The #1 Challenge Tech Startups Must Overcome

by / ⠀Entrepreneurship / January 20, 2015



Challenges never stop when starting a business. While trying to break into the startup world, I learned as much as possible about startups, founders, networking, investing, and anything related to entrepreneurship. I interviewed founders, made cold calls and emails to entrepreneurs I respected, and even snuck into a premier event to meet my idols in person. Getting this information and feedback helped me build a strong network of mentors and advisors that eventually led to the creation of ONE.

When speaking to and working with other young entrepreneurs, I encourage them to ask questions and seek information. Out of hundreds of questions, I respond to every one of them personally. Many of these questions come up frequently, so I have started answering these questions in a Q&A series — #AskCory (Text questions to 650-646-5389 or tweet them to @Cory). I recently received the following question:

Question: As a startup, what has been the hardest barrier to overcome?

Answer: Product/market fit is by far the hardest barrier to overcome.

Marc Andreesen defines product/market fit as “being in a good market with a product that can satisfy that market.” He also refers to it as “the only thing that matters for a new startup.”

Steve Blank: “Customer Validation proves that you have found a set of customers and a market who react positively to the product: By relieving those customers of some of their money.”

Building something that not only has demand, but also provides the correct experience for that market is a very difficult feat to pull off, especially in a consumer-driven world. Without finding the right fit, it doesn’t matter who your investors are, how much talent you have on your team, or how unique your idea is. If you are not filling a solid need in a strong market, you’re the captain of a canoe going upstream with a hole in the bottom and without a paddle.

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Is there a fit?

Product/market fit is something that is hard to define, but you know it when you see it…or do you? While speaking to Daniel Gross, who sold Cue (formerly Greplin) to Apple for an estimated $40 million, he compared finding the right product/market fit to love. Even when you think you’ve found it, you still may question it and not be 100% sure that you’ve found it.

Through many iterations and several products, including the ONE app and After School, we are still working on making sure we have the perfect product/market fit. All of the signs and signals look like they’re pointing in the right direction, but we’re being optimistically careful and avoiding forcing a fit, which can turn into a disaster for your business.

There are many well-funded companies that are still searching for the perfect fit several years and millions of dollars later. This isn’t part of the process you can force.

How can I fit?

Although knowing 100% if you have the right fit isn’t easy, there are several ways to determine if you’re on the right path.

  • Engagement Levels

How’s your engagement going? No, I don’t care about your personal dating relationship. Are users engaging on a daily basis, or do you have 30,000 ‘users’ with only 500 that use it more than once a week? Iterate until you get active engagement among your users.

  • User Love

What are people saying about you? Are your customers knocking down your door to compliment you and tell you how amazing you are? Verbal affirmation is important in any relationship, and a positive sign that both parties are happy with each other.

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Where to look?

  • Twitter – Are you trending for a good reason? Are there @ mentions about how awesome your app is? We all get into arguments once in a while. Although you will always receive some hate on social media, if you are getting a wealth of positive vibes compared to negative on Twitter and other social media outlets, chances are you are on the right track.
  • Emails – Unsolicited praise flowing into your inbox is a great sign. Not only can you get additional feedback and use these comments as testimonials, it allows you to build a relationship with those who are already in love with what you provide, or turn things around if you are getting negative feedback.
  • Stories – Storytelling is big business, just look at Hollywood. If you’re hearing stories about how your product or service impacted someone’s life or made a significant experience possible, then that needs to be shared and is another strong signal.
  • Reviews – Tracking App Store reviews is important. Consider all feedback and the individual comments more than the star rating. Reviews are direct feedback from users, and a good measuring stick.

If you aren’t sure if you’ve found the right fit — you probably haven’t. Keep working to find the right fit until your users/customers can’t stop using and sharing your product.


Cory Levy is the Co-Founder and COO of ONE — creators of After School and the ONE app. ONE has raised millions in venture capital from Charles River Ventures, SV Angel, General Catalyst, and others.  After School is an anonymous social sharing platform that allows high school students a safe and fun place to share their voice. The ONE app is a mobile application that lets you know when there are people right next to you who share your interests. Cory took an absence after studying CS at the University of Illinois to start ONE. Connect with Cory on Twitter.

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About The Author

Matt Wilson

Matt Wilson is Co-Founder of Under30Experiences, a travel company for young people ages 21-35. He is the original Co-founder of Under30CEO (Acquired 2016). Matt is the Host of the Live Different Podcast and has 50+ Five Star iTunes Ratings on Health, Fitness, Business and Travel. He brings a unique, uncensored approach to his interviews and writing. His work is published on, Forbes, Inc. Magazine, Huffington Post, Reuters, and many others. Matt hosts yoga and fitness retreats in his free time and buys all his food from an organic farm in the jungle of Costa Rica where he lives. He is a shareholder of the Green Bay Packers.


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