Looking For Problems To Solve

Catherine Yushina
Startup Mortician
Published in
7 min readJun 24, 2020

Today’s entrepreneur and storyteller: Preston Ramirez

Preston started his first startup shortly after he graduated from college in 2015. He has a degree in Computer Engineering, during his time in college he’d built an iOS app and done other smaller projects, but nothing to the magnitude of a business with a full-fledged product. This was his real first experience in the startup space. Since then he has built a few smaller businesses and did consulting work. Currently, he is starting a SaaS business. He finds it interesting that as you go through this journey of previous experiences, you pick up all these lessons and learnings that you can translate to your next journey — and that’s what he is currently doing.

Steve Jobs said it best in the Stanford speech: you can’t connect the dots looking forward, you can only catch them looking backward.

And Preston is going through this process of re-evaluating where startups failed or where they went wrong.

Name of the project: Revive
About: It was essentially a simplified course management software for higher education. It had a combination of productivity tools for professors and students with a social media aspect.
Year started: 2015
Year closed: 2017
Location: Seattle, WA
Industry: EdTech
Category: Learning Management System
Stage: Pre-Seed
How much capital raised: N/A
Key competitors at the time: Canvas, Blackboard

Traction reached: We had built the product and a solid network, we had about 450 users from Gonzaga University, Eastern Washington and the University of Washington in Seattle. At that point, we were still in a limited beta.

Target market, market situation at the time of start: Higher education, professors and students. Looking back, that was one of the biggest mistakes is that there really wasn’t a trend or a need in the market. There were obviously Blackboard and Canvas and other learning management systems, some really bad pieces of software, so there was an opportunity there, but I would say there was really any rising trends. I think there were some people that wanted a better product or a better experience, but I guess the majority necessarily didn’t.

What inspired the idea: My co-founder and I, at the time, discussed various startup ideas and potential companies we could start. I think it was really having just finished college and we had to spend the last four years using these learning management systems that were just very antiquated, outdated, with terrible user experience. So I think we were really grasping for straws as to potential businesses or startups that we wanted. I think we just had a desire to start a company. I think this led us in this direction where it was a combination of a desire to build a startup and seeing the opportunity having just finished college, using terrible software, being able to improve on it. The goal of this product was to increase transparency between professors and students to foster a better bond between the two and create a better user experience.

Success parts, what worked: I would say just that general process of getting feedback worked really well — and that’s so important. YCombinator always preaches that you need to talk to users when building a product. I think that the general process of really talking to your users and just gaining insight, learning how to interview them, ask the right questions, how to pry information, because they won’t necessarily tell you what they want. You have to be kind of an investigator and read between the lines as to what really are their problems, challenges, what do they really want. I would say that just that process of constantly being in touch with your users, communicating with them, going back and tweaking the product, and then putting it back in their hands.

F*ckups/Challenges:

  • One of the biggest mistakes is that there really wasn’t a trend or a need in the market. There was an opportunity to improve the existing user experience. We didn’t make sure there’s a need for our product and this is referencing how the startup came to be. We had a desire to start a company and to do a startup and go through that process. And then we found an opportunity or thought we had an idea. And I think that’s where a lot of entrepreneurs make a mistake — they’re looking for ideas or think of ideas but it’s important to change your mindset to be looking really at problems. We would have had a better chance of success if we were more problem-oriented and looking to deliver solutions to the market that tie into what is the need. I wish we would’ve gone out and talked to users a lot sooner than we did. We were trying to come up with solutions in our head, the problems we thought existed, but there wasn’t really a problem that we were trying to solve.
  • Barriers that we ran into — the level of red tape and bureaucracy in higher education. We knew that there was going to be red tape and it was going to be a slower-moving industry, but not to the level that we experienced. The sales cycle takes years, universities get into multi-year contracts with these learning management systems. So there isn’t much of an appetite for these universities to entertain a new product, especially if it’s not within that sales cycle or the sales cycle that they’re currently in is coming to an end. And then the amount of the layers in the university that you have to go through, that was a challenge that we didn’t foresee coming. We would go to professors to use a product, they’d be eager to use this product and they really liked it and want to sign up, but they said they had to get approval from the department chair and then the department chair has to get approval from IT, and then they have to get approval from the university administration. The layers, the number of meetings, and the time you spend pitching over and over again is a challenging process that we had to navigate.
  • Another mistake — we just took too long to launch. This was the first product I was putting out there, you’re always hesitant because you want to make it perfect. There wasn’t a laser focus on getting a product no matter how shitty out to the market. I think that’s just the biggest thing. In a YCombinator interview I saw maybe about a year ago they say if you can’t build your MVP in under 30 days and launch it, it’s not an MVP. And that’s so true. No matter how shitty it is, you just need to build something and get it out there.
  • The first time doing a startup you’re going to make a lot of the rookie mistakes. If this is your first time doing, you’re probably going to fall into those same pitfalls and traps. I think a big part of that was just getting distracted by a lot of the noise out there, lack of focus. We were focused on the pitch decks and trying to raise money and working with lawyers. And we spent all this time and thousands of dollars on lawyers to incorporate and get all this paperwork done for no reason when we hadn’t finished building the product yet.

Key causes of failure:

  • Looking for products to build, not problems to solve
  • Not understanding the real market need, not talking to target users early
  • Industry barriers, bureaucracy, and red tape
  • Long and complicated decision-making process and sales cycle
  • Took too long to launch, perfection paralysis
  • First-time founder mistakes, lack of focus

Grateful for/Key Learnings:

  • The number one lesson I’ve learned from that experience is you want to make sure there’s a need for your product or your solution to a problem. Look for problems to solve and craft solutions around that, making sure there was a need is the biggest thing.
  • A good way to validate the need in a market is to see if there are potential competitors in that space. It’s actually good to see competitors, but there’s a fine line between seeing some competition, but then you don’t want to see too many. Peter Thiel talks about it in his book “Zero to One” — that last mover’s advantage, I think is what he called it. Facebook wasn’t the first social network, Google wasn’t the first search engine. Apple purposely would look for markets where there was competition, there was a market, there was a proven need, and that they knew they could go in and win that market and dominate.
  • If you can’t build your MVP in under 30 days and launch it, it’s not an MVP. No matter how shitty it is, you just need to build something and get it out there.
  • I’m grateful having actually built a product and launched it, getting users who enjoyed it and liked it. It might seem like a small milestone but a lot of early-stage startups don’t always get a product to market or if they do, it’s not well received.
  • When your startup fails, it feels devastating in many ways. And I think it’s good to just take a step back and reflect, just let it process like a healing process. You commit a large portion of time and life to do something and when it fails, it can be devastating, but looking back I’m grateful in general for the people that I met, the people that I was able to work with, all the advisors that I had and entrepreneurs that I got to know. And then in general, going through that process of building a startup for the first time, because while those mistakes were painful, having gone through all of that I learned so much and I applied all those battle scars to new business. I’ll hopefully be avoiding a lot of those rookie mistakes that I made next time around.

You can watch the full interview here.

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This information’s purpose is to help learn from the mistakes (and pivots) of others, as well as to encourage founders to openly speak about things that failed. Look at it as a shared f*ckup depository for resilient brilliant minds.

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Catherine Yushina
Startup Mortician

Venture Partner and Entrepreneur, passionate about the “why” behind startup failures