Season 2 Episode 6 Sep 16, 2020

How to be an Entrepreneur


Entrepreneurship is a road paved with failure and hardships, but you'll learn a lot in the process, and the rewards can be great.


In this episode, we talk about entrepreneurship with Courtland Allan, founder of Indie Hackers and host of the Indie Hackers podcast, and Kelly Vaughn, CEO and founder of The Taproom, and co-host of the Ladybug podcast.


Jess Lee

Forem - Co-founder

Jess Lee is co-founder of DEV.

Ben Halpern

Forem - Co-founder

Ben Halpern is co-founder and webmaster of DEV/Forem.


Courtland Allen

Courtland Allen is the founder of Indie Hackers and host of the Indie Hackers podcast.

Kelly Vaughn

Kelly Vaughn is the CEO and founder of The Taproom, a Shopify Plus agency rooted in Atlanta. Kelly and her team have helped hundreds of Shopify merchants build successful marketing strategies; map out customer journeys that convert; and provide the insight, experience, and tools businesses need to keep growing.

Show Notes

Audio file size







[00:00:01] JL: This season of DevDiscuss is sponsored by Heroku. Heroku is a platform that enables developers to build, run, and operate applications entirely in the cloud. It streamlines development, allowing you to focus on your code, not your infrastructure. Also, you’re not locked into the service. So why not start building your apps today with Heroku?


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[00:00:48] BH: Smallstep is an open source security company offering single sign-on SSH. Want to learn more about Zero Trust Security and perimeter list user access? Head over to the Smallstep Organization page on Dev to read a series about Zero Trust SSH access using certificates. Learn more and follow Smallstep on




[00:01:11] CA: I mean, I think the path is paved with failure and hardships, and yeah, there’s some people who just knock it out of the park on their first try, but it wasn’t like that for me. And I think the silver lining to that dark gray cloud is that I learned a lot in the process.

[00:01:36] BH: Welcome to DevDiscuss, the show where we cover the burning topics that impact all our lives as developers. I’m Ben Halpern, a co-founders of Dev.


[00:01:44] JL: And I’m Jess Lee, also a co-founder of Dev. Today, we’re talking about entrepreneurship with Courtland Allen, Founder of Indie Hackers and host of the Indie Hackers Podcast, and Kelly Vaughn, CEO and the Founder of The Taproom and cohost of the Ladybug Podcast. Thank you both so much for joining us.


[00:01:59] CA: Thanks for having us.


[00:02:00] KV: Thanks for having us.


[00:02:01] BH: Courtland, let’s start with you. Can you tell us a little bit about your background?


[00:02:06] CA: Yeah. So I am a full stack software engineer and designer. I got a degree in computer science from MIT and then moved out to San Francisco to live the startup life. I always wanted to start a company as a kid. Bill Gates was kind of my role model. I was a huge nerd and I spent a ton of time starting companies and not really succeeding, but for me there wasn’t really any other option besides trying to start something. I really didn’t want to work for the man, so to speak. And in 2016, I created Indie Hackers and that’s what I’ve been working on ever since.


[00:02:38] JL: Can you tell us what Indie Hackers is and what kind of projects you’re currently working on?


[00:02:42] CA: Indie Hackers is a community of developers who all have the same kind of itch that I had. They don’t really want to work full time jobs for other people. They would rather have the freedom that comes from running their own online businesses, and that’s easier to do today than it ever was before. And so the people on Indie Hackers are seeking some form of income independence where they can make their own money without limit, some sort of time independence where they can work their own hours or work from wherever they want. And to that end, they’re building all sorts of really cool, interesting products. And so on the community, you could find tens of thousands of different Indie Hackers asking each other questions and sharing tips and advice. And then on the podcast and also in our email newsletter, we interview some of the standouts among Indie Hackers and ask them how much money they’re making, how they come up with their idea, how they got their first customers and pretty much the entire journey from beginning to end of different projects and companies that they’re building to support their lives.


[00:03:38] BH: Kelly, how about you? Introduce yourself.


[00:03:42] KV: So my entrepreneurial journey started pretty young. I’m a front end developer who dabbles occasionally in the back end. I spend less time coding these days than I would like, but that’s, I guess, part of my job now, but I started building websites when I was 11. And I had my first freelance client when I was 14 years old. I was paid a T-shirt, not a good deal, but it kind of grew from there. I continued to get more experiences I was freelancing and I actually went in a completely different direction for undergrad and grad school. I have my bachelor’s in psychology and I’ve got two master’s degrees in public health and clinical social work. But I was still freelancing during that time. And in 2015, I decided that I didn’t want to work for anybody else anymore. I lasted eight months in a “real job” and I went full time freelance in September 2015. And since then, I kind of grew my freelance business to the point where I’ve started having employees and I officially rebranded to The Taproom in October 2017 and I now am running a team of 13. So we are a Shopify Plus agency specializing in custom development solutions for high growth merchants.


[00:04:57] JL: You mentioned that you don’t code as much anymore, and I also don’t code anymore. Courtland, I’m curious, how much development you’re doing these days?


[00:05:05] CA: I do code luckily, but not as much as I would like to. I just have to wear a lot of hats, including running the podcast and doing all sorts of non-code related things. But I’ve got to say that coding is one of the most fun parts of my job when I get to do it. And from other developers that I’ve talked to. So Stripe bought Indie Hackers in 2017 and Stripe is like a 2000-plus person company. And even Patrick, the CEO, will every now and then get to code and say that’s one of his favorite parts of his job. So I don’t know if that’s a desire that really leaves you.


[00:05:34] KV: Yeah. I completely agree with that. I don’t think I’ll ever completely leave the code altogether. I think most of my time at this point is facilitating my developers to make sure that they know how to do what they need to do, help them problem solve, but I’m spending less time, like I don’t own projects at this point anymore. I just said, “I don’t have the time to dedicate to sitting down and encoding for weeks at a time to build out a store for a client.” So I have to pick and choose what I work on at this point.


[00:06:01] BH: Yeah. Sometimes I can’t tell if I’m like missing the freedom to be able to get more heads down, coding time than I’m getting now or if I forget that when you’re doing software development and you also don’t have full control over the project, you don’t necessarily have the same freedoms and there’s sort of a give and take. So when I am coding, I feel like I get to have the privileged position that like being the boss or being the entrepreneur, you get to kind of make choices as you go and you don’t have to run them by anybody. A lot of the time when you’re doing the coding, you don’t get that benefit. You don’t get to kind of make some high level choices as you go.


[00:06:42] KV: Yeah. I completely agree.


[00:06:43] CA: One of the interesting things that I see with Indie Hackers is that because these companies are mostly started by software engineers and software engineers usually love to code, it’s hard for them to exercise that power, to make that choice. What I mean by that is they mostly just choose to code and not to wear the other hats that you probably need to wear as a founder, not to do the marketing and the sales kind of stuff and talking to customers, and that’s an easy way, except in some rare cases to not really succeed. So I think it’s great to have that choice, but also you got to have the self-discipline to choose correctly.


[00:07:15] KV: I think there’s a lot of pressure from entrepreneurs or other leaders talking about working on the business versus working in the business and development where it can be seen as working in the business where people will say it’s not the best use of your time, but I honestly think there’s a nice balance there of still getting to dig into the code and do some of that hands-on work, because this is a company that you created, you’re really proud of the success of that company and you’re continuing to be involved in the everyday work. I don’t know, for me, it kind of helps drive that success even further.


[00:07:49] CA: Yeah, I agree. And I think if you’re going to create your own company where you’re the one who sets the rules, it would be a tragedy if you create a company where you can’t do some of your favorite things.


[00:07:57] KV: Exactly.


[00:07:58] JL: So Courtland, you mentioned starting multiple startups before Indie Hackers. I’m curious how you came up with so many previous ideas and what it was like having gone through multiple startups.


[00:08:11] CA: I think I worked on four or five different businesses before Indie Hackers. And most of them were related to either productivity or email or combination of the two. And I think I just kind of fell into the ideas in a very unconsidered way. It’s like an idea pops into your head. You get excited about it. You tell your friends and your family about it and they want to see you succeed. So they’re happy for you. And then you find other people to work on it with you. And you’re all like kind of blindly optimistic that this is going to work, or at least that’s how it felt for me the first five or six years working on startups. So for example, the very first thing I worked on was called Sifter. And this is an idea that I had my senior year of college where I thought, “Gmail has got all these different filters.” You can say, “If I get an email from Jess, then send it to this label. If I get an email from Ben and archive it.” Or something like that. But I wanted to add like a bunch of more complex filters to Gmail. So I can say, “Oh, this email has attachments over a hundred megabytes and send me a text message.” It’s kind of like Zapier, but only for Gmail. I thought that will be a great idea. And I spent like a year of my life working on it and it didn’t have any sort of plan for how we’re going to make money or how people are going to find out about it. I got really lucky. And Google wrote about it in their blog post announcing the Gmail API, and we got a ton of traffic, but then we ran out of money. We had like $50,000 in funding that we got from this business plan competition. And we didn’t charge anybody any money for it. And so like the startup was dead and that was it. And that was like my very first experience in the startup world and the lesson I took away from that was, “You probably should make money somehow.” That was in 2009, back before it was cool to make money. Stripe didn’t exist. All the biggest startups are like Twitter and Facebook and they’re all loudly preaching the gospel of don’t charge money. The only voices in the room saying that you should make money from your startups are basically Jason Fried and DHH over at 37signals. And so I think that experience has kind of tinged my entire startup journey. All the ideas I had after that were some form of task management and your inbox or something related to email. But the second the Stripe beta was out in 2011, I put a price tag on my product and like watch people pay for it, and I was sort of hooked. And I think that paved the way for me to start Indie Hackers, which is sort of the antithesis of the typical VC mindset. Everybody on Indie Hackers charges money for what they’re building. Everybody plans to generate revenue. No one’s really going for a billion-dollar business. More people are just content to try to build sort of a regular business, but on the internet.


[00:10:37] JL: Kelly, have you started other businesses in the past?


[00:10:41] KV: I have. I have started many in business. My friends joke that I collect LLCs for a living because I just kept on creating more business.


[00:10:49] JL: Since you’re 14, right?


[00:10:50] KV: Yes, exactly. I have a book that I’m selling. I have a Shopify store selling merch. I have two podcasts now. I have the Ladybug Podcast and I have a commerce-related podcast called Commerce Tea. So definitely running several different businesses at once at this point.


[00:11:08] JL: How did you come up with some of these business ideas?


[00:11:11] KV: For me, most of my business ideas have come from solving a specific pain point. In my case, working on Shopify stores. I saw plenty of merchants. They are trying to sell online, but I think the way that you think about building an online store versus an informational website is a very different mindset because the way that customers are interacting with your website on a product purchasing basis is definitely different from scrolling through and just like digesting information that’s available on that site. There are a lot of like intricacies to building out a store. So I decided to focus specifically on building online stores in, I think, 2014, 2015-ish, and basically solve a problem that I was seeing like a lot of online stores just weren’t not performing as well as they could because the developers didn’t know how to build specifically to sell multiple products at once. I think most of my other things like Ladybug, we just wanted to create a podcast to have women be the primary voices in the room. Commerce Tea was more of an opportunity to share what I know about selling online and e-commerce, and my cohost, Rhian Beutler, is also co-founder of a company. So we both have the entrepreneurship side of things there and being able to share all that information with other aspiring entrepreneurs and small business owners and even scaling Shopify merchants to help them continue to grow their business. So that’s usually where most of my business ideas came from.


[00:12:46] JL: Do you have any advice on acquiring your first client?


[00:12:49] KV: Be patient. That’s number one. Be patient, but also be persistent. I go through this in a chapter of my book about finding your first client and it’s by far the most difficult client to acquire putting yourself in the best light possible. So making sure you have a website set up where you’re talking about yourself and your services. If you have any kind of testimonials, you can share even like tangentially related, share them. And I think door-to-door selling can seem like it never works. And it has definitely a lower conversion rate for it. But I have a lot of respect for people who will go into a store and be like, “I saw your Instagram feed and I think that we can do a lot better job in promoting your products and generating more sales online. So I would love to express interest in basically running your social media strategy for you.” And it works. People will actually bite and you can sign on your first client like that. I think another one that I found that’s helpful is social media is a very powerful tool for finding your first clients or finding your first customer. Using hashtags to find people in related fields is a really big one or just interacting with other people who would be your ideal customer or your target customer and start forming those relationships early on. You want to build that trust in that if somebody is going to give you their money, they want to know that they’re going to get the product or service that they’re asking for in return and forming those relationships early on and having those ongoing relationships establishing that rapport is so key to actually getting that conversion and getting that customer or client to actually become that customer.


[00:14:30] JL: Courtland, I’m curious if social media had an impact or contributed to the success of Indie Hackers.


[00:14:37] CA: I think Kelly’s point is a really good one that especially if you’re going to be educating people and the product in many ways is yourself. People really need to trust you. And social media is such a great way to build that rapport and build that trust because a lot of times trust comes from just demonstrating your expertise and your willingness to help. And if you can tweet things out on Twitter that are interesting or funny or helpful or educational, then people will trust you. With other businesses specifically with Indie Hackers, I didn’t have very much trust nor did I build very much trust in myself, nor did I need to because the vast majority of it came from the other people that I was sort of aligned with. So in the early days of Indie Hackers, the website was basically just a blog where I interviewed people and all of the people that I interviewed were successful founders who shared their revenue numbers and many of them had their own social media presence and their own companies that sort of acted as conduits of trust where people could say, “Oh, I love this interview with Rosie Sherry and she built this million-dollar business. So I trust her advice.” And they don’t have to trust me because they’re not really learning from me. They’re learning from the people that I interviewed. And so that was sort of my shortcut trick to building an audience without there really being any trust in me. And I think through working on Indie Hackers and interviewing people and eventually releasing a podcast, people came to trust my advice more and came to trust me more as a person. So I actually didn’t really rely on social media very much at all in the early days, except indirectly through the people I interviewed who had their own social media presences.


[00:16:04] KV: I liked that because it’s like you uniquely built trust by being your connector. And by having those connections and sharing those connections with other people, that in a way returns to, they hear that story, they’re talking to you and in return, they see that you are trustworthy because you’re making that connection. It’s kind of interesting.


[00:16:23] CA: Yeah, exactly. It’s like you’re a connector, you’re a curator, and then where you get trust by osmosis, trust by association.


[00:16:29] KV: Exactly.






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[00:17:48] BH: So when I hear Kelly talk about her advice and Courtland speaking to the sort of pitfalls you started avoiding after some previous learning experiences, there’s definitely a sense of like jealousy like, “Oh, I wish I had the consultancy model so I wouldn’t have this like complex product cycle,” or like, “I wish I was doing indie hacking, so I didn’t have to report to the board or anything like that.” Can you folks talk about the grass is always greener kind of thing? I’ll throw this to Courtland first because you run a community of hackers and I’m sure there’s people sort of wishing they were on the other side. Can you speak to that a little?


[00:18:34] CA: Yeah. I think grass is always greener is an interesting psychological phenomenon that’s not just limited to what kind of business you start, but it’s kind of like every aspect of life. It’s really easy to compare yourself to other people. And when you compare yourself to what other people are going through, you tend to put on some rose-colored glasses. You tend to think, “Oh, other people were doing is so great.” You look at all the pros. You don’t look at any of the cons. You look at your own situation. You look at all the cons. You don’t look at any of the pros and then you switch and you’re like, “Oh, wow, this is not as great as I thought.” I think be open minded about what path you follow and the tradeoffs of any path because every path has tradeoffs. There is no path that you can take in life. That’s a hundred percent good and no bad. Otherwise, everybody would be on that path and would have been for the last 50,000 years. So if you’re going to go the VC route, for example, like you should realize that investors have expectations. And I think more than anything, if you’re a conscientious responsible person, you’re going to feel personally obligated to try to return the money given to you by these people who believed in you. And that’s going to be a lot of pressure that seems like it’s forced on you from the outside. And if things are going well, it’s great, but when things aren’t going well, it’s an additional source of, I think, stress and anxiety that you’re going to have to deal with. So you should only do that if you really trust your investors, you trust yourself in that situation and you believe you have a business that actually can grow to the size needed to get investors a return that’s going to make them happy. But there are downsides to other paths too. If you’re a bootstrapper, so pretty lonely path, like you don’t have anyone else who’s working on your company with you at the same level, you don’t have investors who can give you advice and feedback and you more importantly don’t have any money besides your own savings and your own bank account. And you’ve got to take that risk of potentially burning through your savings or quitting your job or spending a bunch of time getting up and running where it might be faster if you had a funded company. I think you really just need to examine your life and where you’re at and see, okay, which tradeoffs work the best for you. And I think if you make that decision very consciously and deliberately, then it can be a bit easier when you’re looking at what other people are doing to not feel quite as jealous and to understand the tradeoffs that they’re making as well.


[00:20:40] KV: I think that it’s important to stress that there is no one right way to run a business. I spend 99% of my time in a service-based business as opposed to a product-based business. So the ebbs and flows of money coming in very, very real thing. It is very difficult to project what the next month or the next quarter is going to look like for me. It’s gotten easier as we’ve scaled, but early on I could go an entire month without seeing any money come in. No new clients, no returning clients, whatever, learning how to manage that over time is tough when you’re a service-based business and it’s something I honestly still stress about to this day. Back to the comparisons as well, I think that’s definitely one of the things that I struggled with the most is I was continuing to grow my business is I was comparing myself to the wrong people. I think comparisons can be good in a way to give you goals. You see somebody do something very well, you’re like, “Oh, I want to do the same thing or I want to hit those same revenue goals or whatever it might be.” But you don’t know what’s going on in the background. You don’t know the struggles that they’re going through. We tend to share what’s great and what’s happening in our company that we want the world to know. We’re not talking about the losses. We’re not talking about the stress. We’re not talking about that every day, “How am I going to keep this business running?” So I think it’s really important, if you’re going to compare yourself to another business, understand that you’re only seeing a very small snapshot of what they’re actually sharing online.


[00:22:08] JL: Would you two mind sharing some of the challenges that you’ve encountered as entrepreneurs?


[00:22:13] CA: Like I mentioned earlier, when I moved out to San Francisco, I really wanted to start a company. I really didn’t want to go get a job at a big tech company, even though I could have. And if you give that up, which I did, and you don’t succeed, like I spent many years starting companies that didn’t work, telling all my friends and family I’m going to do this thing, hyping it up, launching, getting customers and then like two or three years later, shutting it down and sort of walking away to the next thing quietly with my tail between my legs. There’s never a moment where like that didn’t stay. Every time you shut a company down that doesn’t work, at least for me, there are thoughts like, “I feel like a failure and that was such a waste of time and I could have made way more money and been way more successful if I’d done something else. Is this really the right path that I’m on? Is it worth the pain? Is it worth the uncertainty? And at what point am I going to call it quits?” At some point I’ve been doing it for six or seven years and I hadn’t had any real startups success to show. And it’s like, “Well, do I do this until I’m 40? Do I do this until I’m 50? At some point, do I give up? And if I give up, will I always regret it?” There’s just a ton of uncertainty. And I consider myself very lucky to have started something that actually worked. I mean, I think the path is paved with failure and hardships, and yeah, there are some people who just knock it out of the park on their first try, but it wasn’t like that for me. And I think the silver lining to that dark gray cloud is that I learned a lot in the process. There’s no failure that I didn’t learn a ton from. I picked up a ton of skills in sophomore engineering. I became a much better backend developer. I became a much better designer. I became much better at dev ops. I became much better at marketing and writing. And when I look back kind of at my skillset today, compared to where it was 10 years ago, I’m almost a completely different person, despite those continual failures.


[00:23:53] KV: For sure. I think talking about what you’ve learned from these failures is really key because basically if you’re not going to learn something from a failure that’s much more likely to happen again, and we want to do everything we can to avoid history repeating itself when it comes to our failures in our business. For me, my first dev hire that I made was a mistake and it wasn’t so much that who I hired was a mistake. It was how I manage that hire that was the mistake. I had never managed a full-time developer before, especially being a remote developer. And I put too much trust into just letting them run with it without learning what their work style really was, what their personality type is, what kind of support they really need. And that developer ended up leaving I think eight months after I had hired them. I have since spent a lot of time learning how to be a better manager, how to make sure people are supported in the best way possible. And thankfully, I have more employees now who are sticking with me and are more than happy to call me out when I’ve done something wrong. And I think that is also one of the most important things is being open to feedback from others, even from your direct reports, being able to open up that conversation and provide that kind of environment for letting somebody come to you to tell you that you’re not doing something the best way possible, and maybe you upset them in some way, whatever it might be, be open to that feedback and actually take it to heart and make the change that’s needed.


[00:25:27] BH: Oh, yeah. We have some folks on our team who give us so much feedback. It’s almost hard to remember we’re doing stuff right sometimes.


[00:25:35] KV: I completely get that. Yeah.


[00:25:37] BH: Kelly, you spoke to the notion of being a service-oriented organization, and to some extent, I think that’s your identity, I’d imagine. Do you ever get the urge to get into product, as an example? Say you’re in Shopify, there’s lots of opportunity within Shopify to build product on that platform and stuff as opposed to services, is that an urge you need to fight? How does that identity of the organization, your makeup? What causes you to stay in one “line of business” versus another?


[00:26:12] KV: It’s actually something that I’m working through right now. So this is very topical. We are actually working on building out our first Shopify that we’ll be releasing into the App Store. So we are starting to product tie some parts of the business to have some kind of monthly recurring revenue coming in. We’re also taking some of our services that we have tended to do the same thing over and over again and productize that service as well. Basically what my goal is, is to create more steady income coming in for the company and kind of explore other areas, but I think that the toughest balance is, and this is something that exists for other agencies as well who are kind of split between the two, is how do you balance the service-based side of things and also add on a product that you have to support without spreading yourself too thin. So that’s why I’m easing into it with one Shopify app. A vast majority of the work that we’re still doing at the moment is very much service-based. I have one developer right now who’s focusing on apps who is going to basically own that project and I’m going to test the waters to see how that goes before I add anything new. One of the reasons why I want to actually explore this is because in speaking to other business owners who have been in this space longer than I have, they’ve made it very clear that a product-based business is going to be worth more than a service-based business if at some point I choose to exit. And I just want to make sure that the company is set up in the best way possible to be as valuable as it can be because this is my baby and I want to make sure I take care of it and I want to see it succeed and continue to see it grow.


[00:27:50] BH: Courtland, does your community have thoughts about service versus product? I imagine there’s a lot of ideas about more maintainable, maybe even passive income. Where do folks tend to land in terms of like freelancing and service versus developing products for that continuous passive income maybe with maintenance and growth?


[00:28:12] CA: Yeah. I think in the Indie Hackers community sort of Holy Grail is some sort of passive income, product-driven business. I’ve interviewed a bunch of people who run service businesses on the podcast and I think most commonly Indie Hackers do a lot of freelance work or might do some sort of like agency work as sort of a bridge to try to start our product-based business. It’s actually a very common path to build a team and generate revenue and then you use that team and that excess money to then build a product-based business, which can I think grow without some of the stress, but then there are some tradeoffs as well where it’s kind of harder to bring in money. So I would say like the community is very focused on product-based businesses. Almost everybody sees that as their end goal, but some of the more successful people that I’ve talked to started with an agency and I think that gave them just a lot of advantages that other people don’t have.


[00:29:06] JL: I want to switch gears and talk to you both about building communities because you’ve both done a really excellent job doing that, Indie Hackers clearly a community, and Kelly, you have a big audience on social and through your podcasts. How important do you two think building community is in order to be a successful entrepreneur?


[00:29:26] KV: It was very important for me to build that community because I am my business. So if I am the subject matter expert, I want people to see what I’m capable of and see that I can deliver on my work and see me, honestly, as an expert and creating that community has helped me scale my business as well. It’s kind of interesting now going through the hiring round for new developers since my last developer hire that actually went to the application process was I think December. And now that I have a much wider audience that I’m talking to on Twitter, for example, seeing the applications come in and seeing them reference the fact of how I talk about my business and how I’ve grown my business and everything, putting that information in the application goes to show that people are watching what you’re doing. People are taking very close look at what you’re doing, how people are talking about you, how you’re running your business. And for me, it’s actually impacted who has ended up working for my company and who has actually stayed on board. I think there’s also a lot of value in building a community where you can learn from others. I get total imposter syndrome for where I’m at now because I am a part of other communities that are people, in my opinion, who are much smarter than me, who have been in this space for much longer, and they just always have the right thing to say. And it’s tough because the imposter syndrome is very real in those situations. But I realized that as, over time, I communicate with these people, they see me as the subject matter expert in my area. So I’m the one who’s holding myself back. So by creating these kinds of communities, it’s allowed me to bring in new leads. It’s allowed me to build out a really strong team that we have at the taproom. It’s kind of pushed my own growth personally as well.


[00:31:19] CA: I don’t think it’s essential to have a community or even really an audience to build a business. There are plenty of businesses that don’t have communities, but it’s such an advantage if you have one. And I think there’s also even like a further distinction between an audience and a community where with me I had almost the opposite situation of Kelly where like I am not the product. I am not the business that is Indie Hackers. No one really needs to trust me. And if I go away, the community needs to be able to work without me. And so for me, I spent a lot of time trying to make sure that the Indie Hackers community members help each other. It’s all about building sort of the right structure, the right place. You can almost imagine like an auditorium or a stadium where the people are going to be able to do the best job interacting and giving each other support and that’s what fosters the strength of the Indie Hackers community. Whereas on Twitter, you could say like, “We have an audience,” and that’s more about sort of one to many broadcast, what I think is also extremely powerful in building trust, but it’s also parallels these sort of differences between the necessity of building trust when you have a business where people look at you as a subject matter expert versus where people are not necessarily looking at me, but they’re looking at the people that I was interviewing.


[00:32:29] BH: I think that’s really poignant and I think both of you brought up some non-generic ideas about community. I see a lot of community buzzwords out there these days. I feel like it’s caught on and it’s circled back as a thing people are talking about, but that doesn’t mean that it’s necessarily like things are changing, like the fundamentals of listening, of reading the room even if that room is really big and happening online is really all a part of understanding our customers, understanding the value given to them, understanding our brand, and it all sort of flows together. And sometimes when we might be in a phase right now where community is almost a buzzword in some ways, but there’s an authenticity that I think needs to persist.


[00:33:18] KV: One hundred percent. I think that’s the key word here is that authenticity.


[00:33:22] CA: I think it’s almost a good thing that community’s becoming a buzzword, not directly, but that it reflects the reality of that, like people are just starting to recognize the value of community. And especially with this pandemic, like just so much social interaction that’s happening online now rather than out in the real world and so many real-world communities are shifting to some form of online communities, like I play in a regular poker game back in SF, and now we’re just all on Zoom playing on an app, and like that’s a small kind of community. And I think it’s just so good for people to be connected and so many online businesses that didn’t really care about connecting people to suddenly prioritize that. The sort of gooey part of me thinks that it’s a good thing for the world for people to care and prioritize community. So if the consequence of that as a community is a buzzword, then so be it.


[00:34:09] KV: I like that.






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[00:34:53] BH: Another message from our friends at Smallstep. They’ve published a series called, “If you’re not using SSH certificates, you’re doing SSH wrong,” on their dev organization page. It’s a great overview of Zero Trust SSH user access and includes a number of links and examples to get started right away. Head over to to follow their posts and learn more.




[00:35:18] JL: So now we’re going to move into a segment where we look at responses that you, the audience, have sent us to a question we made in relation to this episode. The question we asked you all was, “What are some of the biggest lessons you’ve learned as an entrepreneur?”


[00:35:30] BH: Our first response is a recording from Robin with seven solid pieces of advice.


[00:35:35] ROBIN: The 22 years of filming software companies, I’ve got a few lessons. Firstly, the more isn’t there to protect you. It’s there to help the people with the deepest pockets. Secondly, pick your business partners carefully. We’ve had several started that well, but their intensions were not to build a long-term sustainable company. They were trying for get-rich-quick scheme. Make sure that before you get into something that people agree on what the outcome should be and make sure you have it written down because the next lesson is everybody’s memory is fallible. In fact, it’s variable and people retrospectively make up or select the aspects of history that they want to remember or reflect on them. Design your business model with the cash flow in mind, rather than simply providing a value. Work at your business model, work at your revenue streams, then wrap that around the core value that you’re offering. As best as possible, always do what you say you’re going to do. At the time, it’s harder. It takes longer. It costs more, but people remember it. Record trials of evidence as you go along. It has saved us on several occasions where people claimed we did the wrong thing, but we could show clearly by the decisions that we’d recorded the emails. We’d recorded we were behaving correctly and their perception was the problem, not us.


[00:37:26] JL: A lot of that advice came through in our conversation, especially with having a cash flow in mind. Courtland, I feel like that was a lesson that you learned in your first business.


[00:37:37] CA: Yeah. I think it’s something that you can and should start thinking about when you’re coming up with the idea for your business. Like what Kelly said earlier that her business ideas are usually to solve a problem. And when I first started companies, like I did not think that way. I thought, “What do I want to build?” And then once I build it, I’ll go and find the person who would like it. That’s the exact backwards way to do it. I think you should find a problem that people have. You should assess the nature of that problem. How many people actually have this problem? How deeply do they care about it? Are these people who I know and understand? And probably most importantly, is it a valuable problem that people will pay to have it solved? You can ask that question before you even come up with a business idea and you can kind of validate the answers by saying, “Well, are people already paying to solve this problem?”


[00:38:24] KV: I think that’s so important, especially just building out the entire business strategy. You need to spend some serious time looking at the top level stuff. It’s very easy as you said to get excited, to jump into the details and how you’re going to do certain things, but make sure you have that problem statement and your target audience and what your actual goals are. If that’s more than just make money, have them written down so you can use that as your guiding document essentially as you start to build out your business and as you continue to grow and analyze your growth.


[00:38:58] CA: Yeah. I love that point. I have a post that I wrote on Indie Hackers last year and it’s just called, “Questions to ask yourself before starting.” And I have like 50 questions in there about your goals and questions you should ask before you start your business because it’s not going to be all about money, like you said. And even if you think it’s all about money, if you succeed and start making money, you’re going to realize that there are other things you care about. And there’s all sorts of questions you can ask yourself. I think it’s really important to ask yourself who you are, what you enjoy, what you’re passionate about, what you can’t shut up about, what kinds of praise you like getting from other people, what kinds of mistakes you tend to make, et cetera, et cetera, so you can kind of work those into your business idea as well.


[00:39:36] KV: That’s one of the most important things that you just mentioned was, “What are you passionate about?” There are a lot of ways that you can make money. But if you’re not passionate about it, you are going to burn out. And if you want something that you’re going for longevity, you’re going for a longer lasting business, you have to have that passion of whatever it is that you’re interested in, in building or working on or solving whatever it might be. That passion has to be there.


[00:40:03] JL: So Miranda wrote in with two pieces of advice. The first one was, “Everyone starts at zero. Don’t compare yourself to others who are already successful. Remember that they started at zero too.” And the second piece of advice is, “Treat every setback, not as a setback, but as a learning opportunity. When starting, everything is chaotic and you feel like you don’t know what you’re doing. It’s okay. You don’t know what you’re doing and neither did anyone else when they started. It is really in this chaos where you can learn the most.”


[00:40:30] KV: I liked that last point, because even as businesses continue to scale, nobody knows what they’re doing even now. It’s not just when you’re just getting started. Nobody knows what they’re doing.


[00:40:40] CA: Yeah. There really is no playbook for most kinds of businesses. And if your businesses at the furthest point that it’s ever been at, which it usually probably is, then the future kind of looks dark and confusing and you probably have all sorts of options and you’re never quite sure what the right option is. She’s dead on. No one knows what they’re doing, even if they look like they know what they’re doing.


[00:40:58] BH: Scott writes in to say, “I think get out of the building is the most critical advice. Solve the real problem. Find the people to react to your solution. Time spent anywhere else is mostly wasted until you have a real customer feedback loop.”


[00:41:15] CA: Yeah. I agree with that. I think it goes straight back to the point of again, like what problem are you solving? And one way to think of it, like the word that’s probably most often used is market. To me, market encompasses who are your potential customers, what problems do they have, what other options do they consider, where do they hang out, how do they share and recommend products to each other. That’s all market and get out of the building is sort of a quick way to basically say, “You need to go figure that stuff out and you’re not going to figure that out by sitting around on your computer writing code all day,” which is the easiest sort of mistake to make as a software engineer, starting a business. So I think that’s great advice.


[00:41:52] BH: Kaushik writes in, “After more than a year of bootstrapping, here’s a small gist. Choose your failures, really difficult to get good at this, select a path which is less expensive and less hurtful. Play to your strengths everywhere. If your strength is prioritizing our customer support obsession, then play that card everywhere from your landing page or your email copy. Your visitors will immediately value your strength and resonate with you.”


[00:42:23] KV: I love that advice, especially being everywhere from your landing page to your email copy. It’s so important to have a consistent brand voice across everywhere you’re communicating. So yeah, definitely playing to your strengths and making that evidence across the board.


[00:42:40] JL: Stephanie wrote in, “Another thing is to give a lot of free value. Everyone, isn’t your customer and everyone won’t end up buying what you’re selling, but consistently giving away free knowledge will help you attract the right customers down the road. It sets you up as someone knowledgeable in your space and you become known as someone who wants to help people than sell them something they may not want.”


[00:42:59] KV: One hundred percent, and that is a lot of my content strategy. And that’s why I spend so much time putting out content, especially in the commerce space is I couldn’t keep all these things to myself. If you want to ask me a question, I can send you a link to my Calendly. You can pay me off 50 bucks or I can just share this information and that value comes back. From the information that I’m sharing this, the free value from this commerce-related content, I’m getting leads from it as well, but I know for a fact that it’s helping businesses grow because I get emails from merchants saying, “Hey, I listened to your podcast. I listened to this episode that you were on for another podcast and it really resonated with me and I immediately implemented your recommendations.” It’s a very powerful feeling and definitely something really important as well as you’re starting out is your customers want to know what you’re going to do for them in a way that like, “How are you helping me? Why should I spend my time talking about this with you? What are you doing for me?” Don’t make it about yourself, make it about the customer.


[00:44:03] CA: Being a founder in so many ways is about changing your perspective. It’s so easy to think, “I need this and I want this and this is what I’m trying to get,” but nobody cares. If you’re trying to build a company, that means you’ve got to provide value to other people, which means you need to get in the habit of thinking through other people’s eyes. What do they need? What do they want? What would help them? What problems do they have that they need solved? And you need to serve them. And by serving them, that’s how you build trust. That’s how you gain customers. That’s how you make sales. And specifically on the topic of giving things away for free and being helpful, if you have like any sort of business or brand that depends on people trusting you, like giving things away for free is one of the best things you could possibly do. Almost every educator that I’ve interviewed on Indie Hackers from Wes Bos to Saron, who’s at Dev, they all have like Twitter accounts or blogs or podcasts where they’re just giving away a ton of free information. And in the process, building loyal subscribers and fans who feel like they owe them, building up their own reputation and their own expertise in their customer’s minds, and that can easily translate into sales later on.


[00:45:10] JL: And on that note, I want to thank you both so much for joining us today and sharing all of your advice with us.


[00:45:15] CA: Yeah, this was really great.


[00:45:16] KV: Thank you.


[00:45:16] CA: Yeah. Thanks for having us.


[00:45:26] JL: I want to thank everyone who sent in responses. For all of you listening, please be on the lookout for our next question. We’d especially love it if you would dial into our Google Voice. The number is +1 (929) 500-1513 or you can email us a voice memo so we can hear your responses in your own beautiful voices. This show is produced and mixed by Levi Sharpe. Editorial oversight by Peter Frank and Saron Yitbarek. Our theme song is by Slow Biz. If you have any questions or comments, please email [email protected] and make sure to join our DevDiscuss Twitter chats on Tuesdays at 9:00 PM Eastern, or if you want to start your own discussion, write a post on Dev using the #discuss. Please rate and subscribe to this show on Apple Podcasts.




[00:46:22] SY: Hi there. I’m Saron Yitbarek, founder of CodeNewbie, and I’m here with my two cohosts, Senior Engineers at Dev, Josh Puetz.


[00:46:29] JP: Hello.


[00:46:30] SY: And Vaidehi Joshi.


[00:46:31] VJ: Hi everyone.


[00:46:32] SY: We’re bringing you DevNews. The new show for developers by developers.


[00:46:37] JP: Each season, we’ll cover the latest in the world with tech and speak with diverse guests from a variety of backgrounds to dig deeper into meaty topics, like security.


[00:46:44] WOMAN: Actually, no. I don’t want Google to have this information. Why should they have information on me or my friends or family members, right? That information could be confidential.


[00:46:52] VJ: Or the pros and cons of outsourcing your site’s authentication.


[00:46:56] BH: Really, we need to offer a lot of solutions that users expect while hopefully simplifying the mental models.


[00:47:03] SY: Or the latest bug and hacks.


[00:47:06] VJ: So if listening to us nerd out about the tech news that’s blowing up our Slack channels sounds up your alley, check us out.


[00:47:12] JP: Find us wherever you get your podcasts.


[00:47:14] SY: Please rate and subscribe. Hope you enjoy the show.