Episode 786 | Questions About Bootstrapping SaaS to a $90M Exit (with Kevin Wagstaff)

Rob Walling :
If you’re listening to startups, For the Rest Of Us, I’m your host, Rob Walling. In this episode, I talk once again with Kevin Wagstaff, the co-founder of Spector. And if you recall, he was on the show just a month or two ago talking about how he and his brother bootstrapped their SaaS to a $90 million exit. In that episode, I made a call for questions if you had any questions about how Kevin got where he is trying to go. And I received an email filled with an entire episode’s worth of questions. Turned out to be a really great conversation. I think you enjoy it. Before I dive into my conversation with Kevin, if you ever wished that you had an outsider’s advice from someone who’s been in the trenches of trying to grow your SaaS past 1 million, 2 million, 3 million a RR, then you should check out Tiny Seeds SaaS Institute. 

That’s at SaaS institute.com, and it is our premium coaching and mastermind community where you’re going to get all the advice, the comradery, the mastermind interactions, and one-on-one coaching that you want. It’s exclusively for founders doing 1 million a RR end up and it’s only SaaS founders. We’re currently forming our next mastermind group and we have one or two slots left. We’re still in the early stages of institute, and so if you want to get in on the ground floor as a founding member while the community is still small and you’ll get a ton of one-on-one attention, should check out SaaS institute.com. And with that, let’s dive into my conversation with Kevin. 

Kevin Wagstaff, thanks for coming back on the show. Oh, of course, man, you make it easy. It is a pleasure to have you back for the second time in just a couple of months. For those who don’t know, your last episode was episode 776, how bootstrapping led to a life changing $90 million SaaS exit. And if the title was even longer, it would then say, and a subsequent exit at 110 million that he co-founded with his brother. There’s whole thing folks should go listen to that 45 minute conversation we had. But in that episode I asked for questions because your story was so compelling and there’s so much more to it, and we probably could have done three hours and still only touched on elements of it. And so I asked folks, send an email, hit us up on X Twitter if you have questions for Kevin, and we got this amazing email from Tom at Garage tool app and he gave us a full episode’s worth of questions. So that’s what we’re going to be diving into today.  

Kevin Wagstaff:
Appreciate the specificity on ’em too. Your listeners, I think are so dialed on this stuff. It makes the content easy when they ask such great deep bootstrappy SaaS questions.  

Rob Walling :
That’s what I liked about him too. There’s no question here of Kevin, what are your top three advices for nude? You know what I mean? Or what’s your number one piece of advice for new entrepreneurs? It’s like, I mean, to keep going, persevere, work hard, but this is detailed and let’s dive right into the first one. The cool part too is several of these are multi-part questions, so I think we’re going to get in here pretty good. So first question, Kevin mentions that he approached Facebook groups to do some of his early marketing. So Kevin, did you have to offer anything in return for that? And if so, what did you offer?  

Kevin Wagstaff:
Initially we did offer a discount on the software because we just, no one knew who we were brand new. Got to get someone to join this group. So I believe we offered a godfather type grandfather deal of six months free and grandfathered price for life, the cardinal sin. But after we got 10 or 20 or 30, the main pitch was access to the founders. So it’s like, hey, if you have ever been with a software where you didn’t change or didn’t like how little change was happening, guess what? You can talk to me directly in this group and we’ll dialogue back and forth and then follow through on that. So really it was like you’re going to hear directly from the people that make the decisions here.  

Rob Walling :
And were you going into existing Facebook groups or did you start your own Facebook group and try to pull home inspectors into it?  

Kevin Wagstaff:
Yes, both. So we spent so much time on there that it was like half the time we spent in our own group fostering those relationships and creating rich content, asking good questions, being in so many threads to make our group good, but then we would also go into other groups and answer questions half the day basically.  

Rob Walling :
Did you do both of those things, meaning your own group and posting in other groups? Did you do both of those kind of from day one?  

Kevin Wagstaff:
Yeah. Yeah. Got it. It was basically the first and last place every day for I’d say for sure the first two years we visited, which was exhausting and taxing and don’t recommend it for most people. Do you want to be happy or do you want to spend that much time on Facebook?  

Rob Walling :
Well, do you want to be happy in long term because you build an incredible business but unhappy in the short term? Dude, I tell you, I dunno if you listened to, it was last week’s episode, but I, I think it was my 12 biggest mistakes that I made as an entrepreneur in my 10 best decisions or something like that. Why I succeeded in spite of those 12 mistakes is what I was trying to pull out. One of them that I said was a boon for me was willing to just grind to grind and do stuff that I didn’t want to do and nobody wants to do. And I was thinking of, there’s several founders that I think of who do this, Jordan gals one and Ruben. There’s these folks who come on the show that I know that I know their grind stuff, but you were another person in my mind when I was writing that of thinking about our conversation and specifically around Facebook groups like do any of us want to do Facebook groups? No, but you did it because you do.  

Kevin Wagstaff:
That’s where the customers were and I was getting good positive engagement and interaction, and if I’m getting one to a hundred people in any given month closer to being a customer, it’s like, I’m going to keep you talking to me. I’m going to get you to like me, and then you’re going to want to do business with people you like. So that was just the mentality. I kept asking questions and they kept responding. So I’m like, cool, let’s keep this going.  

Rob Walling :
You did it because it worked well enough and it didn’t really matter if you wanted to because it worked well enough and you wanted to build a great business more than you wanted to be happy at the beginning and ending of your every day. Is that accurate assessment?  

Kevin Wagstaff:
Pretty much. And I didn’t really care about work-life balance. I think COVID and kind of the current culture and climate, I think people do believe, and some of ’em are right, where you can kind of have your cake and eat it too, but it was an all out kind of burn the boats. We’re going to do this for years and we’re going to show up every day and show people that we’re ready to elbow a way in to be a competitor in this space, not we’re going to show up, see if it works, give it that half committal. That just wasn’t the mentality and it’s not right for everyone, but we knew we had to go fully into this to show people that we’re trustworthy.  

Rob Walling :
And as a reminder, you co-founded Spector your SaaS that we were talking about with your brother. So when you say we, that’s who you’re talking about 

Going off script here because Tom didn’t ask this question, but something you said brings something up for me, which is you said I didn’t think about work-life balance. So someone hearing this might think A, that’s not healthy. How long can you do that? They might also think, is that what it takes? Is that what I need to do to be successful? So for you, I mean I’m curious about both of those questions, but it’s like for you, because had times of no work-life balance, but my goal was I only want to do that for X amount of months or in terms of drip, it wound up being a few year, few more years that I would’ve liked, but again, in the end it worked out, right? So how did you think about that? Were you just like, no work-life balance and I’m just going to do it until it’s done? Or were you kind of like, eh, I can do this for a year or two before I really need to back off?  

Kevin Wagstaff:
Yeah, I want to hear your experience on this too. Yeah, ours was similar, whereas we knew it’d be this undetermined amount of time from a few months to maybe a year or even two, ended up being longer than that ended up being two, three years of burning the candle both ends, but it was intoxicating seeing growth and results. And so anyone that’s competitive or kind of a junkie in that way of seeing the numbers go up, we watch the fricking MRR chart every day and it’s like if you like video games, we grew up playing video games every little boop, boop, boop, and we were just like, okay, we’re total addicts for this, so let’s just keep it going. And yeah, we still on the weekends would play volleyball or workout once or twice a week. It’s not like the sleeping under your desk kind of lore of you’re literally withering away. 

And at times we felt like that, but yeah, I don’t want to over glamorize it either. Yeah, everyone always has the quick response of like, well, that’s not good for your health and relationships. Well, it’s like, yeah, no shit. We wanted to do what most people wouldn’t so we could get a result that most people don’t get because everyone wants work-life balance. We all want to be happy all the time, but that’s why so few companies probably succeed. And so it’s like, I don’t know, I found the endurance from sports and me and you had our athlete talk of doing hard things for a long time trains you mentally for that. And I really felt equipped and there was times I was like, yeah, give me more. I can go another hour. And it was like 11 or 12 at night. And so I think everyone can generate that within them. I don’t think you have to be special to be an effort guy.  

Rob Walling :
I agree. One thing that you said in there that really resonated with me is it wasn’t just that you two were grinding hard is that the MRR kept going up and that’s the feedback loop because if you had done what you were doing and there were no results and you’d plateaued at three grand or four grand, you know what I mean? And you can only do that for honestly months. I couldn’t grind for a year with a plateau like grind the way you’re talking about, which I have done periodically. I try not to do it, but if the feedback loop is that we’re adding a thousand a month to three 4,000 a month, then how do you not do that?  

Kevin Wagstaff:
Even if it’s top of funnel or if it’s like, Hey, we’re seeing incremental growth 1%. Hopefully that’s all you need to see, but everyone’s bars are different for what keeps them fueled and going what your TAM is and all that. But yeah, to your point, was it hard those couple months where you’re like, gosh, we keep pivoting. Things are plateauing. Those are demoralized. We had stints of that too where it’s like our chart doesn’t show a lot of that, but there were months when the interest rates stuck and it was like, oh crap, this is more exhausting now.  

Rob Walling :
That was my memory of my times of grinding were as long as the results came, I kind of forgot about how hard it was, but it was the months where, yeah, we grew 200. It was often Decembers and Aprils for something and for some reason, and April I always assumed it was tax season for the US or whatever, and people were distracted. And December was obviously because holidays and those months if we, you’d grow nothing or you’d go 300 MRR when I’m used to growing 5K MRR and I would just be like, oh my gosh, now I’m exhausted and burning out. It was interesting how the burnout only hit me when there was no feedback loop  

Kevin Wagstaff:
And maybe those are the months if we were to do it again where we do cut out an hour earlier and go work out hard or make sure we’re eating healthier and kind of managing that. That’s probably what I would do differently is know the seasonality of our business and take care of myself a little more.  

Rob Walling :
Yeah, I agree. And also, again, I know I say this a lot, but it’s like every time that I was doing more work than I want it to be, it was always like, this is a season. This is not permanent. And I don’t know if this season is a month or if it’s five months or six months. I never did it for a year straight like that. I did feel stressed for a couple years, but I didn’t work more 40 hours a week for more than a couple, two, three months at a time. It sounds like you guys were doing more than that.  

Kevin Wagstaff:
Again, I don’t want to undersell or under characterize here that the point in time we felt this huge momentum shift and like you said, the feedback loop was there. And so I definitely am grateful for that and I know it’s a lot easier when the scoreboard keeps going up, but we wanted to capitalize on it. We didn’t want to take it for granted. So in a way I thought we were being grateful for the opportunity given by saying, let’s just quadruple down here every day.  

Rob Walling :
Yep. Go with what works. And so to get back to Tom’s questions still relating to Facebook groups, Tom asks, were you worried about some of the admins of these Facebook groups being allied with some of your competitors? The biggest Facebook group in our industry is Allied with one of our competitors, and this competitor is actually building a pretty sizable audience. Was that a risk for you?  

Kevin Wagstaff:
Yeah, I was terrified of that. I hated those. Those guys were the hardest to even, it’s being the new kid on the playground and you see all the cool kids hanging out in big groups of them and you walk out there and they just point and laugh at you. That’s how I felt. My wife got so protective over me, she thought she felt like I was just getting bullied online for a whole year. So she’d be wanting to get on Facebook and curse these guys out, and I’m like, sweetie, that won’t be a good look for us, so I’ll be okay. I’m a grown man, but I’m not going to lie. These other Facebook groups were really hard to get into and the ones affiliated with competitors. I had to really go in hat in hand and just say, Hey, I’m here for the good of the industry. 

I don’t care if you guys use Spector. I want to help you guys market your businesses better. I want to help home inspector save time and just repeat that mission, vision, values statement over and over and showing up. You have to do the work and show up every day and show them like, Hey, I’m not here for a quick sales pitch. And then I also showed vulnerability. That always helps in life, I think of going in there and saying, Hey, look, I know we don’t have the features of Home Gauge because at the time we didn’t. I was like, look, they’re the big elephant in the room. I get it. Most of you use them and love them, you’ll never leave ’em, and that’s fine. But I’m here for people that maybe want something different or a change and I’m here to help. And that whole takes the edge off of I’m here to help. 

And then I became a part of the community and I had relationships and talked with guys on Facebook for five years before they did a trial. I saw a trial pop up three years ago and I’m like, oh my God, I talked to that guy on Facebook eight years ago and I never sold them once. I just hung out. I just kept hanging out on the playground. That was kind of the play. I can’t say that was all intentional. That’s what ended up happening. I can’t say I didn’t have a crystal ball, but there was guys. I was just like, dude, you’re going to bite my head off every time I say anything, and that’s cool. I still love you kind of deal with it.  

Rob Walling :
Yeah. Yeah. And soles, people think your only marketing approach was Facebook groups. That’s what we’ve talked about for the first 10, 15 minutes of this show. Let’s bounce to SE because Tom had a question about that and he said, I did some quick SEMrush research on home inspection software, and it seems like the search volume is pretty low. So what keywords did you concentrate on to do your SEO and how did you find those keywords?  

Kevin Wagstaff:
It’s a great question. Good job, Tom. Doing your homework on SEMrush. We’ve all used it and love it. Yeah, small volume. So it’s a small industry just like imagined garage app, your wrap and sign addressable market is, and so I said we have to rank first for home inspection software. That’s the only game in town. We only had one or two keywords, and so it was a big hill getting in the industry saying, oh my gosh, home gauge and home inspector pro rank first and second. Everyone loves ’em. Everyone goes there. How are we ever going to supplant them? Turns out just content every day for years can bust through that when your competitors aren’t doing it. So YouTube is owned by Google second biggest search engine on the planet. So keep in mind good YouTube presence, I just believe has something to do with the main algorithm. 

I don’t have any proof of that, but I have to believe clicks and signals into YouTube help. So I made YouTube webinars, videos, any blog article turned into a YouTube video. Rob, you’re no stranger to creating content, so you know this. But then I looked at adjacent keywords. So I think s CMR is great if you use the magic keyword tool, it’ll give you adjacent keywords in kind of the next bubble out from the main keyword. And for me it was if someone’s looking for what association do I belong to? If I want to be a home inspector, what tools do I need as a home inspector? Hey, what are licensing requirements in Oregon for a home inspector? So I literally spent hours writing a master article on the requirements of every state to become a home inspector, and I got them from the state licensing websites, spent a whole day copying and pasting, and then I created that master article. That article ended up ranking first or second for home inspector requirements. So then I was getting them when they were thinking about being a home inspector, they were clicking on Spectra and I was like, you’re going to see our name when you’re just thinking about it. So hopefully six months down the road you’re like, oh yeah, for some reason I want to use Spector. So every industry I think has bigger and bigger circles of keywords  

Rob Walling :
As you talk. It strikes me that you had short-term results. And what I mean by short-term results is being in the Facebook groups, you were bootstrap and two founders, so you had to have some type of revenue coming in. You couldn’t just say, well, we’ll have revenue in a year. Let’s have a free plan. So you needed some type of, Hey, we need a couple hundred MRR or whatever it is, a thousand MRR each month to kind of grow. But everything you’re saying is, but then it took a year or two or three to work, and over time that snowball it paid off for you. Was that intentional or is it a hindsight thing of Well, it took longer than we thought, but we just kept grinding because we figured it would work. Or at the start, were you like, this is going to take a while?  

Kevin Wagstaff:
Yeah, so at the start we were like, Hey, it might take a year to get to the point where we can pay ourselves even a couple grand a month. And so in our episode, I briefly mentioned it, but I offered kind of marketing agency type plans to customers for the first year. So we were charging three to 500 a month for me to personally manage their SEO because that was my specialty and kind my background. So I had at any time between 10 and 20 home inspectors who would pay me three to 500 a month to write two blog articles a month to go to their website, optimize keywords, title tags, kind of the basics of SEO to signal to Google what your site’s about. And that floated us for the first six months a year where we had 10 20 k, let’s see. So it was like 500 a month, 10 to 20 customers, so whatever that maths out to a couple grand a month to at least cover our bills, float us a little bit. 

And then I kind of phased those out and told them, Hey, can’t do this anymore. Here’s a good recommendation to kind of pick up your SEO, like a local agency. I’d find them one to link up with as the software MRR started to ramp up. So it was kind of like, Hey, this is what I’m good at. I can contribute in this way, and then phased into the software piece. And then we ended up hosting websites as part of our offerings. So we have about 2000 websites that we host now, and it’s a great profit margin segment.  

Rob Walling :
Tom’s next question is about product-market fit. So he says, I ended up listening to some other interviews that Kevin took part in one of the interviews. Kevin said, you knew we had product-market fit when they had 10 customers. Was this the metric that you used to decide you had product-market fit or was it something else? And having 10 customers was just a side effect.  

Kevin Wagstaff:
Keen observation, definitely not the number of customers, but more about solving the critical pain point. Once I heard it from 10 customers and then they signed up, they believed we addressed that pain point. So it was more like, Hey, you want to save time on your inspections? I get it. Okay, what’s the main choke point here? Okay, it’s in the app. You’re spending too much time in the app tapping around that pisses you off. You want to spend more time with your family. Once I felt like we were on the path to solving that and people started signing up, that felt like maybe pain point market fit or a product pain point fit, however you want to word it, but I asked every one of them, if you had a magic wand and you could wave it and solve something about your software, what would it be? A couple guys said, I think I found that with you. I was like, okay, we’re onto something here. I took that. That was our marketing headline from there on out, their words, not mine, where I’m like you said you’re spending, you could spend more time with your family if we save you an hour. Oh, that’s marketing gold. I’m using that everywhere. Who doesn’t want more time to grow your business or to spend with your family?  

Rob Walling :
I believe that phase you talked about is problem, solution fit. It’s where you’ve identified a problem and the solution, it can be software, it can be anything. It doesn’t have to actually be code, but if you find that, then you can now say, all right, let’s pile more on or let’s write the code to do it. Sometimes it’s kind of human automation or you’re doing a productized service, for example, as the solution, but it sounds like you already were there where the code was actually was nailing it. Another marketing approach that worked really well for you was word of mouth and Tom asks, when doing word of mouth marketing, were you worried that you might upset your market and the criticism that would come when you started doing it, or were you just ready to roll up your sleeves and roll with the punches when you picked that marketing  

Kevin Wagstaff:
Channel? Tom will probably understand this well, but we did not understand the constant criticism we would get in this industry basically from everything we did at any time.  

Rob Walling :
Why is that? Tell me more about that. I’m not sure I understand why  

Kevin Wagstaff:
You’re going to laugh. So home inspectors point out what’s wrong for a living. They go into a home and look for up to 300 things that are wrong with it.  

Rob Walling :
Of course,  

Kevin Wagstaff:
They don’t point out what’s right. Every email, every decision product we’ve made, there’s been at least one person that tells us this is the worst decision of all time and we’re going to crash and burn and we should have listened to them. So you kind of get used to upsetting 10% or less of your user base or the broader market at any given time. I don’t know if that exists in other places and spaces. I know B2C can be more forgiven  

Rob Walling :
B2C when you serve software engineers or QA people because they’re the same thing. But software developers are the good ones who QA their own code or whatever. They’re super fricking detail and nitpicky I bet. Serving lawyers, right? They like detail. So yeah, there’s  

Kevin Wagstaff:
Doctors, lawyers.  

Rob Walling :
Yeah, there’s a few of these. So anyways, yeah, keep going with that.  

Kevin Wagstaff:
So yes, once we kind of started getting out there and just showing up kind of unapologetically, all kinds of criticism, all kinds of bullseye from people saying, your types come around every year. You’re not going to last get out of this Facebook group. You’re a vendor. Oh, you guys are just a cheap version of this, or you’re an expensive version of this. So I think the mission was always connecting with people and each time we talked to a customer, they saw a little bit of who we were. We lost money on so many customers that we spent an hour or two with talking, just learning about them and their industry and shocker, a lot of customer, a lot of companies neglect their longtime customers that aren’t profitable to them. So we talked to solo home inspectors that got no attention from their software. They didn’t talk to the founder of their company anymore. 

We were like, Hey, we got on calls, me and Mike. So I’m like, Hey, you’re on with the lead engineer and the lead marketer. Tell us your problems. Tell us what you want. But yeah, that creates word of mouth when they’re just like, Hey, Kevin and Mike are the real deal. They’ll listen to you. Oh, they’re chiming in on this thread right now. We answered so many fricking pointless threads, a hundred deep nested, no one’s going to see this. Someone’s always going to see it. So that’s the nitty gritty work where I’m like, that’s the grinder in us. That was like, that creates word of mouth.  

Rob Walling :
And did you try to get to a certain churn rate or a level of confidence in Spectra before you went that route? Before you started doing the real viral or word of mouth stuff?  

Kevin Wagstaff:
No, we did that from the beginning just because we witnessed another founder in the space that just lived in the forums and threads. So he was on the main association forum and Facebook answering everyone. He was everyone’s friend. Everyone knew him and respected him, and we were like, okay, we’re going to do that. So in a way, we just were like, that clearly works and resonates to connect with people one-to-one on social media where they are meeting them, where they are not trying to get them to go into TikTok or Facebook or somewhere else. So we saw him doing that and we were like, that’s the playbook. Just go do that. And churn was a slap in the face for our industry. We did not know it’d be like 3% a month. It was brutal. So once we started to see that survival rate, we baked that into our numbers and said, Hey, at any given point, a quarter of our user base or a third of our user base could go down. That’s scary. So we need to always be marketing and growing. And that was kind of my side of the house was like, that’s why I lived on Facebook, because I’m like, I have to get every new inspector that comes in the industry or at least win share, I got to get half of ’em.  

Rob Walling :
Is the churn high because they’re kind of people to do it on the side or the retirees and they just decide to stop doing it? They decide to stop being a home inspector or is there some other reason?  

Kevin Wagstaff:
Yeah, you’re onto it. It’s like there’s a seasonality and then there’s about half the states in the US It’s not regulated at the state level. So in Colorado you could roll out of bed and be a home inspector. So then you get guys that jump in, they do a couple, and then they’re like, I don’t want to work hard to grow a business, so I’ll cancel. So the cancellation and resign up rate was we couldn’t make sense of our numbers for the first six years.  

Rob Walling :
Yeah, totally. That’s hard, right? It’s like, well, they turned three months ago and now they’re a new, but they’re not new out of you. That’s always clunky. I’m going off script because we’ve talked a lot about things that worked for you. It seems like you generally had success with the stuff you tried, the Facebook groups, the word of mouth, SEO. Were there things that you and Mike spent time doing marketing wise? I’m thinking that didn’t work. Were there approaches that didn’t work and if so, how did you, I get this question all the time. How did you know they weren’t working? How long did you give them until you made the decision to stop doing them?  

Kevin Wagstaff:
Paid ads never seemed to hit for us, and it might’ve been the lack of expertise and sophistication with targeting and kind of the full stack setup, but running campaigns out of Google and Facebook paid tended to result in tons of clicks, tons of wasted spend. So it was kind of like we looked at that channel for a few months. We gave, I think we did a three month pilot and we were getting clicks from bad keywords. We didn’t dial in the right negative keywords in Google ads. It was like we were getting car inspection guys and things like that. But then even once we dialed it in, we felt it was a lot of people just clicking around late night, maybe not as serious. And so we just kind of tracked that to conversion and said, man, we’re batting one for 40 here, one for 50 not to, it doesn’t justify the spend. So we cut that. That was never a good route, was paid acquisition. It seemed like a product where people would kick the tires on multiple softwares, not necessarily be ready to buy right away. I need an email marketing tool today.  

Rob Walling :
And also we talked about in the interview that your annual contract value just isn’t that high paid ads, especially Google, you just need a lot of money and I believe yours was, there’s a thousand and then there’s a 2000 and a 3000 a CV depending on if you stack things or something, but it’s just not that much if you’re going to try to buy AdWord.  

Kevin Wagstaff:
Yeah, lifetime value’s got to be up there and the tens submit hundreds of thousands to really spend that, and we knew we could go meet these same people at conferences and they’re in the field working too, so a lot of times our demographic was not online all the time, and so it kind of made sense. Affiliate marketing, we also failed at where it was working with some of the biggest associations and partners in the space. It was like, here’s our affiliate link. We’ll share 10 or 20 bucks with you. It was kind of peanuts at the end of the day compared to just going to another conference making relationships or writing, making 10 more YouTube videos. And to me, we watched the numbers over months and then we tried to boil everything down to math, which I think most founders can appreciates. What does the math say?  

Rob Walling :
Last question from Tom. You mentioned that the home inspection industry is really slow to catch up on technology. Are you ever worried about someone being offended by hearing this? I feel the same way about my industry and sometimes I catch myself about to say it in a demo, but I stop myself.  

Kevin Wagstaff:
I want to ask you after this, Rob, if you’ve said things that have offended people throughout your journeys, you said a few times I knew they’d probably be offended, but at the same time, I also knew if it was the truth and it was something I observed and was undeniably true, that it would be okay to say because many of them admitted that to me. They’d be like, Kevin, I’m not a techie. I don’t know this stuff. I rely on you guys for that. You guys are the nerds. We were like, yeah, we’ll be your nerds. We were just like, cool. We kind of branded ourself on let us be Your technology stack was kind of how we talked to them of like, dude, you build garages, you inspect homes, you do whatever. These trades guys, they want to outsource all that to us, so let them and be upfront about it. 

And yeah, the competitors probably did not like me out there saying that of like, Hey, there’s not a single good tech solution in the space. I’m marketing my business, man. They can go out and say their message, but if we are getting our ass kicked by a ServiceTitan, I’d probably say that too. I’d be like, man, ServiceTitan does everything. We’re going to try and compete, but they’re crushing it. And yeah, occasionally you put a little spin on things to help your company, but I was okay with that and I got slandered for it. I took my licks.  

Rob Walling :
Yeah, the thought of, well, specifically I guess the phrasing that Tom used is you mentioned that the home inspection industry is slow to catch up on technology. To me, that’s not an offensive statement. That’s an industry as a whole. I will hear here I am on the podcast. Do you want to hear me offend people? The legal industry tends to be more laggards than not certainly any type of trade. I mean, my dad was an electrician for 42 years. I was an electrician on and off for years, and my brother runs an electrical contractor. All of the trades, all construction mechanics, they focus on what they do well, which is fixing with their hands and building things and do they really want, and it’s a generalization, but it’s like if you look at a bell curve maybe, or distribution across folks who are electricians versus folks who are web designers or something, it’s like how many of those folks really want to get into software and are interested in it and just have a high acumen for it and mess around on their computer on the weekends? The numbers are different. It just is, right? So I don’t think it’s not that you’re saying one individual now, it’d be offensive if I said, Kevin, you yourself are really not technically adept or whatever. Unless you were like, yeah, no, I totally am not, then it wouldn’t be offensive. But  

Kevin Wagstaff:
If it’s true,  

Rob Walling :
Yeah. So I don’t know. I wouldn’t be too concerned about this, especially if you’re talking about an industry as a whole, my guess is most people probably would agree with that. I guess the thing though that you then touched on, which was almost a separate thing, was saying our solution is the best and there really isn’t that much. Really isn’t any good tech here now that could be offensive to competitors? And I mean lightweight marketing automation that doesn’t suck was the H one of Drip for years. So what does that imply? That implies, and then  

Kevin Wagstaff:
I remember that.  

Rob Walling :
Yeah, and then I named, because I wrote the whole copy for that long form landing page, I named Crap, who was it? It was Infusionsoft. It was Marketo. It was part up by name on that page. Now, I did not name MailChimp. I always thought they were good tech, and I did not name HubSpot because I thought they were good tech and I’ve always respected as founders, but any of the other marketing automation I would throw under the bus, did I offend them? I don’t know. Did they even pay attention? Was I just too much of a gnat for them to even bother with? Who knows? Did somebody probably read it and say, that guy’s kind of a dick? Maybe it maybe happened, but did I believe it? Did I ever say anything on that homepage that I didn’t wholeheartedly agree? I was so passionate that why are you screwing your customers? This pisses me off that your software sucks and you overcharge for it, and you force ’em into annual contracts. You don’t let them see the software touch it until they’ve paid you for the whole year. So anyways, yeah, you can tell I’m getting off on a rant here, but  

Kevin Wagstaff:
Yes, but you spoke what you knew to be true, and then you could back it up. And as long as you’re saying what you believe to be true, if someone calls you on it, if you just show up and say, am I wrong here? Let’s look at it together. I’m happy to be wrong, but does this suck? Does Infusionsoft suck? Is it hard to use? Yeah, I don’t think they’re bad people,  

Rob Walling :
But I don’t think the tool is good and I don’t like their sales model.  

Kevin Wagstaff:
Yeah, yeah, yeah. Depersonalize it. And I just love that you stood kind of on what you knew to be true and you weren’t afraid to say it. And I think it takes a little bit of irrational confidence maybe before we were big boys, but you got to be okay taking that risk because it forces us to step up then right? Then you were like, I better make sure Drip doesn’t suck. I got to make sure that’s the thing.  

Rob Walling :
I’m calling my shot. I’m opening myself to attack now. Right? It better be amazing and it better without a doubt be better than these things I’m calling out by name. Yeah, there’s a certain amount, and I’m not a conflict person. I don’t enjoy it. I can do it, obviously I have to sometimes, but it’s not my wheelhouse. It’s not like a strength of mine. I know friends of mine who are really good at it, they love debating love, getting an argument or even just conflict just ignites, ha, I can be right about something. Me, I’m always like, I don’t really want to get in a fight that feels like a waste of time. But I was always willing to risk that and to do it and defend myself and my company if I knew I was right about it. And I knew much like saying lightweight marketing augmentation, that doesn’t suck. It’s not just marketing, but it truly was a stance that we were taking. That’s what Drip, when we came on the scene, we were like, all the other platforms are kind of mediocre guys. And our whole thing, our USP, our positioning, our whole positioning was based on that. And so that’s where I was willing to go to the mat for it because it was important to differentiate ourselves in the sea of competitors.  

Kevin Wagstaff:
I love that you said that because for you guys watching and listening, I’m the same way. It’s not like we are just like cocky, brash, and we came out that way. I’m very conflict avoidant and was even more so at the beginning of this spector journey. I grew up a people pleaser. I was that kid in my family, and so it hurt me. It made my heartbeat fast. Every time someone would trash me on social media and people would say things about the software and me personally, and it always hurt every time. And there was times I quit going on Facebook for five, 10 days at a time to regather myself and get my confidence again. I hated it. I hated conflict. But I also realized I had to find my voice the way you just said you did of maybe not finding it, but you spoke what you knew to be true. My self-growth journey throughout spec Torah was like, do your homework and then unapologetically say what you want without being a dick, and that’s possible that you can do that. And so I thought about my wording a lot. I got reps on camera the way we’ve both done over the years on YouTube. So it’s like I got used to saying things in a certain way where I was like, Hey, I’m not being a here, but I just objectively think we are better and here’s why. But I’m happy to debate it. Happy to talk about it.  

Rob Walling :
Kevin Wagstaff, thanks for joining me on the show again, man. It’s great to have you.  

Kevin Wagstaff:
This is so fun, man.  

Rob Walling :
It’s cool. It’s neat to be on the other side of the AirPods, huh? Because you were a long-term listener and is it weird to be on the show now? Did you listen back to your first episode?  

Kevin Wagstaff:
Not yet. I’m scared to, but I was around listening. I remember I went back and listened to the first, yeah, I went back and listened from one, I think years ago when I first started listening first episode. So I’ve been in an OG for a while, but I get energy out of just talking about in retrospect now to our past selves, if that makes sense of us 10 years ago. It’s so fun and humbling, and I just want people to all crack their industries and win such a fun journey.  

Rob Walling :
Well, it’s great having you on the show, man. If folks want to keep up with you on X Twitter, you’re Kevin Wagstaff three. That’s the number, Kevin Wagstaff and the number three. And I think that’s it, right? You’re not on LinkedIn, you don’t do, don’t have a main website you want to send people to.  

Kevin Wagstaff:
Nope. Just there. And then if people have more questions, they can find us or they found us for this one, find us on the Twitters.  

Rob Walling :
Awesome, man. Thanks again for joining me.  

Kevin Wagstaff:
Awesome. Thanks brother.  

Rob Walling :
Thanks again to Kevin for coming back on the show so soon. I really enjoyed our conversation. I hope you did as well. And if you keep listening, I’ll keep recording. This is Rob Walling, signing off from episode 786. You found the hidden track. Kevin and I are going to talk a little bit about his experience as an athlete, a college athlete, and then you played pro ball. Tell us a little about your experience, but the reason I want to get into it is I was also a high school and college athlete and it had a huge impact on my ability to be an entrepreneur and succeed at it. And so I want to hear a little bit about your experience around that too.  

Kevin Wagstaff:
Yeah, I’m such a believer in it. It doesn’t just have to be athletics, but it’s what we share in common and what we’ve drawn from. But it was just something I was so solely focused on basketball from age eight basically to 28 to basically when we started Spector something, I lived, breathed. I always was a repetition person. I wanted to be really good, and my parents just said, Hey, if you want to be really good practice. And then somewhere along the way I got really inspired and motivated to hone the craft and spend time at it. And so when you spend so many thankless mornings and nights lifting with the team, working out, shooting, staying after practice, you just kind of get used to refining something until it’s good and sticking with it. And I read a very pivotal, I’ll get into this in a second, but played college basketball and then had a chance to play on a semi-pro team in the Philippines afterwards. 

Did that for a very short stint, came back home because I had a young daughter and realized I’d make more money with my brain than playing basketball. So said goodbye to that dream, had to disassociate from the athlete in me and was kind of had a few years of being lost in a way of that athlete identity until I came across a Mark Cuban blog post that talked about business being his new sport. He liked basketball and he only played in high school, but he said, business is 24 7. And the way he talked about it, I was like, oh my God, I could channel the sports mentality into business and get rich doing it. This sounds incredible. So then it was more just finding the what and kind of had to abide my time until we found the thing that I could really be a psycho about the way I was a psycho about basketball.  

Rob Walling :
Yeah, obsessive.  

Kevin Wagstaff:
Obsessive. What about  

Rob Walling :
You? Well, when you say the sports mentality, I’m going to tell you what that translates to me, and you can tell me if you feel the same way to me. Academics were always easy. I read from the time I was like three years old doing math in my head, whatever. All that stuff kind of came easy. Sports were really hard for me. I’m not physically naturally gifted, and so I was slower than the other kids. I was skinnier, I was weaker. I couldn’t push as much weights as anybody. And I played football and ran track and all this. The big thing with sports for me is I would work day in, day out with basically no positive feedback loop for weeks and then months. And then I’d have that first meet if I was running track and I’d get the first feedback loop of, oh, I’m doing okay or I’m not. 

And then the next week, then I’d have another feedback loop of, oh, I’m doing better. And whether it was just pure time-based or whether it was placing in the races. But the thing there is this ability to have delayed gratification and to work towards a goal that is months and months out now, I never thought, I mean, I ran track from the time I was, what, 14 until I was 23 through college. So I wasn’t old enough to, I never thought in terms of years, who in three, four years I’m going to be better. I just didn’t think that far out. But I definitely thought out, Ooh, in six months I’m going to be faster. In nine months, I’m going to be faster. And I didn’t play instruments growing up. I didn’t do anything else in my life. I think that had such delayed gratification till I became a founder, till I became a, well, at first it was a blogger where it’s like I got to build an audience over a year or five or 15 podcaster. But being an entrepreneur was where it hit me. So that’s when you say sports mentality to me it’s like, no, I’m going to put in the reps even though I kind of have nothing to show for an extended period of time.  

Kevin Wagstaff:
Does that resonate with you? 100%. And to build on that, some of those reps, I imagine you pushed your body to a point of near failure and exhaustion to be great.  

Rob Walling :
Yeah, I to throw up every week or two in the early parts of the season.  

Kevin Wagstaff:
So once you push your body in a way that’s physical pain, you feel it. Whereas emotional pain is different and it’s sometimes harder, sometimes not as hard as physical pain. And so that’s why by even working out, working out, pushing your body, once it’s pushing your mind, then you’re like, oh, I could do this. I got energy left in the tank. I got renewable energy here. I can keep going. You find levels within yourself to just say like, oh no, I can push harder and not let it ruin my day or impact me because you’ve done it physically. So part of it was, oh, we’ve pushed ourselves way harder. We got this.  

Rob Walling :
Yeah, that was something I thought of often. The other place where I think this holds up is learning an instrument over the course of many years, which I am not. I play the guitar, but I’m not that good at it. And so I never did the hardcore practice, but my kids when they were younger, Sherry, and I said, you will do something hard every day. You will either do a martial art, you will play an instrument, or you will play a sport and you will do that six days a week. And I mean, that’s pretty brutal. We’re just like, no, no, no, no. And it’s not because I want you to be a concert jealous and violin, which is what they play, or that I want you to be a black belt martial artist, or that I want you to be a track athlete. It’s that I want you to know what it’s like to build something over time and to do hard you don’t want to do to have a payoff years from now,  

Kevin Wagstaff:
Man, life lessons in a world that just keeps moving quicker. They are going to be well equipped. What would you say, Rob, to someone who didn’t play sports? Because I’m always curious when I’m like, man, it’s so natural to us. What would you say to someone who had other things?  

Rob Walling :
Well, and that’s the thing, there’s a bunch of TinySeed founders who, a bunch of founders I know who are super successful that I don’t think played sports as a kid. Anybody that I’ve had on this show, I don’t think most of them did. And so I think there are other ways to do this. I don’t think you and I should frame this as, oh, this is how you’re successful is if you played sports. I don’t think that’s it either. I think each of us has our motive. One, you need some motivation. I think there has to be a goal. My goal was to make enough money that I had some type of freedom and I wasn’t worried constantly about money and then, hey, I can quit the day job and then hey, I don’t have to work again. That was a strong goal. So that’s the first thing. 

But the second thing is I think you need some type of intrinsic motivation. And I think if you played sports, you know what that is. But I think some people are also just intrinsically motivated to do stuff. And I don’t know if that comes from upbringing. There are some folks I know who kind had to get a job from the time they were 12 or were working from the time they were 10. And to them, work was just a part of life. Doing work that you didn’t want to do was just it. So I think that could easily be it. So I think there are many paths. I just think sports is perhaps an ease. It’s really easy to see the comparison in the through line.  

Kevin Wagstaff:
Yeah.