In episode 718, Rob Walling and Derrick Reimer tackle listener questions about giving up on ideas, competing in crowded markets, and developing painful features. They also chat about SavvyCal’s recent design refresh, finding founder-market fit, and whether Derrick has retired from podcasting.
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Topics we cover:
- 3:59 – Which feature felt harder and took longer than imagined?
- 9:14 – When is time to give up on a SaaS idea and move on?
- 17:51 – Finding customers in crowded markets with large incumbents
- 23:32 – Has Derrick officially retired from podcasting?
- 25:57 – Handling competitors that are copying differentiating product features
- 28:48 – Evaluating SavvyCal’s refreshed design
- 31:10 – Considering vertical vs. horizontal SaaS for SavvyCal
- 34:05 – Why did Derrick decide to pursue the idea for SavvyCal?
- 40:19 – Finding “founder-fit”
Links from the Show:
- The SaaS Playbook by Rob Walling
- TinySeed
- Derrick Remier (@derrickreimer) | X
- SavvyCal
- Group scheduling mode
- The Build In Public Podcast
- The Art of Product Podcast
- 8 B2B Marketing Strategies That Got My Startup to $10 Million (and 1 that FAILED)
- Finding My Next Bootstrapped Business Idea
If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!
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Is your outsource development team dropping the ball? Maybe you’ve worked with a team that just couldn’t grasp your vision and needed constant oversight because they weren’t thinking strategically or maybe you ended up wasting hours micromanaging, often needing to jump on late night calls across massive timezone differences to get alignment, and in the end, they delivered a sluggish app with a frustrating UI that didn’t come close to the solution you had envisioned. If any of that sounds familiar, you need to reach out to our sponsor, DevSquad.
DevSquad provides an entire development team packed with top talent from Latin America. Your elite squad will include between two to six full stack developers, a technical product manager, plus specialists in product strategy, UI, UX design, DevOps and QA, all working together to make your SaaS product a success. You can ramp up an entire product team fast in your timezone, and it rates 75% cheaper than a comparable US-based team. With DevSquad, you pay month-to-month with no long-term contracts. Get the committed, responsive development team that your business deserves. Visit devsquad.com/startups and get 10% off for the first three months of your engagement. That’s devsquad.com/startups.
Welcome back to Startups with the Rest of Us. I’m your host, Rob Walling. In this episode, I sit down with Derrick Reimer, and we tackle I think it’s like six or seven, maybe even eight questions that were submitted on Twitter. When I let folks know Derrick and I were going to be having a conversation, got some really interesting questions from listeners just like yourself, questions about how Derrick validated or whether he validated his idea for SavvyCal, the most painful feature he’s built for SavvyCal, how his redesign worked out, what it’s like to have an opensource competitor raise a bunch of money and compete with him, and the key question you’re all wondering, is Derek looking to get on a regular weekly podcast again at some point in the future? Stick around to the end to find the answer to that, and with that, let’s dive into my conversation with Derrick.
Derrick Reimer, it’s great to have you back on the show.
Derrick Reimer:
Always a pleasure to be on the mics with you.
Rob Walling:
Little do people know you are founder of SavvyCal and an author of the upcoming book, I’m Obsessed with Kerning.
Derrick Reimer:
That’s a good one.
Rob Walling:
The reason few people know that is because you’re not working on the book, but you are in fact obsessed with kerning. I had never heard the word kerning before I met you.
Derrick Reimer:
Really? Yeah. I’ve always had a thing for fonts. I don’t know why. That was one of my childhood obsessions with my computer was exploring the world of fonts. Maybe in another life I could be a font designer.
Rob Walling:
Yeah. Oh, I could see it in this life.
Derrick Reimer:
Yeah, I probably could, not this season.
Rob Walling:
After you exit SavvyCal for 50 million, you’re just on the beach designing fonts. I feel like you might’ve been called a nerd when you were younger, huh?
Derrick Reimer:
Maybe a few times, yeah.
Rob Walling:
Few times? When you were obsessing about fonts? That’s great.
Derrick Reimer:
Fonts, accounting software.
Rob Walling:
Oh, yeah, doing things in Photoshop that may or may not have a statute of limitations on them, meaning trying to replicate currency.
Derrick Reimer:
Yup. There was that.
Rob Walling:
We won’t talk about that. It was a hypothetical. So I was going to have you on the show and I had three or four topics I thought we could cover, and I was like, “You know, I might want one or two more.” So I go to Twitter. I mentioned that you’re coming on the show and just inundated in the best way with really good questions, topics, suggestions from a swath of people. So that’s what we’re going to do. We booted all my topics. Those will go into some other, I don’t know, maybe I’ll talk about them in the future. Maybe we’ll do them next time or whatever, but I want to dive right in.
It won’t be a lightning round per se, but we probably do have, what, 8, 10, 12 things, not necessarily topics, questions to dive through. So our first one is from KP on Twitter, and we just met KP MicroConf in Atlanta. He is the host of the Build in Public Podcast, and his question for you is, “What’s the most painful feature that you’ve built for SavvyCal, pain as in which took longer and felt harder than you imagined?”
Derrick Reimer:
I think we actually just built this feature, and it launched this past month called Group Scheduling Mode. So this is a feature that allows you to basically specify a link that allows multiple people to book the same time slot. So think of a webinar or a group coaching call, and it seems simple on the surface because it’s just a setting like what’s the maximum number of people you want to allow to book this, but under the covers, it basically touches almost every part of the scheduling infrastructure because we have so many places where we assume that only one person can be on a calendar event at a time booked through SavvyCal, I guess. Obviously, you can have calendar events with multiple people on them, but generally, the product assumed that when a booking occurs through SavvyCal, once that booking is in place, that time slot is blocked and not available for others to hop onto.
So adding this meant, okay, so someone can book a time slot, and then if another person picks that and it hasn’t reached the limit yet, then they basically hop onto the calendar event, which is kind of a separate action. We need to notify in a different way about that. Then if that person decides to reschedule, well, now we need to remove them from that event and spin up a new event if it doesn’t exist already, but if they reschedule from an existing time slot to another time slot that already has a person attending, then we’re doing this lateral translation move of moving this attendee from one existing event to another.
So you can see all the permutations that this takes. Ultimately, I feel like we’re in a better place. We had to refactor a bunch of the guts of the scheduling infrastructure to kind of pass around, change events, I guess you could say like one type of change is when an event is scheduled, another is when an attendee is added or an attendee rescheduled. So we kind of formalized the underlying infrastructure for this, which will set us up for being able to build integrations easier. So I’m happy that a lot of the work is not just for this feature, but, boy, it ended up a lot gnarlier than we anticipated at the outset.
Rob Walling:
So when you quoted your manager an estimate of two days to complete it, how quickly did you realize, “Uh-oh, this is going to be a problem”?
Derrick Reimer:
Yeah.
Rob Walling:
I ran into a few of those, the iceberg problem of getting in and discovering. That’s the beauty, honestly. So I used to be a consultant. I was a contractor, and we would give estimates, and it’s like, “We bill 150 bucks an hour. I think it’s going to take probably 16 hours,” I might say or however many, and it’s like, “All right.” So the client’s like, “All right, 16 hours.” Sometimes you get six hours into that 16 hours and you realize, “Oh, no, this is an 80-hour project,” and you have to go back to them and say, “Look, we either don’t do this and we just lose the six or we move forward,” and it got even worse on big projects when you’re like, “Oh,” you estimate all these webpages or whatever, and you estimate 400, 500, 600 hours, and then you get in and you realize, “I was off by 10, 20%.”
So that’s the beauty of being an entrepreneur is that you’re able to make that call and you could have just pulled the plug. You could have gotten three days in and been like, “You know what? This is not worth it,” and just killed it, but I’m guessing you did that calculus and you were like, “No, it’s worth doing,” for all the reasons you just said and you kept moving forward.
Derrick Reimer:
Yeah, there were definitely a few points where, because I never want to fall victim to the sunk cost fallacy if at all possible, so even a month in stepping back, and Taylor and I are talking about this daily as the project is going on and we’re talking about different snags and roadblocks that we’re running into and things that we know are going to expand the scope, and we would kind of regularly check in like, “Is this still worth it? Do we still want to do this?” I think it was only because we could see the follow-on benefits and the way that it makes the infrastructure better not just for this feature that kept us going because otherwise may have just pulled the plug and said, “Sorry, you can’t do that kind of thing with SavvyCal,” which sometimes you have to make those kinds of hard calls, but in this case, this one’s been requested basically from day one, and we have a huge long list of people who wanted it. So it was kind of like, “Yeah, if at all possible, we should probably add this.”
Rob Walling:
Are there any other calendaring apps, scheduling links that do that? Because it seems like that would be not for mere mortals.
Derrick Reimer:
Yeah. I was actually kind of surprised. Calendly does it, and it’s implemented similarly, I think. As part of our research on what might users be expecting, we took a hard look at how Calendly’s handling some of these changes and what happens when the last person on a group event reschedules, does the event just disappear? So we learned about and saw that all the edge cases they had to think through, we kind of teased them out in our testing and we’re able to get a good sense for, “Okay. I think they had to solve a lot of these heart problems too. We’re not just complicating this thing,” but as far as the others, I’m not sure. I think, yeah, definitely anyone else who has it had to go through a lot of pain.
Rob Walling:
So thanks for that question, KP. Next question comes from Mark Gadala Maria, and he asks, “At what point would you think it’s time to give up on a SaaS idea and move on?” You and I have both each killed SaaS ideas. We’ve started things that we didn’t see through. We’ve started things that we did see through. So why don’t you weigh in first with your criteria of when it is you throw in the towel?
Derrick Reimer:
Yeah. I mean, it’s a hard question because it’s so dependent on so many factors. Part of it is, how much energy do you have for something to keep working on it? Are you a Matt Wensing type where you’re kind of relentless and you keep pivoting and working off the same core but trying to find the right market? I have a lot of respect for entrepreneurs who have the grit to do that and the resources and the capability and all that, but these days, I try to think about the reasons why I would bail on an idea. So if there’s not enough demand or people just don’t seem to be problem aware or if I find there’s not really willingness to pay or maybe there’s some huge platform risk things or external factors like that or I can’t seem to find viable distribution channels, these are all reasons that would cause me to really pause and reevaluate.
So I kind of think then in reverse like, “How can I get confidence that these things aren’t true as early as possible?” So generally, if the answer is I don’t know, then I would try to think through how to get an answer to those. You’re not going to know with 100% certainty in most cases. You can’t talk to the entire market unless you have a market of three people or something, but try to gain some degree of confidence on knowing that there actually is demand and that people are aware of the problem and they’re searching for it and they’re willing to pay and all those things.
Rob Walling:
What you’re saying is that could be summarized as validation. You could say, “Oh, we bucket that all into validation.” I hear some people say, “Oh, yeah, validation doesn’t work,” or, “Oh, validation doesn’t work the way it used to,” or, “I don’t believe in validation,” or whatever. It’s like it does exist. It’s a thing. It’s not 100%, but what you’re saying is it’s learning, it’s research, it’s conversations. It’s like if I came up with a brand new idea and I told it to you and five other people, I would at least get some feedback, positive or negative, and then I would want to dig in and, as you said, look at search query, volley.
There’s a bunch of stuff. We don’t have to go into what validation is, but I still today believe there’s no formula for validation. There’s no like, “Oh, do this,” and then you’re 20%, and then if you get 10 yeses, then you’re 50. It’s like there’s no exact number, but there’s this directional correctness in this founder gut. It’s incomplete information, and that’s you have to make a hard decision is, “Do I keep going?” but I’m totally on board with that.
Derrick Reimer:
So with Level, which I think a lot of folks probably have heard me talk about this, wrote a blog post about it back in 2018 when I shut down that startup attempt, and that one I found contrary to what I expected or I just didn’t anticipate this, that the people who were most excited about it and were giving me all the positive signals were sort of downstream users of the product, and they weren’t the actual people responsible for buying it. So a lot of makers in an organization really disliked Slack and wanted something that was calmer, but the people who were charged with buying it were more of in the manager tier of the company, and they loved it. They loved the ability to ping an engineer anytime and get an answer quickly.
So there was a disconnect on recognizing the actual core problem that I was trying to solve, and it was going to require more of a cultural shift for a lot of the people that I thought would be good customers for their organizations to actually buy into the premise was a whole different animal. To me, it just deemed too difficult, too risky. I’ve since watched others try to run a similar playbook and grow really, really slowly because there’s just so much headwind there. So that was just one anecdote from my experience.
Rob Walling:
Look, it could be a matter of if you’d raised half a million dollars and spent years more working on it, maybe eventually it would work. You have to make the calculus at some point. You don’t know. The timing, I think of Slack being unseated, is probably coming. I think more and more people I’m hearing really don’t like it. I don’t know if that’s still a real thing though. If you built Level today, would you get any more at traction? I don’t know. You got to make the decision and move on.
I say a lot that funded companies go out of business or fail when they run out of money, and bootstrap companies fail when the founder runs out of motivation. So that’s usually how I think about it is when I’m … To summarize it colloquially, it’s like when I run out of ideas, when I have no more ideas or no motivation to keep going, and when I say, I mean I would come to you, I would go to Ruben, I would go to Einar, I’d go to all Craig Hewitt, I’d go to all the smart people I know if today I was trying to grow something and it wasn’t growing, and I’d say, “Here’s the situation. What’s your thinking? What should I try?” Someone might be like, “Oh, you know what? I saw this other product do this thing,” and if you had an API layer, whatever, there might be ideas.
As long as there were ideas on the table that I thought were viable much like back in the days of DripWord, it’s like, “We’re not growing, man. We are plateaued,” but ideas kept coming in of like, “Ooh, you could build automations. Oh, you could build a shopping cart, you could build affiliate management.” There’s all these ideas and we just had to figure out which one or ones do you pick. So I think that’s probably my thing.
Now, the hard part is if you’re young or you’re new to all of this, you don’t have many ideas. So do you just quit? Do you just launch and then quit because you have no ideas? No, I think you get better at coming up with ideas. You learn from folks that are ahead of you. You learn from this podcast and the guests on this podcast like yourself, and you read the books in our space. There’s a lot of them, whatever it is, podcasts, there’s YouTube, however you’re going to learn about this so that you start to get a sense of, “What would Derrick Reimer do in this situation? How could I channel Derrick Reimer?” Maybe I train an AI bot on all of your podcast episodes and try to talk to it. I know a bunch of people that have done that with Startups for the Rest of Us.
I actually think that’s an interesting idea of just come up with thoughts and ideas and then figure out, “Are these viable do and do I want to do them?” because at a certain point, you have viable ideas in front of you and you’re like, “I’m so (beep) tired of working on this. I just don’t have the motivation,” and at that point, you get to then take a beat because you don’t want to make an impulsive decision and shut it down overnight, but you get to take a beat and whether a beat is a day, a week, a month and take a breath and say, “Am I getting used to the idea of not working on this anymore?” and kind of let that sink in. So that’s probably my … I feel like I read a whole book chapter on this, but that’s as about as succinct as I can get it to when I give up on something or shut down an effort.
Derrick Reimer:
I’m seeing more and more people kind of pulling the line of nobody really knows what they’re doing, this is all kind of luck anyways, so you just launch a bunch of stuff, right?
Rob Walling:
It kills me. Absolutely.
Derrick Reimer:
I guess that is a way you could do it. So you could start something and then not really pursue a bunch of ideas on how to actually grow it and then just kind of let it sit and wait and see if something hits randomly, but I think the whole-
Rob Walling:
The roulette, the roulette approach, the lottery ticket approach to building a bootstrap startup, right?
Derrick Reimer:
Right, and I think there always is a certain amount of timing and luck that has to get woven in as you’re systematically trying to get traction for something like we’re not 100% responsible for all of our traction. There’s always going to be a little bit of the timing, and honestly, hopefully it correlates with you identifying a problem that maybe the market needs. So you intuited that there was an opportunity here, which increases your odds of getting lucky, I guess, with the timing.
I would say for me, I’ve always been of the mind that if I’m going to work on something, I want to really focus on it and give it the best shot at succeeding, and if that’s not happening, I think it’s really hard to set a SaaS on the side and just wait for it to take off because SaaSes are not really, you can’t autopilot a SaaS. I haven’t really seen it happen with much success.
So for me, it just is not worth the effort of trying to keep something running on the back burner, but not really investing effort into it. So if I was up against that, do I put this on the side and wait for it to magically start growing or do I just throw my effort behind something else, I would be more apt to just throw my effort behind something else.
Rob Walling:
Yeah, I think that’s a good summary of it. This is always hard, especially when it’s a gut feel and you’re going to have to ask yourself questions, and it’s different for different people, but I think knowing yourself is another part of it of, “Do I give up on things too early? Do I not push on them? Then I should probably stick with this for longer, but am I the person that stays with the same idea for six years when it still has four customers?” Well, then you should probably not do that again. There’s also that kind of personality factor. So appreciate the question.
Next question comes from Kartik Manjunath, and he asks, “How do you find customers in a crowded market when SavvyCal is competing against the likes of Calendly?” That’s not only a crowded market, but it’s like there is a 900-pound gorilla as well. Not all crowded markets have a 900-pound gorilla, and not all 900-pound gorilla markets are crowded. Sometimes there’s one big player and there aren’t too much competition, but you are in one of those spaces that has both. So how does one get customers, Mr. Reimer?
Derrick Reimer:
As I was thinking about this question, I was trying to figure out if it’s really much different in a “crowded market” than a not crowded market because, I mean, fundamentally, it’s the same. You got to show up in front of prospects who have some purchase intent, some demand, and then you have to present them with positioning and a message that resonates with what they care about. So when I think about how SavvyCal, how we position ourselves against Calendly, I mean, obviously, it would be very tough to just copy their H1 and lead with the exact same messaging. That’s a recipe for failure right there.
So I think it’s figuring out how to really authentically identify some traits or some qualities about what you’re offering that is meaningfully different. Then I think it’s a lot of blocking and tackling on trying to run the playbooks so that you do show up in the places where people are looking for things. So that’s trying to get listed in the Listicles, where if someone searches scheduling software and they see a bunch of articles that are showing top 10 lists, can you get in those articles? Can you get in the Zapier blog when they’re talking about automating scheduling? There’s a bunch of these things that take time and effort and varying degrees of success, but basically trying to get in the conversation as much as possible is how I think about it.
I think for SavvyCal too, there are some things that are to our advantage like the inherent virality of the product is a helpful dynamic for SavvyCal, and it’s not necessarily there for other products. So every time someone uses it, they’re exposing our brand to the person on the other side, which I think is a pretty big lever. It’s admittedly pretty difficult for us to measure because I think a lot of times there’s kind of initial touch and then maybe they book multiple times and it gets them thinking, and then whenever they’re ready to purchase scheduling tool, now SavvyCal is sort of in their mind because they’ve already been on the other side of it.
So it’s kind of hard to track through the whole chain of touchpoints to attribute to virality, but I definitely know in qualitatively asking customers when they sign up, “How did you hear about us?” a lot of people talk about, “I used such-and-such as link.” So there’s things like that that just help drive that exposure, but, yeah, I mean, crowded markets, it is tough. Like If I search scheduling software in Google, I mean, there’s hundreds and hundreds and hundreds of tools. So you can’t just rely on those head keywords and trying to rank them. You got to get a little craftier, I guess.
Rob Walling:
When I think about it super simply, if someone were to say one sentence how do you do it because it’s way more than a sentence, but one sentence, I piggyback on what you said, which is you have to figure out how to be differentiated and/or you want to find what I’ll call proprietary or owned traffic channels. I can’t figure out the exact word for this, but I think of Rubin with Seinwell, where dude is really good at SEO like to an extreme. If you enter any space and you can rank for those head terms, you can get a lot of traffic. Rubin also differentiated Seinwell, like he has features that all his competitors don’t.
One or the other though can get you customers. You could actually have kind of a clone of the big player. If you had massive, let’s say you got 50,000, 100,000 uniques a month and you were top three in Google, you would grow, not as fast as if you were also differentiated. That’s why I said and and or. I try to do both, but you can’t always do both.
To quote from page 51 of the SaaS Playbook, “How can I compete in a competitive market? A mature competitive market can be a total bloodbath, but it can also be a fantastic place to grow your business once you get a foothold.” Then I go through. Here are different ways to get a foothold. So one, compete on price, and I say competing on price is tricky, but you can get traction if you offer more than 80% of the product for half the cost. You get it. It’s not exact numbers, but it’s there. I go through five paragraphs of that, compete on sales model.
So oftentimes, incumbents in competitive markets have high touch sales process where customers may schedule a demo and mandatory setup fees, and it’s just a big pain in the ass. I don’t put that in the book, but I’m ad libing here. So you can go in and do a self server, a lower server, a one call closer or whatever. Compete on product, that’s a little bit what you and I are talking about or trying to differentiate.
Now, later in the book I talk about features are temporary moats because people replicate your features, which I think you’ve experienced to a large extent. Then I have how to market against large competitors, how much should I worry about them. I talk about building moats and different types.
Anyways, there’s enough content. I’m not trying to plug the book, but there’s a reason I put that in there because it is really important. This is not a 10-minute podcast answer. This is a big answer of it’s a lot of things to compete in a competitive market, but if you can do it, it’s a superpower because competitive markets usually are large and that’s why they have competition, and so you can grow faster. Usually, I would say competitive markets are often growing quickly. That’s why everyone’s launching in them. So thanks for that question.
Next question is from Aboma Kelly, and they ask, “Question for Derrick. Do you have any plans or desire to start podcasting again on a regular basis or are you officially retired?”
Derrick Reimer:
Officially retired.
Rob Walling:
That is like that, huh? Do you want to tell them our little secret of how we specifically had this conversation?
Derrick Reimer:
Yeah. We talked about this over cocktails a couple months ago, I think. I’m really enjoying doing episodes just like this one on this podcast. So for those who don’t know, I used to do one of those kind of check-in on what you’re working on every week type of podcast. It was called The Art of Product. Me and Ben Orenstein from Tuple did that for, gosh, five, six years. It was both a lot of fun, helped me build a small audience and a little community, but also, it was a ton of work. It was taxing on me. I think for Ben, it was an easier thing. So I think it kind of depends on your personality, but for me, it was like I always felt this pressure to have something smart to say and summarize, well, my learnings from the last week, and I just found it was kind of ended up being a little bit of an energy drain.
So I think while I hear from a lot of folks that they miss The Art of Product and they really enjoyed the content, in that regard, I wish I had the energy and the ability to keep that cadence going, but I don’t know, I think I’m done with that sort of podcasting, but I really love showing up here and answering listener questions and just talking about stuff.
Rob Walling:
Yeah, and that was, as you said, we were having cocktails and I said, “Well, do you just want to come on every, I don’t know, six, eight weeks to the show, just I leave it as a standing invite, you ping me whenever, it’s not a recurring calendar invite, but just come on quite a bit as a guest?” and you were like, “Yeah, why not? Let’s try it.” So we haven’t told anybody until now, but that’s the idea of getting you back on the show, and they’re so easy. These are easy recordings. We always have topics. Even if I hadn’t tweeted today, we would fill 35 40 minutes of good content.
So I think of it less as retiring and more of moving to that next stage, that next phase like when someone has a big exit, they often become, what, an investor or some other thing, and you are like, “You know what? I had a big exit from Art of Product and now I’m investing in the rest of the community.” The braid metaphor broke down around there.
Anyways, thanks a lot for that question. Hope it was helpful. TinySeed’s own Einar Vollset asks, “How did it feel to get an open source competitor entering the market with $40 million in funding and that would have developers work for free to rip off,” his words, “rip off every innovative feature that you added?”
Derrick Reimer:
Oh, Einar, good question.
Rob Walling:
I love the wording of it. It’s like I feel great. It feels amazing.
Derrick Reimer:
By the way, those are Einar’s words, not mine. Yeah, no, but honestly, on this topic, I guess in general, I would say these kinds of things like having competitors that are quite active in the market and obviously looking around at the stuff that other people are building, and that includes us as a participant in the market, it really does help you to more quickly understand what your actual differentiators are. I think you point this out in the SaaS Playbook about how features are not moats because there’s not really intellectual property protection in that way for what we’re doing in the software space. Anyone can look at an interface and say, “I like that. Let’s build that.” There’s no recourse. There’s nothing proprietary, so to speak, in that.
So I think when you’re seeing some of your key interfaces showing up in other places, it’s disheartening at first, but also, it just makes you realize, “Ultimately, I can make my business stronger by not trying to rely so much on things that are ultimately not defensible.” So I think that’s what we’ve been, with this latest brand refresh that we did, we’re trying to really sharpen our positioning a bit to really speak to the people who come across us in the market as they’re searching around for tools like, “Why do they choose us? Why do they like SavvyCal?”
We had a lot of conversations with people about this and mined through different survey data that we’ve run over the years and just workshopped it a bit and tried to get a sense for this. I think it’s like people like SavvyCal because we’re small and nimble, because they trust us to listen to customers. We started out in response to Calendly not really changing much over the years, and there were many, many forums where people were asking for stuff and they just sort of felt like they weren’t being listened to.
So we showed up as like, “Hey, we’re a scrappy upstart looking to talk to customers and figure out how to build the best tool possible. We’re going to sweat the details.” So these are all things that we’re trying to call out. I think a company that’s riding on a huge batch of venture capital and trying to grow as quickly as possible probably doesn’t care about the same details.
So I think we can call out some of that stuff. It’s a little fuzzier than saying, “We have this feature and they don’t have this feature,” but ultimately, features are all, I don’t know, yeah, it’s not super defensible. So I guess that’s how we think about it, and ultimately, I think it does help us be a stronger company.
Rob Walling:
All right. We have four more questions to get through. Two are from Greg Deneo. His first question is, “How is Derrick’s redesign working out, the SavvyCal redesign?” So for folks who don’t know, you redesigned the home page inside the app as well. It’s a pretty significant one, right?
Derrick Reimer:
Yeah, not much in the app, although we did at the same time release a refreshed link editor, the core-
Rob Walling:
That’s what it was.
Derrick Reimer:
Yeah, the core editing interface in the app with a bunch of UX improvements and a refreshed marketing site, refreshed logo. It’s been really well-received.
Rob Walling:
Did you change your H1 as well?
Derrick Reimer:
Yup. H1 changed a bit.
Rob Walling:
You changed some copy?
Derrick Reimer:
Yeah. Most of the copy on the home page is different. Added a features page, so one place to kind of summarize key features, and then we’re gradually porting over the other pages to match the design aesthetic, but, yeah, it’s been really well received. I mean, people have recognized the effort that we put into it to try to … We didn’t want it to feel like your typical startup, safe, corporate startup, blue and white landing page. We wanted it to feel organic, and we wanted the design to communicate similar values that we were saying in our words. I feel like we nailed it. I think, yeah, it’s been well-received. We’ve had our best sales month this last month that we’ve had in a long time, so yeah.
Rob Walling:
Do you attribute that at least partially to the new look?
Derrick Reimer:
I mean, I think we made a lot of noise when launching the brand refresh and sent some emails to the list. So it’s hard to say that it’s attributable directly to the refresh design, but it was nice to have an excuse to go out and ship a bunch of stuff. We shipped that group scheduling feature and the refresh link editor and the brand refresh. So hopefully that that’s just another indicator that there’s energy and momentum behind the company, which I think helps with marketing effort.
Rob Walling:
Neat, and I mean even the home page. So I don’t see the home page because when I go to savvycal.com, I’m logged in, so I never … I know I can log out.
Derrick Reimer:
Oh, yeah, you can go to slash home.
Rob Walling:
Yeah, and I went incognito to look at it now, but just as a rule, when I go to SavvyCal, I never see the home page because it has me logged in, but I did see you announced it on Twitter and then I checked it out. I mean, the green, the fonts, the kerning, all the things that you care the most about, I mean, it looks great. It looks really, really solid. So yeah, I think you should be happy with it.
Greg’s other question is, “Was there ever a consideration for launching SavvyCal as a vertical SaaS?” I will actually add to this, launching or narrowing focus at any time. He says, “For example, a calendar scheduling link for salespeople, for lawyers, for insert any customer segment that you enjoy working with.”
Derrick Reimer:
Yup, that’s a good question. So I mean, initially, the thinking was to be horizontally positioned and pick up on signals on who’s getting the most value out of this and potentially refined positioning or narrow things a bit. To date, I mean, we have a very diverse set of customers, which is both good and bad. It’s good in that we’re hitting the mark on being a general purpose tool for a lot of different people, but the challenge is we have to try to identify the commonalities between them and figure out like, “Should we go after one specific set or should we keep speaking to the same messaging that resonated with this diverse set of customers?”
I think we’ve experimented with things here and there, but haven’t gone as far as fully updating the H1 on the home page to speak to a specific vertical. I mean, I think in order to do that, I would want to have a strong enough hypothesis that basically, that I’d be willing to exclude some of the people that maybe otherwise would’ve signed up like if they saw that this is for sales teams on the H1, someone who’s not doing sales probably would choose not to sign up versus if we did.
So I see that as the more mature the business gets, the riskier it feels to make that kind of shift, but I think in smaller ways, we experimented with like for a couple of months we’ll spend some time building features for sales teams and we’ll work on some things, some efforts to try to see, gauge how it’s resonating aside from fully shifting the positioning on the homepage, if that makes sense.
Rob Walling:
You have to be pretty certain of that to make such a strategic shift, I think. So it’s one of those I would need to sit with for a very long time. I mean, I can bring up a bunch of examples, it doesn’t really matter, but any big strategic shift like that, I need probably months of mulling it over and saying it out loud internally and saying, “I think this is where we need to go. What do you think?” and then I sleep on it for a week and then I come back to it and I try it on again. It’s one of those things of like, “Does this really feel right?” Oftentimes, I can’t remember. It’s been very few times where I’ve made a decision of that magnitude quickly and without some pretty strong … I need some strong conviction that it’s the right call. Sometimes if you don’t have that, it’s tough. It’s tough to think about doing it.
Derrick Reimer:
The hypothesis around that niche down needs to be as strong or stronger than the one that’s currently working for the business. It has to overcome that, I think for me.
Rob Walling:
Yup, and I think there’s also has to be a bit of excitement, your internal excitement of like, “Oh, I’m really excited to work on this and I really want to dive deep into this.” So thanks for those questions, Greg.
Last two questions from Chris Livdahl. He asks, “How did you land on the idea for SavvyCal among others that you decided to pursue, and did you validate the idea before launching it, and if so, how did you validate it?”
Derrick Reimer:
So I made couple of bullet points here. I’m trying to capture what my initial thinking was because it’s funny how it does shift over time, but I could think back to what was I thinking back in 2020 when I was just starting to pursue this. So the thinking was Calendly doesn’t seem to be innovating much these days. They’ve been kind of the household name, so to speak, for this type of product, but the product hasn’t really shifted that much and it doesn’t seem like they’re really listening to customers that closely. For me, it was big that it would be a relatively quick to get an MVP to market, to build a basic scheduling functionality. So I felt confident that I could start to test this with an actual product in hand pretty quickly.
It’s a product that has the virality built in, so that was a big selling point for me too. A lot of my existing audience uses scheduling tools. I think about this as this is like kindling for the fire. I can’t rely on personal audience to sustain the entire business, but it’s enough to get maybe a kernel of customers that are really excited about it and willing to start using it and spreading the SavvyCal name and talking about it to their friends and helping get the wheels moving on this thing. So that was an important thing for me. Since I had a small existing audience, I wanted to leverage that.
Then there was this hook that I picked up on. It was the power dynamic issue. So I feel like every other week there was a Twitter thread where someone was opining that Calendly is rude and it’s not good professional form to send a Calendly link to somebody because of the power dynamic issues. You’re forcing me to do work to get on your calendar sort of thing. It was an interesting like it’s both a people problem and I think a technology problem. I think the tech can help it feel a bit more collaborative so it doesn’t feel as off-putting to receive, but it’s also like, are you exhibiting good etiquette? This was enough of a hook where it’s like, “Well, what if we could build a tool that doesn’t feel so awkward, that feels more collaborative, feels more personal?” and that was the initial hook.
So I think we wrote a little manifesto talking about the power dynamic and how we’re going to fix it. We had this visual booking interface and personalization and a bunch of other little details that were going to make this better, and put that on a landing page and started to gather email addresses and have conversations with potential customers and engage interest. I think that was the extent of the validation, and then I got down to work building an MVP, and within a couple of months was able to start testing it out with real users.
Rob Walling:
To take you back even further, I believe you started even considering … You had a list of software that Calendly was on, and that list came from what did we pay for at Drip, what was all the software we paid for, right? There was GitHub and Slack and Calendly. You can imagine what the stack was. You came over, we sat in my front room and we’re talking through like, “Which of these can be disrupted.” You’d already tried to disrupt Slack with Level and that hadn’t panned out, but we were looking at, “Are you going to compete with GitHub? Not directly, but is there a thing there? Is there, whatever?” We went down the list and marked off like, “Oh, these are bootstrappable or mostly bootstrappable businesses.” Then we said, “Which of these has an in?” because that’s the other thing. It’s like, again, Stripe, probably not a bootstrappable competitor business, but there were some, I don’t remember what they were, but it was like, “Oh, there’s this product, but people love that product,” and there’s no wedge, there’s no differentiation, there’s no angle, there are no people complaining about it or whatever. That was what we determined.
Calendly was one of a couple, I don’t remember what they were, but there were two or three where it was like, “Ooh, any of these you could probably do.” You then talked to me and I said, “Look, I would pay for a Calendly alternative that did X, Y, Z.” I think at the time it was like that integrated with my podcast recording suite, whether that’s Squadcast or Riverside or whatever, but it integrates and automatically creates a room, and it’s like, “I don’t think Calendly is going to build that.” Then you talked to other people. I think you talked to Wensing. You probably talked to Peter. You talked to Einar, and you talked to all these people and said, “What don’t you like about this?” and you were trying to get that of like, “How do I be different?” because again we said, “You could have just gone and replicated Calendly. You’re a good builder. You could have done it. It’d been elegant,” and all that stuff, but that doesn’t get you there.
So yeah, I just wanted to take people back even further because by the time, you had already gone through a process just to narrow down to what space, what category. Notice you didn’t start with a technology and say, “What can this do?” You didn’t start with, “What new novel thing that has no category can I build?” You were like, “I really want to enter an existing category.” Everything on that list was super competitive. There are a bunch of tools and there’s a big leader in almost all of them.
I’ve actually quoted that process. I have this book that I will publish it eventually, it’s probably going to be next year. It’s called the SaaS Launchpad. It’s a precursor to the SaaS Playbook, and it’s about coming up with ideas, trying to validate, pre-validate, launching, building a launch, just all the early stuff that comes before that. It’s a hard book to write because it’s so squishy. You can hear us, even you and I, experienced entrepreneurs done it multiple times. It’s still a very squishy process. So to actually put it in writing is like you need a lot of, “Well, this, it depends, this and that,” but one of the chapters is about coming up with ideas like this.
I have seven different approaches, and one of them is make a list of all the things that your company pays for an hour that you pay for an hour. I totally got this from you doing it. Others are like, “Hey, take a vertical SaaS and go horizontal or a horizontal SaaS and go vertical,” or you have a bad customer experience and you can improve, blah, blah, blah. You can imagine the list of those seven kind of … They’re not frameworks on themselves, kind of a single framework, but I think this is a super interesting way to ideate.
Then the thing is is how do you get to that next step. How do you not just pick it and say, “Ohm boy, I want to be in that space,” and you don’t take the next step, which is, “Now let’s research. Now let’s find out what the weaknesses are. Now let’s find out what people are unhappy with in this space so that I can at least have some type of wedge or angle or focus that differentiates me from the big incumbent.”
Derrick Reimer:
Yup, and also when I was taking that list and evaluating them against each other, there’s all kinds of criteria I’m looking at, but one of the ones I was careful to do this time around especially was like, “All right. I want to make sure that this has as close a fit to what my ambitions are and the way that I want to work,” because assuming that I don’t have to work on this for the next several years, what’s the founder fit element of it? I hadn’t always necessarily considered that. It was kind of like, “Well, we’ll figure it out. I’m willing to do whatever. Let’s just find a good idea.”
There’s a blog post, somebody who’s written in 2019, and maybe this list would be a little different now if I made the same one, but it was a helpful exercise at the time to write these things down, and part of it was coming off of the level experience. I could tell some of these are a reaction to that because I felt a little burned by some of the things that I experienced through that, but I’ll just read it off real quick.
I have these filters, right? The filters were the market must already exist, so I’m not inventing a category. MVP must must be shippable within a few months. Level took a long time. I spent, I think, nine months on it before I was able to get it in front of anyone, which was way too long. I way over engineered it. The product should not be mission-critical. It should be important, obviously, high value, but not something where if we have five minutes of downtime, we’ve severely impacted someone’s business like processing high volume e-commerce payments or something like that. Making a sale shouldn’t require more than a few decision makers because with Level it was like, “Oh, you have to get buy-in from the entire company.” Yeah, that’s not great. Native apps shouldn’t be a minimum requirement. I wanted to be able to focus on web and maybe a progressive web app or something, but not have to build a mobile app.
I think this is kind of another level thing too. People wanted to be able to access messages across all platforms with native apps and it’s like, “Okay.” Well, that adds a whole ton of development time to get something minimally viable. Then lastly, the market should overlap with my existing audience because I wanted to be able to leverage as much of my unfair advantages or whatever that I had. So I wanted to use my audience as kindling and not just go into a completely foreign space where no one knows me, and those were my filters.
Rob Walling:
Derrick Reimer dropping knowledge bombs as always. It’s great to have you back on the show.
Derrick Reimer:
Great to be back.
Rob Walling:
If folks want to keep up with you on Twitter, you are Derrick Reimer and, of course, if they want to use the best scheduling link on the internet, savvycal.com.
Derrick Reimer:
That’s it.
Rob Walling:
Thanks again to Derrick for coming on the show. Thank you for listening this week and every week. If you’re not following me on Twitter or X, however you refer to it, I am @RobWalling. Let’s connect. This is Rob Walling signing off from episode 718.