Build with Balance: Proposify's approach to Growth and Work-Life Harmony.

Speaker 1: 0:05

Welcome to another episode of the SaaScast. Here we have a simple rule no jargon, no fluff, just bite-sized advice from some of the biggest names in the SaaS world. And today I'm thrilled to have the founder of Proposify their leading proposal management SaaS platform that's helped over 10,000 customers in over 50 countries increase their close rates by two times the industry average. So I'm definitely curious to know how you've given them such an unfair advantage to your customers. But it's an honor to have you with us, kyle. Why don't we kick things off? Can you share a little bit about yourself and what inspired the idea behind the company?

Speaker 2: 0:39

Yeah, thanks for having me, Jason, excited to be on.

Speaker 2: 0:41

So I'm a designer by trade.

Speaker 2: 0:43

That's what I went to school for study graphic design in the early 2000s, got into web development web design around that time Eventually went out on my own as a freelancer and that was kind of my first foray into entrepreneurship at about 24 years old.

Speaker 2: 1:00

And then a colleague that I worked with at an agency who's 20 years my senior Kevin.

Speaker 2: 1:07

He and I built an agency, so we went through a lot of learnings there over five years and then eventually spun out a couple of product ideas, but none of them really took hold but had this whole idea kicking in the back of my head for years, which was, you know, proposals are very time consuming and there's a lot of inefficiencies at least what I had experienced at agencies, both my own and previous ones, I would so just always thought there should be like an app or some sort of project management software for proposals wasn't a lot on the market at the time other than just basic quoting software.

Speaker 2: 1:45

So that was where the idea came from. And then, over the course of running the agency and, you know, getting the idea out there, showing it to people, it clicked. People had the need, they had the pain and we just had to figure out how to solve it. So there was you know we can dig into this more but a lot of near death experiences trying to just get it out the door and find product markers fit, not run out of money, that kind of thing.

Speaker 1: 2:08

But yeah, we're all the standard, all the standard experiences and feelings of that of scaling a business. So that's incredible. How many people are you today? And I mean, obviously you started, sounds like pretty organically, right from within the company that you're already operating. So I love that too. It's like by scratching your own edge, you can build a better product. So, yeah, that's a great intro. How many people are you today? What? How big is your?

Speaker 2: 2:36

company. We're about 55 or so employees. Okay, yeah, so we've raised a bit of money over the years. We didn't raise a lot. It was something that Kevin and I were very intentional about from the beginning, because we weren't trying to, you know, raise round after round of VC money and become, you know, become a unicorn.

Speaker 1: 2:56

So yeah, and so you're dynamic with your co-founder. So are you still more like design and product and your co-founder be more like technical, or yeah, tell me more about the dynamic between you guys.

Speaker 2: 3:10

Kevin is more on the biz dev side, more on the sales side. I'm probably more on the product marketing technical side. Neither of us are developers, though, so we rely on very smart engineering leaders on that front, gotcha.

Speaker 1: 3:30

And so you're from out east and you guys had quite the epic storm a couple weeks back. Tell me about that. What happened? I know it wasn't as bad or severe as some of the other ones you had mentioned, but yeah, you guys okay and everything's good.

Speaker 2: 3:46

We're okay. You know, the last 10 years or so we've been getting more hurricanes up this way that swing up from the sort of, you know, middle of the Atlantic that goes by Florida, goes by you know, the Carolinas, and sometimes they hit Nova Scotia. So yeah, we got one the other day, that wasn't too bad. Or a couple weeks ago there was one in the summer, though that actually caused a lot of flooding. Lightning literally hit my house and like blew up a part of my roof.

Speaker 1: 4:12

So yeah, they're getting worse, but oh and that's the unrehearsed but perfect segue in today's theme of the topic.

Speaker 1: 4:20

So you, you know, like you go one minute where it's completely calm to the next minute in your house being striked by lightning and there's absolute chaos. And so I think a big part of entrepreneurship is managing the unexpected, and it's you know, I think you can all agree, it turns really quickly, and so, you know, it brings new challenges, it tests our resilience almost every single day, and so the goal of today's you know chat is really to how can we help equip entrepreneurs with the mindset and the tools necessary to navigate this adversity that they're going to be facing, through the stories of other great leaders within SAS. And so, you know, my first question is can you, you know, recall maybe you know one significant time in your company's history where you know you were up against a wall and you didn't know what to do next and just kind of, like you know, set the stage for the types of, you know, situations that you've had to navigate through that have been a little bit more in the chaotic side?

Speaker 2: 5:21

I feel like that happens every week, you know. I mean you know a lot of times SAS founders who are trying to get something off the ground. That's a very hard period of building a SAS business and most don't really find product market fit in scale. The majority, you know, are essentially building a product nobody wants and it takes them time to realize that and they either have to pivot or they run out of money, that kind of thing. But once you're there, once you're kind of scaling, once you're kind of at the one million or so mark, a lot of times it's it's you can get naive and think, well, it's all smooth sailing from here, but the one to 10 million climb is is hard, really difficult. Yeah, we had when we found product market fit and we were starting to scale rapidly.

Speaker 2: 6:11

I remember those periods being fun, you know, hard in some ways, but really just fun, because every week you were looking at your growth rate and going like, wow, where we just keep? You know the challenge is how do we keep pace with the growth? You know, who do we hire to help support the growth? But you know, inevitably there comes a wall where you just kind of hit it and you go either your churn catches up with you. So a lot of people kind of ignore churn in the early days. They're like it doesn't matter, we're growing so fast. But if your churn is too high then at some point you're going to just hit, you know, the, the plateau where you can't really grow more because you're just losing so many customers and you have to just keep pouring money into acquisition.

Speaker 2: 6:56

So you know, that's that's something that we ran into at about three or four million was. We just looked at the numbers and we said, you know, based on how many small customers were coming into the product, it was going to be impossible to scale if we didn't figure something out. And that was when we decided we need to do something. And I can dig more into that, but I think that was one time. Another time was just dealing with really unsupportive board members and investors who were totally the wrong fit and were essentially trying to more or less kill the company and take it out from under. Me and Kevin the worst nightmare of most founders when they raise Thankfully, not our existing investors but former ones.

Speaker 1: 7:45

Gotcha and so like. In those moments when you're up against the wall, fear can often stifle creativity, and so I'm wondering if you can share some strategies that you've nurtured and developed over time to embrace these challenges and, more importantly, even kind of celebrate failures as you walk along that fine line of getting to the right path and solution.

Speaker 2: 8:09

Yeah, I mean it takes time to develop it. It's a mindset right, and I think it's impossible to prepare for you kind of have to go through the storm and that's where you kind of find out what you're made of and you're either going to dig deep and get coached and read and try to build that mindset to push through. And some founders they opt out, they say this is too hard and they either want to sell or they just sabotage the business by not being in it and the company. If you've done a good job up to that point, getting a management team and getting processes in place, the company can go for a while without the founder, without the CEO, but eventually they're going to need that founder CEO, really kind of leading the company to hey, this is where we're going and people will feed off the energy, and so if you're sick of it and bored and frustrated and you're checked out, that's lead through the whole business.

Speaker 1: 9:16

So what do you do in that situation, like when you were mentioning that? I can recall times where that's happened to me on my entrepreneurial journey, whether it's chasing the carrot too long and not seeing the signs of success I'm looking for, or even things like imposter syndrome and really questioning my ability as a leader. What can we do to help manage these feelings as we go through these challenging times? I know you mentioned reading and having a mentor, and those are very common ones, but when you're in that chaotic state, what if you can't get a hold of your mentor? What's next? Like what are the practical things that I can be doing to avoid the meltdowns and alluding fear to the rest of the team?

Speaker 2: 10:04

Yeah, there's no magic bullets, but I think some things that have helped me have been things that people have said to me kind of gave me some unlocks, and one of those was when I was at a point where I said I'm sick of this, I want to get out. I've been doing this too long. I'm not where I want us to be. My coach had said so. Basically, you're saying that this is your peak, this is as high as you can go. So if you sell the business and you get out and you start something else, you'll only ever make it here. You can't grow beyond that Because it's so easy to want to hit the escape hatch and go. Well, if I did it over again, it would be different. But it's like you can't fix your own business If you can't retool it and get it where it needs to be. Who says you're going to do it again, starting back at zero?

Speaker 1: 10:52

You're just going backwards, yeah, and I mean when you think about the odds of success being one out of 10, right. So I mean that's sage advice. I think, on that theme, the best advice I actually got was from a former NBA player called Shane Bachier, and we were hanging out at Clision and we were talking about what makes an Olympian of tech, and one of the traits that his coach tried to instill into all of them was really this mindset of focusing on the next play. Like, basically, focus on the outcome, that the past plays, the failures, the wins none of that really matters. Just keep your focus on what's next and what's coming. And that's really helped me.

Speaker 1: 11:40

It's just like the simple mantra for life, and interesting that it came from sports, right, but you can hear a few coaches just screaming it out on the court when their teams need it. But, yeah, so I mean there's nuggets of wisdom along the way, there's books, there's things like I've done as gratitude journal, like really reframing the things has helped me. Meditation and, like you said, if you're checked out as a founder, then check out for a bit, come back refreshed and renewed and restored, right. And so I think, like, what support do you provide your employees that are also going through this with you. Like what do you think a founder should be thinking about when it comes to their team? That's going through the very same thing that they're going through, just in different ways, of course, maybe less emotional or less table stakes involved.

Speaker 2: 12:40

Well, I think your employees can be going through personal issues and chances are, at any given time, a handful One or more of your employees will be going through a divorce or a health issue or issues with their kids or whatever. But really, I think if we're talking business challenges, it's really, you know, if the company is not performing where it needs to be. That obviously bleeds into the culture and the sort of morale of the team. Right, people don't want to be on a losing team. They don't like losing. So I think it's on the founder to be very direct when speaking to the company in terms of we are not where we want to be. Here are the problems we're seeing, here's where we want to get to, here's what we need to solve. This is our objective. And staying not positive for the sake of positivity, like hey, let's just bury our head in the sand and it will all be OK, but really trying to balance that. You know, don't hide the numbers, don't hide the lack of results. If you're seeing them, be clear. We're not where we need to be, but this is where we're going. This is why it matters. I think if you can develop that ability to communicate it to your team, they'll see it and the ones who don't will opt out, and I think that's one of the most important traits for founders to develop is the ability to curate your team, especially your leadership team, your executive team.

Speaker 2: 14:12

I coach founders who hang on to people too long, who just can't get where they need to go and they're reluctant to find a better fit for them, and level up the leadership. Bring in more experienced leaders. Most take too long I still take too long sometimes but I think that is key. Because you bring in elite, say, as a company, you might not be performing and that might be external forces. We're in a weak economy.

Speaker 2: 14:44

It's tough in SAS. More people are sales cycles are longer, more people are getting rid of tools. It's not just consolidating, so it's a tough time. Externally. There's also competitive threats. There's more competition in SAS than ever before. And then obviously, as a company, you need to guide the strategy of making those choices. How are we, where are we going to play? How are we going to win? What are the capabilities we need in order to execute on that? But if it comes down to departmental, it really comes down to the leader. So if you have one department in your company that is not performing over an extended period of time, it's always the leader's fault.

Speaker 1: 15:23

Yeah, of course. I mean the ownership and accountability and not taking a victim mindset is just. If you have that at the top, that's just going to erode and go right through the organization very, very quickly. You mentioned during crisis you had some investors that were not necessarily thinking about the best interests of the company, maybe themselves, or they had other motivations and desires to steer you in a direction. But outside of that scenario, how have you used your investors or leverage to them during crises and then, more so, even after the crisis? What roles do they play? What advice would you have for founders that think they're going in it alone, but people have written checks saying I'll go to war with you.

Speaker 2: 16:12

Yeah, so I mean assuming you've found great investors and we have incredible lead investors in CBGF, which is the Canadian Business Growth Fund. Our contact there is Dale Tingley. He's been on our board since 2020. They actually invested in us the months that COVID happened, so we had been talking to them, we had been working on a deal and they had every reason to pull out in March of 2020 because everybody was just freezing.

Speaker 2: 16:44

The world was on fire. Nobody knew what was going to happen. They still went to bat for us. They still said we see it in you guys. We think well good, so they saved our asses there. They went to bat for us and we've seen that ever since. Canadian Business Growth Fund is all about patient capital. That's kind of their tagline. If you will, you find a great investor and then you still are going to go through hard times. They're really there to challenge the CEO, not try to destroy the CEO or get them off the board or whatever it happens to be Fire them. It's challenge the vision, challenge the strategy, ask really good questions, but also there for moral support and if you can get that balance right, you've got a great board.

Speaker 1: 17:33

Yeah, and so that relationship is really hard to build. It's something I've spent a little bit more time on. When I reflect back, it was really the investors where I had a friendship. I could text them if they were a buddy on a Saturday and get a reply back within an hour. And so what's your advice for building that relationship over time, and what role do we play in leading with value back to investors too, so that we're not just in a position of always asking for help?

Speaker 2: 18:04

So I experienced this on a very, very small scale in terms of I've invested small checks in companies that I still am either serving on the board or as an advisor, and so I get to see it a little bit from both sides, or I get to play the board member, investor, hat some areas, and then I've got my board and I would say the ones that you really want to go to bat for as an investor are the ones that tell you everything. So they send you monthly updates At board meetings. They're transparent. They essentially ask for thoughts, advice, questions when they're making big, important decisions, even if they're not contractually obligated to. Sometimes that includes taking on additional capital debt, sometimes it includes removing or hiring an executive manager.

Speaker 2: 18:58

Just asking their opinion for those things goes a long way to building trust, because if you're a cowboy or a cowgirl who just kind of does your own thing and doesn't give a crap about them, then when you need them they're going to be like I know you're just going to do your own thing anyway. So maybe at that point you want to, as an investor, as a board member, you want to like step off the board or not, put in for the next round or not make an intro to an investor the next time they're raised. So I tried to, with my board, be very transparent and even tell them when I feel like I don't know what to do. You do have to balance that a bit right, because at a board meeting, the CEO is there to say like here's, I have a plan, this is what we're going to do. What's your opinion? Challenge me, tell me where I'm going wrong. But if you come back too many times and go like I don't know what I'm doing, then they'll lose confidence.

Speaker 1: 19:55

Got it and I guess, like when you think about the board and going through a crisis, what strategies have you leveraged to put them to work no pun intended, because they've already really put their money to work, but to help resolve it, like getting them involved, putting you know, facetime in with the team and things like that. Have you tried that or seen that work in other companies?

Speaker 2: 20:20

Yeah, I mean my board doesn't talk to the overall company a lot. Okay, I mean I'm not a executive team at board meetings but they don't spend a lot of time. You know interfacing with a broader company. But I would say you know the board meeting and sometimes you need to increase the frequency of that more than every quarter if you're going through a really critical time. So maybe it's a monthly call instead of a quarterly.

Speaker 2: 20:44

You know, on top of the quarterly board meeting and we've done that before you know it really depends on what you need, like, obviously, if you need to raise capital and they aren't going to, you know, go all in and they want another investor at the table, then you know, clearly they can make some introductions and bring people to the table. Sometimes it's customers, it's you know, hey, we need to fill our pipeline. Do you know anybody I've had, you know, one of my portfolio companies ask me for that. But a lot of times it's just the support, the guidance, the. You know it's not a tangible, they're going to go to work for you, but it's just hearing you out, listening, asking questions, giving you some advice. That is worth its weight in gold, got it?

Speaker 1: 21:33

And so I guess, if there was like one piece of advice that you would have given your younger self after reflecting, through all of the chaos that you went through, what was the one thing that you really had to work on? Well, when you had mastered that or improved that skill so that you felt you were in a good place with it, it really had an impact on your company, your team, your revenue. Maybe think of it as like a leveling up moment as a leader, but triggered through chaos.

Speaker 2: 22:07

I think it's about being able to make the call even when you don't have all of the answers or all the data. So I remember when I was reading Obama's one of his like his latest book, I think it's called Promise Land where he said that every decision that he was faced with when he was in office was a decision where they only had maybe at best, 30 or 40% of the required data to make that decision. And if they had had 100% of the data and it was essentially an easy decision to make it wouldn't have come to him because his job was not to make those decisions Other people can make those. His job was to make the tough ones where you couldn't 100% prove you were right. You had to use your gut, use your intuition, get advice, get broad advice, but make the call. And I thought that was really interesting as thinking of it as a president If that's true, the president's, it's true on a smaller scale, as a company leader.

Speaker 2: 23:07

Just like strategic decisions are not guarantees, they are a leaps of faith and your team doesn't always understand that they go well. You know how do we know you're right? We don't know, but here's, here's framework that we've used and to make that decision and then it's come to two or three choices and I'm going there. That's it's better to make the decision and be wrong than to not make the decision, because not making the decision is a decision in and of itself.

Speaker 1: 23:37

That's very true. So we've talked a lot about like the company side of chaos, but then there's like the personal side too, and so in our chats I got to meet one of your, one of your lovely children, who's full of energy and laughter and excitement. But, yeah, so for those that have families, that are founders and entrepreneurs, what's a day in the life of you look like from from the family side, if you're open to sharing it, and how do you keep all of that sane?

Speaker 2: 24:08

Well, starting the company it was, my family life looked very different, you know, when proposed I was just getting off the ground and even pre product market fit. I was going through divorce from my first wife, had two kids that are older now, and was kind of, you know, as the primary parent. I was, you know, holed up in an apartment with them on my laptop trying to, you know, trying to get stuff done while that was happening, Like though that was a hairy time. Things are substantially easier now. You know I have a lovely wife. You know we've got two, two young ones, in addition to my older boys, and we're also in the position now to be, to have a nanny and to have some support.

Speaker 2: 24:49

So, so no, I mean, things are, things are great now, but, yes, it's, it's, I don't know, it depends who you are. I guess, like having kids can, can be difficult to build a company. Making time for them, not shutting them out I haven't. I haven't had that problem per se. I'm pretty good about. You know, evenings are family time, weekends are family time. I think it, just as a company grows, you start to build a little bit more normalcy and not just go on percent all the time but it but for some. They really struggle with that.

Speaker 1: 25:25

Yeah, I think it's. You know, again, it's just the byproduct of being so enamored by the problem that you're solving and all the people that rely on you and in the balancing act. It's been an area I've been giving a lot of reflection to as I think about kids, would love to have them and can't wait. But yeah, I look through my best friends and see their worlds and how they've changed. And so you know, basically what I'm hearing is you know, even amidst all the challenges with raising kids and building a, you know, a personal life, you know it is still possible to build a company. It's going to be different for everyone.

Speaker 1: 26:05

Is basically what I've gathered from you, and it's really about just finding your rhythm and your cadence with your partner. How do you make a decision if you've got two competing priorities, like? I know as basic as that sounds and this is not to open up a therapy session, but you know as basic as it is. You know like I had to work on the weekend and I remember telling my partner and her responses this is going to cost you and sending me a trip. But you know that was humorous and over time she's come to understand it. But yeah, what advice do you have?

Speaker 2: 26:41

So we're talking on the personal side, like yeah, yeah, I don't know like my wife and I are, we're both working professionals, but a very different you know, arenas. She's, she's in healthcare, she's a physician. It's funny because she doesn't. You know, I think for a lot of people who work kind of quote, unquote, normal jobs, when you work from home, when you're building a tech company, it can kind of be like oh well, you're, you know you're free all the time, you're, you can go pick up kids or you can go get dinner started.

Speaker 2: 27:11

And it's sometimes hard to, you know, make it clear like it's the like I wouldn't go to the hospital and hand the baby to Christina while she's seeing a patient. But sometimes they don't understand. Like just because you're not on a work call doesn't mean you're not working, and just because you're called doesn't mean you're available. So that can, that can be tough. But yeah, I mean, I think one of the best decisions you can make in life in general, life in general, is choosing who your partner is, who your life partner is, and you make a bad decision and I've made a bad decision in the past you will have a miserable life. So if you can find somebody who you can work with, who you can, you know, you can align your calendars and you can really treat each other as equal parties, then life's going to be a lot easier.

Speaker 1: 27:58

What's your wife's superhuman power?

Speaker 2: 28:01

Oh, well, she has many. She is a great.

Speaker 2: 28:05

You've got to get her to hear that, by the way, I will be sharing this with you, one of the many things that Christina does well is she's very great at planning and especially I can get very much in my head and very focused on work and the business and I and it lights me up. So it's kind of what I'm mostly obsessed with other than music. She's great at like planning trips, planning family outings and sequencing it and booking it and making sure and just making sure the whole family has a good, good time. So I feel like I wouldn't do as many cool things if she wasn't around, because she this is what lights her up and she enjoys doing it.

Speaker 1: 28:47

But I'm smiling ear to ear because you literally described my human as well. I'm the same and I've had so many amazing experiences because of the time that she's taken out her day to playing cool things for us. And so when we're talking about partners, there's the other side of it, which is you know those that we're going to go and build these ambitious businesses with and you know what you know. It sounds like you and your partner. For the most part, you guys have been quite successful together. But you know, what advice would you give other founders, or you know even the founding team of like what do we need to look for in a partner that we're going to build a business with?

Speaker 2: 29:31

A business partner is not that much unlike a marriage or a long term commit relationship, right it's. I've been partners with Kevin now since 08. So that's well over 15, 15 years or so, actually it was about 15 years. So you know, across two businesses both, you know we've gone through hard times. Our agency, I mean we were, you know, many times an inch away from bankruptcy or not being able to make payroll, and you know really, really tough times.

Speaker 1: 29:59

So those are the types Sorry to cut you off, kyle. That's the epic stories I'm talking about. We'll come back to that, because how do you get through those times where you can't make payroll and things like that? But we'll circle back to that. I'll let you finish, sure, yeah.

Speaker 2: 30:12

I think, and the thing is, you know, it's because we're humans and because we're wired differently and we don't always see the world the same way. You know you're going to have disagreements and resentment can build pretty easily, especially if you have different goals, and Kevin and I have. You know we've had those discussions around like he's going to be 16 next year, right, I just turned 40. So we have a 20 year age difference and I want to keep building and keep going and do cool things and he's kind of at the stage in life where he wants to retire and he wants to sail off literally in a boat into the sunset. So sometimes those two goals don't align. So we've had to.

Speaker 2: 30:54

He's taken a step aside. He's, you know, we've hired a COO and a CFO and we have ahead of sale, so he's not as involved in the day to day with the businesses used to be. We've figured out a way to make that work and I think that you know I've observed co-founder drama, where they're they're beating their heads against the wall and it can destroy the company if you let it. Oh yeah, you can have a great company that gets just set on fire because of the co-founder drama, and that's just something we never wanted.

Speaker 1: 31:30

How do you keep it in check? Because emotions and logic conflict and you get a whole bunch of people that are emotional, right, and so did you have any practical strategies or things you used? I'll give you an example. Mine was always like grounding it, and I have the honor of working with my two best friends that I've known for over two plus decades, and so it's a rare experience in life coupled with you. Know these people the best right? Many say it doesn't work, but just grounded in the outcome is my advice. You know what needle are you moving, what impact has it made and what can we do to make it improve it? Yeah, and just keep on coming back to that. So that's mine, but I'd love to learn yours, if you have any.

Speaker 2: 32:12

Well, you know you like those people, you enjoy their company. So I think you know sometimes people choose. It's like the marriage right, it's an important decision on who you choose, because you can set yourself up for a life of happiness or a life of hurt. And sometimes co-founders choose each other without that bond, without that friendship, like marrying somebody that you're not actually friends with, you don't actually enjoy their company. So then when you have disagreements, you know you can. If you're in a healthy relationship, you can say like, hey, I'm really pissed off what you did upside me, or we don't see things the same way, but ultimately we like each other and we want to maintain our relationship. That doesn't always happen in unhealthy co-founder relationships, just like it doesn't happen in marriage, where it's just war and one person is going to win and one person is going to lose.

Speaker 1: 33:04

Yeah, but it's funny, like being able to call people out specifically your partners on things, but do it in fun and playful ways. That's definitely something that we've done in the past. That's helped. And then the other piece of advice I would give is give it time. Like give it a night right when if you're triggered and you know you're triggered and you can catch it, give it time. And even if it's not the best representation during that situation, a night's sleep can make a big difference on that relationship.

Speaker 2: 33:37

But to your point they had a whole positive intent. Yeah, two positive intent. You're right. I sent Kevin a message, I think, two weeks ago. He wrote something on Slack and I private messaged him and I said I don't think you meant it this way, but that kind of pissed me off and here's why. But I all prefaced it with like hey, how was your travel? Hope you're well. But I'm sure you meant something different. And I find, and he was like oh no, I'm sorry, I didn't mean that that way, but I think that that's just conflict resolution. But it works with employees, it works with your spouse. It's just to always assume positive intent. So start with when you did this thing that we all re-happened. This is my interpretation. I'm sure I'm wrong, but this is how it felt to me and I've made that little tweak in how I communicate to employees, to board members, to whoever, and it's been completely changed, because everybody starts with the assumption Everybody starts with. You must think I'm an idiot. Well, no, that's your interpretation. That's not what they actually said.

Speaker 1: 34:43

That's yeah, 100%. We're worried about what others are thinking of us more so than they are. We spent a lot of time in our heads as humans. But I guess my next question is around you know, for those who are starting a business, looking for a founder, what's your advice for finding one? Like, where do you find them? It's not like you can put it a job at if you're just starting out and looking for that critical person that you'll go to battle with to build something.

Speaker 2: 35:14

So I only have data point of one, which is Kevin. I've never had any other business partner. We were colleagues for a year. We worked together. I was a designer, he was in sales. We worked sometimes directly, but often just in the same office, grabbed coffees together, saw the world very similarly. Even though there was a lot of opposites, there was also a lot of crossover. Again, I keep using the marriage analogy. But it's like, yeah, you're not going to marry. You don't go like, hey, would you like to get married one day. You go and you meet people, and then some people you click with and you tell them your ideas and they have ideas too and oh, this is a cool thing, I would love to do this. And then you start doing it together and then maybe eventually you formalize it into a real partnership or rush into it, because you don't really know what people are like to work with until you actually work with them.

Speaker 1: 36:07

The questions that I always ask myself when in those situations even with clients or potential clients or partners is like if I was stuck in a three hour traffic jam with them, would that be the person I'd want to be stuck in a traffic jam with for that amount of time and would I enjoy the conversation? Right? Because, again, there's no exit. You're just there with that person until the traffic starts to move, and so that's obviously one of those situations that no one loves to be in, but that's been helpful. The other things that I've seen really work well is there's like entrepreneur first and some great accelerators that have come together that are trying to help combine the business led founder with the technical led founder, and I think that's another important element to consider is like really know your strengths really well. Don't be afraid to call out what you're not good at and then find that in the person that you're going to build your business with.

Speaker 1: 37:13

I think that obviously is coming. I'm 41 now, so if you ask me this question at 20, it'd be a very different answer, but I think my core skills probably just increased. They haven't changed. Maybe I've learned some new skills, but yeah, so on that note alone. I guess, closing things off, has there been one book that you've read that got you through one of those moments of chaos that you'd like to share with us as a point of inspiration or something to leave everyone with for when they face their next challenge?

Speaker 2: 37:49

I like that you created some guardrails with that question, because if you ask people their favorite book, it's like well, if you read 20, 30 a year, then it's exactly. There's really great books, but specifically one that helps you through hard times as a founder. I can't think of any book other than the Hard Thing About Hard Things by Ben.

Speaker 1: 38:07

Holtz oh, I love that book. That's such a great book. I love it.

Speaker 2: 38:11

It's almost a reference book more than one. You sit in, you can read it through front to back, but it's really more about picking the chapter for the thing you're going through right now. So I always tell people, if you see the Hard Thing About Hard Things on my desk, shit's about to get real, because the chapters are demoting a loyal friend, preparing for layoffs or firing an executive, or dealing with zero bank ballots or a little money Just all the horrible stuff that you are going to go through as a founder. It's in there, ben shares, actually, in a lot of cases, many worse things than we will ever deal with. Or at least on a point, oh yeah.

Speaker 1: 38:55

Oh yeah, I mean, that's one of the books I can vividly remember, clinging to every page. But the cool thing I got from that book was not only some practical tips and ways to deal with these situations, but it also helped me learn about myself, because, as he was talking about members on his team that he had built and tried to bring in to help unlock the next round of growth, for example, or whatever it was, you start to identify and seeing yourself. He has an excellent way of really getting across the people that he had built his companies with and the importance of those people and their skills and how to go and find them. So that book's a great one. Another one for me is Zero to One.

Speaker 2: 39:38

Yeah, yeah I really like that.

Speaker 1: 39:40

You get to see all of the different stages of evolution in a company, the challenges that they face and some of the individual heroics that are needed to pull off these impossible feats when you enter them, and then the final piece, so reading, obviously, we know if you read for seven minutes, it's more therapeutic than most things that we do to manage our stress or recovery. And you mentioned that you're a musician, and so I want to close on this. We share this in common, and the question I got asked once when I was on a podcast, which made me think, was how did music help shape me as a business leader? What did I learn from it? And so I posed that question to you, and your face just gave the same response that mine gave when I was asked that question. So, not to put you on the spot, but maybe I'll let you think and I'll give you one that I got, unless you're ready to go. No, let's hear yours, yeah, okay, I'll give you some time.

Speaker 1: 40:38

The biggest one was it taught me to run a business without even realizing I was running a business, and, and so my first gig was at at 17, with with 11 spoonful at cops Coliseum, fully packed stage and I remember telling the story and every time I do I say, like you pay me up front and that like that simple lesson of like when I started my first company. Like you don't do work until you get a check, like it's those basic lessons. But I laugh now. But I wouldn't have known, right, like unless it was me personally and and needing the money, I mean I may have treated that differently if it was company money.

Speaker 2: 41:17

Yeah, well. So I think that, if you know, for you it's different because you were, you were much more of a professional musician yeah, whereas I never was. Like I, you know, played guitar in a band in high school. Yeah, in an all-ages show and we recorded an album and stuff. But, like I, was never that serious about it. So I don't have any direct like oh, I learned how to manage cash better or whatever.

Speaker 2: 41:40

Yeah, having started a band about a year and a half ago and Group, you know, produced an album, self produced an album, played a few shows. What's funny is that a lot of us in the band all have business background, so we're almost running it more. You know, we run a tight ship. We're pretty productive. We have assigned roles. We get stuff done, probably more than maybe a younger band would do, so I'd say almost more. So the business has informed the musician side. Oh cool. So it's it's. It's tough, you know.

Speaker 2: 42:10

But I think also too like, so I never read music. I didn't take lessons, I was all self taught. I'll played by ear, I pick out song and figure them out, but I couldn't talk the music theory, lingo, stuff. But I think was during COVID, I bought some courses and started following YouTube channels and I was like I really want to understand this, like I want to read sheet music or I want to talk about you know Up extensions and ad nine chords and things that I'm just like I kind of know where to put your fingers, but I couldn't describe why it's an ad nine or a you know seventh word or whatever. So I actually went deep on that and like now I'm pretty fluent in it and so I think that's like one of the things of Same with business. If you're not good at marketing, if you're not good at sales, it's like Okay, not now, but you can educate yourself. You can pick up a book, you can take a course and you can get good at it.

Speaker 1: 43:00

Right, so what I'm, what I'm hearing, is continuous learning that that music has been one of those muses for you to really keep that muscle and and I mean to be honest, that's one of the key skills to navigate chaos. The more knowledge you have, the more Situations and stories that you can pull on from things you've read, people you've talked to, the more equipped you're gonna be. And so you know, kyle was great having you on the on the show today. I think we can walk away with a few more tips and and strategies and approaches to to manage the, the stress that comes from being in these, these moments of chaos and my. My final question before we conclude things is what's your one piece of advice for when things are calm?

Speaker 2: 43:48

Great question. I mean I haven't read the book, but I know the person who made Ohio put management, andy Grove, wrote only the paranoid survive. So even just the title of that book, I think, is a good mantra for founders when things are going well, when you're growing, when your team's happy, when your customers are happy, don't take your foot off the gas. When you could make payroll, yeah, exactly yeah, just don't take your foot off the gas.

Speaker 2: 44:16

There's always you know, in Hard thing about hard things, and Horowitz talks about peacetime, wartime CEOs and how they're different. Wartime CEOs very clear, right, it's do what it takes to survive, make the hard calls. Be ruthless, you ruthlessly decisive Peace time CEOs a little different you can. You can, you know, think about hey, let's get into this new opening, this new market, let's try these new things. But don't get comfortable. And I, you know, if you're the I've known founders who've like Gone to Bali for six months as soon as they've gotten cash in the bank and it's Never goes well. Yeah, yeah, I'm driving it.

Speaker 1: 44:59

My mantra is quick cash never lasts long and cash that sits there is also gone in in no time. So that's a great way to ground yourself and and not get distracted during the calm moments is knowing that it won't always be there. So yeah again. Thank you, kyle, so much for being on the show. We'll be cheering you on and rooting you on the sidelines for your your next round of growth and success with your company. Yeah, all the best, my friend. Thanks, jason.

Speaker 2: 45:24

Appreciate you having me.