#229 Bill Boulden from ideas to product as a fractional CTO

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Bill Boulden 0:00
One of the things I would say is a key experience to sort of working with the startup phase is you need to be comfortable with finishing the job, like starting with nothing. And then being like, Okay, I set up the domain name, I configured the marketing site. It's running, I set up Nginx. I set up the serverless repo, I set up the deploy system. It's running, the site is up now. And that's something that you know, you don't actually get a lot of chances to be the one who does it all. And that's a key thing is to be able to be able to do that whole end to end full stack journey.

Tim Bourguignon 0:41
Hello, and welcome to developer's journey to podcast, bringing you the making of stories of successful software developers to help you on your upcoming journey. I'm your host team building your own this episode 229. I receive Bill Bolden. Bill is a fractional CTO of nine tech startups was launched over a dozen products. He specializes in the zero to one phase, and takes products that are in the ID phase with no tech or working product to the point where the launch to customers. Bill has been involved in all sides of startups, including sales and marketing support, investment and growth. And I'm sure we're going to take about signups. And did I say he I think it's a bill. It's a I'm sorry about that bill, a warm welcome directory.

Bill Boulden 1:31
Thank you so much for having me, Tim.

Tim Bourguignon 1:33
But before we come to your story, I want to thank the terrific listeners who support the show every month, you are keeping the dev journey lights up. If you would like to join this fine crew and help me spend more time on finding phenomenal guests, then editing audio tracks, please go to our website, Dev journey dot info and click on the Support me on Patreon button. Even the smallest contributions are giant steps toward a sustainable dev journey. journey. Thank you. And now back to today's guest. So Bill, as you know, the show exists to help the listeners understand what your story looked like, and imagine how to shape their own future. So as usual on the show, let's go back to your beginnings. Where would you place to start if you're deaf journey,

Bill Boulden 2:23
I would say that I probably have three starts to my dev journey. There's the first one, which was when I was six years old and wrote my first line of code all credit goes to my father for being a big nerd. And owning Ataris and Commodores and Apple two E's and other 80s computing. So, uh, he showed me on the Commodore 64, how I can tell you 10 Billy rules 20, go to 10 and create an infinite loop that would print Billy rules forever. That was the first program I ever wrote, I was six, I was hooked. So the next thing you know, I was working in basic than Visual Basic, then throughout most of my teens, I was, you know, fooling around making like little point and click games, then I would say that the second start to my job journey is when I got my first full time job that wasn't college working tech support, I did do tech support in college, so that that was more time spent expanding my knowledge of computing. But after college, I got my junior developer role at an internet advertising company. And that was probably the real start of my dev journey, because it's where I began understanding how to operate in a business context. Not in a school context, where I believe that in school, you often learn how to play the school game, where it's about completing projects and hitting these milestones and stuff. But in the business world, especially the small business world, it's all about releases, it's all about like, it doesn't matter what you've done, or who wrote which piece of code, it matters, that it's out and customers are using it. And that's where I really began internalizing that. Then I'd say the third start to my deaf career happened in 2020, when I sort of fell into being a fractional CTO, which happened almost entirely by circumstances, but it's defined my life ever since. And it is a new and exciting phase of my career and feels like a fresh start.

Tim Bourguignon 4:35
So let's let's unpack all this and we'll come to the fractional CTO in a minute. Did you do you have the feeling that you always knew you would lend into the computer world?

Bill Boulden 4:45
Yes, I I feel that when I go back and read my diaries from when I was a child. I always wrote that I knew I wanted to be a computer programmer. Now being the young geek I was I really thought I'd be making video games. And I remember one funny entry from one of my diaries that was like, when I am growing up I am going to make video games. I will make them for the Nintendo and the Sega and I will make them for the Atari and the Commodore 64 and Commodore 120 Yes, I can say that that dream did not come to fruition I am not making games for the Atari

Tim Bourguignon 5:25
them but making games at all or is it still a solo somewhere in your in your hobbies?

Bill Boulden 5:31
I have too much of my free time caught up in my EDM production a hobby to really devote much time to doing games. I think that if I wasn't producing EDM, I would probably be making games in my spare time.

Tim Bourguignon 5:45
Okay, but did you try at some point?

Bill Boulden 5:49
I actually have not. I've done Hello worlds. Like I did a Hello World for the Xbox 360. But never got any further than that. Just to say I knew how it's done. But yeah, one of these days, I got to do a Hello World and like Unity or Unreal, so that I can learn the basics of game programming.

Tim Bourguignon 6:07
Yeah, I did my toes in my with my son into unity, and that scratching the itch that was there from from long years past as well. But I must say it's good enough for spending a few a few hours, probably 30 hours or something in unity and really getting to know okay, this is where this goes, this is where that goes. This is how it things and sometimes say okay, now now I discovered enough. And the rest would be work. And so that's fine. fine to leave it to somebody else. So yeah, I had the same dreams, like many, many of us themselves for creating games long time ago, but I'm fine with that now. So during your studies, you say to you, you worked in tech support, and was it again, as something deliberate to stay to stay in the tech world or?

Bill Boulden 6:54
Yeah, it just sort of, I knew that I was going to be I mean, I was going to school for computer science. And I knew that I was going to go into computer science as a field. And so the natural job to seek for part time college employment was a job working tech support, just basic call center stuff, answering calls and using the knowledge base to direct people how to reboot their computers and stuff. But that was actually really good experience for learning a whole host of unrelated minor stuff that pays you back over the course of your life. Like, at no point in a boot camp journey today, is a junior dev gonna learn a deep look at like how Windows printer drivers work. Right? It's not, it's not germane to the things you want to learn in boot camp. But having known all that from 22 years ago, it really pays you back in little ways today, still knowing like, Oh, this is probably a DLL thing, or oh, I've been here before this person clearly is on an old version of Internet Explorer, that old chestnut.

Tim Bourguignon 8:08
That's I like the way you formulated it the host of unrelated minor stuff. Because it's really those minor stuff that you actually experiment when you're troubleshooting your own way. When when you have a minor problem and say, Okay, what could it be? What could it be? Let's go there. Let's go there. Let's go there. Let's go there. Some of those steps, you have to do some of the steps you can even do in your mind and say, well, that cannot be that he cannot be that. And you so are you experienced through those users a whole host of problems that you don't have to have on your own? You can no match them in your mind and say, Well, no, probably not that. That is that is very interesting.

Bill Boulden 8:42
Yes. And another way to look out for it is for your hobbies to also play into that because I mentioned that I'm very into EDM production. I've been a sound engineer my whole life. I have sine saw and square waves tattooed around my arm that actually came in really handy when I was launching one of my products, a podcast hosting platform, so lots of audio, and WAV files and mp3 files. And I was amazed at how often things that I've learned from sound engineering, like gating and compression. And other tools could be applied to my day job. So always be on the lookout for these things you've accumulated like a snowball rolling downhill to pay you back in your day job

Tim Bourguignon 9:29
in the end, so after this, after your college experience, how did you decide on where to start?

Bill Boulden 9:35
I was fresh out of college, it was time to find a job. I applied to three junior positions. And I was qualified and had good grades so I got three offers. I understand there's probably some privilege and luck that went into that as well. So just saying that for a full disclaimer, but I was very lucky to have my choice of three offers and they would have taken me in very different directions. One was for a banking software company working in VB dotnet. One was working for a health care company working in VB dotnet. And one was for an internet advertising startup working in Perl. And that really represented a fork in the road. And I can't imagine how different my life would have been had I chosen either of the former to, I would have started to build all my experience on the dotnet stack doing things on the Microsoft IR side of things. Today, I probably be a certified Azure consultant instead of a certified AWS consultant. But instead, I picked the more open source direction, and it was a smaller company and very internet savvy, a lot less dry than healthcare and banking, which I am led to believe now looking at the job market. If I was in those today, those be very lucrative verticals to be in. But at the same time, it's hard to get excited or have have a big laugh at work, which was like not true when I went on to work for a social media startup, where every day was like a party. Well, that's where my that's where my paths diverged after college. And I chose the more open source one.

Tim Bourguignon 11:26
Is it a qualifier that you put in retrospect, or was it in your mind or on your mind back then really seeing Okay, I have this fork on the road and I can go toward open source or I can go toward more traditional or established banking and healthcare industries.

Bill Boulden 12:32
Actually, at the time, the biggest, the biggest fork in the road I saw was between a fun dynamic startup and sort of stodgy like. Remember, this was about 20, full years ago. So like dress codes, were still a thing. And I was literally being faced with a choice between like, do I want to wear a tie every day to work? Or do I want the kind of place that you can show up? Be yourself chum around some pizza. And this was way back when Google and everything still had very positive effects on the developer culture. Today, you know, you hear a lot of people and a lot of press saying they're starting to have more negative effects on the developer culture. But at the time, the whole Silicon Valley ethos was like, get you one of these jobs get you one of these stand ups over a pizza party kind of jobs. And so that's what really led me in that direction. The open source was a bonus.

Tim Bourguignon 13:30
Okay, so So you chose that one. And this is what defined you being into the startup world ever since?

Bill Boulden 13:38
Yes, with one brief interruption for about 10 months. I've worked exclusively at startups ever since then. And the brief interruption was the company failed after seven years of me being there, because all internet advertising companies were falling before the might that was Google and their acquisition of double click, and there wasn't much room left. For smaller players, you just couldn't get the margins. So I went to a big corporate role and an 80,000 person company after the internet advertising company, but I lasted about 10 months before I was like, This is not my scene. I'm spending all day working on the most minut things in the most minut systems. I feel so distant and removed from my work that I fell back into a startup and really taking the plunge all the way back down to zero to one because I left that job for a pie in the sky founder came was like I'm looking for my first engineer someone to build this from scratch. I was like, Yes, I will be that person.

Tim Bourguignon 14:49
Wow. Okay. Did you feel you feel ready to tackle such a such a challenge being the first engineering in a tech startup?

Bill Boulden 14:57
Yes, at that point, I was about eight years. into my career and I knew enough to launch a product. I didn't know about a lot of the common pitfalls and mistakes. face while you're on that path, but I knew enough to get it off the ground.

Tim Bourguignon 15:12
Okay, so that was did you do you describe this as your first CTO role or not? Yeah, yeah. Okay.

Bill Boulden 15:18
Yeah, this was my first CTO role, but full time, not fractional.

Tim Bourguignon 15:22
Okay, maybe it's time now to define what fractional CTO is.

Bill Boulden 15:27
So a fractional CTO is kind of undefined position that everyone does a little differently. There are only a few people calling themselves fractional CTOs. And that means something different to everyone else. What it means for me is that I seek out this market segment of non technical founders who have ideas they would like to bring to market, but they really just don't know anything about the tech. And they imagined that there are some tech wizard person who knows all the rest, there's how to get an app in the store how a database works, all the things they don't know, they're like, someone will deal with this. I'm that someone. But these small time founders often don't have what it takes to pay a Silicon Valley tier CTO salary. And they may have raised $50,000, they may have raised $100,000, from a pitch competition and their own savings. And so I come in at a price point where you can get me not full time, but just for the needful just to do what needs doing one to two hours a day, and at a much more affordable rate that fits into your budget. And I'll stick with you until the product launches.

Tim Bourguignon 16:41
So that means probably working alongside other engineers and really advising showing the right way to avoid the pitfalls you mentioned. And but letting somebody else do the bulk of the job, and you bringing additional value,

Bill Boulden 16:55
yes, I supervise the release of the product, I know how all the tech should work. I know all the ingredients to getting it out there. And I have a very laser like focus on getting the job done. You know, I never one of my roles is the role of bearing responsibility. So I'll come in, I'll hire two juniors to seniors, will will make a team out of it. I'll direct and run the team with stand ups, agile retros click ups or JIRAs or Mondays or notions or whichever thing you're using shepherd them up through launch, and then stick around as an advisor afterward, having built a functional team, that now the customer owns and can carry them forward.

Tim Bourguignon 17:41
So it's really the this all encompassing role, not just the tech role. That's really the take organization role, it can go all the way to choosing the right or the right size to build on the right tools to have on your end how people collaborate, etc. And all the way to shepherding probably the product discovery side, and really what we should be building.

Bill Boulden 18:03
That's exactly it. Because I work with such small teams, you know, when you're in a team of the whole company is for people. There's no room for anyone to say, that's not my job. I don't I don't ever say like, oh, that's not literally about a line of code, therefore, I don't know. So I've been a part of building help desks and support channels, building out sales funnels, running corporate social media, hiring and firing, corporate culture. I've just been at so many different startups. I've been at, like 12 startups, that I've seen it all already. And so when someone hires Bill Bolden, I don't stay in my lane and say only talk to me, if it's about code. I will speak up and say, Hey, six startups ago, a company I did have this policy and it wasn't good for company culture. Let's not repeat that mistake.

Tim Bourguignon 19:04
Is the description CTO accurate, or it's more of a trump card in your sleeve, doing whatever is needed to move the business for

Bill Boulden 19:12
it. Really, it's all about being whatever the business needs me to be with a focus on. I know a lot about development. I can manage developers, I can unblock developers, I can mentor and teach developers. So it's all very development focused. But if one of these companies is trying to implement a new sales funnel or a new Help Desk solution, I'll also be there with those lessons learned.

Tim Bourguignon 19:38
How do you pick and choose which startups you want to work with?

Bill Boulden 19:43
Well, I'm lucky to have a strong funnel mostly coming from referrals. But my golden rule is that the startup needs to be ethically neutral or better. So one thing I always tell the people I'm going to work with is now that This is an opinionated thing. So here come opinions, life is too short to work on weapons that drop bombs, you can't spend your one life writing code that helps blow things up. And so if something is related to like greenhouse gases, or polluting, or the defense industry, or detaining people or the prison industry or anything, I want no part of it. So my rule when someone comes to me with an idea is that it needs to be from an ethical and more moral standpoint. It needs to make the world a better place, or it needs to at least be indifferent. Like it's making the world not a worse place in any sense. And you'd be surprised how many companies that disqualifies because a lot of the modern era is unsavory. Lots of very big companies are about taking people's wealth away or fooling consumers and life's too short.

Tim Bourguignon 21:01
Indeed. That's a very loaded question to ask, how did that relate to the first experience you had in in the click industry on the advertising industry?

Bill Boulden 21:12
That is a big part of why I have this policy. Now, I had a lifetime supply of bad karma from working in the internet advertising industry, I was at that company for a while I felt at the time, like I was just doing my job and showing up to work to write code each day. But towards the end, especially as the company started to fail, it began to overly rely on a few bad advertisers. So you know, when you when you were on the sales calls, being real honest here, because I hate talking about this. But when you were on the sales calls, you would show examples where the banner ad was like, Progressive Insurance and stuff. But in practice, the people who were winning the bids, were these like weight loss, scam people and stuff. And towards the end, I started feeling real achy, like how could I wake up with myself each morning knowing I was part of that. And so after that company folded, I said, Never again, I can't feel that way. Again, I'm not going to work on anything unsavory like that. That leaves you with that icky feeling.

Tim Bourguignon 22:18
I totally agree, it leads back to a drive from Daniel Pink, the purpose really has a big impact on motivation. And if it's not there, then you can forget it provided a company is ethically ethically a contributor, how you put it neutral or positive what's what's your next decision point or metric to say, Okay, this is a company I want to work with.

Bill Boulden 22:42
Well, I have a couple, a couple of rules of things that I've done already, and so don't want to do it again. Which is interesting, because you think in a lot of cases, having done something means that you should be well equipped to do it again. But for me, life is a collection of rich experiences and learning and product building experience. And so I already built one marketplace app. You know, an app that connects people who want to rent out their blank with people who want to rent a blank. And there's so many of these. There's Airbnb, there's Uber, there's DoorDash there's Turo, there's Instacart. They're all connecting people who will perform some service with people who need the service. I did one of those for commercial kitchens, that company is doing quite well. You can you can log on to the site. And you can say, I need a place to bake 400 Muffins on Saturday for one day. And you can find a kitchen you can rent cool stuff. Since then, I've been pitched a number of Marketplace apps for different ideas like a site where people who need a certain errand performed can find people who perform that errand. And I turned those down because I've already been there and learned everything there is to learn about that industry. Okay.

Tim Bourguignon 24:02
Okay, so So nudity.

Bill Boulden 24:04
Is that a word? Nudity? Yeah.

Tim Bourguignon 24:08
Nobody? Yeah, thank you. Well, what used to be piece of it, okay.

Bill Boulden 24:11
Yeah. Another one is I spent about four years with a company that was a social media startup. And I just had my fill of working with Facebook and LinkedIn and Twitter API's. And I've, I learned all there was, well, I shouldn't ever say all there was to know of course, I'll never learn all there is to know, but I had a lifetime supply of sharing content, Twitter, and Facebook. And now I'm not even so sure that social media is a good thing for the world doesn't pass the first bar of you particularly doesn't pass the first bar. After all that's left assuming the company's ethically positive and I get a good vibe from the founder if the financials can work out and I can come in at a price point where what I can give is what they need. Then I'm I'm interested said that's how I'm working with nine companies right now.

Tim Bourguignon 25:03
In parallel.

Bill Boulden 25:06
Yes, although I, I spaced them out, so the only one is hot at any given time. So the way it works when when you do, what I do is there's a hot phase of about two months, where you start, you learn everything you can about the industry and the vertical, you put together a team, you're hiring, you're firing, you're interviewing, you're spinning up the DevOps, you're making the infrastructure and the architecture that's going to serve the Hello World, you're writing those first few lines of business code, you're like practically full time for these first two months. And then if you've done your job, right, the engineers will start to know what to do without you, the processes you've put in place will start kicking in, things just work like a like a flywheel running on its own. And so you, you fade away into the background to about an hour a day's worth of being in Slack and having meetings and mentoring junior, and it's all about board, everybody knows that like this is the fade out portion. And then at some point, after successful launch, and after the product is doing well transition into being an advisor, rather than on the payroll.

Tim Bourguignon 26:26
Okay, so one one contract is hot and taking you the bulk of your day, then one or two are in the phase out phase one, one, definitely, maybe your second one is still in the in the phase in the phase out. And then the other ones are pretty much pool from the from the customers when they have a question or when they have something, then they come to you. And you try to to to squeeze that in.

Bill Boulden 26:47
Yes. Okay, that's a perfect proximation of how I work, that's what my day to day is like. Good? Well, it really keeps an interesting mix of things like one minute, I'm, hey, my developer has a merge conflict and doesn't know how to resolve it. In the meanwhile, I'm also getting messages from another client, a customer wrote into support with an interesting issue, their podcast isn't appearing. And I'm like, and so I'm switching back to that code base and thinking about that, at the same time, I'm doing an interview for a new position, and writing a product spec for something we're about to build. So it's really a healthy diet of keeping things fresh all day, I wouldn't trade this at all, for any kind of job that was like eight hours spent doing the same thing every day. It's so nice to have so much variety.

Tim Bourguignon 27:44
How do you do you ensure that it doesn't become too much context switching a bit of context switching is good, but it doesn't become too much.

Bill Boulden 27:53
The context switching is the worst part of it, the context switching is challenging. And that is the big reason why I have my one client at a time rule. So I never really context switch away from the hot client for very long, there was a time when I had like two hot clients at once. And that was I couldn't track it. It's the one hot client at a time rule really helps keep context switching to a minimum.

Tim Bourguignon 28:19
And how do you fight with with probably your your subjective or subconscious wanting to continue on a subject, say, hey, that is so interesting, I would like to continue but but this customer is rolling on their own and and they have to do it or maybe when they come back and say Hey, could you help us with this? And this and that? Isn't that that's No, you're not hot anymore?

Bill Boulden 28:41
Yeah, and I don't use that language with the customer. I phased out this is something for Jerry to do. We have, you know, I hired and trained Jerry to be able to do this. So I need you to keep this with Jerry. If Jerry remains blocked for like an hour or more, he can call me in but I have to run the meter. Okay, so that's always the like, the final step is on the last escalation on the ladder. Because I'm, I'm admittedly a very good developer with 20 years of experience and so I can fix most of the problems that come up. But I need the, the devs at these companies to try to learn and self better and educate themselves. Then I'm the last, the last rung on the ladder. But then I have to run the meter, which you know, is always for some of these companies. Some of them I've been silently helping them for months without having to run the meter. You know, I just kind of watch everything in Slack and nod and say this is good. The team is running itself.

Tim Bourguignon 29:50
Are you so you're keep you keep an eye on what's happening in Slack and keep an eye on the on the the noise around the development.

Bill Boulden 29:59
Yep, I keep an eye on the water cooler chat and speak up if I see something going astray.

Tim Bourguignon 30:06
And that oh nine projects at the same time.

Bill Boulden 30:10
Yeah, right now I'm in 24 slacks. slack on my computer is 24 slacks.

Tim Bourguignon 30:19
Ouch, you know that there's just too much? How do you handle that

Bill Boulden 30:25
judicious muting of some channels. But not the one. Not the watercooler. But the automated channel, that channel where like so and so pushed to GitHub comes in. Oh, I only need to know if it's the hot client. Okay, first for the cold clients. So you can push to GitHub all you want. I'm not getting notified.

Tim Bourguignon 30:45
But you still have 24 hours a day, right? You don't have a secret to have more?

Bill Boulden 30:51
No, I still only have 24 hours in a day. Yeah.

Tim Bourguignon 30:55
And at the same time, you must be looking for clients, or looking for your next gig.

Bill Boulden 31:00
Yes, I always am. And I know it might sound imposing like do I really want to be this person's 10th startup. But um, the way the hot client cold client system works, anyone is eligible to be the next hot client, if you or someone you know, is a non technical founder, who doesn't really know how a product gets built, and wants a product built, you know, reach out to me, I'm available.

Tim Bourguignon 31:26
How long do you need for or do you usually need for for spinning up such an such such product?

Bill Boulden 31:32
Usually, the last couple projects, we've hit prod within six to eight weeks. But that's because I aggressively define MVP downward, which is something I'm very passionate about, which is whatever you think your MVP is, shave three or four features off of it, than talk to me, right? You know, your first MVP is the first thing that does the thing. That isn't embarrassing. So as soon as you've got a thing that does even the one thing, and it's not embarrassing, it's go time. I can get to that point in six to eight weeks.

Tim Bourguignon 32:11
Okay, so that means you're pushing back on some of your potential clients say, well review a copy and come back in a couple of weeks a month, I will help

Bill Boulden 32:18
them with that process, I will lay out a roadmap for like after release. So this thing that they think they have to have like, oh, what's an example, it has to integrate with Salesforce? No, it doesn't not in step one, unless it's a Salesforce plugin, in which case that's native to what it is. But if you're building a standalone software, let's get your software that does the task out, then phase two is the Salesforce integration.

Tim Bourguignon 32:46
Okay, and how's your relationship with with the so called no code industry side, which could be helping as well to shave off some some, some some weeks of developments to test an idea and get one foot out the door,

Bill Boulden 33:00
I'm very into it, I encourage my clients to build their MVP using a no code solution. If at all, I will always advise my people to set up a web flow site that's hooked up to a type form that you manually do the results of. So a good example is I had a client who wanted to make a marketplace where there was a certain obnoxious errand that he hated running. And he wanted an app where you could summon people to do the errand for you. And I told them this, to pilot this to figure out if you if anyone is interested in this, you're just going to make a web flow site that hooks up to a type form where people fill out where they need the errand run. And then after they submit, you're gonna collect payment using Stripe, but another great no code tool, and then you're gonna go run that errand, yourself, you're just going to do it on your own until you're like, Okay, I'm doing 15 of these a day, it's time to build the app for real, then I'll build your app. But you know, I knew or at least suspected that it was not going to go anywhere, because he did not actually want to run the errand himself. And so he was like, Well, I'm not going to do that. I want to never run this errand again, I want other people to do it for me. And I'm like, if you can't bring yourself to launch a business by being the one who does this. Why do you think other people will be willing to be gig economy workers to be the ones who do this?

Tim Bourguignon 34:47
Or that's hard push back against an idea

Bill Boulden 34:49
that that was a hard push back. But that was my advice to that particular client.

Tim Bourguignon 34:54
And so you would, in such a case, help this person if he if he was to say yes, I'll do that to him. have him set up a web flow type form, Stripe,

Bill Boulden 35:02
type forum stripe, and it dumps it all into an air table. And then you go and and run the errand yourself.

Tim Bourguignon 35:10
So that's a matter of early hours of hooking things up together. Once you have done it a couple times, it's, it's pretty easy. And that will be on the clock. And then I took a test that for a few weeks, and we'll talk in a few weeks when you have some results.

Bill Boulden 35:24
Yep. And it's if the person comes back and says, Nobody ever used that I ran a Facebook ad campaign and no one filled out the form, I would say, well, then what would be different if you had invested 100 grand into an app?

Tim Bourguignon 35:36
Yeah, sure. Sure. That's, that's interesting. And so if they were to come back, when would you say okay, this this no code approach is is not viable anymore. Or it can be improved and unbuildable? All we have to do it's from scratch again, what would be the heuristic there?

Bill Boulden 35:54
The heuristic there, that's a great question is twofold. First, either there's an opportunity for a lot more revenue. So like, let's say that the idea you have for your app is automatically matching people who need the errand run, and it uses AI to like, generate things. Well, in that case, you sort of have to build the AI for it to happen. So there's an opportunity where you're going to unlock a ton of revenue, if you do the thing for real. The other is that doing it the old school way, the no code way is is broke, you are crumbling under so much demand that you can no longer afford to send these emails one at a time, you can no longer afford to go run that errand yourself. There's too much to do.

Tim Bourguignon 36:44
Okay, so it's very much the the process is broken in itself, it can scale in itself, then then you would consider a rewrite or giving it for real, as you said, Oh, that if it's if it's doing the job, still with no coding tools. Let's let's keep it there.

Bill Boulden 36:59
Yeah, I, one of the biggest ones that I see that can be easily accomplished by no code, is a lot of people come to me wanting to make communities. So like an app for people to meet other people who are passionate about rocks and share their, their rock collections and plan excursions together. And I'm thinking off the top of my head, we'll call it pebble. And that's where I've traditionally found that I tell them, what I'd like to do is I'd like to see if you could grow a discord to 1000 people, or a subreddit to 1000 people. Show me that you have what it takes to build a community on an existing platform where all these people come together. And you have 1000 people with a network effect. Because if you can't do that, then when it's a custom app, why would people sign up for it? If they don't want to be part of that community? And then what I find a lot of the time is that by making a professional slack, or a custom discord, or a custom subreddit, they're happy. They're usually like, oh, this Discord is great. It's everything I wanted.

Tim Bourguignon 38:16
How many customers do you push back on versus the nine that you have? Currently?

Bill Boulden 38:22
I would say I push back gently, gently on 50% of the people who come to me, okay. I usually just tell them that they're the number one thing I deal with is people whose need for a product is premature. They have a finished app idea in their head. And in their heart. It's already the next Airbnb. But I have to tell them, that they are skipping a few steps. They're skipping the important step where they validate their idea works before they sink six figures into it, then we talk, you know, and so that's, it's not as big a pushback. It's just me saying, you're not there yet. I need you to come back when you've got a warm List of 200 users who are ready to go.

Tim Bourguignon 39:10
I see. I think we've been talking a lot of non technical founders. But there is also also half technical founders or technical founders who don't trust themselves. So how do you how do you place yourself on the scale on the note black and white scale?

Bill Boulden 39:22
That's a good question. I feel that I am a fairly. One of the ways I describe myself if fractional CTO doesn't seem to be doing the job is technical co founder for hire. Like I will essentially act as a technical co founder. But when I work with other founders, I have the best luck working with non technical ones simply because what one experience I've had is I've gotten on with technical founders before and they're already really strong and they know the things I know. I've gotten on the phone with people who think they want to hire me And they already know how to bring a product to production. They've got their favorite stack, they've got it all spun out, they've got the prototype built, they're looking for someone to shore up their weak spots, which might be in sales and marketing, or business development. And you know, I have, I can do those things, but I have no particular strength or genius in that zone. So I say I'm not the person.

Tim Bourguignon 40:24
Okay, you mentioned us being a technical co founder or something like a technical co founder, do you mean you change also the kind of revenue streams you have with wisdom, maybe some some options, or some some parts of the company in lieu of salary and stuff like that.

Bill Boulden 40:41
It's different for every client, depending I have clients for whom equity is jealously guarded, and cash is cheap. And I have clients for whom cash is at a premium. But equity is loose, and sure you can have X percent of the company, I do what's right for the client,

Tim Bourguignon 41:01
it makes a lot of sense. That's really cool. So if somebody let's twist that a little bit, if somebody came to you for an advisor and say, Well, I want to be fractional CTO now, what would you tell them?

Bill Boulden 41:14
I would tell them don't start. And actually, I get this question a lot. I've been asked it just twice in the in the last two weeks by other videos who want to move into being fractional, and I'll tell you exactly what I tell them. Don't think that you need to get for clients at 25% of your time. And then you can move into it, you're never going to get the stars to align so that you have all the people to go live at once instead, look like you're looking for a full time job. But don't do a full time engagement with them, do a Hot Zone engagement that tapers off and then continue looking for a new job while you're doing that first one. And it's like you're working full time at first. But then you'll find a second gig to come in and be hot zone after the first one cools. And in that way you'll grow into a system like the one I have today.

Tim Bourguignon 42:09
That that is as awesome as it was not what I was expecting. I thought you would be going into the kind of experiences that you have to have had before in order to start stepping into this direction. When interesting. Again,

Bill Boulden 42:29
in that case, my answer would be more like it really helps to finish the job a few times. There's, there's a lot of developing you can do especially at bigger companies. And I have this problem sometimes with people I hire who are from bigger companies, where everything is taken care of by someone else. The code repo is taken care of by the DevOps person, the deploy is taken care of by the infrastructure team, you're not the one managing the Kubernetes. You're just writing the code. And then what happens happens after change management. And I feel that that stuff can really insulate you from the sense of like being there, when you hit refresh on prod. And there's your code working. And one of the things I would say is a key experience to sort of working with the startup phase, is you need to be comfortable with finishing the job like starting with nothing. And then being like, Okay, I set up the domain name, I configured the marketing site, it's running, I set up nginx, I set up the serverless repo, I set up the deploy system, it's running the site is up now. And that's something that you know, you don't actually get a lot of chances to be the one who does it all. And that's a key thing is to be able to be able to do that whole end to end full stack journey.

Tim Bourguignon 44:01
You have to have owned it a couple times really end to end. And to be really confident you can do it. Obviously there will be some some some some dark spots that you haven't done before. That's part of the job. Then you can hurt yourself into having a first line and then the second one and then second one innovating one interesting system. Bill, it's been a blast, I discovered a whole new world I didn't suspect existed. That's very cool.

Bill Boulden 44:29
Thank you so much. It's been a pleasure being here, Tim.

Tim Bourguignon 44:32
Fantastic. Where would be the best place to continue this discussion and maybe talk to you about product idea that we have?

Bill Boulden 44:40
Sure you can find me on LinkedIn at linkedin.com/in/bill Bolden, b i ll Bo ULDN. On Twitter. I'm actually more there as a DJ and EDM producer than I am as a AWS engineer but on Twitter I'm down, up, right?

Tim Bourguignon 45:02
And we'll add those to to the shownotes. Don't have to remember them. Just scroll down there and click on it.

Bill Boulden 45:09
You just get Yeah, I have a site. It's Bill bolden.com.

Tim Bourguignon 45:14
And we'll add that one as well. Obviously. Fantastic. Anything else on your plate? You want to advertise a plugin before we call it today?

Bill Boulden 45:20
Not at the present time. This has just been wonderful. Tim, thank you so much for having me.

Tim Bourguignon 45:24
And thank you as well. And this has been another episode of developer's journey. I will see each other next week. Bye bye. Thanks a lot for tuning in. I hope you have enjoyed this week's episode. If you liked the show, please share rate and review. It helps more listeners discover those stories. You can find the links to all the platforms to show appears on our website, Dev journey dot info, slash subscribe. Creating the show every week takes a lot of time, energy, and of course money. Will you please help me continue bringing out those inspiring stories every week by pledging a small monthly donation, you'll find our patreon link at Dev journey dot info slash donate. And finally don't hesitate to reach out and tell me how this week story is shaping your future. You can find me on Twitter at @timothep ti m o th e p or email info at Dev journey dot info. Talk to you soon.