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Justin Pincar of Achievable: “It only gets easier, so stick it out”

Achievable is disrupting this industry by producing engaging online courses backed with learning science, and driven by outcome data. You take thousands of little quizzes as you study with Achievable, feeding our learning engine the information required to build and tune a personalized model of your memory. We use this model to optimize the scheduling […]

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Achievable is disrupting this industry by producing engaging online courses backed with learning science, and driven by outcome data. You take thousands of little quizzes as you study with Achievable, feeding our learning engine the information required to build and tune a personalized model of your memory. We use this model to optimize the scheduling of content to improve memory retention, resulting in higher scores with less study time. The more you study with Achievable, the more detailed the model becomes. Since we know precisely what you know and the weighting of the exam, we can predict with very high accuracy how you’ll score on the actual exam before you even take it.


As a part of our series about business leaders who are shaking things up in their industry, I had the pleasure of interviewing Justin Pincar.

Justin Pincar is a technology entrepreneur with over 20 years of experience, architecting products used by billions of people every day and amplifying business outcomes by incorporating engineering discipline. Passionate about education and student success, Justin has designed adaptive learning platforms and learning management systems leveraged by accredited universities and Fortune 500 companies worldwide. He is the founder and Chief Technology Officer of the test prep company Achievable, a technical consultant for businesses of all stages, an engineering mentor, and a chocoholic.


Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

The entrepreneurial bug bit me early! I loved selling lemonade as a kid, and in college, I ran a mini convenience store out of my dorm. After graduating, I landed at a small engineering company that was almost immediately acquired by Boeing. I quickly realized that the corporate world wasn’t right for me, so I left to join a Silicon Valley startup called Admob, and a year later found myself in another acquisition — this time by Google. After spending a year learning from the tech giant, I parted ways and directed my attention to new ventures. During the next eight years, I helped various startups grow from their founding team to their first dozen employees, while also undertaking consulting projects at more established companies. Architecting University Now’s learning management system ignited my passion for EdTech, and constructing Cerego’s memory-backed course development tools allowed me to further my knowledge of learning science. Armed with the insights I had learned from seeing dozens of businesses succeed and fail at various stages of their lives, I finally decided it was time to make the jump myself, and started Achievable.

Can you tell our readers what it is about the work you’re doing that’s disruptive?

The test prep industry hasn’t caught up to this digital age. Printed materials are often years outdated before you even read the first page. If you’re lucky enough to have an online course, chances are it’s nothing more than a web republishing of the physical textbook. Your relationship with the test prep vendor ends the moment you give them your money; they have no idea whether you pass or fail and little incentive to help you succeed.

Achievable is disrupting this industry by producing engaging online courses backed with learning science, and driven by outcome data. You take thousands of little quizzes as you study with Achievable, feeding our learning engine the information required to build and tune a personalized model of your memory. We use this model to optimize the scheduling of content to improve memory retention, resulting in higher scores with less study time. The more you study with Achievable, the more detailed the model becomes. Since we know precisely what you know and the weighting of the exam, we can predict with very high accuracy how you’ll score on the actual exam before you even take it.

Achievable presents a radically new and more effective way of studying. We’re like a personal trainer for test prep — we tell you what to study and when to study, and we know when you’re ready to hit your target score. At that point, all you have to do is show up for the exam and put pencil to paper, and lock in the score you’ve already achieved.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

After about two years working on the business, we essentially had to throw away all our progress and start over. We started as a B2B company, selling test prep to finance companies. The sales cycles were painfully long, but we knew that once we landed a contract, it would deliver stable revenue for years. And after several thousand cold calls, we were able to secure pilots with several big players. What we didn’t expect was that the entire regulatory landscape would change. We only had one test at this point, and the governing body decided that instead of the employer sponsoring the exam and preparing their employees, it would be up to the individual people to study and pass on their own. So *poof* just like that, all our corporate training contracts and all our revenue disappeared overnight.

After we stopped panicking and collected ourselves, we began to realize that our immediate loss was a long-term opportunity. We would have to rebuild our entire platform and marketing efforts from scratch, but so would our competitors. They had the industry connections making B2B growth slow for us, but we’re a more modern company and would be more competitive in the B2C world with a better product and customer service. So we buckled down and started fresh. After a few months, we emerged from the dark with Achievable v2, rebuilt from the ground up incorporating our previous learnings, and specifically for consumers. I’m so glad we didn’t just call it a day when the going got tough — despite resetting our revenue to zero, we’ve since gained a solid consumer customer base and are seeing consistent growth.

Looking back, focusing solely on B2B sales was a mistake. That said, launching in the B2C market from the start would have been tremendously challenging as an unknown vendor with no reputation. And given our limited resources at the time, if we had tried to diversify our business and do both, we probably would have spread ourselves too thin and died that way. If there’s a moral to this story, I suppose it’s that you need to focus on your core value, but maintain some degree of flexibility in providing that value in case you need to pivot or expand to adjacent opportunities.

We all need a little help along the journey. Who have been some of your mentors? Can you share a story about how they made an impact?

When I worked at the mobile ad platform AdMob, they acquired a small company called AdWhirl. I led the integration efforts and worked closely with one of the AdWhirl founders, Ra Roath. I was impressed by the business he had built from scratch, but Ra was such a down-to-earth and normal guy that it took me a while to recognize his depth of experience as a serial entrepreneur.

As we worked together, he opened up about his startup journeys, and I was surprised to learn about all the failures and troubles he had encountered along the way. We always hear about the success stories, but it’s not so often that you get the hard truths about the lowest times in an entrepreneur’s life when all hope seems lost and they’re thinking about throwing in the towel. In that context, one day he told me “you’re the one who decides when it’s over” — that even if all avenues seem to have closed up, it’s up to you as the business owner to decide whether or not you’re going to give it another chance. Sometimes it is prudent to close a failing business, but if you have the will, there will always be opportunities to pivot or try out new strategies.

Ra’s mentorship played no small part in allowing me to persevere and grow Achievable to what it is today, keeping me motivated and sane, particularly during our shift from B2B to B2C.

In today’s parlance, being disruptive is usually a positive adjective. But is disrupting always good? When do we say the converse, that a system or structure has ‘withstood the test of time’? Can you articulate to our readers when disrupting an industry is positive, and when disrupting an industry is ‘not so positive’? Can you share some examples of what you mean?

New doesn’t always mean better in every way. Everyone can agree that Uber has improved the lives of countless people. It’s provided drivers with flexible income and opportunities, brought additional transportation options to low-income and hard-to-travel areas, and generally made the experience of getting from point A to point B by car much easier, more enjoyable, and safer. Uber has undoubtedly disrupted and positively changed the rideshare industry in these ways. But as an unfortunate side-effect of their business success, they crushed many people who built their professional livelihood around existing taxi cab medallion systems. Sure, you could chalk that up to bad investment decisions on the part of medallion owners, or a lack of innovation in the taxi industry as a whole, and those are entirely valid takes. Regardless, Uber’s explosive growth and disruption of the rideshare industry led to some major ‘not so positive’ consequences for many folks.

Can you share 3 of the best words of advice you’ve gotten along your journey? Please give a story or example for each.

  1. Don’t give away your product or service for free. Free users tend to not value the product for what it’s worth, and as such, they most likely won’t be your champions and won’t lead to more users. Opt for a deep “early access” discount instead, as these users will be much more engaged if they have a bit of skin in the game. They’ll also be more willing to give you honest feedback to improve your offering and be more forgiving if there are any issues. When we gave out our SIE course for free at launch, no one used it or gave any feedback… they saw it as a fun new toy rather than a necessary tool. We changed up our strategy for the next exam, the Series 7, charging half the price during development, and ended up getting dozens of organic sales and loads of invaluable customer feedback before we had even officially launched the course.
  2. Reach out to your network. And by your network, I mean every single person you can get in front of, both physically and online. You’ll get some early customers from it, but more importantly, you’ll make a lot of new connections and get great advice. You’d be surprised how many folks will show up just wanting to help you achieve your dream. We’ve gotten so much help from our networks that I couldn’t possibly list everything… but off the top of my head: customers, business partners, interns, venture capital introductions, office space, office equipment, design work, copy edits, and an absolute ton of very thoughtful feedback and advice from a wide variety of different backgrounds and perspectives.
  3. It only gets easier, so stick it out. Starting is the hardest part since you have nothing, and everything seems like a daunting task. But from here, every email you write, every single piece of marketing collateral, every product feature — they all build up and add to your arsenal. You’re always better armed than you were the day before, and that makes it just a little bit easier. This is particularly relevant when it comes to content production. Creating something for the first time, whether it’s a visual asset or a new piece of copy, always takes longer than expected and rarely turns out as good as you hoped. But once you’ve done it that first time, you can “remix” it and use it as a base for the next piece of content. With that extra time, you can go a little further on the new piece, and then use that new one as the base for your next piece, and so on. Before you know it, you’ll be producing robust and professional content in a tenth the time it took you at the start. You can see this progression very clearly by the quality of the images in our blog — our first, basic graphics took hours to produce, and now we’re making far more sophisticated ones in under twenty minutes.

We are sure you aren’t done. How are you going to shake things up next?

We’re continually improving the Achievable platform and learning engine, but our next big focus is on expanding our exam catalog. We currently have courses for three exams: FINRA SIE, FINRA Series 7, and the GRE. We’re actively developing a USMLE (medical) course, and we’ll have that live within a few months. Early in the new year, we’ll release additional FINRA courses, so as finance folks grow in their careers they can continue to use us for their licensing prep. We’re always on the hunt for new opportunities that align with our mission to help students pass life-changing, high-stakes exams. We produce our courses by partnering with subject matter experts such as corporate training professionals and tutors, and these folks tend to be in high demand and keep themselves busy. We’re opportunistic with our content roadmap in order to work with the most talented people.

Do you have a book, podcast, or talk that’s had a deep impact on your thinking? Can you share a story with us? Can you explain why it was so resonant with you?

The book that has been most impactful for me is “Getting More: How to Negotiate to Achieve Your Goals in the Real World” by Stuart Diamond. It’s hands down the best business book I’ve ever read. Most negotiation books focus on short-term wins, usually at the expense of the other party. Getting More teaches you that negotiations are not zero-sum games, and that if you’re thoughtful and creative, you can generate additional value that didn’t exist before. That’s why it resonates so much with me — I don’t want to “get more” if it means someone else is getting less.

One example that comes to mind is how to approach salary conversations. You still need to have the basics down: know your experience and market value, and the worth of your skills to your potential employer. Salaries are usually benchmarked or capped within a range, so there’s not much room to negotiate. Getting More trains you to discover the hidden gems that each party can offer, and it’s a bit like a treasure hunt. You might have colleagues or connections in other fields — and these intros are easy for you to make while providing real value to the company. Having a specific title might be important to you for career development, and it likely costs nothing for the company to make that change. They might be hesitant to increase your base salary, but be comfortable giving you a stipend to buy your own equipment. There’s a world of possibilities that you start to unlock as your thinking shifts from competitive to collaborative. The best part is that after a discussion like this, you and your counterpart will end up understanding each other’s goals much better, leading to a stronger long-term relationship, and both of you getting even more in the future.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“Accept that everything is a draft.” — The Cult of Done Manifesto by Bre Pettis and Kio Stark.

I don’t consider myself a perfectionist, but there are far too many times when I find myself rewriting and rewriting marketing copy and emails, spending hours on a task that should have only taken a few minutes. The problem is that it’s never “done” — no matter how good my work is, I know that it can still be improved. Considering it a draft reframes the task. I no longer need to create a masterpiece that will live forever — I just need to make a “good enough” version and call it done, for now. I tell myself I’ll come back to it someday… and often, someday never comes, and that first draft ends up being “done” after all.

The Cult of Done Manifesto hasn’t entirely saved me from myself, but after printing it out and hanging it on my wall, I tend to catch myself and break out of these ruts a lot faster. There’s a lot of good little bits in there — check it out and see which ones speak to you.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

I’m passionate about open education and open educational resources, and would love to further those causes. It may seem odd for the founder of a test prep company to campaign for free access to material, but it aligns with our corporate vision as well as my own ideals. I believe that content is ultimately a commodity. The way it is presented may vary from vendor to vendor, but the information itself will always be about the same. Achievable’s textbooks are first-rate, taking hundreds of hours to produce, and we’re quite proud of them. Despite that, we’d made every page of textbook content searchable on Google, and you can read through it cover-to-cover without paying a dime — we want learners to have the core content for free. It’s for value-adding premium features like advanced personalization, accelerated study programs, and enhanced analytics that we feel it’s fair to charge a fee. I’m hopeful that other vendors follow in our footsteps and open up free access to their materials.

How can our readers follow you online?

LinkedIn — https://www.linkedin.com/in/justinpincar/

This was very inspiring. Thank you so much for joining us!

Thank you for the opportunity 🙂

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