Greg Kaplan

Be open to pursuing new opportunities.


Greg Kaplan is the founder of CollegePath, the first free mobile app that provides custom weekly college admissions advice tailored to a student’s interests, goals, and activities for every step of the college admissions process. He is the author of Earning Admission: Real Strategies for Getting into Highly Selective Colleges and has helped students earn admission to some of the most selective colleges in the country including Penn, Duke, Cal Tech, and Columbia. A former investment banker, Greg is following his passion to help others by applying their education to their passions

Where did the idea for CollegePath come from?

The idea for CollegePath came from my belief that everyone deserves a plan to succeed in the college admissions process and realizing that one-on-one coaching of individual students is not enough to address a stressful process facing millions of families. .

What does your typical day look like and how do you make it productive?

A typical day starts around 6 am with a drive to the gym. I don’t have much time for myself right now, so if I don’t squeeze it in at the beginning, it won’t happen. The best way to describe my days are shifting from project to project. I meet with several students in a given day and block out time to work on marketing or refining our product. I rely on scheduling blocks of time for each different project or appointment to keep the day on track and make sure that I do not waste time by letting any task drag for a time longer than it should.

How do you bring ideas to life?

I like to sketch things out, refine them, write about them in emails to myself, and then start pitching family/friends, team members and existing clients that I trust.

What’s one trend that excites you?

The student loan crisis is forcing families to treat a college education like an investment. Families are proactively seeking ways to maximize their return on investment by ensuring that their kids minimize costs and maximize career opportunities upon exit.

What is one habit of yours that makes you more productive as an entrepreneur?

I turn off my WiFi when I am writing or need to focus and keep my phone on do not disturb.

What advice would you give your younger self?

Be open to pursuing new opportunities. Through college and the first five or six years after graduating, I fixated on finding opportunities in existing fields where there was little opportunity for disruption. Looking back, I would tell myself to find opportunities that seemed contrarian or not trendy in the moment.

Tell us something that’s true that almost nobody agrees with you on.

It is important to make everyone in the room feel part of a conversation. Even if a person is not asking questions, they may be the group influencer or decision maker. Draw them into the conversation with eye contact or personal references. Do not keep responses limited to the person asking you a question.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

I do a lot of speaking events with schools and organizations seeking guidance on the college admissions process. The one thing I hear when someone decides to work with my company or inquire about our services is that they hear the passion in my voice when I talk about education. Entrepreneurs are part of their brand, and people respect the fact that I am dedicated to mine.

What is one strategy that has helped you grow your business?

Create brand credibility as possible through speaking, blogging, contributing articles to media outlets. People want to get to know who a company was created by and why it was created. I share who I am with so people understand the story of CollegePath and why it fits in with their life. Initially I tried not to share anything about myself, but people constantly would ask where the expertise or service came from. Even if in the mobile app business, people still crave a personal connection with a company.

What is one failure you had as an entrepreneur, and how did you overcome it?

I outsourced the initial version of CollegePath to an American development agency. I knew little of the development process and relied on them to make technical decisions. I did not realize that those decisions were strategic in nature, and at the end of the day had a product that was not what my customers wanted to use.
I hired developers who work directly for me and educate me on technical issues so I can make informed decisions and collaborate with them on technical developments.
At first, I was nervous to be directing strategy for an area I was unfamiliar with. I overcame this by asking questions about everything I did not understand.

What is one business idea that you’re willing to give away to our readers?

Today’s students are under incredible pressure to achieve the best grades possible. 47% of college bound seniors have ‘A’ GPAs. Academic tutoring is in demand with enormous growth potential. Whether it is tutoring in a foreign language, improving writing skills, or helping with math or science homework, there are ways to tutor in an area that is your strong suit based on professional or academic training.

What is the best $100 you recently spent? What and why?

I booked a flight from LA to Portland for $120. I spent three days driving up and down the Oregon Coast to recharge and disconnect from my business. Entrepreneurs need to give themselves time off and prioritize their mental health. I felt amazing returning home.

What is one piece of software or a web service that helps you be productive? How do you use it?

I stopped using MS Office for documents and spreadsheets with my team in favor of Google Docs and Sheets. There is no time wasted with waiting for input or revisions and we do not run the risk of version control with updated files.

What is the one book that you recommend our community should read and why?

The Four Hour Work Week” by Tim Ferris. This book is what inspired me to assess what my unique skillset was and how I could offer it to the world and build credibility in the field of college admissions advice. Ferris offers incredible tips for people to start a businesses with free and low cost resources to leverage their time.

What is your favorite quote?

I never found beauty longing for the impossible and the possible beyond my reach.” Atlas Shrugged, Ayn Rand.

Key learnings:

  • Block time for manageable tasks that can be accomplished in one or two hours of time.
  • Switch projects to engage different parts of your brain.
  • Carve out “me time” to ensure you are mentally strong.
  • Ask questions until you understand an issue that you do not. Being a founder or entrepreneur does not mean you need to know everything—just that you need to know when to ask questions. The only bad answer is one that doesn’t make sense to you.


CollegePath on Facebook:
Greg Kaplan on Instagram : @collegegurugreg
CollegePath on Instagram: @collegepath