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Render Positive Interviews Kyle Racki

By Jon | 23rd Jan 2016 | Posted in Positive Chats

We’ve finally put live our first ever audio podcast, enabling us to talk to wonderfully talented people across the globe.

Have a listen here:


Kyle Racki

On this podcast, I talk with Kyle Racki of Proposify (an awesome piece of web software to help streamline creating gorgeous sales proposals), located in Nova Scotia, Canada. Kyle and Kevin welcomed me onto their podcast a good few months back, and both sides enjoyed it thoroughly.

We have come full circle, and Kyle is the first guest on the first audio podcast which we’ve entitled “The Productive Procrastination Podcast”. We will still do video interviews, but we want to talk to people all over the globe and aim to get one podcast out a week, so audio only makes sense. We will be creating a weekly video blog soon too – it’s all happening!

It’s my first go at creating an audio podcast, so it doesn’t have many bells and whistles, but the content is interesting. We discuss a range of topics from the trials and tribulations of launching Proposify, how to deal with burn-out and Kyle’s upbringing in a cult!

That’s all I’ve got. Have a listen. Thank you Kyle – this was fun. Next time the turnaround will be quicker, I promise 🙂



Jon: Okay this is our first ever audio podcast.  I am joined by Kyle Racki.  We did this a few weeks ago, but I’ve only got round to learning how to set these up.  So this isn’t going to be the best, but the content is good.  I hope you enjoy it and you come back for more.

Kyle: I’m just going to press the record button, so we can have a file after.

Jon: Excellent, this is where we totally change personalities.  Now we’ve hit record.

Kyle: Yes, let’s now stop saying all that offensive…

Jon: Yeah, we’re going to be politically correct now.  Let’s change tack.  So I guess the other way around was my favourite podcast.  I probably shouldn’t say this out loud.  But it’s weird, I think audio only you’re more yourself.  When there’s a camera in front of me I seem to change.  It’s more awkward.  I guess with you guys audio means you can do it internationally.  Did you make a conscious decision to do audio or was it just –

Kyle: Yeah, actually we’ve got a couple of episodes from 2014 where we were doing video.  Actually we were doing local agencies.  So we would actually get a video guy to come out and set up lights and shoot us and everything.  It was just really expensive, time consuming, difficult to do.  So we could only really do one every month or two.  Then I wanted to do a weekly podcast.  I wanted like you said do it with people from around the world and not be limited by location.  So it was an easy choice, just do audio.

Jon: Yeah, I think I want to do more of these.  Already I’m speaking more fluently.  I think with video it’s very question, answer.  I love the ones that we’ve had already and I still want to do them, but they do take time.  I think I want to do more of these.  Because already I can tell I’m talking to you normally and it’s more conversational rather than question, answer, question, answer.  Do you know what I mean?

Kyle: The thing is generally people who listen to podcasts don’t sit there and hang on every word right?  They’re listening to it while they do something else, so there’s going to be boring bits, there’s going to be funny bits and people are just going to kind of … it’s going to be on in the background and they’ll pick up a few things if you’re lucky.  Which video you kind of have to force them to sit there and watch it.

Jon: That’s very true.  Because I can see from our Wistia stats that there’s some people who watch all of them, but a lot of people they’ll skip in and out.  There’s bits that are watched more than others.  So I like the idea of having something regular, weekly.  Do you release shows at the same time each week then?  The same date and time?  Date, same day or time or is it just once a week and you get an update?

Kyle: Yeah, we try to.  We’ve played with it a little bit in the past.  But we try to do it every Friday now.  Of course that’s different.  I think by the time we release it it’s probably five o’clock your time, it’s Saturday morning Australia time or whatever.  So it’s obviously different depending on time zone.  But we usually release it Friday morning, Friday afternoon.

Jon: Interesting.  I like this, it’s a podcast about podcasts.  

Kyle: Yeah, are we actually doing the podcast?

Jon: Well I don’t know, it’s recording so this can be the podcast.  This is truly spontaneous.

Kyle: This is what they call a cold open.

Jon: Yes.  Well I like my cold opens as you know.  Usually they’re more absurd than this.  But this is the podcast.  We’re on the podcast right now.  So I guess now is the time that we totally change.  Now that we know that we’re going live.

Kyle: Yes, okay.  

Jon: We can keep all this stuff we’ve been saying because it’s all valuable.  Have you found … hang on a second, how long have you been doing the podcasts then now?  Because I found out about it, my brother sent me the link and said you should appear on this.  I listened to a few and I liked it.  How long has it been going on now?

Kyle: We only really started the audio podcasts this February.  So it’s been just over maybe seven months.

Jon: How has it been as far as a learning experience?  Have you found that you’ve become better Jons?  Have you found that you’ve got repeat visitors that come back for the podcast now?

Kyle: Yeah.  I’m finding that it’s starting to gain momentum.  You know we have a small audience, but we get enough people.  Like for me if even a handful of people every month call or email and are like man, I listened to the podcast, it’s really good.  I mean that’s all I need.  I don’t need to be a celebrity.  I’d like to be one.  But I don’t need to be one.  Really the podcast just came because I was … see we have a product that we sell to agencies.  It’s very agency focused.  I’m a big believer in content marketing and creating content that’s valuable and helpful and it’s not just selling our wares right.  But what I found when I was blogging last year when we launched our blog was I was pulling lessons and fails and tips that I learned from running a small digital agency for five years.  

But I was starting to actually run low on ideas for content because I wasn’t actually doing it anymore.  I didn’t want to be like one of those self-professed gurus that are like selling webinars and workshops on stuff they did 20 years ago.  So I thought wouldn’t it be better to talk to people who are actually in the trenches every day running agencies, experiencing it all fresh and get their take.  Instead of me just sitting there and going “Back when I ran an agency, things were different”.

Jon: Yeah. Didn’t I see a blog post recently, was it you or Kevin relating to a cult?

Kyle: That was me.

Jon: That was you.  We could elaborate on that if that’s okay.  That’s interesting.  So this is me interviewing you.  The reverse of before of my favourite podcast.  So tell me about that.  What the hell was that like?

Kyle: Okay, so to back up, I was born and raised in Christian cult.  I don’t know how specific you want me to get.  If it’s going to offend listeners or not.

Jon: We don’t care about that, it’s fine.

Kyle: Okay.

Jon: It’s what happened to you.  It’s down to you really as much as you put it out there, so I thought you’d be comfortable talking about it.  So if you’re not comfortable.

Kyle: I am totally.  I’m actually very comfortable talking about it.  I’ve come to grips with it.  Actually it’s therapeutic to talk about it for me.  So I was raised a Jehovah’s Witness.  That’s, my parents converted when I would say they were in their early twenties, just before they had me.  So I grew up very fundamentalist Christian beliefs more or less forced upon me.  I went out every Saturday and put on my suit and with a bible and knocked on doors and tried to convert people.  Three meetings a week.  Wasn’t allowed to celebrate birthdays or holidays or Christmas or anything.  A lot of very tight restrictions.  There’s a thing in cults where you struggle, they call it cognitive dissonance.  So it’s like when you believe something is true and someone comes along and says no that’s not true.  

It causes cognitive dissonance.  So you’re actually getting uncomfortable.  It’s why a lot of people get angry when you start saying their beliefs aren’t true.  It’s a psychological thing that happens.  But when your beliefs are crazy, like off the wall crazy, like this particular group is, you’re constantly inundated with evidence that what you believe is totally not true.  Right, evolution for instance.  It’s all around us and yet we’re told that didn’t happen.  It’s a lie from Satan.  So you know I was just inundated with this cognitive dissonance throughout my twenties.  Actually this was during this time when I was still part of this group.  You know I’d started Head Space, our agency.  I had a lot of friends who were not Witnesses.

I was actually not heavily devout.  I lived a double life.  I went to my church and then I went out drinking in the pub and getting wasted with my buddies right.

Jon: So that’s cognitive dissonance.  You’ve not admitted that you’re out of the trenches there, but you kind of were.

Kyle: I kind of was for a lot of years.  The one thing that they tell you in this group, which basically all cults do is they say don’t read anything that disagrees with us.  So especially if it’s a former member.  I think Scientologists call people like that, they have a name for it.  It’s a suppressive person.

Jon: Yes.

Kyle: So for Jehovah’s Witnesses it’s an apostate.  So if you’re like I don’t agree with this anymore and I’m leaving.   You say write a blog post about it or something you’re considered an apostate and you’re the lowest of the low, scum by other Witnesses.  So I ended up … it was actually shortly after the death of my father.  Wow, this is getting really therapeutic here.  It was shortly after the death of my father in 2012 that it all came crashing down.  Actually coincidentally it was during a trip to London.  It was the first time I’d been to London, England.  Just travel expands the mind, you see different things.  I started thinking about our mortality, how short life is.  I came back and then I just read apostate literature.  

Quickly dismantled everything that I’d ever believed about the nature of reality.  So then I decided very shortly I’m going to leave, I’m done with this.  I was basically deprogrammed by it.  I announced my intention to leave.  That’s when my friends and some of my family who are in said we’ll never speak to you again.

Jon: I was going to say that’s the worst part of it, it’s the excommunication from even your family.  That’s the hardest part.  When I watch any of these documentaries on Scientology or any other cults.  It’s interesting that Jehovah’s Witnesses … is it a specific branch of it?  Because that’s like for us in Jehovah’s Witnesses, it is a niche religion here.  But I don’t think it’s considered a cult.  Is it a specific branch of Jehovah’s Witnesses or is it just considered a cult there?

Kyle: Jehovah’s Witnesses is one organisation.  So if you live in Australia or London or Canada or anywhere, you basically follow the same cult leaders.  There are literally seven dudes who live in New York.  Seven blokes I should say to align myself with your audience more.  There was actually a great UK activist who goes by the name John Cedars who has a blog called JWsurvey.  Anyway he talks a lot about the governing body and it’s very useful tool for gaining existing Jehovah’s Witnesses who are having doubts out of it.

Jon: I’ve received some of their literature outside of Oxford Circus station I think I’ve had some of their literature, like a flyer from Jehovah’s Witnesses.

Kyle: That’s a fairly new tactic they’ve only adopted in the last few years.  I guess nobody is home during the day when they’re out knocking on doors.  Everyone is out working or doing something or they don’t answer.  So now they’re putting these carts in train stations and really populated areas to try and get people interested.

Jon: For me it’s … I don’t know what your beliefs are, I don’t want to go too far into that.

Kyle: You go as far as you’re comfortable with.

Jon: Do you … because you said you had your agents here.  I always thought with the advent of the internet it’s going to make cults, all religious activity it’s going to be more question whatever your beliefs are, more difficult because the information is so out there.  If you want to look into evolution it’s never been easier.  If you want to look into all of these topics, the information is so freely out there, that it’s got to be making it more difficult for people like Scientology.  Even mainstream religion has got to be more difficult with the advent of the internet.  Did you find that was beneficial to you and how did you deal with it?  Because clearly you were still part of it while the internet was pretty big.  How did you deal with that and was it helpful?

Kyle: Yeah.  The internet is incredible tool for getting people out of cults.  It’s very difficult for people to stay in them when there’s so much information around.  Usually they do a pretty good job of just scaring the shit out of you and saying don’t google Jehovah’s Witnesses or whatever religion you happen to be part of.  Because it’s going to be all apostates that’s on there.  But actually it’s interesting and this was I believe on John’s blog that when you look at say Jehovah’s witnesses across the world, the countries that have the highest internet adoption have the biggest decline in the last 10 years.  Really the only countries where you’re seeing growth is certain places in Africa and other parts of the world where internet adoption is very low.

Jon: Yeah.  It strikes me because Canada, correct me if I’m wrong is not a particularly religious country, especially compared with the United States or even further, the Middle East.  That’s an extreme example.  Is it true that Canada is like the UK in that it’s quite a liberal, secular society or am I wrong?

Kyle: Yes.  Most of Canada I would say is fairly secular.  I think we’re somewhere between the US and Scandinavia or Iceland.  I think those countries and Sweden.  I believe those Nordic countries tend to be a little bit way on the other side of very secular and had very low religious adoption.  I’d say Canada is somewhere in between.  There’s definitely religious people here.  But I was just travelling in the States, like San Francisco last week.  San Francisco is probably as liberal and left as you get in the US.  You still just see religion everywhere.  It’s kind of taboo to talk about it.  Whereas at least where I live you can have a little bit of a go at religion and people don’t get too upset.

Jon: Yeah.  Coming out of it then what was that like? Do you go pretty wild?  You said you were already going out drinking and stuff.  Did you go pretty wild or was it … I can’t imagine what the experience must have been like.  But did you go right to the other side, where you became a party animal or whatever. What was that experience like when you’d made the decision and you were out?  Obviously difficult and exciting.  I don’t know.

Kyle: By the time I was truly out and mentally out as well as physically I was 28 years old.  I already had two children.  I had a business.  I love to party, but I also like to work hard.  So for me taking serious drugs, you know I smoke a bit of pot.  But as far as doing any heavy drugs or just going really wild, whatever that is, has just never really appealed to me.  I think what I became was the person I already was inside that I was suppressing.

Jon: That’s going to be a crazy time.  I’m just imagining going through that.  I’ve never had to face anything like that.  So where were you when this happened?  How did you go from having the agency … so you had the agency.  How many years did you have that and how did that start up?

Kyle: Well I’m a web designer.  I went to school for graphic design back in 2001, which I can’t even believe is almost 15 years ago.  So I studied graphic design.  I was doing potato prints and stuff and 35 millimetre photography.  So it was fairly old school, analogue.  We still used computers.  But Mac OSX wasn’t out yet.  So that’s how I started.  I actually wanted to be a print designer and do packaging and stuff like that.  But then as the years progressed got really into the web and interactive and started learning to code and all that kind of stuff.  Eventually I got sick of … I think like you when you were on our show, you talked about how you got a little bit sick of being at agencies, having to do things that you didn’t quite agree with.  

You know you want to be your own boss.  That’s how I felt.  I wanted to branch off and go freelance.  I never actually really thought oh I want to be an entrepreneur or I want to be a business owner.  I just wanted to live on my own terms and have the freedom of working from home and all that stuff.  So I went freelance.  Actually I did it in probably the worst way possible.  I think you said that you guys maybe saved up a bit of coin and prepared to go out on your own.

Jon: For a few months.

Kyle: A few months?

Jon: Yeah, not a massive amount.  But I did have enough to survive for maybe three months.  It was a gamble.  But it wasn’t like I had nothing at all.

Kyle: Yeah.  For me I was building up a freelance career for about a year.  I was working full time at an agency as a designer.  Then I was on the side after work on the weekends I was working on some client work.  But eventually I was just … actually it was my wife said to me are you going to shit or get off the pot kind of thing.  So that’s what I ended up doing.  I had debt.  I had no money saved up, but I’d just got a job that was like a website job that was paying me $3400, which was about a month of my salary at the time.  So I knew I had at least 30 days to go and find some more work.  So that’s when I quit and went out on my own.  Then from there I worked for about a year freelancing.  I liked it.  I was good at it.  

I made much better money than I did working for other people.  But I just started getting a bit lonely, missing a team environment.  That’s where Kevin, who was actually working as a sales guy at the same agency I was at.  He was looking to go on on his own and maybe do some consulting.  I said well why don’t you just … I was calling myself Head Space, that was my freelance name.  Why don’t you just come join with me, we’ll start hiring some people, building it up and we’ll go from there.

Jon: How nice.  So you say you ran it for five years and then Proposify came along and you had to make the decision we need to do this full time, you can’t half-heartedly do this?  Have I got that correct?

Kyle: Yes, exactly.  It was very kind of more gradual.  Maybe a bit more convoluted than that.  But essentially that was it.

Jon: So I’m at that stage now where things are getting very exciting.  I always thought I’d have my own agency.  It’d immediately be a success.  We did have great growth.  Then it kind of stayed the same for a few years.  Now it’s getting really exciting again.  It’s really because we’ve got a great team.  But on the sales side I’ve really started to put the time and effort in.  But I am … although it’s really exciting and I’m asking for free advice, you’re like my shrink or something.  I’ve got some really massive life changing deals in the pipeline.  But at the same time as that you do have nights where is this worth it.  You know when you’re exhausted.  Do you still have those feelings, where it’s exciting but sometimes you question?  

I don’t know how much time you’re putting into it.  Where you still have those worries of am I overworking, what is all this for?  Do you still have those fears?

Kyle: Yeah, I do actually.  I mean congratulations on the big exciting deals.  I know you’re a sales maniac.  You know your shit right.  So obviously it’s all bearing fruit.  But as far as do you ever get overwhelmed and almost in a sense you can get tired of things even if you’re successful at it.  Even if good things are happening.  I’ve felt like that.  Sometimes it just comes down to being tired of the grind and the hustle.  I mean take a vacation you know.  Like everything goes in waves.  In most businesses you’ve got the highs are really high and the lows are really low.  Whereas for your average person who just clocks in at a job every day, they don’t get as many lows or the lows aren’t as deep.  

But the highs aren’t as high either.  So there’s always that trade off where you go okay, if I just took a job and worked for somebody, I could have a much more stable consistent life.  Not work as many hours, watch TV for five hours a day or whatever you want to do.  But I wouldn’t experience the rush of landing a huge deal or getting … whatever the highs are for you.  So I’m just learning to really appreciate the highs.  When everything is going great, it’s natural for us to say what’s next?  Like okay, is this it?  What’s the next thing?  Things could still be a little bit better here.  I guess what I’ve really tried to do over the years is just enjoy it.  Like sit back and enjoy it.  Take some time off and think about how awesome it is.  Because you don’t know when the next low is going to happen.

Jon: Yeah.  You’re absolutely right.  You’ve hit the nail on the head with how I’m feeling at the moment.  I’ve always had those highs and lows.  But what you said about even when it’s good and even when it’s successful, it can still be troubling and overwhelming.  It’s good to hear that out loud from someone else.  Because that’s exactly what I’m going through at the moment.  We’re going through really exciting times, but also it’s very tiring.  It’s good to hear that out loud that even when it’s successful it can still be overwhelming.  It’s good to hear it out loud.  How is … to move on slightly, how is Proposify doing at the moment?  Is it going to plan?  Do you have even have strict plans that you want to stick to?  Is it all going how you thought it would be?  How is it all working?

Kyle: It’s actually going better than I thought it would be.  So I’m going through this period now which is maybe why what I said resonated with you because I’m in a similar spot where for the past two years I guess before this year it really felt like we were fighting for our lives.  We were trying to get rid of our agency, sell it off.  The agency was … it had debt.  It wasn’t highly profitable or really profitable at all.  It was always just playing the game of trying to make payroll.  So it was a very stressful last couple of years running the agency, whilst also putting all the time and resources and energy into getting the product Proposify off the ground.  Then through the process of selling it, which was miserable and long.  I wanted to murder people.  It was really low.  

I don’t normally get depressed, but I was very depressed for a time where I just wanted to give up on everything.  Then finally we managed to raise the money we needed to really focus full time on it.  The agency sold, so it got off our hands.  So then we were just left with okay, good everything we wanted to happen happened.  But we don’t have customers.  So we should really work on it.  So we knew we had a runway.  We knew we had until March of this year basically.  This was May 2014.  So we knew we had until about March of this year 2015 until the money ran out.  So it felt like laying down the train tracks, while the train is coming behind you.  But then we noticed around September of last year, suddenly we noticed, we could get people into the product using it and then they would leave or they would cancel or they’d maybe sign up for a month and then quit.

But then we noticed a big spike.  It went from like 20 customers to 40 or something in a month.  So the growth has been very steady since then.  Now it’s pretty amazing to look back and think last August we had 30 paid customers and this August we had 1200.

Jon: Oh excellent.  That’s very transparent of you giving out those figures.  But that is enormous growth.  So did you find that there was a point where there was the tipping point?  Where it just flew?  Was it something with the product that was fixed or retention?  Or was it some event of PR that got you seen by people.  Can you attribute it or is it very difficult to do that?

Kyle: I’ve heard it said actually that it’s very … when you ask product entrepreneurs, product companies how they hit product market fit, most will be able to look back and not really know and probably give you the wrong answer.  So take that with a grain of salt.  I don’t really know what it was.  I think … the only thing I can attribute it to … I don’t know if it was specifically one thing.  I don’t think it was necessarily marketing because I think that we had a decent enough volume of people coming to the site anyway, just through search and referral and enough traffic that if we could convert some of it we would do fine.  But we just weren’t converting any of it at the time.  

So in September all of a sudden we just started converting more.  All I could really attribute that back to is just months, a year steady of putting the product in front of people, watching them use it, calling them, interviewing them, finding out where the holes were, finding out what features we were missing.  Just nonstop customer development.  Then we didn’t stop doing that.  So as soon as we noticed a change in September when more people were signing on and paying for it and we were retaining more of them, we just constantly kept calling customers, kept taking emails.  Kept learning what were we doing bad, what were we doing good.  What did they want to see?  Then the growth just kept going.

Jon: Oh fantastic.  So now would you say you’re in a comfortable position?  Obviously not resting on your laurels I imagine.  Are you comfortable now?

Kyle: I’m fighting that urge.  Because I know what that means.  That was in fact one of the mistakes I made at Head Space.  Because in our first year we were doing really good.  We’d got a lot of big clients.  We’d built up a small team.  Things were going amazing and that was my first time really running a business.  So in my young naivety I kind of thought wow, if growth is going at this rate and we’re making this much, then that means I can spend this much.  We’re going to be making double next year.  Quickly realised that was a really dumb move.  So I’m trying not to make the same mistake this time with this business.  I mean even though it is naturally the kind of business that scales a lot easier than a service business.  

I also know that once you hit product market fit, it’s great.  It means you can now really invest in marketing and scaling your customer base.  But at the same time it’s … you don’t necessarily have product market fit forever.  Markets change, competitors come in.  So really we just have to keep pouring oil on the fire to keep it going.

Jon: That’s one of my mistakes I think in … is when we stayed at the same … you know we didn’t grow, we stayed at the same level is coasting when things are good.  But when there’s that dip or you … I get frustrated.  I suddenly realise I’m in the same position I was two years ago from a financial point of view.  It’s when my back is against the wall that I start to do adventurous daring things and it starts to peak again.  I’m wondering … obviously when that happens I’m at my very best.  I don’t know if there’s a way of doing that when times are good forcing that kind of ambition.  Or if it’s even possible because you start to burn out like maybe I’m doing right now.  So you know when you say you don’t want to say it out loud that things are comfortable.  

I wonder if we’re on the same page there as you don’t want to admit that because then you start to just coast and start to not really … I wish you could … you always want to be in that mode where you’re as ambitious as you are when things are terrifying.  I don’t know if that’s where you are.

Kyle: Oh yeah exactly.  It’s the same reason you can lift a car up if a family member is about to be crushed.  Because you get this rush of adrenaline and you can just pick up a car and move it to get somebody safe.  But you just can’t be in adrenaline mode forever.  You’ll get completely burned out.  I guess to use another analogy it’s like when people are trying to climb to the top of the hill, you know playing king of the hill, they’re exerting themselves, they’re throwing people out of the way, they’re doing whatever it takes.  Once you get up there it’s like where else do you go?  At least that’s the feeling.  So it’s natural for people to wait to be dethroned.  So I don’t know.  I wish I had it figured out.  

I guess maybe I’m in the same spot where I don’t want to say we’re exactly where I want to be.  Because then am I going to just take my foot off the gas pedal and stop trying.

Jon: Because I always move the goal posts.  For me it was like when we get an office, when we get our first big client, so you always move the goal posts.  I think that’s the entrepreneurial spirit.  If you didn’t have that then we would just have jobs.  I don’t think I could go back to having a job now.  Because although you can clock in and clock out I never think I’d be satisfied.  I think I like this too much.  As much as I sometimes think it’s overwhelming, I think I’d be more miserable with things being underwhelming.  Yeah, I think I’m unemployable now, so this better work out.

Kyle: Yes, once you get that entrepreneurial disease you’re sworn off full time work for life right.  So there’s something I want to say here where I think that it’s possible to keep your ambition and to keep reaching for the starts and trying to make your business the best it can be and try to be the best in the world.  We don’t need to set our sights low and be like okay, I could be good for the area I’m in.  You probably don’t face that in London because you’re up against the best in the world.  You are one of the best in the world.  But at least for me anyway, just being in a small city in a place that most people don’t know where the hell it is.  I was down in the States and half the people who asked where I’m from, I said Halifax.  

They’re like what’s that?  Like Sweden?  I was like no, a short drive from your country my friends.  I think that what’s really important is you do need that adrenaline rush to get your business off the ground or to push through those hurdles or to reach that next level of like whatever it is, get an office or reach a certain amount of customers.  Or reach a certain amount of revenue, which is probably what the goal posts should be.  But I think once you’re there, you should keep setting your sights higher and keep … especially as the founder or the CEO.  It becomes less your job to answer every email and take every call and sell every account.  What really becomes your job as you grow is to keep the vision and set the vision and lead your team towards it.  Empower them to help you get there.

That’s what I’m trying to do.  So you don’t necessarily need to … it doesn’t need to be as much of a grind where you’re doing everything.   You start to be able to take off hats as you hire people.  Okay, I was doing the marketing and the development and the design and all this stuff.  Now I can start to hire people who are actually frankly better at it.  As long as I’ve got the vision to lead them there.  That was one of the other mistakes I made with Head Space was that I really liked doing design, so I kept working on design, when I should have been working on being the business leader and the team leader.  Which I got too head down in the work.

Jon: I even have that now probably A with … I’ll probably still continue to do sales because I think that’s still the job of a CEO, especially in an agency of my size.  But with me, with you it was design and with me it’s copy writing.  I still love writing good copy.  I can see why David [Ogilvy] had copy writer after his name instead of CEO even though he was head of one of the biggest agencies in the world.  I have a very similar thing at the moment.  Where my brother who is the managing director has said you should not be writing copy, you’re the CEO.  So I’m going through at the moment that you like doing certain things.  But there’s other people that can do this.  So it very much resonates with me.

Kyle: I think what’s probably better of a CEO is if you have a craft that you enjoy whether it’s copywriting, design, coding, but you’ve got people employed who run your business to do that better and your time is better spent on other things.  I mean I think I’m a big believer in side projects.  To just keep your juices flowing.  You know whether it’s like writing a screen play or just having your own blog or whatever it is to just work on your craft, keep up with it.  Enjoy it as a hobby.  But not let it influence your … the most important thing at least for your career, which is your business.

Jon: It’s weirdly exactly what I’m doing at the moment is I started in January.  I started writing a novel and it’s turned into a screen play.  I’ve started just writing for fun.  Because I realised if I can write essentially a spam email or a direct mail that people really enjoy.  I can surely write stuff that people have chosen to read.  It’s turning out that way.  Obviously friends will always say things are well written.  But I’ve sent this to so many people and they enjoy it.  So I’m thinking there’s another avenue.  It’s also in writing it’s something for my manic mind to think about that’s of no consequence.  Rather than me constantly worrying about work, which is obviously of huge consequent.  It’s no benefit to just worry about stuff.  So yeah, do you have side projects?  Do you still do design or other things for fun?  Do you take your own advice?

Kyle: A little bit.  I’m starting to do it more.  I actually … I find I’m becoming less and less interested in design, which is sad to say.  I still can do it.  I probably in the last year did the most on the product itself, just being the lead designer or the only designer for a long time until we hired another one.  So I didn’t really have time for side projects until recently.  One thing I worked on recently was a … you know the guy I was telling you about, the ex-Jehovah’s Witness activist John Cedars is he publishes this survey results from other ex-members of the JW community.  So I’ve designed it into an infographic for him.  That was something I just did a week ago.  Just to help give back to that community.  

I mean I could maybe see myself doing more.  But actually like yourself and probably not as good.  What I’m finding I enjoy a lot more is the writing point and the creating of content, much more than design.  So I think if I do any side project it’s going to be keep working on our company blog.  But also work more on building up my personal brand a little bit and creating content that’s not as targeted for getting customers.

Jon: Yes, same here.  It looks like we’re going in the same direction.  I wonder if I’ll launch a software as a service business in the next few years.  I’ll be coming to you for advice.  I don’t know.

Kyle: Well actually that’s a big part of what I want to write about.  It’s not very appropriate content for the Proposify blog.  But that’s something I want to do a lot on my own is create content.  Because now I feel like I’ve been through the process a little bit of building a company and at least getting it to the point where it’s starting to scale.  I think a lot of people have that goal or that dream in mind, where they want to build a product.  They want to get out of the service business and just build one thing that people pay to use.  So it would be kind of more creating content for those people.

Jon: But they don’t realise what lies before them.  They think that all their problems will be solved if I have this nice simple product.  It’s all going to be easy.  I won’t have to deal with clients anymore.  But you know what to say  to comfort those people I guess.

Kyle: Well I have to say I do really enjoy the current business.  I’m doing much more –

Jon: Of course, I’m not saying that.  But it’s not as easy as … there’s a lot of complexities which is why you want to write about it I imagine.  

Kyle: It’s like playing guitar right.  Do you play an instrument?

Jon: No, I tried bass guitar years ago and I enjoyed it.  But it was one of the things I never picked up.  Words are my things.  But sorry, to go on.

Kyle: Okay, so I’ll use that as an example.  My dad played guitar and I picked it up when I was 12 and have been playing ever since.  Sometimes I’ll meet an adult who says, oh I want to learn guitar too.  So they go and they buy themselves the most expensive guitar because they’re grownups and they can afford it.  Within a week it’s under their bed or they’re trying to sell it off.  Because they’re like, I’m never going to do this.  Because they don’t actually want to learn to play guitar, they want to be good at guitar.  Those are two totally different things.  When I was a kid or a teenager and had the time like it wasn’t a chore.  I just picked up that guitar and played it every day.  From the moment I got home from school until I went to bed.  It was enjoyable.  You have to just enjoy the process.

Jon: Yes.

Kyle: So it’s like that with the [SaaS] business or building a product.  We underestimate how much time it’s going to take to actually get a product that’s got product market fit.  That people pay that scales that has low churn.  That’s all that good stuff that you want in a SaaS business.  It takes years.  I mean it can take two, three, four years.  I came up with the idea actually in 2007, before I ever started working on it.  So it’s a very long process.  But once you get there it’s great, it’s a lot of fun.

Jon: May I say yeah, the first thing , the first thing like Proposify I saw was Bidsketch and you have beaten them in every conceivable way.  I’m sure you’ve got other competitors.  But it’s like night and day.  When I say Proposify, I’ve seen something like this before.  When I started using it, it was like oh okay, this is actually fantastic.  Yeah, it is like night and day between the two.  I’m sure it’s … I’m sure you’ve got other competitors.  But just that comparison, yeah, you’re so much better.

Kyle: Yeah, I think like maybe in Bidsketch’s defence to some degree they were first to market.  Or at least they were the first that I noticed that were probably around the 2008 2009 I think was when they launched.  They were basically fulfilling that proposal writing need.  But they didn’t have anything to compare it to.  There was no other players in the space.  Also the web wasn’t quite the same even five, six, seven years ago right.  We still had to deal with Internet Explorer and just JavaScript. There was just a lot of things.  The web has gotten a lot more powerful since.  I know everybody likes to think they were the first to come up with an idea.  

So I’ll be one of those guys and be like I actually had the idea for a Proposify before Bidsketch came out.  But once I googled it and found Bidsketch I was like oh shit somebody did it already.  But then once I started looking at. I thought this isn’t at all like my vision for the product.  Which is I want to make it like InDesign because that’s what I use to design proposals.  But I want it to be in the browser, like Basecamp or one of those other SaaS products.  Nobody had really done it until we started working on the idea, more competitors came out.  But nobody thought about I guess making that creative, visual, very design heavy approach.

Jon: It’s definitely made, not to make this into like a huge advert for you guys.  But yeah, it’s definitely made my life easier and as we’ve got a new sales guy on board now, he’s going to be introduced to it.  So you definitely won me over to the audio podcast world.  I want to do this.  Because I can do this once a week, quite comfortably and it’s quite enjoyable.  So thank you very much for that.

Kyle: Oh yeah it is, it’s great.

Jon: I think this format of we’re hitting on 50 minutes, so I should probably let you head off.  But this has been fun man.  I want to do this for a personal podcast.  But I also want to do one for Render Positive, that’s audio, so I can speak to people all over the world.  So I think you’ve won me over to this and Proposify and I don’t know if you’ve got anything else to say to the audience.  But, thank you very much.

Kyle: I look forward to listening to the podcast from now on, even when it’s not me talking.  Thank you very much for letting me be your first guest.  Let’s keep going.  Also people listening, reach out to us.  Reach out to me, reach out to John and talk with us because we love that.

Jon: Awesome.  Thank you very much.  I hope this has all recorded fine.  It said it was.

Kyle: I will send you the MP3 right after.  Actually UberConference is pretty reliable I’ve found.

Jon: Fantastic. I was worrying like half way through like it says recording, but I don’t know.  I’m relying on Kyle here, so fingers crossed.

Kyle: I hope to not let you down.

Jon: Thank you very much man, have a good day.

Kyle: Thanks John.  See you man.  You too.

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Meet the team

Jon Buchan
Hannah Brown
Jenny Longmuir
Tess Bowles
Lee Buchan
Asher Baker
Bree Van Zyl
Sam Reynolds
Aida Staskeviciute
Laura Reddington
Dipak Hemraj
Jess Collett
Gemma MacNaught
Laila Khan
Gary Buchan
James Hackney
Stuart Lawrence

Jon Buchan Chief Executive Officer
07949 283 785
Hannah Brown Creative Yet Technical Manager
07453 779 030
Jenny Longmuir Content Marketing Editor
Tess Bowles Social Media & Content Marketing Manager
Lee Buchan SEO and Social Media Executive
Asher Baker SEO & PPC Manager (and Lord)
07525 744 178
Bree Van Zyl Video Productionista
Sam Reynolds Copywriter
Aida Staskeviciute Graphic Designer
Laura Reddington Copywriter
Dipak Hemraj All Rounder
Jess Collett Copywriter
Gemma MacNaught Head of UX and Conversion Rate Optimisation
Laila Khan Head of PR
Gary Buchan Managing Director
07525 839 157
James Hackney Client Services Manager
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Stuart Lawrence Chief Technical Officer
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