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Navigating the Startup Landscape

Courtland Allen

Indie Hacker, Stripe

MIT 09 ๐Ÿ› YC 11 ๐Ÿš€ developer ๐Ÿ’ป designer ๐ŸŽจ avid reader ๐Ÿ“š casual traveler โœˆ๏ธ StarCraft fan ๐Ÿ‘พย @IndieHackers at @stripe โšก

San Francisco
Courtland Allen

You'll learn:

  • How to get infinite startup runway.
  • How to reliably discover golden nugget business ideas (like a file upload form that makes six figures every month).
  • How Hotmail, AirBnB, Yelp, and Dropbox lied to you about their hockey stick growth.

About Courtland Allen

Every one of the hundreds of company founders Courtland has interviewed have failed repeatedly.

Courtland Allen founded Indie Hackers - an online community of founders and entrepreneurs. In April of 2017 it was acquired by Stripe. Courtland now works on IndieHackers full time.

Courtland has interviewed hundreds of founders in person and on the Indie Hackers Podcast discussing how the founders run their businesses. Most of the founders Courtland has talked to have been successful - some making millions of dollars per month - and every one has failed in some way.

Four startup landscapes. Each is a metaphor for a phase of your startup.

In this recap, you'll learn to avoid some common mistakes the founders he's talked to have made through four mental models of startup success: the Startup Runway, the El Dorado of Ideas, the Climbing Wall of Growth, and Vision.

1. The Startup Runway (of almost certain death)

The Startup Runway is a representation of how much money you have left and how much time you have until your business is dead.

Navigating the Startup Runway is simple: become cashflow positive before you run out of money.

How? In theory, the same way a pilot would navigate an actual runway. Keep your eyes on the end of the runway so you know how long you have left, study the capabilities of your "plane" so you know what it's capable of, and plan for a little extra buffer in case something goes wrong.

In practice, this isn't how it always works out. Let's talk about some real world examples.

Exhibit 1: Courtland Allen's 2009 Startup

Courtland won $25k in a business competition, which gave him a year of runway to build his startup in Boston. He spent the next year writing a lot of code and landing pages.

Eleven months in, Courtland launched his product but never charged his customers money. His startup failed because he ran out of money the next month.

Courtland's mistake was not keeping an eye on his runway. If he had calculated how much runway he had left, it would've become clear earlier that he needed to get money sooner.

Chris Chen

Exhibit 2: Chris Chen of Instapainting

Chris got a $110k loan for that gave him an impressive 3-year runway. Having a long runway meant he could try out many ideas and pivot if they weren't working.

After three years of pivoting, he ran out of cash. He moved entirely out of the social music app space and looked for an idea that could generate revenue immediately.

$4,000 in debt, he created, tested, and launched Instapainting in a few days. In two weeks, he'd made $2,000 in sales. Check out Chris's full story on the Indie Hackers Podcast Episode #002.

Exhibit 3: Max Lytvyn of Grammarly

Max Lytvyn

Before Max Lytvyn started building Grammarly he'd already successfully built a company, which gave him experience calculating runway.

With this experience, Max knew if he built an MVP without any customers lined up, Grammarly would run out of money.

Because Max had a good understanding of what it would take to launch Grammarly, he could try selling to institutions, organizations, and individuals at the same time while developing the product.

As soon as the first version of Grammarly was finished, Max had a pipeline of organizational buyers lined up. Grammarly became profitable in less than six months. Check out Max's full story on the Indie Hackers Podcast Episode #045.

The Helicopter Pad of Certain Slow Success vs. the Runway of Certain Death.

Alternative: The Helicopter Pad of Certain Slow Success

Instead of navigating the runway of certain death, you can use a helicopter! ๐Ÿš

The Helicopter Pad of Certain Slow Success uses the same money-and-time-management skill set as the Runway of Certain Death, but is much safer and simpler.

This metaphor is about burning through cash. If you don't want to burn through cash, don't quit your job! By keeping a stream of income, you don't need to be worried about running out of runway.

If you don't think you have enough time to work on your startup without going in full time, you can change the scope of your startup to be more achievable in the time you have.

Landscape 2: The El Dorado of Ideas

A beautiful Trello board of ideas the Indie Hacker member had put together.

In April of 2018, an Indie Hacker member posted that after a year of looking for an idea, they had achieved nothing but a Trello board of ideas.

Some of their ideas were bad, and the good ones were good but obvious - people were already working on them and already had established businesses making money.

There's a conception that coming up with ideas isn't something you can force, and that good ideas require inspiration and luck. Coming up with ideas, though, is a core skill in running a business. How do you build an audience? Launch successfully? Find new customer segments? Through the life of your company, you'll need to have the ability to come up with ideas. Treat ideation as a skill you can develop.

The El Dorado of Ideas.

To develop this skill, think about the set of ideas you could discover as a landscape of golden nuggets: The El Dorado of Ideas. Thousands of people are walking around looking for obvious golden nugget ideas to work on. The chances you'll find obvious gold that no one else has already picked up are tiny. This isn't a great strategy.

Another potential strategy would be digging lots of shallow holes: try building a quick landing page for a new idea every day and see what gets traction! You're more likely to find nonobvious gold than if you hadn't dug at all, but if you're not doing any deep-digging research you still won't find gold.

The best strategy for navigating The El Dorado of Ideas is to dig deep instead of wide.

Dig deep and get your hands dirty to find valuable ideas. Even if it doesn't work the first time, you'll have a skill set to dig deep again.

Digging deep means asking questions like:

  • Who are these people?
  • Where do they hang out?
  • What do they complain about?
  • What makes them really excited?
  • What do they buy? What do they never buy?
  • Who do they follow, trust, and respect?
  • What do they fear?
  • What are their goals?
  • What do they actually care about?
  • Where do they get their product recommendations?
  • What do they read, watch, or listen to?
  • What makes them angry?

You'll start finding ideas nobody else has found because not many people dig deep for good ideas.

If you have a new idea, dig deep again! Don't build your house over what you think is a goldmine without proof. Go back to El Dorado and dig deep. Successful multibillion dollar companies like Stripe don't just use their intuition - they talk to customers a lot.

How do you decide where to start digging deep? Start where the money is at. Look for places where lots of money is changing hands.

Also ask:

  • Are the customers reachable?
  • How long would it take to launch a product?
  • What are your weaknesses?
  • What's your runway like?
  • Would you like your customers?
  • What are your personal goals?
  • What industry would make you happy?

Wherever you dig, it'll determine the next five years of your life. Decide what's important to you and put some thought into what it would look like if you actually hit gold, and if you'd be in a place you actually want to be. Don't start a business that needs a lot of customer support if you hate customer support.

For more on the specifics of how to "dig deep," check out Amy Hoy's Sales Safari technique at Stacking the Bricks.

Landscape 3: The Climbing Wall of Growth

Hotmail, AirBnB, Yelp, and Dropbox all have simple romanticized stories about the one simple growth hack they implemented that got them hockey stick growth. It's a lie.

Most beginner founders think growth happens explosively followed by smooth sailing to the top. This is the simple story successful companies tell about their history, but it's not true.

One out of a million company might have a successful growth hack, but it won't be your company. Growth isn't a rocket ship sail boat - it's a climbing wall.

Growth is more like a climbing wall than a rocket ship.

At the bottom of a climbing wall there is no magical viral growth cheat code that instantly launches you to the top. Climbing is hard, and it's hard all the way up. Every step takes effort and attention. If you stop climbing, you stop progressing.

Don't waste time looking for the perfect first step. Just get started with a simple first step.

Once you've taken a small step, you'll have new steps accessible that you couldn't reach from the ground and you can reevaluate the next step to take from there.

You don't need a brilliant perfect strategy before you start. Nobody else jumped straight to the top. You'll never find new steps unless you try - just keep climbing.

If you feel stuck, look for paths others took. You can look multiple steps ahead at what's working for other people on your path. Knowing that a full mailing list will be useful a few steps ahead makes it clear that starting a mailing list now is useful.

To prevent getting sidetracked, set a destination. Climbing higher means you'll open more potential opportunities. Knowing where you're trying to go means it'll be easier to say "no" to things that don't bring you closer to your destination.

Jason Grishkoff

Exhibit 4: Jason Grishkoff of SubmitHub

Jason Grishkoff started a music blog, IndieShuffle, in 2009. For seven years Jason curated indie music and grew this blog to hundreds of thousands of visitors per day.

He started getting hundreds of pitches every day from musicians asking to have their music featured on his blog. To deal with these emails, Jason created the first version of SubmitHub so musicians could send him their music to review for a small fee. A few years later, SubmitHub was making six figures every month.

Simplifying this story makes it seem like Jason's business was a smooth sailing rocket ship. When he first published his story, Indie Hacker readers complained that Jason had it too easy because he already had a successful blog, and that they couldn't learn anything from his story.

Jason's full story on the Indie Hackers Podcast Episode #001 more accurately depicts the complex climbing wall of growth Jason went through. His growth wasn't as easy as it looked. It was a long hard slow slog, even with a huge audience:

"I hand tailored more than 1,000 emails to blogs. It took me five months of doing it every day. They didn't respond, so I would tweet them, I would Facebook message them, I'd send SoundCloud messages, I'd send another email. Then I'd try and find another contact. And we're still sort of doing this today. Those 250 blogs and labels didn't come overnight."

Even once SubmitHub was off the ground, Jason had challenges in getting labels and YouTube channels to sign up, working with other music blogs, tuning artist submissions. Each step in growth was a new unique problem. It took Jason eight months from launching SubmitHub to make his first dollar, and two years after launching to reach the impressive numbers he's at today.

Landscape 4: Living Room of Vision

Even if you don't have employees, having a vision is still important. The most likely threat to your business dying is that you get discouraged and quit working on it. How can you stay confident?

Courtland's living room, which may have a $3M diamond lost in it.

If you knew Courtland lost a multimillion dollar diamond in his apartment, how long would you spend looking for it? Hours? Days? Weeks? If you were confident there was a $3M diamond somewhere in his apartment, you'd probably stay motivated to look for it for years.

Founders that have high confidence in the vision of their business try much harder because they feel confident their effort isn't being wasted. They're systematically ruling out places where their metaphorical multimillion dollar diamond isn't.

If Courtland said there "may or may not" be a $3M dollar diamond in his apartment, you'd probably give up a lot easier. If you're less confident in the outcome, of course you'll give up when the work get hard.

The IndieHackers mission is to "inspire people to create internet businesses and to help these new founders succeed at a scale large enough to have a global impact" - that's a mission that can keep Courtland motivated for years.


Apart from content marketing, are there others ways to get early traction?

It depends a lot on your target customers. Everyone knows about the default places to launch, like Hacker News and Product Hunt, but that's all most people know about.

Is your audience indie game developers? Spend a lot of time with them. Learn what influencers they care about, where they hang out online (Amy Hoy's "watering holes"), and where they get their news.

Google is a great channel, but every customer segment has its own places online where they get new content.

How do you set your goal? How do you know where the top of the climbing wall is?

I had this issue with Indie Hackers. We were focused on how we could grow, but didn't know where we wanted to be in two years.

You get to decide your own vision. Make it something you can be confident in, and something you want.

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