#210 – How to Take On Huge Incumbents as a Solo Founder with Derrick Reimer of SavvyCal
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What's up, everybody? This is courtlandt andi hackers that com, and you're listening to the any hackers podcast. More people than ever are building cool stuff online and making a lot of money in the process. And on this show, I sit down with these andy hackers to discuss the idea as the opportunities and the strategies they're taking adventures of so the rest of us can do the same. Dirt, grime, welcome to the show.

Things are have me it's good .

to have you on you're like you're like one of the people who are like going the most ten gently connected to through the podcast because like i've had you are podcast cohoes to be orange in on the show at least two or three times now, yeah, i've had your X O founder, rob walling. You guys started the company, dripped together on the show like three times now, yeah and this is my first time you yeah no IT feels like it's a long overdue like.

you know me to figured was about time, about time to come on and officially meet you. I ve been fan of your work for a long time and obviously aware of you in the india cki s community. So thanks for yeah, happy to be here exactly .

just talking to rob and he's suggested you come on the show is like why you have dicon and why do I have and bans at the same thing the last time used on the show today you're working on savi. Ca, yeah, which is a super cool APP. What is savi?

C, exactly. yeah. So saw is a is a scheduling tool that allows you to basically create a scheduling link and send IT to someone else and show your availabilities attracting out when you're already busy on your calendar and basically coordinating A A time to meet.

And we kind of have some some fresh takes on IT. Obviously, it's it's a well established category. There are a lot of different tools in the market. And so we kind of have some particular opinions about about some fresh ways to do IT.

right? And I know you're not like super transparent with the revenue numbers, but like you told me you're willing to give a ball park. Where are you add in terms of like your success and growth was savka?

I mean, my milestone that i'm driving towards is official like default ve status. I guess where I can I can like pay profitable on paying my salary and all the expenses of running the business. And we're right about there. So we crashed across ten k and headed to twenty k. Mr, so that's like the most exciting place to beat.

Yeah then you can like are looking into your future. But what I want to do, you can do anything right? exactly. And because essentially your life is in your own hands now you're not accountable to anybody for your financial independence and then you got to make some tough decisions you don't want to keep making this bigger. And when I want to shift directions, I want to hire and growth and want to keep IT going to the sam Epace. Yeah.

that's what abandon I on our podcast. We keep like the last couple of times we've recorded, we keep coming back to this kind of central question of like all roads lead back to what do I really want out of this business.

And figuring that out is actually very difficult because me, like a lot of the hackers and founders of bootstrapped acquires I bootstrapped companies like we kind of hold intention this this ambition to grow something big, but also kind of maintained A A healthy baLance and a calm a calm working environment. Sometimes those two are intention with each other. So it's it's always a fun game to figure out.

And sometimes the changes, you know like early on, you might be like, I just want healthy, sane baLances. I want a great life and then you like, get to that point and you're like, I want some chAllen. I want to like, go for something bigger and more chAllenging and like, that's totally Normal for things to change once you one particular goal.

So i've listen to you and been on your podcast, the art products, an excEllent show in your form that is kind of just like as then puts IT two dudes talking you. And back when I was listening at the beginning, you're working on your company level and ben was working on tube and I was as we reject the position because tubal was taking off, like ben was like making money hand over fist, like I was just super jazz, everything was going well. And then you're like in this kind of like sad, sad, depressed the state, you're like, uh, my company level is like not working.

What am I going to do? You're trying to saw agit IT was just such a jacker sim between the two of you and I felt like bad listening to to you because I really helped direct makes you like I hope he figures is out because ben's doing so well. I like now seeing that you have figure things out with your next company's savi oc. It's all good, so good vibes. It's almost Better listen to like a failure story, like a success story comes after.

yeah when you know there's light at the end of the tunnel yeah, yeah, trust me, I was yeah, he was mentally difficult. I think something that we really strive to do on our podcast and I think is an important like responsibility of working in public, is trying to show both sides of the coin, you know, and and not just project the the good things, but but hopefully tell the raw, honest story about what's not working well.

And but yes, I IT was difficult to show up on the night every weekend, especially when things started to get real, started to really come to ahead online. Okay, I think I think i'm going to have a lot of trouble bringing this to market, getting getting real customers. What do I do? Now one of the parts we can probably dive in that story a little bit more, but like one of the parts of the level journey that being able to deconstruct what went wrong and kind of lay the whole story out there, and you know, obvious ly, you can learn personally, learn a lot from from your own fAilings. But then being just making the decision to, like, be open about that IT IT made me feel good that potential I could help some other founders who might run into some of the same, same road blocks that I did.

I think it's what's going through like the story of level and then the story of savka because, I mean, haven't been working on savka for that long. You started at last year. You're already passed the ten k on the revenue mark is super cool.

So I want to look look at the differences between like why did one business not work and why did the other business? Like why is that working so well? And so maybe the place to start is at the end of your very first business, I am aware of trip. You started a trip was an email marketing tool you built with a rob walling, widely successful. You guys got acquired by lead pages, I think and I don't you never share like a revenue numbers, but I imagine like you do is pretty well and you're sitting there, you know, earning your money going to earn now you like what the next thing to do is how did you decide like what to do after you sold your company?

Yeah so I kind of had this is like during my time of of working trip and then and then lee pages. Lee pages was a team of one hundred and fifty people, and we were like a team of ten. So we kind of got absorbed into that.

And suddenly, like I was in A I was in a slack workspace with over one hundred people in IT and watching kind of everything, all the business kind of increasingly being run on slack. And we are sort of not fully in the office all the time together. So a lot of stuff, a lot of communication being pushed onto chat as a medium. And I became very, very intensely aware of all the ways that, that is a chAllenging environment to work in without a lot of discipline, right? So so even even though we tried to all be respectful of each other, other's time and attention, like I just I was having a heck of a time trying to trying to not constantly drop the ball and and get distracted by by slack and this was like two thousand .

and fifteen and two thousand and sixteen or something when slack was like relatively new to catching on.

Yeah, we've been slacked users for a long time. But of course, when you're a team of ten, it's everything's just easy. Most conversations are in the general channel and it's like no big deal.

And then you just get then you get all kinds of different styles of communication all mashing together and IT kind of becomes chaotic. And so I sort of had was forming the hypothesis around like, okay, I obviously remote work is is here to stay even at that. But now it's more so than ever.

But even at the time that, that was a growing trend. And so I was kind of sensing that there was increasing need for good tooling around to facilitate acing, Chris communication and remote work. But I was just pretty well convinced that slack was not the the end of be all that a lot of people who are making IT out to be and that we could do Better on the product front.

So I couldn't get that out of my mind and I was leading up to what felt like the natural stopping point for my for my ten year at drip like we we had successfully transitioned to the new team and and I just was feeling like I was time to to move back onto something. And in retrospect, I would have done this little differently. I didn't take any kind of break at all.

So literally the week that I left is when I sort of published the level manifesto, put that out of the world and started started kind of talking about the the next act. And I would have been bet so well, served by a little bit of downtime to just step back. Just think think really hard about this and check my assumptions. But but there easier.

easy sadden done yeah especially when you're super excited about the next thing. And I know a lot of people who like solve their companies and made a whole bottle of money, and they are suddenly in this position where they have to decide like wet next. It's kind of similar to they get into the ten thousand dollars a month market, okay, what next? And it's like generally four approaches.

It's kind of like, number one, you graduate like the next level in your field. So for a lot of founders, that means like, okay, what's beyond a founder? I guess i've become an investor or something that's go found a rob did now is a confest lots of money to start ups.

Number two, that you can't keep doing the same thing, but maybe you get like a little bit more ambitions to do something different. So that's kind of what you're doing. Like now I still want to be a founder like I want to keep starting companies.

This is what I love doing. Like let me start another one. And then there's like a third and the fourth option. Option number three, switch industries entirely. Just like god become a writer or an actor or a painter something and just be like i've done.

This the number four is like retire, go live on a beach, do nothing which to be on the sign of the year of people who've one people who say they are going to do that, they just eventually do something else like IT doesn't still work out that way. What even think caused you to go down like the second path of continuing to be a founder? What even is differenced you and rob, who decided to be an investor? Like what drive people down either road?

Yeah, I think, I mean, I think rob, he robs about ten years older than I am, and he he kind of had a heads start in in the industry. So I he was a mentor of mine. I looked up to him.

I read a book before we started working together. He was fun. And so I feel like in our conversations, I always teazed him like you're you're going to want to get back into the game, you're going to want to SaaS company.

But I mean, as we know, these building these companies is a IT takes a lot energy IT takes a lot out of you ah can be pretty stressful the highs are good. The loser are pretty tough to deal with. And I think rob is feeling like i've done that like I feel I feel good.

I hope he's list ting robbin and an all guy a different you ve had your type yeah and .

I feel like he's kind of get the festival the worlds. Now as as an investor, he's an invest savka and lots of other companies. And so now he gets to lend his advice where IT makes sense but without having to fill all the ups and downs, right?

IT has got a nice as an investor and advisor, or you can give high level strategic advice, but then, you know, have to set there in and out, like two hundred cold emails like you'd do not doing, like the sluggish, like thankless work you're doing, like the fun stuff.

Yeah yeah. So coming out coming away from the job acquisition, you I feel like I more more products in me and also just the ambition to to build something meaningful. And he was it's of a test for me, like before a trip I experimented with with a couple of failed attempts at startup.

S I was just shortly out of college and spent a couple years like making all kinds of mistakes. And the classic mistakes of not validating things in advance are focusing on marketing and all that kind of stuff. And then kind of took this journey with trip alongside rob and build a product on the side while doing trip, which felt like a little bit validating because he was something that I sort of brought to market and saw a little bit of a little bit of a success for me.

I wasn't a knocked out of the park, but I was a IT was a nice like little mini exit. But to me, it's like I filled the chAllenge of like, okay, this is my this is my time to step up and be the founder of something on my own and and see what I can do. So I do take IT a little as a personal chAllenge to.

yeah, that makes a lot of sense, especially like once you get like rob talks about staircase, you start with something small, take that first step, you get something like a little bit bigger like once you have these ones under your bell like IT feels so much more compelling to just do something a little bit more ambitious and kind of like I don't almost like prove yourself to who like I don't know maybe to yourself, but I felt the same thing like a well, like I need to prove like even then the early days of andy hackers, I was interviewing all these SaaS founders. You were making money in the after any hacks and you just start my own suspence it's improve that I can do the same exact thing and the questions going like why you know why I do .

this yeah it's funny. It's it's a very I think it's maybe something in founded DNA, something in transit to us that just drives us to do these crazy heart endeavors. I'm not sure what IT is.

Would you described yourself as like a competitive person?

I would say i'm moderately competitive, but i'm not i'm definitely not the most competitive. I'm friends with I A friend who's in like sas sales and that gives me an example of someone who's who's very compared, always kind of playing the game, the game of the chess game of of of business and SaaS.

And I feel like I do feel get competitive about the the areas where I feel like I have I have a potential edge like especially when looking at kind of big and commence in the industry. Don't know a little bit of the David and gliff dynamic. That's what really kind of motivates me.

And you going to have that with every company that we're talking about, like a trip OK email marketing in an industry was like a male champ already existed before you start a trip. So like you were the dave and they were the good life.

And then level, okay, like slack was already a huge behemoth and you create levels sort of take on like the bigger guy and then savi cow, right? Like talented and the q ity like is already big scheduling software. And here you are making like a very new entrance. So IT seems to be like the the framework that you love the best is taking on .

these huge players. Yeah.

I would say so. So now you're at this point and your story where you have left trip, you're like i'm ready to do something else, someone to keeping a founder. You've got more ideas than you and you end up deciding to do level. You publish this manifesto that's kind of like anti slack describe to me this manifesto because, like, not very many businesses start with a manifesto I think probably more good. But IT worked really well for you.

This very much spoke to a problem that I think people felt viscera ily. Especially specially people who consider themselves to be makers, right? A sort of this undertone that I was detecting of, like a very deep dissatisfaction with interrupted ways of working.

And that is sort of the that sort of the natural way that a product like slack works like it's just sort of designed to send you push notifications and and be immediate like this sort of baked into the product and at the time they're float around to turn all like slack lash or whatever, like this kind of kind of growing grass roots movement towards like trying to put up defenses against slack. So the manifesto was like, remember when you first signed up for slack and and I sort of have walked through this little story of like at first I was good. You were just there was just a few of you and you would chat.

And then over time, things started to evolve. And I kind of just the story that people could walk along with and really and really feel. And that seemed to resonate a lot like a lot of several thousand email addresses over the course of of a few months.

Lots of just kind of anodos validation from people saying like yes is such a big problem like I can't wait to see what you're going to build. I would love to use IT with my team. And so the indicators were like looking very positive initially.

And user validation is super important. And mark validation, and I was aware that like getting trying to eliminate biases from that was important. I think I didn't quite have a fully mature framework around how just too like route around that, which I learned the hard way because I collected three sales, did bunch of interviews, try to speak to the underlying problem and not my proposed solution. And yet, as IT turns out, as I learned once I had an MVP really like the actual market response is quite different than what I was hearing yeah .

idea that like people were super motivated to regio manifesto that like there is the slack glassed and everyone's talking about like distraction at work and everyone's talking about interruption freeway. I mean, I literally just got a significant ation while you are giving a speaking term sepper distracting, right? Like everyone knows it's distracting and there's this kind of patter.

I think whenever anything gets bigger catches on, it's kind of predictable that there will be a backlash. You know, okay, social media is big. There's gonna be a bunch of people who hate social media.

Cell phones are big, going to be band who hate cellphones. And then I tend to fall into the camp of like the counter counter contrarian. So it's like whatever comes out, everyone hates IT, and I hate the be able 的 just because for no other reason ah。 And so like I i've embrace all this distracting step. Like the result is like i'm constantly distracted.

Why did you decide to like, write a manifesto? Because are so many different ways that you could potentially launch a business or test out your idea, like the only other people I know who have really started with like a manifesto, or people like john nolan from ghost who wrote a manifesto against a wordpress and everyone piled ongc. I'll hated wordpress. And one is something Better, I think, ben, also, to all sort of like a rid of manifest, told against, like slack acquiring screen hero. And like that was kind of like that, something attacked into like this anger that people felt like, why did you feel like I was a way to go?

I felt like I was the power of story telling. I've kind of learned that over time, through podcasting, through just watching, honestly, like watching kind of robs example of marketing drip. And we always, for the longest time, we just have like a long form sales letter as our trip home page when Normally people would have gone to the traditional like sah home page with a little block up in the hero and all that, we just had a bunch of text.

And so like rab has always been very um that was sort of his style was to be very kind of like story oriented and and kind of more traditional like sales letters type type of stuff. And so that was sort of my background too and I just felt like telling a compelling story would give me an indicator on whether people were really like nodding along with this. And if I could get people nodding along, then I felt like I felt confident that I would have a market to didn't quite pan out. Um and so I think I really want to bury the lead too much but like kind of the big takeaway was that people lie to you for your best.

what they think are .

there have your best interest in mind. They're trying not to hurt you and they want to be encouraging. And I think people aren't totally aware of their own purchasing dynamics either. Like so in this case, I had a lot of. Managed to convene a lot of like champions in companies to to really buy into the the vision right and totally resonate with the the idea of saying that like slack is distractor and and I want something Better organized.

But a lot of those people, one didn't have necessary have buying power and did necessity have the cloud inside of their organization to get the buying from literally like every manager or every decision maker who would need to be on board with lake, ripping out the guts of their whole lake company community platform. We replacing with something else because is not something you can exactly double and you can't just like switch part of IT because then you still have to keep slack. If everyone everyone else in the company still in slack and some other department may reach out to you there, like you can either run both in parallel, which is just sort of worse um or you have to convince everyone to switch over wholesale.

And then I think also like just a lot of the people were willing to complain publicly and tell me express that they they agree with what I was putting out. But ultimately, like IT wasn't enough of a problem for them to go through, jump to the friction of switching right. And all of that I probably could have sussed out earlier on, but I was sort of I blinded a bit by my own optimism.

And I think if you get a bunch of people like the called action, the button manifesto was sign up for, basically you get a lot of people who are all like, yeah, feeling you directly. Like this is exactly the problem I experience. And you have like this like an eight sound optimism too. Where you're like this is it's going to be so good, it's going to be very successful on about this cool, amazing thing. It's like really, really hard to kind of like summer down and like cut through the noise to figure out the right question to ask, to make sure that people actually will by this product because IT doesn't matter if like people agree with their message from matters, is that they will like take out their credit ard and pay the monthly subscription fee for whatever you build.

And one of the one of the resources that was shared with me kind of later on in the level journey was sort of an eyes opening moment when I read IT, a book called the mom test by rob z. Patrick should be required reading for every founder who needs to talk to customers ever because it's not not just for early product validation, but even I think for the the process of like sussing out doing A A customer interview and figuring out what are people really asking for what's underlying problem is how badly is that problem affecting them? IT just gives you a framework for basically asking questions that are so bullet proof you could even validate an idea with your own mom, which is where ah the title book because I love .

that concept because your mom is like the person is going to be the nicest TV she's going to tell you everything you want to hear going to be anything about my start by dm mom and you can be like, it's amazing might take away from the mom test and i've had rob, that's patron, the show to talk about IT it's unna you like we joke is like the episodes about an hour long. And that's also about how long IT takes you to read this book.

It's super small. It's zero to the point that you could just skip the evolution, get really book. But he's really all about asking for proof that you don't ask somebody.

Would you use this? And what do you think about my idea? You asking them questions like when was the last time you paid to solve this problem? Or give me an example, if I can alternate your product, you're using IT SATA. And if people don't actually have the receipts, then they probably are not serious.

yes. How did you figure out that uh.

level people aren't serious because I mean, there's a decent amount time in the past between you writing that manifesto and getting all these e mail sign ups and you learning that like favors might not be the right .

idea yeah knowing when to pull the plug g is is hard and when like went to dial bacher own optimism and kind of face the reality right yeah so after reading that book then I I basically took a step back because I was kind of in the mode of like trying to trying to recruit people off my list to sign up, become paining customers and and use the MVP and was really struggling hard like I made IT through a good chunk of the list that had been most engaged and was not really getting any bites.

And so took a step back and started doing some more more rigorous interviews, applying the mom test and hearing just a lot of red flags, a lot of like, well, yeah, I mean, I haven't actually looked for an alternative solution which is that one of the big things like ah you have you paid for anything or have even done like a google search like slack alternative and like no no, not really because you know we're so entrenched and so I started to hear that stickiness just come up over and over again. And the funny thing is like I still think that it's a viable business in some form under certain conditions. I think that there and there are there are others.

There's twist from from the to do ist team. They've been around since a little bit before I start work on level. I think and I think there's they've been somewhat public with their numbers. It's been a kind of a slog, but I think they are they're gradually growing and making some inroads. So I think it's like a viable problem.

But then the question becomes like, is IT viable for me as a founder under the constraints that i'm willing to Operate under? I was not willing to raise traditional venture capital to do this. I think that maybe what I would have taken just to have more, more time, you know, money gives you more time. And yeah, I think I would take lining up the timing with a certain wave of momentum in the industry where there's enough people dissatisfied and willing to adopt something else. And so I just kind of determined like after doing those interviews, I was after a year into IT, and I just felt too risky to basically take another what I felt I would be maybe another year or two of effort to maybe yield a business that's viable.

Yeah, I am already talking about like building building at level and you're just talking about like I need to build you this feature and that feature and like you can suck into this point and it's a potentially endless slog of features that you need to build to make customers happy. And and you were a sort of retrospect cc of blog post. You talked about the fact that they're actually kind of like maybe two profiles of customers.

They were like the really large teams who are like slack sucks and it's super distracting. But we're not going to switch to you like newly built solution unless we have like these thousand features that you don't have yet and like, well, you don't necessarily have the resources, the time to build that. And then they were like the small teams who actually could use something really small and simple, but they didn't feel the pain of slack because like data, small teams.

So I wasn't that distracted like me with andy hackers and I would get like four or five people on our slack and it's super easy and then I switch over to like stripe slack and it's like this chaotic bees with like ten thousand channels and it's like what how who do you build for? If you build for the small teams, like you can build the product, but they don't care enough to switch. And if you build for the large scams, like you're never going to actually be able to build all the features that they need is by the time you're done with that slack will be so far ahead like you're just it's not going to damped if you do damned ed, if you don't, so what what do you do when you realize like, okay, have been working on this for a year.

It's not working out. I don't really have the patients to try to build this product for these large teams. Like how do you reckon with that as .

a founder when you went to cabin in the woods, step one, which I did, I actually did, I went on a little like retreat. So it's like, okay, I need to, I need to become comfortable with this decision.

And I can either, I can either have a freak out moment and completely retreat away from from this endeavor, or I can kind of just take a step back, breathe, evaluate and try to get get a clear mind to make a decision on this and um and that's what I did and I actually um I actually spent time writing that that retrospective post um and I started took me a couple days of of just kind of working on IT and and just doing other reading and hiking and other things to get my get my mind clear and I felt like by the time I finished that I was like if I can if I can write retrospective where there is a clear kind of um there's clear logic to to the decision and at the end of the conclusion at the end of this post is that like, yeah this is why I made the call to move on like if I could compose this then I would feel comfortable in me that that I was actually ready to to call IT on IT. And then the bonus is that I got this deliverable on the other side, which was A A post that I could share with the community that did get a lot of positive response. People a lot of people resonated with the story.

Yeah, I think rob and that are posting IT to hacker news and I get like five hundred of votes and then a tonic was like very public know they're like top front page of hacer news. Thousands of developers and founders like reading kind of retrospective and i'm giving like you know their own feedback as to why level didn't work out at that. What if you like to read those comments and be so public with what happened?

I think IT was a mostly positive experience, honestly, like there were definitely some some dismissive commencement s and like go only put in a year and and then you know of course, most people recognized like, well, no, this is this is still a years worth the time you and definitely IT was interesting to see kind of the varying perspectives from from the more traditional silicon valley lens versus kind of the more the hacker lens. Two very different ways of viewing this whole, this a story.

And then I think, like ten days later, you had another post, that one to the top of hacker is called finding my next. Book strapped business idea you're kind of outlining your process. Yeah, had to go about looking for a business idea.

You a lot of good stuff in there now you talked about the fact that the model already needed to exist. You've got about a lot like the internal motivations to like, why am I even doing this? Know why do I want to start a company? What's going to make me happy? What are my ambitions? How do you actually think about that today?

He was really helpful to go through that exercise because I think it's it's it's important to know like first, know yourself, know what you want out of IT. I like, yeah, one of the things I put in there is like this needs to be kind of like some explicit timelines on on being able to reach certain milestones was really important to me.

So especially when you're not dealing with an infinite runway or you're not willing to like go out and raise the money to give yourself a really, really long running way, like getting to those milestones quickly. He was really important. So is like part of IT was just digesting like lessons learned on what not to do again and and some of IT was like just sort of A I felt a matching my reaching my own maturity, unlike on inset stuff, which is always a work in progress. But yeah I think found your market fit is is so important to try to strive towards first and foremost and then kind of let the rest fall from there.

You kind of tell that like you ve been through the ring or a bunch of times, like when you are founder and you have this list of, like I will not do this, this is my train these are my like every Crystal founder as a list of things like they're not going to do anymore. I just want to read through your list in the blood post because you've got a bunch of stuff here. You have said the product should not be mission critical.

You don't want to build anything. We're like you having downtime is going to like affect your customers businesses, which is like probably like a stressed thing because that super like any hackers goes down like i'm sad, but like no one's life is a room and like no one has to go. Any hackers and good, it's relaxing.

You said your MVP, your medium mumba products must be shipped within a few months. He said the market mastery exist. You said that making a sale shouldn't require more than a few decision makers.

You want to have to deal with whole giant pipeline of people. You have to convents to APP. You said that native apps should not be a minimum requirement. People come to expect the native desktop back. And like the android open IOS happen like you just didn't want to have to build all that to tell your product. And then finally, you said the market should overlap with your existing audience that you've already built up over years of building products and building in public and tweet speaking and all sort of stuff.

That last one is another another piece like this debate always goes on of like is IT are you required to build an audience in order to do successful software company? And i'm definitely what that would say. Like, no, you're absolutely not required what you should do. What is the smart thing to do is to always just look around you at like what are your unfair advantages that you potentially have and try to make the most of those. And for me, like this was a pretty, pretty considerable one like, yeah, i've been investing in the podcasting for a while and and kind of publishing online and we could do myself a service by by trying to find something that I could sell to those existing people who are already in in the circles.

How did you go from this point where you're kind of wondering ing to the wellness? I think you're literally in the cat in the woods try to think about what to do next to deciding that you going to do savi cow, which is what you working on today.

That was the most chAllenging time, to be honest, because I wanted to get down to work on something like I wanted to really sink my teeth and is something, but I really didn't know what I was going to do. And I sort of had the summer in front of me and spent a lot of time like in ahamed, c pinking.

And with my idea note and kind of scalery back through past ideas and and just dreaming and having the pressure to come up with an idea is really hard. But I was like, what? I have a couple of options. And it's like plan b, plan c.

They weren't all that bad. I could go. Could you get a job? And I think there is absolute zero shame in doing that.

That's where entrepreneur S A lot of times get some of their fresh ideas is from working in someone else's company and observing all the things that are broken you and and so I think that's a perfectly like reasonable path to go. And I I did entertain that. I also don't want to treat ideas as too precious in their own right.

I just wanted to kind of follow a framework of like let's explore problems and because there's tons of problems all around and kind of explore and and see what see what I uncover and and so I end up working for a little while on protocol. Static kit that was a um IT was a sweet of tools for for people using like static website technologies. So like being able to embed form an rich client side stuff on your static site.

I didn't really have a super clear vision for where to take that, but I was sort of like a and in between like I want I like this kind of technology space, and I want I want to play with some of some of the stuff and just kind of keep shipping stuff into the world. And so I did that for a while and I think I was still like a positive experience, even though wasn't like a wasn't like knock out success. But you kind of kept me busy and kept me thinking for a little while.

You think that being like so public with everything, because like you like relying all these experiences is on your podcast. Do you know that motivated like you to a bed flicky trying and not go get a job because it's like no one knew what you're upp to. You would probably would have been easier to be like I quit. I'm going to get a job.

I'll come back next year. I think I was definitely a factor. Yeah and I did think about like stepping back from the podcast for for a little bit of time during that period.

But as like you know, I don't want to get out of the game ultimately, I was still I still felt a strong pole to be in IT, in part because of because of the podcast and things like that. And I thought that is a good forcing function, I think. But but not always easy. Not easy on the ego either. I ve.

I ve like social accountability. I love having any sort of like, I don't know, pride or shame or status, reputation, like any other people you can bring in to what you're doing. Because if you think about IT, like we all have that like jobs, if you have a job, you probably have a boss, you probably have co workers, you have other people who can kind of see the output of what you're doing.

Maybe it's hard to explicit always know that, that is motivating you, but I probably plays a role. And then the second you become a founder, like unless you're broadcasting what you're doing to lots of people, you're gonna lose that motivating factor. And it's just you and it's sometimes it's like easier to let yourself down. And IT is to let down an audience like thousands of people listening to your every word on your podcast and investors.

So like I, I raised some tiny seed funding basically shortly after the after the levels the level wine down and that was sort of like a that was Robin aren't making bet on me as a founder, you know and saying, like we think you're going to do some interesting things. And so that was both a stress reliever but also like caused me to put a lot of pressure on myself. I think because now now I now dealing with other people's money. I have other people have skin in the game here. And so it's funny how a lot of times some of the things that should be a relief are also like a big dresser.

exactly. Yeah I feel the same way with action stripe. It's like, god, this should be a relief. I'm like done with the solo part of like no, actually the company bought my company and have you a lot of pressure to make IT like a worth wile purchase for them.

And I think that pressure is kind of good because a lot of ways, as an andy hacker, if you are aiming for freedom or you're aiming to live in a very good lifestyle, you can start your business. And almost like on day one, you feel like you've made IT you like, how do have a bus? Anya quit my job.

But you know, i'm working for myself and it's really easy than to just take all the pressure for yourself and be like i'm going to live a life of freedom and is but like you, I can't really do that until you've gotten to where you have gotta a savka, till you've gone to the point where you're profitable. It's right dangerous to start thinking that way until you've already been successful. And so ironically, choosing to be an any hacker probably should mean choosing to put a lot of pressure on ourselves and to be accountable to other people until you get to that point.

Yeah, I think that's kind of the maybe a hidden, a hidden secret or quality about india cking, right? Is like there a lot of people who kind of see the there's like the pockets of like digital no mads and people who are like i'm going to do the geo arbitrage game and keep my expenses low and get just enough income so I can I can have this this lifestyle of adventure, whatever, whatever you want to optimize for. But I think also that those of us who kind of get into this game of like running our own companies also get tugging by that ambition factor. And like before, you know, I like we actually do want to do really interesting things that and stay chAllenged and that chAllenged kind of just drawls you towards towards more and more ambitious things, which does kind of encourage a little bit on the on the care free, easy lifestyle part, that kind of entities.

the people almost opposite sort. What your goal is, you end up getting dragged into IT, and it's kind of like our own fault, like we do IT to ourselves. But maybe there's something more interesting about IT overall. Maybe the dream that we want the super care for easy life is not.

Necessarily what we want, I think, might be sort of like the the dream of like retiring on a beach after you sell your company, which like note, no one is that actually doing that are being happy doing that least the kind .

of person is gna create a for successful company is not the kind of person is wired to go for a very long time.

Yeah I think we're most fulfilled by chAllenging endeavors ultimately, I think so we listen to a podcast um from SHE was like the right hand executive at netflix and kind of talk in to how like like yet the best days when you come home from work, the best days are when you're like collapse on the captures like oh my god, shit was such a hard thing we just did and we accomplished IT. It's not the days where like, oh, nothing really happened and I went inside of my desk for a little while and left early like those aren't in the feeling days are the ones .

you remember where because is also like a lot set about sort of the toxic looking at least start up culture. Everybody's like overworked now and they are sleeping under their desks and the whole team staying up, bleat. But often when you talk to people in those situations like that is like those were the best times, like the people really remember those times, that they are bonded together.

It's almost like a tribal you just go through hardships with people who are your comrades and who are your colleagues and then you come out the and and like that's what you remember so let's like about the ah the beginning of savi cao because eventually decided to start saving cao and it's kind of hitch your pattern there already was one or two big in comments in the space. You are already doing this. Well, why did you think that the world needed another scheduling application?

Yeah so i'd become i've been a user of of colony for many years. We innovate with them a trip early pretty early on because we were using them for demos and we needed to like track that. Like when someone scheduled something, we all actually put them in a workplace.

So I was like very, very aware of, of the tooling and kind of the problem space. And of course, i've used IT to schedule customer interviews for all the products I ve done in the past. So sort of understood like the underlying problem here.

But the thing that really got me intrigued by IT was kind of observing like the weird power dynamic issue that are rises around using scheduling links. So there are some some pockets of the industry where people just literally refuse to use them because it's just too photo a like, it's too two laden with land mines like you might end up offending somebody. And so they just always fall back to the efficient wave of scheduling times.

And the other people like are just, I want to use that, but other people are superheated ant. And so there was a curious thing to me, that lake, there's this tool that or the whole class of tools that save people a ton of time and yet there's all this resistance to using them. And it's fully product problem and a people problem like there's here.

There are like elements of adequate and ways to like just communicate well so that you don't turn someone off. You're sending sending your communication, including a link. But like so I think it's it's too fold.

And I think that I wasn't seeing a lot of innovation happening on the product front around like trying to actually make this Better, make this a more collaborative experience, reduce friction as much as possible for the schedule. I kind of felt like things were just sort of status quote for a while. And yet, this is a highly demanded tool.

I mean, I didn't plan on IT on demand increasing even more during the pandemic because I started like right around the beginning of the pandemic, actually. So that's what kind of got me interested in the problem space. And I also kind of compared against my my rework that we can went through some of these criteria that i've been building up over time, like people can use IT in in single player mode, you know, an individual can just start sending out links for themselves and then gradually their team can can hop on.

It's important, but not like if I need ten minutes of downtime to do some database maintenance, it's not a big deal. And so IT kind of check a lot of the boxes. And so then this, a question became, like, well, do I even stand a chance against, you know, extremely successful and an overall well liked competitors? Like calmly.

right? And can you explain to people like how an apple calling works? I sum, most people have like use this, but pretty lot of people have no clue like what this a promise is even solving.

Tell me, you basically create your account, you attach, you link your calendar to IT. So you authorized your google calendar or outlook calendar, whatever you use, and then you create a link. And the link basically has IT gives you your availability minus any existing events you have on your calendar.

So that report can find a time, much the cast. And what's fine the time? I sense you like a savy cAllen. And you click and you just like, no exactly what times are free and my calendar that I was specified, I don't have to do anything and I just get my canon to the next day, the next week and like your event is on there. It's like having almost like like a personal secretary or something or assistant is help.

Yes, exactly. yeah. And that's why like you know, you're kind of more classic busy executive may they may have a personal assistance. So instead of using a link, they would just right like copy their assistant on an email thread and say i'm going to hand you so to nowadays .

is the assistants are just using colony and saw on the light the up ah .

you are staring .

this idea in the face. It's student really well on your checklist. I think probably the only item on your checklist that IT might not be like perfect on is the fact that like might be missing critical to a small degree. People might be upset if he goes down.

But like you said, it's not the biggest deal in the world, uh, but you've got to face down this huge and compete that people kind of like IT works well enough like I probably haven't had very much time using calling like regret, using calender. What's your playbook you're building? And after that takes on a huge and company, how do you know if it's a good idea to try to build something in a space where people are already solve that problem really well?

I'm hesitant to say that it's A A repeatable playbook because I think you know every every APP is a little different. Every industries is a little different. But what I recognized here that gave me that gave me confidence was that I sensed some stagnation at some of the bigger income is slowing down a bit.

And that's kind of a natural thing to happen as you grow in size, like colony has hundreds of thousands of customers and know millions of people using the product. And you just it's just hard to like turn that ship quickly, you and and be able to respond quickly to to what customers are demanding. And I started looking around and seeing a lot of while there is a lot of love for the product.

There's also a lot of dissatisfaction out there on forums. So you can kind of kind of did the thing of skewering places where people are talking about not just colony, but all the all the tools and and a lot of people, you know publicly asking for things, expressing dissatisfaction with things on and these threads just kind of sitting around for a couple of years with no real response. And that's that's a sign that like this company is both really successful, like they're doing really well financially, but there not responding so quickly anymore to what customers are wanting.

And I think that's that's where that's the crack where an india cki has has an opportunity until like and so I didn't know if if he was going to look like, you know, carving out this little, this little niche and was savi C, I gna become like scheduling for x, you know, something very, very narrow and specific. I wasn't sure how narrow I would have to go. I mean, this product lends itself to more of a horse zonal type of positioning just because IT is so broadly applicable.

And so that was sort of I sort of held loosely onto that initially. Um and just um you know like I think April dunford is positioning book, which is one of my favorite resources SHE kind of talks about like intentionally keeping your positioning pretty broad because you're trying to have like a big fishing net to capture a lot initially. So it's like kind of keep the net wide but beyond look out for very specific things and ultimately kind of double down on on something. So I kind of chose this angle of lake, the awkward dance um peace and really just kind of try to get my MVP done as quickly as possible honestly because beyond that, like talking to potential customers, I got a lot of people's expressing skepticism like I don't know, man, I think this one locked up already and .

so take a little bit of sending your scheduling link shouldn't word like a hundred percent and the awkward dance in the feeling of IT and like reading that like I feel I mean, I feel that pain like okay. That's definitely a problem that I ve had a scheduling links IT deficits a little bit awwad that's kind of a cool way to car about your own niche in an industry that's already got like I want to what does county some place said? What is there sort of claim to fame count that calm there says easy scheduling ling ahead, they're about easy you to see a simple, easier than like your own sort of your own benefit.

And I think I got to I got to draft off of a lot of the awareness that they've built up to. You know, like i'm primarily getting people who are coming from colony have been to satirize with IT looking for the paradigm amic stuff to be resolved. And I mean, they I think there really is a colony.

They was like they were having to teach people what this tool live in is and how IT works. And so that's that's another thing like you ideally want to be in the position where savi is today was like there's a bunch of people who are already very aware of with this problem space. And now there's like they're looking for something a little different um on a few things that and if you can execute on IT, that's for the opportunity.

I'm looking at like an action because their home page is all about educating people even still, it's like. You can schedule meetings without the back and fourth emails and know here's how that works is what you do. And your whole thing is one hundred percent predicated on people already knowing this, like, okay, scheduling your links and feel weird.

That only makes sense to people. They know what a scheduling and link is. And you say like finally, a scheduling tool that put the center and the recipe will love again. That only makes sense if people this is. So you're selling to like a kind of a more educated, more experienced market of I guest discrown tld scheduling tool.

Exactly how do you avoid some .

of the in mistakes you made in the past though? I mean, like for example, with level, one of the hard things was like you just had to spend a lot of time building features because you're taken on this income ent like slick that already had a ton of features that people expect and it's pride the same with savka. You start off day one. And I guess what like all especially sensors sort of catering to like these existing users already know there. We have like some minimum level of expectation for, like what does this do, everything that calendar, which IT might be a huge like month slog, slog for you just to copy all these features.

That was something I was deliberately trying to get out in front of this time around. And really, the way I mitigated IT was engaging with anyone who came, came in the door, put their email dress on.

I tried to Spark A A conversation with them to figure out like, okay, what exactly are you looking for? What's the minimum that you need in order to to use this product? And so I did push IT pretty aggressively when I first started inviting people in june, july.

I was just a couple months into the product and he was missing a tone of features. I mean, we're still playing catch up on on a lot of the long tail of features you know that the people people expect. But but I found like there's actually you know kind of the eighty percent well, there's a lot of people that are they are not using that other twenty person twenty percent of features IT.

Seems like the majority of people are just they just kind of need to be able to present their availability and all the rest of the stuff. It's like nice to have. So trying to get clarity as early as possible and like how essential is that? Like is that a nice to have or was this a deal break?

Er and that makes lot of sense because i'm the kind of person doesn't really need like calling has a million features that I just don't need and all those of anagrams and things I guess some people need like IT, I just see the basics and then are going to focus on like the scheduling screen.

Like I send somebody the link, they click the link, then they go like they see my calendar that's screen that you have a super friendly, super customizable. There's all the stuff that I can like put on there to make a like a good experience for them. So I kind of delivers on your value proposition of, okay, shouldn't feel weird.

I shouldn't feel awwad shouldn't like i'm insulting the person by something in this link. What about growth and like marketing? Because the other thing that's hard is like, okay, well, yeah, the incomes are sort of creating this market.

They are educating people but also like because there are one's educating people, everybody knows their name. And especially with the scheduling stuff, it's like a little bit viral where like when somebody sends out a scheduling link, everybody now the recipient sort of years about that is kind like greeting cards. And nobody buys greeting cards.

And this keeps them for themselves, like everybody who buys a greeting card gives IT to somebody else. So it's A A naturally via product. How do you like this brand new player who no one's ever heard of? Cut through basically the noise and they get people to start using you instead of count. How do you get people even find to you?

Yeah, that's I mean, that's a great question. I think that that quality of like every time someone uses my product, they're inherently exposing IT to other people. That was one of the big um kind of selling points to me in choosing to take on this endeavor because um that that kind of viral loop is is extremely powerful and in listening to like um kind of deconstructing how how my competitors have grown like that is of the number one by a large of growth growth path for them. So for me, that was kind of about working as hard as I could to recruit as many people from my sphere who are listen my podcast, follow me on twitter or whatever, to start using IT and and then just inherently spreading IT to to their second degree contacts. And that works .

out because that's like the holy grail of like every soft engineer once to put an APP that once you build IT IT just prides itself and this is growing on this. You want to do anything because it's just naturally viral.

I think it's um I do think it's working. It's extremely hard to track um in a way that's like that's not totally invasive of privacy. I feel like we've kind of taken a standard like trying to trying to use privacy where tooling as much as possible.

I'm a big father's alycia fan um but like yeah figuring out all the multiple touches that people have with the product and like was that touched where they received a scheduling link and scheduled something, how at what point to that touch occur in their awareness ness cycle? Very hard to very hard to suss out. I want to get more sophisticated about IT.

But like anecdotally, we started asking kind of a question. We added to our on boarding. How did you hear about us specially to get get some quality of data on that? And they definitely get cited quite a bit of like, oh, I used I used the link, everyone else. So I think IT is I think is working. What else are you doing?

You're doing any like content marketing and are you doing like social media marketing of mAiling less like what else you're even trying to do besides relying on the word of mouths grip?

Yeah so we've done um we've experiment with some podcast ads which are also the very difficile track um decide from using using a coupon code when you when you hear mention on the on the ad um but I think that is definitely driving awareness. We're working on some strategic seo stuff. So just kind of dig in do in our keyword research digin into that and and making some strategic landing pages.

Um we are kind of spinning up when the process of spinning up in a filter program right now. Um so it's sort of like it's a grab bag of things. I like to I love to reference the the attraction book by Justin marrion get line burg. And sort of they're thinking unlike, you know, trying to craft things as experiments as much as possible to suss out the viability of traction channels and that sort of where we're at on trying to figure out like what what's the real break out, like insert one dollar, get three dollars back on the other side, fly. We're gonna be.

It's explore and exploit. You got to explore a bunch of different options. You got to put an enough effort such that like you can actually test IT out and come to like some sort of like believable inclusion as to whether not IT will work, but like not so much effort that you don't have time to try other tails and try other things.

And then when you find something that work to do exactly what you're saying, press the gas pedal and go like a hundred percent on that. But it's pretty like inspirational and hearting to see the like. You haven't necessarily found some like magic bullet and you've still been able to get to like this level of success, like even the other things you haven't done that you haven't perfected your user tracking and figure out what people are coming from and yet you're still able to make a profitable company. You don't necessarily have to do the entire kitchen sink to get to the point you have a successful business.

Yeah so much of business successful, I feel like, is like a despite all of the things that we have. Yeah and you like so many businesses. And this is what i've learned in working in the drip post acquisition, seeing what these page look like on the inside.

I mean, most companies are pretty chaotic on the inside. And there's there's just there's a lot of moving parts and a lot that, that doesn't end up working out. And yet, thankfully, this is just tend to march forward.

Well, it's pretty cool. See like how far you have come despite all this stuff. And I think obvious you have a pretty bright future and in any direction you go in seems like it's going to be promising.

Where do you think things will go from here? What are you excited about with savka? Now you ve gone at this point of profitability.

Yeah, this does feel like of a kind of an inflection point for the business like we ve we've made a past that that like ten k mark where it's like, okay, if you can make a past that and growth is not platov like you, I think you're on to something. So I feel like it's that that box is checked, which is allows me admittedly to breathe sigh of relief a little bit, you know.

And now the question becomes like how do I think about expanding the team? So that's of what i'm thinking about right now, like i'm wearing too many heads right now. So it's it's i'm i'm getting some help on support starting getting up all early next week, I think, and and then looking to make my first engineering higher to really help contribute the product.

Um which is it's daunting because I know what a big deal IT is to kind to make that first at first tire. You know what i'm thinking about like how do I want to what do I want my data data to look like? And honestly, my fondest memories from building drip were the earliest days where there was a couple of us that would come into an office a couple of days a week.

We were still flexible. We would work remotely a ton, but like being able to collaborate in front of a White board and then go grab happy hour later in the day was just was really nice. And I think I think there will be a little bit of a resurgence of of some partial like in person work with some of that like high fidelity human communication stuff that's really hard to replicate virtually. And so yeah, I don't have that part figured out. Yeah but it's something i'm thinking through like yeah.

that's kind of the fun set to think about because if you start a company, you can structure ever you want. And you can make IT. I mean, if you really like don't want any human contact, you can be like I want to remote company were not going to do video chat, you am not allow do your own thing and you hire people who thrive.

Like if that's the life, you you can do that, you know, if you want to hire people who are local, who are exhibits, you want to be in person and you can do that and have like a really great soul, like you can do literally anything that you want with your company. So like, you know, kind of that post where you are writing down, like what do I want with my life? I think I got a question should probably always be asking in myself as a founder like i'm still asking myself out any access every month should to figure where I want to go.

Even there were a lot as a founder. You had lots of and downs. Let's one take away. You think a flegne new, and I have to take away from your journeys of ardet.

So I think the probably the biggest peace advice I would give is to if you're like me and you're an introvert and you're natural tendency, is to like to dive into the code and kind of focus on product is to get outside of your comparison a little bit and really try to actively engage in the community, whether that's online on a place like gandi hackers or in your local town. Um I think if I reflect back on my own journey, like the biggest the bigger driver towards my success has been kind of the the different small groups that i've been a part of mastermind groups and and seeking mentorship that really helps you to to like santa, check your own assumptions and and keep you on the right path. When you have other people who are kind of intimately aware of the stuff that you're working on and kind of sAnitary checking your your ideas.

I love IT. I've had the same exact experience and to vert as well spent gears like to apartment building stuff. Ff, without talking anybody and didn't work very well.

And then the second I started something, i'm talking people for a living and work really well. So intercepts out there makes you're actually connected with people and sharing what rup, the crime me, thanks for coming on the show. It's been a pleasure having you have you again saying we've had been in Robin in whole bunch of times?

I got to catch up.

Yeah where can listening ers go to learn more about what's drift to you as savi cow and everything else? Nois.

yeah. So the the product is at savi c dot com. I should have mentioned this earlier, but I have a special coupon code for hacker's. Audience, just use the hackers in the checkout flow to get your first month free and and then you can fine me on twitter at Derek mr.

So the actors keep on code and the shown note as well.

Thanks some thanks.