This NYC Startup Raised $4.25M to Expand Online School and Offer Career Services



We all know that Peter Thiel thinks college is expensive and a waste of time – at least for some people. Well, here’s an interesting twist. Thinkful President and cofounder Dan Friedman was an inaugural member of the Thiel Fellowship program, and Thinkful is the education company that teaches coding and design through online mentorship, meaning, it is experts in their respective fields who are teaching students. It must be working. Thinkful announced that it has raised an additional $4.25 million in funding led by Floodgate Fund, with participation from existing investors RRE Ventures and Quotidian Ventures.

And the company, which grew 5-fold last year to over 3,000 students, has built the largest global network of software engineers to mentor students 1-on-1 as they learn technology skills and pursue career changes.

Now Thinkful is taking it to the next level, adding a career services component as the next step in building its disruptive model for career education.

“Traditional, classroom education for engineers simply doesn’t work, especially for adults with full-time jobs,” says Darrell Silver, the company’s CEO and other cofounder. “We’re creating a learning process that can evolve as quickly as technology changes. Having a great mentor is proven to be the best, if not the only way to become a true expert; we built Thinkful around that idea.”

By equipping graduates with job-ready skills, Thinkful proves that teaching through online mentorship is a strong solution to the rising costs plaguing traditional education. Silver tells us more about the funding process, the new career services component and what else it is that sets Thinkful apart.

Who were your investors and how much did you raise?

The round was $4.25M seed round, led by Floodgate, with Ann Miura-Ko joining our board.

Tell us about your service.

Thinkful is the best way to advance your career without disrupting your life, taking on debt, or quitting your job. We have a network of over 250 professional software engineers around the US who work with students one-on-one in each course.

How is it different?

Our mentors are practicing experts in the fields in which they work with students. Unlike other online education, which is also quite flexible, expert help is really what keeps people engaged and focused. Ultimately, it’s the key to learning. We see incredible retention from students because of them, and real relationships are born because it’s all one-on-one.

Tell us about the career services segment that you’re launching.

Each new student to Thinkful will receive career services. This means that a professional recruiter – the same type of person our students will be interviewing with if they’re looking to change jobs – will help students prepare their resume and receive live, one-on-one interview prep. That’s in addition to our students’ existing professional mentor. From what I understand, there’s no one providing nearly that level of one-on-one service, online or off. And we’re doing it only for a few hundred dollars a month.

Darrell Silver, Dan Friedman

Darrell Silver and Dan Friedman

What are the most popular programming languages at the moment?

We saw incredible pickup of Apple’s Swift language when it launched in the middle of last year, though that may have been because we were the first in the world to offer that course. We could do that because we already had a mentor team and expertise in Apple’s objective-C, which came before Swift. Now we’re seeing a lot of excitement around Data Science, and our new Android course, which just launched last week.

What market are you targeting and how big is it?

When we started I got this question a lot, and responded, “well, it’s for anyone not satisfied in their current job.” Nowadays fewer people ask me that question, so I guess everyone heard the answer!

What’s your business model?

All of our courses are self-paced, so we charge students directly for each month they’re enrolled. It’s not like a lot of 3-month programs that go at one speed and end regardless of your progress. We believe in personalization. If you can go faster, you’ll spend less, and if you need more time, or need to pause, it’ll take longer.

What was the funding process like?

Dan and I worked hard on funding until we found excellent partners in Ann Miura-Ko and Mike Maples, Jr. of Floodgate Fund. Ann’s experience in education and communities of people working for a mission is perfect. And Mike’s intuition and experience around sales is unparalleled. Our existing investors, RRE, Quotidian, Founders Fund, and others, were also extraordinarily helpful. But make no mistake: it takes a lot of time to do well.

What are the biggest challenges that you faced while raising capital?

Perseverance. We have 25% monthly growth, a killer pitch and a great network, but these things have a natural lifecycle to them. Knowing where we were going was easy; finding partners to share that roller coaster with us was much harder.

What factors about your business led your investors to write the check?

Floodgate has a long track record of investing in movements. They’re in TaskRabbit and Lyft, among many others. I think Ann and Mike also looked at us and believed we could execute a difficult product in a competitive space, all while listening to our investors and our market.

What are the milestones you plan to achieve in the next six months?

It’s time the online education world grew up. At this moment, our mentor network represents over 1,000 years of experience in their fields. That’s just incredible. So it raises the question of how far they can take us. We think, basically, that while a lot of companies are creating new types of degrees, that really all they’re doing is lowering the bar to something they can call success. That won’t work long-term. Instead, success should be measured by students reaching their goals, balanced with their time spent learning and the affordability of the program.

In the next six months we’ll be introducing more programs like career services that really do make this possible.

What advice can you offer companies in New York that do not have a fresh injection of capital in the bank?

Talk with more people. I’ve been in tech in New York for seven years. Someone who’s more naturally social could meet the same number of people as I know in less than half that time. For the last six, I have run an annual holiday party for small startups called StartupXmas. It’s an incredible event, but doesn’t get bigger each year. Instead, I get closer to the old friends and meet more new ones. That’s New York. A small, accessible and powerful community.

Where do you see the company going now over the near term?

Career services is just the beginning of our efforts to bring accountability to alternative online education. But there’s so much more to do. For example, around 20% of students have their employers paying for courses. That’s a large number. Maybe we can turn that into half the business, or more.

Which is your favorite New York craft beer?

Brooklyn Lager.

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