The Castle Blog

by Max

We’re exicted to announce that earlier this month, Castle closed a fundraising round of $270,000 from a fantastic group of angel investors.

Raising money is hard, and for first-time founders like us, it can be even harder. Throughout our fundraising process, which lasted around five months, one thing that was especially helpful to me was looking at other companies’ pitch decks.

But aside from a few prominent examples, finding pitch decks can be really hard. Early on in our process, I was inspired by another deck to completely redo an early version of ours. But I only saw that deck because one of that company’s investors shared it with me privately.

We think this is a shame. So, in the spirit of transparency, we’re sharing the deck we used to raise our angel round. We hope it can be as helpful to other founders as seeing others’ decks was to us.

Questions? Comments? I’d love to hear from you. Email me at max@entercastle.com.

by Max

“So, how’s Castle going?”

I get asked this question all the time—by friends, family, acquaintances, strangers, and Tinder dates who Googled me before we met1—and I never know how to answer.

I procrastinated all morning, but a bunch of inbound sales leads came in without my doing any work, so we gained three customers even though I wasted half my day. Good or bad?

An investor told me he’s not interested in our business, but he wants to support us personally, so he’s investing anyway. Good or bad?

We signed some new customers and made some great improvements to the product, but I’m filled with a horrible sense of free-floating anxiety for reasons I don’t understand and can’t explain. Good or bad?

Free-floating anxiety, courtesy of the always-brilliant Garfield Minus Garfield

Most of the time, I can answer the question anyway. I just say “It’s going great.” Or “It’s challenging, but rewarding.” Or, “Everything’s fine, mom, now leave me alone!”

Still, the question begs another: how should we best measure our progress? Yes, we have metrics: new customers, movement on the product roadmap, owner satisfaction. But while those metrics help reveal how the business is going overall, they don’t say as much about how it’s going for me personally.

That’s why lately, my focus has been on optimizing for learning. Whether the tasks I spent my time on succeeded, failed, or hit somewhere in between, my week was a success if I came out knowing a whole lot more than I did when I went in.

Viewing my experiences through the lens of learning changes how I feel about them. Lost a customer? It’s okay, as long as we learned from our mistake. Gained ten customers? Celebrate all you want, but if we don’t know why we closed them, or how we can replicate that success going forward, it’s not much of an accomplishment.

I’ve learned more in 2014 than I have in any other year of my life by far. Here’s hoping—no, planning—to make that rate of learning even higher in 2015.

1. I swear this actually happened. ↩

by Max

Q: What’s the difference between an English major and a large pizza?

A: A large pizza can feed a family of four.

I heard this joke all the time when I was in college. And it only got worse when I revealed that my concentration was creative writing. As if being an English major wasn’t enough, I had to spend all my time doing… well, what is it exactly that creative writing students actually do?

If your family is anything like mine, you actually need more than one large pizza to feed them.

I didn’t become a creative writing major with the intention of getting a creative writing job (whatever that is) after college. My school wasn’t very career-focused, and I figured I’d spend my college years doing whatever I enjoyed doing, then figure out the rest later1.

And for a the first couple years, I did just that. I had a few opportunities to use my English chops writing marketing copy and press releases at my first job, but there weren’t any moments that made me say “Thank God I’m an English major.”

A classic from For Lack of a Better Comic

Then I started Castle.

As CEO, I spend most of my day doing exactly what I practiced during all those late writing nights: storytelling. My job is to communicate the story of Castle to customers, to investors, and to the team. In fact, almost everything I do involves storytelling:

• Sales (stories sell, features don’t)
• Web design (start with the words)
• Interface design (copywriting is interface design)
• Fundraising (investors back the company you can become, not the company you are now)
• And, of course, hiring.

You could even argue that our financial projections are a form of storytelling2. Yes, they’re a bunch of numbers, but those numbers tell our story for the next year: how much business we plan to do, how many people we plan to hire, and how much we plan to spend on yachts.

Just kidding.

So while I’m not going to get a business card reading “Chief Storyteller” anytime soon, those trusty old writing skills have served me very well with Castle so far. My English degree may not be feeding a family of four anytime soon—but it’s done a pretty good job feeding a founding team of three.

1. Apparently my attitude isn’t very common: English, like the rest of the humanities, has been steadily declining as a major for several decades. ↩
2. Any seasoned entrepreneur will tell you that they’re definitely fiction. ↩

by Max

In my last post, I explained that our original plan for Castle—software tools for independent landlords, beginning with rent collection—had failed. Actually, I didn’t say “failed”; I said that we’d realized we needed to go beyond software alone to fully achieve our vision of automating landlording. And that’s true—but it’s also true that pursuing our rent collection tool hadn’t worked out as well as we’d hoped. This post is an attempt to explain why.

First, let’s look at where we ended up. When we made the decision to shift our focus, we’d been building and selling our rent collection tool for a little under three months. We had eleven landlords signed up for the beta, with another ~100 at various stages in the sales pipeline. (Of course, we knew this approach wouldn’t scale, but the approaches successful startups take to get their first customers rarely scale.)

Our Streak pipeline as of October 2014

Our sales process (inasmuch as it was a “process”) was simple: we’d have an initial conversation with the landlord that was all about them, to learn about their needs and build the relationship. Then, we’d walk through a demo of Castle with them, primarily to get their feedback. We never did any kind of hard sell—instead, some percentage of people would express interest in using Castle when we showed them the demo, and we’d sign them up.

A slide from our demo deck

Rent collection as MVP was failing lightly, which is the most dangerous kind of failure. We were making some progress, and we could’ve probably kept going like that for a while, signing up new customers at a steady (but rarely increasing) clip, maybe even raising a little money. Having just enough “success” that we never felt like we were falling flat on our faces. But it was never going to take off.

Ultimately, with rent collection, we failed to make something people want. It was a tricky kind of failure, because landlords “want” rent collection, they just don’t want it. When we talked to them about it, they often said they were interested in it, but it was more of a “sure, I guess I could see myself using that,” not a, “Yes! I want that!”

Paul Graham says you need to make something a small number of people want a large amount. Peter Thiel says the same thing in a different way: that you should gain a monopoly in a small market and then expand with the market. Rent collection is the opposite: a large amount of people want it a little bit.

We knew this going in, or at least we should’ve: there are tons of other rent collection services. If landlords really wanted online rent collection that badly, they could find it with a quick Google search.

We believed that none of these other rent collection services have really stuck because they mostly did a bad job with the execution, and because rent collection on its own isn’t enough—it’s necessary, but not sufficient. We still believe that to be the case. But the writing on the wall is clear. And that’s why we’re moving in a new direction.

We started Castle with a simple mission: to automate landlording.

Most landlords buy properties for the same reason they’d buy stocks or bonds: as an investment. But unlike stocks and bonds, which you can buy with a single click and then forget about entirely until it’s time to sell, real estate comes with a job. And though it’s often a great investment, it’s a lousy job. Landlords and tenants suffer because the rental experience is messy and over-complicated.

Our first plan was to solve this problem with software tools for landlords: starting with rent collection, and then expanding to cover every touchpoint of landlord-tenant interaction. But over the past several weeks, it’s become clear to us that to achieve our vision of fully automated landlording, we’ll need to go beyond software alone.

That’s why we’re introducing the new Castle: full-service property management you’ll actually like. For a flat fee of $49/unit/month, we’ll handle everything that needs to be handled, from collecting rent and keeping the books to managing repairs and even finding tenants.

Current property management companies have two critical flaws: they’re expensive (usually around 10% of rental income), and they fail to provide owners with a clear picture of what they’re doing and where their money is going. Landlords we’ve talked to have described their dealings with property management companies as feeling like “scams” and “ripoffs"—and those are just the phrases we can print on a family-friendly blog1.

We’re going to change that.

Castle has simple, fair pricing: just $49/unit/month. Our work is the same whether your property rents for $500 or $5,000, so charging a percentage of rental income, like almost all other property management companies do, just doesn’t make sense.

We’ll also be the most transparent property management company you’ve ever seen. The Castle app will give landlords a full behind-the-scenes look at what’s going on in their properties, so they can understand where their money is going when they use Castle’s services.

Down the road, we’re bursting with ideas about how we can grow and scale by using technology in ways that traditional property management companies have barely scratched the surface of. But that’s for another day. For now, we’re focused on getting our first units under management.

Oh, and if you liked using Castle to collect rent? Don’t worry—you still can. Even better, it’s completely free, for as many properties, tenants, and payment cycles as you want.

We’re super excited about the road ahead, and can’t wait to get going. Stay tuned!

1. Disclaimer: this blog not guaranteed to be family-friendly.↩

Each week, we’ve be introducing you to a member of the Castle team. This week, we conclude with CEO Max Nussenbaum.

What’s your favorite part about working at Castle?

The constant challenges. With the possible exception of all of seventh grade, I’ve never felt more scared, confused, or unsure of myself than I have over the past few months. At the same time, I’ve never been learning as much as fast as I have been lately. If you don’t sometimes worry you’re going to pee yourself a little bit, you’re probably not pushing yourself hard enough.

What’s been the most interesting part of being a landlord so far?

The complex emotions that landlording engenders. You and your tenants both develop an attachment to the house, and this creates an unusual situation where two groups of people view the same house as “theirs.” They say the #1 rule of real estate is not to get emotionally attached, but that’s not always easy to stick to.

What’s a fact about yourself that people might be surprised by?

Although I’m a huge tech guy (I can see three different computers in my room as I write this), I refuse to make the transition to ebooks. I buy pretty much every book I read, and have amassed a massive (800+) collection of physical books. Ebooks might be more convenient, but when a girl comes over and checks out your bookshelves, is she really going to be impressed by your Kindle?

Before Castle, what was your proudest accomplishment?

In college, I co-wrote, produced, and directed a full-length original musical. In many ways it’s visibly a first, collegiate effort, but there where a few moments where Nat, my co-writer, and I really hit on something great.

If you could have any celebrity be your landlord, who would it be?

Taylor Swift. After I moved out, she’d write a song about how I was a bad tenant.

You can reach Max anytime at max@entercastle.com.

by Max

There’s a TV show on the air right now that can teach you everything you need to know about starting a company.

It’s not Shark Tank. It’s not Silicon Valley. It’s not even Restaurant Startup (featuring official Friend of Castle Banza!)

It’s Adventure Time1.

For those of you unfamiliar with Adventure Time, the cartoon follows the adventures (of course) of Finn, a boy who may or may not be the only human left alive, and Jake, a shapeshifting dog who’s also Finn’s adopted brother, as they journey through a post-apocalyptic magical world. But it’s so much more than that. Writing in the New Yorker a few months ago, TV critic Emily Nussbaum2 described Adventure Time as “one of the most philosophically risky and, often, emotionally affecting shows on TV.”

She didn’t mention all the startup lessons, but trust me—they’re in there too. Allow me to demonstrate:

Lesson #1: Be relentless.

Building a startup is an exercise in repeated failure. Fail, iterate, repeat, and so on, until eventually (hopefully) you succeed. The trick, basically, is just to not stop3.

Many of Adventure Time’s characters embody this lesson, from Finn and Jake’s relentless adventuring to Lumpy Space Princess’ relentless quest to go to Promcoming with Brad4. But none exhibit it better than the Ice King, the ineptly evil, socially awkward ruler of the Ice Kingdom.

The Ice King is relentless in his quest to marry a princess, whether by kidnapping one, brainwashing one, or even entering an epic Wizard Battle to win a kiss with one. Despite having no friends other than some penguins of unclear intelligence, the Ice King manages to stay upbeat about his situation5. It’s an example we can all learn from, even if our startups don’t (yet) involve kidnapping princesses6.

Lesson #2: Don’t get excited about a deal until you know all the details.

Whether it’s an investment round or a big partnership, I’ve seen so many startups get super excited about deals that turned out to not be so great once they read the fine print. (The classic example: raising a huge round [hooray!!] but giving away a huge percentage of your company [not so hooray…].)

Finn and Jake learn this lesson the hard way in the season one episode “Wizard.” They’re offered some magic powers by Bufo, a weird frog, but in their excitement about gaining sweet wizard powers, they don’t ask what Bufo demands from them in return.

Dustomancy—the power to control dust mites!

Holding up their end of the deal results in a lifetime of wizard enslavement—at least, until Finn formulates a winning escape plan. Because this is, after all, a kids’ show—albeit, an incredibly disturbing one.

Lesson #3: Not everything has a lesson.

How do nimble companies become sclerotic and bureaucratized7? Often, it starts like this: a mistake is made, a lesson is learned, that lesson is codified into a new rule or procedure. Rinse, wash, repeat, and a process that’s intended to eliminate mistakes ends up eliminating the very spontaneity that made you succeed in the first place.

While it’s important to learn from your mistakes, it’s equally important to recognize that not every failure has a lesson to teach. Luck is the perpetually under-credited component of success, and sometimes you fail despite doing everything right.

“Freak City,” my personal favorite episode of Adventure Time, makes this lesson hilariously explicit8. At the beginning of the episode, Finn is turned into a giant foot by a flamboyant douchebag known only as Magic Man, who refuses to change Finn back until he’s learned “a valuable life lesson.”

Foot-Finn becomes an outcast due to his freakish nature, but eventually—after an inexplicably auto-tuned musical interlude—he teams up with a bunch of other messed-up freaks to hunt down Magic Man. And after all that, it turns out the “lesson” Magic Man wanted them to learn was just that he, Magic Man, is a big jerk.

Some lesson, huh? But that’s how it goes: not every experience has a valuable life lesson to teach you. Sometimes, the best course of action is just to move on.

 
 

I watch Adventure Time almost every week, and with each new episode I’m more and more convinced that it’s one of the crowning artistic achievements of our era. And the business lessons? They’re not half-bad either.

1. Kind of gave it away there with the title, didn’t I? ↩
2. No relation, I swear. ↩
3. Paul Graham said that “you can get surprisingly far [in a startup] by just not giving up.” ↩
4. Most cartoon characters are known for their limited, repetitive behavior sets, so none of this is too surprising. ↩
5. That said, it’s not too hard to tell that he’s masking a deep, incurable sadness underneath. ↩
6. “The royalty abduction industry is ripe for disruption!” ↩
7. I’m normally a super good speller, but man, “bureaucratized” trips me up every time. Get it together bureaucratized! ↩
8. This episode also contains one of my all-time favorite Adventure Time quotes: “I’m not gonna cry, man, I just FEEL like crying!” ↩

Each week, we’ll be introducing you to a member of the Castle team. We’re starting this week with Tim Dingman, Castle’s operations guy and punk fanatic. Here’s a brief Q&A to provide you with a look into the Wild World of Tim:

What’s your favorite part about working at Castle?

The collaborative decision-making. Our team has established a formidable process for coming to conclusions about how we should run our business. I have experienced nothing even remotely like it.

What’s been the most interesting part of being a landlord so far?

Establishing the lease and accompanying house rules. Every property-landlord-tenant relationship is unique, and the lease and house rules must reflect or encapsulate the relationship. Those two documents lay the groundwork for everything that follows.

Before Castle, what was your proudest accomplishment?

Planning a conference called A Better World by Design. ABWxD is a student-run and student-led design conference held annually at Brown and the Rhode Island School of Design (RISD) in Providence. I was on the planning committee for the 2010 and 2011 conferences, a time of high growth and formalization for the event. In startup terms, we had moved from nailing it to scaling it.

What’s a fact about you that people might be surprised by?

I’m an Eagle Scout.

If you could have any celebrity be your landlord, who would it be?

Elon Musk. He could get our house solar panels through SolarCity and let us ride around in his prototype Teslas.

You can reach Tim anytime at tim@entercastle.com.

by Max

I hate, hate, hate, hate calling strangers on the phone.

I will go out of my way to avoid ordering a pizza1. I dread scheduling an appointment with my dentist more than I dread actually getting the cavity filled. Early on in my first job, my boss had me try making a sales call in front of him, and I got so nervous that I accidentally dialed 9112.

I’m not sure why I find calls so scary. I am not, in general, a shy person. I’m pretty capable of keeping even the most awkward conversation going3, and I truly love public speaking. But ask me to pick up the phone and cold-call a landlord, and I’m terrified.

It’s odd: the activity with the fewest potential consequences strikes the most fear in me.

And yet, if Castle is going to succeed, I’m going to have to pick up the phone and call people—lots of people. Too often, startups wall themselves off in VirtualWorld, writing code and reading articles about lifehacking, when what they really need to be doing is talking to customers (or potential customers). I’ve been trying to talk to at least one landlord a day, and almost every time I do, I gain more from that conversation than I do from the entire rest of the day’s work combined.

If this were a typical startup blog post, I’d conclude with a paragraph about how I got over this fear—“This one trick helped me conquer my fear of calling strangers,” or “How I became a growth hacker for my personal growth.”

But the truth is I’m nowhere near over this fear, although I’m slowly trying. Scott and I are spending a few hours cold-calling landlords every week, and having someone else egging me on helps keep me going in a way I can’t do by myself. It’s like how if a person is afraid of bridges, their therapist will sometimes make them walk over a bridge every day—if I just force myself to keep doing it, eventually it won’t bother me4.

This bridge actually does look pretty terrifying.

As conclusions go, “I’ll keep trying” is pretty weak. But that’s the conclusion I’ve got. And in a way, it’s more honest. Most fears aren’t ever really tackled. They’re just chipped away at, slowly, a little bit here and a little bit there, for as long as you can stand to keep at it.

1. Push for Pizza might help. ↩
2. I was on a speakerphone where you had to dial “9” for an outside line, and the number started with “1,” so this isn’t quite as outlandish as it sounds. ↩
3. As my many terrible OkCupid dates can attest. ↩
4. True fact: The New York Thruway Authority will actually chauffeur people over the Tappan Zee Bridge if they’re too afraid to drive themselves. ↩

by Max

Last Tuesday I left my previous job and began full-time work on Castle. The past few days have been exhilarating, confusing, terrifying, and even boring, sometimes all at once. Striking out on your own is a mixed bag, except the contents of the bag aren’t actually mixed, they’re just a single thing that seems different every time you look inside. On one hand, there’s no one telling you what to do. But on the other hand, there’s no one telling you what to do.

I’ve always chafed at adhering to imposed constraints on my life and time: in school I could never get over the fact that I was pounding out essays only because some random person1 was telling me to, and even in the jobs I’ve absolutely loved I’ve never completely gotten over the feeling that I was getting up every day and going to a place because, basically, someone else told me to. And so very few experiences can compare to the feeling I got on my first Castle morning, when I rubbed my eyes open and realized that the entirety of my day, and every day after that stretching limitlessly into the hazy future, was no one’s but my own.

But that freedom is also scary. I can seek advice from everyone in the world, but no one can definitely tell me that I’m doing the right thing, and by the time I find out that I’m not, it might be too late.

This is getting a little flowery. Let’s look at some specifics. On Friday, I2:

• Drafted a one-pager introducing Castle for circulation to potential investors.
• Coded the front-end templates for account creation in our MVP.
• Chatted with a Bay Area landlord who reached out to us via our website.

All of this seems like the right thing to do. Working on the product? Talking to potential customers? Preparing materials for investors? Check, check, and check. But I could’ve easily replaced the three items in that list with completely different ones, and still followed it with “All of this seems like the right thing to do.”

This is not to say that this makes me worried, exactly, but it does fill me with a sort of low-level vibration that’s not really worry, but not definitively not worry, either.

So here I am at the helm of a ship that might be pointed the wrong way, or cast adrift in the wrong ocean, or it might not be a ship at all, just a two-inch toy boat, and I might be nothing more than a little kid in the bath, pushing my toy boat across a sea of soap suds and imagining that I’m in charge.

And the only response I can have—the only response anyone can have—is “Onwards!”

1. A random person I was actually paying! ↩
2. My co-founders and I send daily update emails to a “Daily Updates” listserv at the end of every workday, outlining everything we accomplished that day. I’m not sure how scalable this will turn out to be, but so far it’s been a nice way to keep each other up-to-date and create a permanent record of what we’ve done when. ↩

by Tim

I think about punk a lot—at least once a day on average. Sometimes it’s a specific band, sometimes it’s the history of the genre, sometimes it’s my personal history with punk. Punk is a big part of who I am, and I reflect on the idea accordingly.

My mental connection between punk and startups came during Venture for America Training Camp in the summer of 2012. Each Fellow had to give an Ignite-style presentation about a topic of his or her own choosing. With my penchant for evangelizing punk at any appropriate opportunity, I had no trouble deciding on a general topic.

I knew I would have to cover the history of punk1 and my relationship with it, but I also wanted to cross the musical divide and connect with my (mostly non-punk) audience. By examining the traditions of punk, I found the right bridge: DIY.

DIY stands for “do it yourself,” perhaps the core principal of the punk ethos. From the beginning, punk has had a homemade quality to it; bands made their own logos, their own gig posters, and their own merch. Punk was partly a reaction to the corporate rock of the 70s, with overblown and overproduced bands like Kansas or REO Speedwagon spending millions on fancy things while producing material of little musical merit.

London punks showing off their DIY shirts, jackets, and hair.

Along with the DIY attitude comes a high degree of hustle and grit. Tales abound of bands like Black Flag and the Minutemen touring relentlessly, sleeping in their vans and jamming econo2. The bands often toiled in obscurity for years, but they produced some of the greatest (punk) albums ever recorded and have secured their place in history.

The entrepreneurs I know practice the same values. A few weeks ago, I watched VFA 2012 Fellow and Zest Tea founder James Fayal stuff and seal bags of tea at his house3 for several hours, a one-man assembly line for highly caffeinated teas. He then took those bags from Philadelphia to New York City, hauling trash bags of tea around Manhattan just so he could showcase his product for a couple hours at a VFA event that night.

Castle cofounders Scott Lowe (left) and Max Nussenbaum (right) help Zest Tea founder James Fayal (center) package tea.

Taken in the right light, punks look a lot like entrepreneurs. They share a core attitude of hard work, passion, and dedication. Swap out a band for a founding team, a genre for a market, and an album for a product, and you’ve made the jump seamlessly.

My presentation has since been lost to the sands of time, but I remember the message clearly: be a punk. Don’t be afraid to give the system the middle finger and to start something on your own. Do it yourself.

1. Briefly: proto-punk (Iggy Pop and The Stooges, MC5); punk (The Ramones, Sex Pistols, The Clash); post-punk (Gang of Four, Joy Division) and hardcore (Black Flag, Minor Threat); punk revival (Green Day, Rancid)↩
2. A term coined by the Minutemen, hardcore’s most eclectic and idiosyncratic act↩
3. Fittingly, James’s housemates are dedicated punk rockers ↩

by Scott

When you set out to build a web application today, you’re faced with a ton of choices. What are you running server-side? PHP? Ruby on Rails? Node?

How about client-side? You’re more constrained with what languages you’ll be using on the frontend, but how are you supposed to sort through all those frameworks? Bootstrap? Foundation? Angular? Ember? Backbone?

Regardless of your web app’s feature set, these are question you’ll likely ask yourself along the way.

It’s incredibly important to always use the right tool for the right job. That’s true in everything from construction and lawn care to sales and web development. Which tool is the right one for the job depends on what you’re optimizing for, and at Castle, we’re optimizing for speed because the faster we’re able to prototype, the sooner we can collect feedback. To that end, we’re currently building our backend on sails.js and our frontend on AngularJS and Twitter Bootstrap.

With sails.js you can build a production-ready backend1 in just a few hours by generating models and controllers for the stuff you’ll need to store from the frontend. AngularJS is a frontend JavaScript framework built by Google that connects your client-side JavaScript logic and data to your browser’s view. Using AngularJS and the open source angular-sails module, we can send data from the browser to the database (and vice-versa) with just a few lines of code. Plus, through socket.io, sails.js is able to broadcast database updates to other connected clients (ie, open browsers) which makes once complicated features like chat and real-time notifications a breeze.

That leaves you with one last big question: how will you style and arrange the data once it gets to the browser? Unsurprisingly, a quick search reveals a ton of options, but there’s no doubt who the current winner is.

Bootstrap 3 is an extremely popular mobile-first frontend framework that is most notable for its mobile-responsive grid system and pre-styled HTML elements (think headers, input boxes and buttons, for example). You won’t win any design awards for using Bootstrap and you’ll have to jump outside the framework for more advanced styling, but you’ll be able to build a decent-looking app without writing much code. Things get even better when you look for clever ways to integrate Bootstrap and Angular.

Because of the community support for these two frameworks, there exists an entire collection of common UI interactions built on top of them: UI Bootstrap. These elements render in the browser as user inputs and content, and when the user interacts with them, they inform Angular, which in turn tells the sails.js API, which then stores the data in the database and informs the other clients—all this with just a few lines of code.

When you step back and take a look at the whole system, you’re left with the guts of a styled, mobile-responsive, real-time web application. And since the frontend is completely separate from the backend2, rolling out a native mobile app is just a stone’s throw away. But we won’t know if that’s necessary until we get something in our users’ hands and hear what they have to say about it.

1. A RESTful JSON API, for the technically inclined reader.↩
2. You can run them off the same server early on to get things going, but remember that they’re completely separate units and should be treated as such.↩

by Max

One of my favorite startup stories ever is the legend of Mr. Macintosh. Apparently, one day Steve Jobs accosted the original Mac development team with a crazy idea: that they create a mysterious little cartoon man “Mr. Macintosh” who lived inside the computer. Once every few thousand times you pulled down a menu, you’d get Mr. Macintosh instead of the menu contents. He’d wave, wink at you, and then disappear. They were even going to plant subtle references to the legend of Mr. Macintosh in the manual, while officially denying his existence.

Mr. Macintosh. He kind of resembles Ringo in “Yellow Submarine”

Tragically, Mr. Macintosh never made it into a shipping product—he was a casualty of the original Mac’s very limited (128k!) memory. And yes, maybe the idea was a bit too far on the ridiculous side, especially in an era when most people weren’t familiar with how computers worked. (Imagine the incomprehensible tech support calls you’d get from mom—“Honey, the little man is in the computer again!”)

Still, what I love about Mr. Macintosh is the simple message he conveys: that the people who designed the original Mac were having fun doing it. It’s a message that’s missing from so much modern web design, in spite of—or perhaps because of—the last few years’ increased emphasis on pure beauty.

I mean, look at these homepages: they’re beautiful, sure, but do any of them make you smile?

To make a startup landing page, all you need is a crisp photo of a smiling person and/or an Apple device.

Basecamp (née 37signals) gets it. Look at this ridiculous drawing on their homepage:

And look at this goofy guy who guides you through the signup process:

Those drawings look like the page’s designer dashed them off in twenty minutes because he felt like his designs had too much whitespace—and that’s exactly what I love about them. When you look at a design like that, you can’t help but feel a personal connection to whoever made it.

Don’t get me wrong—I love Squarespace and Soylent and all the other big-photo-and-header-in-a-very-thin-typeface startups I pointed out above. But they’re like this generic male model I found on a stock photo site. Basecamp, meanwhile, is like Paul Rudd.

I spent WAY too long looking for the perfect picture of Paul Rudd for this article.

We’re only beginning to face design challenges at Castle, and it’s always easy to be an armchair critic. But as we venture out into the strange world that is web design in 2014, I hope we remember to keep our sense of whimsy. We’re just pushing pixels around on a computer screen. We can literally do anything. And that means we’re allowed to have fun.

by Tim

Back in middle school, a friend of mine introduced me to a game called Age of Empires. The two of us loved that game, sneaking down to his computer room in the middle of the night to play it whenever I slept over at his house. It’s probably my favorite game of all time.

For the uninitiated, Age of Empires1 is a real-time strategy game that puts you in control of a medieval civilization2 bent on world domination. Your job is to build a mighty empire and eliminate your enemy’s every last unit.

The cover art for the aformentioned classic RTS.

The game has three key mechanics: resource harvesting, technological advancement, and military conquest. The player uses villagers to gather resources, which the player can use to create more villagers, military units, and buildings. The player can also spend resources on researching new technologies, which improve current units and unlock new ones.

As a novice player, I focused on technological advancement, figuring it was important to always have better units than my opponents. As soon as I had enough resources, I would spend them on new technologies. I prided myself on always reaching the final technological stage—the Imperial Age—before anyone else.

As it turned out, my strategy earned me nothing but destruction. While I was spending all my resources on technologies, my opponents were building massive armies and invading my domain. Time and again, I witnessed their unending hordes destroy my few advanced units, killing my soldiers and pillaging my villages. What was I doing wrong?

After observing some more talented players in action, I saw that my priorities were exactly backwards. The best players spent all their resources on making more villagers, who could in turn harvest more resources3. Sure, they initially languished in the Dark Age, but by the time I was limping along the technological finish line of the Imperial Age, they had almost caught up and had a full army to boot. Once they did catch up, my advantage evaporated, leaving me defenseless in a sea of hostile knights and archers.

To put it in startup terms, the best players always put growth ahead of technology. By using their resources to harvest more resources, they harnessed the power of exponential growth. Even my best technologies could only double or triple resource extraction rates. As the plot below busily illustrates, the exponential curve blows away even the best linear trend.

Not the best-designed graphic, but it gets the point across.

At Castle, we’re doing the bare minimum to produce something workable—the so-called MVP. (Look for another blog post on the topic soon.) Instead, we’re focusing on growth, figuring out how we can acquire as many users as possible. As the Book of Paul notes, “The only essential thing is growth.”

1. To be specific, Age of Empires II: The Age of Kings (plus The Conquerors expansion pack).↩
2. I preferred the British for their Longbowmen, although the Japanese and their Samurai were also top-notch.↩
3. The tragedy of the commons is on full display in Age of Empires. A game that drags on long enough leaves the entire map devoid of any trees, mines, berries, or livestock.↩

by Max

Ever since we first decided to build software for landlords, we’ve had lots of ideas about what form Castle could take. And I mean lots of ideas. This presented us with a problem: how could we figure out which of our ideas were things landlords actually wanted?

Of course, we’ve been talking to as many landlords as we can, but that kind of data can only take us so far. For one thing, the landlords we know are far from a representative sample of the overall market. Furthermore, there’s a big difference between someone saying they’d use your product and someone actually signing up to use your product.

It’s easy for someone to say they’re interested in what you’re building (especially if they’re saying it to you directly, where they might feel pressured to sugarcoat their true feelings). But talk is cheap: what we needed was action.

Getting Some Action

When a customer starts using a web service, they actually go through two distinct phases:

1. Signing up to use the service
2. Actually using the service

Our key insight was that we didn’t actually need to build the product to get customers to sign up. We just needed to build landing pages.

Ultimately, we settled on three different ideas we wanted to test, each based on a problem we’d heard about from talking to landlords:

1. A customer support system for landlords (problem: bad tenants)
2. Online rent payment (problem: rent collection)
3. An image-based repair reporting system (problem: maintenance)

We quickly mapped out a slogan and three main features for each idea. Then, we built landing pages for each of them. We used LaunchRock, a quick graphical landing page builder. I was crying inside because the landing pages were so ugly, but hey—this was just a quick test.

One of our test landing pages. Note the clever rebrand.

Each landing page advertised the product, and prompted visitors to sign up by entering their email address. And signing up was actually the only thing they could do. Once they did, they were told that “Palace” wasn’t quite ready yet, and that they’d receive an email once it was.

Of course, these landing pages were useless without people to actually visit them. So we quickly whipped up some copy and bought some AdWords and Facebook ads for all three landing pages. Then we let them run for a week.

One of our hastily-made Facebook ads

A Perfect Experiment? Not Quite…

It’s not like we’re just going to build whichever landing page got the most signups (spoiler alert: I’m saving which one it was for a future post). The results of a test like this are far from conclusive. It could be that one page got more signups because our ad was better written, or better targeted. It could be that one page got more signups because people liked the icons we chose better.

Or it could be something trickier—maybe a product that’s simpler to explain (rent) gets more signups than the one that’s more complicated (online property manager), even though the more complicated one is actually the better product.

The Big Picture

As startup guys, we love building stuff. Personally, nothing makes me more excited than that moment you first sit down to make something1—whether it’s a product, a piece of art, or a house.

But one of the biggest mistakes we see other entrepreneurs make is getting so excited about making something that they don’t take enough time to figure out whether or not what they’re making is something people actually want. If we can get 20% of the feedback we’d get from actually making something with .0001% of effort it would take to actually make it, we’ll take that deal.

1. At least, nothing that’s appropriate for this blog. ↩

by Tim

If you’re at all familiar with startups, you probably recognize the name Paul Graham. In his collection of essays—also known as the Book of Paul—there is a tract entitled “Do Things That Don’t Scale.” In it, the former head of Y Combinator regales the reader with tales of successful startups doing menial and mundane work to ensure the success of their product. (Stop now and read his essay if you haven’t already. It’s OK, I’ll wait.)

At Castle, the most important step we can take now is to nail our customer research. The fruits of such labor will yield the seed of our MVP. Once we have a product, we’ll be able to iterate our way to success.

We already know our initial customer is small, independent landlords. But how do we reach them? Since we want to survey them, email is the natural choice. The question is, where does one find landlord emails?

The best answer we’ve found so far is “off campus housing boards.” Many colleges facilitate their students’ search for off campus housing by providing sites on which landlords can post rental listings. Most of the time, the listings include an email address.

Once we knew where to look, all we had to do was gather the relevant information. We grabbed our laptops, held our breath, and took a deep dive into the world of off campus rental listings. Sunday slowly passed us by as we sat staring at our screens, furiously highlighting, copying, and pasting names and email addresses. Comfort, nice weather, and personal hygiene took a backseat for seven hours while we jumped from board to board, looking for new landlords to interrogate.

So far, it’s worked. We’re closing in on 100 survey responses, with each response bringing us closer to the right MVP.

Startup culture places a heavy emphasis on grind, which I’ve always understood academically. Having put in my first day of grind, I can say this with certainty: I’m ready for more.

by Max

Today, we’re introducing Castle to the world—except right now, Castle is nothing more than a bare-bones landing page and this blog. If Castle is our child, this isn’t the birth, or even the conception—it’s the moment the parents first saw each other across the room. (Or, as may be more fitting for a tech startup, the moment they were first matched on Tinder.)

So, why are we starting our company blog before we even have a product? The decision goes back to something Dave Tisch (at the time, the Managing Director of Techstars NYC) said to me when I was a fresh-faced college grad first dipping my toes into the waters of Startup Land back at Venture for America Training Camp in the summer of 2012.

Castle Co-Founders Max and Tim (and a bunch of other people) soaking in Dave Tisch’s wisdom

Dave explained that there were four main factors Techstars considered when deciding whether or not to invest in a company: the team, the market, the product, and the idea—in that order.

The team is the most important factor. A strong team can overcome a lot of other weaknesses, but not even the greatest idea in the world will save a team that can’t execute.

The market is the second-most important. No matter how awesome your company is, it won’t succeed if the potential audience for what you’re making doesn’t exist.

Then comes the product—the thing you’ve actually made—and then, lastly, there’s the idea: the concept that provided the starting point for the product.

Another way to think of it is, which of these factors is the easiest to change? If you’ve got a killer team, you can discover that your first product isn’t really working and switch1 to a different one. But changing your founding team, especially near the beginning, is much, much harder.

At Castle, we’ve put together an amazing team (we’ll be introducing ourselves in a future post), and we’re confident in our market: small, independent landlords2. And we’re working on our product now—first, by interviewing landlords in our target market so that we can make sure we’re solving real problems.

The Castle team. From left: Scott Lowe, Max Nussenbaum, Tim Dingman, and Griffin Wagner

But we don’t want to wait until Castle is released to start sharing what will no doubt be a strange and difficult journey with you. We also want to be brutally honest about the challenges we encounter as we get this company off the ground—and those challenges start way before the product is done.

We’ll have a lot more to share with you in the coming weeks. In the meantime, you can always reach us at team@entercastle.com.

Thanks for joining us. The adventure begins!

P.S. Interested in email updates and early access to our super awesome secret beta? Sign up here. We promise not to bother you with useless crap.

1. I refuse to say pivot. ↩
2. In fact, three members of the founding team—myself, Scott Lowe, and Tim Dingman—will soon be landlords ourselves, through our side project Rebirth Realty. ↩