SPI 525: How to Build Software That Competes in a Crowded Space with Derrick Reimer from SavvyCal

SPI 525: How to Build Software That Competes in a Crowded Space with Derrick Reimer from SavvyCal

Pat:
How do you begin to compete when there are established players in the space that you're in already? Whether it's software or just content creation, maybe you're creating information products, it doesn't really matter physical, digital, there are likely some people who have already started creating an audience in that space or making a name for themselves.

Today we're talking with Derrick Reimer, who created a competing tool to a very popular software called Calendly. His tool is called SavvyCal, so S-A-V-V-Y-C-A-L, and it's actually an ingenious tool that yes, it does a lot of the same things that Calendly does, both of these things allow you to make it easier to schedule meetings and things. So, especially helpful if you're recording podcast interviews or setting meetings or anything like that. But today I wanted to discuss with Derrick, with regards to, how do you get into and actually create something better than something that's already established and exists in this space? You're going to learn a lot because I learned a lot, and I hope that you can take this information and apply it to the space and market and niche that you're in. So sit back, because this is going to be a great one. Cue the intro, here we go.

Announcer:
Welcome to the Smart Passive Income Podcast, where it's all about working hard now so you can sit back and reap the benefits later. Now your host, he has a signed Dr. Emmett Brown Funko Pop by none other than Christopher Lloyd himself: Pat Flynn.

Pat:
What's up, everybody? Pat Flynn here, and welcome to session 525 of the Smart Passive Income podcast. My name's Pat Flynn, here to help you make more money, save more time, and help more people too. Today we're talking about competition and how to create something that's better.

I heard a phrase once, I think it was Sally Hogshead who once said, "Different is better than better." When I first heard that, I didn't really understand what that meant, but what I really understood was that creating something that's different, not just doing the same things, just more of them. Oftentimes we think of better as more, and that's definitely not the case, especially in this day and age, but better can mean different. A different approach, a different way of becoming more efficient or optimizing something.

We talk about these kinds of things with Derrick today, a very smart engineer and designer, somebody who, yes, we're talking about software today, but who can help all of us no matter what space we are in, as we are building our businesses and going through this entrepreneurial journey together. So, let's not wait anymore. Here he is, Derrick Reimer from SavvyCal.

Derrick, welcome to the Smart Passive Income Podcast. Thanks for chatting with us today.

Derrick Reimer:
Yeah, thanks so much for having me.

Pat:
I'm excited because the topic that we're going to talk about today, time, is something that of course, we all have. We all have the same amount of it every single day, but it definitely doesn't feel like that. There are strategies obviously and tools and things that we'll get into, but I just wanted to get your thoughts and perhaps even the origin story of SavvyCal and time and how little of it it seems we have. What are your thoughts on time in general? I know you have some very specific thoughts about that.

Derrick:
Yeah, so to start with my little bit of my back story that led me to this. I've always been a maker, I would say, falling into that category. So from a young age I was toying around with software and building little products and tools and things. Discovered through my growing-up journey and in just discovering where my passion lies, that I love creating things. I'm also naturally an introverted type personality, so it really aligns well with the maker pattern of getting into deep flow and getting inside my own mind and exploring ideas and creativity. So time management throughout my whole entire career journey has been something I've been always thinking about obviously.

So SavvyCal, to tie that in, is a scheduling tool and it helps people find times to meet with other people. One of the things that I encountered, I've been a customer of these types of tools for a long time, and from time to time I use them for scheduling calls with customers or talking to other colleagues. I always experienced this innate sense of dread anytime I was going to send out a scheduling link to somebody because I knew, I intentionally tried to keep my calendar as open as possible. Sometimes all it takes it one thing placed at the wrong spot to break up the entire flow of a day and ruin my productivity for that day. That was one piece that really made scheduling time difficult with people when I was attempting to wear both hats of like, someone who needs to interface with the public and with customers, and obviously that's a super important part of doing business, but also someone who is responsible for being the creative force behind a product and continuing to develop it, and investing the uninterrupted time that goes into that.

I became a student of Cal Newport's book Deep Work, and that was a big influence on me and got me really interested as I continued to think about this, on how to cultivate productivity at work.

Pat:
Yeah, I mean as a business owner, there are a number of things that we have to juggle just within the work that we're doing, but at the same time it's so important to also connect with other people, which can be difficult to do. I am an introvert as well, so that even of itself is a little bit of a hurdle, but then comes to logistical and administrative part of that which is often if we think about how that used to be done, it was just all done via email. It would be like 50 back and forth passes until we finally align on something, and then something changes and we didn't find out and somebody's showing up when they weren't supposed to or something got canceled and the other person didn't know about it. This is why these kinds of tools exist, to help manage those processes, but even then it still felt a little bit clunky or not without personality.

This is where SavvyCal comes in to solve a lot of those problems. So, what are the big problems that SavvyCal helps create solutions for?

Derrick:
There's a couple problems that we identified early on around the scheduling flow. One of the big, big things that I discovered is that people are inherently averse to receiving a scheduling link. Anytime I see something where there's people who react negatively to something that should be a really positive thing, or choosing more efficient route to achieve an end goal of finding a time to meet, and yet there's so much visceral disdain for this interaction.

Then talking to colleagues of mine, I mean there are certain industries, I think it's pretty common in the investor community, when you're talking to venture capitalists or angel investors and that whole realm of needing to book times with each other. There's this broad aversion to using scheduling links of any kind, and I think a lot of that comes down to this interesting power dynamic that arises when sharing it. So part of that is an etiquette problem: if I'm wanting to meet with you and you have no idea who I am, it's going to be faux pas if I just cold email you and say, "Hey, find some time on my calendar." There's an implied, “I'm asking for a favor but I'm asking you to do some work in order to negotiate this time with me.” So part of it is just a human communication issue where there are certain situations where you have to put forth this posture of, “I'm willing to coordinate this however you want to coordinate it.”

I still was interested to see if we could explore building a product that still made it okay for someone, even if there's an unequal dynamic, for someone to share a link and open up the possibility for someone to, for it to get used in an exchange like this. So there's a number of different ways that we're trying to innovate around this. A big piece is trying to make the experience just as convenient for the other person. So traditional scheduling links you would often see a calendar view and you click on a day and then you see a list of times, and if you're a busy person, well, suddenly you have to click back to your calendar and go and try to reconcile what's on your calendar with what the other person is presenting in this minimal scheduling interface. So we started to think about, how can we make this more collaborative? How can we make this so that when you receive a scheduling link it's actually a delightful experience, and you can really quickly see when you're available, when you're not, right on top of the other person's availability. So that's just one product—way we are attempting to solve this problem with product.

Pat:
I really like that because before, you'd have to really explain yourself, or else you're going to come across a little bit more from a power perspective, like you said, and I've felt that before. Somebody who was wanting to interview me said, "Yeah, I'd love to interview you." They said, "Okay, well, I'm only available at these times, so you got to make it work. Can you please change around your stuff to make it fit into my stuff?" Although the end result's going to be the same through something like SavvyCal, like you said, it's the approach and the dynamics of what happens after that click that actually turns it into, like you said, a great experience. I love how you were thinking about that.

Before we talk more about SavvyCal and some of its features and how it can help us, your perspective from a maker and a problem solver. What's your process for that? There's a lot of people like that who are listening right now, and here you are, a scheduling company, a software, going into a space that's pretty populated. A lot of people have their own specific ways of doing things; this could be a very big ask to get somebody to change. What's your approach to solving problems when it comes to just making things and creating?

Derrick:
I am a big proponent of sharing my work publicly. So I've been podcasting for a while, so I have that as a, it's just me and another software founder hopping on the mic and talking through problems in a public forum, with the hope of other people being able to glean insights. We're not really providing advice on the podcast; it's more talking around just things that we're working on what insights we discovered in that week. But that also serves as a forum of getting the word out about the types of problems that we're each solving through our respective businesses. There's that piece.

Then my corner of Twitter has been a fantastic place for community. I know not everyone has the same experience, and there's a bunch of different voices on Twitter that can be sometimes difficult to consume all the time, but I've been fortunate to find a nice, healthy little corner of really supportive indie makers and other bootstrappers and people who are working on interesting things. I mean, that was honestly one of the criteria that I looked for when I was deciding what to build next was, what is a tool that is in a big market already?

I knew I wanted to play in a big market because that just means there's so many different opportunities to explore and work on positioning and find that pocket of true believers who were really going to love the product. So I was set on that, but also wanted to build something that appealed to the people who were already in my tribe already, people who were already invested in what I've been working on and what I've been building and over the last 10 years as an entrepreneur. Those are the people who are most likely to give it a shot and try something, take a shot on something new, because like you said, there's, I'm playing in a very mature space. There's a lot of well-established tools. Admittedly when I started working on SavvyCal, it was met with a healthy degree of skepticism, like, “Are you sure there's really room for something else, or is this basically a solved problem?” I think even some of my biggest supporters, people who were really wanting to see me succeed, maintained a healthy degree of skepticism themselves and they weren't really sure.

So I had to rely on a bit of my own vision and take a little bit of a leap to say, “I think I can improve on the status quo.” Honestly, the whole time I've viewed it as starting something new like this, you're starting a campfire and you need that kindling, you need something to ignite the movement that you're trying to start. For me, a lot of that has come from my community of people who are listening to my weekly updates or just following me on Twitter, and continuing to show momentum. So I've always aspired to build this as a product-led company. One of the ways that I'm trying to do that is letting the product speak for itself. So sharing a ton of work-in-progress things to give people a window into how the product is shaping; that's also an opportunity for people to chime in and let me know if they're excited about something or if they want to see something slightly different from what I'm working on. That's a really nice, valuable input into the product development process too. But I think that being very open and sharing the sausage-making part of the business helps people to feel that momentum, and that's addictive for people and it's contagious, I think.

Pat:
Yeah, I mean, people feel invested once they see how something was and knowing that you want to make changes. People want to see what it's like on the other side of that, so the before and after is always an interesting picture.

How did you, when you started this idea for SavvyCal or at least even playing around in this area, how did you validate your idea? What were the first steps you did to make sure that this was something that you knew was the right direction to go?

Derrick:
I started with a couple of... starting conversations with people who I felt like I knew well so I could engage them easily in a conversation, just send them a message, but people who I felt like were good candidates to be potential customers.

One resource that I like to recommend to everybody on having these kinds of conversations is a book called The Mom Test, by Rob Fitzpatrick. It's a very quick read, it's super actionable. He basically teaches you how to talk to people in a way and ask questions that doesn't taint the well, that doesn't give you biased feedback, because the book is named so that you could even validate a product idea with your own mom who is most likely to lie to you because she wants you to succeed and she wants to say, "Oh yeah, that sounds like a great idea." I think anytime we're talking about our ideas to people, we're always vulnerable to people basically not intentionally lying but just telling you, “I'm trying to tell you something to make you feel good,” when really they're giving you a false signal. This was a super valuable resource.

I learned it the hard way through my journey over the last couple of years working on a different product and discovering at the end of a 13-month build-out period that in reality the market wasn't actually ready to buy the product that so many people had told me that they wanted initially. So that was big, starting some conversations with people who I already knew.

I will say actually that this is not a completely foolproof activity. Even I would say of the first 10 conversations I had of this kind, trying to ask questions around how people are solving this problem. What areas that they're dissatisfied about, and if they're dissatisfied about something, have they searched for an alternative solution? Questions like that, it was mixed. I think a lot of people were very pleased with existing tools and hadn't really thought too deeply about some of the problems that I had thought more deeply about. So there was a little bit of skepticism, as soon as I could show an MVP version of the product, minimal viable product that I could put in the hands of users, I think is when it really clicked for people.

I would say that I did the typical, have these conversations to try to validate as best as I could, but in my experience this time around, I definitely had to rely on my own intuition a bit, and that meant my goal was to get this initial version of the product out the door really, really fast, as fast as I could so that I wasn't wasting too much time if it turns out it was not going to be a good idea, so that I could give it an opportunity for it to really click with people. When they first put their hands on the product, they could say, "Oh okay, I get it now. I see what you're trying to do here."

Pat:
The idea of an MVP is so important, and I like to call that your prototype, and you eventually created a prototype to share and actually get real feedback. And it's cool because like you said, it aligns perfectly with, well, let's have the product sell itself. Product led, and I love that. How do you create an MVP? It can be very difficult, especially in the software space where maybe through these conversations you're getting people who are like, "I want this, and now I want this," and you get feature creep and you can have this thing that looks like the remote for your television where you literally only use two buttons but it has 50 buttons on it. How do you define the scope for what makes a good MVP that's going to prove your concept and hopefully something that you can move forward with?

Derrick:
Yeah, it's a tricky one, admittedly. The approach that I took was basically trying to craft initially, what's the core thing I'm trying to solve on this first pass? I honed in on the power dynamic issue. There are other issues around scheduling too that I'm hoping to smooth out, but I decided, you know what? This is the first one, I have my own intuition about this problem, other people have expressed similar pain around this. Then the job became, how do I identify what the key feature around that will look like, and try to invest 90 percent of my effort into presenting an initial version of a solution that speaks directly to that problem?

That meant there were no delete buttons on things in the first UI; there was no billing engine built in. Thankfully, Stripe has some really good tools like payment links now and Stripe checkout, where if you want to charge somebody for something you can hack it together, and then you can wire up your billing engine later on. It was relentlessly focusing on this core job to be done of the product.

In this case it was, I spent a ton of effort on the UI of the scheduling link itself. SavvyCal is different from all the other tools in that it presents similar to a Google Calendar week view when you're looking at availability. It shows grayed out regions where you're not available, and un-grayed out regions where you are available. This was a pretty decent technical lift; it took, I say it took several weeks of really deep work to massage this, working with an existing library to make it work for exactly what I was going for and all those little bells and whistles that it takes to make the interactions feel really smooth. So I made sure to focus as much as possible on that piece, and then other parts of the UI remained extremely simplistic.

Also from these conversations, I got a sense of when people are using existing scheduling tools, what are really the features that you need the most? Most people had honestly three or four features that they were using, and the rest of them were like, “Eh, yeah, maybe I sometimes use that, but it's not that important to make the jump over to something new.”

Pat:
I like that, so understanding what the minimum requirements are, the must-haves. So that obviously gets baked into the MVP in some way, shape, or form, but then you're also perhaps allowing yourself to stand out from all the other options that are out there by picking, and it sounds like you just chose one thing to really focus on that was going to be different. That was the experience, and this thing about power when it comes to sharing these links. So that to me is the perfect formula. Okay, you want an MVP, you don't want it to just be like another product, but you still want it to do what everybody else does with those other products that are required, so let's get the requirements in, let's do the one thing different, and let's do it really, really well.

It sounds similar to when we created a prototype for a physical product. My videographer and I, we invented a tripod that just did one thing really, really well, and that was enough to get started. Now, unlike a physical product, we can't just write code and it changes overnight. We're not at liquid Terminator metal yet, but with a software you can do that. So that's the cool thing about software and even information courses: you can actually make changes on the fly as you go. That's awesome.

Can you walk us through—let's go back to the experience on SavvyCal since we're here now. Walk us through what that's like. So you and I are scheduling something together, let's say you have SavvyCal, I do not. Go through the process, let's talk about what that's like, and we can maybe pinpoint some of the experiences that are actually a little bit different.

Derrick:
So if I'm trying to find a time to meet with you, Pat, and so I'm in my SavvyCal account. I probably have a couple of generic links set up, like typical “Chat with Derrick” or whatever. Maybe that's the appropriate one to use for this type of meeting, but I reach a decision point where it's like, “Okay, I know that we need to talk about planning for this podcast episode.” Maybe I want to make it a little bit more personal, and so I might just click the new button in the UI to just spin up a new link. It's really, really lightweight to do that, or if I know that I have some existing settings dialed in on one of my existing generic links, then I might just hit the duplicate button on that. It takes me right to an interface where I have my little configuration settings. I can tweak the knobs, I can say, “Okay, this will be a 60-minute meeting instead of a 30-minute meeting.”

Then right there to the right, this is a key piece that spoke to my own pain around when I'm about to send out a scheduling link: I'm always nervous that I haven't kept my calendar fully up to date or that I know for sure tomorrow I want to work on this one feature so I would rather not have a call tomorrow; let's make it the next day. So what I want to see right before I click the copy link button is a preview showing exactly what's coming up on my calendar and what availability you're going to see. So that helps me. It gives me peace of mind as someone who's trying to defend my time a bit. It gives me peace of mind on, “All right, this is what Pat's going to see, and I can right there on the fly make modifications.” So I can just drag on the calendar and say I'm going to block out this range of time, and maybe I'm defaulting to afternoons but I know I want to make tomorrow morning available so I can just drag on tomorrow morning and click the allow button. So I can make these little last minute modifications right before sending something out.

Another piece that we baked in at this phase is the ability to have a few preset availability settings. So, say that I prefer to meet in the afternoons because mornings are my deep work time. But I'm willing to meet in the morning if an afternoon doesn't work well for you. We have the ability to say, to give basically ranked availability. It's like, I want to propose afternoons first, but when you're viewing the link, a little popup will show up on the bottom after a few seconds and say if none of these times work well for you, show me some more times.

Pat:
Oh wow, that's cool.

Derrick:
Yeah, it signals to the receiving end that these are my preferred times but I'm giving it an avenue to expand out a bit more. Strikes that balance of, I want to be accommodating but also I want to subtly make my preferences known so that we can hopefully most of the time arrive at a time that works best for both of us.

Pat:
I love that because when you were going through that process, and we'll put links, I mean SavvyCal.com, obviously. You're going to see a demo and there's videos on YouTube and there's all these different places where you can see exactly how this works. So I know we're in a podcast so it's a little bit more difficult to visualize, but it is really innovative. When I'm creating a link to send to somebody, the fact that I could see my calendar right there is so reassuring because my particular schedule is not the same every day. So I actually have to uniquely create an invite link for different people; that allows me to then go, “Okay, well these times on this week are available, so here they are unique, individual,” versus, “Okay, I know that 10:00 AM every day is going to be the same.” It's not like that for me, and the fact that I don't have to have Google Calendar on the right side of my screen, and then SavvyCal or another thing on the left-hand side; it's all baked into one. It does look like Google Calendar, so I'm very familiar with the interface and that top-down drag and drop kind of view. So I really love that.

On the receiving end, you send me that link. What's that experience like for me?

Derrick:
So you'll receive something that looks very similar to the interface that I just looked at when I was editing. So it's going to have your baseline parameters. Honestly, when I was in there since I was making this link specifically for you, I can just prefill your information right there in the UI. When you receive it, if I've done that, then you will just see your name right there. It'll be Derrick and Pat, right on the attendee list. So that's on the left.

Then on the right, you see the calendar view, so you're seeing my anonymized availability right now, and if you're not an existing SavvyCal user, then you'll see there's an overlay in my calendar button right in the upper right; it's a little toggle switch. When you click that toggle switch, you'll see a popup that says hey, Derrick's using SavvyCal to book meetings and if you'd like to see your calendar events right on top of Derrick's availability, click this button. You can just auth whether you're using Google Calendar or Outlook or whatever.

Pat:
So I can actually overlay my own calendar on top of your calendar. I'm not seeing your meeting at 4:00 AM or not, maybe you're meeting at 4:00 AM. 4:00 PM, or I'm not seeing anything else but the time you show that we can chat. Then I can go “Hey, well, I want to see what my calendar is like. Let's overlay these things so I can see where there's actually overlap, when I have breaks and you have this availability.”

Derrick:
Yep.

Pat:
Wow, that's pretty cool. Are you finding that a lot of people are reluctant to put in their Google Calendar because it's like, “Well, that's personal information”? Who sees it? Is it private?

Derrick:
There's definitely some reluctance for sure. I think it's important to point out this overlay step is purely optional, so the scheduling flow still works regardless of whether you choose to overlay your calendar. It's a small percentage right now admittedly, that will go through this, although we do see it increasing over time. I think the hope is as SavvyCal becomes a better-known name and more trusted, little more ubiquitous, I think there'll be even more people who are not as reluctant. We do our best to try to establish trust around that.

But really, it's the best thing that a scheduler can do for their own convenience. I'm still... occasionally people now will send me a SavvyCal link to schedule time. It's always a delightful moment; it just feels like a little bit of an out-of-body experience using my own product but from that angle. When I see my calendar magically on top of their availability, it's like, “Wow, I really want this for everybody,” to be honest. It's pretty cool.

Pat:
What are some of the other features that have been added since the launch? How did you decide that those would be the ones?

Derrick:
So this is the challenge, because we talked the MVP phase is focused on, it's all about focusing on that core differentiator. The narrative running through my mind that whole time as I led up to the v.1 launch and then beyond, is addressing that instinctual question that a lot of people have which is, well, how is this different than competitor X? Because especially when you're in a well-established market with known players, that's everyone's natural inclination is to first before you even tell me anything more about your product, I need to know why I should even care. Why is this any different? That was one of the first pages that we constructed was put a lot of effort into try and make hopefully a fair assessment, as fair as we can, on casting the differences between us and Calendly and Acuity and all the big players in the space.

What this has led us to do is, we go back and forth between working on the "table stakes" features, the features that everyone expects to exist in a scheduling tool. There's a big, long list, like ability to add custom questions onto your link, the ability to make single-use links, on and on and on. There's a bunch of these kind of features that exist basically in every single scheduling tool, so it was like the playing catch-up features.

But the whole time we're always trying to weave in the features that set us apart. We have things like the schedule a time zone change. I haven't seen this in any other tool, but basically, especially as travel has gotten a little more open, if you're going to be on the East Coast for two weeks a week from now, you want to be able to tell your scheduling tool between this date and date I'm going to be in this different time zone. So just between those dates, automatically shift my availability. So we have a feature like that.

We have—time blocking is another pretty common practice. I think there are tools like Reclaim and Clockwise that help you do this on a more automated fashion, but it's definitely a strategy that we see a lot of people who are into diligently managing their time and budgeting their time will set out for the next week ahead. They'll create calendar events like, “This block of time is for meetings. This block of time is for podcast recording. This is for deep work.” So we created the ability to say if you want to drive your availability off of matching the name of an event on your calendar. So say you have a calendar event called Meetings, anywhere that event exists will show you as available for this particular link, has been a pretty powerful feature and also one that sets us apart. I don't know of any other tool that has that.

Pat:
That's cool. And to clarify, this is not a replacement for Google Calendar?

Derrick:
Correct, yeah. Not today, yep.

Pat:
You know what I mean? So when we say you can schedule blocks of time, the fact that you can do it in here where you're all eventually going to be scheduling in and around different people that you're going to be interacting with in meetings and such is really handy, instead of, “Okay, my to-dos and my productivity, I'm going to do that in Google Calendar. Then I'm going to go to SavvyCal for scheduling interviews.” The fact that it's starting to consolidate is really nice and it sounds like it could potentially get to that point where this is just all things calendar exists. Is that true? Is that in the product roadmap?

Derrick:
Still in the grand vision territory of like, within a year or two that might be on the table.

Pat:
I like that, yeah.

Derrick:
I think initially I was pretty admittedly intimidated by the notion of building a full calendar client because there's so much. Once you start getting into recurrence rules and all the complexities around managing a full set of someone's calendar events, it does get complicated, but I will also say building calendar integrations, we now integrate with Google, Outlook, iCloud, Fastmail, we're looking at a ProtonMail integration. So I'm seeing all the different dark corners, dark cobwebby corners of calendaring and getting a little less intimidated, feeling like I understand the scope of this a little better. I feel like within a year or two we might be prepared to really own the whole calendaring experience.

Pat:
That'd be amazing. That'd be really cool. This'll be a fun episode to listen back on with regards to that. Another question I have, and we're coming in closer to the end here so again, I appreciate your time, Derrick. There was a tool that I remember using that was very useful when I'm trying to coordinate, not just with one person but with several people. How do we align multiple calendars together? There was a tool called Doodle that I remember using way back in the day when geez, my bachelor party, we were all trying to figure out what times and days of the month we were all free at the same time. It was a clunky experience, and I know that SavvyCal has created something to potentially solve that problem. Can you talk a little bit about that? Because that's something that especially as communities and people are setting mastermind meetings together, it can be difficult to align multiple schedules together. How does SavvyCal help us with that?

Derrick:
We've begun to dip our toe into that, and it speaks to where our immediate roadmap lies. So right now today, you can create a team in SavvyCal and you can say, “On this scheduling link I want to show availability that works for all the people that I add who are on one of my teams.” Today it requires that everybody be in SavvyCal basically, that you want to add as an attendee where you take into account everybody's conflicting calendar events. So that was step one, and it enables colleagues within a company, like if it's a meeting with Pat and someone else from your side, you can just add everybody who needs to be in attendance and boom, you automatically reflect everyone's availability, works really smooth.

But the next step out from that is then being able to say, “All right, now I want to coordinate a time between four people who are not within the same company,” and basically it'll either work as an invitation to let SavvyCal see your anonymized availability so that we can factor it in, or potentially fall back to the polling method. That's basically how tools like Doodle do it, where it's like you pick a couple times, then you send out a survey and everyone can check the times that work for them, then you just reconcile it manually. So that's probably a mode that will me important to have, but really, the exciting part is how much of this can we automated if everyone agrees that SavvyCal will be the middleman, the broker of everyone's availability and automatically intersecting it.

You can think of possibilities like, this is one... I'll go ahead and tease this one even though it's not a fully formed idea yet, but think of it: If you were in a shared Slack channel with some other industry partners or something. This is, I have a buddy who's in channel partner sales, and he's in all kinds of these channels where they need to be able to meet regularly. What if you could just say slash Savvy in a Slack channel, and it immediately pulls the availability of everybody who's in that channel and then presents some times that people can choose right there in line with their communication? So I think there's a lot of interesting opportunities to be the broker behind the scenes on finding collective times to meet without having to do all the juggling.

Pat:
Wow, man. That would be so handy—so, so handy. Literally, bring everybody in, hit a button, “Hey, these four times are available for all of you.” Then somebody of course will have a to make a choice or the person who had set that up, but if it's available for anybody, boom, it's already set. That would save, geez, so much time. So please make that happen. That'd be really amazing.

Finally, the last question I want to ask you just for any of the entrepreneurs that are here. First of all, everybody, make sure you check out SavvyCal, S-A-V-V-Y-C-A-L.com. Always innovating, I love the work in public stance and appreciate you coming on, Derrick. I'd love for you to speak to the makers and creators, physical and digital, who are in the audience right now, who are right in the beginning stages of building their next thing. Any words of encouragement to help them through a lot of the hurdles that they're going to face, and a lot of the self-doubt that honestly comes? Maybe you could tie in a story of self-doubt that you've had through this journey to get SavvyCal to where it's at today.

Derrick:
A big thing that has helped with me is cultivating a community of people doing similar things around me. So I've always been a fan the mastermind model, having a small group of people who effectively function as an extension of my founding team. I am a solo founder, technically, but I have a couple of really close friends who were building at similar stages or some a little bit earlier, some a little bit later, who can speak into whatever challenges I'm facing. I can ask someone who's a little bit further along.

Then it's also great to be in the position of having someone who's earlier on in their journey in your immediate circle that you can then speak into their situation. It really helps, I've found, refine my problem-solving capability. It honestly yields benefits back to me; it helps me get clarity around some of the fundamentals that maybe I forgot because I've just been out of that earlier stage for too long.

Pat:
Yeah, that's a good point.

Derrick:
That's been a huge thing, whether you find that community through something the SPI community or through MicroConf, or through just hanging out on Twitter. That's honestly being... participating in the community by sharing what you're working on I've found, there's a lot of people who have made their way into my sphere. I've just seen them participating publicly, and before long they're making friends and finding people who... sometimes it's finding business partners; honestly, other times it's just finding other people to commiserate with and to support you because that's so important. It can be a really lonely journey, starting a company, and dealing with all the trials that might come.

In the last three years, I alluded to it earlier, but I worked on a product that was ambitious. It was trying to help around workplace communication and taking on an alternative to Slack. It was, honestly, it was a tough journey towards the end when I realized this business probably wasn't going to work and I had been talking about it a bunch throughout the whole time on working on it. It came to a decision point of, “Am I going to retreat into a cave and remove myself from the public realm, or am I going to just tell the story and lay it out there?” I decided to just write a big blog post about it, talked about it on the podcast, and shared that around. Honestly, that post has been the most-read piece of content I've ever written, and it was just me outlining a failure that I had, but honestly, so many people responded saying like, "Wow, this was so helpful to hear. I was rooting for you, and I felt like I didn't recognize the signs that this wasn't going to work."

So it turned into an artifact that I think has helped people in the community, which is the best thing that can happen when you have a failure. So it really takes the sour taste out of my mouth from that experience and really turns it into a good one.

Pat:
That's really great. We'll see if we can get the link for that and put it in the show notes so that others can read it too. A follow-up question to that: how did you come to the realization or make the decision that, “Well, hey, this isn't it”? Was there a particular moment, conversations you've had? How did you know?

Derrick:
It's interesting because a lot of times you get a sneaking suspicion. It was really when I... I had spent a long time building the initial version at the product, and in retrospect, took a little too long to get something in the hands of customers. I probably could've accelerated this, but I took a while. I was trying to build a really perfect prototype of it. As soon as I started sharing it with people, the reactions I got were far different from the initial excited reactions when I put out the initial manifesto for the product. So I started to have doubts creeping in, but that is a really... it's a really difficult thing to know, when is it time? When is the writing on the wall an actual reflection of reality? When is it actually time to say there's too many negative signals here and I think this is not the right thing, because I got varying degrees of reactions when I announced this. Some people said, "Well, you quit way too soon. You only put a year into this, and startups take many years to build." Yeah, I mean, they may have been right.

Honestly, I had to... for me it came down to risk profile: How much more time was I willing to commit, and was I willing to change up the type of business I was building? Was I going to go raise some funding to make this financially viable while I tried to figure it out? Ultimately had to align those types of decisions with, what are my bigger goals here? Are the choices that I would have to make to continue with this, is it worth sacrificing some of my initial goals for? Sometimes the answer is yes. In this case, it was no.

Pat:
Oftentimes when we close a project like that or step away from it, it could be very deflating. It could feel like we wasted all this time. Of course, I think we all know we learn from these things that happen so it's not a complete waste. But what, to finish off here, kept you going to end up building something incredible like SavvyCal?

Derrick:
I spent a couple of months that summer afterward really doing a lot of soul searching and spent a lot of time in a hammock thinking about things. Ultimately it came back to, this is being a maker, being an entrepreneur, sort of feels like it's a part of my DNA. I couldn't really imagine doing something different. I definitely considered maybe it's the right choice to go and get a salary, W-2 job, and there's absolutely nothing wrong with that. I think I've known many entrepreneurs who have alternated between doing their own thing and then taking some time working for another company. There should be zero stigma about that among entrepreneurs. I want to say that.

So I was at the decision of, am I really contemplating in myself, giving up on entrepreneurial aspirations, or was that coming from a place of just of fear or feeling like I was incapable? Of course, I knew that deep down this is something I can do, failure is common, that's something you have to become accustomed to but try to do your best to learn from it, and then go take another swing. So that's what I had to coach myself into. It wasn't like I woke up the next day and was ready to hit the ground running on the next thing, but yeah, it ultimately came down to rebuilding a little bit of that self-confidence through realizing this is what we do.

Pat:
Derrick, thank you so much for being open and sharing the process. Of course, thank you for keeping going and creating a wonderful tool like SavvyCal. Definitely check it out. So many of us on the team use it, and I'm excited to continue to see it grow and flourish. So, well done. SavvyCal.com. Tell us where we could find the podcast and the blog and where we could find and connect with you.

Derrick:
I am @DerrickReimer on Twitter. DerrickReimer.com is where I write occasionally, and then I podcast weekly at the Art of Product Podcast.

Pat:
Very nice, Derrick. Thank you so much. Appreciate you, and wishing you and the company all the best.

Derrick:
Thanks. This was a blast. Thanks for having me.

Pat:
All right, I hope you enjoyed that interview with Derrick. A lot of great gold nuggets in that episode, definitely one that I think I will personally listen back to, especially as I start getting into new spaces, both content and software development in the future. Definitely going to be stepping into those arenas again, and I'm definitely going to be taking advantage of all the kinds of the things we talked about today with Derrick, and as far as standing out and creating something that will take an experience that's working and just make it work even better. That's how the consumer wins. I think that's just the great thing about the open markets and the ability for us to see what other people are doing and then create something that'll ultimately make it more valuable and serve the audience better, which is really what this is all about. Serving the audience better and listening to them and getting feedback, collecting feedback along the way, and then learning how to navigate that feedback. Like we talked about, not applying every single thing that a person says, "Oh, I want this or I want that," but choosing the right things and how to approach doing that.

Such a great and valuable episode. I hope you enjoyed this, and if you of course wanted to check out SavvyCal, you can. S-A-V-V-Y-C-A-L.com. You can check it out. It's a great tool, and I expect that we are going to be hearing a lot more about SavvyCal as it starts to compete even more and potentially even overtake the popularity of something like Calendly. So, it could be tough to get a person to switch old habits, but when you see something like SavvyCal in a space where you've been using a tool over and over again and you just see some very clear advantages, it could definitely work in your favor. So Savvy, S-A-V-V-Y, Cal, C-A-L. Go Bears.

Cheers. Thanks so much for listening to the Smart Passive Income Podcast. Make sure to hit subscribe because we got a lot of great content coming your way, including a follow-up Friday episode where we're going to talk a little bit more about standing out of the crowd in competition. It's just going to be you and me on Friday. So on episode 526, look forward to that, it might be available for you already. Thank you so much, cheers, and as always, Team Flynn for the win. Peace.

Thanks for listening to the Smart Passive Income Podcast at SmartPassiveIncome.com. I'm your host, Pat Flynn. Our senior producer is Sara Jane Hess, our series producer is David Grabowski, and our executive producer is Matt Gartland. Sound editing by Duncan Brown. The Smart Passive Income Podcast is a production of SPI Media. We'll catch you in the next session.