Hacking Your Education With Dale Stephens Of Uncollege.org

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Dale Stephens was frustrated with his freshmen college experience, so he decided to start his own alternative path to education.

After investing several years building his personal brand, he founded Uncollege.org, a company that provides Gap Year programs for young adults who want to drive their own education, explore and make a splash in the world.

They’ve been doubling their customer base year-over-year for a few years, and are in high-growth mode!

Dale also wrote “Hacking Your Education”, which is a collection of how dozens of people have hacked their educations to create incredible opportunities from alternative paths.

In This Episode, You’ll Learn:

  • How Dale built an alternative education company, Uncollege.org and wrote “Hacking Your Education
  • Dale’s recommendation for 15-18 year olds trying to decide what they should do after high school
  • Why the old-school education system is broken, and what Uncollege is doing to help fix it
  • The most important skills from 100 professionals that’s not taught in school

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Chris: Hey everybody. We’re back with another awesome interview. This is the one I'm actually really excited about. It’s Dale Stephens who is the founder of UnCollege.org and also the author of Hacking Your Education. Dale how’s it going?

Dale: Doing great.

Chris: Awesome. Thanks for being here man. Is there anything else that you would like everybody to know about you?

Dale: I think those are the main two things.

Chris: Alright, awesome. Let’s talk about UnCollege and what it is. As everybody watching the show knows, I'm a huge proponent of self-education or alternative routes to education. I dropped out of college, barely graduated high school, but I am ferociously reading everything I get my hands on and looking for ways to learn quicker and smarter.

Dale, just give us a little bit of insight into what you guys do and how that business looks?

Dale: UnCollege started almost five years ago now initially as a movement to support people who are dropping out of college who are self-directed learners who wanted to follow their own path. That community has grown and stayed online, and over the course of time, we’ve developed a program that we called Gap Year to help people who want some more support in that adventure.

We offer coaching services, internship placement and some abroad services for people who are mostly coming right out of high school who may be aren’t sure exactly what they want they want to do yet. They're really smart and want to pursue higher education but they don’t think that committing four years and $200,000 when they don’t really know what to do is necessarily the right move.

The program is a 9-month program that involves international service learning, coaching in curriculum residentially in San Francisco, and then an internship to finish out the year that helps young people really maximize their higher education if they want to go onto college and also gives them the right set of skills and tools so that if they want to enter the workforce directly, they have the capacity to do so.

Chris: What types of things do you cover in that program? What are you educating on and how does that look for a student that just gets started? Walk us through that process.

Dale: Our curriculum is really around where what we think of as meta learning skills, the skills that you feel better and more effective. So things on how to negotiate, communicate, get yourself motivated, advocate for yourself, give and get the feedback, the basic fundamental life skills that are really important to be a successful adult that no one ever bothers to teach you explicitly.

The thesis when we started the program was to say, it’s great, it’s great learning content, right? Doing essays on and learning about medieval China and so on and so forth. You can learn those things from that contact.

Well, we wanted to ask the question, could we teach that contact more quickly is actually explicitly taught the things that we are trying teach. How to think critically, how to work in teams, how to give and get feedback as opposed to assuming that students are going to pick it up just by proxy of doing a book report on a famous 

Chris: I love it. So it’s all of the important soft skills or intangible skills that really, in my opinion, I think we should be teaching these things in high school and as far as I know, they're still not. Are these things still lacking in the traditional school system?

Dale: The vast majority of schools look almost exactly the same as it did 150 years ago, right? Yes, there are certainly some schools that are project based that have incorporated technology but it’s a very very small percentage.

Fundamentally, school doesn’t start with the learner. The school starts with the teacher delivering content. If we really want to take this to the extreme, we should be asking kindergarteners what they're really interested in and then tailoring the content to that.

What crossed my mind when I give talks at teacher training and freshman development days is that all of the teachers say, “Well, elementary school students don’t know what they're interested in” and I'm like, “Have you ever bothered to ask them?” Every six-year-old I've ever talked to has a pretty clear idea of what they're interested in. It’s just a matter of taking the time to actually ask them and put the learner’s priorities over the priorities of the teacher.

Chris: Interesting. What prompted you to start your organization?

Dale: I was really frustrated with my freshman year of college. I had a really shitty experience. I went to a small private liberal arts school that was full of well-intentioned people who I think would use a lot of the same words to describe what they do as I just used to describe what we do except they threw us into four classes, none of which particularly good, and mostly taught us facts that I could look up on Wikipedia. I didn’t think that was particularly useful and certainly wasn’t worth $40,000 a year.

When I dropped out of college, I was really frustrated with my freshman year experience. I've taken a bunch of courses that felt like I could’ve looked up the facts on Wikipedia and ended up saying the right things at the right time. I was what to become a tidal wave in higher education.

I ended up writing this book, Hacking Your Education as you mentioned and I've interviewed about 100 people who don’t know what to do interesting and successful things with their life without relying on formal education.

I interviewed doctors, entrepreneurs, architects, lawyers, and DJ’s some of whom have gone to college, some of whom had dropped out, but none of whom had relied on the knowledge that they learned in the classroom for their professional careers.

What became really clear was that there were these set of skills that you needed to survive as a successful adult that made you a really good learner, made you adaptable and flexible and willing to ask questions and say that you don’t know and how to interact with mentors, all of these intangible things.

I started wondering, if these are the things that are important, why aren’t we teaching these skills?

Chris: What would you say is the number one or the top skills that you feel are the most important and maybe that were the most prevalent among all the people that were in your book?

Dale: Self-awareness, self-advocacy, and self-control. Those are the three things that are really highly studied. Self-control in particular is something that we know, then a lot of work around delayed gratification and showing that those who passed The Marshmallow Test who are willing to wait for a reward rather than take the short-term gain are absolutely more successful in life across a broad range of areas. This correlates much more closely than IQ or SAT scores, even from very very young kids.

There are ways that you can develop that. It’s actually possible to develop self-control. It’s not like this is something that we have no control over but you have to build a society that rewards kids for making longer term choices than short-term gains.

Chris: Nice. By self-control, do you mean discipline and choosing to do the work now—

Dale: Habit forming. The Marshmallow Study that I'm referring to is the most famous of this. They basically gave 5-year-olds a choice between a marshmallow now or two marshmallows if you wait a minute longer. And the videos of little 5-year-olds fidgeting for the minute are hilarious. You can find them online but the ones who were able to wait it out ended up vastly more successful, wealthy, had more papers published, given more talks, and won more prices, a huge of swath of ways to measure success.

Those who had the self-control to delay that gratification were much more successful in life.

Chris: Nice, so I want to take this back to the company and the organization that you built. Where are you guys now? How many employees do you have?

Dale: We’re at nine full-time employees right now which is still pretty small. We’ll do about 60 students through our program this year which is double what we did last year and we’re on track to double again next year.

Right now, it’s really at a stage of growing and scaling the organization, so it could have the maximum impact. Most people’s freshman year of college is a pretty shitty experience and we envision a world where we can really start partnering with college to say, “Hey, why don’t you let your students do this, really transform the experiential program instead of seeing them in electro hall with 500 of their closest friends?”

Chris: Yeah, absolutely. I've always loved the idea of a gap year and I think the structure that you put around it is really brilliant. I've met kids through my travels like in Asia, Australians who to take a year and primarily they just get drunk and just party that whole year, but it sounds like you're putting a structure around it to really help them discover where they want to go in life and the best way to learn and those intangible skills that maybe they haven’t been taught in the school system. I love the idea.

How are you guys reaching high school kids now? Are you doing much marketing or is it organic, word of mouth?

Dale: Most of it is organic and word of mouth right now. We do a little bit of outreach to high schools. We’re actually in the process of hiring someone to focus on outreach to high schools full time. Just because we’re getting more inbound interest and visits from high school that we have actually have the capacity for with our current staff.

We had a councilor stop by the office today, one of our marketing guys was at home in Seattle on Thanksgiving Holidays and has visited prep schools and this week. It has been pretty ad hoc to this point but we’re getting a lot of interest from schools who are recognizing that for many students, recommending that they go straight to college is probably not the right choice.

Chris: I completely agree with that. What would you say to the 15- to 18-year-old guy or lady or girl that is watching this right now? What advice would you give them?

Dale: Your parents aren’t you and you shouldn’t let your parents’ expectations of what they want you to do impact what you want to do, that there is not one right way to be successful. Money isn’t the only way to measure that. Impact isn’t the only way to measure that.

Happiness is the only way and you should really take the time to understand what really fulfills you and what makes you feel satisfied. Everyone’s going to have a different answer for that question.

Chris: Yeah. I think that’s the big challenge, right? Kids that have the pressure of their parents. I felt this. My dad was like, “Look, you have to go to college. You have to get a degree.” If not, by his definition, you're a failure. I just think that’s just really sad, so how would you recommend that a kid reaches out to their parents and say, “Hey, here’s this other alternative.” How can we explore that? Do you have material online that you would say, “Hey, yes. Send your parents here to learn about what we’re doing and why this is important.”

Dale: Yeah. We do have content for parents and they can certainly check out blog at blog.uncollege.org for resources on that. We find approaching it from that perspective “Hey mom and dad what do you really want for me? I really want to be happy.” It’s pretty hard to find parents who disagree with that, right? Most parents really want their child to be happy. And if you come out from the perspective of a feeling as opposed to some objective truth, you're often able to make a lot more progress.

I would also say that it’s really important to develop your own networks of support outside of your parents whether that’s other people’s parents, whether that’s mentors, whether that’s people at school, whether that’s a boss at a first job.

Certainly, for me and for my parents, I know we all develop networks of support that weren’t actually immediate family who were there to keep us in check and also people whom our parents respected and could help have that conversation if our parents, I say, got blurred a little bit in the short term because they're focusing on a long-term goal a little bit too much.

Chris: Nice. What’s the biggest challenge that you faced while building your company?

Dale: I think this is probably fairly cliché at this point but finding the right people is really hard. The first people that I hired were not the right people and we have an awesome team we have for about two years now. But the first six months were really hard because I hired the wrong people and I don’t actually know that there’s any substitute for this.

When I was hiring my first team, I went and asked a bunch of mentors for their best advice on hiring and they recommended a few books here and there but pretty universally across industries, they were like, “You’ll f**k it up for the first time” which is definitely true.

Chris: Yeah. Hiring is absolutely one of the most important pieces and one of the hardest. It’s interesting because you have one of probably the best talent pools in San Francisco. Did you hire locally or did you pull people in from different areas?

Dale: We’ve mostly hired locally. I think we’re lucky in that we sort of get the cache of being a start-up without actually having to compete for technical talent which is great, hiring a lot easier for some people but the dynamics of working at a small company are really hard.

You can try and understand how someone who’s going to operate in that environment with a lot of uncertainty and a lack of clarity between roles and times when we have to put in a lot of hard work and times when you're going to get frustrated because you're doing something that you’ve never done before. The person who’s managing you is doing something that they’ve never done before, and you have to be willing to say “I don’t know” and accept people’s apologies and realize that not everyone’s perfect.

If you're the kind of person who wants to be in a large organization with a clearly defined role in an HR Department, start-ups are not for you.

Chris: Yeah. Here in Austin, we have a much smaller start-up community but it’s growing and it’s interesting to see the huge difference and challenges at start-ups space versus big corporate companies. What’s one piece of advice you’d give to somebody who’s a young entrepreneur looking to start a company?

Dale: Don’t do it unless you really understand what the costs are. It’s really hard. It’s emotionally hard. The level of responsibility is stressful and it’s a long road and it’s a 3- to 6-year commitment at minimum.

I don’t know that anyone actually said that to me explicitly when I was starting the company.

Chris: Yeah and I know it’s seems like being a start-up founder is so cool and it’s one of those things that I feel like a lot of people ever since Shark Tank started coming out, entrepreneurialship started becoming more popular.

It’s very attractive, but yeah, like you said, nobody talks about the hard times and how difficult it is and the long nights and the struggle.

Dale: Yeah and I think it’s good that people are starting to talk about that more and it’s becoming a safer place for people to talk about what’s hard and what their fears are, but I also think that the funding environment is such that it biases people to make choices that lead them to take actions that are more stressful than building something that’s small and just them with a number of contractors. I think that’s interesting and more of a comment on a the scale.

The flip side and the thing that I think that I did that was really good was that I focused on building on a personal brand somewhat unintentionally before actually starting the company, so that when I started the company there was already a full upper immediate customers. They already had massive personal network built out, so it made starting the company easier.

Chris: How did you go about doing that?

Dale: I spoke at a lot of conferences which was funneling great when I was 19 and now getting on planes to fly to conferences it’s like, “Not just really.”

I have the number of miles that I've flown  in the last two years consecutively which has been great for my personal life and health and well-being but wasn’t a great way to spend my 19s a 20s.

The other thing I did was start with revenue. We didn’t raise capital until a year and a half into the business as we didn’t need to.

Chris: Nice, so you're generating revenue with the program that you have now before you “Hey, this how we scale up” or what was that message like?

Dale: Exactly. Correct. And so there was a very clear thorough use case for what we were going to raise money for. People could also say that there was a product that worked and I think that’s really key to being able to effectively raise money.

Chris: Yup, absolutely. I love that. Are you in the camp that says focus all of your efforts on one business or one sole income stream or do you like having multiple income streams?

Dale: For my own sanctity of mind, I would like to have multiple income streams. I would say that right now I don’t really have the actual time to develop that.

Chris: Yeah. I imagine being a start-up founder is impossible to focus on much more than what you're doing.

Dale: Yeah. Diversifying my own personal capital has been on my list to do for 2015 which kind of got pushed to 2016. But yeah, when you choose to start a company, you're really putting all your eggs in one basket and that’s definitely getting to a place three years in for the company at least where I'm starting to be like, “Alright, I've put a lot of work in here and haven’t paid myself a ton the last couple of years, I hope this thing is worth something” right?

Chris: What’s your vision for the near future, where do you guys want to go? How many students do you want to be helping?

Dale: We did 10 the first year, 30 the second year. We did about 60 this year and our applications are on track to do between 120 and 150 next year. We absolutely believe that there are many more students out there that we could impact and that the challenges that we really face are around operationalizing and scaling up. We’re going to need to open a second location, as there’s just not enough space for housing, that’s affordable in San Francisco. We’re going to need to hire a bunch of folks.

There are a lot of things that need to happen in the next nine months for that to be realized, and so we’re thinking about what are the sort of medium term thing that we need to do to make sure that we’re in the right place to be doing that.

Does it make sense to raise more capital? I don’t know. It depends on how fast we want to grow and how bullish we are on the market. Do we want to look at places where there could be a really good fit for what we do and would allow us to scale our impact and sort of grow up and graduate as a company and be less of a start-up? I don’t know.

There are a lot of strategy questions that I'm thinking about for 2016 right now.

Chris: Sounds like you guys are at a pretty important spot where you're scaling up and next year should be really interesting for you guys.

Dale: Yeah. It’ll be fun. I'm definitely excited about where we’re going and mostly about the number of colleges and universities who are reaching out to us and saying “Hey, what you're doing is super interesting. We want to start offering credit for the program recommending it to our students.” Those are the ways that what we’re doing starts being accepted by parents as a viable option as college.

Chris: Two more questions. Do you have a favorite quote or mantra that you live by?

Dale: I don’t but I'm surprised at how frequently I get that question.

Chris: Yeah. It seems like half of the people that I talk to are like, “Absolutely. Here it is” and then other people are like, “No, I have just some guiding principles and there’s not one that stands out.”

What does true wealth mean to you?

Dale: I think about wealth not just in terms of monetary gains but in terms of being happy, healthy, having friends and family that love me and feeling like I'm doing something that’s meaningful and impactful in the world. Those are the things that I think about.

Certainly, having money is great but I think it’s also really important to think about that in perspective and to recognize just how privileged we are to live in a country where we generally have access to food, for example.

Chris: I think, looking at you, you were able to pursue what you were passionate about. That alone is such a huge thing that I think a lot of young entrepreneurs take for granted. Every time I hear somebody complaining about the hustle or how hard things are, it’s like, be thankful that you have the ability to do that first of all. I mean, there are so many people that are stuck in jobs that they hate or end up going $100,000 in debt at a college and then realizing, “Holy shit, I just wasted money and I could’ve had a better alternative.”

Dale: Right.

Chris: Yeah, awesome. Well, thank you so much for your time Dale. Where can people reach you?

Dale: You can find more about UnCollege on our site, uncollege.org and you can find me on Twitter, @DaleJStephens.

Chris: Awesome. Well, thanks a lot for your time man. I will let you go and I will let you know when this thing posts.

Dale: Sounds good. Have a great afternoon.

About The Author

Chris Dunn is the founder of Skill Incubator. He is an active investor and entrepreneur with the mission of helping people learn Skills to thrive in today's economy. Chris spends his time testing and building multiple streams of income and investing the profits. Read more here.