Anchored in Ambition: Tyler King on Crafting SaaS Businesses that Last

00:00:02:10 - 00:00:29:15

Ben Hillman

Picture this a master shipbuilder crafting a vessel meant for the tumultuous seas while others rushed to build rafts and boats that may offer immediate short lived journeys. This artisan takes their time selecting the finest woods, ensuring every joint is sealed and every sale meticulously designed. The goal isn't just to navigate calm waters, but to endure the fiercest storms and be passed down from generation to generation.

00:00:29:17 - 00:00:55:20

Ben Hillman

Becoming an emblem of resilience and longevity. In the realm of B2B SaaS, there's a similar ocean of uncertainty. Waves of trends come crashing and technological tempests test the metal of many ventures. While many software companies rush to launch, seeking a quick voyage to profitability and perhaps even an expedient sale, there's unparalleled value in building a ship, a business meant to last.

00:00:56:00 - 00:01:26:04

Ben Hillman

In this landscape, durability isn't just about survival. It's about creating lasting legacies, impacting countless businesses and setting standards in the industry. Steering one such indomitable ship in the vast sea of SaaS is Tyler King, CEO and co-founder of Less Annoying CRM. Much like our master shipbuilder, Tyler isn't here for the ephemeral thrills. He's committed to crafting a product in a company designed for longevity with a unique perspective on sustainability in the software realm.

00:01:26:06 - 00:01:56:19

Ben Hillman

King has created insights not just from sailing smoothly, but from weathering the storms, making him the beacon many SaaS founders turn their companies towards. Join us as Tyler King dives deep into the intricacies of building a software company anchored in long term visions and sustained profitability. And if you find yourself wanting more navigational insights, be sure to tune into Tyler's own podcast, Startup to Last, which delves into the art and science of building companies, not just for the sake of selling, but truly lasting.

00:01:56:21 - 00:02:16:04

Ben Hillman

From Paddle, it's Protect the Hustle, where we explore the truth behind the strategy and tactics of B2B SaaS growth to make you an outstanding operator. I'm Ben Hillman and on today's episode, Tyler King speaks with Paddles. Andrew DAVIES about building a profitable software business meant to last. After you finish the episode, check out the show notes for a field guide from today's episode.

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Ben Hillman

Then, while you're leaving your five star review of the podcast, tell us what resonated most about our guests Advice.

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Tyler King

My name is Tyler King. I'm the co-founder and CEO of Listening Serum. My background is kind of in product development and design. My co-founder, my brother, also a technical founder. And yeah, listening serum is exactly what it sounds like. Basically, we started back in 2009. It's a long time ago now. And the basic process was my old boss put me in charge of signing up for Salesforce.

00:02:46:12 - 00:03:06:14

Tyler King

I couldn't figure it out despite having a degree in computer science. And that was kind of the light bulb moment of like, Well, what do people do who don't have an IT team, who don't really want to build all these complex automations and workflows, and they just need something simple to keep their data in. So for the last 14 years, we've just been serving very, very small businesses and kind of traditional industries.

00:03:06:14 - 00:03:16:20

Tyler King

Not when I say small business, I don't mean tech startup, I mean like insurance agent. And we've just kind of been grown from there and yeah, we got a little over 25,000 users now and kind of chugging along.

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Andrew Davies

So I know you're a building public man. So tell us a bit more about where we currently at on your revenue, your employee count, how things are going. Yeah, I.

00:03:23:15 - 00:03:42:02

Tyler King

Think we're right around 3.8 million are right now. We have 20 employees counting myself. Yeah, I'd say we're kind of in a even though we're small, we're kind of in a mature phase in terms of like we are growing. We are not growing fast. You know, in the early stages, everything you do is temporary. Everything is This is going to break six months from now.

00:03:42:02 - 00:03:48:16

Tyler King

So let's start for the next phase. And I think where we are right now is more like this is the phase we're in for now and we're kind of settling into it.

00:03:48:17 - 00:04:02:02

Andrew Davies

Talk me through some of those company phases. When you say the phase we're in now, because this is so this is a 14 year long journey. So far, not a long time in any industry. It's feels like a lifetime in SaaS. Take me through, you know, the stages. You've seen this company mature through.

00:04:02:03 - 00:04:15:01

Tyler King

Yeah. I mean, when we started, it was it was just my brother and I, and I don't even think we wanted to run a company. We just wanted to build a product. You know, you don't have any customers, you don't have any employees. You can just do whatever you want, set your own schedule. It's kind of ultimate freedom, which is great.

00:04:15:01 - 00:04:32:17

Tyler King

But also it's it's nice making money. So I'd say that was kind of the first phase. And then there's kind of the early employee phase, which you still very much feel like a bunch of renegades just doing whatever you want. The people you hire. I mean, you can do whatever you want, obviously. But what we did is I hired friends, people that I already had a lot of trust built up with.

00:04:32:17 - 00:04:52:07

Tyler King

I wasn't spending time managing them or anything like that. So that kind of early that just a handful of employees phase still felt very much like freedom. Try a bunch of stuff, take risks. And then since then, as we've kind of been growing and hiring people I didn't already know and people have, I feel like it's more of a boss employee relationship instead of a few friends trying to hack stuff together.

00:04:52:07 - 00:05:07:05

Tyler King

It's just kind of constantly evolves to a more and more mature business where I have to like, manage people and be in meetings and think about I can't like say whatever I want because if I, if I express how risky something is, people might think that that leads to layoffs or, you know, like you just kind of have to start being an adult.

00:05:07:05 - 00:05:08:18

Tyler King

So that's kind of where we're at right now.

00:05:08:19 - 00:05:15:00

Andrew Davies

Can you told me about talk me through maybe pick out one or two of the absolute highest highs and the lowest lows of that journey so far?

00:05:15:01 - 00:05:33:03

Tyler King

Much to my surprise, I said, like we just wanted to build stuff at first. And I actually really resisted the idea of hiring anyone, really resisted doing any customer service. I just don't like people, basically. And I'm very surprised that I think the highest highs I've had are basically company events like parties or whatever, hanging out with employees.

00:05:33:04 - 00:05:52:03

Tyler King

That's probably not a very interesting answer from like a business perspective, but just seeing a bunch of people who genuinely like being around each other and you have an impact on all your customers, but it's it's a small impact across a large number of people. The impact you have on employees is a huge impact across a much smaller group of people and seeing how much it can change a person's life to work a place they actually enjoy working.

00:05:52:03 - 00:06:08:14

Tyler King

And I think that's that's the highest high probably. And then you said lowest low. Any time people kind of joke that, you know, my, my, my, our graph is my my mood. Basically anytime growth is looking bad, but specifically, I think we went through a pretty painful transition because in the early days, you know, I lived in San Francisco.

00:06:08:14 - 00:06:38:05

Tyler King

I was surrounded by tech people who just there's this attitude of just unlimited growth. Right. And in the early days, it's easy if you have 100 customers. And, you know, we serve very, very small customers, going to 200 is not that hard. Then when you have 200, going to 400 is harder and it just gets harder and harder and harder and eventually reality sets in that it's like we're not on that Uber Facebook type of trajectory and we kind of had been making a lot of assumptions about you can get away with whatever you want if you think that basically if you treat it like a Ponzi scheme, like if the next round is going

00:06:38:05 - 00:06:52:19

Tyler King

to be so much bigger than the current round, you can hire more people than you can actually afford. You can make promises to them. We're all going to be millionaires in a few years and as soon as reality set in, you know, we've still got a really healthy business here. But a lot of those promises I made and assumptions I made ended up not being correct.

00:06:52:19 - 00:06:59:00

Tyler King

And that transition from thinking we were going to be the next salesforce to thinking we're just going to be a really nice small business, that was painful.

00:06:59:00 - 00:07:24:17

Andrew Davies

And I want to dive into that because I know you've got your own podcast, which is called Startup to Last. I will make sure there's a link to that so people can listen to more of this journey. But I'd love to hear a bit more about that recalibration from Believe In You on that hypergrowth curve to recognizing that perhaps good fit for you and your business actually plan A for you and your business would be smaller than than what your first expectations and ambition were.

00:07:24:18 - 00:07:40:05

Tyler King

I can point to a specific moment where this realization set in because I mentioned in the early days I hired some friends who had experience, worked in tech, like knew what they were doing, and one person in particular was in charge of kind of growth marketing type stuff. My attitude was, let's become billionaires and also let's not do all that annoying stuff that other companies do.

00:07:40:08 - 00:07:55:17

Tyler King

We had been struggling a bit with growth, like it'd been so easy up to this point, and then it got hard and he kind of sat me down and said, I don't think you're strong enough of a leader to do what you're saying. And specifically you're not willing to do what needs to be done. You won't take a credit card upfront because you think it's annoying.

00:07:55:21 - 00:08:08:09

Tyler King

We should be doing that. You won't try and lock people in annual contract. I mean, we allow people to pay annually, but we don't like push it. We won't spam people. He was just like, Here's all these mechanisms, all these levers I could pull to help with growth and you won't let me do any of them. You're not going to make it.

00:08:08:09 - 00:08:25:14

Tyler King

And he was right, first of all. But he was saying this to say, it's time to let me loose, let me go. Like let me do all these things I need to do. And we kind of took the other approaches. He was like, No, you're right. I didn't realize what it took to run that type of business. And it's not for me and it's not for he wanted to, but most of the other people didn't.

00:08:25:14 - 00:08:31:21

Tyler King

And so we decided basically we're just not going to even shoot for that goal anymore. And he and a couple other people left as a result of that.

00:08:31:22 - 00:08:50:04

Andrew Davies

Let's dig into a little bit more about this, because I think although this started to be talk about it, I think it's an undeserved topic. I've run bootstrapped businesses and I've run VC backed businesses. You know, I think both are hard, but they're hard for different reasons. So, you know, you described kind of hyper growth in the funding cycle as a bit of a Ponzi scheme for those who are listening on this call.

00:08:50:04 - 00:08:57:05

Andrew Davies

You haven't made the call yet or who don't understand what that means. Talk to us in a bit more depth about the negative consequences of raising funding that you've seen.

00:08:57:07 - 00:09:13:05

Tyler King

I think what it comes down to is if you're telling yourself that you're going to grow massively in the next couple of years, you don't have to make any trade offs right now. You can like imagine there's three main sets of stakeholders. There's kind of the owners or shareholders, there's the employees and there's the customers. You don't have to decide who's going to get rich.

00:09:13:05 - 00:09:31:14

Tyler King

You can say, we're going to have a billion customers. Each one's going to pay us 100 bucks a month or a year, let's say paying nothing. That's a very low price, but that's still $100 billion in revenue. I'll take a couple billion. My employees will take the rest. Everyone's customers are paying a small amount. I'm getting rich. Employees are getting rich.

00:09:31:14 - 00:09:48:06

Tyler King

Everyone wins. If you can just keep telling yourself that you're going to double and double and double. That story keeps working as soon as you know the reality sets in that well. A It very rarely goes that way. The idea of a CRM company having a billion customers is obviously not realistic. But I started this company when I was 24 years old and I didn't know any better.

00:09:48:06 - 00:10:06:03

Tyler King

As soon as you start facing reality, you start saying, No, actually there are tradeoffs. If you want to get rich, you're taking it from someone else. You can do the Jeff Bezos thing and just push employees to the absolute brink and pay as little as you can get away with and just squeeze it out of customers. But give or squeeze it out of employees, but give customers the best experience possible.

00:10:06:03 - 00:10:20:01

Tyler King

Or you can, you know, take the other approach that many enterprise companies take, which is we are sorry, I'm not trying to call people out here, but like like I think Intercom is a company that's famous for this, which is they price at the absolute maximum amount they can possibly get away with. And they have a great product, great service.

00:10:20:01 - 00:10:36:09

Tyler King

Many people are really happy intercom customers, but if they want to get rich, they're taking it from their customers. And that's what I didn't confront in the early days of the business is that it's kind of a zero sum, like some of it's accretive and that you can create new wealth, new value. But sometimes you have to make decisions where it's like it's me or it's someone else, and we need to balance.

00:10:36:09 - 00:10:53:16

Andrew Davies

Those in the current environment where we are post the zero interest rate phenomenon. And there's been an evacuation of capital out of early state financing and mid-stage financing as well as late stage. And so there's much more narrative again about bootstrapping and the health of the business and efficient growth than there was back when you made these calls.

00:10:53:16 - 00:10:58:08

Andrew Davies

How tough was it to make that decision and bring others with you along on that journey?

00:10:58:08 - 00:11:16:07

Tyler King

I'd say it was hard in the way that like a breakup where, you know, you were never meant for each other. It's hard. It's not hard in that I didn't really have any uncertainty about what the right thing to do was. But yeah, you're like, Oh, well, okay, I guess I get paid plenty. Well, I'm not I'm not struggling here, but I'm like, Well, I guess I'm not going to own a yacht one day, you know?

00:11:16:08 - 00:11:35:00

Tyler King

But also just like the, the impact, like I thought we could change the CRM industry. And one of, you know, STRIPE'S stated goal is to increase the GDP of the Internet. We kind of jokingly say our goal is to decrease the GDP of the CRM industry. We want like everybody to be paying less and buying simpler, cheaper software.

00:11:35:00 - 00:11:45:06

Tyler King

And you just kind of realize like, okay, that's not the type of impact we get to have. I still miss that dream. And also it was never going to happen. And so kind of coming to terms with that was the right thing.

00:11:45:06 - 00:11:54:02

Andrew Davies

I think it's so important that people make these decisions based on their own personality, but also based on the market reality. Both of those are very instructive into that decision making process.

00:11:54:02 - 00:12:01:12

Tyler King

Yeah, I should acknowledge, like even if I tried that, it doesn't mean if I'd done all this other stuff, we'd now be $1,000,000,000 company. We probably still would have failed at that. Right?

00:12:01:14 - 00:12:16:00

Andrew Davies

You talked a little bit about customer kind of service and making sure our customers were really happy. So I know that's one of your key differentiation from other competitors. So talk to me a bit more about how you set up for surprising and delighting your customers more than your competitors, I.

00:12:16:00 - 00:12:33:17

Tyler King

Should say important context here. I said earlier that we're serving like insurance agents as kind of lots of different industries for that type of person. We primarily serve low tech people who it's very different if you're selling to a bunch of programmers or something. But this was never really a goal of ours. But I remember I put my phone number on the website just because I was like, I guess that's what you do.

00:12:33:17 - 00:12:46:20

Tyler King

And someone my phone rang one day and I picked up and they were like, I have called like 20 different systems in a row. And here's the first one they picked up and I didn't know what to do. I'd never talk to a customer in my life before, but I was like, okay, So I just botched my way through the call.

00:12:46:20 - 00:13:12:07

Tyler King

It was terrible and the customer was so happy. They're like, You talk to me to some extent. I think that's all it is, is just like, make yourself available. I think our tech companies and startups are so fascinated by automating everything away and all this, and it's great. Unit economics are better if you don't talk to people and all that, but if you want to kind of swim upstream and zig when everyone else zags, it starts with just as a founder putting your phone number on a website and you kind of can't mess up like, you know the answer every question.

00:13:12:07 - 00:13:17:20

Tyler King

Assuming you're not a horrible person, you're already in the top 1% of companies for customer service at that point.

00:13:17:21 - 00:13:22:14

Andrew Davies

Have you seen other businesses in your space react to what you do here and try and compete with it?

00:13:22:17 - 00:13:36:11

Tyler King

No. I mean, simple answer is if you're trying to start a CRM company, you can go after us and maybe steal 3.8 million RR, or you can go after Salesforce and steal however many tens of billions they make. I don't think anyone cares about us, to be honest.

00:13:36:11 - 00:13:52:01

Andrew Davies

Before we go on and talk about how to build a startup to last, I just want to stop on that topic because I love your name, because you've got such a very clear positioning statement within it. I mean, the tech space. So obviously Salesforce comes to mind, right? I know exactly what you're talking about when I when I hear the name less annoying CRM.

00:13:52:01 - 00:14:04:13

Andrew Davies

I know exactly what you're doing. I know exactly what you stand for. I know the kind of experience I would get. I know they're going to Price Point I'd get was that at the very beginning a founding decision, that position in that name and talk talk to us about kind of why you felt so bold.

00:14:04:17 - 00:14:19:02

Tyler King

So we actually came up with the name technically, our company name is less annoying software, not less annoying CRM. And we actually came up with that name before deciding to do CRM. So my brother and I, he's my co-founder, we were just talking and we're like, you know, what should we do? What are we going to? And we went through a few ideas that we ended up scrapping.

00:14:19:02 - 00:14:37:19

Tyler King

But about halfway through that process we said, What do these all have in common? And they are we're both just cranky people. We would, you know, someone would launch a new product. This is late 2000. So like 2009 is when we started, you know, Google would launch Google Wave or something like that and we'd use it and we'd be like, Here's what I like, but also here's what I don't like.

00:14:37:19 - 00:14:55:08

Tyler King

And we just complained about software to each other all the time. That was our relationship. And every idea we had was, let's take something that exists and just take out all the annoying stuff It wasn't. Let's innovate on some brand new thing. No one's ever heard of. And I think for bootstrap kids especially, it's so hard to create a new market from scratch.

00:14:55:08 - 00:15:06:09

Tyler King

It's so much easier to say there's already existing demand for this thing. I can go use it. I can see what's working and what's not, and I can just make something less annoying. So we kind of knew that even before we knew that CRM was going to be our thing.

00:15:06:09 - 00:15:23:10

Andrew Davies

So let's get onto kind of one of your specialist topics that you love digging into, which is building startups that last before we kind of dive into some of perhaps the topics we've covered on your podcast and you're thinking about this, what does Lost mean for poor generally, but also for less annoying CRM? What timeframe are you looking at and what does lasting mean?

00:15:23:10 - 00:15:39:10

Tyler King

I don't have a specific timeframe, but I'll say the idea of having an exit strategy has always just seemed bizarre to me. Sometimes it makes sense to sell. It makes sense to get acquired. I'm not saying no one should ever do that, but the idea that you're starting a thing so that you can stop doing the thing just never made any sense.

00:15:39:10 - 00:15:56:11

Tyler King

Like, why are you doing it in the first place? Do something you would actually enjoy doing long term, and if an opportunity comes up to sell, go for it. But this really tastes like my last job before this was a traditional VC backed trying to get acquired type company and we started this and just said, Let's start something we want to do forever.

00:15:56:12 - 00:16:13:06

Tyler King

Now this ends up being really good for customers. We have customers contact us all the time and they're like, a lot of our customers are older and so they'll be like, Oh, my first year arm was in the eighties. It was something I've never even heard of before. And then they're like, and then they shut down and then the nineties this happened and then they got bored, so they switched to this and they're just like, I'm just look, I got ten years left before I retire.

00:16:13:08 - 00:16:30:07

Tyler King

I'm just looking for something that's going to be here for ten years and it's been really nice being aligned with customers on that, that just like you want something that's going to last, we want something that's going to last. And sorry, I didn't really address your question, but longer than me, I guess that's my answer. I want to retire while still owning and running this company.

00:16:30:09 - 00:16:58:01

Andrew Davies

That's so interesting. I love I love the answer longer than me. But it's interesting specifically because I've often seen in vendor evaluations companies look at whether a company has got a supplier, has got VC dollars as a way of predicting that they might be successful or lost. Newstead In the complete opposite approach, because your target markets, their evaluation of you and it might not be in a vendor evaluation by procurement team, but their evaluation for you is that they're betting on you and they're betting on your principles to last longer than you would.

00:16:58:01 - 00:17:05:07

Andrew Davies

If you're a bit more of a flash in the pan, raise them dollars and see what we can flip. I find that fascinating. And I guess it does come down to the type of customer you're serving.

00:17:05:09 - 00:17:26:01

Tyler King

100%. But like I would encourage anyone out there who's kind of in the early stages to like it works, it's so tempting. Everybody tries to pretend to be bigger than they are. And, you know, they use the word we when they mean AI and things like that. If a customer calls up and I don't do that much fun sport anymore, but I still, you know, every week or to do an hour of phone support if a customer calls up I get this question all the time and they say, How do I know you're not going anywhere?

00:17:26:01 - 00:17:42:13

Tyler King

And I literally just say, I promise I'm the owner. I'm telling you, these are my goals. It works. Now, I'm not saying like you could use this in kind of a manipulative way, but as tempting as it is to say, oh, because we've raised money or because we're this massive that you try to make it so unprofessional that it doesn't matter what you want.

00:17:42:13 - 00:17:50:22

Tyler King

But if you're a solo founder or a small team and you just say, Hey, I'll connect with you on an individual level and I'll tell you that this is what I'm in it for. Most people believe.

00:17:50:22 - 00:18:00:11

Andrew Davies

You start the last. You're podcasting about this. Talk to me about some of the topics that you found most resonant with your audience about building a startup. The last.

00:18:00:11 - 00:18:27:22

Tyler King

I should probably say, like the topic, the underlying theme is I want to start and my co-founder wants to start companies that will last. But you don't do that by spending all day talking about building companies that will last. You do that by operating companies really well. Almost all the topics would be equally applicable to a venture backed or someone who wants to exit or whatever, With the caveat being there are a lot of decisions you can make that are good for short term growth, raising the next round and so on, and we just completely eliminate all of that.

00:18:27:22 - 00:18:41:17

Tyler King

So it's what will provide value to customers long time, what will retain employees for a long time. But it's really in the weeds operating type of stuff. And I'm kind of a big believer in like a good conversation is one with a lot of back and forth. So we try to bring topics on there that we don't know the answer to.

00:18:41:17 - 00:18:55:00

Tyler King

So I might go in and say, Hey, we're struggling with growth right now. AdWords is capped out. Capped here is going well, but we don't have more budget for it. What should we do? And we'll just get into the weeds of how we're doing marketing. And he'll give me ideas, I'll give him ideas and just workshop it.

00:18:55:00 - 00:19:18:05

Andrew Davies

The idea of building public and talking about your journey like that transparently. Many, many people are starting to do that now. The value, I think, really depends on your personality and how willing you are to be open with those numbers and also your aspiration, how much you're living up to your own internal narrative of growth. Who are the other building public founders that you follow will look up to or trigger that need a new or that desire, renewal or is it genuinely a case of you're just doing this for your own benefit?

00:19:18:06 - 00:19:32:00

Tyler King

A little of both. I'm happy to name people, but and I will. But I think there's a big difference between doing build in public to try and find customers, which I am not doing. Nobody in our circle is going to buy less annoying CRM. You'd sign up for it and be like, Where are all the features? And we'd be like, Yeah, we don't have any.

00:19:32:00 - 00:19:50:00

Tyler King

And then you live. We are for a different type of person. So my build in public is to find peers and to find a network. By being based in St Louis. There's not a lot of startups here not having a board of directors because we didn't raise money like you can be kind of lonely as a bootstrap. Or for me, building in public is about finding peers, not about finding customers.

00:19:50:00 - 00:20:13:21

Tyler King

So I think that's an important caveat. I have really liked following Ben Ornstein on this. He had the Art of Products podcast and now I figure what his new one's called, but his new ones are great too. I think following Rawlings great. I think unfortunately a bunch of the people I follow have stopped doing this recently. But that whole circle of there's kind of like a bootstrap or like the MicroConf and com fund communities, those are the people I like to follow.

00:20:13:21 - 00:20:31:01

Andrew Davies

Especially you talk about optimizing for the long term, not the short term or long term for your team, long term for your customers. That must be challenging because over the long term, you know, you can't see too far into the future. The market changes, the needs change, the customer changes. So can you talk me through some decisions where perhaps you had to take a risk on what will be true for the long term?

00:20:31:01 - 00:20:44:10

Tyler King

I'm not sure how big of a risk this was, but like an example of this type of decision we definitely had to make. So if you're starting a business with the plan of like growing real fast and exiting, you would never, ever think about what I'm about to say. And that is over the last 14 years, a lot of our customers have retired.

00:20:44:10 - 00:21:00:04

Tyler King

And if we want to be here for the next 30 years like I am, I'm 38, I am younger than our average customer right now. And that means if I want to continue running this business until I retire, that means we have to find younger customers because all of our customers will be retired before me. And what does that mean?

00:21:00:04 - 00:21:19:00

Tyler King

We don't want to abandon our current customers, certainly. But it is true. It's not all about age, obviously. But on average, young people grew up digital natives. They may be more comfortable with certain types of features. They may be less likely to want to use phone support. So one of the things that we've kind of struggled with is we want to really do right by our current customers and carry them out to retirement.

00:21:19:00 - 00:21:23:14

Tyler King

But we also need to start positioning ourselves for a younger audience that probably values different things.

00:21:23:14 - 00:21:29:21

Andrew Davies

Are you putting just research resource into that or are you putting any actual product resource into building for the new customer?

00:21:29:22 - 00:21:49:11

Tyler King

I would say we're putting some it's a slow roll, right, because these things don't happen quickly. But an example is a change we're making right now. It's not live, but it might be by the time this podcast goes out, we have really good customer service, but we also have really good like kind of automated onboarding. If you sign up for an account today as I'm saying this, you're going to land on this thing called the Beginner's Guide, and it's just a series of videos that go super in-depth.

00:21:49:11 - 00:22:03:17

Tyler King

It's the type of person you know, you buy like a microwave and there's a manual, somebody reads that manual. I don't and I don't think you do, but someone is like opening that up and reading it before they plug the microwave in. That's kind of our customer right now. And so our onboarding treats them that way. We're actually about to make a slight switch.

00:22:03:17 - 00:22:18:13

Tyler King

We're still going to have all these videos. They're going to go even more in-depth than they do now, but it's going to be more of a choose your own adventure thing. When you sign up, you're going to get set down right in the CRM so you can start playing with it. Because what we found is with more tech savvy people, they want to experiment first and get a feel for it, and then they want to go look at the help resources.

00:22:18:13 - 00:22:28:03

Tyler King

So we're just kind of changing the order and letting them choose when to watch the videos instead of saying, Read the whole manual first. That's just one small example, but we're kind of bit by bit making little changes like that.

00:22:28:03 - 00:22:46:15

Andrew Davies

All of the founders I know who are building small giants built to last building companies that are there for generations rather than going on that rocket fuel powered hypergrowth journey, they have to make very hard decisions now. Focus is always true. You've always got to focus and you always got to make hard decisions. But it's especially true in your scenario.

00:22:46:15 - 00:22:51:23

Andrew Davies

So can you talk to me about some of the most painful no decisions you've had to make? Decisions of? Focus.

00:22:51:23 - 00:23:05:10

Tyler King

Yeah. I mean, there have been so many. One of the big ones that also ties into your last question about like, what am I worried about? Maybe like changing in the future? We have avoided it's important to us to have a low price point and there are some features you can build that take a lot of time, but not a lot of money to like.

00:23:05:10 - 00:23:24:08

Tyler King

Host There's not much infrastructure cost, but two things in particular that people really want, especially increasingly more and more of the time, is they want SMS automation and email automation. And doing these things comes with costs, like every tool that sends out email, like a lot of serums will send emails, but they're you're paying hundreds of dollars a month, not $15 a month.

00:23:24:08 - 00:23:40:22

Tyler King

There's just no way for us to do that at our price point. So we've been saying, no, no, no, no, no. It's cool if you want that, but you should use a different product or you should use our integration with MailChimp or whatever. And I think increasingly over time, the definition of a CRM is changing to me and like if it doesn't have email, is it even really a CRM?

00:23:40:23 - 00:23:45:08

Tyler King

That's an example of a thing that we've said no to. But I don't know, like our resolve is being tested on that.

00:23:45:08 - 00:23:47:17

Andrew Davies

And the other powerful no's you've had to do that have been painful.

00:23:47:17 - 00:24:07:02

Tyler King

I mean, there's lots of stuff around permissions and reporting and automations. I think this happens to anyone that sells to small businesses is someone's going to come along and be like, I've got 500 users. We're ready to go. Like all we need is this feature. And first of all, they're always lying. Don't listen to them. They're lying. As soon as you build that feature for them, they're going to be like, Oh, we also need this other fee.

00:24:07:02 - 00:24:22:15

Tyler King

It turns out a product not built for enterprises is not going to be good at serving enterprises. But yeah, we constantly are saying no to I want all these reports to kind of see like we have zero ROI. I like reporting, we don't have we can't some numbers at all. Now to be clear, we actually are going to build that at some point.

00:24:22:15 - 00:24:37:10

Tyler King

But like there's no visual reporting, it's just lists of things. And we have our small business customers sign up and they say, Thank you so much for not overwhelming me with this dashboard of stuff I can't understand. I just see my contact list. That's what I want to see when I log in. Saying no to that has been hard.

00:24:37:10 - 00:24:42:08

Tyler King

And again, maybe over time we'll have to kind of adjust because people are getting more tech savvy.

00:24:42:08 - 00:24:58:18

Andrew Davies

So let's now speak directly to the thousands of Sophia founders that are listening to this. Let's talk directly to those who are making this decision right now of which path they choose. Do they raise money or do they go through the hard yards of bootstrapping? What are your frames of reference? What are the what are the ways you think about that decision and how would you coach them?

00:24:58:19 - 00:25:16:01

Tyler King

Yeah, I think part of it is upside in the sense that if you if you want to get really rich, the best way to get really rich is to raise money and exit. That's just proven time and time again. I would challenge some of the question though, what enough means. This This has been as I've kind of matured as a founder and just as a person, understanding what I need to be happy.

00:25:16:01 - 00:25:31:01

Tyler King

I don't think the difference between right now I pay myself $209,000 a year and I don't take any other money out of the business in any way. I live in St Louis. That's a low cost of living city. That's plenty. I'm not saying I'll never pay myself more, but I kind of came to grips with the fact that like, what would I do with more money?

00:25:31:02 - 00:25:48:07

Tyler King

But someone else might say, Well, I really want to fly private, I really want a penthouse in Manhattan. And so I think figuring out what you want is the first step here. Like, is the difference between $1,000,000,000 and $10 million really that much? Because reality is I could sell something here and make I don't know, maybe not. Now, if I'd sold two years ago when multiples were higher, I could have made $10 million.

00:25:48:07 - 00:26:08:16

Tyler King

Is the difference between $10 million and $1,000,000,000 meaningful to you? And I think the numbers reflect that. Despite what everyone says, bootstrapping is safer, there is less risk in bootstrapping. You are more likely to get a seven or eight figure outcome with bootstrapping than you are with venture capital. But the upside is lower. That's probably the main framework that I would use.

00:26:08:16 - 00:26:22:16

Tyler King

And then the secondary thing I would say is do you care about anything other than money? Some people are just starting a business to get rich or just starting a business to have lifestyle, which I would say both of those are about money, like lifestyle. You buy it with money basically. Do you care about other things? Like I care about customers.

00:26:22:16 - 00:26:41:07

Tyler King

And again, like I said, to my surprise, I really care about employees now and it's been worth it to sacrifice. Like I get to go into work two days a week, we do two days in office and just see a bunch of people I love working with, and that's worth a lot to me. And like you might consider, do you care about that type of thing, a bootstrap or can control every single aspect of venture?

00:26:41:11 - 00:26:49:00

Tyler King

If I raised VCs, they come in and they'd say, Lay off half your customer service team. The other half cut their pay in half and let's get going. You know.

00:26:49:00 - 00:27:07:23

Andrew Davies

Tata has got a whole range of different topics on his Startup to last podcast and even an episode. They're on handling sales taxes. SaaS About the choice of using PUDDLE before we close, Tyler, have you got any other advice that we should make sure we include for the SaaS founders that are listening regarding building their business as a sustainable startup that will last?

00:27:07:23 - 00:27:27:23

Tyler King

I think I just want to reiterate that last thing I said. Sorry, this probably isn't the most interesting answer, but it all comes down to what you want. Every business that wants to be worth $1,000,000,000 is the same, and every business that wants to be worth 10 million is totally different. And just don't put yourself into that same path that everyone else is doing because it looks like the only way to succeed.

00:27:27:23 - 00:27:38:13

Tyler King

Figure out what you want. Make something no one's ever made before. Not necessarily with the product, but with the company. And don't let anyone else set your kind of your dreams for you.

00:27:38:15 - 00:27:53:11

Ben Hillman

Shout out to Tyler for being on the show. Make sure to give Protect the Hustle a five star review, and tell us what lesson from today's episode was your favorite. Thanks for listening. Subscribe to and tell your friends about Protect the Hustle, a podcast from Paddle Studios dedicated to helping you build better sets.