fractional work and ai w/ reed tomlinson, cto

full transcript

auto-generated from the audio, so expect a few typos. the audio is the source of truth.

all right he says we're live that doesn't mean anything yet send this good morning everybody uh I don't know if anybody's here yet but good morning um let me see here waiting for the notification on YouTube and Linkedin all right got the notification on YouTube and we're good on LinkedIn you know what linkedin's been like sneaky good lately in terms of getting this live the last thing we want to do is like go live I've done this before like two or three guests like I'm like yeah yeah yeah yada yada y then all of a sudden like it never went live we had to restart

the whole thing so everybody good morning uh welcome Happy uh Monday welcome to guidance counter 2.0 we are uh live a little earlier this morning um it's gonna be a good conversation when I say a little earlier like three minutes early please forgive me but I do enough yapping now where I feel like I need to you know I feel like I need to uh obviously um go live a little bit early but excited to have Reed so Reed Reed and I like I've known Reed for a while I've known of Reed um and I think Reed got connected with Corey by Corey Griggs the

great Corey Griggs um and so I'm excited to have Reed um uh finally back on the show so or not finally back on the show finally on the show so Reed thanks for coming on me I appreciate it yeah happy to be here thanks for right me um uh so before we get started obviously first and foremost say hey we'd love to hear from you um this is a networking platform right what I've realized over the course of the last six9ine months and re and I are going to talk about this probably a little bit today just around networking and this job market what does

it look like and how do you navigate it like things like like I want this to be a little Community for folks right so like we're not in a metaverse yet we're not hanging out on our Apple Vision Pro goggles yet and so I don't know if the only way I know you're watching is if you comment so please comment let us know where you're tuning in from also network with others like I'm really big on sliding to people's DMS and just saying hey so like literally just slid into someone's DMS if if you have stuck with me through the four years of this like

podcasting journey and you networked with every single speaker and every single person in the DMS over the course of the four years you would you you would be very good in terms of networking status so that's what I want for you today so please please network with read afterwards send a note tell them thank you and network with everybody in the comments but you got to comment because if you don't comment I don't know if you're there um watching so next thing is ask questions Reed is fantastic Reed has a lot of great experience especially around the leadership side fractional work um and so and

the job search and he even went to an AI conference recently so we're going to talk about everything so please ask questions if you got it I want to give a shout out to two of my partners this morning first and foremost that conference Hey listen folks I have five tickets to that conference I went last year I will not be going this year baby number two is supposed to arrive really close to this so can't make it but I have five tickets to give away I'm not get I'm not paying for your travel but five tickets to the conference uh that includes food um

if you so go check that out um if you do want tickets please shoot me a DM I will hook you up uh second off want to give a shout out to render ATL listen folks um render HL if you have not been there think South by Southwest in Atlanta it's a crazy event I've been there I've been there two out of the three years it was a 500 person conference the first year their third year they had 3,000 people they're shooting for more this year it's gonna be a heck of event I will be there can't announce what capacity yet but I will be

there so check it out render atl.com uh Richie it's good to see you JC my guy good to see you too Stepha nie it's wonderful to see you as well we got a few folks tuned in this morning again please continue to comment would love to hear from you um but I think that's it so Reed let's give the people what they want man who are you what do you do and we'll go from there yeah uh Hey Reed tlon I live here in Nashville uh for nine years now so you know almost almost considered a local uh I've been in the startup game for

almost 15 years now uh started in Chattanooga Tennessee you know doing some augmented reality startups in like 2010 right kind of early in that game uh moved to Nashville and have gone just to successively larger companies so I did you know uh bigger startups I did SAS I eventually went to you know like series D and then private Equity hated that got out of private equity and now I'm doing fractional CTO work which is uh which has been really fun so I've got a few clients here in town uh and just kind of living living that life I love it I love it all right

so lot lot to cover today uh what's going on from Illinois I love it Dr it's good to see you and Jordan it's good to see you my guy from Kentucky I love it all right so uh lot to dive into today I want to talk about fractional work at a high level right then we can talk a little nerdy about CTO stuff but man talk I mean I mean you've worked both right you've worked the full-time right and then you've worked the contract part-time you know there's so much to go here first off let me just give your general thoughts preferences Pros cons let's

start there yeah for sure so I think the the way to think about it so I'm I'm actually kind of on this journey too right I've got a consultancy and I'm looking at you know uh a personal assistant I'm looking at you know a CFO but I'm pretty early in this in this game right I've been at it for you know a year and a half now right in this iteration but I still don't need a full-time CFO I don't need a full-time assistant but I do need somebody so I'm looking at somebody you know 10 hours a week 20 hours a week and what

I need out of that which is really what people made out of a fractional CTO is making sure that everything is kind of pointed in the right direction right we making any decisions that are irreversible that we're going to regret later are we hiring the right people just you know does everything look like we're on the right track and and that's a big a big piece of what fractional CTO work can be so the reason that I get brought in is uh either you know we're starting something new we want to make sure we're on the right track right we want to make sure that

we're building things things to be future proof um a big a big one and this ends up actually being most of my work is we've been going for a long time and something has gone horribly wrong right right and people I think don't realize that about about this fractional work is a lot of the times you're kind of jumping into a crisis right job to like redirect things and get things pointed in the right direction um so you know happens to be a skill set of mine uh you know it's it's uh stressful when you get there but really rewarding when you actually turn things

around so yeah um those are really the the two big ones um you know the third is we just need somebody on paper right we need to we need to be able to put somebody on a slide deck that we say is our CTO that one's less common but you know if somebody's going out for fundraising that gives investors and and you know other folks confidence that hey we've got somebody who's making sure we're going in the right direction so yeah absolutely um so so let me let me ask you this like for those I do want to talk about job security from a contract

fractional versus full-time because you've worked both what are your thoughts just on job security right now and this Mark because I feel like the traditional side is full-time jobs salar it's safer but man I really truly think over the last year year and a half I feel like peo ple are like uh that's not really a thing anymore what are your thoughts on that safe yeah yeah it's a it's a good question um I think the thing that will keep you you know that'll make you the last on the list to get cut uh at a full-time job is the same thing that will get

you repeat contract work as uh a contractor which is just make yourself indispensable and also just like be somebody that people like working with that actually goes really long right yeah people if you've got three people with equivalent resumes and there's a bunch of people out there with equivalent resumes right now you know you're going to choose the person that you enjoy working with the person who's help ful the person who responds quickly uh so that that interpersonal stuff really is it goes a very very long way um but yeah it's a it's a good good question I um the market is is pretty weird

right now where if you own a full-time job that doesn't feel necessarily very secure but there's also a bunch of people who are out looking for contract work because of layoffs and so it's a very kind of flooded market so it's a you know it's always a tough call I think now is actually a really good time to be a contractor because there are so many companies that need help but they can't commit to a full-time hire you know more of their budget is going toward contractors right now um and then you know I've gotten a bunch of repeat work from different clients by you

know just being the guy that you know they know can do the job but also in between if they reach out and just have a question you know I'm always there to help I'm always going to answer their question question make sure they kind of understand it and so I'm kind of that go-to guy right so that that really helps with the pipeline where're man you said so many things I want to unpack let's let's talk first off kind of keep on the contract full-time route um how can people if people have never done Contracting before um you know I I I know I'v e

had some folks you know reach out and be like do I need to start out an LLC you know in my experience I don't think you necessarily need to start an LC I don't want to get too Financial because we can get pretty that's that make a lot of people's eyes glaze over but like like what are some checklists like if people if somebody was laid off today from their full-time job what are some like five steps on how to get started with Contracting yeah for sure so the LLC is a legal instrument right it's about Indemnity and kind of contractual safety um it actually

can make people more comfortable signing a contct with you if they're Sig company instead of you okay but you know that comes with overhead right and Contracting is is just all about overhead because now you're you're your own legal department your own sales team marketing all that stuff yeah but the list that I would go down is you know One update that LinkedIn get back out there start engaging start posting start engaging with other people's posts just kind of get on people's Radars so that when they think about hey I need a contractor you're top of mind because they just saw something from you yeah

right so that's that's one um two you know I mean this is not just a plug for gun.io but like there's there's really good Marketplace out there yeah where they take some of the you know sales funnels some of the um some of the marketing motion off of your plate and now you know you don't have to worry as much about that um you know start networking go out there if you can afford a co-working space you know go there and just like be the guy who hangs out by the coffee machine and his chatty if you uh if you've got you know uh technical

talks you know give a talk about something that you're that you're interested in and then I think right now with the market as kind of saturated with with people as it is today like so many people have been laid off so many people are looking for contract work um find a way to to diffe rentiate so that might be it might be something technical that you've learned like you know I I worked in devops and I've got some devops experience that a marketable skill set so I'm going to kind of tailor my LinkedIn and my resume to that but there's a bunch of soft skills

and a bunch of life experience that you can use to differentiate you right if you're just trying to be the best coder in the room that's going to be hard I've I've tried that in the past it's never been true I've never been the best coder in the room uh but I've got you know communication skills and I've got some life experience in you know a little bit of construction and working for the forest service and these areas where I know the subject matter and I know how to code and that opens up a niche that I can then go and Tackle so if you

you know if you've got a background where you understand small businesses then go out to small businesses help them automate stuff help them with their processes if you've got you know a background in in like agriculture gardening permaculture like go find an agtech company right like find a way to differentiate yourself so that you're not just another developer in this extremely large pool of developers looking for contract work so you said another thing goodness graci I'm so glad I'm interviewing you because you've saying so many things want unpack it seems so so my observation but you kind of hinted at it too I so I

think that during the boom of 2020 late to 2022 it was we want to hire journalists like we want to hire polyglot Engineers who have a ton of different languages who can code it all because we're just gonna throw them at problems and see if they stick yeah I feel like that's not a thing anymore now it's like hey we need to solve a problem with our frontend architecture using nextjs and something something something and so we need this person to have these three things have you seen that yeah I mean I'm I'm helping a couple of companies hire up pos itions and it's it's

exactly that it's you know we how far could we get with contractors and now that we have a demonstrated need you know it's just just being a lot more careful about taking on a full-time hire and so the the the need has to be more demonstrated and more specific so yeah I do think like it it's not just you know I need a devops guy it's like I need somebody with exactly these three things and you know it's now a much more tailored role yeah yeah and I think that goes to people if you're watching this now in the future listen this in the podcast

um like that's where writing your resume getting as granular and as specific as possible you know not like I solved a task using react it's what's the task you know how long did it take how many users was it for do you use more than just react give me more of a breakdown so that's where it comes really into play because you have folks like Reed looking at your resume and Reed I don't know if you have any resume tips at a high level but I feel like that's one of them yeah definitely yeah be be specific about the the problems solved the tech you

used and the metrics right like what how did this actually move the yeah another another thing that you've brought up too over the course of this conversation especially like you know when I ask you what do you what do you do when you were laid are laid off a lot of what you said is just putting yourself out there like you didn't really say go get a certification go heads down on Udi courses or you know do hacker ranks you were like go go Network go speak go post on LinkedIn so like can you expound on that a little bit more why that's so important

instead of just bearing your head in a bunch of technical books and stuff yeah for sure um and you know there's there's value in that like I there was a point where I was kind of looking to move on from from one job and so I just went and got every AWS certification that they offered at that time which which I will push back if there's one place where I still think Sears still matter even I've been saying this now for years I still think cloud CS I think still matter so yeah I agree um good job good job so yeah thanks there's just like

so many there's like a thousand AWS Services now and it really is just like knowing that you can navigate your way through it yeah um so doing that getting all those shs actually did Lan me that job in in private Equity um which you know I did for exactly a year and there's a part of me that is dead and it's never coming back because I worked in private Equity um but you know that that landed me that job every other job that I have gotten and this is contract and full-time has been through my network and that's you know going back 15 years um

so yeah get out there you know support people who are who are out there doing stuff right comment on their stuff like it you know LinkedIn is just such a good place to do all this U but any networking events if you can go to them if you've got that capacity uh do it and and it will help again you just want to be you want to be top of mind because every time somebody is putting out a job description whether it's intentional or not the first thing they're thinking is do I know anybody who fits this bill yeah that I've worked with before that

I like working with that I can hire today yeah absolutely Jesse it's good to see you man Jesse graay stopping in it's good to see you buddy um and Eugene it's good to see you uh as well um all right so talked about little fractal stuff part time again let I I want to tie a bow on this do you think people should be more open to Contracting now I think it's a lifestyle Choice hly um but with the way the market is today if you're out there and you're looking for a full-time job take some contract work in the meantime like I guarantee you'll

learn something along the way and that will be valuable and you can use that for your job search and and interviewing for a full-time job so I mea n there's obviously a Time right if you're if you take on a contract and it's going to be like a 90day right that postpones when you can start a new job but yeah there's there's very little downside to making a contract G 100% yeah I I I TR all right let me ask you this though let me ask you this let's talk benefits for a quick second right so this is the biggest problem with with people benefits

benefits benefits so I'm gonna be honest I so when I left my last company um I didn't know how fast I was going to find a rooll so I just went out and I I just I went I I asked some people and my financial advisor um he works at a small shop so technically he's a 1099 like you don't have benefits so he like I just went to Farm Bureau and it's and and it's like anybody can get it and I got it and it quite honestly is better than my last company's benefit so it was easy for me so like and again I

may maybe naive here and maybe it varies between state to state and the access of benefits I don't know that this is not my subject matter at all but like what are you doing for benefits how easy was it for you to find benefits I feel like that's just the only stickler for people for contract is just benefits that's it yeah yeah and there's there's a whole rant in there right like we we could be so much more entrepreneurial if have to worry about that yeah yeah I'm I'm just riding the Cobra train until until it ends right so you get 18 months you know

that ends at the end of the year and then you know by the end of the year I gotta gotta figure that out so yeah here are some things you can do if you if you end up you know start an LLC and you actually hire employees then you can get into kind of a benefits program sure it really depends on on your needs right like if you can if you can do one of the marketplace healthc care plans and that's good enough for you then that's fantastic uh you know me and my family we're kind of power users of our our health insurance and

so that's not qu ite going to cut it um so I'm I'm looking at at options but it basically is just like a deadline on growing the company to the the point where it can pay benefits that's that's kind of where I'm headed um but yeah there are other options and there actually there are a few companies that I don't have the names off the top of my head but they're they're kind of trying to tackle this problem of hey you're a consultant and you need better Insurance like let's kind of get a group together and then purchase insurance through that group there's probably some

options out there as well but yeah I mean that's that's kind of the hard part and if you were going to go out Contracting you're doing this for the first time you know most important thing every time you get paid take 30% of that put into a separate savings account because taxes are now your responsibility and sometimes people get caught by that okay um uh L luk comes in here goes I think it's important for hiring managers to stop looking at Contract work on resumes is negative I see it's a huge positive someone picks up contract work in between opportunities thoughts what are your thoughts

on this Reed yeah I definitely I definitely see it as a positive um because I've I've been there and and done it before and I think you know especially the last during Co and now this recent wave of layoffs I think you're going to see a lot more hiring managers who have done Contracting and realize that it is a benefit because again I mean you learn you learn so much from Contracting like I've got I have three contracts going right now they're all completely different things and I've I'm learning different things I'm applying different skill sets to each of them and so just that kind

of Rapid knowledge acquisition is is just really amazing so yeah I I think we're I think we're moving in this direction as well yeah absolutely absolutely Luke I'm going to be I'm gonna be honest I I I haven't I mean granted I'm not quite as Hands-On as I was um based off my role at gun but and especially just because primarily we specialize more in contract inside of things I I just I really truly feel like uh I haven't gotten as much push back as of late I know it happens again I'm only I'm only one piece of the puzzle but I'm sure it does

but yeah hiring managers you got to knock it off like we're not in the 90s anymore like people don't stay at companies for 25 years like you get SI you get if you get 18 months out of somebody like like that's good that's good so um uh uh Reed I want to continue on a few other few other things I guess I guess the really the big thing is uh talk about this AI conference you went to thoughts on AI just in general and and we'll go from there yeah um so I went to the Nvidia GTC conference a couple weeks ago um which was

where where was where was is that Vegas uh it was in San Jose oh nice okay cool right outside of um and it it was pretty incredible and you know at this point I think in the next week or so most of the talks that were recorded should be publicly available um so a lot of really interesting content there some of it extremely technical some of it you know much more like overview uh so I would definitely recommend taking a look at that um I was at a networking event and there was this college kid uh he had taken a week off of classes to

come down to this conference in San Jose uh and he was asking you know what should I what should I do after graduation right like how should I think about the job market how should I think about Ai and the advice from myself and and the other folks at the table was um you know go where you're going to learn the most and you know that's kind of what I did when I graduated college you know I went out west with the forest service for a couple years when I came back you know we were still kind of at the tail end of of the

Great Recession and the job market was kind of wonky uh and so I ended up you know going to small startups and and just doing things that were interesting uh and where I could learn the most and that really set you know the tone for my entire career uh because you know Tech is constantly evolving like you have to learn you have to be curious and you know you can go you can go straight to a giant company and have a very specific role and do one thing and and learn that but if you go to you know more Dynamic environment maybe a start up

you know a more uh a more Dynamic role you're going to learn a ton and you you stay there you learn as much as you can and then you can move move on to something else you know when you're there you you do it right you double down you learn everything you possibly can um but then you know move on to something else and just just keep kind of following that Curiosity um and I think that's going to become even more important with with the AI stuff so you know there's all these tools that are you know AI Junior developer right like um I think

it becomes even more important that you find a place to specialize and not just in Tech but in like subject matter right so AI might be able to do a bunch of Junior Dev stuff but it's not going to be able to uh you know figure out where to apply that technology so figuring out kind of the the problem area the the subject matter I think is is going to be where you can differentiate from an AI bot yeah yeah so are you using any a AI into your day-to-day I'm always curious with folks I mean I think the coolest AI thing that we use

is um we use fathom um which is like a note taking tool especially with um you know how many calls we on day-to-day basis you know I think it's just huge you know I can sit through a sales call now and pay attention to the person and not have to try to take notes like when I was recruiting my last company I freehanded everything so like I could never really be engaged in the conversation so that in my mind is like the coolest AI tool that I've used have you used anything that's pretty nifty yeah so I've got uh I've got some not taking stuff

I record everything I run it through a transcription so it's not real time but I've I've got the transcript after and then what I do I I put all of those uh plus a bunch of other notes and you know a bunch of other transcripts from interesting talks um you know hypothetical because uh you know copyrights and stuff but hypothetically I could take all talks from the GTC conference I could transcribe all of those put them into you know an AWS S3 bucket and then point a knowledge base at that and now I've basically got a chat bot where I can ask the conference questions

so I've been doing a lot more of that I've got some lines that'll you know get things into a knowledge base and that's been super helpful to be like you know I'm a little bit fuzzy on this topic like tell me about X and it will give me a summary but it'll also link me to you know five videos from the conference where I can go and review that stuff yeah so that's you know a little bit more like handrolled um that's something that I've I've done for myself um pretty much that and co-pilot are the only things I'm using right now but definitely you

know looking looking for more yeah so so when you say I so we're gonna wrap up here soon but I I don't want to I want to you know again confirm this reaffirm this so with Junior devs like AI is not going to take the place of Junior devs but it's going to probably assist on Junior Dev task what are can you maybe give a junior developers maybe watch in the future like an example of how to be specialized as a junior so like that doesn't happen yeah for sure I I think um where we are right now with well so too I'll answer your

question uh so the the AI tools we have right now they will spit out a bunch of code uh but it may or may not actually work right like they'll it's going to tell you the thing that it thinks is the right answer um but the skill that you really have to develop is basically code review and code review you know for every line that it spits out like does this make sense why is it doing what it's doing and really understanding so if you just like tab autocomplete you'll get it'll never work you'll spend forever debugging it yeah so that ability to to code

review I think is going to be super important for developers at at every level um but it goes back to kind of my my top advice for junior devs which is understand why right like don't just copy paste but understand why the code actually works yeah that was true for stack Overflow you know for the last 10 years and it's true for for AI tools now um in terms of differentiating I really think that it this is going to push developers further toward just understanding product like you need to know what is the intended behavior and then you know if we autocomplete a bunch of

code and that gets better and better that's fantastic but your job is to make sure that it's actually doing what we want it to do and not just what it thinks you want it to do if that that makes sense that makes sense absolutely love that um all right last last few questions um uh kind of Rapid Fire here one [Music] um if you could do something outside of tech money was the same or better let's just say money's not a factor what would you do outside of tech uh I would be running a a small organic farm like so I saw I saw you

post that in the Cy do where do you have a farm now or a small farm or so uh we've got you know we've got our East Nashville house uh with you know a third of an acre and 12 fruit trees in the little gardens we've got mini Orchard here and then we've got about 20 acres a couple hours outside of the city where we're doing kind of a longterm like permaculture project so okay putting in a bunch of fruit and nut trees up there that's cool man that's cool uh second thing is um uh what trying to think here I'm drawing a blank um

bra's not working need more coffee uh I need tools I know I know we talked a little bit about AI stuff but a ny other tools Technologies Frameworks that you're tinkering with right now that you're pretty interested in that you want to share uh yeah definitely been focused on on the AI stuff um yeah in terms of other tools I think I think that's it I'm just trying to stay on top of of all of those and really trying to like automate my business workflows okay it's just hard to keep up right like every every week it's like no that's so last week this is

the new tool so I know to be determined what I use there I love it I love it all right last question here Show's called guidance counsel 2.0 because we had guidance counsels in middle school high school and college but now as adult so we don't really have them per se what would be your biggest piece of career advice to Young readed yeah um I think uh thinking about your skill set a little bit more broadly right it's not just like again it's not are you the best coach in the room and do you know all the languages but like what from your life experience

are you especially good at you know is it just explaining things to people right being able to communicate technical topics to non-technical people like okay that's that can be your thing move in that direction if you you know if you're really good at debugging problems like that is a skill set and actually a really valuable one so find what you're good at not what you think you should be good at not what Hacker News tells you you should be good at but what are you actually like uniquely good at and then just double down on that thing you know and and learn as much as

possible around it um so yeah just be curious learn the why uh and you know do things your own way you don't have to you know have to do things that that they would do at meta like figure out your own thing and have fun doing it I love it man' I love it well re thank you again for hanging out with me today I appreciate for those of you who are watching how can people reach out to you if somebody needs a fractional C TO how can people reach out to you uh yeah R Tomlinson consulting.com unwieldy title but there it is also on

on LinkedIn yeah Reach Out happy to talk cool fantastic well y'all thank you again again send re a DM let them know you en enjoyed the show today connect with people in the D in the DMS on the chat um otherwise tomorrow we have a great week of of of guests Tomorrow Sam Julian he's a former director devil um Planet scale I think um he's coming on the show Wednesday I have my guy who's current devil at OCTA will Johnson who's also going to be MC of react Miami here in a few weeks Thursday unicorn finers have a really cool kind of AI company coming

on that I met at South by Southwest and then we conclude Friday with Gant Gant is the CTO of infinite red a react cons react native consulant company out west so he's coming on we're going to talk about some fun stuff so again y'all have a go and read thank you my friends on so I can say bye to you backstage