Courtland Allen: Q&A Session

Q&A Session: Courtland Allen

Courtland Allen Q&A Session is happening on August 15th, 2019 at 10:00 AM PST (1:00 PM EST)

Courtland Allen is a software engineer, designer, podcast host, MIT graduate, and Y Combinator alum. In 2016, he created, a community.

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Courtland Allen – Transcript

Q&A Session with Courtland Allen @ IndieHackers

August 15th, 2019

What inspires you?

I’m inspired by people who are accomplishing the things I dream of accomplishing and doing it in a way that I think is eventually achievable for me. In fact, I’d guess that’s the formula for pretty much everyone to be inspired. (I think about inspiration a lot because the purpose of Indie Hackers is really to inspire lots of people to start their own businesses.)My #1 focus right now is growing Indie Hackers. I want to create a social network that actually makes people more productive, not less, and I want it to be roughly 100x bigger than it currently is without sacrificing on quality. That’s a tall order. I’m heavily inspired by others who’ve built great communities and social networks. Things like Twitter, Reddit, and even Facebook. I don’t want to build a clone of any of these sites, but I think a lot about what makes them work at the core level, so I can apply those principles and do some good with Indie Hackers. In my personal life, I’m heavily inspired by anime and fiction writing in general. I just love good storytelling. Hopefully, I’ll write some great fiction myself in the next decade or two…

Any advice you have for folks with the marketing skillset but not a dev skill set? Partnering?

The marketing skillset is the best! We’re moving toward a world where building products is becoming easier, but marketing and growing them is becoming harder. Let’s start with the building. There’s a wealth of “no-code” tools that you can use to put an app or a project together without learning anything about software engineering. My recommendation is to start with, easily the best resource for discovering these tools, seeing what they can do, and learning how to use them. They’re only becoming more powerful over time, and there’s a ton you can do without ever having to partner with a developer! As for marketing, there’s more competition today, because it’s so easy to put a product on the market. The result is that people are struggling with growth. If you can prove you’re good at it, you’re worth your weight in gold. The challenge here is that it’s harder to prove you have marketing skills than it is to prove that you have “hard” skills like engineering. A resume isn’t enough. The proof is in the pudding, as they say. I recommend building something simple, growing/marketing it, and then writing about how you grew it. And by “building,” I mean you can really do anything! Even a blog counts as building something. Indie Hackers itself started as simply a blog. Another example is, which is a newly-popular resource that’s also essentially just a blog. If I’m a developer considering whether to partner with a marketer, I want to see that they’ve actually taken the initiative to grow something and done a good job at it, just as you’d want to see that I’ve taken the initiative to build something and can actually do it. After that, it should be easy to partner up if you simply put the word out that you’d like to. In fact, at that point, I’d recommend being picky and reaching out to individual developers whose work you think highly of.

What marketing blogs do you read and podcasts you listen to regularly?

I don’t read any marketing blogs regularly, but I do read sporadically. I like to do a lot of just-in-time reading about a topic once I reach a point with one of my own projects where I need to learn a lot more about that topic. For example, I’m working on growing a new groups feature on Indie Hackers, so I’ve recently spent some time going back and listening to old podcasts and reading old posts about how the founders of Reddit first launched and grew their subreddits feature. I’m also working to grow the Indie Hackers mailing list, so I had Sam Parr from The Hustle (1.5M email subscribers, 8 figures in revenue) on my podcast to talk about it, and now he’s an acquaintance who I can ping and ask for specific tips. Marketing is less of a full-time job for me, I suppose, so I don’t need to broadly stay up-to-date with what’s going on in the industry. Rather, marketing is a crucial skill in my full-time job, so I do need to become good at doing very specific things when the time is right.

What are some common productivity traits that you’ve seen among successful start-up founders?

There are lots of smaller tricks and tips that I’ve seen, but they vary so much from person to person that I don’t think they’re worth sharing with a broad audience. There are two big things, however, that I think are universal:1. Enjoying the day-to-day tasks.
2. Being excited about the overall mission — the ultimate goal. Many founders have neither of these. Many founders have one but not the other. But ideally, you have both. Enjoying the day-to-day tasks is like being a painter who starts a painting business. You get to do what you love every day! This is crucial. We’ve all heard the cliche that it’s about the journey, not the destination, and it’s very true. Even if your startup succeeds and you accomplish your goal, that’ll only be you temporary happiness before you acclimate. So it’s important to actually enjoy the whole journey all the way there. You don’t want to be miserable for 7 years just to get 6 months of happiness. There are some good tricks for this, too. Any business is going to involve some drudge work that you “should” do but don’t particularly enjoy. What I’ve noticed a lot of founders doing is simply ignoring these tasks, de-prioritizing them, or outsourcing them. Sure, there are consequences. Their businesses might grow a bit more slowly, for example. But they’re much happier as founders, and thus they’re better founders. Doing this requires a lot of mindfulness. If you’re not actively thinking about it, it’s easy for the drudge work to pile up, and before you know it, you’re almost never doing what you love on a day-to-day basis. The second factor is just as important: having an overall mission. You’re going to have bad days, guaranteed. Sometimes you’ll have bad weeks, or even bad months, where the day-to-day just isn’t great. What keeps you going in those times is caring about the bigger picture. It doesn’t have to be something cheesy. It doesn’t even have to be selfless. “I want to become financially independent so I can work for myself on whatever I want, whenever I want,” is a totally fine mission! In fact, I think it’s one of the best missions to start with. It’s the one I started with. Your mission can evolve over time. Your mission is also what inspires others when you tell them about what you’re doing. It will inspire employees to join you, customers to buy from you, friends to cheer you on, investors to invest in you — everything. And we’re social animals to the bone, so as a founder you’ll feed off the energy that others put out when you tell them about what you’re doing and why you’re doing it. It’s totally underrated. If you want to stay motivated, make sure you know why you’re doing what you’re doing!

Can you share how you marketed and launched IH in the early days? You have talked about seeding with dummy accounts on other podcasts before, and that’s one tactic. But I’m hoping for more…what channels did you tap into that worked for you?

Indie Hackers started off as a blog where I interviewed founders about their side projects and businesses. I went from idea to launch in about 3 weeks, and the interviews were specifically tailored to appeal to the channel that I launched on: Hacker News. By reading hundreds of posts in the HN community, I learned that HNers cared about things like bootstrapping, software engineering, side projects, financial transparency, and tactical advice, so I made sure to bake that into my interviews. For example, everyone I interviewed had to share their revenue numbers. About 90% of the people I reached out to said no because of that requirement, but I stuck to it. As a result of this and other decisions, the site did very well on Hacker News on launch day and stayed at the top for a full 24 hours. I got about 100,000 page views on my first weekend after launch. I used those page views to build up a mailing list. About 1000 people subscribed in the first week, and I began sending them weekly emails with links to new interviews, and a short blurb about my own story and progress. The mailing list continued to grow and served as a crucial channel for me to drive repeat traffic and avoid the dreaded trough of sorrow. When I built the forum about a month later, I seeded it with dummy accounts and had some fake conversations with myself, but the newsletter was really the key, as I had thousands of people I could email with links to these fake conversations. People began joining and conversing with me and eventually with each other. Communities are amazing for growth. When people talk to each other, you can really scale things. You can get out of the way (somewhat) and there’s still value being created without you. The Indie Hackers forum spawned real-life meetups, which I tweeted about recently[0]. Today we have about 60 meetups a month, all over the world, and all run independently. I play no role whatsoever in organizing these events, paying for them, etc. The community also fuels a number of features on the website, including our directory of products[1] and our milestone posts[2], which in turn power our milestone newsletter and provide a source of guests for the podcast and authors for our content. I’m a huge fan of building your own internal distribution channels rather than relying on external platforms.

What can you tell us about how your company was acquired by Stripe?

It’s a surprisingly short story! I got an email completely out of the blue from Patrick Collison, who asked if I’d be open to selling the company to Stripe. One brunch later, he sent me a formal acquisition offer. It was one of those rare win-win-win situations where the deal was great for me, great for Stripe, and great for IH members and readers. I’ve always been frustrated when my favorite products disappear or get worse after being acquired, but the exact opposite happened with Indie Hackers, and it wasn’t an accident. The incentives were perfectly aligned all around, which is the key. In addition, the team at Stripe has been extremely helpful while also being just the right amount of hands-off. Couldn’t have joined a better company.

For companies considering podcasting as part of their marketing efforts, what advice would you give? (Asking because I hear folks throwing that idea around all the time without a clear idea of WHY podcasting is right for their business, and I’m never sure what the “right” answer to that question should sound like).

First, podcasting is a slog. It’s a huge time investment, not just up front, but ongoing, and it takes forever to gain meaningful traction. The vast majority of podcasters quit before they reach 10 episodes, so you need to be prepared for the long haul if you’re serious about it. Second, for many businesses podcasting will never pay off, even if your show gets traction. You need to do the math beforehand to understand if it’ll be worth it for you. I think you are spot in with your question — companies need to ask WHY they’re doing a podcast before they get started. For Indie Hackers, my goal is to inspire people, to change hearts and minds. Podcasts are an amazing channel for doing that. You’re literally in someone’s ear for an hour or more, speaking directly to them, while they give you their full undivided attention. Compare to email or blog posts, where people are usually distracted on their computers and on the way to do doing other tasks. Compare to giving a talk at a conference, where people are typing away on their phones, where most of them came to see other people who aren’t you, and where you can generally only reach a few hundred people rather than the tens of thousands who can download a podcast. Engagement is huge for me, and podcasts are amazing at engagement. Another good example is the Art of Product podcast run by Ben Orenstein and Derrick Reimer. They’re simply sharing the story behind how they’re building their business. Storytelling is huge. Listeners really get to know them and their struggles and successes, and many hundreds of listeners have become paying beta customers of Ben’s product, Tuple. He hasn’t even launched the product yet! If you’re an early-stage company for whom hundreds of customers is a meaningful number… or if your product has a high price point where even just a few sales can justify the ongoing time and monetary costs of producing a podcast… or if it’s important for you to get a message out to the world in an engaging way… or if you want an easy way to meet impressive people and connect with them as guests… or if you simply love podcasting for some other reason regardless of the costs, go for it! Otherwise, I’d say you should put more thought into it because you’re more likely to quit than stick with it.

As a developer, I often focus too much on the product and not enough on sharing it with the world. How would you go about building a community around your product/service early on? Could you also share some early-stage growth hacks you recommend for indie hackers?

As for focusing too much on the product, it’s the most common thing in the world for developers to do that. I did that for years. I even did it for Indie Hackers. I’ve probably spent 20-100x longer coding the product itself than is really justified. What worked for me was to simply realize this about myself and put some safeguards in place. I’m a developer, I love coding, and I’m not going to be able to control my impulse to code. So instead of assuming that I would magically become disciplined and responsible in this area. I simply chose an idea with a very small coding footprint. Indie Hackers was a blog. Even if I spent way too much time coding it, it would take weeks, not months or years. I actually said no to a couple of alternative ideas that I liked more than Indie Hackers because they were too code intensive and I was afraid of getting sucked in. You can do the same! Start small, start simple. Do not be ambitious with your product early on. I talked to Chad Pytel on the podcast, the CEO of thoughtbot. They’ve built many hundreds of products for themselves and for clients. When building for clients. their #1 recommendation is, “Hey, you don’t need 90% of these features you think you need for launch.” But when building apps on their own, they find themselves falling into the same trap, and building way too many features that they’ve convinced themselves are crucial. It’s a very difficult gravitational field to resist, so my advice is to avoid it altogether. As for building a community, build in public! No matter what you’re working on, share the behind-the-scenes about it. What decisions are you making, why, and how? What are your overall goals? What are your opinions? What do you need help with? Put that all out into the world at a high frequency, tweak your approach in response to feedback, connect with the people who interact with you, and don’t stop doing this. Easier said than done, of course. But I find the challenge is still more about making the decision to do this than it is about any particular difficulty in doing it. Most people simply choose not to do it.

What piece of advice would you give on launching a subscription-based online community? What do you see as the biggest challenge?

I don’t have a ton of experience here, as Indie Hackers has always been free to join. But drawing from a broader set of business experience and theory here, I’d say all the same rules apply! For example, charging businesses is usually easier than charging consumers, because businesses tend to have a lot more earning potential than consumers, and thus there are more things for them to buy that they see as increasing their earnings. For example, a lot of the best communities are actually just conferences or events, and I’d guess the majority of conference revenue comes from businesses paying to send their employees. The biggest challenge will depend entirely on what kind of community you want to start. At the very basic level, you need to get the community actually works. Most communities simply don’t work, because (1) they aren’t based around a shared activity that people actually want to commune around, (2) the creator doesn’t hustle enough to do the hard manual work of making it a valuable place early on, or (3) there are strategic missteps early on that usually involve creating the wrong type of space for the shared community activity, e.g. meeting too frequently, or in too big of a space, or on the wrong platform, or with the wrong agenda or format, etc. Also, if you want to make money from the community, I’d heavily recommend trying to make money from day #1. Otherwise, you’re likely to get into the habit of doing things that work to grow the community but that nevertheless aren’t actually valuable enough for members to pay for. You’re probably better off figuring out what’s valuable as early as possible, then focusing your efforts around that particular activity.

 I was wondering if you can share your best techniques to grow a user community for niche areas, for e.g. kids education resources K to 12.

Well, one of my biggest growth tips is to be niche, so you’re off to a great start! When you’re sufficiently niche, you can appeal to specific needs and desires that other communities and resources are neglecting. The result is that you can more easily create something 10x better for your audience than any of their alternative options. It’s not easy, of course. You really have to put in the time to find out what your niche cares about and likes, what resources they already spend their time and money on, and what those resources are lacking. But once you do that, you have a serious advantage over others. As for growth, start small! A community of literally any size can work well, so long as the shared experience between members is also of the right size. If you only have 5 members, for example, then it’d feel empty if you tried to meet up inside a massive venue as opposed to a small room. It’d feel dead if you tried to maintain an ongoing conversation as opposed to a once-a-month conversation. Etc. Keep the container small and the frequency rare, and only grow it as your community grows in size. Finally, you have to do the work yourself. You can’t automate it. You can use mass marketing. You have to use sales. Develop one-on-one relationships with your early members. Invite them personally. Prompt them with questions. Connect them to each other. Add value. And keep doing this for as long as possible, until your community is so big that your individual contribution is meaningless compared to scaling things. It might take years to get there, btw.

My question is about the early days of the Indie Hacker forum.1. How many subscribers did you have when it launched?
2. The majority of forums slowly shrivel. How confident were you that you had enough momentum for it to work?
3. When the forum launched how did you market it? I imagine a lot were being pulled indirectly after reading interviews?
4. What were the biggest lessons you learned / anything you’d do differently?

1. I launched the forum on Sep 8th, 2016, at which point I had about 1250 mailing list subscribers. Scroll down on the timeline here[0] for more detailed stats and information. 2. I had practically zero confidence. I was pretty sure the forum would fail. But it was a big part of what I wanted Indie Hackers to be, so I had to try. 3. I marketed the forum exclusively via the mailing list. Every Thursday my email went out with three sections: (1) a couple of paragraphs about how IH was doing and what I was working on, (2) links to the past week’s new interviews, and (3) links to the best conversations on the forum. The forum links didn’t get many clicks, but then again the forum was tiny, so even a few dozen clicks were good enough. 4. I probably could’ve done more to market the forum to grow faster early on. AMAs, etc. Patience was key. I’m glad I stuck with it. Many people give up after just a few months. Participation was also key. Forums don’t grow themselves. You have to be the #1 best member for many months and not worry about how that looks. Just because huge community sites appear self-sustaining doesn’t mean you should focus on appearing that way in the early days.


What are your thoughts on PR firms and when should a company adopt one?

Honestly, I don’t have anything intelligent to say on this topic! But my bias is toward doing your own PR when you’re small. You can spend your money in better ways, and it’s not that hard a skill to learn if you put in the effort. I’ve heard of some really big PR firm wins occasionally, but those were almost exclusively from very well-funded companies who had money to blow.

I’ve been in the unfortunate circumstance of having really bold copies of my Indie business done (like literally, they said to me in a conversation: I want to do what you’re doing but make it cheaper) – which makes me really hesitant to share numbers. Am I crazy?

That happens a lot. I’ve gotten that a lot, too. Sharing your revenue numbers is a totally personal decision. It’s free information for competitors, and it may even inspire some people to copy you. However, from what I’ve seen in the past 3 years, 95% of the time none of the above happens. And when it does happen, most of the time those competitors are fairly incompetent and nothing to worry about. The most formidable founders feel bad about blatantly ripping off other companies, except when you start to get into the $10M+ range, at which point venture capitalists will start to fund competitors. Competitive risk is usually fairly baked into the market. Depending on what you’re building, you may or may not face it regardless of what you share publicly. Your best bet is usually just to avoid winner-take-all markets (unless you’re the winner) and avoid markets where everyone competes on costs and drives margins down to near-zero. Alternatively, you can do things like build brand loyalty or stay ahead of the competition, etc. TL;DR, no you’re not crazy + you’re likely worrying too much + you need to evaluate the realities of your market realistically whether you share numbers or not.

What’s your process for finding podcast guests? What steps do you take to prepare for a podcast? Thanks!

I’ve got a massive list that I keep updated based on incoming requests and recommendations and based on my own ideas and people I research or hear about. When I’ve got open slots coming up, I reach out to someone on this list based on a set of criteria that matches my latest feelings on what would make for a good podcast episode. Then I reach out via email or Twitter DMs and hope they say yes! As for preparation, I’ll usually listen to another podcast or two that they were on, engage with some of their tweets or writing, and come up with a list of 20+ questions to ask. For some reason I find this task incredibly boring before I start it, so I procrastinate a lot, and often do it at the last minute. But once I get started doing it, it’s actually quite fun and rewarding, and my questions are significantly better when I spend more time working on them.

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