194: Matt Wensing — Publish Your Juicy Thoughts

Today, I’m talking to Matt Wensing — the founder behind Summit and tweeter of many often controversial things. We talk about bootstrapping a financial SaaS, how to deal with integrations, and when to take funding. Here’s Matt.

00:00:00 An exchange of stories
00:04:54 What’s your strategy?
00:09:31 Writing long-form
00:15:05 Bridging the gap between invention and commercialization.
00:19:56 Creators and salespeople.
00:25:58 How a little bit of cash can change the trajectory of your business.
00:34:34 Bootstrapping is not a shot in the dark
00:41:48 The importance of trust (in the crypto space.)
00:47:55 Centralization has to occur for other people to benefit
00:54:58 How not to leave people behind
00:59:29 How do you look at platform risk from both sides?
00:1:05:06 The nature of platforms

The blog post: https://thebootstrappedfounder.com/matt-wensing-publish-your-juicy-thoughts/
The podcast episode: https://share.transistor.fm/s/f7deea33
The video: https://www.youtube.com/watch?v=2pBYsl1UxeY

You'll find my weekly article on my blog: https://thebootstrappedfounder.com

Podcast: https://thebootstrappedfounder.com/podcast

Newsletter: https://thebootstrappedfounder.com/newsletter

My book Zero to Sold: https://zerotosold.com/

My book The Embedded Entrepreneur: https://embeddedentrepreneur.com/

My course Find your Following: https://findyourfollowing.com

Find me on Twitter: https://twitter.com/arvidkahl/

This interview is sponsored by Acquire.com

Creators & Guests

Host

Arvid Kahl

Empowering founders with kindness. Building in Public. Sold my SaaS FeedbackPanda for life-changing $ in 2019, now sharing my journey & what I learned.

Guest

Matt Wensing 🐙

founder @usesummit, the zero-party marketing data platform. fan of hard work, occasional comedian.

What is The Bootstrapped Founder?

Arvid Kahl talks about starting and bootstrapping businesses, how to build an audience, and how to build in public.

Arvid Kahl
Today, I'm talking to Matt Wensing, the founder behind Summit and Twitter of many often controversial things. We talked about bootstrapping, a SaaS in the financial space, how to deal with integrations, and when to take funding, even as a bootstrapper. Here's Matt.

Matt Wensing
It's amazing. I feel like since we met in person, you've become I mean, you're like a Twitter verse celebrity at this point. It's kinda wild. It's just,

Arvid Kahl
It's bizarre. It's so weird.

Matt Wensing
Well executed

Arvid Kahl
Yeah. And it started on that fateful day that we met. You know, it was honestly it's really with MicroConf Europe that little talk that I gave,with Danielle onstage just about how we set the business, that was the day that I started to have some kind of reputation in the field, you know, credibility, the thing that everybody wants.

Matt Wensing
Yes, yes

Arvid Kahl
From that, I had like, what? 400 Twitter followers at that point, now it looks quite differently.

Matt Wensing
It's incredible. We can have a whole conversation about that because I would love to do the same somehow. But I sort of am only doing it now is like a byproduct of just working on my own stuff. But you've made it a focus, which is working out really well. So that's cool.

Arvid Kahl
Well, let's talk about it. Let's just use this right away. I think for me, it has been a very surprising journey because I did not expect to do this at all. Like when I went to that conference with you. And all the other people there. I barely knew anyone in the field because I was just so focused on building my own business. And then we had the opportunity. I don't know really what happened. I think like, there was a call for papers but for these attendee talks and it was Kevin from SureSwift Capital, the company that actually acquired us, who suggested that we should maybe give a talk about our journey to selling the business. And that was the only reason that I was on that stage with Danielle was because the people who bought our business told us this would be a great opportunity for you guys to, you know, just get in touch with the community around you. And it was and from there on, right?That's how it started for me.

Matt Wensing
There's kind of two things happening or two layers, at least one is you're a good storyteller because you're a founder and most founders are have to be. But the other one is, you shared a story, which is the most dreamed about story in the sphere that we're in. So it's sort of the how I became a knight, kill the dragon and rescue the princess is the story that everybody wants to hear. So you shared the story that everyone wants to hear as a good storytelling the right place at the right time. And you also lived it. So like you said, it wasn't just based on like a fairy tale. It was your actual experience. So you, yeah, you really, the dark flew through all the rings and hit the bullseye is what happened.

Arvid Kahl
I guess for an audience building journey, that definitely was the biggest bang possible in the beginning, right? It's to have both the stage of MicroConf, which is already reputational. And the story of having successfully built and sold a business. I feel very, very lucky. Like for those stars to align and then meeting wonderful people like you and hanging out, you know, like having conversations and understanding that there are more people like me out there, and that I would like to connect further with them, which then led me on this whole path to using Twitter as a platform. But you use Twitter as a platform too, right? I see you have juicy tweets, let's just say that. Like you have interesting sometimes occasionally controlling tweets. I just love that. I love the way you communicate on Twitter. And I wonder if that is just a personality thing with you? Or if there is like, an actual intention of teaching through that method. How has that worked for you? Because you're also are amassing a sizable following there, right?

Matt Wensing
Yeah, it's so my most popular tweet ever was one that I wasn't being as intentional. It was basically, here's the six things that I'm not gonna do this time around starting my second company. And, you know, it wasn't like crazy viral, but 2000 something likes and 1000 something retweets. The second mode, I think I realized when I did that. So first of all, I don't use any tools. I don't draft things 99% of the time. I occasionally I have a thought. I'm like, no, this isn't fully baked. Let me save it as a draft. But I don't schedule things. I don't draft things in that sense. I don't use any tools. And almost every time I publish, it's literally me walking down the street with the dog or you know, sitting at a game or something like that. And I just have a thought. I write it down. I send it and I just do that. And so somebody said well, what's your strategy? I said, I literally just tweet my thoughts. And it's really me going, oh, that's a thought and washing dishes. And then I'll just kind of turn that thought around a few times and go, what's the interesting part of this? Is it this angle? And then like, what's the best way to say this? And then I'll just go. And so there's, it's usually like maybe a two minute or three minute, just moment in my life where I have a thought. I mull it over and then I write it out and hit send. And so the reason that I write so many tweets is literally I guess my brain is just kind of pretty active.

Arvid Kahl
That's right.

Matt Wensing
Yeah, that's the strategy. So I just wanted to share that. And the reason I discovered that sort of non strategy strategy was when I sent that tweet out, that went crazy. I was literally like, in my, you know, I was at home, and it was like off hours, if you will. And I had this thought. I hit send. And I remember looking at my phone a second later, and seeing well, this is getting a lot of likes really fast. That's interesting. And it was just sort of a then only later I discovered like, because I think I had maybe 1500 followers when I first started Tiny Seed back in 2019. And I have over 7000. And I feel like that's a pretty good. That's a pretty good clip. Yeah, and I think the strategy is working and that as well as yours if you just look at the meteoric rise, but it's working, and it works for me. So that's where I'm at.

Arvid Kahl
And I guess that's the whole point, right? Because you attract people that you want to attract with that strategy. And I love this because this strategy is essentially foregoing all kinds of external strategies, and just taking your internal, whatever comes bubbling through your mind, and, you know, sticks with you, that is already, like pre validated. And we should talk about validation because you had a juicy tweet on that too. But you know, it comes up to the surface, and then it's ripe enough to share, obviously, no thought is ever fully done, right? But I see you using Twitter as a thinking tool. Like for some people, nearly an audience building tool. But you think and then you have conversation around it. Is that intentional? Or is it just happening? Because it's happening.

Matt Wensing
So that is intentional because and I tell people I work with this all the time. I don't have an inner monologue. I just I don't know when I'm walking around or what I'm thinking because I think this is the most surprising thing. And I didn't know this until I was in my 30s. So I'm 41 now. But I learned that other people have like this voice that's just talking to them or saying things in their head. And that's how they think, that's how they process things. Since I don't have that, I typically think in I will like see things. I'll dwell on them. I'll just kind of, I'll see a picture. Literally my mind's I'll see a picture and I'll just kind of dwell on it and think about it, but nonverbally. How does it make me feel? What's related to that? It's kind of like this game of what's related. And I tell my daughter this and she was just stunned. She's like, no, no, but like, when you're driving down the street, you know what's going on in your head? Like, I see a stoplight. It's red, the rain is hitting the ground. And I'm not even thinking. I don't understand this at all. The reason I mentioned all this is I use therefore I use external communication to process my thoughts. I have to verbalize in order to process. And I've learned throughout my career that I have to explain this now to people because I will otherwise be in meetings or in conversations with people. And they'll be wandering, they're like, when is he gonna get to the point? And I'll ride. I'll take them on this carousel, you know, all the way around. And then I'll finally go and so therefore, you know, but halfway through, I'll have people go, I think you're on a tangent. And I have to explain to them no, no, I'm just like, I'm just gathering up all my thoughts. And then I'll get them in one place. And what you're seeing on Twitter is basically me going through that journey. And sometimes I'm at the start of it. And sometimes I'm sort of a conclusion and sometimes I'll just do the whole thread where it's like, okay, let's go on this journey together. But when you said is it intentional or not? These thoughts, it's really the only way for me to process and refine my thoughts because otherwise it's all nonverbal.

Arvid Kahl
That makes sense to me. Also, it lends itself wonderfully to recording our long podcasts, right? Because I'm the same way. I'm like in you saying that it just reminded me of the fact that I also have I kind of think I have some sort of voice in my mind, but it's by far not as prevalent as for other people. Like I can get distracted and have these kinds of movies happening in my mind. Like while I walk down the street, but that's not the same. I don't have a narrator. I am kind of the thing that I think about. I feel the same way for me it's not just in tweeting helps me too, but writing long form like forcing myself to kind of take the thought out and then reading it back in. That is how I kind of bridge this gap because I don't always have external people to talk to. So I kind of write it and then read it to myself. Oh, no, that's wrong. It's like look at my own stuff. Do you write? Because I see you tweet, I see you to the podcast. And I see, obviously, you're building a SaaS. So do you have time for that? But do you write long form? Does it help you in any way?

Matt Wensing
I did write long form between startups. So between my last startup in this one, I wrote a series of maybe 5, or let's just say 6 to 10 essays. And they got, they were very helpful for me to really figure out what I should do next. And I gave a few talks at conferences and businesses softwares in place I've done a few talks. So I think talks and long form essays are ways for me to more fully develop ideas and establish expertise on something. And tweeting is my way of like you said, running a SaaS and also publishing. I do have this thought, though. And this works well for me because my memory is also very auditory. So I have my auditory memory is good. So it's funny, I don't hear like the voices. But when I say things out loud or when other people do, I tend to remember them. It means that I can search my tweets. I can go find a tweet because I remember the words I put in it. I remember what I said, you know, a long time ago. And if I did more long form, part of me is thinking, you know, I could probably write a chapter of a book on just by going through and searching for like product strategy and all my tweets cuz I've read like 30,000 tweets or something crazy. I could probably find like 10 or 20 tweets on product strategy and then kind of seed something, you know, which I might do that at some point.

Arvid Kahl
But I guess you're busy enough with Summit as it is, right? I remember when we first met in 2019, late 2019. Some of it was rather new. And you were just like exploring around for me at that point. If I remember correctly, it was a forecasting tool. That's pretty much what it was. And now looking at it, it's this whole platform of, you have like the Summit event language. You invented your own modeling language too, right? Like, all that stuff feels like it has grown quite a bit, which now that you say how you think it's a very iterative process, right? You go from step to step to step to step and then you arrive at the end kind of seems to mirror your journey with the business. How's it going for you over the last couple of years?

Matt Wensing
Yeah, wow, that's incredible! You know, every once in a while somebody says something that's extremely perceptive. And like, you are a perceptive person. But that's a really that's true, what you just said is very true. And I almost wanna just like, recognize that, yes, I iterate on my thoughts. And I see building startups as really a search for is a search for product market fit. As we all say, I do believe that I'm one of those people that thinks that's a real thing. I've experienced it before. It's hard to find but it's a search and therefore it should be iterative. I think that this is often at odds with the perception that I think is most rewarding for people. I think there's a very rewarding perception of the superhero or the superhuman, who knows what to do, does it, and it works. And they never have to go back on their ideas. Everything works the first time. And that's hindsight narrative, right? It's a beautiful thing. And then there's also the people who just raise, you know, $50 million, and can buy a story that supports their ideas at all costs. I am not those. I actually, I really enjoy the journey. I love the search. And I also am very public with it. So with Summit, if you go back to 2019, you can basically read a tweet per day on maybe not every day, but on the business. And I would say it's been a iterative. It's been an iterative quest. And it started with this core modeling language. But then I've basically been we've been wrapping layers around that to get to the point where the end thing is usable by as many people as possible for as much as possible. Just very generic way of saying, we still haven't fully arrived at that touchpoint between, you know, what customers really need and what we provide. But as I was tweeting last week, a couple of things have changed. One is we know who our customers are. And we know what they need and we're willing to give it to them, even if it means doing some amount of services, some amount of customer development, some amount of work to bridge that gap into discover, get the last mile, if you will, between product and market to get that fit dialed in. And I wasn't willing to do that for a couple years because I did not know for sure that we had found our customer. And I think the important distinction that I want to make is I think some founders begin with a product. And they go searching for the right market for it. And I think some people start with the market. And then they go, they try to and then they work with that market to figure out what's the most amazing product I can build for you. And there's a lot of confusion that happens when you cross those advice streams. Because if you take advice from somebody who has their customer figured out and they're just trying to figure out the products, and you put it alongside advice from somebody who's like, I have this invention. I have this amazing product. It does X really, really, it does X 10 times faster than anything else in the world. Who should I sell this to? Those people are like, what are you? What are you talking, you know, this very confused you of course, you sell it to the person that you started out wanting to build something for. And then the person is like, no, I didn't build it. I built it for me. I built it because I wanted to compress something 10 times faster. I did. But now I'm trying to figure out if I should be selling this to like Apple or oil companies or teachers. I don't know who to sell it to. And I am definitely the inventor in search of the market. And I think some people are customer first in search of the product. And the iteration therefore takes on a different shape depending on which direction you're coming from, I think.

Arvid Kahl
Well, that's a great explanation of how you've been going from having this idea, which is a great idea. And I think that the scope of what somebody could do is almost infinite, right? It's a forecasting tool for whatever. You're coming out of forecasting. You know what forecasting is and how forecasting works and how it can be applied to all these different things, from weather to financial markets, there is so much going on. So obviously inventing the tool to be able to serve all of this, that is a great feat. Now making money of that is a whole different game, right?

Matt Wensing
Exactly, exactly. It's closing the gap between invention and commercialization. And there's a whole departments at universities who are called the commercialization group, who helps PhDs and inventors with patents or discoveries figure out what's the commercial application of this thing, right? And I don't consider myself an academic, but I definitely am more of you scratch your own itch type of entrepreneur who is likely to build something because I love it. And then I try to figure out who else loves it and is willing to put the highest, you know, who gets the most value out of it as well, right? And that's been the journey and we started out, this might be helpful for listeners, like if you're taking that approach, what we did was we went from so be very concrete to start, we went from internal operations at company. So we were thinking, the finance department of companies who need to build forecasts and financial models, that was our target customer. That was a sort of ideal customer persona candidate numero uno. That was the obvious choice. And two things change. One is we went from internal to external. We basically said, well, wait a minute. When you're done making this financial model, don't you wanna share it? Don't you wanna give it to others or let them use it? Well, if that's the case, then you probably you have like an audience, you're publishing something. I was like, okay, but that's interesting. That's true internally. But if you're sharing something internally, couldn't you also share it externally? Like couldn't you build and publish a model that is designed for other people to use? Like, yeah, that's true. But wait a minute. Do internal finance, financial operations people generally share what they make with the world? No. Well, who does, right? And so just even that one, I like to think of it as like, turning the Rubik's cube, right? If you're trying to find the market, turning the Rubik's cube and saying what if we go internal to external? You know, is just one dimension you can rotate and flip or invert, right? And then you go well, who are these people that create things? And wait, marketers like to create and publish things. Salespeople are constantly selling and persuading the world to look at their, oh, well, what kind of models do marketers and salespeople make? Well, they don't really call them models, but they call them calculators. They call them ROI, you know, calculators or they call them, you know, reasons you should buy my tool. Or they call them lightweight lead magnets, you know. You look at something like HubSpot and they created their, what's your score for your website? What's your SEO score? It's like, okay, so when marketers make things that are mathematical, they are doing it to publish it for an audience. And so we ended up going on this whole journey of rotating from internal to external. And that's where we're finding fit now, which is really, completely unexpected, but fun. It's like, we built a low code tool for people to publish mathematical apps. And it turns out the most underserved folks for that are not people who live in Excel all day. Surprise, they have Excel and they're really good at it. It's the marketers and the salespeople who have almost no access to engineering resources are very limited. And they themselves don't consider themselves to be very technical oftentimes, unless you're, it could be both, but a lot of them don't. And so they need a low code platform for publishing mathematically rich, little apps more than anyone. Oh, they value it more. And so then you end up in this area, we go, cool. I think we've found people that value what we've made the most. And I think a lot of people just go cross eyed when they think about that, like, why didn't you start with marketers and ask them? What are your hardest problems and then build the product to solve that. It's a fun thought experiment to think if I started with, say, a growth director at a FinTech, who's the kind of person that really loves what we built at this point, and said, tell me about your hardest problems and how can I solve them? I don't think there's many worlds in which we would have started building a modeling language. So it's not actually a two way function. I think if you start on that side, I think you actually end up building very different solutions and applications. And what you tend to do is you tend to focus more on revenue and pain points sooner, I think. And I'll say it here is kind of this would normally be a tweets, but this is an example of kind of thing. I do think that the indie hacker and bootstrapping crowd, I think tends to index more heavily on find the customer and build something to solve their problem because it is a faster path to revenue. Because you literally have somebody who's sitting there telling you that they have this pain and if you solve it, they'll pay you for it. Versus I'm gonna build something that I love and think is really cool. Let's see if anybody will pay me for this, right? It's much more risky and kind of at odds with the bootstrapping approach of I need money tomorrow. So what do you need? I'll build it, right?

Arvid Kahl
What do you have done this as well, if Tiny Seed hadn't been part of your journey that particular way?

Matt Wensing
No, I don't think so. In fact, but actually, let's do this. Since we have a moment, let's see that apart really quick. So when I raise money from Tiny Seed, I was a solo entrepreneur, second time founder, who was building a what I thought was kind of a $50 a month, more turnkey SaaS lifestyle business. And I was trying to sell it to founders because I live this problem. And I just figured, if this can make a few $100,000 a year, I'm happy, right? And this will work. And that was actually what I approached Tiny Seed with and I think, you know, they knew me enough. And they knew what I was working on. Really the going deeper, the let's invent a language and let's go deeper was really enabled pi, pursuing that and then hitting a wall and going, okay, I've got a couple people paying me a little bit of money. They want some integrations. I could do that. But is that all this can be? Could this be more powerful? Is that flexible enough? And what I realized was that some users would be happy. But then in my customer conversations, some users were like, what you have is cool, but I really needed to be more flexible. And so what Tiny Seed's money allowed me to do is pursue the first I would say horizon of customers, which were, I'll give you $49 a month, if you can just tell me what my revenues gonna be next year. That's neat. I like that. I need that. The additional funding that we raised along the way allowed us to go how do we expand the market and go after a broader set of people, which is sort of how the story goes where you sort of get, you saturate what you think your opportunity is. And to be clear, we didn't build it up to be a saturated thing where we had 1000s of customers paying us $49 a month. We kind of got a few and realized, this probably won't grow to the scale that is really exciting for me personally. So I need to grow the market. And that's where, you know, that's where Tiny Seed's money kind of ran out and I went, okay, so now I can either continue to build this into a lifestyle business, which might make a million dollars one day, maybe, or I can raise more money and try to grow the market to, or improve the product so that these other people who are kind of like, on the fence would also subscribe.

Arvid Kahl
It's an interesting example of how just a little bit of cash invested into a business that is at that stage can make a whole lot of difference, just for the trajectory of what you experiment with how comfortable you feel, also building out the thing you have and then pivoting. One thing I would like to ask here at this point, are any of these $50 customers still with you? Or did you pivot away from them?

Matt Wensing
One, let's see, one of them was there. We fired all of our customers in a very nice way. That's my horrible way of saying it. But we basically told them the product is going away. Yes, exactly. The product is going away. We're rebuilding it, we'd love for you to subscribe to the new thing. And we do have one paying customer who was a customer then who's a customer now. And that's satisfying, meaning he stayed for the whole journey. Maybe skip the middle part a little bit. But, yeah, a little bit, but the product has gotten so much more horizontal. And externalize that most of those people, they might still be experimenting with it, but they are no longer the focus.

Arvid Kahl
Okay. That's cool. It's, I think one of the fears that every founder has is that if you make a change to your product, do I lose all my cash? Do I lose all my revenue, right? That's why I'm saying like money helps like having external money a little bit. You don't have to have millions to do this, right? You just have to know that for a couple of months, you can experiment a little bit longer, right? It doesn't have to be the moonshot kind of money. Did you feel different like, in terms of the risk you could take with your business when that Tiny Seeds, not just the money, but also the mentor network came in?

Matt Wensing
I did. Well, so I have a very different view of risk than many. So at the end of the day, I truly believe that most of us that can build products from scratch and start companies from nothing. We're either I understand we're incredibly non employable in a way. But I also believe that most of us, and now you know, economy allowing can find work, if we need to. We have skills that are monetizable, let's put it that way. So I never really feared a disastrous situation where I wouldn't be able to provide for my needs or my family's needs, it was never that. So with the Tiny Seed money really let me do is say, okay, I can I look at raising money as investing down into something in order to increase the upside. So it's meant to be put towards things that are creating leverage for you, right? So I didn't want to just take the money and make the thing I had 10% better. I wanted to take the money and make the thing I had potentially 10 times better. And so I took on a lot more risk because I had the money, but I also see that money as venture capital, it's really there. So that you will take some extra risk, because if you don't, you probably should have taken out a loan or something instead, right? And that's where I'm at. So I would, if I'm gonna raise money by selling equity, I need to do something that's increasing the value of the business significantly. Otherwise, I shouldn't have raised that money.

Arvid Kahl
Does that sound scary to me, you know. That just talking to you as a founder, from my perspective having not raised intentionally, like I love to have the control also. I knew that there were limitations in not having that money available. You have to make month over month kind of choices, but it felt the choices that I make that are actually bringing in more revenue while they are good, right? I don't need to kind of stop making these choices. I'm just gonna keep continuing growing my business. But I see, obviously, that if you have this perspective of risk, in particular, if you look at risk that way and see that as VC money, which in my mind was always millions of dollars, but you're right. It could just be a couple of 10s of 1000s, right? That is also in venture capital because you can go on the new venture, just reframing my own perspective with missy here. So thanks a lot for mentioning that. That's really cool.

Matt Wensing
Yeah, I also agree that if you know, angel investors and friends, if you will, are and I think Tiny Seed is more friendly to you getting an outcome that is not, it's literally not about all or nothing, it's supposed to be a take some risk. But nothing's wrong with building just a great profitable software business because those are valuable on the market. You can get a multiple of revenue for those because they are high margin. And they tend to stick around. The thought about it being venture capital, though, for me is what it allows you to do. I thought about that. So for those that don't know, I did bootstrap my first company for five years. So I know what that's like, I also then we didn't succeed at raising a series A for my first company. So we had to go back into effectively self funding mode, we cut, you know, reduced salaries, we went through a lot of pain. And then we ended up being profitable again, on the other side. I've been through the whole journey. And with this time around, I experimented a little bit and then I sort of immediately raised capital. And the reason is, I just want to be able to work on things that require a higher wager. I think you get to the point where you're like, okay, to really get a bigger outcome, you have to place a larger bet. And if your appetite for betting is limited to one months runway or next week's paycheck, or maybe even just and I can spend $500 on Google ads and see how it goes, you eventually get to the point where you say, okay, I've got a lot of market feedback and signal that if we build this mobile app or if we do this thing, you know, I've done the mock ups, I've done the tests, I've done the landing pages, I've done the interviews, done my homework. I'm not doing this blind. But at the end of the day, they still need a product. But you can't do it because you need to pay somebody $10,000, $20,000 to build that thing finally. That's very painful, like I've been there too where you go, I actually truly believe I know what the market wants, but I don't have the resources to proactively invest in that. And it means that I kind of have to let somebody else seize that opportunity, you know, and that's fine. No harm done. Other than maybe a little bit of regret of going I wish that had been us or I wish we could have seize that because we saw it. And we knew it was there, but we just couldn't, we couldn't take a risk. And that's, it is what it is. But I really have a hard time. Like that creates some regret for me. I've actually had to see that happen in my past and kind of this time around, I wanted to be able to know that I left it all in the field, as they say or whatever expression that, you know, I did try to, I place all the bets that I need to place as smartly as I could. And even if none of them pay off, at least I wasn't constrained by the inability to invest in testing that, you know. You can afford more tests when you're funded. That's really how simple it is. And if you can do that with customer cash and profits, and sort of you actually can fund all of your tests and ideas just purely based on revenue. I mean, congratulations!

Arvid Kahl
Good for you.

Matt Wensing
Good for you! You know, but my experience has been not having funding means that you there's a lot of stuff that's below the line and you just go that's unfortunate because I think if we just had a little bit of money, we could really knock this out of the park, you know, that's to be able to do.

Arvid Kahl
You're definitely slower to do these things because it just takes more capital coming into the business which if you are bootstrapped and revenue focused and it just takes a couple months to grow it to that point or years even, right? So if you're competing in a red ocean that where people have a lot of money to put towards these things, that is a drawback. If you're not if you're in a less red bluish ocean, then that's may be fine but then you have the whole problem if you know have to figure out what actually to build for people to keep, you know, sustaining your business with revenue. Problems either way, but thanks for sharing this because I feel as in my own experience, and I think many experience of the founders out there that are bootstrapping that are putting their own money into a business, they are super scared to lose it, right? That's why they wanna that's why they start with the market and figuring out their problems, and then solving them with a very clearly budgetable solution that is not a moonshot, not a shot in the dark, not a thing that they wanna build, but a thing that other people need. So they can immediately monetize it. And, you know, you said earlier how Tiny Seed allows you to do these little things and saturate the one idea and then go to the next one. That sounds remarkably like Rob Walling stair stepping approach, which is unsurprising because, you know, he's kind of the guy. So it allows you to go to that next step, have the security to go to the next step and be a bit more adventurous, right? Not fear for your life because particularly living in places like the states where you know, money or insurance and health are all kinda extremely expensive and then doing risky stuff. I mean, I remember us talking at some point and you mentioning having being in financial hardship too like building things because there was no cash and your house was you have to pay a mortgage, and you have to bring the kids like through college and all that kind of stuff. That frightens me even to think about. Do you have any ideas like how you could de risk that stuff as a founder who doesn't necessarily have the access to capital or access to even to the reputation that you had to get into Tiny Seed?

Matt Wensing
Yeah, no. Well, I lived that. So when I built my first company, like I said, we bootstrapped for the first five years. And I wanna be really clear what bootstrapping meant was nights and weekends to start. I had a software developer job. I had ideas. I listened to podcasts. I started working on it. I also had a one year old. So time was limited, which meant sleep was the sleeping time with the family sacrifice both so it's very expensive. You end up spending capital that is physical and emotional, instead of financial because you need the financial capital from your job to you can't sacrifice that, right? And there's no adventurous person saying, go ahead, spend my capital to discover something great, right? There isn't that person equation. So that to me is the hardest thing to solve. Because I agree nobody's truly bootstrapping. And that's another thing I wanna say. I went to a great college. I had parents who paid for it. I graduated very little debt. I graduated early to avoid some of that debt. But then I also had a job with no health insurance when we had our first child. I had to go find a job that did. I was in and out of jobs, depending on how my first startup was doing, oh, I can make enough to pay the bills. Let me quit for a while and then go back. And then oh, we have another kid on the way. Let me go find a stable thing again. And so it was very turbulent. And obviously, there's a whole nother series of episodes you could talk about, you know, with someone like Sherry Walling or others about the psychology and relationships and family and all of that, that you have to maintain. But purely from a hustle standpoint, the only thing, the thing I did was I said, what do I have that I can sort of burn that isn't money, right? That can somehow start a snowball here. I'm trying to get you into mixed metaphors. I got to get something started. And what I discovered was I was pretty good at pitching. And I was pretty good at storytelling and speaking. So I started to apply to pitch contests, having no experience fundraising and having no experience public speaking or pitching like that. But what I knew I wanted to do was I wanted to grow my network and I wanted to get in front of more people. And I just believe that social capital was something that I could accumulate, even with no financial capital. And the only way I could do that was to do what other people weren't willing to do, which is put myself out there, speak publicly and travel a little bit. So for $150 plane ticket to Atlanta, I would go I would fly from Florida, where I was starting this company, spent $150 in plane ticket go up, maybe spend $100 in the cheapest hotel I could find, you know, safely. Go give a spend all day at this pitch contest, present a pitch you know, get fifth place out of 20 doesn't even really matter. Maybe an honorable mention or something. But then I would spend a couple hours talking to people and go oh, where do you work? Where do you work? Who are you? What are you doing? And then I would go back and it'd be like, well have that go. Well, okay, so I have a lot more business cards back in the day and I have a lot more email addresses I could email. And now people know who I am. And they're talking some somebody out there is talking about this thing. And I did a lot of those. And it was the kindling for my career, essentially. Because what I started to learn then was, as you said, capital isn't acquired through. I hate to say it's not acquired through just hard work. It's acquired through exposure and social capital because those things create trust. And trust is actually the currency of the whole economy, who you know, who gets money, and when, and why and all of that, even your company getting acquired. If you're not putting yourself out there, you're missing out in a whole part of the equation. So being super scrappy and essentially making ends meet just barely, and credit card money, the only thing I had left to burn was my time and energy and my ego to basically put myself out there and start to speak. And that actually led me to being able to fundraise for the first time. So I pitched. I also ended up pitching over 100 investors for the first money that I raised. And learning by fire how to effectively get an investor to say yes and that changed my career. But it started with this dude nobody's ever heard of being willing to just put himself out there because that was the only really capital as I keep saying that I had. Everything else was unavailable to me.

Arvid Kahl
That was awesome. That is such a interesting strategy to start out with that isn't so focused on building the right things that are not money in the world that is essentially about money at a later point. Any kind of economic endeavor is at least measured in money at some point. But yeah, social capital and reputational. Just, yeah, just a reputation for being a person people can trust. And then over time, start trusting, that is genius. And I would like to talk to you about trust because I feel we live in a world like it's on social media in particular, but also in diverse industries that we are and that are showing that trust is important by its absence. I would like to talk to you about the shitshow that is weaponry and crypto. Like at this point, because I'm just thinking, we are constantly surrounded by that stuff. And what is your perspective on this? At being somebody who is in predictions and who understands like industries and how they move and forecasts that people have given years ago about boom, that will be crypto and NFTs and all that weird Web3 stuff. What is your perspective?

Matt Wensing
Yeah. So I wanna be fairly harsh, correctly harsher myself to say, you know, I don't see all things at a time. There was definitely a period in 2019, 2020 where I was pretty excited about crypto and Web3 hadn't been coined yet. We weren't really coining Web3, was just etherium and crypto. And that's because of the co founder of my first company had always been telling me that I should get involved with it. And once I had my first exit meeting, my first step was acquired, I had a little bit of money to start experimenting with alternative assets. And I started to try it and you literally just dumb luck. It was also a great year for crypto. So I started to get drawn into the atmosphere of it and start to think, kay, what this is pretty exciting. This is pretty cool. And who doesn't like making money? It feels great to see your net worth going up literally by the minute, depending on which minute you check, but generally up into the right.

Arvid Kahl
Most of the time

Matt Wensing
Most of the time that year. And I but having some background and experience with being burned enough, I frankly being hurt enough. If you take lessons from being burned and hurt in these places, it does two things. One, is it can make you very close and cynical to new opportunities, which is a bad thing. But those antibodies are still there to question things. And just be willing to be a little bit more rigorous and skeptical of human nature and what's going on here. And so I do think that you have this incredible technology, which is weakly understood by most people. And I think that anytime there's something new that people are in a frenzy about it always pays to try to become an expert in it on a deeper, fundamental level like, do you really understand what this is? Kind of the Warren Buffett approach of like, if I don't understand a business at its core, I don't want to invest, is important. That is a level of not trusting, but is required. That's what is due diligence. So this is actually maybe a different way of looking at it. Due diligence is a process that people are supposed to apply in a situation where trust doesn't get them all the way there, right? It's, hey, Arvid, I really appreciate that you want to invest in Summit. I think that you're probably everything's fine. But I'm gonna, but because I only met you twice, I'm gonna ask a few questions, right? That's healthy and it's normal, and nobody should be offended by that. But emotions are extremely hackable. And emotions are extremely potent. And if you've ever gotten a phone call from somebody that says, your computer's being hacked, right now. I need you to go to this website, you know. There's always gonna be a group of people who know how to socially engineer things to hurt other people. Sadly, that's the world we're in. And so obviously, hindsight being 2020. This is what ended up happening. And I think that's the always going to be the case number of humans that are trying to take advantage and exploit a good thing for harm of others. I think the other part of it, though, is understanding that we are living this is sort of my more meta comment. I think we're living in a time that's stress testing, centralization versus decentralization. And this is not just with currency, this is with countries. This is what populism and federalism. This is with, you know, states and United States, States of America, United States of America. This is happening everywhere. And I think that we are currently the pendulum has swung. Well, at least it did up until maybe two weeks ago, swung very heavily towards decentralization is obviously the answer because centralization has bred the likes of Facebook and Twitter and Instagram, the surveillance state and all of these things. True. But it's also the reason we have the United States of America. It's also the reason that we have, you know, groups of people MicroConf has attended, you know, conferences, where there's 1000s of people there, which you'd like it to just be all completely scattered so that we don't have that. There's benefits of centralization. And I think what commentators like Ben Thompson of Stratechery have said that I really enjoy is, at the end of the day, all decentralization still need somebody to centralize the benefits for the average person, right? I think centralization has to occur on some level for other people to benefit. And that centralization point, that aggregation point that user interface, that layer will always be a target for exploitation or hacks or whatever. And that's a trade off. In other words, we can only have a President if we have a national election. Therefore, we have to have a national election day and machines that exposes us to a great vulnerability. But the only alternative is to not have a orchestrated sort of national identity, right? So if you want that, we have to have that. And I think the same thing is happening in Web3 and crypto, where people are going, we want the world to participate. If you want the world to participate, then you have to have things like open sea and FTX and Coinbase. Because they make it accessible for everyone else to participate. And I think there's always going to be that fantasy struggle where people go, but it's not that hard to just memorize your seed phrase and put it in a safe and whatever. Excuse me, have you do you not have a family member who called you for tech support? Who has called you for tech support? And I think part of me really empathizes with those folks because why? I am the inventor at my core as well. I love a new technology that can be applied. And where do I struggle? It's often the adoption gap where I go for the average person to use this, which I need to build this vision that I have for a big company. I actually have to make this usable for normal everyday folks. Yeah, okay. Well, then you gotta build what they want and they don't wanna go to seven places. And I think the pendulum that swings back and you end up with people going, I love how easy it is to trade crypto on Coinbase. The Web3 folks like, ah, that's not the vision that we had. You're creating this thing. And you go, yeah, but that's the only, my mother in law needs to be able to reset her crypto password by calling a 1800 number. It just is what she needs. And I'm sorry, that wrecks your purity mindset. But that's how you create apple. That's how you create Google. That's how you create Facebook. And I think what people are seeing right now in Web3 is sort of this, the denial phase of, but we weren't supposed to create banks without regulation. We were supposed to create the decentralized banking infrastructure of the future. And then you're like, that's fine. But the average person is still trying to get their paycheck in advance from their bank, and they need their password reset. That's where we are.

Arvid Kahl
It surprises me that people forget that there needs to be this transitionary period too. Like, when people come from one way and then go, you know, into the new technology. I mean, I wish I knew more about how cars happened. You know, not just how the technology around cars happened. I understand like, there were horses and buggies and then people mechanized and automated that or energized the buggy. But I would like to actually know more about the societal transition at that point or trains right? Where people were afraid of trains to run faster than the speed of a human or a horse? Because they thought their innards would be spilling out that kind of stuff like, you have to address that, right? It's not oh, yeah, train. Use trains. Nobody would would do that. I feel the same with any industry.

Matt Wensing
Exactly. I actually, that's the other. I'm glad you mentioned that. Because so I do a lot of road tripping in United States. I love getting out in the open road and driving around. Because I think, if you really want to answer that question or think about that, go drive, don't just fly over places. Don't just go from Seattle, San Francisco, and I'm picking up places now. But Austin, you know, drive from Austin to San Francisco. And understand that I understand, you know, sure. Maybe only 30% or 50% of the world's population is in between these two. But what decade are they living in, really? And when you mentioned things like the automobile, they're still dealing with the repercussions of highways being built in the 1950s and 60s that have caused their towns to collapse. And that's the technology transition they're still going through as a group of people. And now you're saying we're just gonna drop a Bitcoin ATM on the corner? And like, that's how you're gonna, I don't, I think what's happening is, society is actually I think the word is descending. I think what you're seeing is, I think a smaller and smaller portion of people are living in some era or maybe on the bleeding edge. And that group of people is getting smaller and smaller. And I think it's like a comet that the tail of the comment is the 98% or 99.9% of people who are actually living in some technological age that's way in the past for those other people, you know. They're still living in the 80s or the 90s. Was it, half of rural America doesn't have high speed internet yet. So that if you wanna talk about true technological advancements for society at large, explain to me how you're going to help those folks catch up to you who is dropping acronyms on a Twitter space that I consider myself cutting edge and I have no idea what you're talking about, you know. You have no idea. You lost me, right? And I'm trying those people you know, they'll never get it and I guess to conclude my own thought like, what you can end up with this sort of like, from what I understand places like India, where they actually skipped landline telecom technology and they went straight to cell phones being the dominant paradigm. I think that perhaps one day, Web3, crypto, etc. Could you somehow AirDrop no pun intended, like that new invention on to people and they skip wire transfers and Robin Hood and a bunch of other stuff that's like maybe in between, they basically go from the 90s to the 2030s in a jump, maybe. But if that does happen, there's gonna be a lot of pain that falls out of that because you don't just skip whole eras without, you know, some kind of shock, right?

Arvid Kahl
Yeah, yeah, transitions are always important just for people to not be left behind. I think that's important.

Matt Wensing
Yeah

Arvid Kahl
And I'm really glad you said that like this, that you need an intermediary. You need some kind of centralization because I see this also in the creator economy field a lot. That there are so many creators out there doing their thing. And there are a lot of people who wanna consume whatever they wanna see, like if it's movies or music or really thinking tweets that we put out all day. It's hard to catch up with a real time medium in the first place. It's hard to just stay on top of things, which is why there are curators all over the

Matt Wensing
Duration

Arvid Kahl
We call them influencers. We have no problem. And we might ourselves be that for some people, right? You and I

Matt Wensing
Yes

Arvid Kahl
At this point.

Matt Wensing
Yes

Arvid Kahl
Some people will listen to us when we talk about things or when we give recommendations, right? That already is a curation of attention and focus. So if that is already happening in the field where people are self proclaimed cutting edge, I consider myself that too. And I have the same problems understanding certain acronyms on certain Twitter spaces. How much worse must it be for people who are not part of this community not even interested in the things that this community is talking about, right? How are they supposed to be part of this technological revolution, particularly in a democracy. They have the problem that people can just be told what to think or what to do. If you look at China, which is a great example that you just gave, like with the leap in technology. When we went there in 2018. all we saw on the streets were electric cars and people paying for street food with WeChat pay. Like they have the street food guy who had just this little card that wasn't like one of his only possessions, you would go there and you couldn't pay in cash because he would only take WeChat pay, which was bizarre. Like it was bizarre, particularly as a European who is very cash centric back then, right? We were still living in Germany, which doesn't really have this credit card culture. We kind of skip that. It's super weird. It's like every part of the globe skipped certain different parts of the technology space.

Matt Wensing
Yeah

Arvid Kahl
And we went to China, and we saw everybody, even like the farmers from the hinterlands essentially using WeChat Pay and WeChat to communicate with each other. And this is such a bizarre thing to see that how in a country like that, where it can be done kind of put into people's lives from the top, there it works. But in the country where people have a lot of liberty to choose what they wanna participate in and whatnot, you have a way bigger spectrum of how far people have transitioned already. So if you're building a business in China, you probably have different kind of regulatory things to think about than if you do it in the States or in Canada, where I live at this point. And if you wanna build a global business, now, all of a sudden, you have to kind of juggle both of these, yay!

Matt Wensing
Yes, yeah. No, you hit on a great point. I mean, this is I studied a little bit of Russian history in school. It was kind of my major, but in some of these cultures, just going back today, you will adopt this new tech paradigm or technology could be a state centralized decision. And therefore adoption is 100%, right?

Arvid Kahl
Guaranteed

Matt Wensing
Guaranteed. Let's actually take that out of politics, and just even apply to mobile technology for a second. One of the things that mobile developers, from what I understand, having worked with a few would really enjoy about Apple is the market adoption of a new iOS version is almost 90 something percent within 30 days of an existing. Try that an Android where it's more of a democracy. You think decentralization is great until you try to push an update. And then you realize that this means I now have 7.9 million customers and 47 different states or versions of things to deal with. What I really want as a developer is rails and standards and platforms that I can count on to say, yes, we know that only 1% of our users when they hard press on this icon won't get the new menu that we just created. But within 30 days, it'll be 100% because Apple is pushing this update out on everyone. There's always gonna be somebody who's like, I can't believe Apple made me download this update. I don't want to do that. But look at how progress gets distributed to most people. You can't ignore trade offs, right? And that's the trade off we're dealing with.

Arvid Kahl
Well, then, as somebody who's building a platform yourself, how do you look at platform risk? You know, because I look at platform risk, like going on Twitter, potentially losing my audience if there is another weird mishap up in that particular business or building something on top of Ruby on Rails, and then it gets discontinued for some reason. You know, platform risk exists and on many different levels. Since you're building one yourself, like, how do you look at this from both kind of sides?

Matt Wensing
Yeah, it's. So I think the better way to look at it is how many platforms are you going to be building on, not are you going to build on a platform because it turtles all the way down, as they say, and, you know, we're on AWS. So if you start counting the platforms we're on. And heaven forbid, you look at software dependencies and open source and all these things. There's a lot of packages I need people to keep maintaining, ideally. So platform risk, I think, if you unpack that, it's kind of terrifying. But let's not unpack it beyond the AWS level for a second. So choosing your host is a big, it's probably the first level of decision that people need to make. And I've talked to some founders and I chose this third or fourth runner up to the big three. Not I mean, understand the choices you're making. But even beyond like that level, the CTO of my first company, I always respected his decision to not use specific features of AWS, like user this this this function tool program thing. Does everybody else have the equivalent thing? That's the first decision you're even making before you even get farther down the path. And it's amazing how many folks will go, yeah, I'm gonna use that as like, okay, you're probably locked in then. And that maybe that's okay, maybe that's okay. But you've already now made at least one platform choice, then you kind of, you have to just keep layering, essentially. And you go. If I'm building on, so here's then the real success sort of fetish level. At the top, you need to understand if the platform you're building on is a platform or an aggregator meaning, they're in it for themselves. You are merely a nice little petri dish for them to discover what people really want. And when you do that service for them, they're going to discontinue the API, they're going to say that's no longer their terms of service. And they're gonna bundle it into their core products because they're not a platform. Bill Gates had this great response to Mark Zuckerberg or Facebook at one point. Mark Zuckerberg was like, oh, we're this platform, this platform. Bill Gates, basically called BS on that and said, that's completely not true. He said a platform is measured by the economic value of the people building on it being greater than the economic value of the platform itself. Windows is a platform. Facebook is not a platform. It is a social media network. It's making a ton of money off advertising. And it's letting game developers build nice little things on top of it to attract more people to its core business. And if they ever figure out how to make a better game or they figure out that gaming isn't really great for them, they're just gonna turn it off. And that's what they do. So if you really believe that this is a platform, great, go for it. But the receipts on the platform being a true platform is what is the economic value of all the companies building on top of it. So Shopify is a platform. I'm not convinced that every company that starts with S is a platform. I'm not convinced that, you know, Amazon is a platform. The number of AWS economic value is less than all the counties built on it, obviously. But that's a big litmus test. And that's why when I look at things like Notion, Stripe, a few others where they go, we have apps now. Intercom, you know, sure they have apps, you can build apps. But until the value of intercoms apps exceeds intercom itself, intercom is less beholden to the apps than they are to their own mission. And they might just decide that that cool feature you that cool app you built is actually a feature. And if you won't allow yourself to be acquired, they're just going to build it themselves, right? That's an aggregator. They wanna aggregate everyone's attention and all of the money. A platform is unselfish endeavor, if you will, to lift up the infrastructure for everyone else. And so I think it gets complicated too because even some of these businesses like Stripe, for example. They have API's that are platform, use our credit card processing API to process credit cards. That smells walks and quacks like a platform to me. So I'm gonna call it a platform. Definitely economic value exceeds they're just skimming. People get to something like Stripe apps where it's like build a Stripe app for our dashboard for our customers. So they can see their MRR in a new and exciting way. I don't know because that seems pretty. Seems pretty kind of ancillary. And

Arvid Kahl
Even the tax calculation they did, right? Like that kind of

Matt Wensing
That's a perfect example. Yeah. If stripe were truly a platform, they would have said, we're so glad that a tax calculation company has built tax calculations on Stripe. Everyone should use that. Just like Microsoft would say, everybody should buy photoshop. It's Windows compatible, right? It's never in Microsoft's interest. Rarely is it in their interest to go by Adobe. Or make that a part of like, we have paints, but it's not really competing, right?

Arvid Kahl
It's awesome, though. Yeah

Matt Wensing
It's awesome, though. But that's the idea. You know, true platforms are saying how many gaming companies can we help create? How many tax caches can we can create? I think platforms are this kind of more outwardly focused and platform risk gets created when founders build on companies that aren't actually platforms. That's the biggest advice I would give.

Arvid Kahl
I like that. It's a really great distinction between something that fosters innovation and something that absorbs innovation. These are

Matt Wensing
Yes

Arvid Kahl
Very distinct ways of like dealing with your clients or customers, right? If they, yeah, if you wanna empower them, or if you want to be empowered by them.

Matt Wensing
That's right.

Arvid Kahl
Very, very interesting. Wow. I think we're slightly out of time at this point. But man,

Matt Wensing
All good. Thank you.

Arvid Kahl
This could have went on for a couple more hours. I didn't get through like one quarter of the things I wanted to talk to you about. I guess we better have a secondary conversation here at some point. I'm extremely thankful for your sharing your thoughts here. And I love the way you approach thinking about something verbally. I just, it's resonates with me a lot because you take me on this little journey. And the journey ends up where I wanted to end up that couldn't ask for more. Thank you so much, Matt for an hour and a couple minutes of a wonderful, wonderful conversation. If people would like to hear you talk more or read what you have to say, where do you want them to go?

Matt Wensing
Yeah, go ahead and follow me on Twitter @mattwensing. And I would love to engage with anyone there. That's my favorite place to be when I'm not just walk around the real world.

Arvid Kahl
Thanks so much for being on. I love your work. Love your thoughts. And I'm really, really grateful that you spent some time with me today. Thanks.

Matt Wensing
Thank you, Arvid! Thank you!

Arvid Kahl
And that's it for today. Thank you for listening to the Bootstrapped Founder. You can find me on Twitter @arvidkahl. You'll find my books and my Twitter course there as well. If you wanna support me and the show, please subscribe to my YouTube channel. Get the podcast in your podcast player of choice and leave a rating and a review by going to (http://ratethispodcast.com/founder). Any of this will help the show. So thank you very much for listening and have a wonderful day. Bye bye