Interview with Tyler York
Tyler York is the cofounder and CEO of Achievable, a modern, guided and personalized exam prep that delivers better test results through adaptive learning technology
Tyler York is the cofounder and CEO of Achievable, a modern, guided and personalized test prep that delivers better results through adaptive learning technology. He graduated from the Carnegie Mellon Tepper School of Business in 2010, where he met and roomed with his Achievable cofounder, Justin Pincar.
We sat down to hear about his journey to becoming a founder and how his experiences at Carnegie Mellon University led to what he’s working on now.
Let's start by hearing a little about you.
I went to Carnegie Mellon as an undergraduate from 2006 until 2010, and was a part of the Tepper School of Business. Today, I run Achievable; I'm the cofounder and CEO, and that means being a jack of all trades, doing all sorts of things; from content marketing, paid advertising, SEO, social media, influencer marketing, business development, and sales.
Achievable is modern, guided and personalized exam prep that delivers better results in less time. And the way that we do that is through adaptive learning technology, built around a method called spaced repetition.
Spaced repetition is the idea that when you study matters just as much as what you're studying or how you're studying.If you study at the right time, you're more likely to remember things in the future. But rather than having a spreadsheet filled with all the flashcards you've ever used, we automate everything with a very powerful learning platform. For our customers, we are a defined and efficient path to ace their exam.
Before Achievable, I actually most recently was in the video game industry at GLU, running product marketing for Tap Sports Baseball, helping grow it from $74 million to $104 million in revenue per year in two years, and making it the number one licensed mobile sports game in the United States. GLU was then acquired by Electronic Arts in 2021. After the Electronic Arts acquisition, I left my role to go back to being full-time on Achievable with Justin.
One thing I love about the product marketing role is that you’re involved in 30 different things. I was responsible for athlete relations, licensing relations, creative and user acquisition, live operations, and working with the product team, as well as social media marketing, and things like the app store page.
I feel like there is some relation there, especially in the games of the 90s, where there was so many more educational games, and a lot of experimentation. Did that inform some of what you've developed?
Earlier in my career, I was in business development for companies that were selling to game developers. So I talked to a lot of small game developers who were making educational games. I've probably seen about two dozen companies try to do them, and none of them ever made it. Education and games make sense at a conceptual level, but I haven’t seen a big successful one yet, though maybe I’ve missed it.
But engagement is important. Even feeling a sense of progress is really important. People need to feel motivated, so that their goals are achievable. Doing the work is really important. And those things are translated across both game design and education product design. We want to make sure we're building an engaging experience that people feel like they can accomplish. With Achievable, we accomplish this with core product design and not fluffy gamification add-ons.
Gamifying education has been a big topic for a while now, so we made sure we looked at it. We didn't do a ton of fluffy gamification, we just did the most important things.
How did your education make you successful in your career?
I went to high school in New Hampshire at Exeter. It’s a very unique school, and they teach what's called the Harkness Method, where students debate, and the teacher is the Moderator. So instead of a normal math class where the teacher goes up and tells you how to do problems, they'll assign you the problems, you try and figure them out, and then you debate your solution with the class. So the other students will tell you what you did wrong. And they applied this to everything: English class, economics class, you name it. That was probably the first and most formative thing for me, because it taught me how to assert myself and be convincing, which is a very useful skill.
And then when I toured Carnegie Mellon, I loved it. I actually early admitted. I really liked how it was okay to be a nerd. And as an anecdote to this, I remember when I was there, Optimus Prime was the #1 voted-for for student council president every year, and whoever got second actually got elected. I love stuff like that. I've always been a huge nerd, and Carnegie Mellon made me feel like I could do that and be successful.
Another thing I love about Carnegie Mellon is that Carnegie Mellon people work hard. Sometimes, I feel like there’s a chip on our shoulder that motivates us. And then a part of it is from the Dale Carnegie, “my heart is in the work” motto. You should be working on something you can put your heart into.
What were some the most memorable and values courses or activities you took part in while you were at CMU?
Being part of a fraternity was great. I enjoyed the brotherhood and all the fun things we did together. There are a lot of projects and things like Buggy that were really cool and unique to CMU. A friend of mine was the leader of the winning KKG booth team one of the years I was there, and she always said that was one of the coolest things she did in college.
And then there’s two classes that stick out to me. One of them was Management Game, which I thought was incredible. And the other was Intro to Entrepreneurship, which was a formative class on my journey to becoming an entrepreneur.
So Management Game, everyone in Tepper should know. It’s a required class for everyone in senior year. You're running a spreadsheet “business”, and there’s even a “stock market”, where you can buy stock in your peers and bet on who you think is the most successful in the class. And your company has a “stock market” value based on how well it's doing. You even met with a “board” of local CMU business leaders every month. It was an incredible experience.
And then the other one that I loved was the Intro to Entrepreneurship. In that class, the teacher gives everyone a $1500 check in their personal account, and he says "Your goal is to make as much money as possible with this money that I've given you, and nothing else." No outside money, you can't do anything illegal, and everything you do has to be tracked. So you don't just add $2000 of your own money. And if you reach certain thresholds, if you double your money, or two and a half times, to $3500 or $4000, you got an A. And then everyone’s earnings from the whole semester went into a pot, and whoever made the most money wins the pot.
And then if you got an A, and went over the threshold, what do you do with the rest of the money? That's the game. If $4000 gets you an A, do you keep the extra money, or go for the grand prize? The winning team usually makes $7,000 to $10,000, which is good winnings for undergrad students. It was a ton of fun and if I ever become an adjunct professor or something someday, I’d love to have a class like that.
When you're asked to start a business that's gonna make money right now, what can you do? We were talking about being a beer delivery service, where we go to the liquor store and deliver it to you. But that was very not legal, so we had to scrap it. We talked about basically being our own GrubHub, we tried a bunch of stuff, and we ended up selling T-shirts and hot cocoa during the cold.
We got an A, but didn’t win the whole competition. My friend the following year won - I love their story. His team rented a bunch of buses to take people to the Stephen Colbert rally in Washington, DC. They charged people $40 for a bus ride there and back, and the bus rental was around $800. They had packed buses, about 50 people each, and then took that money and made T-shirts for the rally and sold them on the bus. They ended up winning with a submission of about $10k - I love their story because they were pretty creative.
In another interview, you mentioned that the idea for Achievable came from your cofounder, Justin Pincar. How did you two meet?
Justin and I were both in the same fraternity, and we were roommates for my freshman year and sophomore year. We were super fast friends and became roommates pretty quickly. And as we got along really well, we were clearly a good team. We had a shared dream of being entrepreneurs, which was a pretty sexy thing in 2007. Justin was very enterprising; he joined a couple of startups as a college student.
We then went on to start a couple of our own companies right after college. For example, we started a daily deal site for food. That went okay until Gilt Taste launched and completely wiped us out. Then we tried to start an ad network. Eventually, we went our separate ways; he went into tech, and I went to mobile gaming.
Justin graduated in 2009 and went to work at AdMob, an independent ad platform that later got acquired by Google in 2011 for $750 million. And at the time, that was a monstrously huge acquisition. Everyone who worked at AdMob could get a job at any VC they wanted. Most of them did. And it was a huge win at that point in the market. Justin, was in charge of AdMob’s AdWhirl mediation platform completely. He scaled it to a billion impressions per day. That's a massive service to manage even for industry experts. And he was 24 at the time. He then went to Google, but he didn't really like the big corporate life. In that period, he really found his passion for education and then went into EdTech.
He was then the founding engineer and platform architect for a company called UniversityNow, which was aiming to be a for-profit college that didn't take student loans, so there was a social good aspect. You're trying to charge people $500 a month upfront, instead of getting them into debt. Unfortunately, that business model ended up not working out. Then he went on to another company called Cerego, where he largely rebuilt the product, did a bunch of hiring and ran the engineering team.
Cerego was where Justin learned about spaced repetition and how powerful it could be for students. Cerego’s primary business model was to provide a spaced repetition-based adaptive learning module for large textbook publishers. But unfortunately, in spite of investing millions in the projects, these publishers couldn’t get students to use these supplementary products. Justin told Cerego he believed they could do a better job if they vertically integrated the content and platform into a single offering, offering the full textbook, with the spaced repetition-backed questions and practice exams. But the stakeholders of Cerego wanted to focus on being a technology platform, which is pretty reasonable. So he left the company, took a bit of a breather, and then called me up. I left my job at the time and we got started with Achievable.
This was in 2016. We researched a ton of markets, and found that the FINRA test market had a particularly painful status quo. The pass rate was only 65% for the FINRA Series 7 exam; and if you failed, you get a second try, but if you fail twice, you get fired. So, if you do the math, 15% of people get hired, spend 90 to 120 days trying to pass the test, fail twice, and get fired. Customers we spoke with said that that failed candidate costs the company around $50,000 per person. So, imagine a big firm, hiring thousands of people per year, that’s millions of dollars in sunk costs we could potentially solve.
We've been building this since 2016, and we've been bootstrapped all the way up until December 2021. We needed full time jobs to pay the bills, which is why I was at GLU/EA until we were able to raise a pre-seed round. Now our business is doing well, breaking new records every month.
What are some of the main challenges you've had?
The biggest challenge that we had was at the end of 2018. We were originally servicing an exam called the FINRA Series 7. And that exam got broken in half by the regulatory body.
FINRA aggregated the standard material across all these different exams that they have into what's now called the FINRA SIE Exam, or Securities Industry Essentials Exam. This was a big and welcome shift. Another change they made is that you can take the SIE Exam before you find a job. Previously, the paradigm was you had to get a job, then you had to go to take the test, and then you know, 35% of people fail, and then you had to take it again. And FINRA knew that was a problem too. So they made an entry level exam meant to be taken before you apply for jobs.
This was a great change for the industry, but it was tough on our business. At the end of 2018, when that test came out, we lost all of our customers, because all of our customers were using our Series 7 material. And with this new change, they essentially said, “we're going to take a wait and see approach, and we're going to put you on pause.”
We had to make a choice. We could either quit and wrap it up, or build for the new paradigm.
And we opted to do that because we saw how the SIE was actually a great opportunity. The FINRA test prep market at this point was almost entirely B2B, because people had to be sponsored to take their Series 7. And this was a very risk averse area, because a lot of these firms aren’t trying to take risks on test prep for licensing. So it was really, really hard to get B2B sales. We cold called for nine months straight to find customers. And we were successful - we had some big customers, including three of the top five wealth management firms in the United States. But this new market shift meant that people would be buying the FINRA SIE as a consumer, which meant our product could win on its merits.
We rebuilt Achievable from the ground up for a direct to consumer business model. We incorporated a free trial, built out the consumer facing marketing, and basically rebooted the company. And then, in 2020, we took the product foundation Justin had built, and started applying it to other tests. We added the GRE, USMLE Step 1, AMC, and we've continued to add more. Since then, all of our lines of business have been performing extremely well and we have a great diverse revenue base. And now, because we have so many happy customers, we're getting inbound interest from businesses on the FINRA side, coming full circle. The product is excellent - it's just a matter of getting it into people's hands.
Was there any effect from COVID hitting as you were starting to pivot?
The first two months of COVID, we took a sizable hit because everybody stopped buying and hiring. However, not long after that, things started to pick up again, and quickly. By the summer, there had been a shift to online learning, and we had launched our GRE and USMLE courses. Each of our products has grown quickly and stacked on top of each other. I don't know how much of it is COVID and how much of it is being a young company, but I do think that COVID changed the way that people learn forever by making people more comfortable with online learning.
Who is on your personal list of advisors?
My former manager at GLU, Mitch Solomon, is a really good one for me. And also my former boss at Cloudcade, Nic Ingham. They're both people that I could ask about anything, including marketing. But my advisor for a lot of stuff is actually my cofounder, Justin. He’s seen startup go from five people to 120 people, he's been through a startup acquisition, and he is actually a startup advisor and angel investor as well. He has a great perspective.
Are there any reading recommendations you have for first time founders?
Paul Graham essays are really good if you're trying to start a company or you're just interested in what it takes to do startups. OG YCombinator was one of the most powerful forces in Silicon Valley, and I feel like their secret sauce is just a laser focus on what's important.
And I really like some of Chris Sacca’s essays and the interviews he's done, particularly where he talks about when he was struggling, and how rebounded when the market crashed in 2001. He was working, trying to make ends meet, and then he said, “I want to go on the offense, I want to stop playing defense.“ I think about this quote a lot with my own life and challenges.
If you're going to start your own company, you should be thinking that way. What do I need to do to start working on this? What are the paths available to me? How do I make it happen? There will never be a perfect time.
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