Giorgio Delgado

2016 Review

January 7, 2017

As a new year commences I want to look back and reflect on the events that ensued over the last 12 (+1) months.

There were some amazing high's and nearly intolerable low's. Either way, there were great lessons learned that I'll make sure to apply as I continue to grow and learn.

2016 was the progression of a story that began way back in December 2015 when I got accepted into The Next 36. So this is where we'll start.

Acceptance into N36

At the time, I was working on a Peer-to-Peer bicycle renting network whose goal was to replace municipal bike sharing networks all around the world. I had made some progress throughout the company's 11 month existence, including partnering with a UW startup financed by Hax and Velocity to develop hardware for use with my company's bicycles.

Here are the slides that I presented at a case competition in 2015.

Despite being accepted into The Next 36, the organization was not too fond of my business, which made me consider other, bigger, opportunities. Around that same time the partner startup went out of business, and then my cofounders decided to pursue other interests. I subsequently lost the conviction to see my business through. Thus, one full year's worth of work was thrown out the window and I was set to begin anew in January 2016.

While thinking about which venture idea I would work on, and who to work with, I consistently met up with two friends of mine, both of which are equally as ambitious as I am. I consulted them for feedback about ideas many times, and also received great suggestions on potential industries to look into. Not long after talking to almost all the other Next 36ers I came to the realization that my cofounding team was right in front of me all along.

Thus Matthew, Sandro, and I decided to work on something. Whatever that thing would eventually be, we still had to figure it out. But we knew we'd do work together.


Cheesed, Inc. - Photo cred to Matty

Early on during our conversations we came up with something that I actually think had some merit. In a half-serious, half-joking tone, we discussed creating a social network that revolved around complaining. We named this hypothetical venture "Cheesed". In this social network you would complain about shops / restaurants / venues in which you had a negative experience. These negative reviews can then be viewed by the owner of that location in the hopes of reducing "cheeses". As I type this, I'm thinking, "but Yelp is a thing ..."

For obvious reasons, we continued thinking about other, less comical, ideas.

Through conversations about our own problems, we came to realize that the collaborative design process is one that can be improved upon drastically. Collaboration in general is a tough nut to crack. Among its many ingredients, good collaboration requires effective communication, which is difficult within large organizations. As an example, anyone who has participated in a long email chain with many colleagues and stakeholders knows how confusing the dialog can get.

Since Matty is a designer, we decided to have his knowledge guide us as we worked to build a tool to help designers at mid to large organizations do better work, faster. And thus was born dBrief, whose fundamental goal was to decrease frictions / static in communication.

Here are the slides that we presented on Feb 19 (sorry for the lack of context!) to Next 36.

It wasn't long before we realized we were building a glorified version of Google Drive mixed with Asana so we went back to the drawing board to think about ways to help decrease errors in communication.

At this point, four months had passed and it was time to move into the University of Toronto residence as part of the Next 36 program.

Let the Summer Begin

Developing a New Product

May 7th marked our first day at the U of T residence, and the beginning of classes with my fellow N36ers. During this same week, I met with my mentor who began to rant about the problems that occur around Slack's messaging platform as a company grows. This was a problem that related a lot with dBrief. In particular, messaging platforms such as Slack get inundated with useless verbiage such as emoji conversations and gif responses. There are too many channels to follow and too many messages to pay full attention to. Ultimately, people unsubscribe from a lot of channels and begin muting platform notifications altogether.

UofT Grad House

U of T Grad House

There's actually a very popular post about Slack's problems, which served as evidence that this might be a problem many people are facing.

AI was and still is a hot topic, which made us think about ways we could improve Slack's overall experience with the help of this technology. Additionally, my cofounders and I were aware that there was significant money in making Slack better since the company has its own venture capital division.

The field of Natural Language Processing (a subset of AI) is quite fascinating. Using the tools of NLP, computers are able to gain an understanding about human language including one's intentions, sentiment, and more. We thought either conversation summarization or sentiment analysis would be useful for Slack users and all companies in general.

Here's the link to a very quick deck we put together for N36. And here is a much more refined version we put together a few weeks later.

I spent countless hours reading about the capabilities and limitations of Natural Language Processing. I was, and still am, adamant that at some point in the future machines will understand language as well, if not better, than humans.

Learning From the Best

Like previously mentioned, May marked the beginning of classes. We had teachers come from all over to lecture us on many aspects of technology, management, and innovation. The classes were a mix of leading edge theory as well as practical advice from some of the most recognized names in entrepreneurship.

Ajay Agrawal

Prof. Agrawal

Every single class was amazing. Reza Satchu's were easily the most intense classes I've ever been a part of. It felt like a boxing match at times with the intensity that came with his questions and his subsequent inquiries into the logic behind your own responses. Answering with a shallow and thoughtless remark would cost you dearly, for Reza was not one to hold back on ruthless [constructive] criticism. And by not participating in the discourse was only a disservice to your own learning potential.

I got the opportunity to learn about Bitcoin and the underlying technology, Blockchain, from Christian Catalini, who is one of the leading researchers in the field. I was left in awe of Blockchain's potential to transform most any industry that currently depends on intermediaries (banks, online marketplaces, and more).

Ajay Agrawal taught us about useful economic models to consider when comparing entrepreneurial opportunities. Things such as increasing returns to scale, a characteristic that many multi-billion dollar companies posses (in particular; software companies) - as opposed to the traditional "decreasing returns to scale" displayed in most industries. I actually studied economics in university but the economic models that I was familiar with had never been used to assess high-tech industries and the characteristics of innovation. This was a very refreshing take on all the things I had learned in my last few years.

We also watched an awesome documentary called that gave a very raw take on the realities on founding a company in the cutthroat world of technology and "hockey-stick growth".

tldw: Startups are fucking stressful. Even when you're an ex big-time banker.

Although he didn't teach any classes, Managing Director Peter Carrescia gave amazing business counsel. One of the ideas I'll never forget from him is the notion of "Why Now?" Ideas are a dime a dozen - everyone has them. But there are times in history when it makes sense to actually go through with an idea. It's up to the entrepreneur to prove that right now is the time to introduce _____ to the market. In other words; what has changed in the world recently that makes this idea, which many people probably have had over the years, all of a sudden a suitable candidate for my investment portfolio.

This "Why Now?" question is a common litmus test for many investors.

Take Uber for example: Uber was by a long shot not the first company to come up with the idea of crowdsourcing transportation. In the dot-com bubble there were companies who relied on a text-message-only interface to hail a cab. It's quite evident text-based cab hailing didn't win the popular vote. But something happened a few years later that made it more economical to try crowdsourced transportation again. Many companies including Uber capitalized on a very important market shift - that of the mainstream introduction of the smartphone. It just so happened that of the many companies that capitalized on this market shift, Uber turned out to execute best and reach the top - not that it will stay there indefinitely. In fact, there are many people (another link), including myself, who actually think Uber isn't a sustainable business. At least not until their entire fleet consists of autonomous vehicles.

Memorable Connections & Friendships

There may or may not have been a few comical outings interlaced in all of the intensity. I was surrounded day and night by some of the most brilliant people I have ever met, and I am so happy to have been part of this experience.

A lot of the value actually came out of the discussions that occurred outside of class. There were many deep and lengthy discussions about the current state of the world, how to fix it, and what our role is as privileged citizens in a first-world country.

I wish I could replay those conversations again as though they were podcasts.

Reassessing opportunities

As the Next 36 program was approaching its end, I made the difficult decision to take a break from my company and help out (and learn from) a more experienced founder.

Reflecting on a long 9 Months

To be quite honest, 2016 felt a lot like this video:

Epic beginning accompanied by youthful egotism, and eventual realization of my own shortcomings and naiveté.

Oscillating Sense of Self Worth

In the volatile world of startups (or any high-intensity field), one needs to have a rock solid belief in one's self. My belief in myself definitely fluctuates a little too much. And I think a lot of people have this problem. We are all capable of great things but are so concerned about what others are doing or saying that we often forget that our limitations are mainly self-imposed.

I'm now realizing how much my sense of self-worth depends on extrinsic factors. This has to change. A person's sense of self-worth should be exclusively intrinsic.

In other words, I need to stop caring about what others think.

Patience, Composure Key Ingredients to Stress Management

Having hung out with a bunch of really successful or promising entrepreneurs, one characteristic stood out time and time again. Composure.

Composure: the state or feeling of being calm and in control of oneself

Being the anxiety-ridden and impatient guy that I am, I definitely do not possess much of that characteristic. But it was a trait that revealed itself over and over this summer. A lot of these people demonstrated an almost zen-like calmness that I am most impressed by. I can only hope to one day be as zen-like as my fellow peers.

The sensationalization of startups, what with HBO popularizing the industry with its Silicon Valley show and the barriers to entry being practically non-existent, there are a lot, and I mean a lot, of people who want to give startups a go. Everyone wants to be the founder of the next big Unicorn, which creates a lot of pressure to succeed. Every day without progress toward your goal is seen as a day wasted. And without the patience to weather through the bad days you will loose your cool.

The media doesn't help either. They incessantly remind us of how lucrative it is to succeed in this ecosystem. But rarely are we reminded that the chances of succeeding, let alone becoming a Unicorn, are quite slim.

Impulse and Intuition are Not the Same Thing

Impulse should be avoided at all times. It is a subconscious reaction to a situation that, if not careful, can lead to regretting your actions. There is little to no consideration or thought that goes into impulsive behaviour. They're knee-jerk reactions from your most primitive self.

In business, an impulsive person might make a rash decision that in hindsight was probably not the best choice.

Intuition on the other hand is a conscious, albeit illusive, feeling. It's that gut feeling that leads you to unique insights.

In business, a person with an intuition might make a decision that opposes the view of the many and has a good basis for doing so.

Don't fool yourself into thinking your impulses are intuitions. I know I sure did a few times.

Know the Requisite Ingredients to a Winning Team

Are you starting a self-moulding shoe startup? Well you better have a guy who knows about moulding technology (whatever that means). You better have someone who can get investor meetings and knows how to pitch well. Know what the right combination of cofounders you need for the venture at hand. The combination of cofounders is always different based on the industry and context. Hell, maybe you don't even need a cofounder (but you probably do).

Also, an equal split amongst all founders is probably not a good idea. Founders possess different skills, attributes, and assets (including cold hard cash) that they bring to the table. So assess all contributions that a founder provides and split accordingly.

Most importantly, know your own strengths and weaknesses. Weaknesses aren't a problem. After all, we are human. That's why you have cofounders with complimenting skill-sets. But assessing your strengths incorrectly is a problem. Be honest with yourself and don't over promise. Instead, try to over deliver.


When you pitch an idea a lot of people will tell you why it won't work. You'll even have industry experts tell you how naive you are for even trying. Despite all of this, a good entrepreneur would still push on through and figure out if those people are actually right. Hint: They're probably wrong.

But when you get told "no" hundreds of times from investors, partners, customers or whoever, then you'll really start to feel serious emotional discomfort and a strong desire to call it quits unless you have conviction.

Good entrepreneurs must absolutely have the courage of their own convictions.

Follow Your Gut, Not Steve Blank / Paul Graham / Brad Feld / TED Speaker

Yes. All of these people have great advice. But they're probably not as knowledgeable about the problem as you are.

Also, blind adherence to any methodology for business creation is a sure-fire way to crash and burn or not realize a venture's full potential. The lean startup methodology is the obvious example here. It has really useful advice. But that's all it is - advice. Don't treat is as dogma.

Creating A Habit Does Not Mean It Will Persist

As someone obsessed with getting things done and learning as much as possible, I've dug a bit into the literature on productivity and habit formation. I picked up a trick or two about productivity and even managed to change certain behaviours and cultivate new habits along the way.

But one thing I didn't foresee was that I might need to continue cultivating my new habits and shield myself from past habits returning. Alas I should have drawn parallels from gardening wherein simply sowing the seeds to a healthy harvest is not enough. One must tend to their garden obsessively and routinely.

And so I should have tended to my new habits much like a good gardener.

I should have re-read the books I found most impactful. I should have reinforced my habits more ruthlessly. I should have been more meticulous.

I'm in it For the Long Haul

It's a privilege to have been part of The Next 36 and as such I fell it is my duty to contribute to the development of Canada's economy. There's not much else to say here other than I am indebted to the organization for such an amazing opportunity.

A New Chapter at Homigo

Like I mentioned, I decided near the end of the Next 36 program (around August) to help out a N36 Alumni with his venture. I had referred my cofounder Matty to him already, who jumped onto the idea almost immediately.

The two main selling points that drove me to give Homigo a shot were:

Homigo had both of these.

So off I went to learn about the Home Services Industry.

Throughout the last 4 months I have learned a lot; both from the aspect of software development as well as entrepreneurship. I've got to say that things so far have worked out quite well.

I also got the opportunity to go to Mountain View where one of our investors is headquartered.


View from 500 Startups office

And we recently just moved to a new office!

On February we are pitching in front of a live audience of investors to begin creating buzz about our company and hopefully launch it straight into the stratosphere.

To Infinity and Beyond

And this is where I am now; working at Homigo and with big ambitions for my life.

Based on my experience in 2016, I created a set of values and goals that I want to abide by and achieve, respectively, in 2017.

I'll include these in my next blog post. Till then :)

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