How Courtland Allen didn’t let five years of failure or burnout stop him from pursuing his dream. Photography by Kati at Xilo Photography.
Disclosure: The story below mentions Stripe; ConvertKit is a paying customer of Stripe.
When Courtland Allen was a kid, computers were his playground – literally. His mom owned a company that sold computer hardware during the 90’s dot-com boom and Courtland and his twin brother played there for hours:
“If you put two bored kids in front of a bunch of computers, we’re going to figure out how to install games and keep ourselves occupied. It wasn’t that long before we knew more about how to use the computers than all the adults in the room.”
Environment is powerful, and all those adults kept telling Courtland, “You’re so good at computers. You’re going to be the next Bill Gates.” Courtland had no idea who that was back then, but he used his computer skills to look it up: “Oh he’s a programmer? I want to be a programmer, then.”
By fifth grade, Courtland had a solid dream and a plan: “I want to go to a good school and I want to learn how to code.” He admits he had no idea how to do either at the time, “but I was pretty sure that I would.”
Courtland is contagiously optimistic. After you meet him you find your biggest, craziest dream coming out from the dark. You didn’t realize you’d been hiding it, but for the first time in a long time you hold it in your hands, and ask: What if this is possible?
Much of his faith in possibility (and luck) comes from his parents. His mom was a serial entrepreneur who always believed she could make her own way (and always did), and his dad was part of a furniture-building collective. “Both my parents were resolved to not follow the system or have a normal nine-to-five job. So, for me, it was always pretty normal to not go that route.”
If Courtland’s family had a motto, it would be: “You can do anything.” When Courtland played basketball, his dad told him he’d be the next Michael Jordan. When he started playing saxophone his parents said, “You’re going to be the next Kenny G.”
But Courtland didn’t want to be like Mike or Kenny. He wanted to be like Bill.
Ugh feeling so dejected – how do you get over your first big business failures???
But even with his big dream and optimistic outlook, Courtland was still shocked when he received an acceptance letter to MIT. After the elation wore off, he remembers thinking, “This is a mistake. I should not go here. This is like something people in movies go to.”
But in some ways his life would play out like a movie.
The call to adventure. Check.
Relentless failure? You bet.
Courtland’s first five years of entrepreneurship were filled with rejection and failure. While at MIT, every idea he submitted to Y Combinator, a well-known incubator for early-stage startups, was rejected.
He looked at it all as “a fun learning experience.”
But he was encouraged by every rejection email. He never got a form rejection letter. Instead, he got custom feedback from the leaders of Y Combinator each time.
He remembers getting emails like, “Oh, I think this is cool. But you guys are all in school, you should finish school first. This is not promising enough for you to quit school.” And, “Oh, I think this is kind of cool, but we already funded a company like this. It’s conflict of interest.”
Courtland also got some rejection emails where they honestly told him it just wasn’t a good idea. But getting any kind of feedback from people he admired was proof that he was at least heading in the direction of his dreams. It was enough to keep him going.
Eventually, right after graduating from MIT, one of Courtland’s business ideas won a business plan competition and he was able to live on that check for a year while he tried to get that business off the ground.
But the money ran out and the business didn’t make any.
Courtland realized, “This company is dead.” But again, he was not deterred. He didn’t really process any of these business failings as personal failings. He looked at it all as “a fun learning experience.”
With the end of that business, he moved to Silicon Valley to “be where the action’s at,” even though he had no job. His only plan was to apply to Y Combinator again and see what happened from there: “Best case scenario, I get in, and that’s great. Worst case scenario, I don’t, and then I just get a job and just keep applying.”
But being an optimist doesn’t mean you’re immune to fear – you just choose hope when it does hit. But it still hits – hard.
In Silicon Valley Courtland quickly connected with the community, and soon courtesy of the social news site Hacker News, he met someone to co-found a company with. They came up with an idea over coffee and applied to Y Combinator as partners.
They got in.
Courtland was about to be thrust into an environment where success was only counted in billions.
Is having a billion users really the only way to make it???
Courtland loved the energy and community of living in Silicon Valley (and still does), but it was also hard to ignore the prevailing doctrine of 2011: “Go big. Raise a ton of money, and don’t care about charging customers. There’s no real money in charging customers. First thing you need to do is get a billion users and then you can figure out your business model.”
Courtland and his partner put all their energy into trying to get a billion users. “We tried, but it didn’t really work. We got like 50,000 people, which is a lot of customers to get. But they were all paying zero dollars.”
And since they weren’t meeting the big metrics investors were looking for, they didn’t get any further funding once their incubator time ran out.
“People are paying us money for this little widget we built! Who would’ve thought?”
But then Courtland heard about this new company called Stripe – software that made it easy for startups to charge for software. It was so easy that Courtland decided they had nothing to lose.
Going against the business models he’d been taught up to that point he thought, “Why don’t we just slap this on our app and see what happens?”
They made $2,000 that weekend.
While that’s nothing in Silicon Valley terms, to Courtland, it was everything. A revelation. “This is so cool. People are paying us money for this little widget we built! Who would’ve thought?”
But he was still so embedded in Silicon Valley culture that it didn’t take long for the $2,000 to feel like nothing. Advisors said they needed to expand more. In hindsight, Courtland says he should have continued iterating on this thing that already had traction, but instead they shut it down to try to build something new that was built to make money from the start.
They worked on it for three years, but it didn’t take off, and Courtland started to get burnt out.
“Eventually, I just quit.”
He was tired of struggling to make ends meet in such an expensive city. He needed a break, some time to recover from the “five-year gap of miserable startup failure” when “nothing I tried worked.” Sometimes the only way to keep going is to stop.
Should I just give up now and go back and get a real job??
To make ends meet Courtland became a contract web developer, coding and working from home and finally making consistent money. It was also the first time he’d ever worked less than 12 hours a day. He was able to finally come out of his hustle cave and spend time with friends, “enjoying the life that I had not enjoyed the first couple years after college.”
It refreshed him. But an entrepreneur at heart, it wasn’t long before the drive to start something new returned. It came first as self-doubt: “I started feeling pretty bad about myself because I had told myself I was going to be an entrepreneur. It wasn’t my goal to just work for clients and make a cool salary. I was grateful for it, but it wasn’t why I started.”
He started saving money to use as runway for his next business idea – even though he had no idea what it would be.
How long does it take to come up with a business idea that actually works??
Using everything he learned in the last five years, Courtland made a checklist to help him find his Next Big Idea.
It was a very personal checklist, based on all his “failings and mistakes” and what he knew he wanted this time around.
He wanted something he could launch quickly; it was the summer of 2016 and he only had enough to make it to March 2017.
He also didn’t want to pick an idea that would require a lot of code: “I love to code, but if I work on something that requires a ton of code, I’ll just code for eight months and not talk to anybody.” He knew he would need time to do other things like sales, and, coding was a vortex he’d get lost in.
He wanted something he could easily explain to friends and family: “When no one gets what I’m doing, they can’t be supportive because they don’t even know what it is.” That kind of support was important to him.
“What if I curated stories that answered the exact questions people like me are having?”
He also wanted to really like his customers: “I don’t want to build something for customers I don’t like because then I’m not going to like my job.”
And he wanted to choose something that used his best skills – something to give him an edge up on others who might be doing something similar.
Armed with his evaluation criteria, Courtland started brainstorming ideas like crazy. He evaluated each with his new rubric and spent three full days doing nothing but scouring for ideas.
Hacker News gave him a lot of inspiration, scrolling through endless forums to find stories of programmers who made their businesses work.
He started bringing all his ideas to his checklist. It wasn’t great at first.
“I came up with a lot of garbage ideas. Just a lot of really bad stuff that I’m so glad I didn’t work on. But I’m glad I stuck through it because the ideas got better and better. By day three, most of my ideas were pretty good.
“We tend to think of ourselves as either good at something or bad at something, like I’m good at ideas or I’m bad at ideas. But it turns out that you just need a warmup. If you do anything all day every day, eventually you’ll get good at it.”
There was exactly one idea that checked every single box on Courtland’s list.
Is there one place to get the answers I’m looking for??
During his research and ideation phase, Courtland would have 20 tabs open at any given time. He spent days scrolling, scrolling, and scrolling through forums, reading thousands of comments to try to find stories of programmers who’d successfully started a company.
He noticed there were many on these forums looking for answers to the same questions he had, like, What is your one-person SaaS business? How are you making money online as a developer?
“The problem they have is the same problem I have. They know they want to build a business, but they don’t have any ideas. They don’t know how to get started. They don’t know how to generate revenue.”
Courtland noticed that people seemed to upvote the stories people shared more than anything else – they found the real examples inspiring and instructive. But it took a lot of work and scrolling and time to find the good ones. Courtland wondered, What if I curated stories that answered the exact questions people like me are having?
The idea for Indie Hackers was born, and once Courtland saw it checked every single box, he got to work. But the clock was ticking. He only had eight months until his savings ran out.
Feeling overwhelmed…where should I start??
To start, Courtland researched again, but this time, instead of reading forums for his own inspiration, he was out to deliberately understand which stories rose to the top and why.
He found patterns.
It almost felt like cheating, he recalls; the best research always feels that way. You can’t believe all this gold is just sitting right there, for anyone to take.
You wonder how much you’ve been missing and wonder if anyone understands the beauty of what you’ve just found. But that’s where all the creative energy comes from – you can’t wait to employ your craft to connect and help others see what you see and feel what you’re feeling.
Based on his observations, Courtland made a list of five things he wanted every story to have; things like telling the story in chronological order and sharing numbers transparently. All the effort he was putting in this time around made him realize what might have gone wrong in the past.
He doesn’t think he spent enough time on research in his previous business ideas: “The hardest part of doing something new is not building it, but getting anyone to care. A lot of people build stuff – there’s billions of websites…but how many do you go to every day? Like five?”
He recalls the painful past when he’d take six months to make something only to have no one care about it in the end.
“So this time, I knew I needed to start with my audience in mind, to know who they are, what they care about, what they want, where they hang out, and what kind of messages resonate with them, and then work backwards from that – because that’s the hard part. Once I got that figured out then creating was pretty easy.”
Courtland used his audience’s top needs to craft his interview questions and emailed 140 entrepreneurs with an interview request.
Reaching out and getting nowhere…how do I get people to respond to my emails??
There was no copy-and-paste-then-change-the-name going on here. Courtland researched every creator he emailed and started each email with what he genuinely appreciated about them.
“I sent 140 cold emails just to get my first 10 interviews on the site. That means 130 people didn’t give me interviews.”
Instead of thinking about the 130, though, he focused on the 10.
He knows that without all his personalized emails he probably wouldn’t have even gotten those 10; he was reaching out cold, asking people who didn’t know him to be featured on something untested, unknown – something that didn’t even exist yet.
He also used this email strategy when seeking advertisers. “Every sales email I sent was custom.” He also worked to find the name of the person at each company most likely responsible for ad buys. “It’s not like you have to be genius – it’s just how much time are you willing to research?”
“It wasn’t my goal to just work for clients and make a cool salary. I was grateful for it, but it wasn’t why I started.”
There were some potential advertisers he didn’t email, though, like Stripe; he considered them a dream company and he didn’t want to email them until his site had really taken off and had the best possible chance of making a great first impression.
He sent about five custom emails per day while he built the site from scratch (yes – coding – he couldn’t resist). But since he followed his list and chose something simple, a blog, he was able to code it in about three weeks, right on target. Now all he had to do was launch.
But being an optimist doesn’t mean you’re immune to fear – you just choose hope when it does hit. But it still hits – hard.
Help – my traffic plummeted!!
Courtland launched his site on Hacker News and that’s when the fear hit: What if no one reads this? What if no one cares? What if this stays at the bottom of Hacker News forever?
It started at the bottom, and nothing happened.
But an hour later, it seemed all his research and all he implemented from the last five years of trial and error paid off – his site rose to the top of Hacker News with 100,000 pageviews in the first few days.
He doesn’t remember sleeping much during that time – awake and high from the energy of his idea actually working.
But then, “this happened” – Courtland shows me a graph that looks like it could also easily be “Popularity of N’Sync Christmas album from December to February.”
“Every day the traffic was lower than it was the day before.” Courtland started to get worried. His business model was advertising. He needed consistent traffic.
People were loving the site – he was getting a ton of compliments. In fact, when my friend Kris, also a ConvertKit programmer, found out I was writing a story on Courtland, he told me how Indie Hackers impacted his life:
“It was really inspiring to read about people finding success online who weren’t taking VC funding; they just wanted to build sustainable businesses. Because everything was so public I knew it was possible, and because of Indie Hackers I now work for an ‘Indie Hacked’ company and I love it more than anything else I’ve ever done. Indie Hackers has kind of been like my north star.”
Indie Hackers also got a lot of attention on Hacker News and Product Hunt. But Courtland knew those big spikes weren’t enough to build a sustainable business. There also wasn’t a lot of incentive for them to come back and check it every day.
That’s where his email list came in.
“I would have probably just gone crazy by myself if I didn’t have this email list that I was talking to. It felt like people were sort of working with me.”
How do you get your first email subscribers??
At the end of each interview on his site Courtland had a form asking people to join his mailing list to get more interviews. And with the attention his site got when he first launched, he had 1,000 email subscribers after his first week.
He also cleverly had a “Forum” link on his top menu – when people clicked on it they were taken to an email signup form that asked them to sign up to be the first to know when the forum was ready. Courtland hadn’t even begun coding it yet but he started collecting the emails of those interested right away.
He emailed his list every Thursday. His emails were personal. He worked in public.
He took his list along for the startup ride; each week he’d share the highs and the lows, new features based on their feedback, and new interviews.
Traffic rose steadily. The emails gave people a reason to come back.
It also changed the way he found people to interview; many of the people on his list were entrepreneurs already and replied to his emails asking to be interviewed.
“Within a week I no longer had to cold email people.”
He also found great camaraderie and comfort from his list: “I would have probably just gone crazy by myself if I didn’t have this email list that I was talking to. It felt like people were sort of working with me.”
Their replies became another rich source of research, helping him iterate all along the way. “Even though it was just me alone in my apartment, I had all these people who were super connected and wanted to help.” They felt like they were also a part of his story. Because they were.
In one email, Courtland shared how scared he was about his advertising business model. He immediately got a reply from a guy on his email list asking where he could send Courtland a check for $800 to become his first advertiser, simply “because he wanted to help.”
To sell or not to sell – anyone ever had their company acquired??
Despite traffic going well, if Courtland didn’t start getting more advertisers he was going to run out of money in March and have to shut down.
He focused all his time in December cold-emailing using his custom method. Money started trickling in. Slowly. He made $1,200 in December.
By February he made $4,000.
In March he got invited to a wedding in Mexico. He decided he should take a break from work, trying to avoid that burnout that hit him years ago. But he couldn’t resist checking his email at least one more time before he got off the plane.
He was shocked to see the name of Stripe’s founder – Patrick Collison – in his inbox. The subject line? “Acquire Indie Hackers.”
Courtland still hadn’t emailed anyone from Stripe yet, waiting until he was “ready.”
Turns out Patrick thought he was more than ready. They believed in what Courtland was doing.
Patrick didn’t want to change anything about Indie Hackers, or take over, or make Courtland a traditional employee. Stripe wanted to support Indie Hackers in the biggest way possible, allowing Courtland to take off his sales and advertising hat and instead focus all his time and energy on creating content that inspires more people to start businesses.
Courtland immediately forwarded Patrick’s email to his girlfriend, mom, and brother. “I was blown away.”
After meeting Patrick and understanding what this could mean for Indie Hackers – and his life – he knew it was the best way to keep it going and have the time to invest in his biggest dreams for the site, like creating a community and starting a podcast (before I leave, Courtland gifts me with an Indie Hackers T-shirt and stickers that feature a beautiful custom-designed illustration of an astronaut holding a laptop to represent the Indie Hackers brand, physical proof of the kinds of community-building projects he was given the time to create).
For that MIT kid from Georgia who moved to Silicon Valley with no money, no job, and lots of optimism, it was a dream come true.
How do you know when to stop and take stock of how far you’ve come??
Though Courtland lives in walking distance to Stripe’s headquarters, he calls an Uber for us so we can make it there before the lunch service ends. He still mostly works from home, but comes to Stripe once in a while to have lunch and meet with people. We arrive just in time and the woman working the buffet of enchiladas lights up when she sees him: “Hey! We haven’t seen you in a while!” They banter back and forth and laugh a lot.
After we eat he gives me a tour of the expansive, bright office space, and as we stroll through the library, just past a common area that looks very much like a lush greenhouse, I ask him what his dad, who believed he could be the best at whatever he did, thinks of all this.
That’s when Courtland tells me that his dad got sick before he applied to MIT. The doctors didn’t know what was wrong for the longest time. He was in and out of the hospital, spending four horrific months in the ICU. But Courtland tells me that he was optimistic even then – he fully believed his dad was going to get better, every single day.
Until the day he died.
Courtland says losing his dad was like the dark mirror of the feeling of getting that Stripe email – a thing you absolutely didn’t expect to happen that changes your whole life, forever.
We walk out Stripe’s doors into the crisp San Francisco air and try to guess what Courtland’s dad would think of where Courtland is today (Courtland’s twin brother Channing also works on Indie Hackers). It’s hard not to smile bright as we think about how very, very proud he’d be – but also probably not surprised.
“If I’m ever a parent,” Courtland muses, “that’s my rule number one – give super optimistic, you-can-do-anything encouragement. I wouldn’t have tried as hard if I didn’t get that encouragement. I can directly trace it back to the people who believed in me. Because they believed in me I believed in myself, and did things that I would not have tried otherwise.”
Additional resources + guides to help you start your dream business:
Goal Setting: Defining Your Own Success as an Online Creator
Money Matters: How to Run a Profitable Online Busines
Every Day I’m (Side) Hustlin’
Are you a creator using ConvertKit? We’d love to share your creator story next!
The post “Because they believed in me I believed in myself.” appeared first on ConvertKit.