The SavvyCal Story with Founder Derrick Reimer

What is it like to start a SaaS company when you're a small fish in a big pond?

Watch Cory Miller talking with Derrick Reimer, the founder of SavvyCal. Derrick has a number of SaaS projects under his belt from projects that predate Calendly. He also co-hosts The Art of Product podcast.

Derrick talked with Cory about how he got started in SaaS — and what it has been like to take on the Goliath of scheduling apps, Calendly!

Get your first month free (plus a 7-day trial) at Calendly when you use the coupon code POSTSTATUS.

Machine Transcript

Cory Miller: [00:00:00] Hey, everybody. Welcome back to another Post Status Live webinar. This is my second of the day, by the way, Derrick, but I didn't realize I had set two on the same day, but I've been looking forward to this conversation for a while because we've got Derrick of founder of SavvyCal, a tool I've been using for months now and loving, and I pinged him on Twitter and I was like, I'd love to know your story.

And then as I, you and I've been talking for the last couple of minutes for the show started realizing how much. There's way more to talk about, but anyway welcome, welcome Derrick to the Post Status show. And thanks for being here today.

Derrick Reimer: [00:00:42] Yeah. Thanks for having me. I always enjoy talking to folks about the backstory.

Cory Miller: [00:00:46] Let's dive right in. The pre-story that I've learned about SavvyCal, which I want to spend most for time. There was, you started a company with a friend of mine, acquaintance of mine, Rob walling. I told you I'm really good friends with Dr. Sherry Walling has his wife and partner in life called Trip.

And actually I've got a Drip shirt, a sweatshirt by the way, or a hoodie at the house. I should've wore that today, but would you tell me the backstory right before SavvyCal? Anything you think there? Like how you and Rob got together for trip and anything you think that's pertinent to coming up to the SavvyCal story?

Derrick Reimer: [00:01:22] Yeah that's always a fun story. Because I actually met Rob in Fresno. So I'm from the central valley of California, just near the Fresno area, which is the main, like the hub of the central valley, and. Not exactly known to be like a hotbed of technology startups there.

But I was just born and raised. There went to college at Fresno state and then shortly outside of college, I didn't really know exactly what I wanted to do, but I was a hobbyist software developer. My dad taught me how to code. He was a software engineer or a mechanical engineer and had learned to code at work.

So it was We always had a computer in the house and it was just a fun hobby of mine. And I didn't really know I wanted to do it professionally, but I was getting more interested in kind of the business side of software and following 37 signals at the time and watching them like bootstrap software companies.

And I started to get more and more interested in that. And so shortly after graduating college, I, there was this competition locally called 59 days of code. She's really cool concepts. Like you basically build the prototype of a product and a business in the span of 59 days and you present it at a showcase and it was both like a technology competition and a business plan competition, like you, they wanted to see the economics of how you're actually going to make it viable.

And I remember it was like, There was a kickoff for this competition. I had decided to do it. I was like this seems like a good, like first foray into, doing a little startup and seeing how that all this works. And I remember meeting Rob at one of those first kickoff events and we we're standing on circle, went around the room, like, all right, everyone kind of present your idea.

And there was a lot of ideas in the room. Like I'm going to build a social network for whatever, following, like mimicking Silicon valley. And then here I was standing there, I like was building this product for developers to write documentation. So it was like, think of a get book or read me.io, precursor thing.

And it was like, super, super boring compared to what everyone else was pitching. And Rob kind of came up to me afterward and he was like, huh, tell me more about. About what you're working on. And we just talked briefly for a few minutes and I was aware of Rob was already like a, kind of a figure in the industry.

He had written his book and I had just read his book actually. And so it's like meeting a celebrity. That book was incredible. I didn't put that together when I met it took me a while to put that together, but I love that book and the name escapes me. I'll find it in a second, but start small, stay small start small steps.

Yeah. And so we met and then that was like my very first meeting from him. And then I went through the competition. Rob was a judge in the competition. He got to see my, some of my chops. And we basically just started a friendship and masterminding together. So we, it was me Rob, and another friend of mine. Phil Derksen actually from the WordPress space

Cory Miller: [00:04:06] They're awesome people to

Derrick Reimer: [00:04:08] o .

Yeah. So we all formed this little threesome or met up every couple of weeks and would just talk about business. And so I did that for a little while. I tried to grow a couple of things, had some failed, starts made all the classic mistakes that, that entrepreneurs tend to make, who are builders, like building stuff, but not totally validating that people wanted it and all that jazz.

And so I reached kind of the point in, I was still like living at home. I had very low expenses, but I was feeling the urge to like actually start making money and getting into a career of some kind. So I was thinking like, maybe I'll do some consulting or start building websites for people or just, Like doing something like that.

And Rob was like, why don't you, why don't we work together on some stuff? And so I started filling in as like a product manager for hit tail. One of the products that Rob had purchased and was rehabbing and it was going really well. And I worked on that for a couple of months with him.

And then right around that time, Rob was thinking about the idea for Drip the, marketing tool. And he was basically like, Hey, Are you interested in being the first engineer to build the first version of this? And so that's what we did. It was actually a pretty short timeline when I think back it feels like we had worked together for a long time before that, but it was really only a couple of months.

And then we got started on Drip and gradually I ramped up time on that. And then and then became full-time and the rest is history, as they say.

Cory Miller: [00:05:29] Yeah. So you moved out to Minneapolis when Leadpages acquired trip and then okay. Rob is a genius. I love talking to him the way his mind works.

I'm like golly to get inside. His mind is so interesting. And so what a fun story too. Okay. So now, so there's Drip was acquired. And then how did a SavvyCal come about.

Derrick Reimer: [00:05:52] Yeah. So yeah, after leaving, after moving on from Drip post acquisition I was searching for my next business to build and went through a couple iterations of different things during the two years that followed.

And after that I worked on a competitor to slack that was supposed to help you maintain deep work, a little better, not get so distracted and keep things better organized. That proved to be very difficult to bring to market because people are embedded in this lack ecosystem that it was a pretty tough sell to convince an entire organization to move over.

So that was kinda my first. My first big project post-trip. And so then I started thinking more about okay. I learned a lot of qualities about a software company that make it challenging for someone who's still trying to bootstrap self-funded, so I started to hone in on some criteria that I really wanted to find in my next business.

And, one being like something that that people can easily use in single player mode, not requiring the entire organization to switch over something that is not so mission critical that if I need to have, 10 minutes of downtime for maintenance on a weekend, it's not going to throw a whole business into chaos.

And there was just a number of criteria like this that started to build up and went through the typical exercises that a lot of entrepreneurs go through. I think searching kind of problem spaces that, that I knew. And the scheduling piece was an interesting one.

I had been a Calendly user for years and we had built an integration with them. I think pretty early on in our journey with Drip, because partially because we needed it, we were doing demos of the product and we needed, we thought, it'd be nice to be able to feed into Drip when somebody books a demo and then we can start them on a certain automation sequence.

And I know it was a pretty slick integration. So I was aware of that. Of that problem space, that tool I'd have been a user. But I always had some issues that I encountered when trying to use a scheduling tool, particularly as a maker who wears many hats, but also spends a lot of time in deep work.

And I'm very afraid of potentially wrecking my schedule and like filling it up with calls and having a week where I don't actually get anything done. Yeah. And so that was like a big, that was a big driver for me on huh. This tool like makes it very easy to schedule times with people, but it doesn't necessarily help on protecting deep work time.

And so that was one of the first problems identified, but also like probably an even bigger one that I think is more broadly experienced is the awkward, dynamics of sending someone a Calendly link. There's there are a whole kind of. Segments of the market that just didn't never do it because it's just considered so faux pas.

Like it's such a, it's such an insult to send one that like no one ever does it. Which is fascinating. I think a lot of times, like in the VC world, I've heard, I don't have a ton of experience with that world, but I've talked to enough people who communicate with venture capitalists and no one's ever using these links because.

It's seen as two full POS. So instead it's how about Tuesday? Tuesday's no good. How about Thursday? Dah. So that was a really interesting thing for me as a product person. Like it's interesting to look at a problem like that where most people are convinced that it's just a human problem.

And yet I usually I'm usually skeptical that it's. Oh, a hundred percent a human problem. Like I think a lot of problems are they're more nuanced than that. And they're can be helped a lot by product dynamics and some of the, some of them are very subtle, but I think so I started to form some hypotheses around like ways that I could tackle that.

And that's been, I think a big driver of the traction that I've had so far is a focus on that in particular.

Cory Miller: [00:09:22] Yeah you mentioned deep work a couple of times, which is really interesting. It seems like a passion of yours. And then this naturally it seems to play into that the pho the Fofo thing.

So interesting. So I have been using Calendly pretty. I had been using Calendly pretty prolifically for about at least a year, because it was this back and forth. That just drives me crazy, and what about this? What about this? And but it does sound awkward. I remember the first time I had a really good friend of mine has super uber successful entrepreneur here in Oklahoma.

First time we ever had like lunch was he introduced me to his via email, to his assistant and she helped wrangle the schedules together and everything. And at first I was like, why he pushed me off to this assistant, but then I was like, this is brilliant. It saves him time for sure. But what I heard him say later was when I do that she's my gatekeeper. To let him in to find a ton to my counter, to that guard regularly. I've found the same thing with offering my link to other people. I'm like, I'll add, here's what I'll do. And I'm curious if you have a little hack by this, but I'll say, do you have SavvyCal? Do you have a calendar somewhere?

No. If it makes it easier, here's mine. And I always say if it makes it easier, here's mine. Do you have any thoughts about that? Cause it's a thing I'm like everybody would just default go empower, enable SavvyCal there's a little easy button in every seven SavvyCal, and then we just. Make it easier.

Derrick Reimer: [00:10:56] Yeah, no, I think that is, that's a huge part of it is just the is the etiquette piece. And I liked that. I use something very similar and I recommend something very similar. That's Hey Feel free to send me your link. If you have one or we can use this one is a good way to frame it.

Another thing that I've been trying to build towards is being able to think of a savvy, Cal scheduling link as Hey, I've created this place for us to figure out. To collaborate on when is when a good time is. And part of the way that the product supports that is by giving you like a full calendar interface, which is one of the kind of key differentiators that we have.

Like when you look at a SavvyCal link, it's just, it looks very similar to the week view of your Google calendar or whatever you're using. And when you overlay, you can just see in high fidelity, like your entire schedule and all of the blank spaces on their schedule. So you can intersect them and see.

Visually without clicking back and forth. So part of this is Hey I've created this space for us to collaborate on. And then if they can actually accomplish that by oh, I see this it's a calendar. Oh great. I can overlay mine then. It's it feels less like, Hey I've created this like generic thing.

And you go through my jump through my hoops to put something on my calendar, so it's subtle, but I think it's powerful, nonetheless.

Cory Miller: [00:12:09] Thanks for that, because I hadn't intended to ask about that, but I wanted to be sure and do that because I think it's something that I've tried to work around.

Some people are like, oh no, give me your calendar. Actually, I don't know, 15 minutes before this, I was giving my SavvyCal link there. Yep. Okay. So you're going okay. I've used some tools like this and need some tools like this resonance, what I'm doing then how did you go about think the validation part for the customer?

Derrick Reimer: [00:12:37] Yeah. So I started with just a couple of conversations with people in people who I knew would be in my target market. That's part of the, also the leg up that I gave myself with this. I'm not one who would say you have to have an audience to build a software product or any business. I don't think that's necessarily a requirement, but it is.

But if you have some people who are in. In your circle that would also want to buy the tool. That's, it's just a, it's an unfair advantage you can give yourself. And so that was one of the ones that I felt like it was be a waste. I have a podcast, I have been working publicly through the Drip years and stuff on and putting effort into.

Into that. So I wanted to try to leverage that with this business, if I could, because I just knew that would be a little bit of an advantage. So it started like just with conversations with other founders. I knew that, if I can first sell this to other people who fit a very similar, like work.

Work habits and profile as me, then that would be a good place to start. And if I can't, if it doesn't resonate with any of those people, then that's probably a good sign that I'm not going to, I'm not going to make much progress selling to the wider market. And actually the first few conversations were met with a lot of skepticism.

And I think that's not totally unexpected because Calendly has a very good reputation in the industry, It's a pretty beloved tool, at least on the surface. Like when we were building drafts, there were some real gnarly tools that we were competing against, especially when you got into the more power user tier, like outside of the more consumer grade.

Basic email marketing tools and into the more power user ones. Man, there was some crafty old software that we could really, we could bang out.

Cory Miller: [00:14:14] Oh yeah. One's coming to mind right now. Yeah. Yeah.

Derrick Reimer: [00:14:17] I don't want to flame on the air, it's like there's there, there were just like, Yeah, probably like stuck in a prior decade, basically what it is, what the software felt like.

So it was pretty easy for us to run circles around them and say our UX is so much better, and with Calendly, it's not quite the same. There are a lot of people love the tool. They don't necessarily recognize immediately that they need something else. But what I did, I was able to discern from conversations.

Was that okay? People were willing to admit that like the power dynamic issue is a big one. They were admittedly skeptical that that a new product could make that. Dramatically better. So I got a lot of questions from people who were like I don't, yeah, I think I would be interested in something a little bit better, but I'm skeptical that you can make it 10 times better.

If you can't make a 10x improvement, then you're probably not gonna succeed. So it was, I definitely had to go with my own gut a little bit on this and despite some of the signals I was getting but other people were definitely like. Oh, yeah, I totally get it. And it's not what I, one of the other things that I picked up on was that the switching costs was not going to be too high for a lot of people.

It's just a matter of transitioning over you can, I can leave my other account running for a little while I can just start sending these links out. And before long, I can just decommission my old Calendly account. So that was encouraging enough for me where okay, I think if I can.

If I can get people to, to at least try it for a little while. I think I can get them to fall in love with the product. If I really focus on that and invest in it. And I think this, the prospect of switching, it's not it's not like getting your entire email marketing stack switched over where you have to rewrite a bunch of emails and do like hours and hours of legwork.

It's not quite the same. Yes. So that's, so that was the initial validation. It was a lot of, I always point out this book called the mom test from Rob. That's my kind of go-to resource. I came, became aware of that when I was building level the slack competitor. Because I realized that kind of the premise of that book is that he gives you a framework for asking questions of people.

In a way that you could even validate a product idea with your own mom, because the person who most likely wants to lie to you to save your own feelings, and you could even validate a product idea with someone like that and get unbiased information. So it's just of a way of questioning and it's, it was, it's been super helpful in the last couple of years in making sure that, because that's the thing like we have.

Our community is very supportive. There's a lot of people rooting for each other and that's a really positive thing, but it's also a big, a dangerous thing because you can end up getting the sense that someone wants to pay for something when really they were just trying to make you feel good.

Cory Miller: [00:16:51] And I have come so often. To idea, then go find the group that is coming, or I wish this happened. I wish this kind of thing. And then it's like the hammer and the knife. If it's got a hammer, everything looks like a nail instead of this lice, last thing is coming from problem first, which sounds pretty obvious as entrepreneur for, but I've had to like really retrain, no shiny object idea. That's one thing. Everybody's got a cool idea. Everybody's got 10 cool ideas or should just say ideas, but the other side is like finding somebody's pain point and problem. What's curious to me is that the killer feature for SavvyCal that I switched on there's this awesome offer to buy out my calendar.

And I was like, oh, yes. Yeah. But the second was curious where this came about is the week view. It's a visual view. And I love Kenley because it saves me time or I did love Kelly season a time, but what they didn't have is like I had to click through, I had to keep clicking, and see the buckets and maybe that appeals to some other people.

And maybe I'm more visual, but I love that. I'm looking at it behind the screen right here. And I'm like, I love just showing people when I first got the free account, I was like, oh, I'm just going to go. I'm just going to get my little. Like window and screenshot and go here it is. Here's, what's free, and then I got to get offered and I was like, oh, I got to take this. So that's that definitely can those two things converted me. But where did the week view come into or the visual thing? Was that baked in from the back?

Derrick Reimer: [00:18:24] Yeah, that was one of the initial ideas on. How to like how to set myself apart from what was out there, because it was motivated by a couple of things.

One the, my own desire to be able to quickly get a sense for what, when I'm sending a link out to somebody. I have anxiety as the sender, as someone who's not like my job is not to be in meetings all day long. Some people that's like they optimize for keeping their calendar as open as possible for anyone to book time.

But for me, where I have a balance of that kind of the deeper tests and stuff like. Anytime I send it out. I always wanted to go double-check so I'm always, my, my flow with Calendly was like, okay, open the thing, open my calendar, put them side by side, look back and forth, spot, check in the next week or two and go and make modifications as needed.

So I knew that there was a lot of this like kind of manual work that I was doing every time I was sending a link out. And so part of this was just envisioning like a way to. To bake that in and make that as smooth as possible. And part of it was just like being able to look at your preview, your link and see your availability right there on a calendar.

And so I thought of it first from like the administrative side of it as the one courts, configuring your link. And then it was like if this is good for that view, this should be good for the scheduler as well. And if they can put their calendar on it, then that's even more magical.

And so that's how it that's how that one stuck. I It was a. That was a big decision to make upfront because it took quite a bit of engineering effort to get to, to make that actually happen. And it's still a work in progress. There's still, I keep doing these rounds of UX improvements on that view to cause there's a lot of little considerations too, to think about, to make that kind of visual interface work really smoothly. But I think it's just. I think it is quite a leap forward from the list of time slots that everyone else has,

Cory Miller: [00:20:17] Oh, yeah, for sure. And I think you just announced maybe a couple of weeks ago, Microsoft, over, you had Google back then, which fits where you started from, the story of where he started from.

And now you've got that other side, which is, cause I've got a partner that is Microsoft Outlook fiend and I'm like, I'm Google, sorry. But, and we always battle, our calendars battle.

Derrick Reimer: [00:20:40] Yeah. Yeah. So we have that integration and there's also pretty strong demand for iCloud. Like apple calendar integration and just the long tail of smaller ones, like fast mail and stuff like that.

Yeah we're trying to get that done as soon as possible. Obviously those a big engineering lift to build another calendar integrate.

Cory Miller: [00:20:58] Oh gosh. Yeah. I've just heard how a complex calendars can be in general. So I can't, I definitely can't. I can't can imagine as a non-developer. Okay, scroll back like about a year ago is when you launched savvy. And I thought for some reason, maybe you're out longer. My good friend, Matt Mediero said, I should give credit for sharing, putting SavvyCal on my radar, but so about a year ago or so you launched, is that correct?

Derrick Reimer: [00:21:26] Yeah. So I actually started working on the product back in March of 2020 and do working pretty publicly. So I think I start onboarding the first customers in July, June or July. So just about just under a year ago. And then spent a little bit of time in that phase, basically inviting more people in when I felt like my learning was slowing down, that's my. The strategy that we did something similar with Drip too in launching it the slow launch where you keep inviting people.

And when, once the learning SLOs invite more and then officially went like fully, publicly launched in September when the doors were fully open.

Cory Miller: [00:22:01] Oh my goodness. Okay. I just kinda thought I should have looked in. I just thought you and SavvyCal had been around for long wait longer than that, but that is so fantastic.

Derrick Reimer: [00:22:09] That's quite a compliment. I appreciate that.

Cory Miller: [00:22:11] Oh yeah.

Derrick Reimer: [00:22:12] We wanted to get past getting past that initial hurdle. It's so tough when you are really new and. People sometimes don't take you to that seriously, or they think they're just skeptical because you're new, that's a tough hurdle to get past.

So that's encouraging to hear that That your perception was that we'd been around a while.

Cory Miller: [00:22:29] You've been doing this for a while, you know how to build stuff, which is awesome and that reflects it in the product for sure. Okay. So you if I scroll back, you tested or you put out the mom test and we're talking to some people and got a little bit of a negative about the space.

Yeah. Can you walk through like the launch? What you think went well, what didn't well, what takeaways you'd have and you have your Drip experience too, to compare to for sure. But starting rolling it out slowly. You had already built up an audience though from your podcast to the building product, but can you give some takeaways for someone building two and trying to like have a launch and do that, where you get enough feedback where it's not just crickets, any thoughts there?

Derrick Reimer: [00:23:11] Yeah. Obviously he did the started talking about it. In the places where my potential customers were already listening to me, it's talking about on the podcast and I throw up a landing page and kind of built, did sit a manifesto type thing.

Like here's the stake in the ground. Here's the problem. And then yeah, collecting email addresses. So I had a kind of. And just an email list of, I think it was around a thousand people or so when I started inviting people in and that's, that was just from making noise about what I was doing as much as I could, without being annoying.

It was the balance to strike. And then, yeah it's That is always the tricky thing is figuring out what, how do you define your minimum viable product? I think we've see trends vacillate on this a little bit where most of us need to be encouraged to ship earlier than we're comfortable with.

And I definitely put myself in the, in more of the perfectionist camp where I feel very Very uneasy about putting something out into the world. If I don't feel like it's perfect, but the truth and software is and everything else in life nothing's ever perfect. So great

Cory Miller: [00:24:10] spoken like a great perfectionist to enough perfectionist

Derrick Reimer: [00:24:13] yeah. Something I have to remind myself like daily. So it's but I do think that there is some like I'm talking to my friend Peter SU who's building a Typeform competitor right now, and he's a little bit earlier and he's in this stage right now and something that we talk about a lot, because I can reflect back to when I was going through this, a year ago was like I.

I have my own list of things that I feel like are essential and then things that are nice to haves and constantly sanity checking those in having conversations with people. Like when I get the chance to talk to a potential customer, trying to make sure sanity check that like the, those assumptions are correct.

And really not like having the restraint to, to put in the time to build that initial set so that I'm not putting something out in the world that. Is 80% there, but because that 20% is not there for a majority of people that I'm sending it to they're just going to not. They're not going to end up adopting it so it's trying to figure out what that feature set is.

It's that whole analogy of you've got to build like a, you don't want to build, you want to build a bicycle, not half of a motorcycle for your first version.

Cory Miller: [00:25:23] I was thinking of that, the skateboard, then the skateboard becomes like this little thing and then it becomes, yeah, absolutely. Which sounds, the image that we're thinking about for the MVP is. I've seen it a bunch of times. I go back to and reference, but in practice it's tough. What is this? You know what I mean? Yeah. But what I liked from your story is you go, I'm building something that I would like, and the people, a small set of people that I know. And talk to on a regular basis, which I think has to be take out take entrepreneurial types.

Yes. It could be quick adopting.

Derrick Reimer: [00:25:58] Yeah. Yep. Yeah. And I think sometimes that's It's really good. It's really valuable to get those first few people that are, even if they're friends of yours. So it's not a perfect indicator about what the broader market's going to do, but still that's, there's value in that.

And just getting those first couple of customers that are like, no, I will truly adopt this and I will start paying you. And it's not just because I'm your friend and I want you to succeed. But no, this actually solves my use case. Me Rob was one of the first customers that I got on and. Because he was like, yeah.

It's, as long as you have these. These three things and it was just like core capabilities, yeah, I'll switch. Why not? And that's a big, that's a big deal, especially with the product where there's this component built into it. That also made it really attractive for me was the.

The kind of the viral loop or the, the fact that every time someone uses the product, they're exposing it to more people, and so there's value in getting customers as early as possible, just using it so that you're getting that additional exposure.

Cory Miller: [00:26:55] You really do have that. Yeah. That's so bringing you have it built in for sure.

Derrick Reimer: [00:27:00] Yeah. And Drip had something very similar to, we had our little powered by Drip thing on the email capture form. So that was also something that we had played with in the past and recognize the power in that.

Cory Miller: [00:27:13] That's he launch, so you're not even a year yet, but I know you're I'm not going to be asking revenue stuff, but I think you're doing really well for not even being a year into it you taken on a Goliath, which was the con you know, really compelling thing to me. I think I saw some time maybe it was on LinkedIn accountably had like over a hundred people and, you can do start-up math and stuff and go a hundred people. It's probably 10, 15 million. I don't know.

Derrick Reimer: [00:27:40] Okay. They actually went public with some numbers there. They did. Yeah. They did like a round of like ink magazine interviews or something in the last year. And they raised some secondary. Secondary funding, I think. But yeah, I think there are, like, I think they reached a hundred million in revenue last year, like they doubled during COVID. And it was like a three, $3 billion valuation, I think. Wow. Yeah. Intimidatingly large numbers. Yeah.

Cory Miller: [00:28:03] Like great for you to, cause I can't even think of, I think there's like book like a boss out there and stuff like that, but I, and I love the fact that. I'm going to go back to viral loop. You know what you're saying? When I share my SavvyCal, I'm promoting SavvyCa, in there. Okay. So we talked about launch, we've talked about backstory and all that one thing I think you've been really so good to share is mistakes or failures. , wasn't the first thing you did out when you left a Drip, you had other things going on that you were trying, I think. And I'm curious, your perspective on this too, is most people look at successful entrepreneurs like you, this is your second, third, thing, and go, Derrick's got the golden Midas touch. When I left my company, iThemes everybody.

Everybody's what are you doing next? And I was like, No idea. No, I sold my company. I got my team transitioned and I went back out. Cause I knew I wanted to be back at, on this entrepreneurial journey, but I didn't have some burning, like big, amazing idea. I was, and I think people were disappointed in that.

Yeah. Probably expecting something cool that they can like high five. And I was like, Nope, I have some broad directions I want to go in, but I have no idea. And it took me a while. It sounds like you've got some elements of that. Like SavvyCal didn't happen just right after Drip. It was, yeah. You had some things that started in and failed so I'm curious.

Derrick Reimer: [00:29:26] That was actually, and it was very It was a very difficult route to go. I think I probably would try to do it differently, although it's easy to, it's easy to talk about retrospect in that way, but yeah, like I, I left Drip and obviously it was a good outcome, financially the exit, all of that, but it was not like It's not was not never work again, like outcome.

So I knew I was going to be, I was going to build another business like that was in my I had some breathing room obviously from that. So I could afford to take a little bit of time and kind of figure it out. But I think that's still even knowing that there's not an immediate.

There's not immediate urgency to launch a business and have it be successful right away. Still doesn't make the mental aspect much easier, at least in my experience it did.

Cory Miller: [00:30:13] I'm going to rally right there with you. No

Derrick Reimer: [00:30:16] yeah. Because it's cause you wake up in the morning and yeah. And it's now what? I want it. And so for me, what I did was I didn't even really take a week off after leaving Drip, I knew I had schemed on this idea for a while. And I had, it was admittedly quite ambitious to think that I could compete against slack, with when that, when so much of the way companies were organizing their work was moving in that direction.

But I was willing to take a swing at that. Anyways. I determined I was willing to do that, but but man, it was not. It was not easy going then going into this zone of like, all right, I'm going to be basically funding my own self for a while and building towards this thing. And then, and only for it to ultimately not work out It was very mentally challenging.

And there were moments where I was like, okay what do I do I just need to take a break from this entrepreneurial thing and go just go work somewhere, which I think there's absolutely no shame in entrepreneurs doing that. There's nothing like a nice, consistent salary to give you peace of mind and let you breathe a little bit and potentially restock your creative juices for something new, oh yeah. I knew that would probably happen if I went to go work somewhere, I would probably within the first couple of months really hone in on some problems of okay, this tool we're using at work, this thing is terrible. And I have ideas about how to make it better. And then maybe, set me down a path of fixing that. So

Cory Miller: [00:31:35] exactly. I had an honest for a friend here. After I left and I was doing consulting in my previous company with software. And a lot of the entrepreneurs are like, ah, don't trade your time for money to get back into the product space.

I don't have this compelling product idea that I wanted. Yeah. And I don't want to chase not that I don't want to chase something. I want to chase a product. Of course. And then I had an entrepreneur friend tell me but in between his things and he's had several. Ramp up, sells exits on that.

And he said, but when you do consulting, you're getting back out into the market and you're learning stuff. And he goes, yeah, a couple of his consulting gigs. He had a, he got paid extremely well and he found problems to solve and they turned into new stuff in addition to networking. And so I'm with you on that. You gotta do what you gotta do. Keep chasing the dream.

Derrick Reimer: [00:32:23] Yup. And so I was close. I was really close to that point, but then, and then the opportunity arose to join tiny seed, which is Rob's accelerator this new form of capital for companies bootstrappers or what just companies that are not on the path of taking traditional venture capital.

And so that sort of gave me. Okay. Here's, here are some people who are willing to place a bet on me, and that was Robin INR is the whole thing. It's look, we know you're going to do something interesting. Yeah. And that's, those are good words to hear, but also. Causes someone like me to put a lot of pressure on myself.

So I went through this phase of both being feeing some relief okay. A little bit of the runway has been reset. I have some outside support and I can take another swing at this thing, but also okay. Yeah. Everyone believes in me, but do I really believe in myself? I don't know at this point, it was at a low point at that moment. So that was another challenging point, but. I kept going and built, I built a product that didn't get a ton of traction, but it was it was an okay, like I needed to do something. And that's I feel like shipping still, like continuing to ship code, dig into new technologies.

I use it as an opportunity to like, to get really up to speed on kind of newer ways of doing front end development, newer tech stacks that people are. Are using these days. And so I tried to make sure I was doing things during that time that would be that would stick with me and would get valuable.

Cory Miller: [00:33:46] Yes saying the front end stuff probably helped tremendously on the product that we're talking about now. It's also a difficulty, I think is, the classic one I always hear about is, Steve Jobs, learning calligraphy and college, and then that emphasis in the back. And when I remember my first Mac, going, oh my gosh, this is the coolest thing on earth. And that, serendipitous thing helped out in the same. I'm sure it's true with you. Yeah. Yep. Okay what let's see here, we've talked about failures. We talked about launch. We talked about how the product came about and all that it problems, face, stake work.

What have I left out that you want to talk about or share? If I missed something along the SavvyCallaway or the Derrick story?

Derrick Reimer: [00:34:30] I don't know. I guess one thing that's been on my mind lately, we can just touch on is it's starting to think about growing my team. And I think this is one of the, one of those.

I've been in the zone right now, a lot of making. Getting having to get control with making a lot of decisions, important decisions with incomplete information, which is one of the biggest, that is one of the most challenging aspects of being an entrepreneur, I think is that you have to have a certain degree of confidence and boldness moving forward in certain directions, even though you always.

I'm always in a state of feeling like I don't quite know what I'm doing. Or and part of that is true just by nature of not having all the information and that's how most of us have to operate. So that's, yeah, it's been interesting, but yeah, we're reaching the point where I can pretty close to like afford having additional help and branching out really beyond just being me plus a part-time contractor, working on marketing stuff.

And so something I've been thinking a lot about is like how to approach that. And there's newer, these newer approaches being thrown around from people like Rand Fishkin, who's talking about hiring contractors only and staying like very Just keeping those boundaries up around, you're a freelance or you'll work part-time for us and we will just exchange goods and services and it'll be this very arms length way of kind of building a team as opposed to the more traditional, you're a W2 employee. We provide your health insurance and maybe we're co-located together. So we come into an office together. And dunno if this is reactionary to the pandemic or what, but I'm really feeling very bullish about. Returning back to a kind of partial in-person working together in an office, which is very much not.

It's like this feels like zigging, where in the world zagging right now, because everyone's talking about remote work being the future. And that's everybody is convinced that what we've learned from veteran pandemic is you never have to be in an office ever again. And And I don't know I'm thinking fondly back to the day, early days of Drip and it was a tiny team of us and we would come into this office a couple days a week.

We'd stand in front of whiteboards and map out really hard problems and we'd go grab happy hour some days sometimes. And I don't know.

Cory Miller: [00:36:33] So those are fun days for sure. Yeah, it does feel like a pendulum. There's some pendulum shift and we'll see what happens when it starts to level out like there was so yeah, I digressed, but we can, you can see when the pain pandemic really hit and things cause down the, I'm not one of them, but the PR part of our society and people as humans that need.

The interaction that wanted and then the others like mainly go, oh, I'm good. I like, I get worn out at conferences on to see people, but not every single day. And so that's good stuff. Yeah. And the conversation around the hiring team, or do you stay contractors? I always feel like every business is different and every entrepreneur is different, but it's around in my, on it.

Which is interesting. I think one thing that I found about myself as I really do like collaborating with a team and I missed my team when I left is just having things to bounce off. I still like remote. We weren't remote. We were a hybrid I themes. So it would in this next year around, I think, I don't know about you.

It was a chance for me, even though I didn't take time off. Like you said, you didn't either a chance for me to take a deep breath a little bit and go if I do it next time, what does that look like? Yeah. And

Derrick Reimer: [00:37:51] Yeah.  Value of experience, getting to reflect back and see okay, here are the things that this phase of the business that was really fun. And also being, I think you kinda have to be aware of the nostalgia factor, which puts a rose colored tint on certain things. That's always a, it's probably like a human bias that we tend to, we harken back to the old days and how nice things were. There's some danger in that, but I think. So accounting for that correcting for that, like I think it's still, yeah, it's helpful to reflect back on, like when was I the happiest? Because in my. In my day-to-day work like I'm going to wake up every morning. I'm going to put, based on my work ethic, I'm going to put a certain amount of effort into whatever I'm doing.

So what, how do I want that to look? Which I think is a really important thing for entrepreneurs to ask themselves and not lose sight of creating that work environment that you actually enjoy and get fulfillment out of.

Cory Miller: [00:38:41] Which you and I have seen the entrepreneurs and I've probably been there a time or two that ended up. fleeing something they didn't want to only recreate it, made them miserable. And they like a one day ago I'm miserable. I don't like this because I never intended to one manage people or to have to worry about leases and health insurance and all that kind of stuff. Yeah. Yep. Derrick, thank you Q for all of this, I think it's been so great and helpful with our post-test audience of builders too, like you A lot of the posts that audience are, who I characterize as a developer turned entrepreneur, and these stories are always fun to hear startups and see what you're doing, how you're building SavvyCal. Yeah. I know I asked you or. A do you want to offer anything to the Post Status community because I've benefited from SavvyCal so much. And I know you do have something that I asked about today. Do you want to share that with our crowd? And I'll put it in the show notes as well?

Derrick Reimer: [00:39:38] For sure. Yeah. So we have a sweet discount code you can use for SavvyCal it's promo code, POSTSTATUS, all one word get your free first month free after your seven day trial for SavvyCal. So, you can get a nice long trial on that.

Cory Miller: [00:39:53] Yeah. Put that in the chat now. And hopefully others will take advantage of that too. And I would have SavvyCal world with like me try it out. Derrick, thanks so much. I know you are traveling right now and you've made all this happen. I know it's not easy to do these kinds of things when you're traveling, but I sure appreciate your time and being so open to share about your journey with SavvyCal, and I wish you the best I'm going to be rooting for you because one of my customer in love, I also just love to root for fellow entrepreneurs.

Derrick Reimer: [00:40:21] Thanks so much Cory. Thanks for having me.

Cory Miller: [00:40:23] Okay. Thanks Derrick. I'll talk to you later.

Derrick Reimer: [00:40:25] All right. Take care. Bye.