How to Take On Huge Incumbents as a Solo Founder with Derrick Reimer of SavvyCal

Courtland Allen: 7s

What's up, everybody? This is Courtland from indiehackers.com and you're listening to the Indie Hackers Podcast. More people than ever are building cool stuff online and making a lot of money in the process. On this show, I sit down with these indie hackers to discuss the ideas, the opportunities, and the strategies they're taking advantage of so the rest of us can do the same.

Derrick Reimer, welcome to the show.

Derrick Reimer: 32s

Thanks for having me.

Courtland Allen: 33s

It's good to have you on. You're one of the people who are I'm the most tangentially connected to through the podcast, because I've had your podcast cohost, Ben Orenstein, on the show at least two or three times now. I've had your ex co-founder Rob Walling, you guys started the company Drip together, on the show like three times now. This is my first time having you on the show, so it feels like it's a long overdue meeting.

Derrick Reimer: 55s

Figure it was about time to, about time to come on and officially meet you. I've been a fan of your work for a long time and obviously aware of you and the Indie Hackers community, so thanks for, happy to be here.

Courtland Allen: 1m 6s

I was actually just talking to Rob, and he suggested you come on the show. He's like, why don't you have Derrick on? I'm like, why don't I have Derrick on? Ben said the same thing the last time he was on the show.

Today, you're working on SavvyCal, which is a super cool app. What is SavvyCal exactly?

Derrick Reimer: 1m 18s

SavvyCal is a scheduling tool that allows you to basically create a scheduling link and send it to someone else and show your availability, subtracting out when you're already busy on your calendar and basically coordinating a time to meet.

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

Courtland Allen: 1m 45s

Right. I know you're not super transparent with revenue numbers, but you told me you were willing to give a ballpark. Where are you at in terms of your success and growth with SavvyCal?

Derrick Reimer: 1m 54s

I mean, my milestone that I'm driving towards is official default alive status, I guess, where I can pay, profitable on paying my salary and all the expenses of running the business and we're right about there. We crossed $10K, heading to $20K MRR.

Courtland Allen: 2m 11s

That's the most exciting place to be, because then you’re kind of looking into your future, like, well, what do I want to do? You can do anything.

Derrick Reimer: 2m 16s

Right, exactly.

Courtland Allen: 2m 18s

Because essentially your life is in your own hands now. You're not accountable to anybody for your financial independence. Then you got to make some tough decisions, right? Do I want to keep making this bigger? Do I want to shift directions, or I want to hire and grow? Do I want to keep it going at the same pace?

Derrick Reimer: 2m 29s

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

Figuring that out is actually very difficult because me, like a lot of indie hackers and founders of bootstrapped or quasi-bootstrapped companies, we kind of hold intention, this ambition to grow something big, but also kind of maintain a healthy balance and a calm working environment. Sometimes those two are intentioned with each other, so it's always a fun game to figure out.

Courtland Allen: 3m 5s

Sometimes it changes. Early on you might be like, I just want healthy, sane balance. I want a great life. Then you get to that point and you're like, I want some challenge and I want to go for something bigger and more challenging. That's totally normal for things to change once you hit one particular goal.

I've listened to you and Ben on your podcast, The Art of Product, an excellent show. Your format is kind of just, as Ben puts it, two dudes talking. Back when I was listening to at the beginning, you're working on your company Level and Ben was working on Tupelo.

It was this weird juxtaposition because Tupelo was taking off. Ben was making money hand over fist. All his customers were super jazzed. Everything was going well. Then you were in this kind of sad, sad, depressed state where you're like, my company Level is not working. What am I going to do? You're trying to salvage it. It was just such a juxtaposition between the two of you.

I felt bad listening to you cause I was like, I really hope that Derrick makes it. I hope he figures it out cause Ben's doing so well. Now seeing that you have figured things out with your next company, SavvyCal, it's all good. It's all good vibes. I think it's almost better to listen to a failure story when a success story comes after.

Derrick Reimer: 4m 5s

Yeah. Yeah. When you know that there's light at the end of the tunnel. Yeah.

It was mentally difficult. I think something that we really strive to do on our podcast, and I think is an important responsibility of working in public is trying to show both sides of the coin, and not just project the good things, but hopefully tell the raw, honest story about what's not working well.

Yeah, it was difficult to show up on the mic every week, especially when things started to get real, started to really come to a head on like, okay I think I'm going to have a lot of trouble bringing this to market and getting real customers. What do I do now?

One of the parts, we can probably dive in that story a little bit more, but one of the parts of the Level journey that being able to deconstruct what went wrong and kind of lay the whole story out there and not, obviously you can learn personally learn a lot from your own failings, but then being, just making the decision to be open about that. It made me feel good that potentially I could help some other founders who might run into some of the same roadblocks that I did.

Courtland Allen: 5m 8s

I think it's worth going through the story of Level and then the story of SavvyCal because I mean, you haven't been working on SavvyCal for that long.

You started it last year. You're already past the $10K a month in revenue mark, which is super cool. I want to look at the differences between why did one business not work and why did the other business, why is it working so well?

Maybe the place to start is at the end of your very first business that I'm aware of Drip. You started Drip, it was an email marketing tool you built with Rob Walling, wildly successful. You guys got acquired by Leadpages, I think. You guys never shared revenue numbers, but I imagine you did pretty well and that you're sitting there earning your money. You got an earn out and thinking about what the next thing to do is, how did you decide what to do after you sold your company?

Derrick Reimer: 5m 55s

I kind of had this itch during my time of working at Drip and then, and then Leadpages, Leadpages was a team of 150 people. We were a team of 10, so we kind of got absorbed into that. Suddenly, I was in a Slack workspace with over a hundred people in it and watching kind of everything, all the business kind of increasingly being run on Slack.

We were sort of not fully in the office all the time together. So, a lot of stuff, a lot of communication being pushed onto chat as a medium. I became very, very intensely aware of all the ways that that is a challenging environment to work in without a lot of discipline. Even though we tried to all be respectful of each other's time and attention, I just was having a heck of a time trying to not constantly drop the ball and get distracted by Slack.

Courtland Allen: 6m 52s

This was in like 2015, 2016 or something when Slack was relatively new to catching on?

Derrick Reimer: 6m 57s

We’ve been Slack users for a long time. But of course, when you're a team of 10, everything's just easy. Most conversations are in the general channel and it's no big deal.

Then you get all kinds of different styles of communication all mashing together, and it kind of becomes chaotic. I sort of had, was forming this hypothesis around obviously remote work is here to stay even at that time, but now it's more so than ever, but even at the time, that was, that was a growing trend.

I was kind of sensing that there was increasing need for good tooling around to facilitate asynchronous communication in remote work. But I was just pretty well convinced that Slack was not the end all be all that a lot of people were making it out to be, and that we could do better on the product front.

I couldn't get that out of my mind. I was leading up to what felt like the natural stopping point for my tenure at Drip. We had successfully transitioned to the new team. I just was feeling like it was time to move back onto something.

In retrospect, I would have done this a little differently. I didn't take any kind of break at all. So, literally the week that I left is when I sort of published the Level Manifesto, put that out into the world and started kind of talking about the next act and I would have been better served well by a little bit of downtime to just step back, assess, think, think really hard about this and check my assumptions, but there I was.

Courtland Allen: 8m 24s

Easier said than done, especially when you're super excited about the next thing. I know a lot of people who've sold their companies and made a whole boatload of money. They're suddenly in this position where they have to decide what next?

It's kind of similar to getting to the $10,000 a month mark with your company. It's like, okay, well, what next? There's generally four approaches. It's kind of, number one, you graduate to the next level in your field. So, for a lot of founders, that means what's beyond a founder, I guess I'd become an investor or something. That's what your co-founder Rob did. Now he's investing lots of money into startups.

Number two was, you kind of keep doing the same thing but maybe you get a little bit more ambitious, you do something different. That's kind of what you're doing. You're like, no, I still want to be a founder. I want to keep starting companies. This is what I love doing. Let me start another one.

Then there's a third and a fourth option. Option number three, switch industries entirely, just go become a writer or an actor or a painter or something and just be like, I'm done with this.

Then number four is just retire, go live on a beach, do nothing. Which, to be honest, I know zero people who have done this. Even people who say they're going to do that, they just eventually do something else. It doesn't necessarily work out that way.

What do you think caused you to go down the second path of continuing to be a founder? What even is the difference in you and Rob, who decided to be an investor? What drives people down either road?

Derrick Reimer: 9m 34s

Yeah, I think Rob, Rob's about 10 years older than I am and he kind of had a head start in the industry, so he was a mentor of mine. I looked up to him. I read his book before we started working together. It was fun.

I feel like, in our conversations, I always teased him, you're going to want to get back into the game. You're gonna want to build another SaaS company. But I mean, as we know these building, these companies takes a lot of energy, takes a lot out of you. It can be pretty stressful. The highs are good. The lows are pretty tough to deal with. I think Rob was feeling like I've done that. I feel good.

Courtland Allen: 10m 13s

I hope he's listening. Robb, you're an old guy. That's the difference. You’ve had your time.

Derrick Reimer: 10m 18s

Yeah. I feel like he's kind of gets the best of both worlds now as an investor. He's an investor in SavvyCal and lots of other companies. Now he gets to lend his advice where it makes sense, but without having to feel all the ups and downs.

Courtland Allen: 10m 33s

It has got a nice as an investor and advisor where you can give high level strategic advice, but then you don't have to sit there and send out 200 cold emails. You're not doing, you're not doing the sluggish, thankless work. You're doing the fun stuff.

Derrick Reimer: 10m 45s

Yup. Yup. Coming away from the Drip acquisition, I felt like I had more products in me and also just the ambition to build something meaningful. It was kind of, it's kind of a test for me.

Before Drip, I experimented with a couple of failed attempts at startups. I was just shortly out of college and spent a couple years making all kinds of mistakes and the classic mistakes of not validating things in advance or focusing on marketing and all that kind of stuff.

Then kind of took this journey with Drip, alongside Rob and built a product on the side while doing Drip, which felt a little bit validating because it was something that I sort of brought to market and saw a little bit of success from it. It wasn't a knock it out of the park, but it was a nice, little, mini exit.

But to me, I feel the challenge of, okay, this is my time to step up and be the founder of something on my own and see what I can do. So, I do take it a little bit as a personal challenge, too.

Courtland Allen: 11m 43s

Yeah, that makes a lot of sense. Especially once you get, Rob talks about the staircase, you start with something small, take that first step. You get to something a little bit bigger, once you have these wins under your belt, it feels so much more compelling to just do something a little bit more ambitious and to kind of, I don't know, almost prove yourself to who, I don't know, maybe to yourself.

I felt the same thing. I need to prove, even in the early days of Indie Hackers, I was interviewing all these SaaS founders who were making money. I'm like, after Indie Hackers, I need to start my own SaaS business and prove that I can do the same exact thing. The question’s kind of why, why do this?

Derrick Reimer: 12m 16s

Yeah. It's funny. I'd say it's a very, I think it's maybe something in founder DNA, something intrinsic to us that just drives us to do these crazy hard endeavors. I'm not sure what it is.

Courtland Allen: 12m 28s

Would you describe yourself as a competitive person?

Derrick Reimer: 12m 31s

I would say I'm moderately competitive, but I'm not, I'm definitely not the most competitive.

I'm friends with, I have a friend who's in SaaS sales. That gives me an example of someone who's very competitive, always kind of playing the game, the chess game of business and SaaS.

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

Courtland Allen: 13m 5s

You kind of have that with every company that we're talking about. Drip, email marketing in an industry where MailChimp already existed before you started Drip. You were the David, and they were the Goliath. Then Level, Slack was already a huge behemoth, and you create Level to sort of take on the bigger guy.

Then SavvyCal, Calendly and Acuity. There's already big scheduling software and then here you are you're very new entrance. So, it seems to be the framework that you love the best is taking on these huge players.

Derrick Reimer: 13m 33s

Yeah. I would say so.

Courtland Allen: 13m 36s

Now you're at this point in your story where you've left Drip, you're like, I'm ready to do something else. I'm going to keep being a founder. You've got more ideas in you, and you ended up deciding to do Level. You published this Manifesto that's kind of Anti-Slack.

Described to me this manifesto because not very many businesses start with a manifesto. I think probably more could, but it worked really well for you.

Derrick Reimer: 13m 57s

This very much spoke to a problem that I think people felt viscerally, especially people who consider themselves to be makers. There was sort of this undertone that I was detecting of a very deep dissatisfaction with interruptive ways of working.

That is sort of the natural way that a product like Slack works. It's just sort of designed to send you push notifications and be immediate. It’s just sort of baked into the product. At the time they were floating around a term calling Slack lash or whatever, this kind of growing grassroots movement towards trying to put up defenses against Slack.

The manifesto was, remember when you first signed up for Slack and I sort of walked through this little story of at first it was good. You were just, there was just a few of you, and you would chat. Then over time, things started to devolve. It was a story that people could walk along with and really feel.

It seemed to resonate a lot. It got a lot of several thousand email addresses over the course of a few months, lots of just kind of anecdotal validation from people saying oh yes, this is such a big problem. I can't wait to see what you're going to build. I would love to use it with my team.

The indicators were looking very positive initially. User validation is super important and market validation. I was aware that getting, trying to eliminate biases from that was important. I think I didn't quite have a fully mature framework around how just to route around that, which I learned the hard way.

I collected presales did a bunch of interviews, tried to speak to the underlying problem and not my proposed solution. Yet, as it turns out, as I learned once I had an MVP ready, the actual market response is quite different than what I was hearing.

Courtland Allen: 15m 51s

Yeah. This idea that people were super motivated to read your manifesto that there's the Slacklash and everyone was talking about distraction at work. Everyone's talking about interruption-free work.

I mean, I literally just got a Slack notification while you're speaking. It's super distracting. Everyone knows it's distracting and there's this kind of pattern I think whenever anything gets big or catches on, it's kind of predictable that there will be a backlash, you know?

Okay. Social media is big. There's going to be a bunch of people who hate social media. Cell phones are big. There's going to be a bunch of people who hate cell phones. I tend to fall into the camp of like the counter, counter contrarian. Whatever comes out, everyone hates it, and then I hate the people who hate it. Just because, for no reason.

I've embraced all this distracting stuff, but the result is, I'm constantly distracted. Why did you decide to write a manifesto? Because there's so many different ways that you could potentially launch a business or test out your idea.

The only other people I know who've really started with a manifesto are people like John O’Nolan from Ghost who wrote a manifesto against a WordPress. Everyone piled on because they all hated WordPress and they wanted something better.

I think Ben also, Tuple, sort of wrote a manifesto against Slack acquiring Screen Hero. That was kind of something that tapped into this anger that people felt like, why did you feel like that was the way to go?

Derrick Reimer: 17m 8s

I felt like it was the power of storytelling. I've kind of learned that over time through podcasting, through just watching. Honestly, watching kind of Rob's example of marketing Drip. We always, for the longest time, we just had a long form sales letter as our Drip homepage, when normally people would have gone to the traditional, SaaS homepage with the little block up in the hero and all that, we just had a bunch of texts.

Rob has always been very, that was sort of his style was to be very kind of story-oriented and kind of more traditional sales letters type of stuff. That was sort of my background, too. I just felt like telling a compelling story would give me an indicator on whether people were really nodding along with this.

If I could get people nodding along, then I felt like I felt confident that I would have a market to sell to it. Didn't quite pan out. I think, wouldn’t want to bury the lead too much, but the kind of the big takeaway was that people lie to you.

They think they have your best interest in mind. They're trying not to hurt you and they want to be encouraging. I think people aren't totally aware of their own purchasing dynamics either.

In this case, I had a lot of, managed to convince a lot of champions in companies to really buy into the vision and totally resonated with the idea of saying that Slack is distractive and want something better organized.

But a lot of those people, one, didn't necessarily have buying power and did necessarily have the clout inside of their organization to get the buy-in from literally every manager or every decisionmaker who would need to be on board with ripping out the guts of their whole company communication platform and replacing with something else.

Because it's not something you can exactly dabble in. You can't just switch part of it cause then you still have to keep Slack. If everyone else in the company is still in Slack and some other department may reach out to you there. You can't either run both in parallel, which is just sort of worse, or you have to convince everyone to switch over wholesale.

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

Courtland Allen: 19m 44s

I think if you get a bunch of people, because the call to action at the bottom of your manifesto was sign up for my mailing list if you agree, basically. When you get a lot of people who are all like, yeah, I'm feeling you Derrick, this is exactly the problem I experience.

You have this innate founder optimism, too, where you're like, this is going to be so good. It's going to be super successful, I’m gonna build this cool, amazing thing. It's really, really hard to kind of simmer down and cut through the noise and figure out the right question to ask, to make sure that people actually will buy this product. Because it doesn't matter if people agree with your message. What matters is that they'll like take out their credit card and pay you the monthly subscription fee for whatever you build.

Derrick Reimer: 20m 20s

One of the resources that was shared with me kind of later on in the Level journey was sort of an eye-opening moment when I read it. It's a book called “The Mom Test” by Rob Fitzpatrick, should be required reading for every founder who needs to talk to customers ever, because it's not just for early product validation, but even I think for the process of sussing out doing a customer interview and figuring out what are people really asking for? What's the underlying problems? How badly is that problem affecting them? It just gives you a framework for basically asking questions that are so bulletproof, you could even validate an idea with your own mom, which is where the title of the book comes from.

Courtland Allen: 20m 58s

That's awesome. I love that concept because your mom is the person who's going to be the nicest to you. She's going to tell you everything you want to hear. You're gonna be like, what do you think about my startup idea, Mom? She's going to be like, it's amazing.

My takeaway from “The Mom Test,” and I've had Rob Fitzpatrick on the show to talk about it. It's funny, we joke the episode is about an hour long and that's also about how long it takes you to read his book. It's super small. It's super to the point. You could just skip the episode and go read his book.

He's really all about asking for proof. You don't ask somebody, would you use this? Or what do you think about my idea? You ask them questions like when was the last time you paid to solve this problem? Give me an example of an alternative product you're using, et cetera. If people don't actually have the receipts, then they probably aren't serious.

How did you figure out that at Level people weren't serious? Cause I mean, there was a decent amount of time that passed between you writing that manifesto and getting all these email signups, and you learning that this might not be the right idea.

Derrick Reimer: 21m 51s

Yeah. Knowing when to pull the plug is hard and when to dial back your own optimism and kind of face the reality.

After reading that book, I basically took a step back because I was kind of in the mode of trying to recruit people off my list to signup, become paying customers, and use the MVP. I was really struggling hard. I made it through a good chunk of the list that had been most engaged and was not really getting any bites.

Took a step back and started doing some more rigorous interviews, applying the mom test and hearing, just a lot of red flags, a lot of I haven't actually looked for an alternative solution, which is, that's one of the big things.

Have you paid for anything or have you even done a Google search for Slack alternative and like, well, no, not really because you know, we're so entrenched. I started to hear that stickiness just come up over and over again.

The funny thing is, I still think that it's a viable business in some form under certain conditions. I think that, and there are others. There's Twist from the Todoist team. They've been around since a little bit before I started working on Level, I think. I think they've been somewhat public with their numbers. It's been kind of a slog, but I think they're gradually growing and making some inroads.

I think it's a viable problem, but then the question becomes is it viable for me as a founder under the constraints that I'm willing to operate under? I was not willing to raise traditional venture capital to do this. I think that's maybe what it would have taken just to have more time, you know? Money gives you more time.

I think it would take lining up the timing with a certain wave of momentum in the industry where there's enough people dissatisfied and willing to adopt something else. I just kind of determined, after doing those interviews, I was already a year into it, and it just felt too risky to basically take another what I felt like would be maybe another year or two of effort to maybe yield a business that's viable.

Courtland Allen: 23m 54s

Yeah. I remember you talking about building out Level and you're just talking about I need to build this feature and that feature. You were kind of sucked into this point where there’s a potentially endless log of features that you need to build to make customers happy.

Then your sort of retrospective blog posts. You talked about the fact that there were actually kind of maybe two profiles of customers. They were the really large teams who were like Slack sucks and it's super distracting, but we're not going to switch to your newly built solution unless we have these thousand features that you don't have yet. Well, you don't necessarily have the resources at the time to build that.

Then there were the small teams who actually could use something really small and simple. But they didn't feel the pain of Slack because they had a small team, so it wasn't that distracting.

Me with Indie Hackers, we've got four or five people on our Slack and it's super easy. Then I switch over to Stripe Slack and it's this chaotic beast with like 10,000 channels. How do, who do you build for?

If you build for the small teams, you can build a product, like they don't care enough to switch. If you build for the large teams, you're never going to actually be able to build all the features that they need, because by the time you're done with that Slack will be so far ahead.

It's kind of damned if you do damned if you don't. What do you do when you realize, okay, I've been working on this for a year, it's not working out? I don't really have the patience to try to build this product for these large teams. How do you reckon with that as a founder?

Derrick Reimer: 25m 9s

Well, you rent a cabin in the woods. Step one, which I did, I actually did. I went on a little retreat. It's like, okay, I need to become comfortable with this decision.

I can either have a freak out moment and completely retreat away from this endeavor. Or I can kind of just take a step back, breathe, evaluate, and try to get a clear mind to make a decision on this.

That's what I did. I actually spent time writing that retrospective post. It sort of took me a couple of days of just kind of working on it and then just doing other reading and hiking and other things to get my mind clear.

I felt like by the time I finished that, I was like, if I can write a retrospective where there's a clear logic to the decision and conclusion at the end of this post is that yep, this is why I made the call to move on. If I could compose this, then I would feel comfortable in me that I, that I was actually ready to call it on it.

Then the bonus is that I got this deliverable on the other side, which was a post that I could share with the community that did get a lot of positive response people. A lot of people resonated with the story.

Courtland Allen: 26m 29s

Yeah, I think Rob ended up posting it to Hacker News and it got like 500 up votes. Then a ton of comments, it was very public, top front page of Hacker News, thousands of developers and founders reading kind of your retrospectives and then giving their own feedback as to why Level didn't work out, et cetera. What did it feel like to read those comments and be so public with what happened?

Derrick Reimer: 26m 52s

I think it was a mostly positive experience, honestly. There were definitely some dismissive comments, some like, oh, what only put in a year? Then of course, most people recognize this is still a year's worth of time.

Definitely it was interesting to see kind of the varying perspectives from the more traditional Silicon Valley lens versus kind of the more Indie Hacker lens, two very different ways of viewing this whole story.

Courtland Allen: 27m 22s

Then I think like 10 days later you had another post that I went to the top of Hacker News called “Finding my next bootstrapped business idea.”

You're kind of outlining your process for how to go about looking for a business idea. You had a lot of good stuff in there. You talked about the fact that the market already needed to exist.

You talked about a lot of the internal motivations, too. Why am I even doing this? Why do I want to start a company? What's going to make me happy? What are my ambitions? How do you think about that today?

Derrick Reimer: 27m 48s

It was really helpful to go through that exercise because I think it's important to first know yourself, know what you want out of it.

One of the things I put in there, this needs kind of some explicit timelines on being able to reach certain milestones was really important to me. Especially when you're not dealing with an infinite runway, or you're not willing to go out and raise the money to give yourself a really, really long runway. Getting to those milestones quickly was really important.

Part of it was just digesting lessons learned on what not to do again. Some of it was just sort of reaching my own maturity on mindset stuff, which is always a work in progress. I think founder-market fit is so important, too, to try to strive towards first and foremost, and then kind of let the rest fall from that.

Courtland Allen: 28m 44s

You can kind of tell that you've been through the ringer a bunch of times when you are a founder, and you have this list of I will not do this. This is my constraint. These are my cutoffs. Every grizzled founder has a list of things they're not going to do anymore. I just want to read through your list in the blog post, because you've got a bunch of stuff here.

You've said the product should not be mission critical. You don't want to build anything where you having downtime is going to affect your customer's businesses, which is probably a stress thing. It's super strong. If Indie Hackers goes down, I'm sad, but no one's life is ruined. No one has to go to Indie Hackers and it's kind of good. It's kind of relaxing.

You said your MVP, your minimum viable product, must be shippable within a few months. You said the market must already exist so that making a sale shouldn't require more than a few decisionmakers; you don't want to have to deal with a whole giant pipeline of people you have to convince to buy your app.

You said that native apps should not be a minimum requirement. People come to expect the native desktop app and the Android app and iOS app. You just didn't want to have to build all that to sell your product.

Then finally you said the market should overlap with your existing audience that you've already built up over years of building products and building in public and tweeting and speaking and all sorts of stuff.

Derrick Reimer: 29m 49s

That last one is another piece, there's this debate always goes on of are you required to build an audience in order to build a successful software company? I'm definitely one that would say, no, you're absolutely not required.

What you should do, what is the smart thing to do is to just look around you at what are your unfair advantages that you potentially have and try to make the most of those. For me, this was a pretty considerable one.

I've been investing in the podcasting for a while and kind of publishing online. I could do myself a service by trying to find something that I could sell to those existing people who are already kind of in the circles.

Courtland Allen: 30m 28s

How did you go from this point where you're kind of wandering through the wilderness? I mean, you're literally in a cabin in the woods trying to think about what to do next to deciding that you're going to do SavvyCal, which is what you're working on today.

Derrick Reimer: 30m 39s

That was the most challenging time to be honest, because I wanted to get down to work on something. I wanted to really sink my teeth into something, but I really didn't know what I was going to do.

And I sort of had the summer in front of me and spent a lot of time in a hammock thinking with my idea notebook had kind of scouring back through past ideas, and just kind of dreaming. Having the pressure to come up with an idea is really hard, but I was like, I have a couple options.

Plan B, plan C. They weren't all that bad. I could go get a job. I think there's absolutely zero shame in doing that. That's where entrepreneurs a lot of times get some of their fresh ideas is from working in someone else's company and observing all the things that are broken, you know? I think that's a perfectly reasonable path to go. I did entertain that.

I also don't want to treat ideas as too precious in their own right. I just wanted to kind of follow a framework of let's explore problems cause there's tons of problems all around and kind of explore and see what I uncover. I ended up working for a little while on a product called Static Kit.

It was a suite of tools for people using static website technologies, being able to embed forms and rich client side stuff on your static site. I didn't really have a super clear vision for where to take that, but it was sort of an in-between, like I like this kind of technology space and I want to play with some of this stuff and just kind of keep shipping stuff into the world.

I did that for a while and I think it was a positive experience, even though it wasn't a knockout success, but it kind of kept me busy and kept me thinking for a little while.

Courtland Allen: 32m 28s

Do you think that being so public with everything, cause you're relaying all of these experiences on your podcast. Do you think that motivated you to basically keep trying and not go get a job? Because if no one knew what you were up to you, it probably would have been easier to be like, I quit. I'm going to get a job. I'll come back next year.

Derrick Reimer: 32m 44s

I think that was definitely a factor. Yeah. I did think about stepping back from the podcast for a little bit of time during that period, but I was like, you know what? I don't want to get out of the game ultimately.

I still felt a strong pull to be in it in part because of the podcast and things like that. I thought that is a good forcing function, I think, but not always easy. Not easy on the ego either.

Courtland Allen: 33m 8s

I love social accountability. I love having any sort of, I don't know, pride or shame or status or reputation, any other people you can bring into what you're doing. Because if you think about it, we all have our jobs. If you have a job, you'd probably have a boss, you probably have coworkers, you have other people who can kind of see the output of what you're doing.

Maybe it's hard to explicitly always know that that's motivating you, but it probably plays a role. The second you become a founder, unless you're broadcasting what you're doing to lots of people, you kind of lose that motivating factor. It's just you and sometimes it's easier to let yourself down than it is to let down an audience of thousands of people listening to your every word on your podcast.

Derrick Reimer: 33m 47s

And investors. I raised some TinySeed funding basically shortly after the after the Level wind down. That was that was Rob and Einar making a bet on me as a founder, and saying we think you're going to do some interesting things.

That was both a stress reliever, but also caused me to put a lot of pressure on myself, I think. Because now I'm dealing with other people's money. Other people have skin in the game here. It's funny how a lot of times some of the things that should be a relief are also a big stressor.

Courtland Allen: 34m 23s

Exactly. Yeah. I feel the same way with Indie Hackers at Stripe where it's like this would be a really fun, done with the solo part. But it's like, no, actually this big company bought my company and I feel a lot of pressure to make it a worthwhile purchase for them.

And I think that pressure is kind of good. Because in a lot of ways, as an indie hacker, if you’re aiming for freedom or you're aiming to live a really good lifestyle, you kind of start your business and almost on day one, you kind of feel like you've made it.

You're like, I don't have a boss anymore. I quit my job. Or I'm working for myself and it's really easy then to just take all the pressure off yourself and be like, I'm going to live a life of freedom and ease, but you probably can't really do that until you've gotten to where you've gotten with SavvyCal.

Until you've gotten to the point where you're profitable, it's probably dangerous to start thinking that way until you've already been successful. Ironically, choosing to be an indie hacker probably should mean choosing to put a lot of pressure on yourself and to be accountable to other people until you get to that point.

Derrick Reimer: 35m 13s

Yeah, I think that's kind of the hidden secret or quality about indie hacking. There's a lot of people who kind of see there's the pockets of digital nomads and people who are like, I'm going to do the geo-arbitrage game and keep my expenses low and get just enough income so I can have this lifestyle of adventure or whatever you want to optimize for.

But I think also those of us who kind of get into this game of running our own companies also get tugged by that ambition factor. Before you know it, we actually do want to want to do really interesting things that stay challenged. That challenge kind of just draws you towards more and more ambitious things, which does kind of encroach a little bit on the carefree, easy lifestyle part that kind of entices a lot of people.

Courtland Allen: 36m 0s

Yeah. And it's this weird, almost the opposite sort of what your goal is. You end up getting dragged into it and it's kind of our own fault. We do it to ourselves.

Maybe there's just something more interesting about it overall. Maybe the dream that we want, the super carefree easy life is not necessarily what we want.

Derrick Reimer: 36m 15s

I think that might be sort of the dream of retiring on a beach after you sell your company, which no one ends up actually doing that or being happy doing that.

Courtland Allen: 36m 23s

At least the kind of person who is going to create a super successful company is not the kind of person who's wired to go do nothing for a very long time.

Derrick Reimer: 36m 28s

Yeah. I think we're most fulfilled by challenging endeavors ultimately.

I think I remember listening to a podcast from, she was the right hand executive at Netflix and kind of talking about how the best days when you come home from work, the best days are when you're collapsed on the couch and go oh my gosh, that was such a hard thing we just did, and we accomplished it. It's not the days where like, oh, nothing really happened. I went in and sat at my desk for a little while and left early. Those aren't the fulfilling days or the ones that you remember.

Courtland Allen: 36m 58s

It's weird because there's also a lot said about sort of the toxic Silicon Valley startup culture, where everybody's overworked. They're sleeping under their desks and the whole team staying up late. But often when you talk to people in those situations, those were the best times.

The people really remember those times that they're bonded together. It's almost like a tribal, you just go through hardships with people who are your comrades and who are your colleagues, and then you come out the other end and that's what you remember.

Let's talk about the beginning of SavvyCal, because eventually you decided to start SavvyCal and this kind of fits your pattern. There already was one or two big incumbents in the space who were already doing this well. Why did you think that the world needed another scheduling application?

Derrick Reimer: 37m 40s

Yeah. I had to become a user of Calendly for many years. We integrated with them at Drip pretty early on because we were using them for demos and we needed to track when someone scheduled something, we automatically put them in a workflow.

So, I was very aware of the tooling and kind of the problem space. Of course, I've used it to schedule customer interviews for all the products I've done in the past. So, sort of understood the underlying problem here. But the thing that really got me intrigued by it was kind of observing the weird power dynamic issue that arises around using scheduling links.

There are some pockets of industry where people just literally refuse to use them because it's just too faux pas. It's too laden with landmines. You might end up offending somebody. They just always fall back to the inefficient way of scheduling times. Then other people like are just, I want to use it, but other people are super hesitant.

It was a curious thing to me that there's this tool that, or this whole class of tools, that save people a ton of time, and yet there's all this resistance to using them. It's both a product problem and a people problem.

They're elements of etiquette and ways to just communicate well so that you don't turn someone off when you're sending your communication and including a link. So, I think it's two-fold and I think that I wasn't seeing a lot of innovation happening on the product front around trying to actually make this better, make this a more collaborative experience, reduce friction as much as possible for the scheduler.

I kind of felt like things were just sort of status quo for a while. Yet this is a highly demanded tool. I mean, I didn't plan on demand increasing even more during the pandemic, because I started right around the beginning of the pandemic actually. That's what kinda got me interested in the problem space.

I also kind of compared it against my rubric that we had went through, some of these criteria that I've been building up over time. People can use it in a single-player mode, an individual can just start sending out links for themselves and then gradually their team can hop on.

It's important, but if I need 10 minutes of downtime to do some database maintenance, it's not a big deal. It kind of checked a lot of the boxes. So, then just the question became do I even stand a chance against extremely successful and an overall well-liked competitor like Calendly?

Courtland Allen: 40m 14s

Right. Can you explain to people how an app Calendly works? I assume most people have used this, but probably a lot of people have no clue what problem this is even solving.

Derrick Reimer: 40m 22s

You basically create your account, and you attach, you link your calendar to it. You authorize your Google calendar or Outlook calendar, whatever you use, and then you create a link, and the link basically gives you your availability minus any existing events you have on your calendar so that people can find a time.

Courtland Allen: 40m 41s

It makes it so much easier to scale because I use this with the podcast. I'm like, hey, Derrick, let's find a time. I send you a SavvyCal link and you click it, and you just know exactly what times are free on my calendar that I've specified. I don't have to do anything. Then I just look at my calendar the next day, the next week, and your event is on there. It's like having almost a personal secretary or something or assistant who's just helping schedule.

Derrick Reimer: 41m 1s

Exactly. Yeah. Your kind of more classic busy executive may have a personal assistant. So instead of using a link, they would just copy their assistant on an email thread and say, I'm going to hand you off to so-and-so to coordinate this.

Courtland Allen: 41m 16s

Nowadays the assistants are just using Calendly and SavvyCal and the like, too, they're just like, here's a link, pick something.

You’re kind of staring this idea in the face, it's doing really well on your checklist. I think probably the only item on your checklist that it might not be perfect on is the fact that it might be mission critical to a small degree. People might be upset if it goes down, but like you said, it's not the biggest deal in the world.

But you've got to face down this huge incumbent that people kind of like, it works well enough. I probably haven't had very much time using Calendly or regret using Calendly. What's your playbook for building an app that takes on a huge incumbent? How do you know if it's a good idea to try to build something in a space where people are already solving that problem really well?

Derrick Reimer: 41m 54s

I'm hesitant to say that it's a repeatable playbook because I think it's every app is a little different. Every industry is a little different. But what I recognized here that gave me that gave me confidence was that I sensed some stagnation, some of the bigger incumbents slowing down a bit.

That's kind of a natural thing to happen as you grow in size. Calendly has hundreds of thousands of customers and millions of people using the product. It's just hard to turn that ship quickly and be able to respond quickly to what customers are demanding.

I started looking around and seeing a lot of while there is a lot of love for the product, there's also a lot of dissatisfaction out there on forums. I kind of did the thing of scouring places where people are talking about not just Calendly, but all the tools. A lot of people publicly asking for things, expressing dissatisfaction with things on and these threads just kind of sitting around for a couple of years with no real response.

That's a sign that this company is both really successful. They're doing really well financially, but they're not responding so quickly anymore to what customers are wanting. I think that's the crack where an indie hacker has an opportunity to...

I didn't know if it was going to look like carving out this little niche and was SavvyCal gonna become like scheduling for X, something very narrow and specific. I wasn't sure how narrow I would have to go. I mean, this product lends itself to more of a horizontal type of positioning just because it is so broadly applicable.

I sort of held loosely onto that initially. I think April Dunford’s positioning book, which is one of my favorite resources, she kind of taught it's about intentionally keeping your positioning pretty broad cause you're trying to have like a big fishing net to capture a lot initially.

It was kind of keep the net wide but be on the lookout for very specific things and ultimately kind of double down on something. I kind of chose this angle of the awkwardness piece and really just kind of tried to get my MVP done as quickly as possible, honestly.

Beyond that, talking to potential customers, I got a lot of people expressing skepticism. Like, I don't know, man. I think this one's locked up already. It did take a little of a leap.

Courtland Allen: 44m 29s

Right at the top of your landing page, it says, sending your scheduling link shouldn't feel weird. You're a hundred percent in on the awkwardness and the feeling of it and reading that, I feel that pain.

That's definitely a problem that I've had with scheduling links. It definitely feels a little bit awkward. That's kind of a cool way to carve out your own niche in an industry that's already got…

I wonder what does Calendly’s homepage say? What is their sort of claim to fame? Calendly.com says, easy scheduling ahead. So, they’re about ease of use. It's super simple. It's easier than other apps. You just have your own sort of your own benefit.

Derrick Reimer: 45m 2s

And I think I got to draft off of a lot of the awareness that they've built up to. I'm primarily getting people who are coming from Calendly, have been dissatisfied with it, looking for the power dynamic stuff to be resolved.

I mean, they, I think in the early days of Calendly, it was they were having to teach people what this tool even is and how it works. That's another thing, you ideally want to be in the position where SavvyCal is today, where there's a bunch of people who are already very aware of this problem space. Now they're looking for something a little different on a few things that, and if you can execute on it, that's where the opportunity lies, I think.

Courtland Allen: 45m 38s

I’m looking at this in action because their homepage is all about educating people, even still. It's you can schedule meetings without the back and forth emails and here's how it works. Here’s what you do.

Your whole thing is a hundred percent predicated on people already knowing this. Scheduling your link shouldn't feel weird. That only makes sense to people if they know what a scheduling link is. You say finally, a scheduling tool that both the sender and the recipient will love.

Again, that only makes sense if people already know what this is. So, you're selling to a kind of a more educated, more experienced market of, I guess, disgruntled scheduling tool users.

How do you avoid some of the mistakes you've made in the past, though? For example, with Level, one of the hard things was you just had to spend a lot of time building features because you're taking on this incumbent, Slack, that already had a ton of features that people expect.

It's probably the same with SavvyCal. You start off day one and guess what? All, especially since you're sort of catering to these existing users who already know. They already have some minimum level of expectation for well, does this do everything that Calendly does? Which might be a huge, months’ long slog for you just to copy all these features.

Derrick Reimer: 46m 41s

That was something I was deliberately trying to get out in front of this time around. Really the way I mitigated it was engaging with anyone who came in, came in the door, put their email address on. I tried to spark a conversation with them to figure out what exactly are you looking for? What's the minimum that you need in order to use this product?

I did push it pretty aggressively when I first started inviting people in June, July. I was just a couple of months into the product, and it was missing a ton of features. I mean, we're still playing catch up on a lot of the, the long tail of features, that people expect.

But I found there's actually kind of the 80% rule. There's a lot of people that are not using that other 20% of features. It seems like the majority of people just kind of need to be able to present their availability and all the rest of the stuff it's like nice to have.

Trying to get clarity as early as possible on how essential is that, is it a nice to have, or was this a deal breaker?

Courtland Allen: 47m 44s

Yeah, that makes a lot of sense. Cause I'm the kind of person that doesn't really need, Calendly has a million features that I just don't need and all sorts of integrations and things. Some people need it, but I just need the basics.

Then since you're kind of focused on the scheduling screen, I send somebody the link, they click the link and then they get the see my calendar. That screen that you have is super friendly. It's super customizable. There's all this stuff that I can put on there to make it a good experience for them. So, it kind of delivers on your value proposition of it shouldn't feel weird. I shouldn't feel awkward. I shouldn't feel like I'm insulting the person by sending them this link.

What about growth and marketing? The other thing that's hard is the incumbents are sort of creating this market. They're educating people, but also because they're the ones educating people, everybody knows their name. Especially with the scheduling stuff, it's a little bit viral where when somebody sends out a scheduling link, everybody now, the recipient sort of hears about that.

It's kind of like greeting cards. Nobody buys greeting cards and just keeps them for themselves. Everybody who buys a greeting card gives it to somebody else. So, it's a naturally viral product.

How do you, this brand new player who no one's ever heard of, cut through basically the noise and get people to start using you instead of Calendly? How do you get people to even find you?

Derrick Reimer: 48m 50s

Yeah, that's a great question. I think that quality of every time someone uses my product, they're inherently exposing it to other people, that was one of the big kind of selling points to me in choosing to take on this endeavor because that kind of viral loop is extremely powerful.

In listening to, kind of deconstructing how my competitors have grown, that is kind of the number one by and large kind of growth path for them. For me, it was kind of about working as hard as I could to recruit as many people from my sphere who were listening to my podcast, following on Twitter or whatever, to start using it and then just inherently spreading it to their second degree contacts and on.

Courtland Allen: 49m 40s

Has that worked out? Cause that's the holy grail of every software engineer wants to build an app that once you build it, it just spreads itself and it's just growing on its own and you don’t have to do anything because it's just naturally viral.

Derrick Reimer: 49m 52s

I do think it's working. It's extremely hard to track in a way that's not totally invasive of privacy I feel like. We've kind of taken a stand of trying to use privacy, aware tooling as much as possible. I'm a big Fathom Analytics fan.

Figuring out all the multiple touches that people have with the product and was that touch where they received a scheduling link scheduled something. At what point did that touch occur in their awareness cycle? It's very hard to suss out. I want to get more sophisticated about it.

Anecdotally, we started asking kind of a question we added to our onboarding, how did you hear about us? Basically, to get some qualitative data on that. It definitely gets cited quite a bit of I used a link with someone else. So, I think it is working

Courtland Allen: 50m 42s

What else are you doing? Are you doing any content marketing? Are you doing social media marketing? Do you have a mailing list? What else are you even trying to do besides relying on the word of mouth griff?

Derrick Reimer: 50m 52s

Yeah, we've experimented with some podcast ads, which are very difficult to track aside from using a coupon code when you hear it mentioned on the ad. But I think that is definitely driving awareness.

We're working on some strategic SEO stuff. Just kind of digging in doing our keyword research, digging into that and making some strategic landing pages. We are kind of spinning up, we’re in the process of spinning up an affiliate program right now.

It's sort of a grab bag of things. I love to reference the “Traction” book by Justin Mares and Gabriel Weinberg and sort of their thinking on trying to craft things as experiments as much as possible to suss out the viability of traction channels. That's sort of where we're at on trying to figure out what's the real breakout, insert $1, get $3 back out the other side flywheel going to be.

Courtland Allen: 51m 52s

Yeah. It's explore and exploit. You got to explore a bunch of different options. You got to put in enough effort, such that you can actually test it out and come to some sort of believable conclusion as to whether or not it will work, but not so much effort that you don't have time to try other channels and try other things. Then when you find something that works, you do exactly what you're saying, press the gas pedal and go a hundred percent on that.

It's pretty inspirational and heartening to see that you haven't necessarily found some magic bullet and yet you’ve still been able to get to this level of success. Even the other things you haven't done, you haven't perfected your user tracking and figuring out where people are coming from.

Yet you're still able to make a profitable company. You don't necessarily have to do the entire kitchen sink to get to the point where you have a successful business.

Derrick Reimer: 52m 33s

Yeah, so much of business success, I feel like is despite all of the things that we have locked in. This is what I've learned in working in Drip post-acquisition seeing what Leadpages looked like on the inside. I mean, most companies are pretty chaotic on the inside and there's just a lot of moving parts and a lot that doesn't end up working out. Yet thankfully businesses just tend to march forward.

Courtland Allen: 53m 0s

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

Where do you think things will go from here? What are you excited about with SavvyCal now that you've gotten to this point of profitability?

Derrick Reimer: 53m 15s

Yeah, this does feel like kind of an inflection point for the business. We've made it past that $10K mark where it's like, okay, if you can make it past that, and growth is not plateaued, I think we're onto something. So, I feel like that box is checked, which allows me admittedly to breathe a sigh of relief a little bit.

Now the question becomes how do I think about expanding the team? That's kind of what I'm thinking about right now. I'm wearing too many hats right now, so I'm getting some help on support. I'm getting that ball rolling next week, I think.

Then looking to make my first engineering hire to really help contribute to the product, which is daunting because I know what a big deal it is to kind of make that first hire. I'm thinking about how do I want to, what do I want my day-to-day to look like?

Honestly, my fondest memories from building Drip were the earliest days where there was a couple of us that would come into an office a couple of days a week. We were still flexible. We would work remotely a ton but being able to collaborate in front of a whiteboard and then go grab happy hour later in the day was just really nice.

I think there will be a little bit of a resurgence of some partial in-person work with some of that high fidelity, human communication stuff that's really hard to replicate virtually. I don't have that part figured out yet, but it's something I'm thinking through.

Courtland Allen: 54m 48s

That's kind of the fun stuff to think about because if you start a company, you can structure it however you want. I mean, if you really don't want any human contact, you can be like, I want a remote company. We're not going to do video chat. Zoom is not allowed. Do your own thing. You only hire people who thrive.

If that's the life you want, you can do that. If you want to hire people who are local, who are extroverts, who want to meet in person, you can do that and have like a really great soul. You can do literally anything that you want with your company.

Kind of that post where you're writing down what do I want with my life? I feel like that's a question you should probably always be asking yourself as a founder. I'm still asking myself that with Indie Hackers every month, trying to figure out where I want to go.

You've been through it a lot as a founder, you've had lots of ups and downs. What's one takeaway you think a fledgling new indie hacker could take away from your journey so far, Derrick?

Derrick Reimer: 55m 30s

I think the probably the biggest piece of advice I would give is to, if you're like me and you're an introvert and your natural tendency is to dive into the code and kind of focus on product, is to get outside of your comfort zone a little bit. Really try to actively engage in the community, whether that's online on a place like Indie Hackers or in your local town.

I think if I reflect back on my own journey, the biggest driver towards my success has been kind of the different kind of small groups that I've been a part of. Mastermind groups and seeking mentorship, that really helps you to sanity check your own assumptions and keep you on the right path when you have other people who are kind of intimately aware of the stuff that you're working on and kind of sanity checking your ideas.

Courtland Allen: 56m 22s

I love it. I've had the same exact experience. Introvert as well, spent years locked in my apartment, building stuff without talking to anybody and didn't work very well.

Then the second I started something where I'm talking to people for a living it worked really well. So, introverts out there, make sure you're actually connecting with people and sharing what you're up to you.

Derrick Reimer, thanks for coming on the show. It's been a pleasure having you, have to have you again. I've had Ben and Rob a whole bunch of times.

Derrick Reimer: 56m 45s

I got to catch up.

Courtland Allen: 56m 47s

Yeah. Where can listeners go to learn more about what you're up to you with SavvyCal and everything else nowadays?

Derrick Reimer: 56m 52s

Yeah, the product is at savvycal.com. I should have mentioned this earlier, but I have a special coupon code for the Indie Hackers audience. Just use indiehackers in the checkout flow to get your first month free.

Then you can find me on Twitter, @derrickreimer.

Courtland Allen: 57m 8s

Sweet. I'll put the Indie Hackers coupon code in the show notes as well. Thanks again, Derrick.

Derrick Reimer: 57m 12s

Awesome. Thanks.