It Won't Be a Straight Line: A Founder's Journey Starting, Growing & Selling a SaaS – Garrett Dimon

0:00[Music] [Applause] okay so a real quick question for everybody who here has had everything in their life go perfect like according to plan nothing's ever gone wrong at all okay seems right so I've had a lot happen to me in the last five years and I've learned quite a few lessons really really really good lessons like so good they normally would cost an arm and a leg clearly I got them half-price and I've gotten even better discount for y'all today because it's free so I'm at Garrett diamond and I've had a lot happen to me in the last five years a whole lot both business health

0:59everything and the business my leg these are things that were very deeply important to me part of my identity the business more so than the leg but well hang on before I get too deep there's I know everybody's got this one question it's just weighing on their mind and we need to get the elephant out of the room I briefly considered working at IHOP it would have been very own brand just slightly less lucrative and so I went ahead and went in a different direction I think I'll probably stick with software so for a little context this has been going on to me for about five

1:39years it's been about a year two years going on two years since I actually amputated and I've had a whole bunch of crap happened to me and lost a whole bunch of time and productivity to appointments just being tired exhausted worn out in bed and it was rough thankfully after having gone through all of this like these days there's really only one thing that I get anxious or worried about anymore that I stress out about and I have to be very very very very careful when I'm talking to people I have to enunciate very clearly when I tell them I'm going to see my prosthetist so all of that adds up to

2:21about a hundred and twenty days lost or you know that's roughly losing your vacation for five years straight that's about six point eight percent of the last five years of my life or who here would like to just sleep about an hour and a half less every night for five years straight so that's kind of what I've been through high at a high level at the same time so a little bit about me I've been fascinated by software software development the process of creating software shipping software just all the aspects of it the logistics of it and there's a joke I like to tell that I

2:59think really summarizes shipping software there's ten engineers to go to a class they work for an avionics company so they make software for airplanes and they're going to a class to train to be managers and the teacher rolls in and says all right here's how we're gonna start the class I've got one question for you you're going on a business trip and you notice as you're getting on the airplane a plaque that shows your team wrote the software that powers this airplane how many of you would get off the airplane nine hands shot up right so the tenth the teachers come you know this is a loaded question

3:39you're supposed to raise your hand why'd you raise your hand oh this is really simple my team wrote the software the powered is this airplane it's not getting off the ground so I think all software teams are dysfunctional in their own way not in a purely bad sense but I think there's ways there's always ways to improve and optimize and even if you get settled into a good path you team grows and you've got to adjust at a time when I started sifter this was in 2008 I felt like small teams I wanted to make bug tracking more approachable to small teams more accessible and so I launched

4:18sifter because the world did need yet another bug tracker in and of itself sifter really isn't a super fancy case study or really anything drastic to learn from but the crossroads of sifter dealing with my leg the health issues and ultimately selling it really really taught me a lot so that's kind of what we're gonna talk about the intersection of all of that I no longer work at sifter obviously I sold that nowadays I work at wild a bit if you're not familiar with wild a bit you may be familiar with some of our products working for wild a bit was one of the best decisions I've made through all

4:59this and it's a lot of that has to do with wild a bit just being well but it's a really great company but a lot of it has to do with accepting that I didn't have to be my own boss for the rest of my life I'm a again some day I feel like sometimes we get caught up thinking that that's the only way we have to do things and it's good but it's not always the right way so sometimes it's okay to let go in addition to that through all of this knowledge I've been in the SAS world for a long time been doing a lot

5:30of software stuff I wrote a book about that I wrote it about four years ago and then going through all of this I realized how wholly inadequate was I needed to update it it's since then gone from 36,000 words to almost a hundred thousand words and a whole bunch of other resources the good news is the book is done it's online you can read it today for free just go to the website starting in sustaining calm there's a spreadsheet that's also free can really help you wrap your head around the financials it's just a Google sheet you duplicate it customize it for your go to town and helps you get a good idea

6:04of what you're looking at financially oh the timer didn't start so I'm afraid I may I'll just wing it but run over it's not my fault and I'm hopefully gonna finish it up it's gonna be an audio book Kindle all that stuff here pretty soon but it just shares all of that wisdom ah perfect so how did this all happen to me my leg I played a lot of basketball had a lot of ankle sprains I was getting older Needham Idol ain't minor ankle surgery they sent me home with one of these it's a nice machine so you keep swelling down I went in for a check-up a couple days

6:46after the surgery and I had frostbite thankfully I was able to keep my cool and which is one of the things people ask me a lot is how have you managed to stay so positive through everything you've been through and all of this you've dealt with and you know in a way I feel guilty because I have kind of this superpower I literally cannot help but get out of bed every day on the right foot sorry long story short really it comes down to when things suck you just got to keep going you got to keep trudging through it and there's a story with sifter and

7:30this happened probably about year three I wasn't quite full-time but it was borderline it was getting there I was right on the cuff was gonna make it I was in a hurry I wanted to you do I was doing an upgrade I wanted to tell us like five minutes of downtime is better than thirty minutes of downtime but I had to make the decision quick I'll spare the back backstory I made the wrong decision and I knew after I deleted eight hours of customer data this is what I was going to see the next morning and it's like well this is it I was about to go

8:05full time on sifter probably the next six months and now I need to look for a job but before I did that and totally gave up I stopped and thought you know what if I had nothing to lose let's see if I can salvage a situation managed to restore about five of those eight hours from backup data and was in alright alright shape it cost us about $700 in customer credits the customers were beyond understanding like nobody was even mad it was crazy and I survived sifter survived and in a lot of ways there's all these bad things that happen in life in business especially in

8:41business you're gonna make mistakes a lot of them hopefully nowhere near as big as I made hopefully almost frivolous but it's just not worth worrying about the fallout it's worth worrying about what you can control and with anything it's best to just do it and do I have to pay Nike for that I think you want to just get started if there's a problem break it down into its parts figure out what you can handle and attack it if it's starting like don't worry about the ideas start hacking on something have fun follow your passion the ideas will spin off these days serverless is the hot new

9:22thing I'm suggesting we go codeless right see what you can build without writing any code all of these tools are incredible right they let you do amazing amazing things without anything and that exploration can open up a lot of ideas and it can help expose your mind to just what you're trying to attack what you're trying to tackle how big it is how small it is and even better chances are pretty good you can build something that will justify people giving you money with just these tools or these kinds of tools we look for inspiration we want it to just come to us but it doesn't happen

10:01inspiration comes from doing the work and letting things happen to you and then noticing things connecting the dots

10:12we're talking a lot about validating ideas you want to kind of test things out you don't want to go too far but you need to go far enough and it's difficult there's no two ways about it there's no simple perfect answer you want to approach everything with babies one little step at a time like Rob stair-step approach you don't want to just go all in a good story from this with my doctor's not my doctor's cuz it was brief when I first figured out my foot starts slowing out and it hurts like hell I go to the ER finally and you know it's hurting it's hurting and so

10:51they give me a shot of morphine and I swore it was a placebo and I didn't feel anything I'm like this is ridiculous I need more come on and they're like we need to wait 15 minutes they didn't just you know give me a glass of morphine or something and so they give me another shot that didn't do anything either I'm just in miserable miserable pain so finally I convinced them to give me a third shot and that one was successful

11:28hang on wait for it you can thank my wife for having the presence of mind to be so concerned about me that she pulled out her phone to video me you don't always know if something's gonna work you want to kind of try something and it's tough you've got to try just enough that it's worth and you're actually in or in something but you don't want to go so far in that you waste a bunch of resources and that's gonna be the case forever with building a business no matter how big it gets every idea it's a tough line to walk with skidding started I think there's a lot of ways if it's

12:08software you can take a different approach there's there's always something bite-sized you can take away from it extract and start there with that little core bit of an idea and then expand it then start making it more complex one step at a time the nice thing is by doing this you don't start thinking about taking money until version three there you start thinking about taking money at version one it's just a lot more of a pain in the ass to take the money because you have to process it manually or send an invoice or something like that when you have to ask people to give you money it forces

12:43you to clear out all the BS you can't dance around and ignore things you really have to create something and justify what you're asking them to give you money for as software developers or makers or anything we probably don't enjoy sales sales isn't fun there are people who you can tell they just are energized by talking to people in doing sales so what I suggest think about sales as research right your website is selling every day but when people leave they're telling you no but not why they're telling you know if you're on a phone call with someone and they say no they're gonna explain to you why what

13:22that objection is that gives you the material to understand what you're doing wrong you can understand their pains a little better think of sales as research not as sales and approach it as research how can I help you and it's the same thing when you really really break it down it turns into this thing so getting back to my leg we needed a version one solution what were we gonna do in my case we tried a skin graft and I spent a lot of time in a hyperbaric chamber which is just full of oxygen trying to stimulate growth it didn't go well I mean it didn't go bad it's just it

13:59didn't get the job done but this is the first point where I'm really spending a ton of time being and just not being productive not working on sifter not getting things done when I'm not in a hyperbaric chamber I'm at home on narcotics in pain tired groggy is about this time I certainly I'm like damn it's like I barely worked on sifter in the last at this point I don't I was probably my part of me is like worrying oh crap my customers are all gonna cancel and leave and oh this is just terrible but then I realized and it clicked with me we worry about health a lot as entrepreneurs like

14:39you know in the US and some other countries are luckier and it's a problem we worry about it but once a business is established sifter was my health insurance I was still getting paid I even got a raise over the course of the years that I was working on sifter less and less because it was still growing and it was still doing well there's some reframing I think we can all do in that we want to have some control over our lives but you don't realize how powerful recurring revenue or you know even info products you can still sell an info products while you're laid up in bed

15:12injured hurt it may take a little more work but there's a lot of safety and recurring revenue for you for your family and I think it's just as important to consider that as it is to consider it while it's scary to not have corporate health insurance so like I said this is the skin graft stuff didn't go super well we decided we probably need to pivot here we need to get a little more ambitious and so it's about this time I want to do some negative visualization say what's the worst thing that can happen so I went and read a book about Scott Rigsby who was the

15:46first bilateral amputee to finish not win but finish via Hawaii Ironman Triathlon I don't know how many people in here thought about running a triathlon I sure haven't I don't how many people in here would lose their legs and then think about running a triathlon but he did I was like well damn I was like okay I'm not gonna amputate she's not gonna be fun it's not something I would look forward to but I don't need to be scared of it anymore it's important that we maintain perspective both in life and with business a lot of times you'll hear people say oh well it could be worse

16:20that is it's such a useless useless phrase of course it could be worse it could also be better it's not about that it's about being able to handle things and we all think oh I could never handle that I couldn't do that the thing is you can you just haven't had to yet fortunately in business you're gonna have to handle it things are gonna go wrong your business will plateau you may have to hire fire or whatever it is you can handle it you're not gonna enjoy it it's not really gonna be fun but you can handle it I promise so version 2.0 the scene graph didn't

16:55work we need to make some progress it's easy at this point - theoretically I could have been pretty defeated and say oh I'm not doing well this this kind of stinks but progress is progress you're not gonna make a big splash every single day right where you're chipping away at something and making long-term progress I think Patrick did a really good job talking about that this morning steps are still steps just keep moving forward in my case the next step was what they call a free flap if a skin graft is the equivalent of taking some skin like bacon and laying bacon over your skin a free flap is where they take

17:36a chunk of your body and move it to another area so I had a free flap it's supposed to be an eight-hour surgery it turned into ten I'm supposed to an ICU for a week I ended up in much longer so the first free flap the doctor he comes in and he's looking he's like oh you know the words you don't want to hear that's not good make it's better and so I was like okay how doc are we throwing good money too bad here he's like yeah we can do another one I'm like wait wait like should we consider amputation and he says don't worry and now you might think

18:15he said don't worry it'll be fine this time but no he says don't worry you have plenty of places from which I can take another flap how many times are you willing to do this doc the thing was like we had done enough research at that point we'd seen enough doctors talked to enough people we knew he was the person for the job there was no doubt in my mind and I think we do this enough to some degree and our personalized we're a little more willing to delegate and trust professionals with things that aren't fully in our wheelhouse with business though we think I can learn

18:47that I can do that and so we do it instead of hiring a professional which you know there's the old saying you know if you think a professional is expensive try hiring an amateur but that's what we do all the time to ourselves and on top of that not only are we doing not as good of a job as we could write but what we're wasting our time our expertise that we should be focusing on and so you can't always afford to hire an expert right out of the gate but as soon as you can delegate dump work on other people have people who are more talented than

19:21you in a certain area do that work don't try to do it all yourself you have things you're good at focus on those things go really really grind away on those things and when you delegate the first attempts are not going to go well maybe the first ten attempts they're not gonna go well don't give up keep trying delegation is a learned skill it's not something that you just magically get good at by telling somebody you want them to do some work that was a really big lesson that was very difficult for me to learn and accept so version 2.1 that second flap here we go again

19:53some in ICU and if you've never been in ICU it is not a fun place it is rather miserable there's wires running everywhere you can't move there's things beeping but they give you a magical button a very very magical button in most cases this button makes you feel better the problem is so most people have a resting heart rate of about 60 beats per minute and they have alarms because monitor their monitoring you and wired up and so if your heart rate drops below 40 beats per minute that's a bad thing and they need to run in and make sure you're okay my resting heart rate

20:29presumably from basketball I don't know turns out it's like 42 and the alarm goes off at 40 and I don't know if anybody's familiar with how narcotics work they lower your heart rate and then when you fall asleep it goes down a little bit more so effectively when I went to sleep I had an alarm that kept me awake so I'm one narcotics I'm tired I had a couple panic attacks I'm miserable I'm ready to go say come on nurse how much longer am I gonna be here to which she replies imagine I'm not really with it we'll keep you here a few more days and

21:03then we'll move you to the floor the hell kind of hospital is this I only get a bed as long as I'm in ICU turns out those of you in the hospital industry this is obvious the floor is just the regular rooms not the ICU rooms so all right I'm gonna have to hold it together on this one last time I lost it and I couldn't took me a little while so let me prepare myself here this is what I was missing my daughter was too this was her first like Halloween where she was aware kind of what's going on and she was into it

21:43miss you daddy hey Clark Clark are you a chicken they love you daddy so I'm getting videos and pictures and then kids aren't allowed to code I see you I think it's like 13 I mean there's just too many wires and things they're worried so I can't see her I'm stuck in ICU I'm miserable and I'm not working on sifter you know it's just it's rough it's rough and so I get out of ICU and I start thinking more seriously about sifter what the future is at the time nothing happened but this is about the time I reached out to Kristen Natalie at Wilde to say and I mean I knew if I sold

22:35sifter they were the first people I called sifter used one of the products integrated with another one I'd work with the team a bunch I knew what kind of company they were and I saw that and working with them as being key to my recovery being in a good place with a good team nothing worked out at the time it didn't make sense I was kind of afraid I was just chickening out because this was the lowest point and we decided to just stay in touch and we did but nothing happened at that point then I start getting into ok I've got my flap time to recover at this point we still

23:13believe and hope that amputations off the table it's never even going to be close to being on the radar things don't automatically it's not just magic right you don't just start up it's not if you build it they will come right it's a lot of work growth though and this is something I learned way too late sifter plateaued a couple times and we always would get through it one way or another but I didn't think about it this way and I should have it's just a math problem growth is only a math problem right so there's your straight line of your hypothetical growth with no churn you

23:51will grow and it will be awesome but churn exists and there's only so much you can do right some companies go out of business churn happens so there's a formula and it's you know if you have a hundred customers and you lose ten a month and you're gaining ten a month you're plateauing and so there's gonna be a point formulaic ly where you will Plateau it may be 500 customers it may be a thousand customers but it will happen at that point all it is is about working on the right things right there's a few things you can adjust their styles you turn things you focus on and you really

24:27need to laser focus in on them you need to know what those numbers are but it's a really simple formula and it can be more complicated in this but this in hindsight would have helped me focus so much and know where to spend my time instead of spinning my wheels and stressing out about whether we're working on the right things one see what your turns at try to reduce it turns your leaky bucket if you've got a leaky bucket there's no point in pouring more water in it if it's barely leaking you're probably okay increase conversion right if you want a website that converts visitors you don't want to

24:59throw paid traffic at a website that's not converting it's pretty simple then if you got those things taken care of get traffic find more traffic however you want to do that whatever's right for your product and break it down and keep it simple because otherwise you can work on all three of these things at the same time you can work on a bunch of things but it can be a distraction you have to stay focused to that end like we come at things thinking we can handle all this and like physical therapy when I start physical therapy I didn't just walk in and me I I'm gonna deadlift 500 pounds I

25:34mean I couldn't even stand without crutches right it's impossible it's beyond insane but that's what we keep trying to do with businesses right we get an idea and like I'm gonna build this and it gets good scope just increases and increases until you don't launch and it drags on and it's painful you have to ease into it right start small with those baby steps work up to it right learn iterate and just constantly make progress we do this in our careers all the time right anybody who's learned CSS right when you first started especially if you were dealing with floats you just want to throw your

26:07computer across the room but eventually you've figured it out and then they came out with all flexbox and grid and variables and sass and less and it just and it just gets nuts and you got to keep up with it and you do all of this is just cycles of pain and discomfort but it's natural we want to avoid it which would like to avoid it we try to avoid it but we don't need to avoid it you need to embrace it and understand that that's just growth in disguise that's all it is so after you've done all this you know at some point you want

26:43to step back and say how am i doing am i happy should i reassess and of course so I deal with my leg Here I am I've got my free flap I can walk it's tolerable I can do a little bit of physical therapy and I can bike and it's a little tolerable and it's alright snowboarding nope painkillers I took painkillers and a beer to pull that off and then running a basketball completely out of the question nope nope nope and it was really easy to think alright this is not working this is not going well and I started realizing I needed to focus not on these

27:24long-term goals like someday maybe I'll be able to do that stuff but it's more important to focus on the winds and the things that are present right here and right now can I walk further than I could can I go a mile can I go two miles how long do I need to go without sitting like these little things and they started adding up like really little winds can I put my pants on without sitting down that was a big one because balancing on one leg it takes a while and it hurts at first because your legs not used to it so like these little wins

27:55like Randall Lauren I'm like I put my pants on with without sitting down it's like a little kid and but it was so invigorating in a way that like these little wins you've got to look for those little wins and appreciate them because they're there but we overlooked them we take them for granted because we want the big wins but the big wins build on those little wins sometimes you got to make big decisions big decisions are big decisions for a reason they're hard right like patrick said they're very very few that are trapdoors the leg is a trapdoor I can't put it back on there

28:30was no command Z for my leg and that was the primary fear with the leg that's not the outcome it's just that there's no undo if it sucks so the key thing is you really have to stay focused you know it's easy to dance around and want to avoid the big decisions and not make them because they're so difficult and the outcomes are scary in my case my ankle wasn't doing good the flap you know it healed my ankle was out of position and because of that when I walked the front of my bones were grinding together and I was getting some arthritis and a lot of pain so let's think about

29:15this imputation thing again how would that be I read a couple more books gave it some thought thing is with amputees active amputees specifically there's only one problem and it's regret you might think regret that it they did it but it's almost universal the only regret is not doing it sooner we're too afraid of it because we're letting something go so so permanently and it's hard hindsight's 2020 I'm firmly in that camp I should have amputated three months into this and got over with instead I basically put life on pause for five years while we fought it not to say that you should rush into an

29:59amputation but it's not as bad as everybody thinks same time we welcomed our second daughter and starting to think more like alright well what does the fusion look like what does an amputation look like theoretically effusions a six-month recovery done no big deal amputation theoretically it takes 18 months until you're really through it and Lauren's gonna have a lot more burden we've got young daughters like this is a terrible terrible decision I wanted to amputate very very badly at this point I felt like that was the best long-term solution but at the same time I felt an obligation to try the simplest theoretically safest solution so of

30:44course I did they shoved some screws in my foot got it back in the right position and I gave wild bet another call and said alright I think I'm done and we sold sifter so I joined wild that put sit on the market join while bit it was difficult but it was the right thing to do for me without a doubt working it wild that has been so much healthier for me than running my own business and I think I could run a my own business better now but man did I make a lot of mistakes for myself I made a lot of other mistakes to hit a lot of other

31:23mistakes too

31:31you