My first year as an entrepreneur: a retrospective


Whew! Just like that, one year has flown by.

Last April, I quit a perfectly good job and entered the world of entrepreneurship. A few months in, I wrote an update on my first 15 weeks. And then I went silent.. at least with public updates on this blog.

It has been just over a year now, so here is one HUGE update on how things have gone. Really. This is a long post. You have been warned.

My blogging dilemma

First, I’d like to tell you why I have been away.

There is nothing like that first few months after you quit your job. Everything is fun and new! I started this blog to capture my whole journey. And at first, it was great. I could write about quitting my job, and about how exciting things were.

Then, reality set in.

I was in way over my head… for a number of reasons:

  • Technical proficiency: I quit my job without ever creating a real web product. I had a personal website but that doesn’t count. Web programming is a mix of all kinds of libraries, frameworks, languages, etc. And I had to pick it all up quickly.
  • Startup knowledge: I used to subscribe to Harvard Business Review and read business books for fun. The articles on leadership, management, and running a company fascinated me. I always imagined that the reading would help me if I ever wanted to do my own thing. Unfortunately, it didn’t. Before there is a business, there is nothing. Startups are about getting from nothing to something, and that experience isn’t well described in much of the popular business literature.
  • Web background: I was a researcher in computer architecture. I had no appreciation for products such as Facebook, Twitter, Pinterest, etc. It turns out that if you want to build a web/mobile startup, it is good to understand what these things are, and why they matter. It is a prerequisite.
  • No network: Again, I was a researcher in low-level hardware/software. If you want to contact professors or researchers in architecture, I could probably help out. But my network in the web/startup game? Zero.

I was struggling, and I had no idea what I was doing.

This left me with two choices.

  1. Continue writing about the struggle, and everything I am confused about. Or,
  2. Forget about writing, and just move full speed ahead learning and trying stuff.

A few months into entrepreneurship, I chose the second option. It isn’t necessarily the best choice, but it is what happened.

I have learned that is easy to let my “urgent” work take precedence over blogging. It is also occasionally keeps me from working out. It isn’t a good thing.

Writing often helps me clear my mind and organize my thoughts. It also helps me connect with others on there on the web. So I’m back.. at least for now.

And I’ve been trying to exercise more too, but that is another story.

A summary of the last year.

So what have I been up to? Here is a high level overview:

  • April 20, 2012: Quit my job, and take a week off for vacation.
  • May – early August 2012: Learn web programming. Blog a little. Learn about the web. Wrote my own web todo list app. Scrapped it.
  • August – Nov 2012: Build my first “real” app called Thrive.
  • Mid Nov 2012: Met a few folks from YC Startup School and one of them became a potential cofounder. We re-thought Thrive and began building something codenamed Project Awesome.
  • Dec 2012 – Feb 2013: Hacked on Project Awesome with my cofounder while being affiliated with StartX.
  • March 2013: My cofounder decided to stop working on Project Awesome. I was back to being a single founder. At the end of March, I stopped working on Project Awesome also.
  • April-now: I spent a few weeks trying to figure out what to do. Find a new cofounder? Work on something new? Tough times. I’ll finish up this post with what is going on now.

And now, for the details.

Hope you stick around, because its going to be long.

Meaning and purpose.

One of the biggest reasons I quit my job was that I wanted to (1) create something of my own for the world, and (2) create meaning somewhere in the personal development space.

Meaning and purpose matter to me. I work pretty hard. We all do. When all is said and done, I want my work to add up to something I care about. At my job, I had intellectually interesting work. But it had no meaning to me at a deeper level.

I am big into personal development. In the bookstore, you will find me all over the self-help aisle, as well as the business section. To me, they are the same thing. Self-help is marketed towards people with their lives and relationships. Business is marketed towards people and their careers.

I knew I wanted to pursue something at the intersection of tech and personal development.

Why? Because people matter.

I believe that one of the biggest inefficiencies in the world is people.

If people (1) defined their dreams, (2) kept their dreams in the back of their minds, and (3) earnestly worked towards their dreams, the world would be a better place in many ways.

It is easy to fall short of our potential at each stage. Many people don’t even know what they want. If they do, it can be easy to forget in the day-to-day grind. And even if they start working towards it, it requires time and perseverance to see anything meaningful through.

I wanted to (and would still love to) play a role in making this happen.

I had a plan. Sort of.

Self-help and personal development are pretty low tech. Much of it is stuff for people to consume: blogs, books, workshops, TV shows, etc. There had to be something great to build online for people to interact with. The beauty of web/mobile products is that they integrate with our daily lives. If some kind of self-help tool could be built that people used during their daily lives, it could be so much more powerful than reading books and going to workshops.

I wanted to build this thing.

Vague right? Well, it is a starting point.

My first “real” site: Thrive.

As I riffed on ideas, one of them solidified into something that I felt would be cool. I called it Thrive.

Here is the concept. Most people don’t have a good way of explicitly viewing their lives, both looking forward and backwards.

  • Looking forward, it is important to define what matters to us. We need a set of values and goals, and make sure we stick to them.
  • Looking backwards, it is important to get some sort of explicit feedback about how life is going. Does it match what we want? Are we living lives we are proud of?

Thrive consists of two boards. The first is a forward-looking vision board representing what we want in our lives. You could add your values, goals, bucket list items, and favorite quotes. The second is a reflection board, which contains the things that we have done. The boards are connected via action steps. Each item on the vision board can be broken down into action steps. As you check off the steps, and then check off the items on the vision board, they move over to the reflection board. I believed that over a lifetime, it would be a useful tool for people to keep track of the stuff that matters in life.

And so I built it. The site is down now, but here are a screen shot:

My Thrive vision board

My Thrive vision board

Since this was my first larger website, the development took me a few months. At the end of development, I got a little under 200 people on the site and started using it myself.

The verdict? I didn’t like it. Beyond the first few days, I didn’t use the site myself.


First, I don’t like todo lists. On a particular day, I have one or two most important things, and I do them. I rarely need action steps to do stuff.

Second, the list items were so far in the future that action steps didn’t feel meaningful to me on a daily basis. For example, I have a bucket list item of living in NYC one day. How do I take steps towards it? What is meaningful on a daily basis? I tried adding steps, but they never seemed to make sense to me.

Beyond that, almost none of the visitors did anything. Some of them really liked building up their vision board, but then they just left it, and never came back. Almost no one created action steps. Shoot, I barely created any action steps myself.

At this point, I began to believe that an action-based web app like this would be very difficult to build. I couldn’t make the actions meaningful enough to myself, and I didn’t want to do them on a daily basis. Even if I did, I didn’t feel like checking them off.

This was bad news.

 A cofounder, and Project Awesome.

As things tapered off with Thrive, I met a potential cofounder at Startup School.

He had liked the idea of Thrive, but wanted to simplify it to just a single board. This seemed like a good idea. If you go to Pinterest and search for ‘vision board’, you will see tons of them. Clearly, there was a vertical here to go after!

I had started to believe that an action-based vision board wouldn’t work. But what about making it more social? It I didn’t want to create and check off steps, I might like sharing and socializing about my dreams and goals. We converged on building a new product that was a single board, with social components such as Like buttons and comments.

And thus, Project Awesome was born (the site is up for now, but only gets the single free Heroku instance and may be taken down fairly soon). Project Awesome was always meant to be a code name. It started as our git repo name, but eventually it sort of just stuck.

My cofounder was affiliated with StartX, so we went along with one of the sessions. During the session, we built a site that was basically a subset of Pinterest, and then released it to about 100 people.

What happened?

I liked it slightly better than Thrive. The user base did also. People built up some boards, and some social action took place. It turns out that adding any social component to a site seems to make it much more engaging. I liked occasionally chatting with strangers about what matters in life.

However, after a few weeks, I had a hard time continuing to use it. I tried all kinds of things. I used it for a workout journal. I used it as a gratitude journal. But it became boring to use!

One of the design decisions was to limit the vision board to 20 items. Focus matters in life. We wanted to differentiate from Pinterest by forcing focus. From a theoretical standpoint, it sounds good. Practically, the focus eventually becomes boring.

After a few weeks of using it, my cofounder decided to pursue something else. I couldn’t blame him. The product wasn’t that good, and on top of that, we had some troubles with different working styles.

A few weeks after my cofounder left, I decided to stop working on Project Awesome also.

It isn’t all rainbows and flowers.

You know how everyone says entrepreneurship is a huge emotional roller coaster?

When I quit my job last year, I thought that was BS. You see.. I am one of the most optimistic people I know. I barely ever get down.

But, now I know. It is certainly true. Entrepreneurship is one hell of an emotional rollercoaster. Seriously. This shit is tough. Really really tough.

It had been close to a year and I had nothing real to show for it. I had now built out two products (or two versions of one product depending on how you see it) that I didn’t like. I also had a cofounder that didn’t work out. I had also applied to YC twice, as well as a few other accelerators, and been rejected. The rejections made sense though. I was a single founder that hadn’t figured out much yet.

What followed was pretty much a few weeks of nothingness. I didn’t know what to do. I didn’t know what to build. I was struggling, lost, and totally confused. And because I didn’t share it with anyone for a week or two, I was alone in this nothingness.

From an emotional standpoint, if there is one thing I have learned, it is that when shit gets difficult, share it with someone! A week or two later, I started telling people that I was down. I told them that I felt lost and had no idea what I was doing. The funny thing was that just sharing it made me feel way better.

My great epiphany.

Soon after, I had a great epiphany.

I was building things to try to get people to do stuff.

That is the wrong way to think!

I needed to build things to help people do what they want to do!

I had heard this from people several times: “Alex, you are on a noble, but difficult mission”. And it was true! I wanted to help change people. But from a business perspective, it makes things difficult.

Here is another way to put it.

Lets say we know two things. The first is something people do. The second is something that people don’t naturally do, but you want them to do. Which of these things would you stake a business on? If I were a betting man, it would be obvious: the first thing!

So for the time being, I am hopping on board with the first option. It seems like the smart thing to do. I want to build something that helps people do things they want to do.

What now?

Currently, I am struggling with a question.

Do I make finding a cofounder first priority? Or do I just start with something?

I don’t know the answer, so I am doing both. I can’t guarantee when I will find a cofounder, but I can guarantee real progress if I start on something (unless the idea is bad again!).

A few weeks ago, I came up with something new to build. I like the idea a lot so far.

I want to build an aggregator and community for content related to living a good life. Personal development can be hard, but one thing people do is that they consume content. A lot of it. I want to build something that helps people find, share, and connect over the best content.

There are only two rules:

  1. Anything related to living a good life in on topic.
  2. No assholes.

There is good life related content fragmented all over the web, across blogs, web sites, videos, etc. I look for it, but it can be hard to find the good stuff. And often, the good stuff is fragmented. A particular blog may have one or two good posts, but to drive page views, they need a ton of other watered-down posts.

This is something that I want to use. And, I think others would like it too.

I’m about 2-3 weeks into building it and it is almost ready. So far, it is something like a love child between reddit/Hacker News, imgfave, and svbtle.  I’ll share it in the near future 🙂

Lessons learned

On one hand, I have almost nothing real to show from this last year.

On the other hand, I have grown and learned so much about myself and about entrepreneurship that it is crazy.

Here are a few of the things I have learned:

  • Help people do what they want to do. My big epiphany. You can either try to change people, or help them do what they want. You’ll always be better off helping them do what they want to do.
  • Entrepreneurship is great job. Yes, it is tough as shit. And yes, it can be a huge roller coaster. But I wouldn’t trade it for any other job in the world. It is difficult because things really matter. Entrepreneurs try to create real value for the world. Creating real, scalable value isn’t a cakewalk. But it is worth working for.
  • Cofounders can be awesome, except for when they aren’t. I have worked with and without a cofounder now. It was great having a cofounder, but when there are problems, things can slow way down. There is value to having a team, but make sure it is a good team that works together and is aligned with similar goals and visions.
  • Keep good company. I have 3-4 other friends who are single founders. We meet once every few weeks and trade thoughts and stories. They have kept me sane and given me a sounding board whenever I have needed it.
  • Share your experiences and feelings! As I said before, there are definitely down times. We like to project success and happiness, but if you are having a tough time, make sure you have people to be honest with.
  • At some point, be honest with yourself. This is with regards to your startup idea. Try your own product. If you don’t like it, that’s not good news. If others don’t like it, it needs work. Either learn from them and change the product, or do something else. Most ideas suck. Yours probably does too. That is OK, as long as you recognize it.
  • Tighten the loop if possible. I worked on both Thrive and Project Awesome for a few months. Waiting a few months for user feedback is not good. I’m trying to figure out how I can tighten this loop, and make better use of my time.
  • Getting users is hard. Either you don’t know how to reach them, or your product sucks. Or both. As a tech guy, it is easy to just keep building. My toughest battles are to stop building stuff, and to actually make sure I’m building something worth building.
  • Entrepreneurs are awesome. The entrepreneur culture is amazing. I think it is because we all know how hard this job is. We are all in the deep end just trying to stay afloat, helping each other is the right thing to do. I’ve met some amazing people so far, and everyone has been very supportive and helpful.
  • Keep going. Think long term. You will have lots of setbacks. But, over time you learn a lot. Things get better. And faster. For example, Thrive took about 3 months of coding. Project Awesome took about 1.5 months. This new thing is 2-3 weeks old, and pretty much done. But beyond that, each product is just one thing. The real product is YOU. Every hour of work makes you better, so just keep going.

Now, last but not least, here is the most important lesson:

No matter what, you will make your own mistakes.

Check this out. None of this advise is new. Look at most startup blogs, and they say the same thing. But you will make many mistakes, and learn the same things anyways.

Here is an awesome example.

My biggest epiphany so far is that I need to create something to help people do what they want to do.

What does this sound like?

YC’s number one rule is: make something that people want.

This is probably the first bit of startup advice I read after I quit my job. And somehow I found myself re-learning it almost a year later!

You can read stuff and it makes sense in theory. But doing things right in practice?

Good luck.

During my big epiphany, Alvy Brooks was selling these posters for donations to Watsi. I snapped one up and it is now by my desk as a reminder every single day.

During my big epiphany, Alvy Brooks was selling these posters for donations to Watsi. I snapped one up and it is now by my desk as a reminder every single day.

10 thoughts on “My first year as an entrepreneur: a retrospective

  1. U look happy and optimistic in your FB profile picture (sometimes it says alot about the characteristic of the writer). And somehow, intuitively, I kept track on Project Awesome to find sth new to make me feel better. Yes, here is the answer: try to come up with an idea which will make people feel better. I always envy on being a DJ in a club. Can u imagine how u are going to feel great when u make people happy and see them going crazy on the dance floor?

    Utku PASHA 😉

    • Hey Utku! Thanks for dropping by. I’ve actually been envious of good DJs also. They get to work on their craft while getting the party started so that everyone has a good time. I hope to get that feeling by creating something merging technology with humanity/society.

      Glad to hear from you and hope things are going well at NU!

  2. stick with it! nobody succeeds on the first try. only the determined will eventually succeed. keep trying… and learning.

  3. Thanks for the update man. If I could afford it I would love to jump into the fray with you and chase down a product that would stick.

    But in the absence of being able to do that, I will live vicariously through you! 🙂

    Keep up the good fight – I believe in you, and think these insights will help immensely as you keep on this path. And, don’t be afraid to call and ask me for anything – I might say no if I’m too busy, but more likely than not I’ll have time for you if the kid isn’t screaming at that moment. Seriously, call even just to get someone in the midwest to listen to you (even if you are in a whiny mood) and bounce ideas off of. Really, I just love chatting with you, and don’t think I’m going to be in your area for a while, so call whenever.

    • Ben! Great to hear from you dude. I’ll give you a call sometime for chat.. its been a long time since we’ve caught up.

      And, as I wrote about, I have something new in the works. Will send an invite your way in a week or two!

  4. hey man, good read and good lessons. Sounds like you are on the right track with your thinking.

    I guess my small contribution would be to focus on a problem:
    – that you want solved
    – other people want to use

    use the customer discovery process in the startup owners manual. it will force you to be honest with yourself and recognize when things aren’t going well and when they aren’t.

    Also don’t worry about the cofounder thing. Doing the startup thing is a lonely endeavor, and it sounds like you’ve already got a good support group surrounding yourself. At the end of the day I don’t think it is worth trying to mesh people who didn’t come together from shared experiences and values on the problem. There is nothing wrong with hiring employee #1 and giving them a chunk of stock/options. You can definitely listen and learn from them – we learned a lot from our early employees. The downside of having founders who have divergent interests are really painful imo. That being said, if you find someone and things click, go for it 🙂

    • Great to hear from you John!

      Yup, I am learning a lot about the customer discovery process the slow way. I’m trying hard to incorporate it early in the ideation process now, and it has been really useful for thinking about your value prop, customers, etc.

      As far as the cofounder thing goes, it would be great to have one. But you are right. If you don’t mesh from shared experiences, things get difficult. Also, having a prior working relationship would help a lot. I’ve been writing up a blog post just on this topic.

      Would love to chat more some day.. let me know if you come by South Bay in the near future!

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