The CTO Podcast

It's no small feat to go from the second developer in a company to its CTO, but one man who is up to the task is Jesus Lizama of Studio 3. Jesus is joining the CTO Studio to talk about his career progression, as well as what it's been like to live here as a DACA recipient.
Jesus is an engineer who has become CTO of Studio 3, a rapidly growing agency. In fact, his agency is growing so fast they are doubling their revenues every year! They are now a two-time Inc. 5000 company.
Today you'll also hear about how he is managing his team through this tremendous growth and what he's learned along the way. Plus he has a very special story to share on the topic of immigration and DACA. Listen in for that and more on this edition of CTO Studio. 
In this episode, you’ll hear: 
How has being CTO changed things for him?
Does he still see himself as a developer?
Where did he had to grow the most after becoming CTO?
Why does his team choose their own tools?
How did switching to Slack and Airtable help his team?
And so much more!
We begin our conversation with a discussion about Studio 3: Studio 3 is a all-encompassing marketing company. They specialize in digital marketing, but also do print, and other media. If you have an idea and you bring it to them they can give you a product.
Prior to joining the agency, he was going to college and was working at the university as a math mentor. He was on break and he wanted to start programming. He went out on Christmas Eve and decided to try to get a job in the field. He sent out a bunch of resumes through Craigslist and that is how he landed at Studio 3!
Right away they threw him into a project and had him build a web site. He started at a time before mobile responsiveness was really big, but he had them build for that and he changed a few other technologies he knew would be helpful. After a year or so he became lead developer and the company kept growing. The company now employees sixty employees, ten of which are engineers.
What about becoming CTO - how did that transpire? It all started during a meeting he had with HR, the person he was meeting with asked him where he saw himself in five years. He replied honestly telling her he saw himself as CTO of this company in 5 years.
It turns out the CEO of the company at the time was thinking the same thing. The CEO took him to lunch a week later and he told Jesus he wanted to make him CTO. A few months later he became CTO.
He says now that he is CTO it hasn't changed much for him, hierarchies are non-existent to him. The main difference is now he is involved in the company's strategy, and that is something he is still learning about.
What about his nomination for 2018 CTO of the year by the Los Angeles Business Journal - has that changed anything for him? It was amazing, he says he felt like he didn't belong! He was among big name CTOs: the CTO of the LA Clippers, Los Angeles' CTO, Playboy's CTO, Verizon's CTO and Disney's CTO, etc. At the dinner for the nominees he sat at a table with LA's CTO and he had a great conversation with the Clippers' CTO. He was nominated again for 2019!
Also on today’s CTO Studio, we dig into his actual experiences as CTO a bit more, I asked him to share the first obstacle he had while CTO.  One of the first tasks he was given was to build a reporting platform. His background is primarily building web sites, which were mainly static or perhaps had a few business logic components involved but not too many. A reporting platform on the other hand is a full-on MVC application!  
In addition to being the CTO, he was also a developer so there were a lot of technologies he had to grasp very quickly so he could build an MVP. After many iterations and a year later, they finally had a working system  that was useful for the company

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If you were considering joining a start-up as their CTO would you have a formula to evaluate its potential? Our guest on today’s CTO Studio does and it stems from his years as a CTO, an advisor and mentor in the field.
Sergey Sundukovskiy is the CTO, CPO, co-founder of Raken. He's also a mentor, advisor and father of three. 
Sergey and I have a great conversation about the formula for evaluating start ups and how to manage and keep healthy development teams. Join us as we dive into those subjects and more on this episode of CTO Studio. 
In this episode, you’ll hear:
What is the benefit of being both CTO and CPO (Chief Product Officer)?
What are the two sources for ideas?
How has their product changed since its inception?
Why compromise doesn't always work to solve disagreements.
Should all CTOs mentor?
And so much more! 
We start with a discussion about Raken: what it is and who it serves. Raken is a field management solution. They serve the construction industry by helping supervisors and job foremen keep track of what is going on on the construction site. So often the people in charge realize there is a problem when the job is running behind schedule and off track, Raken helps avoid that scenario.
Raken helps construction companies to keep the construction projects on time and on target through daily documentation and labor/project insights, as well as serving as a Worker Time Management app for payroll purposes. Sergey explains what it does in more detail: If you have ever been on a job construction site you know jobs are broken down into roughly 3 separate buckets. Prep time is one bucket, the second bucket is the actual build stage of the project and the last bucket is the transition stage when you are completing the project. 
They primarily serve the building stage and the transition stage. In the building phase you need to be sure you are on time and things don't need to be adjusted.
Basically Raken is project management software for the construction industry projects focused on field management tools. Normally, construction projects are driven by the management office in the office/field trailer and then what happens on the job site. The project gets conceived in the office and planned in the office. Raken's approach is to service the field. They serve the field workers so the field workers can keep track of activities, and to do so in a simple and easy-to-use manner.
Raken helps Superintendents to document what is being done as it is being done, rather than having two hours they would normally have to use at the end of the day to make note of the progress on the job.
Sergey says they are staying focused on the construction industry and not branching out right now. I was curious to know how Raken came about - where and how did he get the idea?
He was a late stage co-founder for the company so the idea wasn't his. But in general ideas come from two different sources. The first is industry insiders who have been working in their field forever and eventually start their own business to do a particular thing in a better way.
The second source is industry outsiders who see a better way to do something that others haven't seen.
Their co-founder, Kyle, fell into the second category: he decided to create Raken after recognizing that the construction industry lacked a reporting tech solution that could alleviate major pain points. So Kyle set out to fix that with Raken.
As a CTO with a rich history in software development, management leadership and previous CTO roles, how did Sergey know he wanted to join Raken? 
He met Kyle about a year into his 2-year earnout from his previous company. At that point, Sergey knew he wanted to join another start up. He knew he had three choices: he could form his own start up, join an existi

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Have you ever found yourself working on a side project because you thought you had to and not because you wanted to? Our guest for this episode of CTO Studio has and he also found out why it’s okay not to finish that side project.
Evan Phoenix is the lead engineer on the private Terraform enterprise  at Hashi Corp, and the Director of Ruby Central. He’s also been a CEO of a start up and regularly finds time to try out side gigs of his own.
Today he tells us how he carves out the time for fun engineering projects and why sometimes it’s okay not to finish those side projects. You’ll hear from Evan on those topics and more on today’s CTO Studio.
In this episode, you’ll hear:
Is it okay to do something even if you think you are not the right person for the job?
Why everything we do doesn't have to become a business.
What is the "for market" challenge?
Why does he prefer Go over Rust and C++?
How to put the fun back in your side projects.
And so much more!
 
We start off by talking about Evan's scariest childhood movie and how we met at a Ruby conference and became friends. Then we segue into talking about his current role at Hashi Corp: he is the lead engineer on the private Terraform enterprise.
He came to that position via his previous start up, Vectra. Vectra eventually became a logging SaaS and Evan and his team worked to build it for 8 or 9 months before their financial runway was depleted. At that point, Evan had to figure out what to do next. 
After struggling with the decision, Evan realized he didn't like being a CEO and so they decided to close Vectra. Along the way, he and his team had been talking to Hashi Corp about what they were doing. When Vectra closed Hashi Corp invited them to come over and work there.
For Evan it was the best case scenario. He didn't like being a CEO, but he liked working on interesting problems and have some say in what he worked on. Hashi Corp is the perfect place that allows him to do both.
I was curious when he first thought of being the founder of his own company, and why that interested him. Evan explains he wanted what he thinks every founder thinks they are getting when they start their own company: control to do whatever they want to do. They make all the decisions. If they don't want to do something then they don't do it, and vice versa.
But the reality changes when the business involves more than just you or you and another person. If you take on investors you no longer have complete control. In Evan's case his family and friends invested in his business so not your typical investors, but he was still aware of risking other people's money. And that awareness changed and altered his own risk tolerance.
So now he gets to enjoy his work at Hashi Corp and have fun projects on the side. He says he start a new project every couple of weeks and he does it for him. We go on to talk about engineering simply for the sake of enjoyment, before we discuss his time at Living Social and Splice.
We also talk about how he manages his time as a family man with a wife and two daughters: when does he work on his personal projects? He tries to be kind to himself and he works on them when he has the time.
In the past, he would've beaten himself up for not getting more done on something, but now he doesn't. Instead, he talks to his wife and tells her he wants to work on something. She tells him she wants to do her own thing and then they do their own thing in the evenings.
On the weekends his daughters still have nap times so when they nap he works on his projects. But sometimes he uses those two hours to watch a TV show or do something - and he is now kind to himself about it and just does what he wants. If he wants to work on his project then he does; if he wants to watch Netflix then he does.
We then ta

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There’s a lot happening in the world of cloud services today and Jonathan LaCour of Mission is here to tell us all about it. Jonathan is CTO of Mission, a managed cloud consulting service based in Los Angeles.
On today’s episode of CTO Studio, Jonathan and I talk about all the issues related to cloud and cloud migration and owning your own data. Be sure to listen in to this fascinating conversation on today's CTO Studio. 
In this episode, you’ll hear:
Why doesn't it work to just throw people at a problem?
Why the CTO and the product team ultimately have the same goal.
What is the most difficult thing for most technologists?
What is the #1 most important value a CTO can hold?
What do people ultimately value?
And so much more!
Mission helped sponsor our first CTO conference, the same conference at which Jonathan gave a talk. So it's fitting to actually we recorded this show from Mission’s headquarters with Jonathan. We start off by talking about Jonathan's journey, how he became the CTO at Mission and what they do there.
Jonathan got into computing young, his dad was a Presybterian minister and also an engineer who went to Georgia Tech. His dad even worked on the space program, and has always been a technical kind of guy.
In fact, Jonathan's dad would bring home his portable computer when Jonathan was little. This computer was a Mac Plus with a handle on it! And that's where Jonathan started to code: on that little Mac Plus. He started with HyperCard and Pascal and eventually C, etc.
In high school he began writing code professionally and started working at an enterprise healthcare business. He went through a few acquisitions with them, including when they were bought by an enterprise document management business so he was heavily into enterprise in its early days.
From there he did a hard right into startups and went into business with his sister and brother-in-law. They created a type of SaaS application in the photography space called ShootQ.
They built out a cloud native app (back in the very early days of cloud) and grew ShootQ to become an industry standard, after which they sold it to a company in LA.
Which is how Jonathan met Simon Anderson (the CEO of Mission). Simon was the CMO of the company who bought ShootQ before he became the CEO of DreamHost. Jonathan and his family moved from Atlanta to LA so he could take a role with DreamHost. He had 5 different titles in 7 years with them. In those 7 years he did a lot of different things including building out cloud infrastructure, engineering management, etc.
When Simon became an entrepreneur-in-residence at a private equity firm out of Boston they worked together on a thesis for the managed cloud space, which is how they both ended up at Mission.
Also on today's CTO Studio, he tells us why the firm chose Mission (formerly Reliam), how they expanded to a company of 100 people today over the course of a year and what they do at Mission presently.
Honing in on that kind of growth in such a short period of time, I asked Jonathan to talk more about how his team has changed and evolved as it has grown. He explains that because they are a business that does a lot of professional services and consulting a lot of Mission's technical resources work on a team other than his team. His team represents the glue that holds things together. When he started it was just him so over time he has been pulling in people who are the best fit for what they are doing.
I also asked him how to decide which cloud (or clouds) to be in and he says it is about picking the best tool for the job. It's like any other exploration a CTO will undertake so the way he helps people understand the hyperscale cloud providers is simple: ultimately you are looking for someone who is going to provide you with as many sho

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Joining us to explain how CTOs can best utilize recruiters is my friend and expert recruiter Kimberly Owen. Kimberly has been a recruiter for 23 years, starting in London then Silicon Valley during the first dotcom boom. Now she is based in southern California.
On today's CTO Studio, we talk about what she's learned during those two decades as a recruiter in tech including why recruiters have a bad rap, what CTOs can do to make the most of their relationships with recruiters and what does the term "culture fit" actually mean?
Listen in for the answers to those questions and much more on the topic of recruiting in the tech world today on this episode of CTO Studio.
In this episode, you’ll hear:
What was it like recruiting during the first dotcom boom?
Why do recruiters get a bad rap?
What language should you avoid when listing a job description?
What is the proper format for a resume?
How can CTOs improve their relationships with recruiters?
And so much more!
One of my first questions was when should a CTO stop using their networks and start using a recruiter like Kimberly? She says it depends on how quickly you need the product development to happen. How quickly are you bringing your product to market and what is the trade-off?
Once you answer those questions then you can decide if recruiting is your best choice or if you should check with your network.
If you are going to use your network, her advice is to be active with your social media presence. You should specify on LinkedIn what you are hiring for - especially those top positions. You should be advertising those roles. If you have an internal person who manages candidate flow they need to get an outreach campaign underway and that needs to include your own network.
So after social media, what else? Kimberly says meet ups are an option but you need to know if these events are where people are asking for help and talking about vacancies and openings. If they are not then the meet ups won't help you.
And how can CTOs work on their brand and their messaging to ensure they are attracting the right candidates?
The job description is really important - she sees a lot of awful ones! Be sure to talk about the vision of your company and where you are going and what this person will contribute towards that vision coming to life. Candidates want a story. They want to know why do other people like working at the company, why would they want to work there and what life-changing things will they impact by being on the staff of this company.
In summary, you should be capturing the story that includes the vision and the values of your company.
Once you've done that be sure the job description is in the right places and having the right filters in place for whomever you enlist in your organization to sort through the candidates.
And if you still can't find the right person then go to a recruiter like Kimberly!
My next

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Who better to help us understand the psychology of people in tech than a former engineer now licensed psychologist?! Joanie Connell is that very person and she is here to talk about the issues CTOs face in leading their teams.
Joanie works with dev teams and technical teams on their communication. We talk about how she does that, what some of the common issues are regarding team communication in tech today and a whole lot more. Join us to hear more about the psychology of people in tech on today’s CTO Studio.
In this episode, you’ll hear:
What are the top challenges she sees regarding communication in tech today?
Why it's important as a CTO to expand your communication toolkit.
How can you deal with feeling triggered in the workplace?
Why addressing uncomfortable feelings often brings people closer.
What are tell tale signs you are too deep into the tech effect?
And so much more!
Before becoming a psychologist, Joanie was an engineer for eight years in Silicon Valley. She began as a data communications design engineer for Tandem computers. Tandem was one of the big computer companies back then right alongside HP and Apple.
Tandem made mainframe computers and they had parallel processors (hence the name tandem) for everything so they would never go down. One of their biggest clients was the New York Stock Exchange. She did data communications which meant she helped mainframes communicate with modems to other computers.
I asked Joanie how she made the switch to psychology - what happened that convinced her to work with the people side of tech? Joanie recalls she had gone into engineering because she thought it was a good stable job with a good income. She didn't want to be a millionaire, she just wanted a good living.
People had always interested in her but it became obvious when the other engineers were so into their work they would be debugging til 2am, and she couldn't wait to leave. She realized then that the work wasn't satisfying and she felt stagnant in her work.
One story she recalls is a time when there were 12 in their group and they had a manager who they met with once a month. They'd get into the conference room and you could feel the tension because no one wanted to be there. The manager would go around the room and each person had to update on their project. By person #12 everyone would be ready to leave. When that last person finished it was like school was out and everyone would run out of the room!
She saw the people she was with didn't want to be around other people and they didn't have the skills to work with others, either. Engineers are trained to design, debug and code and they are not trained on how to interact with others. Joanie realized this could be a space in which she could make a difference; she coulod help engineers and other tech people communicate better.
To bring more of her skills to the people side of the working world, she tried marketing and then consulting. But eventually she decided to go back to graduate school because she would find herself being pushed back into engineering roles and more technical positions. She realized she would have to re-specialize so people would see beyond her engineering background.
But before making the leap, she took some night classes in Psychology to be sure this was the route she wanted to go down. And before becoming a psychologist, she considered being a therapist or counselor. A volunteer experience on a hotline convinced her otherwise, so she opted for social psychology with an emphasis on organizations and the workplace.
After a few years of working for a consulting firm and teaching at university, she formed Flexible Work Solutions. Her company provides assessment for leaders and teams of people, her personal niche is with technical people.
What types of scenarios does sh

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What does it take to be successful and have longevity as a a CTO in healthcare tech today? In Larry Heminger’s case it takes optimism. Larry is the CTO of Sapiens Data Science, a company committed to increasing people’s life span through healthcare tech breakthroughs.
 
On today’s CTO Studio, we talk about how and why Larry joined the team at Sapiens, why he’s attracted to companies that are making a difference in people’s lives and what his Design for Success approach is all about. Join us for this illuminating discussion on today’s CTO Studio.
 
 
In this episode, you’ll hear:
Why doesn't he see himself retiring - ever?
How many years does it take for a medical breakthrough to make it to family physicians?
As CTO, how to make decisions that stand the test of scale
What is his Design for Success methodology?
What is the Snowflake Computing approach, and why did Larry choose them?
And so much more!
 
Larry is the CTO of Sapiens Data Science. Our very first topic is a dive into his journey of becoming their CTO. Larry tells us about his interesting ride; he had been working with ecoATM Gazelle for about 7.5 years and had been apart of their organization from their ealy start-up days.
 
Larry experienced a full 360 degree business cycle with ecoATM, going public through acquisition and then back to being a private company again.  The work they did (and still do today) was in the field of automated retail: recycling of cell phones.  Even though the work was amazing, he felt it was time to look for something new and different after his 7+ years with them. He wanted to do work that was meaningful and of benefit to everyone.
 
Using his experience with a previous healthcare start-up, Larry found a few new opportunities in San Diego that were health tech related. Sapiens specifically interested him because of their CEO, Brad Perkins. And Larry became even more enthusiastic after meeting with Brad, hearing of Brad’s passion and learning of their mission - Sapiens is in the business of adding more birthdays to people's lives. They help people live longer through the burgeoning fields of genomics and data science.
 
Next I asked him to describe his mindset coming from ecoATM, a company that was retail-focused, and then going into the health tech space with Sapiens.
 
Larry says there are many similarities and of course some differences. For him the key was and is feeling like he is doing something good. Like most of us, Larry spends so much time at work that he wants to feel like he's having an impact on people’s lives. For him it is not just about paycheck, it’s more the opportunity to help build a new, amazing company.
 
He goes on to say he believes healthcare will look very different in 10 years. One area in particular is the speed at which information becomes available to physicians, he says this will be sped up exponentially. Instead of taking almost two decades for your family physician to find out about medical breakthroughs, it will happen much, much faster. Patients will also be empowered with their own data and information.
 
My next question for him was where does Sapiens hit roadblocks with regulations and stereotypes? Those are definitely challenges they face as any healthcare company is going to be challenged with regulations, data privacy and security. Those aspects are all very important to the success of a healthcare company in tech and outside of tech.
 
Larry explains the basic strategy, something he calls design for success which applies to start ups as well as larger companies. It goes like this:
 
If you assume your company will be successful, and you draw out the architecture of your company with that succes

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What is it like to handle both hardware and software development needs? Anh Nguyen is a hybrid CTO of hardware and software and she’s here tell us all about it.
Anh is the CTO of Creative Electron where they build imaging systems that use creative electrons for the purpose of inspecting samples for defects. On today’s show she’ll explain how their equipment works, what she thinks about the state of women in tech today and her journey to the United States from Vietnam when she was a child. Hear that and more on today’s CTO Studio.
In this episode, you’ll hear:
Do their products create image renderings in 2D or 3D?
Are their offerings all custom-made? Why or why not?
How does their annual preventative maintenance work?
y/What was it like to participate in Hacking for the Homeless?
Why women should embrace being women CTOs and not just CTOs.
And so much more!
On of my first questions to Anh is whether they are mostly a hardware company or a software imaging company. Anh responds by telling us what her CEO likes to say: "What we are is a software company that delivers our product in a hardware box."
Although that sounds like something a sales person would say, her CEO actually has a background in EE and an MBA. He has come up with a lot of their ideas and how they have productized those ideas.
He works with her and their COO to come up with solutions that work for their customers.
Who are those customers exactly - who makes up their customer base? PCB manufacturers, electronic manufacturing services. She goes on to explain how their products work and why they are safe to use without protective gear!
My next question was about her responsibilities as CTO. Does she preside over a hybrid of hardware and software? Yes. Because software is managing the hardware they are very intertwined. As far as what hardware is going to be used and how things are integrated those decisions are all under the software stack. Anh and her team make suggestions on what is compatible or not.
We dive into the world of X-rays a bit deeper including Anh's explanation of how their imaging systems work in a variety of settings before talking about her journey to becoming CTO.
Was she hired to become CTO or did she advance into the role from a different position within the company? She became one. Her original title within the company was VP of Software Development. Then last year she became CTO. They have been growing and because software is so intertwined into their products that originally her focus was on maintaining and developing the software side of things.
But over time her CEO realized they needed to have a tighter relationship between software and hardware. He said it made sense for her to be CTO and to think about new strategies they can deploy and new technologies they can start implementing to grow their software along with their hardware.
Does she have direct reports from both hardware and software? She does and when asked how she manages both she laughs and says you just do it! She says it's the equivalent of working at a startup essentially. Making good software they do have to understand what is happening with the hardware so managing both hardware and software is a natural evolution. Because they are a startup you just have to dive in and figure things out. The main advice she would give others is to simply do it.
From here we get more into the mechanics of how Anh "CTOs". She doesn't have VPs she manages directly. She has three direct reports and then she will also talk to the manufacturing team. 
The person who does all of the CAD designs will come to her and her team to ensure everything they are creating can be fully integrated; they all want to be sure the software performs up to the levels the customers need which means having repeatable results and being ab

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If you saw a need or an opportunity outside of your industry would you recognize it? Our guest did and he’s here to tell us about it. Alan Leard is one of the co-founders of Limelight Health, a quoting, underwriting, proposal platform that started as an idea for an app. 
You'll hear the origin story of Limelight Health today as well as how it has evolved, plus Alan's thoughts on having four co-founders and making the transition into the CTO role. Join us for those insights and more on today's CTO Studio!
In this episode, you’ll hear:
Why four co-founders is the best number to have.
What are the three questions I ask every CEO before I join a startup?
When did he know it was time to make the transition into CTO at Limelight Health?
What are the ways they mitigate risk?
Why are the technical challenges of Limelight Health so attractive?
And so much more!
When I asked Alan to tell me what Limelight Health does he explained Limelight involves everything that needs to happen from the moment an employer says they are going to get insurance for their employees through the point when the employees are actually choosing the health insurance right for them.
The process is about providing accurate information on what plans are available and quote them accurately, as well as apply contribution modeling as far as how much the employer is going to pay and how much the employee is going to pay.
All of that gets wrapped up into a proposal that helps the employer make a decision. But how Limelight got its start goes back to one of Alan's first businesses: a make-your-own wine bar.
Before he and his wife had kids they wanted to do something together, they wanted to run a business together. When they came across the idea of a make-your-own-wine wine bar it seemed perfect and they set about making it happen. They ran their bar together through all the ups and downs that entailed.
That bar also led Alan to meet one of his future fellow co-founders of Limelight Health. It started after the wine bar had been up and running for about four years. Alan realized he was putting in 12 hours at the wine bar then coming home and making mobile apps as a hobby on the side.
Along the way he also met Garrett when Alan hired him as a musician to play at one of the bar's Wine and Roses events. Alan had also gotten hired with Accelerator in a support role - he mainly offered support for other developers using that platform. When Garrett began talking to Alan about an app idea he had Alan's ears perked up.
But Alan was no stranger to app ideas, he had so many people approach him with ideas that Alan had a series of questions he asked everyone who talked to him! The first was does that app already exist? Have you checked the app store?
If they had and the app wasn't already made (which was the case with Garrett’s idea) then he had a follow-up question. That question was do you know what user stories are? Garrett didn't so Alan explained to him what they are.
A week later Garrett came back with full-on wireframes and had written out user stories. So they built that app together, it was an app meant to help people find local artists online. After that Garrett saw the potential in his everyday line of work: insurance brokerage. This was about the time the Affordable Care Act was coming into existence and Garrett wanted to be able to help his families find the right options for them.
So they turned it into a lead gen app: you would plug in your household size, your income and location. The app would then tell you what your insurance was going to cost. There was also an in-app purchase which would allow brokers to have their customers quickly get an idea of what they were going to pay and then the brokers would help the customers sign up for a plan straightaway.
And that is how they found th

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On this episode of CTO Studio, we talk extensively about CTO authority versus CTO leadership with Michael Bastos. Michael was the CTO of a San Diego company called LocalStack before moving to Austin, Texas to run the benefits API team for the VA’s web site.