Community“I’m Not Bad-ass, I’m Just Lucky!”

I’ve been running my own businesses for 10 years and I’ve learned something:

Entrepreneurs who change the world aren’t self-made. They’re just …

  1. Born at the right time, when large world-wide patterns are changing
  2. Passionate about one of these world-changing patterns
  3. Able to create or raise capital
  4. Happy to take risks

We like to believe is that there’s some secret formula to building a big world-changing business. We believe that if we can just turn the dials just right, our graphs will hockey-stick upwards and our company will change the world.

Not true.

I know because I’ve experienced it.

My Experience

My three first business were small time:

  1. FlightDeck – A tool to send large files to clients for approval. Just me, doing less than $12,000 per year in revenue. Fizzled out because I priced it too high for a self-serve model.
  2. DropSend – A freemium tool for sending large files. Just me and a part-time Developer, doing $300,000 per year in revenue. Sold the whole business for around $450,000.
  3. Carsonified – An in-person training company for Web Designers and Developers. Grew to about 12 full-time folks, doing around $2m per year in revenue. Sold in 2011 for a pretty poor multiple on revenue.

Treehouse is a completely different beast. 75 full-time employees (hiring a ton more), on track to change millions of people’s lives, raised $13m+ of capital, working towards doing $100m+ of revenue, etc.

I’m the same guy, so what’s the difference?

Here’s why: I’m passionate about a world-changing pattern, at the right time in history. Notice the cover talks about igniting a revolution, not tweaking the numbers to increase EBITDA by 1.2%.

The world-changing pattern is this: The ability to become job-ready and get a job is being de-coupled from the university degree and simultaneously, there is an explosion of related well-paying tech jobs.

I’m hell-bent on creating an online school that actually makes people job-ready, without debt, and then helps them find a job.

There’s no guarantee we’ll succeed, but I’m going to die trying. I can’t wait to see what the future holds – it’s going to be one freaking exciting ride.

I’m old enough to finally realize that I’m not leading Treehouse because I’m a baddass entrepreneur. I’m just lucky.

This article was first published on Ryan’s personal blog Naive Optimist.

8 Responses to ““I’m Not Bad-ass, I’m Just Lucky!””

  1. Russell Roberts on October 30, 2014 at 4:39 pm said:

    Hey Ryan,

    I have to say that you’re really doing a awesome job with treehouse. I first heard about treehouse back in 2011 on Mark Suster blog “Creating the Next Generation of US Employees. My Investment in Treehouse”

    The university system is always evolving, with the likes of Coursera and udacity and anything we can do as a society to both decrease student loan debt and leverage technology advancements should be aggressively pursued.

    Treehouse has really helped me to understand what it takes to become a coder/hacker/developer/ designer. Now, I’m in a transitions of changing my profession from an accountant to a web developer, because I absolutely love it now and it’s all thanks to you guys. I truly do appreciate all that you and your team are doing over there.

    P.S. Keep up the great work!

  2. chris salvi on October 30, 2014 at 12:55 pm said:


    I have a larger question about start ups that revolves around how in the heck do you find those initial employees/funding.

    As a tech startup do you always need to have a prototype before investors are interested? So in other words you have to me either a very competent coder or know someone who is a competent coder and willing to sacrifice a big paycheck at a larger firm for the dream of striking it with a startup.

    Part of my love of coding is to implement ideas that have been brewing in my mind for quite awhile about language acquisition software not unlike the model you set out for treehouse, but more freemium based.

    I would love your input because I always feel like Im not strong enough to develop this idea on my own, but I believe it has a huge market if implemented correctly. It’s time to take down the RS.

    • chris salvi on October 30, 2014 at 12:56 pm said:

      i also live and work in the tech industry here in portland so maybe Ill stop by one day to talk to you in person.

    • Ryan Carson on October 30, 2014 at 4:07 pm said:

      Hi Chris,

      I would highly recommend building a MVP of your app first, getting some paid customers and then going to investors. It’ll help you get a good valuation, and it’ll also help you test whether the idea is viable before spending too much time on it.

      Good luck!

  3. Aside from being lucky you worked hard for it. It’s not only for the company but you also shared and opened up to the community

  4. Ryan, I don’t think you’re lucky at all. I think you’ve developed your current business model with a bit of selflessness, passion, and pure joy — all things that people are naturally drawn to. I remember back when Treehouse was Think Vitamin with Nick and Allison. Back then, I could recall thinking how there wasn’t much like it, and there still isn’t anything like Treehouse today either.

    Also, I don’t think it’s purely the teaching ability or content you put out, but the positive energy and willingness to show others the way. Best wishes to you, Ryan. In my eyes, Treehouse is already highly successful, and I don’t see that changing direction any time soon. You simply cannot lose by making the right decisions, and that’s what I’ve seen in Treehouse. Congratulations!

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