that?
Matt
00:42:53 – 00:43:16
Yeah. I I'm I think I agree with what somebody was saying on the Indie Hackers AMA that you did, I guess, yesterday, was it, or the day before? Like, the quality and the creativity of what you are putting out is evidence, and that's really, I'm excited for you. So congrats on that. Thank you.
Matt
00:43:17 – 00:44:01
I I am sort of circling your orbit and like trying to figure out what is this, and I'm not involved in Laravel or PHP or some of the other stuff that we're gonna so it wasn't gonna be evidence of people. Well, now, but I see what you're working on. I'm like, wow, this is this is good stuff. I think my, I don't have much of a hot take other than just, you know, don't make the mistake I made, which was, I built, I spent 2 years building a phenomenal product before I figured out how to get it in the hands of millions of people. And to whatever extent you may feel worried or have reservations that maybe it's not good enough yet for that, like try to, try to repress those because, from what I can tell, your stuff looks amazing.
Matt
00:44:01 – 00:44:03
So, get out there.
Aaron
00:44:03 – 00:44:32
That was a very lukewarm take and I very much appreciate it. Thank you. That's very kind of you to say, but I I thought if you had a hot take at all, it would be in that vein about the time, and I I feel that in my bones. Like, I I do put a lot of myself into the things that I make, and I think that is a good like, that's a good thing. And, like, I put a lot of emotional energy into these things, and that's great.
Aaron
00:44:32 – 00:45:01
It cuts both ways. And the bad side of the cut is at some point, I have to release something knowing that there are still corners that could be rounded. Totally. And so that has been I haven't had to confront that because we've been working on this client project for so long that I've been able to just kinda tinker because I've been waiting on Sean to finish some stuff. Mhmm.
Aaron
00:45:02 – 00:45:37
But now we're at the point where I had my first onboarding call yesterday with, a client, And I was like, this is happening. This is and there there's still a bunch of stuff that I I, you know, I've been integrating with, a first person and have seen all even more rough edges. And now I have the second call yesterday and I'm like, okay, well I gotta get it in his hands by Tuesday. We have an integration meeting set for Tuesday. It's like, man, this is like, it's good for me to have forcing functions like that.
Aaron
00:45:37 – 00:46:01
Yep. And if I were to push this out any further, you could argue, one could argue it's been pushed out way too far, but we do have the make mitigating, you know, client project that's been really good for us. But if I were to push this any farther, it would be intervention time, and somebody would need to say, sorry, bro. I released it on your behalf. So Yeah.
Aaron
00:46:01 – 00:46:09
I I definitely hear that, and I take that to heart. And I am personally like afraid of going too far into that, but that is good to be reminded of that.
Matt
00:46:09 – 00:46:22
Yeah, man. I'm excited for you. Push it out there. They, they, they will make it better for you in ways that you can't imagine. So you're, it deserves them and, you know.
Matt
00:46:22 – 00:46:24
Yeah, exactly. It's a good word.
Aaron
00:46:24 – 00:46:37
Well, thanks for, thanks for coming on. I know this is probably different than your usual fair, but this has been, this has been super on my mind and I knew that I knew that you would have a lot of good insights. So I really, really appreciate you taking the time to do this.
Matt
00:46:37 – 00:46:40
Thank you for the, heartfelt conversation, Aaron.
Aaron
00:46:41 – 00:46:43
Yeah, absolutely. Okay. I'll talk to you soon.
Matt
00:46:43 – 00:46:44
Take care. Bye.
Me

Thanks for reading! My name is Aaron and I write, make videos, and generally try really hard.

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