CodePath EES2024 EIGHT BIT STUDIOS - Freelance to Founder:Charting a Path from Side Hustle to Studio
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Join two successful tech entrepreneurs as they share their journeys from freelancers to founders of thriving engineering studios. This discussion will explore how freelance work can be a powerful stepping stone in building a tech career, allowing students to gain real-world experience, expand their networks, and even launch their own businesses. Learn how to navigate the freelance world, manage clients, and turn your side gigs into full-time ventures.
Hello people welcome welcome to this breakout session I’m super excited to be speaking with my good friend Don Bora about freelancing and getting into from a freelance mindset to a Founder mindset just want to make sure that y’all know we have a couple reminders one definitely use the chat we’re going to be reading through the questions that y’all put in the chat and going live there so if you have any questions throughout the session please just definitely drop it in there and after the session we’re GNA have a feedback form so please please please give us that feedback because it helps us improve all of our operations for y’all hope y’all love my background spent a lot of time preparing that and I’m super excited to welcome Don Vora Don is a Serial entrepreneur a professional software developer from Chicago he started nine companies to of which he’s sold don is the co-founder of 8-bit Studios a leading web and mobile application firm in Chicago and 8bit blends ux design and software development collaboratively to deliver digital products to customers in addition to 8bit and the work Don does there he mentors young entrepreneurs and Engineers alike so I couldn’t think of a better person to have a conversation about freelancing and Entrepreneurship as a technologist than Don he’s an outspoken advocate for women and girls in Tech and definitely a mentor to me so please give a round of applause or some love in the chat for Don Bora from eight bit thanks man that was so nice what a good intro can you hear me how are you I can hear you I can I’m doing all right I love your background I got my boring old background here but I’ll I’ll I’ll I’ll do a little reveal this is fake this is a fake brick right here so now everybody can be disillusioned and understand the the fakeness of my background are you okay C look like can you hear me oh no so can any can other people hear me yeah I don’t know I can’t I couldn’t hear him real quick oh y’all can hear both of us interesting gosh the minute I got thrown up on stage something weird happened all right can everybody hear me now can you hear me now cam can you hear me now oh this is not oh it’s all good Don they can hear you so can you hear me can you hear me I hear you yeah the minute the minute they threw me up on stage all my settings went haywire so apologize it’s all good it’s all good I was like I was like if they can hear you that’s great because I don’t need to hear you I was just revealing that that your dope your dope background my background is that’s a fake brick wall back there so well you you know what’s what the thing is is you are a seasoned entrepreneur you had nine companies you don’t need a nice background people are just gonna believe what you say you know like I have you got to bring something you gotta bring some professionalism right well just for a context y’all so I am the career l zone for CodePath and I spent a great amount of time in my role in Atlanta supporting engineers at the early stages of their career it’s like something that is deeply passionate that I’m deeply passionate about I’ve been passionate about for years and part of the reason why is because of people like Don who have spent their years as Engineers figuring out Pathways for younger entrepreneurial engineers and folks who are interested in Tech to get the knowledge that they need to develop their career pathway so Don I was curious if you could just give a brief like journey into your life as a technologist because it span several years and maybe talk about like what’s motivated you to Mentor younger Engineers the programs you’ve started to help engineers at the early stages just to kind of level set so folks know how lit you are and then we’ll talk a lot more about 8bit Studios and the entrepreneurial side of what your work is yeah is lit how we say old now is that the see I’m old I’m old saying lit now that’s how oh yeah yeah yeah yeah yeah I mean you know I I was lucky enough to graduate right at the right time with the right degree so I went to school for computer science and I graduated College in 1991 and then four years later the internet the first internet browser came out but when I was in when I was in college we were part of the University system that that had access to to what was before the internet called darpet and I was part of the there was like a it was a link a linked set of colleges and universities that were adjacent to military institutions and so I was right outs white outside of White Sands Missile Range and so like we had the research institute we had the internet in like 1990 8991 so I was very very very fortunate to have graduated then just as you know graphic user interfaces were becoming a thing just as operating systems were becoming variant outside of like what Mainframe was green screens were on their way out as I graduated so I I was I can’t even begin to say how lucky I was I got my first job out of college U they tried to put me in manag management and I’m like you guys are nuts I’m 23 years old I can’t even manage myself so I ended up leaving that company and going to an AI research lab and that that role right there that role switch going from like a corporate my first job was at motor Rola going from a huge corporation to a small research lab albeit at a prestigious University really set my path and ultimately allowed me to meet people that wanted to do something on their own and I just kind of happened to be there when that happened too so I like my mindset back then wasn’t naturally entrepreneurial it was cocky it was yeah I can code so let’s do this like I’ll build it and it took me years to understand like the the the Nexus of like business and being able to build software was a magic comination so it’s just a I was real super lucky man and and I’ve tried to to embrace that luck and to pay it forward as often as they can to to make sure luck surrounds other people too that’s awesome can you talk a little bit about some of the ways that you’ve worked with like early Engineers or like early career professionals since having that long background and the work you’ve done yeah so about about 12 years ago there was a boot camp scene that started up in Chicago and I quickly latched onto that scene if only because I owned my own company and I saw that as a pathway for early stage Founders to get educated and I was super excited by that and then I realized oh wow this is the way to train developers because what I would later come to understand most of what we do on a daily basis you don’t need a CS degree to do we are figuring out how to do things algorithmically and we’re also putting together pieces of software to make it all work if you’re trying to create something that’s been created before you’re taking a risk in creating a problem right so you go out to the open source Community you go out into GitHub or bit bucket or whatever and try to find something that somebody else has written before so so when I got involved in boot camps I started to see an opportunity for myself to really get involved mentoring and just being a sounding board for people that were interested in Tech that were interested in in starting companies I’ve since amended my mission statement by the way I’m a passionate advocate for women and people of color and Tech and I make sure to prioritize those people above the mes of the world because I think the mes of the world have have a lot of we have a lot of advantages already so so once I put that mission kind of out there it became super easy to say yes to Opportunities and then not say no to people but find other people that could help them and that’s that’s kind of the watch word that I that I live by if I can’t help you I know someone who can that’s so yeah I don’t know I you know I I don’t know what motivates me to do it I find it super rewarding and I guess you know unsolicited advice to anybody out there once you get enough under you once you feel like you can be of service to somebody and I guarantee no matter where you are in your life you could be of service to somebody it is so rewarding to do it I I highly recommend doing it I completely agree and just a little bit more added context I met Don as I was studying computer science in college so like most of y’all I was a CS degree holder in in waiting right so waiting to graduate studying computer science and I took a semester off school to do a coding boot camp one of the ones he was just mentioning and so it was really fascinating going from like a computer science degree track of learning in school to a boot camp and I’m sure some folks might be curious about like hey you know like after school maybe you’ve heard of like going and doing boot camps and things like that Don is definitely a a expert person to ask questions about that learning style too but one of the things that came up for me during that process was recognizing that as an engineer you kind of have to learn by doing right like there’s so much that you can do within like a classroom context but so much more of what you’re able to accomplish as an engineer comes from like the projects You’re Building or the things you’re doing to learn those new Frameworks and put your hands into the code and so don I know that 8bit as a studio you know is is a is an interesting type of business that most junior Engineers might not have been familiar with right it’s because I think often in college we’re we’re taught to think about looking for a long career at like a large tech company can you just kind of talk about like what a studio is and you know what career Pathways into like working at a place like8 bit might look like for someone who’s a college student yeah and first I want to shout out to Cameron real quick because you you you Embrace and embody that mentors that the mentor Spirit as well and I know you do a ton of it too so right back at you man it’s it’s it’s lovely work so a studio is for those who don’t know you know we’re we’re we’re a we would consider ourselves a boutique agency or Boutique studio so what that means is that we create custom software for our clients and we’re about you know at our best we’re about 40 people we’re we’re shrinking rapidly now and and kind of pivoting our company a little bit but I would say you know your your Studios or agencies are are in our ecos system is we’re about anywhere from 20 people to 160 people in Ser doing service work for for smaller or midsize companies and so you know these are a lot of companies that you that you may have never heard of before like most of our client roster no one’s ever heard of before every time somebody says oh what’s an example of something you do something you’ve done I have to say well how familiar are you with Chicago because like the the the the landscape in Chicago is where we begin and we have very few National brands on you know as like badges on our site because there’s a lot of work Regional and and local work that we can do so so the the our model is to do everything that we know how to do in-house so we have user experience we were founded by user experience design and Tech I’m one of the co-founders and our ethos has always been do the work that we know how to do so if we don’t know how to do it it’s not part of our core service offering we part partner with companies who can do it and that’s the studio model right so we don’t do video we have partners that do video we don’t do animation we have we have Emy nominated animat Animation Studios and animators and illustrators that we work with we do try to find real top tier Talent we work to work with but yeah studio is basically at its core like what we do at a at a core and then any kind of external Services we find partners and we work with those partners and I think it’s interesting because like the studio model is such an interesting place to work in as an engineer because you’re working with a diverse set of clients right like every project can look very different and maybe like as an engineer on working at a studio you might have exper you might gain experience working on a number of different projects and in a lot of ways I think it’s really akin to people who freelance right people who are like hey I am a full stack developer and I’m marketing my services as a full stack developer to to potential clients for higher how do you find freelancing Can how do you feel like freelancing can be a way for students to leverage their skills postgraduation to develop more experience in the industry yeah I think you’re absolutely right the people that we’ve had come through AP so we’ve been around for 16 years so hundreds of people have come come and gone through our through our team door right through the people who work with us and the people who have stayed with us are of that mindset like I want to work on different projects and I want you to bring me work and the average span of of an a bitter is about eight years eight years which is almost unheard of in our industry right but to answer your question and I think I might have forgotten your question freelancing can you ask it again I’m sorry I wanted to address what you said my bad so the work that you do at a studio working on different types of projects managing kind of those relationships and whatnot is kind of like a grownup model of like what it’s like being a freelancer and so I was curious if you could just share some insight on like the pathway into freelancing that students might find themselves in postgraduation and how you think that freelancing could be used as a way to help students develop their experience in the industry yeah okay thanks thanks so the the the the landscape of freelancing is is kind of there a lot to it so you’ve got you know basically how are you going to how are you going to start your business are you going to like build through your own soci security number you’re going to get yourself an LLC and build that way there’s all that minutia and I think that’s it’s pretty easy to figure that stuff out these days the harder part is the hustle going to finding clients and hanging out in the right places to go and find those clients so I know you had somebody on from y commentator yesterday you know going and finding your local incubators or your local accelerators and hanging out there to find the people who want to who want work done because those are people that going they’re not the people starting companies like that are not going to come to 8bit because our rates are like anywhere from 195 to 200 an hour they’re going to go to a freelancer whose rates are maybe anywhere from 65 to 125 an hour depending on you know your of service or whatever so it’s the hustle I think is is most of the game and building up your Prof portfolio through the hustle I think that in you know I think we’re in economic downturns still we’re kind of like we’re leveling off and one thing that’s true about economic downturns is that’s when people start companies and so you know when you’ve got these you know massive amount of tech layoffs in the rear of your mirror as you’re looking at at the landscape of like what am I where am I need a job if you’re looking forward you’ve got a lot of people like trying to start companies I I teach early stage entrepreneurs entrepreneurship at an accelerator and incubator here in Chicago and yeah that class is full that glass is full all the time it’s people starting companies so you know really when I you know when I look for work and right now I’m I’m entertaining fractional CTO level C Like Chief technology Chief Tech strategy opportunities I’m really just kind of like networking around the people I know and being pretty targeted about these are people who have decent networks these are people who know leaders in the community because that’s the position I’m going for but I’m telling you if you want to like if you just want to build stuff for people going into event saying yeah I build software I build web apps I build websites people people light up and it allows you to like refine your elevator pitch in real time because you’re just giving them a tease like I build things what do you build you know I I may be going a little a little too deep there Cameron so feel free to no you’re good direct no that makes a lot of sense and yeah I started my career in Tech as a freelancer right I was very interesting to be the person you’re talking about who after graduating from school not having like a full-time job lined up at a large company having those experiences like not doing well on technical interviews and you know transparently the like fear that oh maybe I’m not good enough comes up a lot and that impostor syndrome really hits but working as a freelancer and just saying hey you know I know one thing I can do is build a website does anybody need a website and you know starting off with those projects really helped transform my own sense of self and sense of understanding and yeah from there you know it’s like oh I got some money you’re doing this wow that’s awesome and it helps you really kind of understand that that pathway can really open up doors for you as just an engineer right and one of the things that I think is interesting too is as someone who starts working in that capacity right you you have to develop a lot of different sets of skills to do well as a freelancer and I think oftentimes moving from just like hey I’m an engineering student to okay now I’m freelancing folks have to learn kind of these fundamental Business and Professional skills what would you say like in your experience both like being a freelancer doing fractional CTO work and even running the studio what have been some of the skills that you feel like you’ve developed outside of your engineering skills that have made you successful yeah and real quick about the impostor syndrome stuff like dude I’ve used 20 languages professionally in my career and I’ve been told no and and I haven’t interviewed for a job in 16 years and I don’t think I would do well at it now but oh my gosh it was just like I I know I can build it just let me build it it it’s such a FR thing interviewing is such a FR thing so my heart goes out to anybody interviewing so what skills h I mean I like to say that I earned my MBA on the streets as an as an entrepreneur and quite frankly a freelancer and now that I’ve run a company for so long my freelance skills are on point just you know proactively sending status reports to to my I have a couple fractional CTO gigs right now so proactively sending sending updates weekly updates making sure that I’m meeting their expectations all the time because I’m not if I’m not meeting their expectations either I have to change or I have to go away that’s kind of the way I look at this engagement because it’s such high stakes as if when you’re you know when you’re kind of running the show for another company understanding how to or or I guess developing the skill of tech speak to human speak right I can I can make anybody’s eyes glaze over in seconds that’s a superpower of mine I can talk Tech and and you you know people around me have seen it happen were like oh you’re in check and I just start going at it and my my wife will be like what just happened versus being able to to to to boil it down into lay terms and have everyone kind of understand what you’re saying and that is a skill that will endear you to the non-technical people that are hiring you either the business people or or the the product people or the CEOs and every CEO I’ve worked with loves that about me that I can distill it down into something that they can understand because all they were hearing is tech tech tech tech tech and let me tell you something when I took one of the CTO jobs that I’ve got right now when I got there she had hired a neighborhoods neighborhood friends kid to help build her new piece of software he was too young to know what he was doing but he had a heart of go and so I’m like well let’s let’s let’s get in there let’s see if you got it and what was happening was and I I I I saw this immediately we get on a call and he would very excitedly talk about stuff he had just done and about half of the words he were using were incorrect they were just wrong terminology I knew that but the CEO didn’t know that the CEO just saw confidence and stuff that would that she considered over over her head and so she thought he was brilliant and I finally got on a call with her and I said I said look half he doesn’t understand half of what he’s saying right now so we just have to gauge our expectations and that’s that’s a that’s a big thing so you know kind of going in with I think communication skills are number one when you’re in freelance number one because communication skills help you build trust definitely yeah that’s if I could mic drop I’d mic drop right there that’s a quote but yeah the communication side of things is really important and I think as an engineer right you don’t often see the parallels between like hey I do code all day to I have to have to develop my writing skills I also have to develop my speaking skills I also have to develop my critical thinking skills outside of an engineering context and so I think everything you just said makes a lot of sense we have a couple questions in the chat that I want to definitely entertain for a second and but before we go into that I want to just ask you Don just plain and simple right if you were a student and graduating right now right as you were many years ago right how would you approach maybe entering into like freelancing or entering into like hey I just have learned for four years and you know I’m in between getting a job but I’m interested in using my engineering skills what might be some of the steps you would have taken I guess now as far as freelance it goes yeah yeah it’s a great question because when I graduated there was like that wasn’t a thing like the the help wanted ads in what was called the newspapers they weren’t there weren’t a whole lot out there and they were all Mainframe or you know like big companies it’s such an amazing place right now I think the the the most amazing way that the playing field has been leveled a bit more than it was maybe four years ago is the fact fact that and we’re actually seeing it as a company companies have gotten a lot have gotten very very very comfortable with people working not on site right and I know there’s a there’s a a a little bit of a culture War around return to office but the fact of the matter is that everyone’s a little more comfortable than they used to be so you know you can look at that and say okay but there’s all the Nearshore and offshore Talent that’s going to be that’s going to be recruited and to that I say yeah but yeah but you can get a job in San Francisco if you live in Iowa and charge less because you don’t have the cost of living that San Francisco has and you can start building up your portfolio in a way that you couldn’t have done beforehand so I for me this is kind of this is a magical time AI notwithstanding this is a magical time to be able to Leverage like remote opportunities and get out of your city or out of your area to try to find gigs there and you know there’s all kinds of websites and all kinds of like forums and and you know social media platforms that can help you find those people who are looking to get that stuff done yeah I would say three that are helpful LinkedIn for sure Reddit Twitter even right networking through like even through GitHub and like finding opportunities by way of looking at issues I know folks have been talking about open source let’s say like a college student was trying to petition themselves for like a job at8 bit right and they’re like hey I’d love to work as a contractor maybe you know let’s let’s assume you had the budget for for everyone to get hired right how would you want someone to approach you as a a founder of a studio to best demonstrate hey you know I’m I might be an entry level talent but I I’m very excited about this opportunity and would love to be working at or you nailed it you that right there and and and we get this all the time all the time and it’s my it’s our policy to answer every email we get that way and so sometimes we’re very very busy answering all those emails and you know we we kind of like file them away to look back to when we have opportunities that are available so yeah we’ve got we’ve got nothing right now just I’ll put that out there we have nothing right now but just that like come in with you know email or reach out on LinkedIn say exactly that like just like hey I’m a junior blah blah blah I’d love to get five minutes of your time or whatever or I’d love to you know I’d love to learn more bunch of company and if you’re looking for if this is a more general question of like like you’re going to a company and you want to learn you you you legitimately want to know about opportunities there and rise above the the fr tell them something about their own company tell them what you specifically love about that people love hearing about themselves and when somebody comes in I know it’s happening I know it’s happening I know the psychology of it but I can’t help but be affected like oh they know my company oh wow that’s cool now the thing that is the opposite of that was somebody gets on a call with me and has hasn’t even looked at the website and they’re like wait what company is this again I’m like oh yeah we’re not no can’t keep going yeah that that makes a lot of sense and I think that being proactive reaching out and having those conversations is is really key so one question from Stephen Smith in the chat was when freelancing as a student what are some basic legal things that they should be aware of right so freelancing as a student I think a couple of things it’s helpful if you have your own LLC they’re extremely easy to get and you can go to your probably like Legal Zoom or go to your local state government website and fill out the forms I think it’s about 400 bucks so you know for a student it may not be cheap and once you have that now you can start billing under that that Fe that the business version of the social security number if you’ve got multiple clients the government loves that if you have one client the government doesn’t love it so much but if you’re not full-time employed somewhere it’s fine find a good invoicing way to invoice honestly we just had a freelancer that joined us who didn’t know how to invoice and I found that very strange so we helped them out we helped them figure it out but know how to invoice is is Big you can get there’s like if you just look for free invoicing software you’ll find like premium versions or low paid I myself use freshbooks that’s kind of how we started Studios before we grew out of it I still use fresh books to to maintain my clients and it it it what’s nice about that is then I can just give my accountant a log into the system and and and that’s all that all that’s all handled if you are freelancing you have to make sure that you’re taking care of your own unemployment Unemployment taxes read up on that understand what that is and you don’t have to file quarterly you I I file once a year but it’s recommended that you file quarterly I would talk to an accountant talk to an accountant find someone that who knows someone and I will also say that accountants are always always a little weird to deal with there are there are fewer and fewer of them around so the few of them around that are around are very very busy and the first time that you like the tax deadline is coming up and you don’t have your stuff together it’s freaky it took me years to get over that I don’t worry about it anymore I never file on time anymore and my accountant handles everything and that would be true even if I were just like freelancing like I used to freelance so I hope that is enough detail for you Steve right Steve Stephen yeah you went you in I I would say outside fresh books QuickBooks is another great platform for invoicing bill.com I know we got K have has a great partnership with bill.com bill.com yeah yeah yeah yeah so those types of platforms are really helpful because what Don is trying to get at is as a freelancer you’re responsible for sending in how are you gonna get paid and so you have to be responsible for your own systems for managing payment most times some some organizations will cover that on their behalf but when you’re freelancing you want to make sure that you have a means to get paid and so yeah knowing how to send an invoice to Don’s point is the standard way of essentially saying here’s the amount of services I’ve worked on and are billing for and getting someone to be able to pay you for those Services yeah and and on the detail there you know make sure that there’s a like a term on the invoice so pay within 30 days or pay within 15 days you’re going to you’ll get push back on that from some companies they like no no no we’re 30-day cycle fine that’s fine but at least you’ve got something to start a conversation with first off second off make it as easy as possible for them to pay you that’s it so I have a ready to go I don’t want to do credit cards because I don’t want to I don’t want anybody to pay those fees so I do a or they can send me a check those are the two easiest ways because if you’re sending if you’re if you’re getting a couple thousand dollars for a job going through something like zel or venmo can be problematic because the bigger numbers will flag them in your system I had somebody who was trying to pay me through venmo and the big number flagged it as fraud on both our accounts and it got weird yeah I know you’re not I know you’re not doing any fraudulent activities so so so yeah freelancing is actually really interesting because of the fact that you have to work in this capacity but it’s really rewarding right because you get the opportunity to create some of these systems for yourself that can last you very well and help you in the process of developing out of that freelancing space and time to a full-fledged company what had been some two questions one for you Don is when you think about that like the early stages of like your freelance systems and what then it turns into for being a bigger company would you say that freelancing prepares you well for like running your own company that’s the first question no and here’s here’s the longer here’s the longer so real quick I love freelancing because I love meeting people and I love helping people solve problems so for me that is like I get to do that all the time whereas when I’m at a company it’s it’s it just clicks a different speed for me I don’t dislike being at someone else’s company but it does I find it is limiting for me and I have a limited lifespan in in that in that framework well I meant more like your own so like going no no no no no yeah I wanted to address what you said earlier the thing about running your own company is once you take on employees you have a whole slew of issues that almost nothing can prepare you for payroll benefits cash flow how when money comes in the door and how to get it out and making sure that you’ve always got enough in the bank account to pay people so making sure that you’re you’ve got a s let’s say let’s just say you got a 60-day pay cycle with your people which is not cool it’s probably going to be 15 and you got a shorter pay cycle with your with your clients so that you got that cash flow there and you can you can build up money people quit you post jobs there’s application processes those are changing all the time due to a whole slew of things I mean you know last year I I have been a Dei guy for over two decades and there was a term for it until quite recently so in the past two years I was like this is awesome like everyone’s speaking my language and now there’s a backlash and I’m like I don’t know what to do with this backlash I’m still me I’m still gonna do what I do but I have to be a little more quiet about it I don’t know it’s super weird so that whole like hiring people and and managing the human resources angle of it is very very difficult and I’ve talked to so many Founders and people who run companies who Echo this when you hire HR it’s already too late that’s funny so it’s different you’re saying there’s a difference in like you know working for yourself as a freelancer like you’re self-employed and doing it for yourself than like running a company having to deal with like building the team and the kind of nuance to that yeah because now I gotta keep in my so the way I work my default setting is I have to keep all these people employed that’s the way I look at it so when we were up almost 50 people I was like that’s a lot of families man I’m not just taking care of my family I’m making sure everyone else is taking care of too it’s a it’s a big responsibility I think you’re right and it’s interesting kind of that you like call out that Nuance because you know some folks might not really know the difference between like hey like is it that I want to run my own company or is it that maybe I want to be a freelancer and just kind of work for higher and do some stuff as a contractor as a consultant in a way well go real quick last thing I’ll say on this is I t so I’m I’d like to consider myself an empathetic person and I work at it very hard and so I’m always kind of like eventually within seconds getting to that empathy point however I also like to move very fast and I also don’t care about the details which is which is not a great thing for someone who’s running a company because people care about details and if you’re making a move as a Founder as an owner people want to know those details if you’re affecting somebody else’s lives they want to know the details and what I found invaluable was surrounding myself with people who also want those details at the leadership level and they help me figure out how not to I don’t know be a jerk or screw things up all the time yeah I think that the details and there’s different like there’s different types of archetypes of like what it means to be like to run a business and the types of people you need to support you in those early stages one person asked a question about like you know when it comes to finding and being a CTO right because you’re now doing like freelance work in that space how do you see how do you see like the pathway for someone becoming a CTO and what do you think is required to become one so curious like both from your experience like working with like larger companies who may or even you know middle-sized companies that might need this but also if you’re someone who’s starting a new company you’re running a startup and you’re like I need a CTO what would be some of the qualities that you’d look for out of a CTO and how do you recommend that folks especially emerging Engineers enter that pathway that’s a great question because I’ve thought about this a lot and and you know you probably know this that I’ve fallen on different sides of this argument when it comes to the CTO role so fundamentally CTO manage the technical strategy of a company and it’s externally facing products or Services and a CIO tends to F tends to be internally focused and less technical so on the CTO side it’s all about understanding the basically how a business runs and how to how to work in service of that business so understanding what a a profit and loss p&l statement is understanding budgeting and how to work within that budget and how to build a team and how to keep track of what technolog is being used and how to push the envelope and depending on your industry how far do you push it and what technologies do you use and kind of being a little ahead of the curve on well this is not a popular technology and if we’re going to build something we want around in 10 years we probably shouldn’t use it type thinking so those are kind of all the like like ground level details around CTO as far as like the path to get there I’ve got different opinions on this normally Founders non-technical Founders think they need either a technical co-founder or a CTO to get off the ground I push back against that all the time you don’t you don’t need a full-time CTO or full-time Tech founder which you need is Tech expertise and you can get that by putting together a professional Advisory board or or an actual Board of advisers but I’m actually in talks with a company right now and they they’re looking for fulltime and my position is you don’t have anything right now in existence so anything I would do would be at Max part at Max half the time half like maybe 20 hours a week I don’t know what I would do at 40 hours except for just eat up your money and I want you to succeed badly so let’s not do that let’s not eat up all your money on me let’s take that money and build a team so they can deliver because we at my career level I’m not the one going to be in there building the software most of the software I can get my hands dirty but I’m not going to be as up on the latest emerging Technologies as probably you all in the audience are so I would much rather you all build that and I’m keeping like the very high level strategy in mind so I in my opinion I think like you know you can probably start looking at the CTO position I think I’ve seen as early as five years under your belt I’d say between five and 10 years you kind of start like knowing what’s going on but if I’m looking for a CTO for a company they have to have seen some stuff they have to have seen like major server outages they have had to recover some big issue or problem they’ve had to build something not necessarily at scale but but build and launch a couple of things but I really if I’m looking for a CTO I really want to know how they manage the failures I need some big failures on their resume and I know that sounds counterintuitive but the the fact of the matter is there’s always going to be a failure and in the team has got to know how you’re going to handle that failure the company I’m fractional at right now they had a server outage their server ran out of space they’re using not they’re using out ofd technology and I’m helping them rep platform to something else but we’re still on that old platform and there’s nothing we can do about it right now except manage that platform so you know when the server when it ran out of space I did not panic I figured out how to get it back on track and then I wrote a small little script to delete those log files every night so it doesn’t happen again but you know I’ve seen this before so I just you know I kept my cool and I told I told the CEO exactly what was going on and you know I told her that I was working with the the vendor to figure things out and he just kept her in in lock step in Loop the whole time so she could go do her job and be confident that everything was being taken care of that makes long answer long it makes sense it makes sense that what you’re saying thing is kind of gets back to the idea of like you know as a student and and as an emerging engineer right now you’re trying to create experience and finding experience is like the number one thing that you need to grow your career as an engineer and one of the the reasons I wanted Don to have this conversation about freelancing is because in my opinion freelancing is a great way to start building some of that experience you start seeing stuff like he’s saying right as you’re building projects for yourself you don’t necessarily push the envelope so much as if you’re building something for some someone else based on what their requirements are based on what their needs are identifying how do I go from what this person has in their head as a vision for a platform and help them deliver it and the skills that come from that are typically professional skills business facing skills communication skills that allow for you to grow your career in really significant ways on the non-technical side but on a technical front You’re Building these really interesting projects that are are vary because each person you talk to about a project wants something different and in that you’re gaining this experience seeing a lot of different things that eventually help you have a mental model kind of to go back to what Nathan was saying earlier today about the future like hey what could go wrong in the system like this right oh I’ve seen something like this in a in an old project or in an in a different client that I worked with and those experiences I think help you advise people about their technology choices and that advising of people on their technology choices I think to Don’s point is what what people want out of a CTO someone who can think through the strategy and help them identify what are maybe points of failure here and I would also say that those things trickle down right as a senior engineer even you’d want to still kind of develop those same types of skill sets to be able to at every step of your career be able to talk more about hey if we go with this particular architectural Choice what might be some of the consequences in doing this what might be other Alternatives and developing that type of of communication is one of the core things that can help you level up your career yeah and to to build on that Cameron you know the years in service allow you to get an understanding a mature understanding of what is possible and what is costly right and so like it like five to 10 years in you’re going to be like okay there’s a cheaper way to do this or okay you know we can do this we can do this a little fancier we can add this XYZ over here and it’ll allow you to say that’s gonna that’s G to cost more than you’ve got and and and when you get to the CTO level it’s about does the business really need that and what’s what are the goals that are driving that and are there any sales or marketing targets that we have to know about when we go into building and and to put a bow on that Cameron I I’m working with an engineer who’s I’m not a JavaScript guy in fact I hate JavaScript and everyone everyone who knows me knows that but we’re in JavaScript on this on this platform and I can’t deny its popularity and and its performance in some instances and you know what we’re doing is is kind of complicated and and I had this I had this way in my head of like how the database was going to be grown and my developer came to me and said hey I’d like to do this and the minute he said the words I was like oh I forgot that was a thing that’s perfect yep do it and then sometimes they’ll come to me and say hey I’d like to do this and I’m like you know what I know what you’re saying and it’s a good idea but we have to hold off on that because it’s not it budget-wise it’s not the mo right move right now I think we’ll we’ll take on that Tech debt for a little while longer and we’ll push the threshold of when it’s accept when it’s like we really shouldn’t wait any longer we’re gonna push that threshold to get other things done first so it’s just kind of having enough years under your under your belt to be able to defend those positions yeah that makes a lot of sense the the years in the game building projects helps you in the communication of what can you do and what maybe is possible but point to also put a bow on the bow you put on that is this is why it’s super exciting to be a junior engineer right now even considering this because you have an opportunity to look into more of the technologies that are going to be the trend in five years and say well hey I’ve been looking at this for five years right so now I can tell you more about whether it’s like hey you know a lot of Engineers are talk talking about building an AI or building on top of the the llms that exist now and the different Technologies in that space but imagine five years from now right like if you have that expertise of I’ve been building projects here maybe have worked on small things for cl a little couple clients you become that you become that person that people can say oh wow like your experience gives more context to decisions that we might have as an organization later one other question Don is to Pivot us back to some student questions David in the chat asked he’s someone who’s working as a part-time Solutions architect shout outs to you get in the bag he said he’s had trouble managing client expectations and having them constantly change requirements it’s a bit difficult communicating past that technical Gap any tips that you might give to someone like David yeah I would say and something just happened to the screen so I GNA make sure people can hear me still can you hear me yeah we can see you they’re just showing yeah yeah documentation document document document document and communicate and it’s you want to what you’re trying and you’re working a very fine line here and your position is is it’s unenviable because it happens all the time and you’re not trying to litigate the past you’re trying to make sure people understand how we got here and it this is wow this is a this is a communication issue 100% it’s funny I took a I became a certified coach a few years go and that’s where I see my coaching skills come to life when there’s that kind of like a a fundamental either misunderstanding about what was communicated or a a continuous change in what is what needs to be done so documentation make sure the timeline on the road map is well understood make sure like everybody on the team including the product people understand what’s being built and when it’s being built and just over and over and over again that’s that’s the only way to address that problem sorry I don’t have an easy one for that but yeah that’s that’s a that’s a big one that’s a big one for sure managing client expectations is the is the is the work that helps you grow as a professional though and so to Don’s point I think documentation is like one of the things that allows for you to in advance kind of communicate here’s what we’re going to do here’s the plan and get that feedback along the way whereas if you don’t have a clear documentation process it’s easy for clients to kind of get lost in the process of especially when you’re building something big and Technical right like it’s like very easy for people to get lost and as a Solutions architect your job is to kind of convey that big picture understanding of this big platform that we’re building and so you know what’s amazing you know it’s amazing today that you can do that you couldn’t do a year ago like you can you can have all the the the notes of everything and May may even a jurob board or TR what you were doing now you can pop that in a chat PT and say hey show me the history of this what happened and it could actually like pull together a decent narrative that would save you probably a good 15 20 minutes doing yeah it’s true that’s magic man I think the use of AI in like project management is like really kind of a great space yeah and like learning how to leverage those tools to your point down could be super worthwhile for students for sure so I think we have just a little bit more time for maybe a couple more questions because we’re right at the end of our session here D I do want to thank you for your time and all your Insight as always so I guess like one question is when students are looking maybe at like going into freelancing and and trying to find like that that those resources around around creating their freelance opportunities so like things like an accountant or things like the invoicing software where do you feel like they can go to find those resources and hopefully not in a costly way so two things of course the internet and you know and searching and figur and finding like what the you know you know top 10 lists are that that sort of thing or you know QuickBooks Alternatives or that you know the I guess the thing that everyone kind of knows about the thing I think is underleveraged a lot is peer communities find your peer groups and get in there I have a group of Founders that I rely on we have friendy a you know that’s like the don’t talk about stuff I want to talk about your stuff type thing and it’s huge it’s you know it’s sometimes it’s founder therapy it’s you know what’s going on in your world what can I help with here’s what’s going on in my world so I pure groups is huge because because every there’s always going to be a trend that someone else notices that you haven’t seen yet always always always always always and having a peer group is like find a slack Channel there’s there’s slack groups out there goal lore maybe find something local to your area maybe maybe an affinity like an affinity group or a language specific group like you know if you’re if you’re a node developer like find the node Freelancers that finding your community I think is I think is top top of the list yeah and you know I think for someone starting out right like a lot of the places that you can go to just meet people are like events and Eventbrite and platforms like Luma are great platforms so this kind of sours out like different events happening in your technology ecosystem and attending events that are not events for engineers is sometimes the best places to go because when you go to a place that’s like oh there’s an account since meet up on Eventbrite I’m not an accountant but it was free so let me go and just network with some of the people one you you might meet a great accountant but then two if you go to an accountants Meetup and say Hey you know I’m a student at so and so school but I buil websites right that might be how you land that first client and start your freelancing process right it’s going to those where you are you’re bringing oranges to the farmers market full of apples and saying hey I bring web development to a room full full of accountants and and walk away with someone who says oh I need some help with that and develop those relationships that way I I found that going to events has been really tremendously helpful in building out that Network like that I’m gonna borrow that orange and apple metaphor that I always say it that’s true yeah I think it’s interesting right like being an engineer and you go to a lot of events often just for engineers and it’s like well that’s like me as a farmer of apples going to a farmers convention with people who sell app app I’m it’s gonna be very hard for my apples to like shine here you know like Blue Ribbon State Fair contest kind of thing but if I go to a place where they’ve never seen an apple right and they only see bananas every day right suddenly now I become special right and so I think that that mindset and finding events that are outside of the industry could be really tremendously helpful for you as you’re building out your career looking for new opportunities looking for people who might need help and working with them there well Don thank you so much I think we’re right at time so I just want to make another just Round of Applause for you can y’all give my man Don some love in the chat I really appreciate your time today as always just insightful and just super warm and encouraging and so I thank you for giving of yourself always and being a mentor to so many folks we are I just want to make one more Shameless plug for y’all to fill out our quick survey your opinions matter very much to us and help us improve the op this this opportunity every every time we host and with that I will allow you to go don thank you so much and we’re gonna play a short video from our host Bobby D and I hope to see y’all at a future session thank You’ all so much thank you so much Cameron thank you so much it was great thanks thank you thank you for joining us in this session I got some information before you leave it says please take a moment to complete a brief survey to share your feedback remember how valuable feedback is I’m trying to come back three years in a row and it’s all based on feedback right to see what comes up next I want you to head back to the main stage and check out the schedule see you soon in the next set of sessions I




