SavvyCal // taking the awkwardness out of scheduling and making it easy [UP092]

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Jay Clouse 0:02
You know, Eric on the show time and time again, founders talk about the importance of hiring great employees.

Eric Hornung 0:07
And they always say it’s so hard and so important early on to hire the right person.

Jay Clouse 0:13
It makes a lot of sense that is difficult because most founders don’t have experience doing high level searches or hiring top level talent.

Eric Hornung 0:20
And they’re also limited to their local talent pool a lot of the times.

Jay Clouse 0:24
That’s why a lot of founders choose to work with SPMB, one of the fastest growing executive search firms in the country. For over 40 years, SPMB has specialized in recruiting upper management and board members to early stage VC funded startups and larger growth stage companies do.

Eric Hornung 0:39
They bring the knowledge of a large global firm and combine that with the personalized service and attention of a boutique.

Jay Clouse 0:46
They have a dedicated team focusing on the Mountain West and Midwest emerging tech markets. So no matter where you are in the country, if you’re trying to hire top level talent SPMB can help you out.

Eric Hornung 0:56
If that sounds like you, you can go to to learn how they are closing hundreds of C level searches annually.

Derrick Reimer 1:11
One cool quality of this product is that it naturally kind of spreads itself. So every time someone uses the product, they’re effectively putting my brand in front of someone potentially new.

Jay Clouse 1:23
The startup investment landscape is changing and world class companies are being built outside of Silicon Valley. We find them, talk with them and discuss the upside of investing in them. Welcome to Upside.

Eric Hornung 1:51
Hello, hello, hello, and welcome to the Upside podcast. The first podcast finding upside outside of Silicon Valley. I’m Eric Hornung and I’m accompanied by my co-host, Mr. Tweet 100 himself, Jay Clouse. You’re taken the twittersphere by storm Jay.

Jay Clouse 2:08
This has been a fun 48 hours with the new hashtag tweet 100 project, Eric. It is going smoother and faster than I would have anticipated a lot of fun with some no code.

Eric Hornung 2:19
Yeah, you did it live. You built the product live on someone else’s podcast committed a little podultry but that’s okay. I think we had fun. You know, I think you had fun and that product, what you built is so cool. Just its ability to instantly update, to do it retroactively too. I forgot to sign up. Did it three days and it just worked. Very cool.

Jay Clouse 2:43
It’s fun. So dear listener, if you’re listening to this, you’re like, What are you talking about? I have been wanting to spend more time on Twitter for like a year. And by spend more time I actually mean, spend more time creating on Twitter, not necessarily spending more time on Twitter. But I’ve talked to so many creators over the last year who have really catapulted themselves through social media, which I’ve been slow to try to do, because you don’t have a ton of control over that. But it is just such a great way to get in front of new people. Over my birthday, I accidentally had a tweet go viral, and it almost 50% growth in my follower numbers so Twitter works. Tweet 100 is this free challenge, you can go to, you enter your username, it will automatically track every time that you tweet with the goal of publishing one good tweet a day for 100 days, there’s a public leaderboard, built an air table, one of our favorite tools and you can see over 100 day period, how well you do and it’s fun, Eric, it’s very, it’s got a really good viral loop built in, which is just very useful.

Eric Hornung 3:45
Here’s the thing I like about it the most. If you click on the tweet, 100 hashtag, you search it, you search by latest, you can have real conversations with people like you Jay that weren’t tweeting as much as they wanted to. They weren’t sharing their thoughts with the world as much as they wanted to and they’re jumping on this bandwagon. And it’s adding so much volume of thought and ideas and difference to Twitter that I’m having a lot of really good conversations meeting a ton of people through this. It’s actually becoming kind of a little community of new creators.

Jay Clouse 4:12
It’s fun and you are tweeting and you had your tweet about the Ohio rail system it’s good. I’ve been telling you for literally years that you should be tweeting more because your ideas are great, and you don’t put them into tweet formula. I

Eric Hornung 4:23
I feel like this is all a very complicated strategy to get me to tweet more. And that’s exactly why you did it.

Jay Clouse 4:29
This is actually an Upside growth strategy. Getting Eric on tweet 100 another Upside growth strategy was getting Eric on SavvyCal, our new scheduling tool. And our guest today, Eric, we’re talking with Derrick Reimer the founder and CEO of SavvyCal, a scheduling tool with the mission of making things less awkward finding time to schedule with people.

Eric Hornung 4:53
And here’s the thing about SavvyCal. I love using it. But I don’t know if I love using it as much asAnthony Hopday loves using it because the other day on Twitter he wrote the when I look at the visual design of SavvyCal, I turn into an Italian chef and kiss my fingers uncontrollably. My doctor can explain it. She’s baffled, I’m not. I know exactly why the SavvyCal website makes me chef’s kiss and I’ll explain in this thread, willing to throw in the show notes. You guys could check it out. But that’s the kind of love that people give to SavvyCal. And here’s the thing, Jay, there is rhyme or reason for why Derrick’s on today.

Jay Clouse 5:29
Wow. Yes, well, let’s call out the elephant in the room SavvyCal is a sponsor of the show, which happened after we tried the product out and we talked with Derrick, actually. But it’s such an interesting company kind of falls within our wheelhouse. They are funded by TinySeed, guys we’ve had on the show twice now both the founders of TinySeed and Derrick actually co-founded drip with Rob Walling, former podcast guest, between the years of 2012 and 2018. So knows a thing or two about this whole online SAS space, Eric.

Eric Hornung 6:04
It’s amazing. When you’re in this one life, Jay and you run into so many people who are just connecting the dots, man we got TinySeed, we got SavvyCal, the list goes on.

Jay Clouse 6:15
If I could be like Derrick and start two SAS companies Drip and SavvyCal, I would be living this one life, I have to live the best way that I can.

Eric Hornung 6:22
And dear listener, if you want to live the one life you have the best way you can. Go check out our friends at Ethos Wealth Management. That’s to learn more.

Jay Clouse 6:33
SavvyCal was founded in March of 2020. Derrick is based in Minneapolis, Minnesota, a place we haven’t spent a ton of time before. But excited to talk to him about his journey building this tool, which we use now weekly and are loving. It will give you that little preview of the debrief before we even get there. I love SavvyCal. But let’s talk with Derrick, and we’ll get to that interview right after this.

Eric, we got to make some big changes to how we do operations here at Upside.

Eric Hornung 7:00
This feels like an intervention, Jay.

Jay Clouse 7:02
It’s a bit of an intervention. I have to give you some tough love. We’ve had some calendar problems over the last couple of weeks.

Eric Hornung 7:07
I’ve had some calendar problems, you don’t have to throw the third person on this.

Jay Clouse 7:10
I do like to take the blame for you but this one is on you and Eric, I think we have found a solution to our calendar and scheduling problems.

Eric Hornung 7:18
But there are 101 scheduling tools out there Jay that can help you avoid the awkward dance to find a time to meet.

Jay Clouse 7:24
But this tool is by far and away the best one I’ve seen and I have looked at a lot of scheduling tools and I am talking about SavvyCal.

Eric Hornung 7:32
SavvyCal makes it a collaborative effort allowing you to personalize links and allow recipients to overlay their own calendar on top of yours.

Jay Clouse 7:41
It’s going to make booking guests for Upside and even just one on one conversations a complete breeze, you gotta see what this looks like, you got to see how it works because you’re gonna ask why wasn’t it always this easy.

Eric Hornung 7:51
You can sign up for a free account at, that’s And when you are ready to test out a paid plan, use the code upside to get your first month free.

Derrick Reimer 8:16
I have been a software developer for basically my whole career and I’m self taught. So I grew up with a computer in the house. My dad was a mechanical engineer so he kind of got me into it early. I remember I was I think I was in junior high maybe when he introduced me to DAS basic and I made like, you know, recreated the Nokia a snake game and at that point, I was sort of hooked, I sort of knew like, this is something that I’m going to be using as a creative outlet for for probably forever. But I actually didn’t realize at the time that I could do this as a career. For some reason I had this thing in my head that like I would have to learn a language like c++ and sit in a cubicle under fluorescent lights all day long and just write code. And that’s what I thought being as professional software developer meant. And so for some reason I had this this perception in my mind that I never even really seriously entertained it until I was like graduated from college, I got a degree in math. And I sat back and said like, what am I gonna do? I was thinking about being an actuary, works for insurance companies and computes insurance premiums, probably a pretty soul crushing job for a creative person like me, but I was sort of on that path of like, I don’t know, maybe I’ll just go go move to a big city and work for a big company and make a lot of money. But I kind of realized like, I don’t think that actually aligns well with me. So I had to kind of reset and think about what I want to do and and ultimately, like, I don’t I do this this programming thing, this software thing. And that’s what kind of kind of pulled me into the industry.

Eric Hornung 9:52
Did you have like a natural love of math? So I have a I was also a math major who was going to go down the actuarial path, but my inherent love for math was not strong enough to keep me on a path without a end goal. So were you like always a math person?

Derrick Reimer 10:10
I felt like it was the the subject that I gravitated towards the most in school. You know, honestly, like, probably it was spurred on, in part by a teacher that I had, which I think is a lot of times the case. In high school, he was a felt like the kind of teacher that maybe they would make a movie about, like, he was really, he was really inspirational. And he taught a lot of life lessons to his class. And he was like someone that everyone respected like, every other class I was in people were pretty disrespectful to the teachers, overall, you know, like talking in class and whatever, you went to Mr. Freezeins class, you sat there, he had the air conditioner turned down to 55 degrees, or something extremely cold. And everyone just sat there and did their work. And he got people to progress in math, who you never would have thought that person could actually excel. So it was pretty inspiring to be in that environment, I think. And of course, I kind of had a natural inclination towards it so I did really well in that class. It felt like a lot of momentum behind that skill set. And I think that’s probably what, what drove me to pick that among any other like, kind of generic major I could have done in undergrad.

Jay Clouse 11:15
So what was the first step into industry utilizing this newfound interest in coding?

Derrick Reimer 11:21
Yeah, so I would say if rewind back to about 2009, is when I, when I graduated, and reached this point of like, what am I going to do with my life. And then at the time, they were, there was this local software competition. And so I’m from the Fresno area of California, Central California. And the competition was called 59 days of code. And the premise was, spend 59 days building a prototype of something from nothing to something and showcase it in this little like kind of tradeshow like environment. And judges would walk around, look at your booth, you’d, you it was part like technology competition, part business, plan competitions, you would kind of pitch your, your business, your business model, and you’d be evaluated on both the technical side of it, and the viability in the market side of it. So that really appealed to me, I also kind of grew up wanting to be like an entrepreneur, I didn’t really know in what fashion but I was always interested in investing and in money. And in just kind of like, running businesses, I guess, as you know, in a child’s mind, at least. So this, this sort of appealed to me. And I was like, You know what, maybe I’ll maybe I’ll try my hand at this. I’d also at the time discovered, kind of the, the writings and the talks from the 37 signals team. So I was consuming like, every Jason freed conference talk I could find, and I just found them to be incredibly inspiring, like when when they would stand up. And that was kind of in the heyday of them really coming out hard, strong against the venture capital model. And saying, like, there’s another way, there’s this thing called software as a service that you can do. And you can just charge people money for a product that you build. And all it takes is this many customers to get to this level of revenue. And like, just a really simple way of explaining like how the economics of these businesses work was like, I think I can do that. Like, I really felt like it was probably something that I could that I could tackle, given my, my skill set. So I felt like this competition was sort of the first foray like a way to dip my toe in the water of doing this thing. So I did it and ultimately won the competition that first year. And that was a, that was a bunch of validation. That’s pretty much all I needed to

Eric Hornung 13:29
What did you build?

Derrick Reimer 13:29
Really, so I built a, an extremely boring sounding product. It was basically helped software developers and entrepreneurs build documentation for their, for their products. And so think of it like a, an old school form of like, or get book or one of those products. Completely failed to turn it into a viable product in the market. I basically had this idea of like, this feels like something that people would want, but I didn’t really do the right things. I didn’t talk to customers, I didn’t find, you know, figure out what my go to market strategy would look like I didn’t really do any of that in a rigorous way. I did it more in a theoretical way. So I could write a good business plan. But like when it actually came to executing, I feel like that’s, that really highlighted the difference between like, things you learn in the classroom in like a in I got a business minor, also alongside the math major. So like the things you learn in a business plan writing class, very different than what you actually have to do to take something to market and I got, you know, I learned that the hard way on that first time around, but it was still really good experience.

Eric Hornung 14:35
When was the first time you took something to market and it felt kind of successful?

Derrick Reimer 14:38
I would say. So, I worked on a couple products in that, in that time. And each time I built I didn’t really have a full on success from those but I felt like I made progress towards like, gradually doing things the right way. Probably the last product I worked on in that little independent, Derrick’s gonna try to do this on his own phase was a tool I was, I was looking at the real estate space like I bought, I bought a house during this time and like, realize like realtors have really bad tools. So I was like, realtors need better tooling to build websites for things and like, the MLS needs to be more accessible and then I realized how heavily regulated that whole space is but I was pretty naive and young at the time. So I did, like a whole bunch of I was like, I’m not gonna make the same mistakes I’d made in the past, I did a whole bunch of interviews with realtors, like a cold called 150 realtors. And that was, that was quite an experience. I learned like, I got, I got lectured by many realtors saying like, you know, you think you need to be in the industry first before you try to build something for us and da da da.

Jay Clouse 14:52

Derrick Reimer 14:58
It was yeah, but, but it definitely got me outside of my comfort zone. I learned, I mean, that taught me that, like, I gotta, I should probably pick something that I already, in an industry that I already have good knowledge in. First of all, like, if I want to set myself off, I’m on the right foot. But, so yeah, I felt like I made progress during that phase but really the first, the first time I was really on the ride with something that that I really saw get traction was was actually Drip. So through this, like, through this competition, I met Rob Walling, my, my eventual co-founder with Drip, he was a judge in the competition, and I was a participant and he kind of recognized like, your, your building thing, like I was building this like boring piece of SAS software that had a boring business model attached to it. And everyone else was sort of building like, you know, a Facebook clone or something like B2C that seemed more like venture capital style. And so Rob sort of identified like, I think you’re, I think we should, we should talk because I think we’re kind of we had the same similar ambitions on like building these, like, nice bootstrapped profitable businesses. And so we sort of struck up a friendship and kind of a mentorship relationship through that, and, and then that ultimately led to, I sort of reached the end of my line, I was like, I think I just need to go do some consulting, maybe build some, like, build some websites for some local businesses, or just do some kind of like revenue generating activity that wasn’t trying to start a SAS because I sort of, sort of reached the end of my, into my line. And that’s when Rob and I were Rob was like, hey, maybe you should come work with me for a little bit. And that’s how we, that’s how we started our working relationship.

Jay Clouse 17:21
I’m sure we could spend an entire interview talking about Drip. But looking back on that experience, what were your biggest learnings or takeaways that you’ve taken now into SavvyCal.

Derrick Reimer 17:31
Getting to work alongside Rob was, was extremely valuable experience, because I think when you’re looking at from the outside at a company, like at the time, I was looking at Basecamp, and it all looked so easy, it kind of just looked like oh, you just build good software, you put things up on the Internet, and money comes out the other side. And sort of like it’s I think it’s easy to get that perception that like, it’s not that hard. And I probably develop that just by listening to kind of them talk about the way they built their business. I was like, I don’t think it’s that hard. And then you actually get in the trenches. And you’re actually, you know, in a company trying to figure out at each stage, how to bust through the next roadblock, and how to actually, like, be creative and strategic and come up with like, Alright, what’s the next marketing idea that we need to try to execute on? And if that fails, when do you pull the ripcord and when do you start the next one? And what do you do when you’re starting to run out of money in the bank? Like, how do you think about hiring, like, there’s so many things that I just was completely, I just had no experience and no knowledge of and so to get to watch an operator like Rob, problem solve all those things was extremely valuable. So it’s hard to summarize, you know, all the lessons, but I think like, a big one for me is, you know, like, I think the stories that get amplified the most are ones where they are seemingly overnight successes, like oh, yeah, I just I kind of identified this crack in the, in the universe, and I built a product and boom, all sudden, we’re making millions of dollars. And sometimes that happens, but a majority of the time, it’s, you know, I figured out some need in the market. And then I built a product. And then I had to work I had to block and tackle, I had to run the playbooks and figure out what channels are going to work, experiment with them, try to optimize them. And that’s all the kind of unsexy, hard work that goes into building a business but I think it doesn’t get really amplified because it’s not, it’s not fun to talk about. So I think getting getting exposed to like, now this is, this is the these are the tactics and strategies that you use. This is how you think about problem solving. That’s the big thing I took away from the Drip experience.

Eric Hornung 19:43
You’ve talked a lot about this idea of that you’ve worked on boring businesses, which I love and you weren’t creating a Facebook clone you were creating these sexy businesses. So when you think about SavvyCal our calendars sexy?

Derrick Reimer 19:57
I actually think they are a little bit, I don’t know in a strange way, I mean, yeah, if I showed this to, you know, 14 year old Tictokers or something, they would probably say like, ew, no. So, but in, in my mind, like, I think that’s a big part of a part of this work is like, like falling in love with the problem space a little bit, I think it’s, if you don’t really, if you don’t develop that appreciation for it, and like the ability to see like the, the solutions you’re making as kind of beautiful or elegant, then I think you’re gonna have a really hard time staying motivated to, to actually, like, press on and continue solving in the problem space. And I think, I think it’s like, you can probably make almost any problem space attractive like that, in that sense, by really kind of getting a deep understanding of what problems people are having. And then when you build solutions for those problems, and it turns out really elegant, and much better than what’s out there already. To me, that’s what that’s what makes sexy software.

Jay Clouse 21:01
What was the moment that you said, you know what, I gotta do it, I got to make a new scheduling tool.

Derrick Reimer 21:07
Hmm. I came about the idea for SavvyCal actually, from a pretty like analytical point of view. So I was coming off of basically did Drip for five years, and then tried some other things and failed pretty bad at them, which was a good reset off of this like a Drip sold, we required success, and then trying something big and ambitious, and it didn’t work out. And so that was just another like reality check for me on okay, no, you have to there’s still things to learn, there’s still mistakes that that you can definitely make in this journey. So how can you set yourself up for success in the best way possible? And I would say the, the idea right before SavvyCal was was pretty ambitious, it was, it was basically competing with Slack, trying to like, make a better communication tool for teams that wasn’t so interruptive, and more better for deep workers. So I kind of figured out that like, okay, there, there are a lot of reasons I did a whole deep dive a whole, like mega blog post kind of dumping my thoughts about, you know, what are all the things that went wrong in this process. But the big ones like, like coming up with sort of a set of criteria that, that I think I need for the, for the business to fit well with me as a founder, and it was like the product shouldn’t be. So you shouldn’t have to convince an entire team of people to, to use it like it should be usable in single player mode, it shouldn’t be so mission critical that if we have two minutes of downtime, you’re seriously impacting someone’s business like, like running payments for e-commerce or something like that, I just had this started to develop these little sets of criteria like that. And so I sort of took that line of thinking and combined it with the idea notebook that I kind of regularly tend to, where just sort of observe the tools that I’m that are in my current tool chain that I’ve used in the last couple of years and, and what problems I’ve had with those, and the scheduling piece has come up a bunch for me over the years, because I sort of wasn’t an off and on user of calendly, we integrated with them really early on at Drip, because Drip is marketing automation. So people could, you know, feed their scheduling information directly into Drip and send automations on it. So that was like a cool, kind of first integrate one of the first integrations that we built. And since then I kind of use the tool off and on to like schedule customer calls or whatever. But I identified like, every time I go into that tool, there were a bunch of hesitations that I had like, this is gonna be weird if I send the link and how do I make sure that that the person doesn’t book a time that’s really suboptimal for me. And so I have all this like anxiety around using the tool. And I kind of found that over time, other people expressing the same thing. So I’m sort of like a, a process of reducing downlike, potential ideas that I had on my radar at the time combined with sort of this recent learnings of like, this is the type of business that I think fits well with me as a founder.

Jay Clouse 24:06
Because of your Drip experience, I’m sure you were really aware of you know how important it is to actually get customers and adoption on a tool like this. And this is kind of a potentially mass market tool. So how early on were you thinking about like the go to market of this in how you would actually get this in the hands in the workflows of actual users?

Derrick Reimer 24:25
That was a big consideration from, from the get-go is like one I knew that I needed to have a really quick time to build an MVP like I spent some level was the other product that I was working on. And I spent probably about nine months working on the MVP for level like before I could even put it in the hands of of users which honestly if I, if I could rewind time I probably would have tried to make speed that up a lot. Like I think I chose technologies that slowed me down because I was trying to do it the quote unquote right way or the perfect way. And I think the, my velocity suffered so that was. And that was a big takeaway from that is like, I gotta move faster, I still want to build high quality enough software, right, don’t have to chuck away my MVP and rebuild it from scratch. Once I validated it, like I knew I wanted to build the code base that was going to, I was gonna keep building on. So it had to be high quality enough, but like, I needed to move really fast. So I spent, I think was about two months building before I really started showing it to customers. And I sort of looked around at like, what are my, what are my potential, like, unfair advantages that I have in my current situation, and I do, do a podcast and I spend a bit of time on Twitter. So I sort of have these, like little audiences of people who are similar, have similar needs to me. So my very first go to market was like, start talking about like, talk, build and public talk about it a lot to the people who are in my immediate sphere and get them excited about it. And the hope was that I could kind of get enough adoption there. And then the one cool quality of this product is that it naturally kind of spreads itself. So every time someone uses the product, they’re effectively putting my brand in front of someone potentially new. And so that’s I mean, as I’ve like, dissected, what colony’s growth strategy has looked like over the years, I mean, I think, foreign above the number one driver of growth is that kind of viral loop component, the powered by link that shows up on every single booking page. And so sort of my, my initial like, not really sure how this is gonna go thinking was that I would try to get a bunch of people who are in my sphere to use the product. And then hopefully, as I’m working on, you know, finding traction channels running through Gabriel Weinberg’s traction book, and like just vetting each of those blocking and tackling, and my hope was that, you know, the product would sort of continue to spread just by by nature of that viral component, which is, by and large, worked out, like it’s it sort of has has, has worked out that way.

Jay Clouse 26:57
Have you found that it’s easier to convince a non-tool schedule, or like someone that’s not already using a scheduling tool to adopt the technology, or somebody who’s already on some sort of scheduling tool to switch?

Derrick Reimer 27:10
I think so far, I’ve mostly been converting people who have experienced with scheduling tools. And it’s been a really good thing in the sense that I have been able to move really fast, and I’m pretty light on training materials right now, honestly, which I know I will need to, I will need to beef that up soon, like, have videos introducing, like, this is what a scheduling tool is, this is what it does. But so far my like, it’s hard to I feel like it’s hard to position the product for both audiences at the same time, like, my headline is sending your scheduling link shouldn’t feel weird. So like, if someone who doesn’t know what a scheduling link is never used a product like that shows up to the website, they’re gonna be like, what are you talking about, like I, so I’m very deliberate about like speaking to you, you’re a power user, you’ve used, you’ve tried probably multiples of these tools and you’ve discovered this one problem with them. This is what I’m solving. And so, it sort of has been my way of, of niching down a really, really horizontal product, like, I haven’t gone all in saying like SavvyCal is a scheduling tool for podcasters. Because I’ve just felt like, like that would be too limiting. I have already have a super diverse set of people who have made their way into the product and are loving it and using it. So it is a it is a bit of a positioning challenge to figure out, you know, who am I, who am I selling this to directly? So I’ve chosen for now to kind of speak to this particular pain point that is probably shared among different kind of industries or verticals that are using the tool.

Jay Clouse 28:42
What is it about scheduling links that feels weird to people?

Derrick Reimer 28:46
So I think it’s it’s part etiquette, it’s part, partly the way that people put messaging around them. So when you send someone a scheduling link, it feels like you’re pushing it to do onto the other person’s plate. And so if, for example, I’m just opening up my email inbox, and someone reaches out to me and is like, hey, I think you’d really love my services. Feel free to book a time on my calendar. Here’s my calendly link, I immediately have a visceral reaction, like, what, what why do you think that? Like, if anything, I should be sending you my link, because you’re the one who wants to talk to me, not the other way around. So there’s like this, this kind of power dynamic, whoever is making the ask, it’s really hard to actually, like, send the link. But what that means is, people often end up just always choosing the suboptimal, slow route. It’s like, instead of just sending the link, then it’s like, well, let me know some times that work for you. Well, how about Tuesday? Now that doesn’t, that’s not good for me. How about Wednesday? Well, how about next week, I’m traveling next week, and on and on and on. So it’s like, you have this problem, everyone, people are recognizing that like, no, it’s kind of full pot just send a link. And so then they sort of abandon the link altogether. And so what I’m trying to do is strike a good middle ground where It’s like what if SavvyCal can be a more of a collaborative space, like I’ve created the space for us to collaborate on finding a time. And the idea, my hypothesis is that there are ways that the product can ease the potential visceral reactions that people might have to receiving something. And and it truly does should deliver on being more convenient. So when you open up a SavvyCal link, the person who receives it can overlay their own calendar on top of your availability. And that’s just that’s like one of the many features that we’re trying to bake into the product to make it truly a more convenient kind of level playing field type of type of situation, and hopefully encourage more people to feel like they can, they can use the optimal route.

Eric Hornung 30:47
When you were building the real estate product, you mentioned that you cold called 150 real estate agents, and for SavvyCal, so you went kind of heads down for two months, and popped up and said, hey, Twitter, hey, podcast audience, here’s this thing. Did anything surprise you or any kind of feedback that you got not jive with what the width you’d spent two months on?

Derrick Reimer 31:07
So I did actually before I before I started building, I struck up conversations probably with about 20 people or so I didn’t go too crazy for too long on it because I figured like, the best thing I can do is show an actual product to people. But I wanted to get a little bit a little bit of a sense. And honestly, like, it was interesting. Like I still I feel like I’m trying to be a student of how to do these conversations well, and one of the books that I came away from the level experience was the Mom Test by Rob Fitzpatrick recommended to everyone I talked to, I think it should be the the number one book on founders bookshelves because it’s extremely actionable, it’s very short, you can read it in an afternoon and it gives you a really good framework on like, how to talk to customers in a way that you kind of eliminate biases, like you’re not asking questions, like, I’m thinking about building this product, do you think you would want to use that? Like, that’s the worst question you can ask someone. So you want to you want to get you know, ask about their buying behavior, their habits, what what problems they have, you want to basically dance around your actual solution so that you don’t muddy the waters. So I tried to do some of those conversations, but honestly, like, it was pretty mixed. Like I got a lot of people saying like, I don’t know, calendly is pretty good. Like I’m I’m pretty happy with it or like you’re talking to other founders, I think other founders can’t help but put their their founder hat on and kind of armchair quarterback your business a little bit. So we’ll be able to just say, like, strategically, I think you’re gonna have a really hard time entering this market. Like there’s, it’s sort of locked up, it’s really crowded. So it was kind of interesting, like, the feedback I got in that phase was a lot of skepticism. And, you know, I was trying not to, like, pitch my product too much. So I was trying to just, like, get a get a sense for, for how people were feeling without like tipping my hand too much. So I really had to drive forward a lot on my own intuition. Like those conversations, I would say were not extremely helpful, which is, which is a I wish I could say the opposite. I wish I could say like, you could just have to have these types of conversations. And you will get, you know, a definitive answer that aligns with with reality. But I still haven’t cracked that code. Like I don’t, I don’t really know what I could have done differently, honestly, to get to get early validation that lines up with the market validation that I’m seeing now that the product is in the market. It’s hard like a lot of the people who call several people that I talked to that expressed a lot of skepticism and said like I don’t know, I don’t I don’t need a different tool calumnies perfect, it’s everything I need, are now SavvyCal customers like it took them a couple of months after launching. But I got messages from them like, oh, now I get it. Yeah. Okay. Yeah, I’m totally switching oh, yeah, the power dynamic is totally there. So it’s like, this is what I was trying to dry out of you during the validation process, and I couldn’t, so it’s, it’s really hard. And that’s where I think, yeah, like, I’ve become a big proponent of like, you do a little bit of validation. But really, you you have to know you have to have a deep enough understanding yourself to be able to make a bet that there is a need for a new product, and then try to build something as quickly as you can, and then put a real product into people’s hands, because that’s gonna be the best way to get validation as opposed to like trying to spend months having doing customer interviews and figuring that out. Like it’s just, it’s really hard without a product in your hands.

Jay Clouse 34:25
There are other scheduling tools besides Calendly too. Their other competitors, like Acuity and things like this. So when you were conceptualizing this business, like did you think the market was big enough for another tool to also do very well or did you want to take over those customers who were using other tools?

Derrick Reimer 34:41
I do think that the the market is enormous and that was one of the that was one of the really attractive pieces that that made me feel confident that I could enter this I mean, if you think about it, like scheduling, managing a calendar is essentially something that every single working person or even nonworking person has to has to deal with like everybody has time. We all have time and we all have to allocate that time. And so if you think about it, like the market is nearly infinite, for a tool that helps people manage that time better. And so I felt like yeah, I definitely didn’t even feel like I had to steal a single Calendly customer to be able to be successful. Like I could potentially run this business just on just on bringing on people who’ve never used a scheduling tool before. And I think I could build a fantastic business on that. Now I have, because of the realms that I’m marketing this in, I feel like probably over 90% of my current customers had used Calendly before, maybe they weren’t an active user, but they basically kind of owned the market in my initial kind of set of people that I’m marketing to. So there’s, my messaging has been, I’ve had to come pretty strong with an answer to, you know, why should I use SavvyCal not Calendly? But, but yeah, I mean, I think ultimately, it’s a huge market. And I think that’s, I think there there often are these opportunities that people will overlook, you know, a lot of people will look at this space and say, like, well, there’s Calendly and a million other tools. So why why should there exist? Why should another one exist or why do you think that there’s room for another one? And it’s interesting, because we saw this with Drip in a little bit different way. But when we built Drip, there was there were existing marketing automation companies out there, there’s one called Infusionsoft, I think they’re operating under a different name now. And it was like a tool that a lot of people were using, but they weren’t loving it, there was, it was like, it was really good for its time, it was probably it felt like software that came kind of out of the 90s, early 2000s. And it sort of sort of was like stuck in that era. And I think that tends to happen with software as it as it grows. And when by the point that you have 10s of 1000s of customers relying on software, like it’s really hard to change it in big fundamental ways. If you’re looking closely, you can kind of spot even in these giant, you know, industries, giant markets, these tools that are winning, but they’re only winning, because they have a stronghold, some kind of like, you know, they’ve been around for a while they have a lot of customers and so that sort of feeds on itself. But really, is the product, are they innovating? Are they listening to customers and and mutating their product in the right ways? And a lot of times they’re not. And I didn’t, I don’t think Calendly is, is necessarily that much of a laggard, but I think just due to their sheer size, like and not just Calendly, but all the incumbents, their sheer size, and the time they’ve been in the market means that they’re not going to be able to move as fast as a new entrant who’s like really, really listening closely to the needs of this subset of the market. And I think that’s a huge opportunity for entrepreneurs to kind of carve out a little stronghold for themself.

Eric Hornung 37:55
Do you have a team right now or is this a one man show?

Derrick Reimer 37:59
So I have me primarily building the product, I kind of do all the design and backend engineering. And then last November, I started working with Corey Haynes and he came from, he was at baremetrics. And he kind of went out on his own was doing some consulting. And luckily, I was able to snag some of his time. So he’s been helping out and it’s been a, it’s been a major help, to be honest, to have to have another smart person thinking about marketing initiatives, so I can stay focused on the product. And then I just hired my first support person. So even though our support is not extremely busy, it was still like a, the there was a certain mental burden every time I’d wake up and have to check the support inbox. And if there were five things in there, I might spend, I have a hard time like letting those sit for half the day. So I would spend my prime morning time working on a couple of these support tickets and and then maybe spur on conversations before I know it my mornings gone. And that was just that had to stop. So even though I don’t have probably a full day’s worth of support tickets to respond to every day, it’s been a major help, kind of bringing on someone to, to man the the tier one inbox.

Eric Hornung 39:11
Well, congratulations on, is that a full time hiring?

Derrick Reimer 39:14
It is, yeah and I went I went through service. I can mention here that They basically a productized service around SAS customer support. So they they do the sourcing of support reps. And they vet them, they train them, they hire them and they kind of manage them. And so I get a dedicated rep that I pay a flat fee to them for it. But there’s a little bit of redundancy baked in so his manager is gets trained up on the tool as well. So in the event that like we need to add, we need to expand the team or my rep moves on. There’s some redundancy baked in so that’s I’ve been I’ve been really enjoying the service so far.

Jay Clouse 39:51
When I signed up the try my trial of SavvyCal. What I really loved was that you guys had like an indefinite free trial. It was like you are on a free trial until you decide that you actually want to use the product, we’re not going to force you to like a 14 day window, I thought that was really innovative. You guys don’t have just like a free version of using the tool in competitors, like Calendly do have that so that was obviously a thoughtful decision and I’d love to hear why you went the full paid route.

Derrick Reimer 40:21
I think it’s very difficult for bootstrappers to pull off a premium play. And I would confess, I’m sort of a hybrid bootstrapper, like sort of self funded a little bit, but also I have some investment money, so but it’s not like venture capital. But still, like I would consider myself sort of in the bootstrapping camp in the sense that, like, I don’t have infinite runway or infinite resources here. So the risky thing about a premium play is it’ll obviously, like cannibalize some of your ability to, to monetize and, and I had a product that I built, called StaticKit that sort of had a free plan baked in and it was a, it was like a forms tool. And so anything under 100 submissions per month was free, you could just use the product. And when I was building that, I found that like, over 90% of people who use the tool didn’t start out as heavy users. And so they, they were like on the free tier, and maybe it would take them a year before they graduated into the fully paid tier and that is just so brutal. That was that was brutal for me as the person investing in the tool like, like, it does require you to have a really long term view on on like a funnel that we can have a very low digit percent, people actually converting into a paid tier. And so I decided this time around, like, nope, I’m gonna charge for it out of the gate, I want to attract the people who are most who are most hungry for a better tool, like the people who are the kind of the early adopter set, the people who are power users, who understand the dynamics, and they’re willing to pay for things. And my plan is bad, sort of, to build up a good solid base of revenue off of these types of folks. And then gradually as kind of the, as the circle expands, and you know, now that we have kind of a base of a revenue where like, we could sustain on this, like, if if premium does, like really cannibalize a lot of our current conversion funnel, and like, it changes the dynamics of the business, at least we have this solid base to operate off of. So actually, I mean, we’re probably around the time, in the next couple of months, Corey, and I keep keep batting this around. Like, it’s probably time to revisit that discussion of like, at least, when is the right time to launch premium? Because I see it as, it’s not a matter of if it’s a matter of when, but I wanted to make sure that like the business will be sustainable, first and foremost, before like, before playing with that because ultimately, I see premium as it is a marketing channel, and it has a certain cost attached to it. And the price tag can be quite high. So it’s why it’s, it’s a bit risky to roll out, but probably probably getting close to time to revisiting that.

Eric Hornung 42:59
If you didn’t take VC money. I mean, you called yourself a hybrid bootstrapper. What kind of money did you take? Was it individuals or some sort of all VC?

Derrick Reimer 43:09
Yeah, so I joined TinySeed, which is kind of one of the there’s TinySeed, there’s calm fund, there’s sort of this new class of like, I guess, funding for bootstrappers funding for Indie SAS, you can tell like this, the terminology around this stuff is still not mature yet, it’ll probably be funny to listen back to this in five years or something when like, we have a word for this. But um, yeah, basically, like these funds, sort of, fundamentally, they’re investing in companies that are ambitious, that want to want to grow, but like don’t have unicorn sights set. So like, I want to, I want to build a multimillion dollar business. And so that that aligned well with with TinySeed is like looking to invest in ambitious companies. But but don’t necessarily carry that that mandate to go to a billion.

Jay Clouse 43:56
The SavvyCal product, you know, I’m, I’m one of your users that switch from Calendly to SavvyCal and I did it on the merit of the product, even though I love Calendly. And the difference for me was design user experience. And Calendly billion plus dollar company with a whole team will probably continue to innovate in those areas as well. So how sustainable is like a user experience advantage long term as a two and a half person team?

Derrick Reimer 44:25
Yeah, that’s, I like to rely on the fact that right now, I can maintain an extremely high velocity. So I see the velocity piece as critical to my continued progress, I guess, because I think you’re right, like they, unless they’re totally mismanaged. Like all the products in the space should theoretically continue to improve over time. So then the question is, how quickly how quickly do they respond to, to the demand of like a better user experience and my just my, my knowing kind of how the inner working interworkings of software companies that reach that couple 100 and up place, it’s really difficult to do that. Now, it’s not impossible, but it’s difficult. And I know right now, my, my advantage, I’m tiny, but I’m really nimble. And I think that’s, that’s the advantage that a lot of little guys like, like SavvyCal or any other like small company, or just like an entrepreneur who has an idea, and has some chops on being able to build and design, like, you can kind of run circles around large incumbents, because the distance of like decision making is just between your two ears, you know, you can, you can make decisions really quickly, you can spend a couple hours designing a really nice interface, then you can go implement it and that and ship it to production that night. And that kind of like that kind of velocity and pace of responding to to customer demands and being creative and, and shipping like it’s just large companies simply can’t do it. And so I think that’s something that a lot of that entrepreneurs need to be sure to leverage like, don’t slow yourself down to the pace of, of a larger company with a bunch of process and a bunch of cruft basically like that’s, that’s your advantage to seize at this at this stage is to be able to move really quickly.

Eric Hornung 46:08
Cruft is such a phenomenal word. How do you think about you mentioned you want to be a multi-million dollar business, I think about maintaining the benefits of being tiny and nimble, while also having that ambition of being large and scaled.

Derrick Reimer 46:25
Yeah, this is a question that my podcast co-host and I revisit, feels like almost on a weekly basis now. It’s like this fundamental question of, what do you want out of this, right? So there’s, I think a lot of us get attracted to, to building these like little SAS companies, because of all of the freedom that they can afford you, freedom to structure your work, how you want freedom to work on the the problems that you’re interested in, and do your craft and continue to do that. But ultimately, like, if you’re successful, you’re going to have pressures on you, right? You’re going to have the pressure to well now that you have so much work to get done, you should probably hire some people to help with those things. And once you hire people, it kind of forces you to wear your wear your manager hat a little bit more and your maker hat a little bit less. And so there’s something I think about a lot and like there, there are, you know, CEOs who still write code, but it’s, it’s pretty rare. And so what do I want out of this? I’d say like, I don’t, I don’t think I have that, that answer. The question fully answered for myself and I think it’s something that is continuing to evolve in my mind. But I think that I can, it like watching my co-founder, Rob with Drip, he never wrote code for the product at all. And it was sort of a deliberate thing like, I chose Ruby on Rails, and Rob had never even written Ruby before. So it was sort of like a way to guarantee that he wasn’t going to get sucked into that side of the business. And he was really just going to focus on the other parts of it. And I could, I could see myself falling in love with the craft of building a company, I think is, is also a you can still be creative. And I get a lot of joy out of watching my team members succeed and and producing, performing their craft at the highest level. So I think that that’s something that I could see myself morphing less of like, individual contributor creator into a facilitator of other team members creating, the tricky part for me is figuring out when’s the right time to deliberately make that transition. Like right now I’m, I’m very close to hiring my first engineer to help out and the first question is like, why am I hiring this engineer? Am I hiring them to offload some of my work or am I hiring them to move faster to like, add another engineer so that me and that person are both building at the same time. And I think, I think it’s wise to like, start with the first but but gradually move towards the second, which is like, I’m gradually delegating this responsibility. And this person’s taking more ownership of the product, which is a hard thing to do. It’s hard. It’s hard to delegate those core things that you’ve owned for so long, but something I want to push myself on. But for me, the question is, when is the right time to do that? Because I know it’ll slow me way down. And we just talked about velocity. I think that’s so important right now. So it’s like, when is the right time to take the hit and move a little bit slower, bring someone on train them get all of this knowledge transferred and ramped up? I’m not sure. I feel like it’s, I don’t think there’s ever going to be a right time. So it’s probably just, it’s probably just a matter of drawing a line in the sand and saying, this is what we’re gonna do. And yeah, for the next quarter, we’re gonna move a little slower, but it’s in the name of of long term.

Jay Clouse 49:44
Do you do all the design yourself?

Derrick Reimer 49:45
I do. Yeah.

Jay Clouse 49:47
Crazy. That’s like, that’s a non-trivial. I mean, it’s it’s a huge part of the experience, and it’s really well done and you don’t have a lot of software engineers who can design to that degree.

Derrick Reimer 49:56
Yeah, yeah. Thank you. I it’s it’s always been something that like I love dealing with the whole stack. And I think, yeah, that is kind of I’ve discovered that’s a rare, that’s a rare thing. Like a lot of engineers just aren’t necessarily that interest. I think there are a lot of engineers who would probably be capable of learning design. I think it is just a skill that can be learned but I think it’s it is many hats, so many hats to wear. I think it just yeah, from from hosts, most people who are like doing hardcore and backend engineering just don’t have an interest in the front end. So I do feel like that’s one of those, one of those unfair advantages is just like that. I’m crazy enough to have this this interest in both the the design side and the backend stuff.

Jay Clouse 50:38
Last question for me that I sometimes forget to ask. You’re based in Minneapolis, what’s the Minneapolis startup scene like? And has that played any role in SavvyCal’s growth?

Derrick Reimer 50:49
It hasn’t played a role yet, since I haven’t really hired locally, but I would say it’s a, it’s a small, it’s a relatively small tech scene here. But when we were at Drip, Drip was actually a well, lead pages that that purchased Drip was basically a local team, like they weren’t really doing the remote thing. So they were when they were sourcing talent they were trying to hire locally here. So it’s definitely definitely found some some really good engineers built out our team at Drip during that kind of transition phase. So I feel like it’s definitely like, possible to, to find really good engineers here locally, this is actually a this is something that I’ve been giving thought to and I still don’t, it’s an open question in my mind, you know, as we’re coming out of kind of a pandemic. And so many companies are like really doubling down on this, like remote, remote work culture, I’m still questioning in my mind, whether that’s the kind of company I want to build, where we never actually, or we rarely actually see each other face to face. If I think back to my favorite phase during Drip, it was when there were four or five of us that would come into an office a couple days a week, and it wasn’t anything rigid, we were still we still had flexibility. Like, if I wanted to go drive to the coast and work from a coffee shop over there, no big deal, that’s fine. But like, on your typical week, on average, we would kind of be together about two or three days, and we’d stand in front of a whiteboard. And we’d solve really hard problems, and we’d commiserate over a really tough, you know, customer support email, and there was just this camaraderie that we built up, that really made it a fun experience for everybody involved. And I think that’s, it’s really hard to foster that level of camaraderie over Slack, you know, over over Zoom or whatever. So I think that’s something that I’m considering is like potentially trying to hire folks on who are going to be on the core product team and try to find them locally first, so that we have that option, that ability to be together in the same room remains to be seen if that’ll be feasible, because obviously, that shrinks your pool quite a bit. And forces you to to, you know, to have to be willing to find people who don’t check all of the boxes, like the odds that we’ll find like a senior level elixir engineer, with all of the like, long checklist of ideal skill sets, probably pretty low but maybe that’s okay, maybe that doesn’t matter. I think what matters most is finding someone who’s going to be a good fit for the company and people can learn new skills. So that’s something I’m thinking about.

Eric Hornung 53:21
As company builders today, it’s cool that we have the we’re lucky enough to have the opportunity to do either, right or is it wasn’t a decision node at all, even probably 15 years ago. Derrick if people want to learn more about you or want to check out SavvyCal, where should they go?

Derrick Reimer 53:40
Sure. So to check out the product and you can probably catch up with me on Twitter. I’m @derrickreimer on Twitter I hang out there almost every day and I blog at, occasionally blog at

Jay Clouse 53:56
Eric, do you know what my favorite part about podcast advertisements is?

Eric Hornung 53:59
That people actually listen to them?

Jay Clouse 54:01
Wow you read my mind. It’s almost like we’ve done this twice now. Yes, that people actually listen to them. Look, you’re listening right now, dear listener.

Eric Hornung 54:09
And me, I’m listening to. I’m listening to you, Jay. Here on the Upside podcast.

Jay Clouse 54:13
And if you have a message that you want to share with the Upside audience, people who care about startups, investing, the middle of the country, this is a really great place to put that message.

Eric Hornung 54:22
Because people will listen to it. And if you have an event, or you just want to get something out about your brand, your hiring. This is the perfect place for the That’s our classified ad that can run on one to five podcast episodes.

Jay Clouse 54:38
That’s right. Typically we lock in sponsors for longer sponsorships, but we wanted to make this accessible to you and your message. If you have a message to share with our audience, go to and get your ad on the airwaves.

Alright, Eric, we just spoke with Derrick Reimer reason himself, the CEO of SavvyCal, where do you want to start this debrief?

Eric Hornung 55:05
I think that’s the first guest we’ve ever given a nickname to outside of oh no, even Jackie Demonte, we didn’t give her a nickname. We just gave her a paradox, the Demonte paradox.

Jay Clouse 55:14
Wow, which is arguably better. Having a whole paradox having a framework of methodology and idea associated with you probably about a nickname everybody has nicknames.

Eric Hornung 55:22
That’s true. Sorry, Derrick. No paradox for you. Anyway, I want to start with, let’s start with the product. This is a product first company, they’re building the product first. And Jay, you and I are avid users of the product. So this might even come off as a little bit of a rah rah piece here, because of how much we love using it, how simple it makes it for us to schedule and I am notoriously difficult to work with in the scheduling department.

Jay Clouse 55:46
Here’s the thing. I use Calendly for years and I love Calendly, I was a huge advocate for Calendly and still am an advocate for calendly for a lot of people. But the fact that I switch over to to SavvyCal and have zero regrets, I’m glad I made the switch, even though I think I’m paying the same or more if not less, that’s a huge testament in my mind that like just goes without saying the product is great. It’s simpler to set up than Calendly. They just rolled out an API, which makes it really great because now it’s playing with my notion really nicely. And my research for this episode is just all beautifully created from a product side. And besides that, what I love about this product as a potential investor, or somebody who would look at this as an investment opportunity, it has this built in network effect that Derrick talked about, because people using SavvyCal are spreading the word of SavvyCal, just by using SavvyCal, like you’re scheduling with people who are using the product by using the product. It’s very, very visible. The growth loop is very straightforward and I think that’s great for a tool that has a lot of competition. Let’s be honest.

Eric Hornung 56:55
And maybe that’s something I want to jump into here. That might be a bit of a shadow for me, or maybe it’s not a shout out. Not really sure. There are so many calendar apps. Everybody has one HubSpot, has one Calendly, who you mentioned earlier, it feels like there’s another one on product on every single week. I don’t know if that means that this markets so big that if you can find a little niche and do well in the market, that it’s going to be a great business, it’s going to do well people are going to like it, it’s going to see those network effects or if it means that you can both fly high and get burnt out quickly. It’s something that I have a bit of concern about is the industry is tough, but it’s also huge.

Jay Clouse 57:38
Yeah, it’s a great question, because literally just this week, I saw that app Sumo published a scheduling tool on Product Hunt. So yeah, I mean, you can look at Calendly, for example, a multi-billion dollar company, the scheduling app, so you can deduce the size of the market from that. But everybody, everybody’s scheduling things, right. So there’s a ton of space, but I hear you and I agree with you have the shadow of even if you have a really strong position, some other player that comes into the market, take it from countless perspective, when SavvyCal came in, it kind of forced Calendly to innovate even on their own UI, like I’ve seen improvements in the Calendly UI faster than I did, after using the product for years, which I think is a symptom of competition, raising expectations and forcing the entire space and the different people competing in that space to up their game, which is great for the user would be challenging, I’m sure for the creators of tool.

Eric Hornung 58:33
And we also see things like I believe it was they shut down, if I’m not mistaken.

Jay Clouse 58:39
I did see that. Yeah.

Eric Hornung 58:40
So I think it’s a competitive space. And that’s why I think that the way that Derrick is going about it is probably the right way. He’s more in the bootstrap side of things and the VC scale at all costs, hyper scale going to grow to however long and that’s how Calendly did it at the end of the day, too. You know, they spent 17 years building that company up. I think that the low and slow growth method here when there is so much competition, it becomes all about being a survivors game, can you survive?

Jay Clouse 59:08
And that’s why I think the design of this is so important. As much as I love design for all products, it just matters more in certain spaces. And for this to be a mass market product, it has to be really well designed and intuitive and easy for someone to use who’s not in this world of SAS and business all the time like we are Erica has to be really intuitive and really easy to set up and it was.

Eric Hornung 59:32
One thing that I’m looking at as SavvyCal moves forward here is something that popped up on Twitter that I hadn’t really considered until we had the conversation with and that episode was Upside Episode 89. It aired on June 30 so you can go check that out. Patrick Lightbody was the CEO there. He actually reached out on Twitter after we were talking about SavvyCal. We said, look, we’re sponsored by SavvyCal. We love it. And he goes, No, no, no, we’re not competitive. We’re complimentary. So that got me thinking about what is the future calendars stack look like versus singular calendar app. And if Reclaim and SavvyCal can play well together, and maybe there’s a third leg of that stool. That might be where the real value is and having multiple these tools specializing and making the best user experience.

Jay Clouse 1:00:25
Can confirm I am actively using Reclaim, SavvyCal, Google Calendar and Notion right now and they’re all playing together beautifully and I love it.

Eric Hornung 1:00:34
Like an orchestra.

Jay Clouse 1:00:34
Like an orchestra it got strings, it’s got horns.

Eric Hornung 1:00:37
What song would they be playing? If that was an orchestra?

Jay Clouse 1:00:39
Did it it? Did it? Did it it did it it? Did it? It did it? It? Did it? Did it?

Eric Hornung 1:00:49
Four Seasons by Vivaldi?

Jay Clouse 1:00:52
I, yes, that’s that’s the feeling that I get when they’re all playing together nicely. Switching gears a little bit here. A lot of times in these debriefs, we talked about the founder and so I want to spend a lot of time talking about Derrick. And, boy, what a pedigree coming from the trip acquired by lead pages for an eight figure exit, according to Ron Walling, so at least $10 million to go from co-founding that company to now building this company. This is the type of founder that I’d be interested in backing, especially knowing that Derrick is on the technical side here, it’s really hard to find somebody with the technical expertise to build something to scale to this degree. And not only does he have the technical expertise, but he is the one that’s doing the design in this tool as well. So those are big, big pluses. I like that he’s kept the team lean so far, that makes this a very bootstrappable company, probably to get to the Calendly level of scale, he’ll have to hire. And so that is a skill that we’ll have to see, you know, how he builds on it and how well he does with it. Admittedly, in this interview, you know, he said, there’s something that he’s spending more time doing, that is challenging, but being able to cover the tech and design side of the product itself is a really great start.

Eric Hornung 1:02:10
Yeah, I mean, Derrick is a rock star and building this out. I think he wants to ship features faster, and do all that so there will be some hiring involved to grow this thing. But if you’re not going down that kind of hyper scale route, how fast you push forward that throttle, it’s kind of up to you, do you want to hire one person and move a little slower? And that’s okay, and grow a little smarter, iterate a little less? That’s all completely okay. There’s the optionality to do and grow however he wants in this model. And that’s one of the benefits of working with someone like a TinySeed.

Jay Clouse 1:02:45
Yeah, sometimes, having more cooks in the kitchen doesn’t necessarily make you go faster, depending on how complex the tool is. And this strikes me as something that a small development team can build on very quickly and move pretty quickly. He mentioned, you know, in the interview, that Calendly, slow as it had been for a couple of years, probably because of some technical debt, some legacy code, it’s just harder to innovate on those types of things so staying lean can be can be helpful here.

Eric Hornung 1:03:16
Well, I think all in all, it’s fair to say that we are big fans of SavvyCal. We have some reservations about the competition, but like the way that Derrick is building the company, so Jay, what do you want to see in the next 6 to 18 months as an active user of SavvyCal and investor?

Jay Clouse 1:03:30
Well, probably slightly different answers. As an active user, I actually have no complaints, there were a couple of requests that I had sent to Derrick, one of which I believe he put into effect, the other was already in the product, I just didn’t quite understand it. So oh, here, okay, here’s the answer. I think that the onboarding, when signing up, could be a little bit stronger so you can learn all the functionality that does exist in the calendar, that may not be as obvious. So I think they will make the product better as a user. As an investor, something that Derek said in the interview was that they’ve had an easier time getting people to switch to SavvyCal than to adopt a scheduling tool generally. So I would want to know what their strategy is there for creating new users, or if that’s definitively just not part of the strategy, because the shadow would be if they’re having the most success getting people to switch, that user might also be apt or quick to switch to the next tool that gets launched on Product Hunt, because they might like new tools, you know, so I would want to know a little bit about that retention, and how they’re going to reach a new audience outside of existing scheduling users.

Eric Hornung 1:04:41
And I think that plays into my feature idea, which I’m going to kind of go down a little bit more granular than looking at new scheduling users. So I work in an old industry where not where I’ve probably seen three scheduling links in the last six months. It doesn’t happen.

Jay Clouse 1:04:56

Eric Hornung 1:04:57
Everything is back and forth and through secretaries an email and here’s some times at work.

Jay Clouse 1:05:02
I hate that.

Eric Hornung 1:05:05
See now, you know I suck at scheduling. Derrick talked about himself being a hybrid bootstrapper. He’s kind of a bootstrapper but he also took capital, I think there’s probably a place for hybrid scheduling, where you’re using a scheduler, but it doesn’t look like it’s other people. And maybe that type of tool development can help solve some of that answer, Jay. Because in some industries, it’s just socially not acceptable to send a scheduling tool or a scheduling link. Yet, it will be, but not yet.

Jay Clouse 1:05:33
Well, we’d love to hear what you think about this episode, dear listener, and you can even try SavvyCal out for free they have an unlimited free trial for you to kick the tires, you can go to to get that offer. Let us know if you think about the tool. Let us know what you think about this episode and this company as an opportunity. You can tweet at us @upsidefm or email us and we’ll talk to you next week.

That’s all for this week. Thanks for listening. We’d love to hear what you think about this episode. So tweeted us @upsidefm or email us and let us know. You can learn more about us and browse our entire back catalogue of episodes And if you love our show, please leave a review on Apple podcast that goes a long way in helping us bring high quality guests to the show.

Interview Begins 8:16
Debrief 54:58

Derrick Reimer is the founder and CEO of SavvyCal.

SavvyCal wants to take the friction and awkwardness out of scheduling time with people. They’re an indie SaaS company with a little bit of financial backing from TinySeed and a few angel investors.

Previously, Derrick co-founded Drip, which was acquired by LeadPages. He hosts The Art of Product Podcast, where he shares what he is learning building the company.

We discuss:

  • Starting at the software industry 11:15
  • Drip Before SavvyCal 14:35
  • Business Takeaways 17:21
  • Sexy Software Business 19:43
  • Idea on SavvyCal 21:01
  • SavvyCal Reaching it’s Market 24:06
  • What’s Weird About Scheduling Links 28:42
  • SavvyCal’s Feedback 30:47
  • SavvyCal and it’s Competitors 34:25
  • SavvyCal’s Indefinite Free Trial 39:51
  • Hybrid Bootstrapper 42:59
  • SavvyCal Wanting To Be A Multi-million Business 46:08
  • Minneapolis Startup 50:38

SavvyCal was founded in 2020 in Minneapolis, Minnesota.

Learn more about Savvycal
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SavvyCal is the most intuitive and powerful scheduling tool on the market. In fact, we just started SavvyCal to book interviews with our guests!

You can create personalized links in seconds and even allow recipients to overlay their calendars on top of yours.

You really gotta see how this works, and you’ll wonder why it wasn’t always this easy.

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