Modern CTO Podcast

Guest: Doug Woodrow

Today’s episode of the Modern CTO Podcast, Joel talks to Doug Woodrow. He’s early in his CTO career but looks to be one of the most promising CTO’s to look out for. He is the CTO of Knightspeed which is a company that is looking to change the moving game. We discuss the pain of gaining experience, machine learning and billionaires.

Time Stamped Notes

0:48 Blending Roles: CTO to CEO

The gap between CTO and CEO is slowly bridging. This is due to the fact that technology is moving so fast at the moment that you have to have a really detailed understanding of the technology in order to even make the business decisions. If you’re constantly communicating that to the CEO, over time, it becomes much more efficient for the CTO to make those decisions on their own. The developers also seem to know what is going on before the marketing people do. This is because that information hits the API before Facebook marketing team gets it out the door.

Doug talks about the growth of programming and software engineering as a whole and the needs that we are going to require over the next 30 years. It’s going to be harder work to avoid learning technology than it is. The growth of the CTO is now huge and more involved. He uses technical skills to solve non-technical problems. He models real world problems in his head as code and then uses them in real life through networking within human beings. It’s so funny how the business word and the tech world lines up so easily.

4:48 How The Movie “The Social Network,” Changed the Tech Game

One of the movies that really spawned the glamorization of the tech world was the movie “The Social Network.” Even though some of the details were blown out of proportion, it inspired everyone to be a technical person and be the next Zuckerberg. Being in technology calls to this inner person that everybody has within them – this inner pioneer that’s really excited to be able to do anything without any rules and limits. The computer provides that for a lot of technical people.

6:22 Mr Robot

Doug and Joel discuss how Mr Robot uses actual accurate coding in the TV series and how people are hired from Def Con for this show.

8:54 KnightSpeed

Doug is the CTO of KnightSpeed and he discusses how the new site he based on consumer psychology and science. It was all built in Angular 1 before which created a lot of problems for them. Do not use Angular JS for a consumer website. You can’t do SEO’s and preloading is very difficult. He’s intention was to change the image of what a moving company looks like. Removalist companies are getting by without being innovative. However, that is fine for now but KnightSpeed’s mission is to change that. Doug’s team saw the opportunity and went in and executed. Four years ago in college at UCF, Doug met his business partner who had be working as a removalist for cash on the weekends. They realised a lot of people need this and it’s very profitable. He put up a flyer and started to get quite a few calls and needed someone to help out with the technical and logistical aspect. They have grown the business through building a website and through Facebook advertising. They’ve taken the least amount of investment on with two rounds of funding. They have broken even in Florida where their operational costs are covered just by the moves. At this point, they have moved to a profitable model. They own two moving trucks and 40 employees and are breaking even month to month. The first version of their logistics software called “Manage Move,” is out which allows the business to scale across 20-40 cities across the US to become an household name which is impeccable timing given that they are up for another round of funding. The CTO’s role is very important where you have to build a great business model under the hood and you have to make something amazing, grow it between people and once word of mouth is going around that your product is great, you are able to expand your company and eventually build software. Joel talks about a real estate example and capitalising on an opportunity which Doug had a similar experience in.

19:49 Developing Custom Software and Intellectual Property

Having your own custom software gives your business some IP. If there were ever to be a management fiasco, that software is still licensable and salvageable to some extent, worst case scenario. Tomorrow something may happen and the operation may have to be shut down – and as a longer term option, the software alone can be enough to be a sustainable business. The fact that the software developers were able to see what it was like working in that industry and the pain points of working in the area is an advantage. To the Investors, it’s a holy grail. They started as a cash business with little debt and now they are at a point where the infrastructure is there to facilitate the software which can move them out of the operations game. Every move they have made has been what has been best for the customer.

27:30 – The Opportunity To Impact

The ability to impact others has now become so easy with technology. Being able to have the impact that you want so quickly and reach out to other people and connect with other people is so valuable.

29:10 Obtaining Experience

It’s not easy to obtain experience. You work for the experience and you come out with battle scars. Joel talks about double and triple down on the things you are good at. It took Joel a month or two to figure it out and work through his developer mindset. After taking a break, he began working on the book and he began to thing about his career of 17 years as a developer. He began to think about how valuable it would have been to have a roadmap or an instruction kit to help him through this career. Hence the Modern CTO book was born which details the roadmap and lets the CTO know – the path may not be easy, but here’s a toolkit to help.

32:25 The Why Behind What You Do & Artificial Intelligence

For Doug – the Why is the Impact. Technology allows us to have that impact very freely and we can broadcast a message to millions of people for free for the most part – this is outstanding given that 120 years ago, we were getting into the brink of electricity. He believes that AI is the next electricity – or more to the point, machine learning is going to be the new electricity. Doug talks about a case which he has read about a Robot and Artificial Natural Intelligence and what kind of a generation we can look forward to.

38:02 Simon Sinek, Gary Vee and Figuring Out Stuff

Simon Sinek is a great mentor of learning the why behind what you are doing and about teaching balance. What he does is so useful and his approach to things is to look at a situation and tear it apart in a way that you generally don’t think of. He is great at verbalisation and communication the analysis of introspection.

Joel had to spend years to figure out his entrepreneurial journey and discusses how he had to eat “shit” like Gary Vee would say. Doug chimes in on how we need to get to that point in life where you need to figure out what you want in life.

46:30 Documenting The Journey

Gary Vee often talks about Document versus Creating. Joel talks about a friend who’s asked for advice on the next steps and Joel suggested the method of documenting. People love living vicariously now so any amount of content that allows people to do this comes in the fashion of documentary. Humans are curious about what people do day to day, what are their interactions like – this is incredibly powerful content. You are empowering a whole generation of people where they see every day that leads up to a certain goal or presentation.

53:04 Monkey See Monkey Do

Joel talks about how he has Audibled the life stories of certain billionaires. Doug talks about just because you show everybody everything through your content, there’s still only 0.005% of those people who are actually going to take action and do something. The people that get ahead of the market, they don’t care about people copying their stuff. Joel also talks about the process that he goes through when he has a great idea and wants to develop and build it into a business.

59:03 KFC

Joel has a younger cousin who is obsessed with KFC – to the point where he got a guy to dress up as Colonel Sanders for his birthday party. Looking from today and going back – if KFC were to give away their chicken for free. They would be able to:

Engage with their fans

Build a community

Source Influencers that were loyal to KFC

Develop an entire community around KFC and it would cost them nothing

Doug discuses that making an open source has become a powerful and a separate part of the business. He talks about how a few years ago, people thought that Facebook would die one day. They can never die because what do you do to connect with people, to sign in with etc. They have given all these integrations to all these developers to have source code running in someone’s system in a way in which Facebook now can never die.

1:05 Backing Your Best Developers

Take some of your best developers, put the companies’ money behind them and make them better developers – it’s a way to build them up. Some fear based decisions that companies make is that when you invest so much money in talent, there is a fear that they will leave. The other way to look at it is, that person got their entire reputation by being the lead at your company. You will attract great talent and you will be the company that puts the best talent in the market and that person will forever be known as the company that has the best people. If you look at the money you spend to do that isn’t that much, but the return would be mind blowing. The power and the presence of somebody that gives you positive feedback is much more powerful than a negative one. This will continue to sell your product for years.

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