Lemons to Lemonade: This Entrepreneur Turned a Frustration into a Thriving Online Business

How Andrew Chaifetz created Notebowl

Andrew Chaifetz approaches life with an inquisitive eye. Never one to accept the status quo, Andrew’s foray into entrepreneurship began in college when he was required to use a clunky, outdated learning management software (LMS). He decided it wasn’t enough to be frustrated and write it off for someone else to eventually tackle. Instead, recognizing others shared his experience, Andrew seized the opportunity to improve and upend the LMS industry. And this formed the basis of Notebowl, a sleek and user-friendly social learning platform for higher education that brings courses and the campus community together –– all in one place.

In this episode, Andrew talks about navigating different stages in his business, why he approaches even the toughest challenges with a positive attitude and why our humanity hinges on people asking, “Why?”.

Tell us about what Notebowl. What exactly is it?

Notebowl came from a frustration of working with learning management systems. On our campus, we used these LMSs that were really archaic, while at the same time using Facebook and Twitter and Snapchat on a daily basis. I said, “Why can’t we have that same type of user experience for our student experience on campuses?”

Notebowl came out of that idea of bringing social media into our learning environment – not only into our classrooms but also out of the classroom experience and with clubs or organizations on campus. We wanted to bridge that gap, bring those two areas of a university, your extracurriculars and your academics, into one place. We call it a social learning platform and it encompasses a full learning management system and social network onto one place. Kind of a Facebook of academia.

Now as CEO of Notebowl, what do you do in your role?

As an entrepreneur and CEO, you wear many hats every single day. You’re working on operations, sales, marketing your product, investment, HR – everything. You’re kind of the cheerleader for the whole team.

You launched into business ownership during school. What’s one thing you had to train yourself on or learn as the CEO?

There’s a lot of things that you never really know the exact answer to until you do it. You really have to have a mindset going into building a company that you’re not going to know everything. You need to go in and say, “I need to learn a lot of things. I’m going to be learning in the public eye. Going into meetings I’m going to be learning. I’m going to be finding out new things. I’m going to be constantly building myself.”

What are some of the biggest challenges you’ve faced as you’ve scaled the company?

It is critical to focus and be positive because you can easily go the other way. I think that’s kind of a world view, too. Do you see the glass half full or half empty? Everyone can do it differently, but for me I think positivity helps take the company to great heights and helps people want to connect with me.

What’s next for Notebowl?

It’s really about growth, scale and constant iteration. We are in a growth stage, so we have to have a different mindset. How can we be more efficient with our processes? How can we create new processes and constantly iterate those processes as we go? How do we scale up from just me and a couple of people on our growth team to 100 people or more? We need to think about how to scale our employees, our team, our processes, our product, our onboarding, our customer happiness packages that we send to customers, and how to automate things while also making it personal. It’s extremely exciting, going from pre-revenue to revenue to serious revenue generation.

What’s one piece of advice you would give to fellow entrepreneurs?

Beyond just the initial positivity, it’s also about asking why are things the way they are. Really ask why. You need to be the person that raises the hand in the lecture hall. You need to be that person that questions something that is considered the norm because then you’ll understand the world better and can build better things that solve problems that help move our world forward. If you ask why, you start to uncover all the problems that exist and look at the problems as opportunity. If you look at and you ask why and you see all the problems, you see the opportunities, then the world is like this open place to do whatever you want with it.


Lightning Round Q&A:

Are you a coffee drinker, yes or no?

Yes, I am. I’m drinking coffee right now.

What’s one business tool you’re geeking out over right now?

Intercom. Great tool to use for customer support and automation of marketing as well as sales.

What’s one favorite piece of technology?

Tesla and SpaceX. Elon Musk in general.

Is there one book that you would pass along to a fellow entrepreneur?

My uncle’s favorite book, The Endurance. It’s Shackleton’s journey, basically, into the Arctic. So a good book to talk about perseverance and overcoming challenges and thinking with a positive mindset.

Who’s one person you would like to have dinner with?

Elon Musk.

How many hours of sleep do you get each night on average?

I do track my sleep with my Fitbit. It’s around seven hours on average.

Connect with Andrew at: hello@Notebowl.com