What makes a CTO?

One of the deepest questions that I have as I grow into my role as a CTO of MapApp is, what makes one a CTO? How does one even grow into it?

I’ll confess that I just happened to be very fortunate and stumble across an opportunity of a lifetime by scanning a Magic Flyer stuck to the billboard in front of the Glass Pavilion at Hopkins. An opportunity that led me to building software that got me into the Top 10 in HopHacks, into the Spark Accelerator program at the PAVA Center, and onto the passenger seat of multiple MapApp roadtrips across the West Coast with American real estate businessmen.

It was in the first MapApp roadtrip, after developing the software and building an MVP, that me and Ben arrived at the Sakow household in San Diego. It was a beautiful house of a IT specialist who built a few businesses and had his own story comprising of betrayals, failures, character development and eventual success. This was where I discovered the fork between a developer and a leader.

This was also where Dan decided to sit down and tear apart the application from start to finish, evaluating the usability of the application, the possible edge cases that the application wouldn’t be able to handle, the missing features and overall, whether the application even made sense to make or whether we were building an application that didn’t need to be built at all.

It was there that I had to sit down and ponder about whether I spent the last few months building a product that was tackling a solved problem. Whether anyone would even pay me or subscribe to this application that did what other applications also do but differently. Whether I was investing my time into something that would burn to the ground before it could even take off. It was a cold shower. I remember plummeting into despair with each probe that Dan did, stating the issues and tearing into the product. I took a note of every single issue that he spoke of, because even when you’re despairing, you always want to know why and how you could make it better and bring yourself back up. Plus, I take notes when I need to create a checklist or tell a story. It gives me a way to solve the problem once I’m past the phase of processing the situation.

Point is, that’s what a good developer taking feedback and iterating on the product does. But, I’m not sure if that’s what a CTO does. Regardless, that day had me questioning whether this opportunity that I’m spending all my time on was worth it. I was learning a lot about the country, how to behave, how to sell, how to talk and influence people from Ben. And it was an amazing learning journey and I’ve been very fortunate. Yet, a question loomed ominously at the back of my mind, is this really what I want to do? and is this going to make money?

I remember texting Jorge, a guy who was part of the mapapp adventure but then exited, about the talk with Dan and how the application is nowhere close to ready and how there’s already existing tools out there that do what we do and how the application isn’t very focused onto one domain. The objective of my questions and my rants with people are threefold most of the time:

It lets me process my thoughts about the topic.
I get to see how people react to my questions.
It’s in having varied perspectives on the topic that I can use to make my judgement.

However, most people have walls set up to be polite and so that people don’t judge them or perceive them in a different light. There’s very few people who say exactly what they what to say and you need to build up trust for that too.

It’s like Ben always says, “Everybody Lies”. To counter that, I use “Reciprocity” from “Influence” by Robert Ciladini. Tell someone a real story of how you were betrayed by something or someone, and there’s a good chance that they reciprocate with their own story and their own experience, since it’s “giving” back. Most people are wired that way. I decided to be openly vulnerable and stated my thoughts about the state of the app and the feedback that Dan gave us, he agreed with me and stated that, “the way the app is going, there’s no direction and there’s no clear vision to implement a real product”.

What he said was true, to an extent, when you think of it from the perspective of a developer. Now, no shade to Jorge, but he’s never built a business before. I haven’t either. Dan has, but it’s a EBITDA multiplier business that relied on him or people being there to service the product. It’s not a Cash business and it isn’t software. The more business people I hang around, the more I come to realise that there’s very few businesses that are real software businesses that work. That also means that there’s a reason that most software businesses don’t work. My current thesis is that it’s because most founders aren’t solving a real pain in a way that makes them money.

…

The next day, we went to Steve Prescott’s house in San Diego, we showed him the product and he had no complaints with the process and he just asked us questions on how we could import certain data or where we could get that particular data so he could close deals using the application. He actually didn’t care so much about the application either and just wanted to make money by closing a real estate property development business plan near Lake Tahoe for wealthy people in the San Diego area.

It kind of resembled the Rich Dad Poor Dad story where the outlook of two people towards how they make and spend money is very different.

Dan saw problems with the application and how it couldn’t possibly scale if it was as faulty as it is right now. He also mentioned how existing applications could just be used to do what we’re doing right now. He drilled down into the application over the course of 4 hours.
Steve saw the application as a way to just make conversation with his friend. His thought process was always about how he could reach out to people who he could talk to and get a business deal figured out and roll with it. He showed us his existing tooling (PropertyRadar) and gave us information on his existing flow. Overall, Steve talked about our app for maybe a grand total of 5 minutes.

Overall, the application wasn’t really that impressive to either of them. However, they both were pretty happy to talk to Ben after a long time. Steve also gave us a water heater(?) to transport to Lake Tahoe from San Diego the next morning and assured us that we had an attic to stay the night in. (I don’t quite understand this turn of events myself, trust me)

Before our excursion to Tahoe, I got into the shower and spent a while thinking about what I was doing with my life as the hot water continually hit my face. I remember the train of thought process that I had, it went like so-

“What am I doing this for? I’m in San Diego with some dude who I thought was fun to hang around and had fun stories. I’ve spent a lot of time building this application. Did I even stop to question whether this was worth the investment of my time? I could be doing research or applying to jobs or building my own product or business. My life goals when people asked me in the past was always, “yeahh, I think I’ll work in corporate for a bit but eventually I’ll start my own company and build my own business once I know enough about technology”. Well, I did end up working enough and I know how to build products. If I had to build a business, what more would I need?

Firstly, I’d need a problem to solve and I’d need people that have the pain of those problems, enough pain to want to pay money for it…

Wait, isn’t that what I’m doing right now? I have someone who genuinely is in pain and has a problem that he’s willing to spend months of his own time and money on to find people who can build a solution because he knows that there’s a lot of other people like him that have the same pain and would pay money to have someone solve this problem for them. And when it comes to the technical vision, why should he figure out the technical vision and what gets implemented first, he’s not a tech guy. Isn’t that supposed to be my job? Isn’t that what someone taking up ownership is supposed to do? Isn’t that what I’ve wanted so far? Why am I complaining about not having direction? Isn’t this where I’ve always wanted to be? With limited direction and full autonomy?”

It was the epiphany of someone who takes up a leadership position of his own accord. It’s the “fuck it, I’ll do it myself” mentality. It was me taking up ownership and once I talked to Ben about it, he was extremely happy. Because till now, he was trying to juggle different brains and handle logistics for the trip and what had to be built and needed to be done and how to pitch the application. The conversation went something like this- “Ben. You know how one of the biggest problems of mapapp is where there’s no direction and no exact instruction on what to build next or which feature to target next and there’s also no deadline on when certain things need to get done? I don’t think that’s your problem to solve at all. That’s supposed to be my job. If I’m the CTO like I said I would be, then it’s my job to be able to talk to you and figure out what needs to be implemented first and which market we need to target first from the tech point of view.”

He was relieved. And rightfully so, since it’s very hard to estimate how long certain things are going to take when it’s not your domain and you have no way to calibrate the duration. But that’s when I took up the leadership position and allowed Ben to free up a lot of mental space and focus on business opportunities while I figure out the tech to make it happen.

That was six months ago.

I’m in a different place now. The application is nearly built and there’s still bugs but there’s always bugs! It never ends. But, these are reasonable critters and the application is functional now and lets you get a lot of stuff done without breaking the way it did at Dan’s place. But now, I have different questions as the software matures-