7 lessons from starting my first startup as a 19-year-old solo-founder
I started Homeroom after dropping out of college. Here is a recap of my journey, mistakes I made, & the lessons I learned.
At 19, I started my first startup as a solo founder called Homeroom right after dropping out of college. Homeroom was on the mission to create connected and data-driven classrooms, with the grand vision of changing the way we approach learning, both in and outside of the classroom. Think of Homeroom as OkCupid and Slack for students and Mixpanel for professors. Through an interface like OkCupid + Slack, students got to engage and feel more connected, while professors utilized the insights (similar to Mixpanel) to understand student behavior and patterns to better tailor the class material to their students.
Watch Homeroom’s demo: https://www.youtube.com/watch?v=rd8R_Ob8GYo
We conducted multiple pilots in classrooms, but last November (2018), due to a personal/family situation, along with the educational sales cycle time, I had to take a step back from Homeroom. As a 21-year-old, I reflect on my ~2-year journey, mistakes I made, lessons I learned, and I thought it was worth sharing to the next 18–19-year-old who dreams of building their startup one day.
As you will notice, these are textbook “What not to do while building a startup 101” mistakes and somehow I managed to do it anyways. 😅
These are my thoughts and opinions from my specific experience. It may or may not apply to everyone.
1) Get a co-founder from the start.
As a young and inexperienced 19-year-old, I underestimated and thought I could manage everything about a startup, from conducting user interviews to designing prototypes to developing the actual product to sales/contract negotiations and everything in between. While this was manageable, it required 12–15 hours a day, as a result, I was mediocre at everything I was doing because I couldn’t spend time working and focusing on one aspect (or just burnt out).
When I was building the product, I needed to talk to users, get customers, but when I was spending time talking and attract users for the pilot, I was not building, which made me feel unproductive.
Another important aspect of this, and probably the biggest factor/variable, was the emotional toll of starting a company alone. Not having someone with you to tell you that you’re doing something wrong, to challenge you, to bounce off ideas with, to truly share how you’re feeling, adds a whole lot of extra weight on your shoulders, which compounds the stress of bootstrapping a startup.
Having a co-founder isn’t only about sharing responsibilities — it’s knowing that someone shares your vision for the future and someone that will keep you accountable for what you build because they’re just as passionate and vested in the product as you are. As I look back at successful companies, mostly all of them had a minimum of two founders dedicated and driven to manifest their vision into reality. A quote by Helen Keller captures the essence of this perfectly:
Alone we can do so little, together we can do so much.
2) Asking the right questions to your customers/users.
There are a couple of sub-lessons within this. The first one is to talk to your customers/users first the right way. Your idea is a hypothesis and you need to validate it before building it. But one thing people don’t tell you is how to ask these questions. For example, I remember having said this in one of the earliest interviews with a professor at Stanford:
Hi, I am Keshav and I’m working on an educational startup for classrooms called Homeroom. I’m building a product to solidify the relationships between students and teachers to create high engagement in class. Would you want to use something like that in your class?
There are a couple of things wrong with it.
- I went directly into what Homeroom is, what I am building, with a question to put them in a spot. I was thinking of user interviews as selling my idea to them instead of trying to learning about the problems and challenges they were facing on an everyday basis. The goal of user interviews isn’t to talk about your idea (at least in the beginning) — it’s to learn about them, their behavior, how they do things today, and to see how you can solve that.
- When I asked professors if they would like to use Homeroom for their classes, I put them in spot and most of these professors did not want to be the devil who shuts down a 19-year-old entrepreneur. So guess what they responded with? “Yes, I’ll use it.” But when it came time to do so, most of them had deferred or didn’t respond.
Instead, I should’ve asked them questions like these:
- What are the not-so-fun parts of your workflow?
- What makes it so awful?
- When was the last time you felt that problem?
- Can you talk me through the way you’ve tried to fix them?
While the first two may seem like obvious great questions, the last two are the ones that validate whether or not the hypothesis you’re trying to validate is real.
If the interviewee brings up this “awful” problem but has done absolutely nothing to fix that, perhaps it isn’t that “awful” in the first place. Maybe they just don’t give a shit as much. In this case, the goal becomes to find that “awful” problem/part of their workflow until it’s validated by something they’ve done to fix it. If so, try to find this trend in your interview. If this problem surfaces in other interviews, you’ve got something.
There’s a great book that was recommended to me by a YC alum called “The Mom Test” — the title probably gives it away.
Talk to as many people as you can initially, but go in with a purpose and get out with a “Yes” or a paycheck (for some). I interviewed 8-10 professors early on, but again with the quality of interviews and the way I asked questions, it didn’t mean anything.
Anywhere between 10–15 interviews is a good number as it provides you with sufficient insights around different behaviors and challenges your audience faces to pattern match, but remember to stop when you feel like you’re not learning anything new from them.
3) Keep your product’s surface area low
This was truly one of the biggest oversight from my end while working on Homeroom. I knew that my goal is to build the “Most Viable Product” (whatever that means), but I subconsciously started to add new features because I was infected by the “this would be really cool to have” virus. As I was collecting feedback from students and professors, they said they liked the platform, but adding “x” and “y” and “z” would truly be helpful to them.
As a young founder, I took their words as prophecy and built out those features. By the end of a couple of iterations, I had 6–7 features within Homeroom that were quite independent of one another, so by then, I was having a hard time explaining what Homeroom really did.
You should aim to narrow down and center your solution around one big problem. When building your product, it’s tempting to add features, especially if your users asked for them, but in some cases, like mine, it did more harm than good because at the end I was left with a product that was “solving” different problems poorly and not one thing extraordinarily.
With Homeroom, that was the aftermath — in building out a lot of features, I built a product with no clear tangible value.
A better way to weed out these suggestions is by asking “why?” to your users. Why do you need this feature? Why would it be a dealbreaker if this functionality didn’t exist?
If it’s something that is just a “nice-to-have” but doesn’t align with your overall product vision or adds high product value or gets people to pay for it, defer or discard it. The first version doesn’t need to have 10 features or even 3— it just needs to do one thing really fucking well and add clear value to your existing users and potential customers.
Also, be skeptical when someone says “add x” to your product. It may seem easy to build a faster horse, but what you needed to build was a newer medium for transportation that would revolutionize the way people commute.
Building a product with focus is draining, but what’s even mentally draining is building a product with a lot of features that no one wants to use.
4) The “Startup life” will consume you
There are many trade-offs to building a startup. Yes, you get to work on and build your ideas to improve the lives of others, which is, in and of itself exciting. But building a startup is very time-consuming. There were months where I didn’t speak to my friends or socialize or go out. Even when I wanted to go out, there was simply so much to get done that I couldn’t afford to (double true since I was a solo founder).
Working on your startup is a commitment to yourself and your dream. You may find yourself working 80–120 hours a week. You will find yourself thinking only about your startup all the time — when you hang out with friends and family, you’ll be thinking about your startup (actually they’ll remind you by asking you how’s it going, are you sure you want to do this?).
Even when you’re in the bathroom, you’ll be reading blogs by Andrew Chen on growth hacking or trying to gain wisdom from PG’s essays! The smallest thing will keep you up at night — especially the times you were rejected when you pitched your idea to your customers, friends, investors.
Startup is literally like having a baby: it’s going to cost you a lot, it’s going to require a lot of attention, nurturing, cost you sleepless nights, and unfortunately, some people find themselves being the single mom/dad. Only this time around, “growth” isn’t guaranteed.
You’re going to feel exhausted, things will not always pan out how you expected them to be, you will be spending the money you saved up, but you’re still going to have to keep going. I realized that my social life took a massive hit when I isolated myself as a solo founder. What did I do?
I leveraged Twitter and LinkedIn and reached out to over 250 people in 4 months. I ended up meeting around 50 people and some of the people I’ve met during this time have become some of my closest friends. They were builders, engineers, designers, product-peeps, former founders, current founders, aspiring founders, investors, angels, and most importantly, people who wanted to do things bigger than themselves.
Being a founder of a company became the reason for me to connect with these people and they gave me advice, insights, and helped me later on in my journey with Homeroom. Even though I didn’t have a “co-founder”, they provided me with the support that I truly needed. Had it not been for running my company, I don’t think I would’ve been able to meet some of the most brilliant people that I did.
5) Be lean and move fast
I’m sure you’re thinking, “Did you not read Lean Startup, Zero to One, and Founder’s Dilemma? They all tell you to move fast, get a co-founder, build one thing, etc..”
Yes, Yes, and Yes.
All of the advice in these books seems obvious and were to me until it came time to employ them. I knew that getting a co-founder would be critical, but I couldn’t find people that were just as passionate as I was about changing the landscape of classrooms in college. As I alluded, being lean is an advantage for young startups since they can make mistakes, but get up fast, and experiment with things, but being a solo founder slowed me down tremendously. To reduce the friction of speed, I did take some shortcuts like not writing integration tests for user login and everything broke the night before pilot launch. When I fixed the bug, it caused regression in other parts of the codebase. I had no shoulder to cry on.
Is this an excuse? No. This is me admitting that I had/have a lot to learn. I felt like I needed to act like a “know it all” founder, who had everything under control, is great at everything, can code and fly an airplane, blindfolded, while juggling 10 machetes with one hand and no sleep.
In the span of 2 years, I spent time on writing business plans, recruiting for co-founders, pitching at competitions/VCs, and planning a Kickstarter campaign to raise money for Homeroom (thank god it was just a plan). While I do believe market research/analysis is a crucial step, mapping these financial projections felt like pulling a number out of my ass just to show people that the business is viable. In various competitions, the focus wasn’t much on the quality or what the product did — it was on how good your business plan is. But I went along with it because I thought it’s just a “startup-y” thing you got to do.
In the hindsight, I wish I had spent more time on analyzing the market thoroughly, talking to more customers, focus on one aspect the product, and aggressively got classes and departments to use Homeroom.
6) 9 of 10 startups fail, so just build 10
Ok, so at this point, it may seem like working on my startup was pushing a boulder up a hill (with two broken legs and half an arm) and the worst experience ever, right? Nope.
While Homeroom wasn’t the success that I had envisioned at the inception, I can certainly promise that it won’t be my last one. People say “9 out of 10 startups will fail” and to that, I say, “Just build 10, so that at least one can succeed”. It’s all about mastering your craft.
If you want to be successful, you have to put in the time and be willing to fail (but learn from it). You have to try things even if you know you may be able to achieve them, for the sake of growing, learning, and perfecting your craft. Bruce Lee once said:
I fear not the man who has practiced 10,000 kicks once, but I fear the man who has practiced one kick 10,000 times.
Building a startup is like that as well. It’s the matter of pattern recognition, understanding what works, what doesn’t, framing the problem properly, and being cognizant of the value you bring to your customers. These skills develop over time and are instrumental in allowing you to become confident about what you’re building. So while I am a bit disappointed that Homeroom didn’t work out the way I wanted to, I’m glad I got to learn some of these mistakes as a 19 and 20-year-old entrepreneur. To me, that’s a better education than sitting in a class.
7) It’s about the process
Reid Hoffman puts it interestingly:
Building a startup is like jumping off a clip and building an airplane on the way down.
While this is pretty extreme, there’s some truth to that. The cliff represents stability and jumping is the leap you take trying to build that “next” thing.
Building a startup is about iterating. Most ideas do not strike on the first attempt, which is why you need to always re-assess the product you’re building, analyze it from different angles, and determine if you need to pivot, whether it’s the product, the targeted demographics, or the market.
In essence, building a startup is a process. In this process, there is a lot of learning, individual growth, failure along the way and a lot of disheartening moments, but when you jumped down from the cliff, you signed up for this.
You signed up to be smashed right into the ground. And you might crash a lot of times and that’s where your grit comes into play. You have to have the perseverance to keep getting up and keep moving, whether or not you’re with others or alone.
There’s a quote from Confucius that has always stuck out to me, which I try to live by:
Our greatest glory is not in never falling, but in rising every time we fall.
So keep falling, keep trying, but remember to keep getting up. Nevertheless, the point I want to get across is that being smashed into the ground is part of the journey and that building a plane while it’s falling isn’t always going to work out. If you do it enough times, you might just strike in your 2nd attempt or your 10th attempt or your 14 millionth attempt (just ask Dr. Strange).
In the end, you can’t enjoy the fruits of your success and your work unless you have suffered a bit through the disappointments, the failures, the rejections, and the existential crisis along your entrepreneurial journey. This is just the beginning for me — here’s to the future! 🥂
What are some of the lessons you have learned either by running a startup or building a product? Leave them in the comments or DM me on Twitter!
This blog was originally posted on https://www.narulakeshav.com/post/7-lessons-from-starting-homeroom
