Endless mistakes can be made when starting a new business. From being unable to let go of the reins and getting in his or her own way to making the wrong hiring decisions during crucial growth periods – new company founders tend to feel like treading water is the name of the entrepreneurial game.
How can founders ensure that they aren’t on the path to failure before they even begin gaining traction?
The answer is simple. Learn from those who have turned their failures and mistakes into unwavering success.
In this special episode of Evolved Sales Live, host Jonathan Fischer sits down with a panel of veteran business owners to teach new founders how to elevate their business from the inside out.
Don't forget to follow us on LinkedIn for more engaging sales insights and discussions! Happy watching!
Meet the Panelists:
James Chapman: Founder and CEO of Plain Sight and Workaholics
Kris Rudeegraap: CEO and Co-Founder of Sendoso
Lavie Popack: CEO and Co-Founder of Overpass and CEO and Founder of MPower Energy
Check out the transcription of this webinar episode below!
Jonathan Fischer 0:04
It's time for another episode of Evolve sales live. Welcome back. I'm Jonathan Fisher, your host. Well, it's an exciting time to be a company founder. And it's no secret that many of this shows listeners are either company founders, or have a key role in the startup of some kind. When new companies succeed, it makes the headlines, but some of the best insights can be had from the failures and mistakes that led to that success. Today we're going to explore some of those insights with a panel of highly successful company founders. Joining us from the Big Apple is Lavie Popack, founder of overpass.com overpass is unique solution for hiring pre vetted remote talent very quickly and affordably. Hiring Managers can open a free account, view profile CVS, listen to voice samples and filter by industry and experience. Overpass makes it possible to interview hire and begin onboarding process in a matter of days instead of weeks. Next up on our panel is is Kris Rudeegraap. coming to us from San Francisco. Kris Rudeegraap is the CEO and co founder of sendoso.com. Sendoso helps companies stand out by giving them new ways to engage with customers throughout the buyers journey. They're backed by 152 million venture funding, they've got a global footprint with the presence in North America, Europe, and Asia Pacific. And coming to us from Motor City is James Chapman. James is the founder of the networking at plain sight dot plain sight takes the work out of networking business, people can find upcoming events, remote spaces to work and make new connections based on mutual interest. Connections are curated and made online or in person based on their individual skills, goals, interests and professions. Hey, all of you, gentlemen, fantastic to have you on the panel. We're excited to do our very first panel discussion, remote sales wive. A live Welcome to you.
Lavie Popack 1:59
Thank you, Jonathan. Appreciate it.
James Chapman 2:01
Thanks for having me.
Jonathan Fischer 2:03
All right. So we we'd pulled each of our panelists ahead of today's show to hear what were some of the key mistakes, what are some of the key things to not do when founding a business. And they broke down into into some subject areas. And so just kind of leading off with in no particular order. There are a lot of mistakes you can make when it comes to bringing in the first initial hires into your company hiring errors as it was a big theme. And so maybe we can kind of sound off. One of you gentlemen, just trying to kind of chime in here. What are some of the mistakes you personally made? In terms of hiring.
James Chapman 2:42
I can kick this one off. I think when it comes to hiring, we usually hire people that we like, right? That we feel like we can relate to maybe even trust. And that makes firing them much harder. Because you've hired somebody because they're qualified and you'd like them initially. And so when you start to realize that they aren't quite a fit, you tend to try to hold on to them longer than you probably should think about it just like a romantic relationship, right? Like you build all these things with this person. But you, you find out at some point, and it's usually about after about three months that like oh my god, I don't like the first red flag usually pops up about three months and voc business and, and personal relationships, you know, romantic relationships. Yeah, and I just think it's a habit for some founders, especially in the early stages to hold on to those people too long. But the thing about it is that can be very business critical, because every single person matters when you're a small team. And you can't hide. Right. And so the other teammates are also going to notice at some point that this is a person who probably shouldn't be on on the team. And so I've got stories for sure on on, you know, hiring people who just aren't a fit. I think we all do. But But I think the lesson to be learned there is the timing on the firing piece. And the separation.
Jonathan Fischer 4:10
Makes a lot of sense. James, I saw Chris nodding his head knowing Yeah,
Kris Rudeegraap 4:14
I can relate to that, too. And just, I think like James said, it's often easier to hire people, you know, in the early days, and sometimes it's way better to go out and spend the extra effort recruiting people. And so the relationship starts off on the right, but yeah, I had a couple of things to add to that, though. One is related to when you're going out in hiring your first STR AE I think the tendency is to kind of crawl before you run and maybe just hire one person. But you know, you can often have some bias there where if you hire the bad first sales rep, you're not you might not be sure if it's whether the sales reps actually bad or if like the product market fit and your go to market motion is bad. And so I always recommend now to And early stage entrepreneurs and founders to hire in pairs, whether that's two STRS, or two A's. And so one they can, they can learn from each other compete against each other, because sales is oftentimes better when you're competing. But then you can also learn to and make sure that you're not having an individual that creates a bias for your product market fit.
Jonathan Fischer 5:21
Yeah, for sure. I think it's a great insight to hire two people. Would you unpack that further, Chris? Like, what are some of the advantages of hiring them in pairs?
Kris Rudeegraap 5:28
Yeah, well, aside from the competitive nature of hiring and pairs, and being able to understand the bias of one person doing bad and the other person doing good, and so you can really understand better that way. You also can help build out your enablement or your training in the early days, too. So get people to start at the same time and make sure that they're off to the races at the same time to
Jonathan Fischer 5:53
love that. Maybe you're splitting your risk a little bit too, right, you need that function filled, at least you'll have the one person a little more likely than, you know, instead of being Pass Fail. Levy, what are some of your insights in this area, you've been hiring people, and that's actually what overpass does is help, please, hi.
Lavie Popack 6:09
It's funny, when Chris brought that up, I know you weren't, like, you know, trained into like saying that, or prior to getting onto this call or onto this, me, but that's exactly what we tell our clients, it's you want to hire in pairs, you want to also reduce on that risk. So like you said, you know, one person doesn't work out and you know, at least you still took the time and, you know, you're you need to take that time upfront to invest and train people properly when you bring them on. And I think that's where a lot of people fail, is thinking that they're going to bring on salespeople and not invest in them and not invest in them upfront. And then if you don't, and invest, obviously, you know, it's, you know, it's, there's problems that come along with that. But if but, so you need to invest, but then when you're going to invest, you want to invest with more than one person with multiple people. So that way, you know, you're, you're training a full team. And then there's also like, collaboration around that. And you could really, you know, get moving in that way. But one other thing I want to add and something that, you know, I personally went through starting on Power Energy prior to get a starting up overpass is getting in, I think a lot of founders go through this. If you went to a company and you think about what's going to happen, what are the needs that are coming up? That what is this company gonna look like? What are the different departments within the company, and then you start hiring for what you think is going to happen for the problems that you think you're going to experience. And you end up hiring way too quick. And you have people just sitting around not doing very much. So but then on the other hand, you have lots of problems and challenges that pile on and now you're having to like divvy out these different tasks or challenges to the few people that you do have an accompany. So it's a fine balance between, you know, the need to challenge a problem, you know, and filling it with, you know, with the right employees. So I think early on, that's definitely something that a lot of founders a lot of startups go through. So especially like, when you have tons of capital coming your way, like I have all this money now, I we need to build out all these different departments, because we're gonna have all these different needs. And now you have money to throw at it. So you got to just be like very reluctant in doing that.
Kris Rudeegraap 8:39
Yeah. One thing I'd say on top of that, too, on the other side of that is if you can't afford to hire two people, or you're not sure, who's the next person to hire, I would say don't hesitate to use like Upwork or freelancers as much as possible, so that you can still make sure that you don't hire somebody, and they don't have anything to do. So I think as an early stage founder, you know, Upwork can be your your best friend.
James Chapman 9:06
Yeah. I agree with that. And then it also allows you good, yeah, sure. You got a James? Oh, no, I was I was just gonna say it gives you the opportunity to try them out too, right. Like when you onboard somebody initially through contract as opposed to just bringing them on full time, you know, right out of the gate. You can work with them a little bit, give them a little bit more flexibility. See how you both work together. And then it's much easier to support ways if need be but but that's the only thing I was gonna
Lavie Popack 9:35
Yeah. Yeah, I totally agree. I think for developers and copywriters, and designers of that nature. I definitely agree with you on that, Chris. I find that you know, when it comes to salespeople, a lot of our clients actually come to us specifically for that reason because they want to kind of test things on and pilot it and without like putting in too much risk at the same time though. You have to ensure you train them properly. Really, so if you're gonna come in and be like, okay, maybe I want to hire for 10 hours a week or 20 hours a week and test test out the waters and things go really well then you know, we're gonna scale it up. So yeah, you definitely have that ability to do that when you're working with a remote model when you're working with like, a sales talent marketplace.
Jonathan Fischer 10:20
Yeah, really good input. Guys. Back to the earlier note to of not necessarily hiring friends and family had nice comment from the the audience today, come on, man have a family like that's what you hear from people, right? They want to get a job because they know you. And the gentleman here, Michael made the comment closeness breeds contempt. It's kind of harsh. But I think it's a very real thing, you're seeing a certain side of folks that are in your personal circle. And you're rarely going to be able to, to, in an objective way, vet them properly to bring them into your company. I've seen this even with partnerships, where it does not working out well at all, Chris, yeah, I think you broke a rule in that, right? You partnered up with a friend and it worked out. But
Kris Rudeegraap 11:01
I will say that one other thing is, you know, when you're a very young founder use, or maybe you're graduating from college, and like I want to start a company right now, I do think there is some advantages to going out the workforce working at other companies and building a network. Maybe they're not your best friends, but you have colleagues that you've worked with before that you can hit up for, for roles. And so that was similar to my story where I spent about eight years working in other companies. And when I went to start Sindo. So you know, our first sales rep came from the last company I worked at, and we were friends per se, we weren't like besties. But we became more friends as we work together. But it was easy to have that network to pull from. And so I think some entrepreneurs are antsy right out the gate right after college, say I need to start something right now. But there is some advantages to building your network, in the professional career that you can then use for a hiring pool, when you do start a company.
Jonathan Fischer 11:55
That makes so much sense because now you're not basing it on the Friendship first, it's actually more of an actual curated network. So you're actually seeing what they can do in the workplace. Now, that makes sense. James, you want to chat in there?
James Chapman 12:08
Yeah, I was gonna add something to what Kristin on even the fundraising side of things, right? I think it can be a good idea to go and work at a VC or at a venture studio or something of that nature. So that you can really get a good understanding of the jargon, what investors are looking for. And you get a chance to see some of these other deals and things of that nature. That that has worked out very well. For me, being able to work with Dan Gilbert's family office in the past, I've just learned all of the things about BC and investing before actually jumping out there to start my own thing and building those relationships and network at the same time.
Jonathan Fischer 12:43
You Yeah, I love that. James, if I could, I want to go ahead and take that as a segue and move to the next common theme that came in the polling. And that is sort of your personal development as a leader, as a founder, you go through your own series of stages and development as you're, as you're growing your company. And I know some of the lessons learned come from that series of lessons learned and then applied. So maybe we can kind of go through that what how have you had to change as a company founder. And we have an interesting spread here, because we've got, we've got lady who's actually founded a couple of different companies, and probably has a little bit longer tenure than Chris is kind of in the middle. And James is kind of newer. So each of you are right on the panel, a little different stage of the game. So maybe we could kind of start with our senior sorry, to levy member of the team in that regard, and share some of the lessons you've learned and how you've had to maybe modify and grow as a leader, or maybe some specific errors that you made early on, in your management of your company.
Lavie Popack 13:38
Yeah, sure. Yeah, just before we jump in that, but I have one of my best friends, and I have two of my brother in law's work with me between them parent Overpass, and I love them. They're great. It's been nothing but amazing. So I definitely think you have to be very cautious in who you select in terms of like family and friends. But I do think that it can work out really well.
Jonathan Fischer 14:02
You just have a better set of family and friends. That's what that tells us right now.
Lavie Popack 14:07
But yeah, yeah. So personal development. I mean, where do I begin? Right? So, I would say a couple of things. First of all, like I've learned to learn, I've learned to think about like, what is the biggest pain point that like, is keeping me up at night. Because I think the issue is not so much a matter of solving the problem. It's about knowing what the problem is. And there's so many things coming at you at one time throughout the day. Nonstop. So when you you know take a few moments. Meditate I mean, I would love to get I don't meditate much but I should meditate. But like meditate a little bit upon like what is that like top level challenge or problem that like kind of lingering for a while, maybe weeks, maybe months but like You haven't really been doing much about it. And then and then hone in on that and explore it. And when I say explored, I mean, learn, like, pick up a book, podcast, whatever it might be, and just master that specific niche area of that challenge. So it might be even a podcast, right? Like, you know, go to market strategy. Yes, I want to develop a podcast or a live event or community, like, what do I know about communities? What do I know about podcasts? Well, there's tons and tons of content out there, you spend a couple of weeks, you know, uncover as much as you can, and then start and then you bring in some of the subject matter experts, some of the consultants that could that you then work together with, you don't just hire without really knowing much yourself. So that's one area that you know, I've I've been working on for a couple years now is just really honing in on my error, personally, Arab weakness that kind of connects with the biggest problem that I'm experiencing at the time. So you know, earlier on, I was actually marketing, because my background, Well originally is from from real estate, then from real estate, I entered into the energy business, in the energy, retail energy business, it's the old school way of selling, which is door knock. And door knocking is the furthest thing from like, brand awareness, right? From like, from like, marketing. So like, so I'm thinking, I'm going to come in to build a tech company, I'm going to knock on people's doors physically, that's not going to happen. Right? So so now you have to understand like, Okay, what is going to happen? What should that go to market strategy be? So you now have to pick up, you know, that discipline to understand, you know, the different areas of facets of Product Marketing, and brand marketing and awareness and content strategy, and podcast and community and all these amazing things that, you know, 20 years ago, they didn't really have much of any of that. So, you know, and that's really like, I'm essentially even though like, Yes, I'm officially my title, CEO, but like, 90% of my time, I deal I work in marketing, and sales as well. But I would say more on the marketing side, so and some because I love it, I actually got to enjoy it. But it's more because that's what the need is, and what it was that I have to master in order for the company to take off and move.
Jonathan Fischer 17:27
I think it's a common theme in many of the more successful companies out there. And even some of the company turnarounds is because, you know, the the head took that bull by the horns. So, Chief learner, one of the hats that you should be wearing sounds like, lady, what are some additional lessons that you've learned, Chris, in your growth of your startup over these last half dozen years or so?
Kris Rudeegraap 17:48
Yeah, so I'd say a couple things. One is, you know, in the early days of founding, founding the company, as like the co founder, you know, you're helping everyone everyone kind of knows you. But once you get hundreds and hundreds of employees, I think employees can start getting intimidated by the CEO at times. And so I've had to change the way I've acted a bit because just popping on a calendar invite over to another employee, when we have 500 employees, and they've never met me, can come across a bit different. And so I've had to kind of change the way that I interact with other employees, to still keep my very hands on mentality. As I like to get in the weeds, I like to, you know, make myself available to everyone, anyone at the company. And so I think that's something important is how you're perceived as the CEO as you grow from a small seed stage company into a Series C and beyond. So that's one thing. I also think like, as the founder, you kind of are the culture of the company. And so you have to be very apparent in what you do and what you don't do. And you're very much a public figure to the company all the time. And so I think you have to be like overly aware of that, and make sure that your actions are leading to the company culture that you want to build. I think that's important too. I
Jonathan Fischer 19:10
love that. Yeah. I love that Chris, it takes a lot of commitment on your part as well as the head you have to really see that as core to your own mission and act on that on sounds like in your case a daily basis so that's that's admirable admirable, by the way. James rotating to you so your, your earliest on in your, in your journey as a founder? What are some early lessons that you have learned?
James Chapman 19:32
Get the hell out of the way of my team? Like, like, that's been one of the biggest things that I've struggled with. I mean, just to be completely honest with it, right? Like I can be a bottleneck. But it's my baby and I'm passionate about and I love it, and I'm breathing it right and all of the things and my way is not always the best way. Oftentimes My way is not the best way. And I think that just being able to let go as As a founder and as a CEO, so that your team can be able to have ownership over everything that you all are doing. Because at the end of the day, the business is only going to go as far as the team, right? Like we, as the leaders of these businesses, we have the vision, we're going to be able to get the directions and things of that nature and keep everybody on on track and be the ones who are going to decide how time is being spent and how money is being spent. But at the end of the day, your team is the one who's actually out there doing it. And so that's been the biggest and the most challenging lesson for me, it's just get out of the way, trust your team, don't feel like you have to oversee every single thing. Like, those are some of the challenges that I've had. And I've seen myself grow in those areas, and just being more transparent with my team and, and allowing them to own things and allowing them to make mistakes and understanding that it's okay, if they if they make you know, certain mistakes that I would not have made, had I done it right that like it has to be some type of to direct the read their with their progress, and you have to allow for that.
Jonathan Fischer 21:03
Yeah, I love that. That sounds like a pretty oppression insight for you to have this early on in the growth of your company. What are some of the key ways to all the panelists that a CEO can actually get in their own way? I think that's a great topic.
Kris Rudeegraap 21:19
Yeah, I'll kick it off there. One of the areas that I think in the early stage as it relates to sales is, I think founders can, you know, founder led sales can last too long, and you can overly focus on, I'm going to keep doing sales, I don't need to hire people. And you can see some really false positives with product market fit. So my suggestion is, instead Hire Sales ASAP to ensure you have a good go to market fit, because I think that passion of a founder can be harder to replicate with a stranger. So and I think that goes with other roles, too. We're in the early stage, you try to do too many things. And back to Jamie's point, just get the heck out of the way. And you've hired smart people to do things and let them do their work, their best work.
Jonathan Fischer 22:04
Yeah good stuff stuff Kris.
Lavie Popack 22:07
Yeah, I totally agree with that. And then in addition, as I was saying before, you kind of like, don't want to hire prematurely. So you kind of step into that role yourself initially. So like, for right now, for me, a lot of it's on the marketing side. So and then I think, you know, we could tend to just stay in that role too long. So you know, the process I see is like, move into it, Master and make sure it's like a well oiled machine, then move out of it, and let the right person move in. And I'm sure they could do a better job than I can. So you want to I see that as a great system, a great process, but you don't want to be in that doing that too long. And I find myself personally that I have done things have done that too long, or I've stayed in those those roles too long. But it's also an emotional attachment. You know, you're in it, you're doing it, you're dealing in the weeds. Not to say that I think I could do it better than some other like, you know, marketing gurus that have been doing it for 10 years, but it's your baby.
Jonathan Fischer 23:08
Yeah, for sure. James, what are some of the ways that a CEO can get in his or her own way?
James Chapman 23:15
Yeah, I I. And also, after I get my answer, I see a question that Lindy just popped up that I would also like like to get into too. But I think another way that we can get into our own way around the product. Like the thing about your product, roadmapping. and things of that nature, good products, and great products are fairly often built by committee. And it takes somebody to just like, own it and get the direction of those things. But I found myself getting in my own way when it comes to the product at times too. Because I think that I have spent far too much time in the weeds on on the product and different product features and things of that nature. But when you find something that's working with your product, now it's just time to like, let that thing breathe, and then move on to sales. And then then start to shifting to marketing and attached to long is one of the ways that we can we can get in our own way as well. And I think maybe you touched on that as well.
Jonathan Fischer 24:19
James, you keep pitching me perfect segues. I really appreciate you for that because I want to talk about your product and product development very as our next topic. Before we do that, though, just a quick, friendly reminder to the audience. We've got a live q&a upcoming, we definitely want to allow sort of some free floating whatever stream of consciousness Ask Me Anything energy at the end of our conversation here. So go ahead and begin posting some of those questions. I already know that James wants to get to one of those from Lindy, one of our audience members. So we'll get to that here in just a few more moments. So let's go ahead and jump in then. So what are some of the key mistakes that can be made in terms of your product? We've actually discussed this with some of the other guests on the show before where you know how I don't even know what your market is going to need, you build a fancy widget or you have a solution or a platform, whatever it might be, what's the interaction there? And maybe it's best to talk about it in terms of before, you know, during, and maybe thereafter, when it comes to product. So if you guys want to chime in on that topic?
Kris Rudeegraap 25:20
Sure, I can chime in on a couple of things. So one, I think, in the very, very early days, when you're trying to launch your first product, I think it's important not to feature creep and spend too long hiding in stealth mode. I always suggest to the founders, like get it out there as is quick as possible. And not too quick. But way quicker than most founders think that it needs to be so perfect. Get it out there and then start talking to customers. And so I think that's the second part of it is as a founder and CEO, you should always be talking to customers. Even as you grow and scale and you're no longer doing sales, you're no longer doing customer success. You know, I am a huge believer in talking to customers as much as you can I do a annual customer roadshow, where I talk to one to 200 customers a year, purposefully around certain topics, like our upcoming roadmap and our historical releases. And I think that is just so crucial to figuring out the direction and or other parts of the business like pricing model, Product Marketing, etc.
Jonathan Fischer 26:26
Yeah, that makes so much sense. I saw James nodding his head with a lot of energy there about let's let's get the thing moving. Right. There's something about momentum. Why don't you unpack further, James?
James Chapman 26:35
Yeah, I mean, once you take someone else's money, the clock starts, right. And so so like, you gotta go and just sitting on on product features for too long can can really hurt the business. And you can see money just start to be shipped out the window. And I think that, you know, your your product roadmap, especially in the early days should be heavily based upon your business model, right? Like, we could come up with different features all day, but what what's your core business model, what's going to be driving revenue, it doesn't have to look perfect, it doesn't have to be perfect, it needs to work, the functionality needs to exist, you need to be able to, you know, get the payments in and all of that type of stuff and make sure that the services are being rendered. But But I do think that founders can oftentimes go product crazy and go feature crazy. And that just takes way too much time. And it is way too expensive. Of a task to be able to do I've experienced it, especially if you're in the consumer side of things, right. But because when you're building things for consumers, things are constantly changing, and all of that type of stuff. And so it can be really easy to get into a feature heavy business. And so I 100% agree with Chris, I think just ship, ship the damn thing, get it out there, tested, learned and then go back to the drawing board. It doesn't have to be perfect right out of the gate. Because clock's ticking.
Jonathan Fischer 28:03
Yeah. Love it. Got to get that business rolling. Maybe you've had different evolutions and iterations with your offering. Tell us about that journey?
Lavie Popack 28:12
Sure, sure. So first of all, I definitely echo, Chris and James. One thing to add to that is like, who am I building this for? So it's not just any customer to speak to, it's important to know what building is for and set up an environment where you could constantly learning from them. And there's a couple different channels. And it really depends on what stage what what's he holding within the company. But there's a couple of different ways of like constantly learning from those specific customers. And whether it's gonna be direct customer interviews, Chris mentioned roadshow, obviously, this really great technology out there, like like a gong, or chorus where you could like, dive into like specific customers, like conversations they're having with your sales reps. And then, you know, community as well, you know, and that's something we're actively working towards is to build out our community and invite only make sure you only allow in your ideal customer profile, because you don't want to be learning from the wrong types of customers. I think that's where a lot of companies go wrong, because otherwise you're getting like, tons of mixed information from different types of personas. And you're like, Okay, what action should I be going? Yeah, this person wants that that person who wants that? What am I doing here? So it's, you know, it's a little tough, because it's like, kind of intuitive and upfront, you just want to kind of sell to everybody and you want to learn from everybody. You know, that's just, you know, it's also part of ego. It's like, you know, because you have such a large Tam. And you're like, look at this massive audience I can sell to but now like, You got to like pull yourself back. Like, this is why I'm building up for it. Yes, maybe we'll sell to all those other people eventually. Sure, but I don't want to learn from them or Right now, I don't want to like, I'll speak to them sure, because I'm a nice guy, but I don't want to learn from them. And, and I don't want to like focus my energies in targeting them and bringing them on as customers either.
Jonathan Fischer 30:13
It makes so much sense you're gathering a lot of data, but it's very targeted. That takes a lot of focus. And it's not easy to do that, because especially early on, right, I mean, you're trying to generate revenue, you're trying to get a customer. So it takes tremendous discipline. And as James said, commitment to your business model, to really push that forward.
Lavie Popack 30:29
Yeah, you're gonna get all different types of customers come through potentially, right, it's word of mouth, like your ideal customer is not going to only have friends, that are your ideal customer, right? So they're going to refer other people and but the idea is that in terms of like, a targeted focused effort should be specifically towards the ideal customer profile. And then in addition to that, when you set up your learning system, right, your feedback system, learn from your customers ensure that it's the right customers you're learning from.
Jonathan Fischer 31:00
Yeah, love that. So everyone does go through iterations. And as we learn more about our market, we see additional opportunities to add a feature or benefit or add an additional service, what are our recommendations, panelists on how to proceed?
Kris Rudeegraap 31:17
I'll try my interest there. So I think it's always important to keep a roadmap and also a backlog of all the potential features you could and couldn't do. I think that's important. So you know, you know, it's somewhere, it's locked away, you can get to it, I think it's important to kind of stay on path as much as you can, there's gonna be lots of shiny objects that come your way. And, you know, you don't always want to appease the loudest customer, I think that often happens, where you have some loud customer who might turn who's telling you to build this, but your, you know, 50 other customers are, you know, not asking about that feature. And so I think you've got to be, you know, very focused on making sure you're putting the right research in and knowing when to say no, and not building things is just as important as knowing what to build next.
Jonathan Fischer 32:09
Makes a lot of sense. I see a lot of nodding heads from the other panelists, what are some other key ways that you can know that you should move forward with developing an additional feature benefit or offering anyone else? Yeah, go ahead, James.
James Chapman 32:26
Yeah, I was just gonna say that. I think the most of it is the testing. And once you do your testing, and you figure out how this is going to add to the bottom line, or what is going to change, about the business, once you add this particular feature, that you know how best to move forward, sometimes, and I've been guilty of this, we may build things that we will necessarily want to see or we may feel for that lousy customer. But really the question you should be asking yourself is, once we make this change to the product, how is it going to add to the bottom line? Or how's it gonna create increase our users? Or how's it gonna increase? Like, like, what what is going to be 10? What is tangibly going to change after we add this next product feature, and that is not a fun process that has a lot of research that does a lot of just like getting in there and asking some really tough questions. But I've told my team now like, before you bring me a product idea, like you're going to have to show me in a tangible way how this is going to be able to benefit the business, because if not, then then we aren't going to, we aren't going to move forward with it. Because it's too easy to fall in love with cool features and things of that nature. And honestly, it starts to make the product a little confusing, like you don't know it, but over time, you'd look up you're like, we've added like, all of these different features. And I'm getting confused, like, what is it? What is what is all of this? You heard? I mean, so don't have to build just a bill. Yeah,
Lavie Popack 33:54
I totally agree with that. You know, earlier, we had, you know, we're definitely plagued with this issue as well. Just like building out a bunch of stuff, because it's cool. And like, you know, like, I like cool stuff. I like cool features. And it's a lot of fun when you're like sitting in the conference room, like talking about and like, but in reality, the way I see it, it's like it's reactive stuff. And then it's proactive stuff, right? It's like, you know, like you said, Billings not coming through, like, we got to get paid or customers are upset about something, you know, so So there's just like, things aren't happening the way they should. So we're getting there. That's like very obvious that we're having some pain points around that. So that's stuff that's like priority, we got to deal with that. Right. So then we have to build some features to ensure that you know, things are smooth. Okay, now it's like, okay, things are quiet. There's no noise around me. Okay, what do we do next? Right now that we're in a quiet room. Well, to James's point, like, yeah, that's going to be a matter of what are we what are we trying to do here? I think we're trying to grow customers. I think we're trying to grow revenue. Well, okay, so Like, how do we do that? Well, we do that by, you know, we have flows coming through our platform. Well, let's see, I mean, what are our conversion rates from from this point to this point? And then to the next point? How can we improve in the in those conversion rates? And then that's one aspect of it. And then there's the other aspect of just like, you know, what is the actual tangible value that we're providing as part of our service? And then how can we improve on that? So you know, and then, as part of that, it's again, a matter of learning from your customers like, what are the things that are top of mind from them? What are the things that they will be happy to, like, buy into additionally, or what are the things that they're constantly asking for? So as long as you set up that feedback cycle, through with the customer base, then you'll start to hear like things that are top of mind in terms of the features that you should be focusing on to offer up that additional value.
Jonathan Fischer 35:52
Makes a lot of sense. And one thing I've heard from a lot of founders to is, if there's not already other solution and other solutions available, there may be a reason. So night want to really slow yourself down a little bit before you put a lot of money resources into something. And then wonder what you want gentlemen, think of the idea of doing some internal focus grouping, group work with certain features and benefits, if that could be done, right. If it's something that there'll be completely simple to do in the beta form, and maybe use some of your customers as a test base, maybe is that is that a workable solution in certain circumstances, as you guys was it?
Kris Rudeegraap 36:26
For sure, I think you need to do that. We have a, you know, a customer advisory board or a cab that will, you know, have a product council meeting and talk about features like that we have, we have some releases that only internal users see first. And, you know, we also will reach out and find beta users. And we have, you know, now we're we have the luxury of having user research team. But in the early days, you know, I think product managers, engineers, founders, everyone sales reps would, would pitch in and be a part of that group.
Jonathan Fischer 37:00
Good stuff. Well, guys, next, I want to move into the next topic area, which is funding. Now this is an interesting area, because so many of the players in this space are all about getting the funding, right, it's getting to that next round. And it can, it can play a role in helping keep you targeted. It also plays a role in how you have to budget and how you have to grow your company. And I know there's some differences of opinion among founders as to how best or even if one should use funding in certain circumstances. So why don't we set start off? Let's go reverse order. Let's start with our younger youngest member of the team in terms of founding companies. And James, tell us what your experience has been in terms of venture capital? What what how have you used it? First of all, it'll be a great question to have you sound off on and how do you feel about it philosophically, maybe have some insights from mentors, for example, you can share with us.
James Chapman 37:51
So I'll start from a philosophical standpoint, I don't like to raise money that I don't need. So So I try to look at what word am I going to be using this money? How am I going to be using this money? Because once that equity is gone, it's gone. And so that's the first thing I'll say. The second thing is, I've been extremely fortunate because we have raised over a million dollars in funding for plain sight in a precede stage. That's not always the easiest thing to do. And it's especially not always the easiest thing to do for diverse founders, who might not necessarily have the best network, right. And so there's a lot of challenges that come along with that. But I would have capital, and I try to make sure that before we go out knocking on doors, even asking for money, there's going to be some type of growth that's going to be projected there, right. And so it's like, the question that you really need to ask yourself is once I take all this money in the clock and start, how am I going to be able to turn this money is going to be leading me into the next round of funding or leading me to getting closer to my exit strategy, or whatever the end game is for you. I'm not I think that founders have fallen in love with raising money. Because that's, you know, when you see an article in TechCrunch, or any of these other publications, that's the thing that they talk about x company has raised Y amount of dollars, and it's easy to fall in love with that. And it's easy to fall in love with fundraising, but honestly, a lot of companies don't even need to take on venture capital, right? And so like, you really need to get a good understanding of what it is you're building who you're building it for, do you need venture capital, and what you feel like you need to pour because venture capitalists for growth, right, like like that, they are not around to try to help you find product market fit. They are not around to try to help you sustain your business or any of that type of stuff. And so like those, you got to get the myths out of the door first. And I've been a very naive entrepreneur in the early days in it's hard to, you know, it's easy to fall into some of those traps. But I try to keep it very old school philosophy and just don't take our money that you don't need
Jonathan Fischer 39:59
it sent me a world of sense, I think I'd like to revert over to are the King of capital in today's panel, though that would be Chris, in arguably at well over 150 million in venture capital raise. And that may be dated information, I think yet another round maybe, since that was last published. So I still suspect, though, that you probably would agree with what James just said, Chris, talk to us about your use of capital.
Kris Rudeegraap 40:22
Yes, I mean, hitting on Jamie's point of like, when to raise I think that's important, or when not to raise? You know, I think for us in the very early days, before we even raised our first dollar capital, we tried to get out there, build a product bootstrap as long as we could. And we almost hit a point where we were having so much demand that it was hard for us to keep up with our customers, keep up with the inbound leads, keep up with everything. And so we said, hey, venture capital is actually going to be a good tool for us to grow the business a bit faster, and to keep up with demand, rather than kind of halting growth. So I'd say that's important. But then I say when you you know, even before you decide if and when I think it's important to understand, you know, different ways that you can raise money, I've talked to, you know, very early stage, you know, founders who are trying to raise a priced seed round right out the gate and didn't know that a safer convertible note was an option. And what were the advantages of that versus a price drowned. So I think you want to educate yourself, read some books, read some blogs, on everything fundraising related, and you'll help yourself a lot there. And then the last piece, I think, is I've talked to other founders where, you know, they feel like they get a term sheet and it's go time, I gotta, I gotta sign this, and the VCs are dictating everything. I think as a founder, you should be confident in negotiating and know when to turn down a term sheet. And so I think that's a really important part, too, is being confident in negotiating term sheets.
Jonathan Fischer 41:57
And, Chris, if I may, one thing I really respect about your use of capital is you you created value first. And you use the capital for leverage to go and get the market the the way that you could offer more of that same value. I do think there's a big trend right now in this space of playing the capital game, and basically just inflating a market share, to get capital, which is not the same thing as creating value. So I really my hat's off to you for doing it, to my humble view the right way. So let's rotate around to LaVey, who has maybe the a contrarian view on capital, ironically, given our show's audience, but Lavie talk to us about your relationship with capital in business founding,
Lavie Popack 42:36
sir, sure. So we haven't raised that we're internally funded. And, you know, to I definitely agree with Chris, in terms of, if you're at a point where you can't meet demand, and the only way to meet a man is by going out and raising capital, then that makes a lot of sense. My biggest issue with raising capital is it doesn't necessarily align with what the company actually needs to service your customers in the best way. And to do the things that will keep the company healthy. For short term and long term. That's my that's, that's my biggest concern. Because obviously, the you know, the VCs are investing, they're looking, they're very metric driven. And sometimes you have to do things within within an organization that aren't necessarily the aren't going to hit metrics that the VCs are looking for. But it's the best thing for the organization. So that's really my primary concern. I've been fortunate enough to not have to go out and raise potentially down the line, we will be looking to raise but at this point where we're not looking for it, and like I said, if I don't have to, I'm not going to because because of that concern.
Jonathan Fischer 43:53
Well, there's wisdom in all these views here today. So a great insights panelists, I appreciate what you've what you brought to the table. At this point, I think it's time for us to revert over to some q&a. We've had some really interesting questions come in from our listening audience. And in no particular order. From Lindy, I think this may be the question James had spotted earlier, when you first started your company. Did you have the same vision for it that you do now? And if not, how, why has an initial vision shifted? Great question.
James Chapman 44:25
Yeah, I just liked it. Because we started our platform for improving the way in person connections are made four months before the start of a global pandemic. Right. And so, we've actually been, you know, our startup has been independent much longer than it has not been and so a lot of things have shifted. A lot of things have pivoted but But what I'm very proud of our team about first and foremost, it's our resilience to be able to stick in there. And then also us having the courage to pivot back to some of the original lines of thinking that We were wanting to do, but in a different way. And so I think in the beginning, we're very focused on the consumer side of things, how the folks who are going to be downloading the app connections and finding events and things of that nature. But what I found is I'm focusing almost all of my time these days, on the b2b side of the platform, which is helping those event hosts be able to find brand sponsors, helping those brand sponsors be able to find the right events, there's a ton of upside from a revenue standpoint, you know, from that, from that aspect. And so, we've been through a lot, and I've just learned a lot and seen a lot. And I think, you know, we've seen the product grow and change a lot. And so, you know, my advice as, as an early stage founder to any of the other founders out there is just be resilient as you possibly can and really believe and trust your gut and trust in your vision. Because there's, it's not over until you quit. And we basically had every single reason to give up and to quit, like a lot of our, almost all of our investors who gave us that million dollars, right, right, right before the pandemic, they were just kind of like, while we're all afraid of our groceries, they were just kinda like, you know, it's okay. You don't have to continue to try to try to do this, like, like, we get it and understand. But, you know, we're really stubborn bunch and just decided not to quit. And so when I saw that question, it just really, really stuck, you know, hit us on my own personal versus
Jonathan Fischer 46:31
you. Yeah, that's good stuff. Chris, is your vision evolved? Very much it has it stayed fairly true. So our
Kris Rudeegraap 46:37
vision has stayed fairly true since day one. But I'd say you know, parts of the business have have evolved. And or we've had to be agile. So similar to James, you know, we were sending direct mail and gifts, a lot of times to people's offices. And so when COVID had, we had to kind of pivot into this new features to send to people's homes, and also create a lot of thought leadership for sales and marketing and CX leaders, terms of how do they react to COVID? And how does their go to market plans change. And so I think being agile, not only in your vision, but your core product functionality, and also your thought leadership content, is going to be key to just trends that are happening in the market.
Jonathan Fischer 47:23
Makes a lot of sense. Leaving maybe you're in the middle somewhere, I think the vision hasn't shifted much, but there has been some evolution.
Lavie Popack 47:29
Yeah, so starting out, the focus is a distributed customer engagement, all things customer engagement. And I was saying before, again, it'd be super super focused, not just in terms of like your product offering, but in terms of your customer and who your customer actually is and who you're servicing. So, you know, coming from Empire energy, going through all the pain points that I went through to putting together a distributed customer service, Team sales, team, quality assurance, retention, all these different types of customer engagement, motions, going into Overpass, the idea is to bring everything into one platform where any company could just tap into it and share it and then deploy a customer engagement team. But a little sometime down the road, we went back in and said okay, we got to focus on one specific area. And the area that was like, had the biggest pain point within the space, which is of course, no sales and even more specific around the SDR role specifically. So that's kind of like how I started like, like, super broad around all customer engagement. And now we're like super focused around like distributor SDR role, and also even more focused around like, you know who it is like, which who's our ideal customer profile? Who are we actually servicing for this ability to like, quickly deploy, distributed team of STRS. So that's kind of been like our trajectory of like, starting broad. And then now we're like, as focused as we could possibly be, which has been really, really great. And we're seeing it every single day in terms of like, alignment across across our teams and a customer feedback, and so on, so forth.
Jonathan Fischer 49:18
Yeah, excellent to hear that makes a lot of sense. It's neat. To see the evolution unfold over the history of a founders journey with their company. I'm quite sure. So another great question from the field. Joshua would like to know what have as each of the panelists done for their very first job. And how long did you work there? So, lady, you were just talking let's let's stay with you and tell us that.
Lavie Popack 49:41
Yeah, so what I do my very first job. Well, I got kicked out of camp when I was what 14 years old and my dad wanted to teach me a lesson. So he put me in Ace Hardware and Utica Avenue in Crown Heights. So I was on the back of a pickup truck. Bring she rock plaster sand and four to six flights up apartment buildings below for Crown Heights. I did that for the summer. But yeah, that was my that was my first job.
Jonathan Fischer 50:10
That sounds like a good character building job Chris, how about you? What was your first one? How long were you there?
Kris Rudeegraap 50:15
Yeah, so my first job was at a video store back when VHS was transitioning to DVD is and so I did that for about six months. But after that I worked at BestBuy for a couple of years so that I learned a lot about sales through working through at BestBuy.
Jonathan Fischer 50:32
That's pretty cool. James, how about you, brother?
James Chapman 50:34
Yeah, when I was 16, my first job was as a bad boy. So just bagging groceries. I used to work hard for those tips, man like asking people if I could take their groceries out to their car and help them load them in. So yeah, I think customer service I learned a lot. And it was definitely a very, very humbling job. Because, you know, the cashiers were all comfortable and that kind of stuff. And I grew up in the South, it's hot outside, you got to go outside and get those buggies and that kind of stuff. Yeah, that was my first job. And I did that was 16 all the way to like my freshman year of college.
Jonathan Fischer 51:08
Yeah, the highly regarded trainer and author at Chet Holmes was known to hire off of grocery lines. For that reason, he would go and look for the person with hustle and offer them a job right on the spot. He did that probably a dozen or 15 times. And yeah, he probably would have hired you James had the generations aligned. So great questions. Let's see here. So another question from Dennis was when I hire, when I make initial hires, the competent I try to make hires easy for me to say that compensate for my personal weakness. And Dennis is wondering if you gentlemen would recommend that strategy?
Kris Rudeegraap 51:48
Yeah, I mean, I think you want to hire people that are smarter than you and areas that you're not good at. I mean, eventually, as the founder, CEO, you should ultimately not be doing anything. I mean, in essence, all the important roles should be hired out by people that are better at you, and you can focus on making them better or taking, you know, spending your time in other areas. But I think for sure, you know, you've got to figure out when to hire the better people in the early days. Yeah, I
Lavie Popack 52:15
definitely agree with that. And I think it's a matter of trying to get get smart on one particular area. And then you get to the point where you think you're smart, and then you go and interview you realize how stupid you actually are in that, in that area. Like, okay, this is the guy gotta hire, you know, so the person that makes you feel stupid is the person you want to hire. But first, you gotta like, kind of elevate your knowledge a bit.
Jonathan Fischer 52:36
Yeah, gotta be a decent conductor before he knew how to hire the first chair. Karen has a great follow up question to that. And James, you can chime in on this as well. Would you hire someone who's dependable with less experience over somebody who isn't as dependable, but as an outright expert?
James Chapman 52:52
Give me the expert man all all day long, is many learning curves that we can get rid of. Right? Especially, or like, I feel like I can work with almost anybody at this point. You don't I mean, it and I don't, I am less concerned about like, the personal relationship side of things. I am just gonna, like, this person is very knowledgeable in this space, and they can they can get things done. And so yeah, give me give me the expert all day. Okay,
Lavie Popack 53:19
I'll take the other side of that. Yeah, I would say definitely dependable, and character is huge for me. And obviously, you have to be intelligent, you have to know your space, but you don't have to be like a super expert in it. And we always like, look outside for experts and work with those experts. But we're looking to take on employees character and someone that's dependable. And then, well, I love to collaborate with the people that I've worked with that I directly manage, which at this point is just a lot of people. But then we're like, what we'll do is we'll collaborate over something. I don't really know this thing you don't really know to say okay, we get let's go find somebody that does. But at least we'll get down to the nitty gritty of like, what it is that we don't know, and who it is that we need to find together. And usually again, that person is going to be like a consultant of some sort.
James Chapman 54:05
Yeah, and I want to change my answer now I didn't dependable but the like, you have to have somebody that you can depend on that's like by default. So So yeah, I'm switching my mind.
Jonathan Fischer 54:19
Just Just a friendly reminder, the rules are you only get one take back. So you've used yours now James.
Kris Rudeegraap 54:29
I tend to look at it from like a skill will framework and really, whether, you know, where do they sit on how skillful they are and what you're trying to hire, and where do they sit on kind of the other axes on their, you know, their will, which is like their desire, their attitude, their confidence. And so I think in some cases, I'm happy to hire certain roles. For example, like an SDR. There's someone who has less skill in that category, but a ton of well, and so I think you've got to know what roles I don't think it's a blanket statement. across every role the entire company, but I think that framework can can help you pick winners.
Jonathan Fischer 55:07
Yeah, that makes sense. And I think levy alluded to this too, you can hire a consultant who's a total expert, then you're not strapped down, and they're less dependable, right? Best. Best of all, we're, I
Lavie Popack 55:16
think it also depends on what stage you're at, with your company. You know, early on, you want to bring people that are just like super tapped in, they're gonna show up every day and like, full of energy and competent, but they might not be like, have 20 years of experience doing that exact thing. And then you have to bring in a consultant, and then further down the line, like, you're gonna hire that consultant than we actually did that. Now in the past, where we're like, we turn to a consultant, work with that person for a couple years. And then we that person ended up coming on board full time.
Jonathan Fischer 55:44
Well, we're nearing the end of our time together. Gentlemen, let's wrap up with one final question from Dennis, I think it's a good place to end. What do you find most personally and professionally rewarding about your career as business founders. And let's, let's go, let's start with James if we could,
James Chapman 56:01
yeah, I'm just super thankful that I get to wake up every day and work on something that I'm passionate about, that people find value in, and I get to do it with people, and who I know that I can trust. And so, you know, I start every morning off with, with gratitude, in prayer, and also in journaling, and things of that nature. So there's nothing else I would rather be doing. And this is something that I can see myself doing forever, I will be doing it for free. I'm a community builder at heart. And I've built this business for for folks like me. And so I think that that brings me great joy and fulfillment every single day. I
Jonathan Fischer 56:44
love it. Chris, how about you? What do you find most personally rewarding?
Kris Rudeegraap 56:48
Yeah, I mean, it's kind of a tie between customer obsession and employee obsession. I love hearing employee's stories and like, this is the best place to work and that they're so thankful that they got a job and so no, so meanwhile, actually, a couple weeks ago, I was out up in Lake Tahoe on and on a boat, and everyone on the boat was a customer of some dosto in some fashion, whether they were a user or buyer. And I didn't even know that before. And like hearing people talk about my product, or the product that we built and their love for it once I shared with them that I was the CEO of Cisco so like, just makes my heart so happy that I built a product and a service that other people love in us.
Jonathan Fischer 57:26
Love it. Love it. Maybe wrap it up, what's the most rewarding thing for you?
Lavie Popack 57:30
Yeah. So it was interesting. Yeah, it was yesterday, and I'm like, driving away. I'm like, I love being home. I love being with my kids, I love being with my family. It's like most amazing thing. And then I leave home and I come to work. And I'm like, super excited to come to work because, you know, I get to like, deal with problems. I don't like only probably like challenges that like I could think through and and kind of dissect and work through with like, awesome people around me. And I just love doing that. And to do that towards the ultimate vision and the mission of what we're doing here. Which, you know, we're changing people's lives. So that as a whole to me, it's just amazing to be able to do that. And I was talking to my wife and we're like, you know, people that don't have that it's tough, like people that don't have a great at home and don't have a great at work. It's really hard. And we need to be so thankful to you know, to not only have our day job to be you know, our day jobs, awesome and love what you do throughout your day, but you come home at night and he just happened to be with the family and yeah, so just you know, thankful for all of that. And
Jonathan Fischer 58:37
that's it. Get the total package. Well that's great stuff guys. Very inspiring. Well a further reminder to our audience that today's show, as always is sponsored by overpass.com Are you looking to hire a team of remote sales professionals fast? There are 1000s of highly qualified potential hires waiting for you on the overpass talent marketplace. As the world's leading solution for hiring pre vetted talent. Overpass makes building an unstoppable Sales Team quick and easy. Filter by experience and industry, interview, hire and begin your onboarding process in as little as two days. create your free account today@overpass.com We'll painless. Today's conversation has been absolutely chock full of value. It's been a lot of fun. And I want to thank each of you personally for being with us today.
Lavie Popack 59:20
Thank you, Jonathan. Thank you. Thanks, Chris, for coming out with that. Thanks, James.
James Chapman 59:26
It was great. It's good to meet all of you and thanks for everybody who joined
Jonathan Fischer 47:23
Makes a lot of sense. Leaving maybe you're in the middle somewhere, I think the vision hasn't shifted much, but there has been some evolution.
listening audiences. Well. Thanks again for being here. We'll see you next time on evolve sales live. Take care everybody
