What’s the secret to building a billion-dollar company while staying true to your values? In this episode of Not Another CEO Podcast, David Politis sits down with Kyle Porter, founder and former CEO of Salesloft, to discuss his journey of scaling the company to a $2 billion exit.
Kyle shares how "love" became the core principle guiding Salesloft’s culture, leadership, and customer relationships. He also dives into early sales strategies, navigating fierce competition, securing top-tier investors, and the creative marketing tactics that helped Salesloft stand out.
Takeaways:
Leading with Love: Kyle attributes Salesloft’s success to a deep love for employees, customers, and the sales profession. This mission-driven approach helped attract top talent and build a strong company culture.
Building Organizational Health: Salesloft focused on creating a high-performance team on an ambitious mission. Kyle explains why prioritizing leadership development and a values-driven culture was critical to scaling the business.
The Dreamforce Marketing Stunt: Salesloft hired a lookalike to impersonate Salesforce CEO Marc Benioff at Dreamforce, creating buzz and attention. Kyle shares how creative, unconventional marketing helped Salesloft stand out in a crowded industry.
Navigating Competition & Outlasting Rivals: Competing against well-funded competitors, Salesloft took the long-term approach of outlasting others through superior execution, customer focus, and efficient growth.
Hiring & Scaling a Leadership Team: Kyle details how he recruited top-tier executives by positioning Salesloft as a company where leaders could make an impact. He also shares how he handled the difficult reality of outgrowing early hires as the company scaled.
Fundraising & Picking the Right Investors: Kyle prioritized investors who would push him to think bigger and make the company better. He shares lessons from working with top firms like Emergence Capital and Insight Partners, as well as the negotiation tactics that helped him secure better deal terms.
Stepping Down as CEO & The Next Chapter: After leading Salesloft to a successful acquisition, Kyle made the decision to step down as CEO. He discusses his motivations for transitioning out of the role and how he’s now focusing on supporting his wife's dream of revitalizing Florida’s citrus industry.
Quote of the Show:
“ Step on the gas and learn faster than the rate of your own experience so that you can maintain your position on the mission.” - Kyle Porter
Links:
LinkedIn: https://www.linkedin.com/in/kyleporter/
Twitter (X): https://x.com/kyleporter
Company Website: https://www.salesloft.com/
Ways to Tune In:
Spotify:
Apple Podcasts:
Amazon Music: https://music.amazon.com/podcasts/7c6328f0-9b42-41db-8fe2-d263b4fbb261
Transistor: https://podcast.notanotherceo.com/
#NotAnotherCEO #BusinessSuccess #Salesloft
Chapters:
0:00 Intro
3:12 What You’d Do Again As CEO
10:26 Creative Marketing at Dreamforce
17:18 Scaling the Executive Team
20:41 Navigating Investor Relationships
29:54 Building a Tech Ecosystem in Atlanta
34:51 Facing Fierce Competition
38:35 The Role of Authenticity in Business
41:07 AI's Impact on Sales
44:04 Stepping Down as CEO
49:19 Biggest Challenges Faced
55:23 Kyle’s Background
1:00:49 Life After Salesloft
1:06:02 Advice to Younger Self
1:07:39 Outro
Episode Transcript
[00:00:00] Kyle: I'm on the other end of the table at the dinner place, slide the manila folder over to me.
[00:00:04] I pick it up, I open it, it's got the terms, I don't like the valuation. I close the folder, slid it right back to them. And I said "Hey, I don't have to go back to my partners in order to reject this offer." And then I just shut up.
[00:00:46] David: Today's guest is an incredible leader and entrepreneur. He's been credited with creating the sales engagement and automation space. The last company founded scaled to over 100 million in revenue before it was acquired for 2 [00:01:00] billion Vista Equity Partners. We met back in the early days of the tech scene in Atlanta.
[00:01:05] We were both part of that ecosystem as it grew into one of the best in the country. I've used him as a sounding board countless times over the years and tell everyone who brings his name up that he's the best sales mind I know. He was recently inducted into the technology hall of fame of Georgia. welcome founder, former CEO, and current chairman of sales loft, Kyle Porter.
[00:01:29] Kyle: Oh, David, man, great to see you. I am excited to be here, man. I'll tell you, uh, thanks for that introduction. But David, you are, we've known each other for over 15 years now, right? Um, going way back. And I'll tell you what, man, one of the reasons I'm so excited to be here today, you're one of the first founders I ever met, maybe the first founder I ever met.
[00:01:50] Who was honest and transparent about the problems of your business. Um, you know, we kind of grew up in this stage when people were always crushing it when you'd ask them what they were [00:02:00] doing and I'd ask you how you're doing. And you'd go like bullet point good, bullet point bad, bullet point good, bullet point real bad.
[00:02:06] And I'm working on it right now. And it's the number one thing I'm focused on. And I thought that was awesome, man. I just, uh, I just want to say that I appreciate that greatly. I look back in our email history. I just searched through and looked at all of our emails. And I found that we shared, you and I, um, over 20 mutual introductions, either initiated from me or from you with the sole goal of helping each other out.
[00:02:29] And so for that, I'm, I'm very grateful. And, um, you know, another thing I realized is that I emailed you every time we were raising capital and it was like,
[00:02:38] David: yeah,
[00:02:39] Kyle: you know what that, and, and I remember taking something valuable away from every single one of those interactions. And the last thing, man, I, um, uh, you know, I've got like, my heart bleeds for the city of Atlanta.
[00:02:49] Right. And, um, when you came down, you lived in, you lived in Atlanta, then you lived in New York,
[00:02:54] David: yeah.
[00:02:54] Kyle: you opened the office in Atlanta, that was like singing my song, you know, and I, and I think like. [00:03:00] That cemented me as a fan boy of yours forever. So I couldn't be more stoked to be here with you and thanks for having me.
[00:03:06] David: Thank you, Kyle. I love that. Alright, let's jump right into it. First question. So, what is the one thing that you did at Sales Loft, big or small, that had the largest impact and that you'll absolutely do again if you're CEO of another company in the future?
[00:03:23] Kyle: All right. Well, you did tee me up with this. So I had some time to marinate on it. Um, and, and I, the answer came really simple for me and I realized I could actually, uh, field it with a one word answer. I'm assuming this is not going to be similar with other people you've interviewed. But for me, the one thing that we did that I believe led to our success, that I would do always and forever with businesses I operate is, it's the word love, L O V E.
[00:03:51] And I'll extract on that, or, you know, I'll tell you more, but, you know, when I came into this business, there was this deep love for the people that [00:04:00] we were going to attract to be part of the company. There was this insatiable desire to serve and love sellers. And so I think this love for our lofters, our customers, the market, our stakeholders, this led me to be just absolutely fanatical about building or really about leading a high performance team on an ambitious mission.
[00:04:20] And I remember saying that over and over and over again, what am I doing? I'm leading a high performance team on an ambitious mission. And we kind of summarized all of that into this one phrase that we used over and over and over again at sales off, which is organizational health. Um, so I'm happy to unpack that further.
[00:04:37] Uh, but you know, leadership, um, first and foremost, and then high performance team, ambitious mission. And it all comes from a point of love.
[00:04:48] David: I love, uh, I love that. Um, let me ask you, when, how did you, like, how did that permeate throughout the org? Like when [00:05:00] you were hiring someone, how did you check for that? You know, whether they were gonna fit into that when you were building the product? Like how, how did that permeate itself through how you operated the business?
[00:05:13] Kyle: Well, you know, you, when you introduced me, you described, um, kind of me as a sales mind. And I think most people who know me do think about that, you know, very early on in their kind of analysis of who I am and what I do. Um, but the irony is, is that I started sales loft without the name of a company and without the knowledge that we were going to build a product into the sales market.
[00:05:35] So I started the company with no business idea and no name. And I started it with one reason. And the reason was is that I felt like that if I wanted to take the talents and skills that I've been given and learned and built and use them in the biggest way possible, that I can make an impact on the world.
[00:05:51] I believe that starting a company was the best framework to do that. So pre sales. The idea of me running a [00:06:00] company was I wanted to create an environment where others could come to learn more, to do more, to take their talents and skills to the next level, to serve others and find fulfillment. That was the mission before there was even a, uh, a product or even a market or even a name.
[00:06:13] And so, you know, that came from my history, which maybe we get into, maybe we don't, but, um, that, that translated to every single person who came in and was part of the company. And so they knew that that was my personal mission. And secondarily, uh, you know, love for our lofters was the first piece. The second piece was love for sellers.
[00:06:34] Once we got into that market, you know, like I didn't have anyone on the team until we did that. And so what we did that, it was, I love sales. I've been selling my whole life. I love sellers. I understand some of the problems that they face. I have a deep desire to learn them better. And then I have a deeper desire to help them solve those.
[00:06:51] And so we were on a mission to transform the sales profession forever. And if someone came to the doors of sales off looking for an opportunity with us, and they weren't going to be on that mission, [00:07:00] then we didn't want them. In fact, even the engineers are all of our first hires of engineers. Were people that explicitly professed that they had been in places where they had worked hard to build software, but it didn't sell and they didn't like the way it distributed.
[00:07:15] And so they recognize the importance of the sales function in that effort. And so we just, you know, we just injected into everything we did and it came out transparent day one in the interviews and we were hiring missionaries. And then the other piece of that is, you know, I was obsessed with personally becoming the best leader that I could be.
[00:07:35] And then also helping others become what we called, and I think it's a Jim Collins phrase, a level five leader. And a level five leader is someone who combines extreme personal humility with intense professional will. So it's about prioritizing the company's success above your own ego, but at the same time, demonstrating fierce determination and unwavering commitment to achieve your goals in, in, in, you know, long term [00:08:00] organizational mission.
[00:08:00] So I think that was, you know, that was all kind of baked in and then it just meant we're going to run the company as healthfully as we can. We're going to do the right thing. We're going to be performance based, but we're also going to love each other and our customers. And you know, that kind of, we just called that all organizational health.
[00:08:14] David: Hmm. I think one of the things, you know, that definitely has been true about you from the beginning is authentic in, to your point, the love for what you're building and for the people you're building it for. Um, and you really became the thought leader. In the space, um, and my, my, and I think that that, that really helped the business get to where it got to because people were following you and following kind of where you, where, where you felt like the market was going.
[00:08:48] Was that natural for you to kind of talking about all that, being that thought leader, you know, um, because you loved this space or did you have to work at that? [00:09:00] Like,
[00:09:00] Kyle: Yes and yes. I think,
[00:09:02] David: mm
[00:09:03] Kyle: you know, um, I kind of go back to, you know, lover of sales my entire life and not just selling, but those who sell, you know, like mad respect and appreciation. And so I'm very, very, very fortunate that we built a business. That was the thing that I cared the most about, you know, that I cared so much about.
[00:09:24] And so, and we also were doing it as a business. So like sales loft, kind of our ICP was kind of almost always us at every stage we were at, those were the vendors that we sold the most to, right. And the pains that we had were the pains we were solving that other people do. And so that was like, like my ICP was always me.
[00:09:44] And so that made it easier,
[00:09:45] know,
[00:09:45] David: interesting. And then it becomes easy to sell, right? Because now you're telling someone, we're using it. We're building this for ourselves. You know, and I never thought about that
[00:09:56] Kyle: and we
[00:09:56] get better at our own selling by doing [00:10:00] customer discovery.
[00:10:01] David: right, right.
[00:10:02] Kyle: learning from everybody else and how they're doing it and what they're doing different and, you know, and, and, and then we're solving those problems, but I think it just comes back to this like intense passion for seeing you, David, be better at selling at BetterCloud and me.
[00:10:18] Wanting to dig in and learn as much as I can so that I can apply all of my capabilities to help you do it better. And it's not just software.
[00:10:26] David: so one of the things, tell literally, I'd say I bring this up to 90 percent of the companies that I work with, advise, whatever, is the story of kind of your creativity in a number of ways, but one that I will never forget is one of those first dream forces in the early years of sales loft. And I would like you to tell the story because, um, I don't know that I do it justice and I literally tell everyone about it.
[00:10:52] So I would like you to. Documented here so that I can just share this clip with people
[00:10:56] Kyle: Okay. Well, uh, you know, I want to take you back to the first [00:11:00] Dreamforce I ever went to. And, um, I, I, I learned that Dreamforce was a circus. It was the wildest place because you had, it was the largest SaaS event in the world. Right. And we were blown away by how much money people were spending on these booths.
[00:11:16] I mean, they're like the, the platinum booth was a million bucks and it was like the third from the best booth. There was like a diamond tier. And like, and I don't remember where the other one is like. You know, like some like superhero metal or something, you know? And, um, and so blown away. So the very first one, we had no money.
[00:11:35] It's like three people on the team and we walk in and there's just thousands of people, tens of thousands, hundreds of thousands. We took one of those coffee tables from like the hangout area. We put it right next to the entry of the main auditorium, put a sales off t shirt on top of it, opened up a laptop and stop people and gave demos.
[00:11:56] And that was, that was our first booth at Dreamforce. And we did that until they told us to [00:12:00] leave, you know, we got like a solid hour of just hanging out there and like, and, and, and, and there was this, you know, John Bertong, he was an early, uh, member with me at SalesLoft and he had one of the greatest lines I've ever heard in sales, he would walk up and this is like, I mean, we're nobodies, we're wearing t shirts at Dreamforce.
[00:12:18] We've got three people in the company. He would walk up to the biggest suit and tie, like best dressed executive. Look them straight in the interrupt, like walk in front of them, look them straight in the eyes and say, you look like someone important that I need to know. And the dude would be like flabbergasted.
[00:12:36] First of all, he's like, no, one's ever done this to me before. And he'd chuckle and he'd go, what do you got, man? Like, you know what I mean? It's like you hit them right where, where, where it helped the most. And, and so we did that. So, you know, that was like year one. Then a couple of years later, we're like, we got to do something to stand out.
[00:12:53] And you get, I mean, like. Like people were buying entire restaurants next to Dreamforce for like a [00:13:00] million dollars. I don't know how many millions of dollars they're spending on these things. So we're like, how are we going to stand out in a way that like really, really makes us memorable. And, uh, the idea came that we were going to impersonate.
[00:13:12] The CEO and founder of Salesforce. com, Mark Benioff. I don't know how this idea came about. The next thing you know, we have a Craigslist posting. Wanted. Fake Mark Benioff. Look alike. Come to us at Dreamforce. You know, be part of our crew. This floats around the company. And one of my buddies pings me and he's like, dude, our friend cam looks enough like Benny off the guy I like played poker with in college.
[00:13:34] I'm like, all right, well, let's call cam up. Like, Hey, what are you doing on these dates? And he's like, I don't know. And he's running like a recruiting company. We're like, all right, we'll pay your flight and we'll give you a place to stay. We'll give you a dreamforce badge, but you've got to dress up like Benny off.
[00:13:48] And he's like, I'm in a hundred percent. So dudes in the next thing, you know, uh, Tammy McQueen, who runs marketing for sales off, grabs these black Converse. And like custom paints, like blue cloud on the side of [00:14:00] them and like DF on the back. Um, we get a bunch of Pardot swag because it's kind of a new in the acquisition funnel for them.
[00:14:08] Um, uh, we take, uh, like headphones and like twirl them around a pen. So they look like a squiggly, you know, like security earpiece. Our head of marketing, our head of sales is, uh, he's a male model and he's got like all black suit on, black sunglasses, squiggly earpiece. Um, we He's walking around. Tammy, our South African director of marketing, wearing her Lou batons with a clipboard and they got fake Marc Benioff between them.
[00:14:32] And they just walk around all of Dreamforce. He's signing autographs. He gets up on one of the outdoor stages. And like,
[00:14:39] David: I didn't know this
[00:14:40] Kyle: hands to like charity or something. And we're, I mean, we're, we don't even know where we're going with this. We're, we're just like, maybe we'll get to write a blog post that we impersonated Mark Benioff.
[00:14:50] Like that was our whole idea. And we're having fun doing it. We're like tweeting. We have other people tweeting, like spotted Benioff drinking a coffee over here and it's a picture of him. [00:15:00] And, um, and so the, it really came to a head when the security team came up to our booth. And we're like, oh shit, you know, we're in trouble and they go, Hey, uh, Mark, uh, is aware of what you're doing.
[00:15:12] We saw the Craigslist ad. How'd you see that? And, uh, Mark is impressed and he'd like to meet you. So I'm like, all right, let's do this. So we ended up like hanging out with him, taking photos of the booth, like faking the real Mark Benioff. He's making jokes like, Hey, thanks for keeping the press off my back and taking care of it.
[00:15:29] I had other things to do. And, uh, but the highlight of all of it, so, you know, Craig Rosenberg, Funnelholic,
[00:15:35] David: Yeah,
[00:15:35] Kyle: hosted this party at Dreamforce every year. It was like a cigar bar party. And this is, this was like every ICP and VIP that we cared about was at this party. And so I wanted to be there and I want to shake hands, meet people.
[00:15:48] So I get there and Craig gets the microphone, looks at everyone. He goes, before we get started, I need to announce the greatest Salesforce, the Dreamforce marketing play that I've ever [00:16:00] seen. Bring up Kyle Porter and he tells the whole story. And I'm like, that's the ROI right there. Like we did it. Um, so that's the, the fake Mark Benioff story.
[00:16:07] We wrote a blog post. Kind of fun. Tried
[00:16:10] David: I,
[00:16:10] Kyle: to follow it up and, you know, ran into some trouble.
[00:16:13] David: I love that story.
[00:16:15] Kyle: mean, and it's a talking point forever, right? Like you could go to any exec that, you know, people would introduce me, like, he's got, you got to tell him about that thing you did.
[00:16:22] David: yeah,
[00:16:23] Kyle: we've got a prospect, you know?
[00:16:24] David: Was there anything you did ever that, Like lived up to like another campaign or initiative or anything that was
[00:16:32] Kyle: no, I, I don't think there's anything that was as like shocking and storytelling as that. I mean, we, we tried to, we tried to nominate Benioff for president. Um, Adrian Grenier from the Entourage, that HBO TV
[00:16:46] David: Yeah Yeah,
[00:16:49] Kyle: for president, took a selfie, ended up being a business insider.
[00:16:52] It was like, Adrian Grenier wants to be Mark Benioff's running mate. And then the rest of the article was like, is, is it at least if sales off gets their way and it was like all about [00:17:00] us, we got Jim Kramer. We shot money at Jim Kramer. Um, while he's filming mad money, that was kind of fun. We had women and men dressed like uncle Sam and stilts, handing out these buttons and Vinnie off for president stuff.
[00:17:15] But now after that, it became a little more traditional.
[00:17:18] David: Um, well one of the things you know as you scaled the business, um, you know you you had a number of people Kind of join you on the executive team. You built out your team. You had some pretty Team In my opinion, some pretty impressive people kind
[00:17:35] Kyle: Thank you. Yeah.
[00:17:36] David: Some scaled with the team, some didn't scale, you know, as the company. Can you maybe talk about that and, and the leadership team and what you were looking for and, and how did you identify, you know, who the right people were to bring in?
[00:17:50] Kyle: Yeah. Uh, great question. I think,
[00:17:52] David: Hmm.
[00:17:54] Kyle: of, as we talked about in the beginning, the rule number one is they have to be on for the mission. So, you know, we're not, we're [00:18:00] not mercenaries here. We're on a mission. We want to fundamentally transform sales forever. And we want to create an environment where you're going to learn, grow, do more, become more.
[00:18:07] So we wanted to punch above our weight class in terms of the caliber of executives we could get on board. Um, but we didn't want them to be too far ahead in that they needed more resources or were more accustomed to, you know, kind of a bureaucratic environment. Um, but every candidate that we hired for an executive role.
[00:18:24] You know, I, I, I had to position sales office, something that they hadn't gotten before and that they weren't going to get it somewhere else. And so what that was, was that leadership impact and, you know, really kind of living a life of fulfillment and, and, and join almost joining this, like, I don't want to say cult, but joining this, this group that is going to take you to the next level and really push you to be the best you can be.
[00:18:48] Um, but also give you a ton of resources to get there with a lot of inspiration. Uh, but yeah, we, you know, we got to a point where we had to recruit outside Atlanta, which was a pro and a con, you know, it was kind of sad to distribute the executive [00:19:00] workforce, um, but it allowed us to attract a lot higher caliber of candidate because there just hasn't been that many SAS.
[00:19:05] You know, multi million dollar businesses in the city of Atlanta, or especially up to that point. Uh, I think one of the things I teach or like, I don't know if teach is the right word, but, you know, I kind of advise or coach founders on that are scaling. I'm like, You know, you really probably think you're going to keep your executive team a little bit longer than you might really need to, um, because at some point they kind of reach a, they either expand their capabilities dramatically, or they reach a point where you need to up level them.
[00:19:33] And so I would tell, like, I love these people with my whole heart to the day I die still today. But I would still tell them, like, if you don't up level, then I'm going to have to level above you, I'm gonna have to hire a level above you, whether you stay or not is also, is up to that new person, quite frankly.
[00:19:48] And, um, you know, I had a mentor who once told me, he said, you know, true, uh, love of your executives is if you can fire one and then go on [00:20:00] vacations with them for years after. And, uh, and I do have, uh, um, uh, uh, you know, I, I traveled, I 10 days ago with someone that we let go after five years of being part of the company.
[00:20:12] And so I did take that to heart. But, um, yeah, you know, you, you definitely have, you're on an executive team and you're working for a CEO who is, you know, always learning, growing and doing the best they can. Then you've got to stay at that pace. You've got to grow at that pace too, or else their needs for an executive are going to surpass your capabilities.
[00:20:29] And so I highly recommend if you're that CXO, that you just step on the gas and learn faster than the rate of your own experience so that you can maintain your position on the mission.
[00:20:41] David: You had a lot of pretty amazing investors over the course of the company kind of journey. When you think about the investors who had the biggest impact, who were those investors?
[00:20:56] Kyle: Yeah, uh, yeah, I think this is 1 that people [00:21:00] can make a mistake on, um, pretty easily, you know, so going back to that idea, what I said, I was committed to learning faster than the rate of my own experience. I knew we had to do that in order to achieve our mission. So, I looked at investors as I'm recruiting the best option I know of for us to get better.
[00:21:20] And I'm out recruiting investors. And, you know, Series A, I had competing term sheets, and I had a term sheet for common stock at a higher valuation than the preferred stock at a lower valuation deal that we chose. And it was all because of who was behind it. At this point, it was me. Jason Green of Emergence Capital.
[00:21:38] Um, but you know, I tracked down David Cummings in the early days. Who's kind of the Prince of Atlanta SaaS. I tracked down Tom Noonan, who's, you know, legendary in Atlanta for his tech operations and investments. Um, you know, after Series A with Emergence, we went to Insight Partners and had Jeff Horing, the founder of the company on our board.
[00:21:58] Um, I was obsessed with getting [00:22:00] the best who would make us better. And I wasn't, and I was willing to sacrifice valuation and, and And dilution in order to get that. Um, but I'll tell you the, you know, we, I used to tell people, I'm like, dude, I have the greatest board. They'd ask me like, what's it like with these guys?
[00:22:15] And I'd always say, and you might even ask me this question too. You might be the one who said this. Um, you're like, well, you know, what's it like working with these guys? And I'm like, dude, they're amazing. They never tell me what to do. You know, they're always supportive. And then the question comes back.
[00:22:28] Well, did you ever miss the number? And I'm like, no. So I don't have that experience with my board. Um, You know, so I can't, can't speak to that, but I will say that when times were the toughest in those board meetings, they were the most supportive. And then when times were the best, they were the most challenging.
[00:22:49] David: Do you think that they, I mean, those are firms that are literally some of the best venture firms in the world. Um, did they add the same value? You know [00:23:00] what I'm saying? Like did those firms, their, their scale, their teams, like did they add the same value or was there nuance to kind of the different firms and the
[00:23:09] Kyle: Yeah.
[00:23:10] David: they
[00:23:10] Kyle: Every one of them offer different value, except one value that they all provided. And I'm not sure they even really knew they were doing this. Every board meeting, I would leave the board meeting believing this company can be bigger and better than I thought going in. And that was the biggest thing that they gave me.
[00:23:30] I mean, so super intangible, right? Um, but then yeah, like Jason Green was incredible at screening executives for us and really finding out the areas for improvement of those executives, which by the way, you know, kind of back to hiring executives. I wouldn't hire an executive unless we had mutually agreed upon their opportunities for improvement.
[00:23:51] Does that make sense?
[00:23:53] David: Yeah. Yeah.
[00:23:54] Kyle: agree that these are your areas for development. And then they had to give me the thumbs up that they [00:24:00] would let me challenge, coach them and push them to get better in those areas and hold them accountable. Um, so Jason was awesome at that. Um, you know, David's like the everything guy.
[00:24:09] Like he, he just, He has a way of having a short, concise, to the point answer for like so many of the different challenges you have. Um, so I call him like, he's like the ultimate tool belt, you know, of every challenge and problem. Um, you know, and then, and then Jason, Jeff Horing of Insight was really good at raising capital, strategic decisions.
[00:24:32] Yeah. So they all added tons of value, um, but they also were really just good all the way around. The other thing I would add that I say to founders is like, You, you gotta, you can't be like, um, like we work level, uh, hubris, you know,
[00:24:47] David: hmm.
[00:24:47] Kyle: I don't want to say that at all, but you definitely have to be super confident.
[00:24:51] And there's a couple moments. I know you like stories. I'll tell you two. Um, one is Emergence Capital. When I sat down with Emergence Capital, [00:25:00] uh, they kind of got old school on the term sheet, Manila folder, three, three founders of the fund. I'm on the other end of the table at the dinner place, slide the Manila folder over to me.
[00:25:09] I pick it up. I open it. It's got the terms. I don't like the valuation. I close the folder, slid it right back to them. And I said, Hey, I don't have to go back to my partners in order to reject this offer. And then I just shut up and they ended up going up. Like, I want to say they went up like from 24 million pre money to like 29 and a half million, which was super cool.
[00:25:35] And I had, I had the benefit of Jason. Um, Jason Limpkin had already told me, Hey, I'll invest at 29 million. And so like 29 and a half or something. So they were like, what number does it need to be? And I'm like, well, Jason Lincoln said he'd do it for 29 and a half. You know? So that was pretty cool. Um, the other one was, I remember we were like, even before that term sheet, they were diligencing us and they asked this question, uh, one, I'm not going to say name who, but it goes, um, what's the [00:26:00] difference between you and Yesware and this is at the time when like Yesware was our competitor
[00:26:03] David: I remember, I remember,
[00:26:04] Kyle: and, uh, no offense to any of them, but my answer was, and it was like, without missing a beat, no pause, my answer was, well, they don't have me.
[00:26:14] You know, I hadn't been like that arrogant through the whole process. I was like, it's time to like drop one. I'm like, Oh, just the biggest difference is they don't have Kyle Porter. Great answer. Um, so I think you'd have to have that kind of chutzpah, if you will.
[00:26:29] David: what I what I what I think it's a couple things you said there I want to call out first of all you had again you had crazy investors But each one of them had that special skill or that area where you could go to them And I think that's really important because what I see is people raising and funds Telling those founders, we help you with fundraising, you know, interviewing the candidates, getting you customers, getting you in a, like they give them a list of 47 things and they say, we're the best at all of these [00:27:00] things. And I tell people, my experience is every investor I had was great at one thing, maybe two, but no one, even the best firms in the world are not good at the list of 10 things that they tell you they're going to do. I love that because those are specific things that really do move the needle. I mean, Interviewing execs, if you're great at that, that can like really change the company trajectory and history and everything. Like, they don't have to also be great at seven other things, and you shouldn't expect that, you know? And I, so I think that that is one thing that you said I really want to key in on, because there's think the, the venture market has become so competitive. There's so many people and the venture investors pitch bullshit for a lot, like for a lot of the stuff where it's like, how could you do those 10 things?
[00:27:48] Well, like it's not, it's, it's impossible.
[00:27:50] Kyle: Yeah, I agree.
[00:27:52] David: So that, that's, that's definitely, you know, uh, the one thing. And then the other thing I think you said, which I really like is the power of them [00:28:00] helping you think bigger. that for me is probably maybe the biggest thing. Biggest thing a great investor can do is make you see that there's when you're in the weeds and you're down here And you've got this problem in this problem and they're like, but wait You've got something here that can be much bigger and I feel like that That should that's actually something they don't sell
[00:28:23] Kyle: Yeah, yeah, yeah.
[00:28:23] David: that that's actually really
[00:28:25] Kyle: Not only do you, David, have something that can be bigger, but you have more capabilities. You are better, right?
[00:28:31] David: Yes.
[00:28:32] Kyle: I would walk out of there with like, boom, confidence. Confidence in me, confidence in the mission. Just up. Every single time. And, uh, and so, yeah, I think that's, uh, that was definitely the biggest one.
[00:28:43] Oh,
[00:28:44] David: that Let me let's talk about atlanta a little because you know, we we
[00:28:47] Kyle: sorry. One more thing. And you helped me with this. So you raised a venture debt round before we did. Do you remember this? And I was like, dude, you gotta tell me about this. And we dug in and you, Bart was your [00:29:00] CFO at the time. I believe we spent a bunch of time with them. And what I didn't realize was how powerful having that venture line of debt was in the equity negotiations.
[00:29:11] Like in fundraising, because I would go into these, you know, series B or C or whatever it was with the, with or without you energy, right? I'm going to get this mission done with or without you as an investor. And I have this capital also that I can roll with, even if I don't get equity.
[00:29:30] David: that as leverage basically to say, Hey, I've got this line of 15 million. I'll draw it. I don't have to do this round
[00:29:38] Kyle: maybe not even like a vocalized leverage to them, but just in my heart, I know, you know, like we don't care whether they come lay, pray or stay, whatever happens, our toes are still tapping when we're talking to the equity guys, you know,
[00:29:51] David: Yeah.
[00:29:51] Kyle: uh, that's, uh, I think that's a fast times at Ridgemont high quote.
[00:29:54] David: so let's talk about Atlanta because that's somewhere where both of us started our careers. Well, [00:30:00] our lives, our careers, you know, um, What was it like building in Atlanta? In your view, what was it like those early days?
[00:30:11] Kyle: I think there were some benefits and there were some, um, challenges, right? Uh, the benefits were that since there wasn't an abundance of capital, we were resolved to building real businesses, you know, like focusing on, uh, customers and revenue and organizational health over playing the Silicon Valley, Bay Area Venture Capital Popularity Contest.
[00:30:43] Right? There was none of that. Um, and I think that was really good because it set an awesome foundation for the business. Um, that was the best part. Uh, there are really good founders that give back in Atlanta. [00:31:00] Um, and, and kind of that angel stage. And that was awesome to be able to know that they're successful, multi exit, awesome entrepreneurs in the city that are willing to give you their time.
[00:31:12] And maybe it's because they don't have 200 people asking for their time, right? You know, if you're, if you're Bay Area, you got a thousand maybe, you know, so maybe that is partly, you know, the benefit. And then I think the challenge is, you know, like at first, I mean, we were, we started the company in 2011, you know, the world wasn't as flat then, especially as it relates to Bay Area investors, you know, deploying capital in, you know, Georgia.
[00:31:36] And so I think, you know, capital was, was different for us. So we had to kind of like really bootstrap it at first. You know, raise angel money, but no institution. And we didn't raise an institutional round of capital until four years after we started the business, you know? Um, but, and when we did, it was the first investment in Atlanta that Emergence Capital had made, you know, I think they might have like one follow on that was out there that ended up being out in Atlanta.[00:32:00]
[00:32:00] Um, so yeah. And then the executive thing was tough. You know, there's not a lot of like really seasoned executives as you're scaling up to a hundred million and beyond that have kind of see the playbook. There's not a lot of IPO SaaS people in the city. Um, so that was a little tougher. And so you had to go, we had to go, we chose to go remote based on that.
[00:32:19] Um, for me,
[00:32:19] David: And how about now? What is your view of the
[00:32:22] Kyle: you know, I mean, like when someone leaves sales loft, they, you know, they have a multi billion dollar exit under their belts and then they go somewhere else and maybe in Atlanta, like more, more than likely in Atlanta. Um, you know, there's a lot of great startups in Atlanta that have great ex lofters and that have capital from the exit of sales loft on their balance sheets, you know, um, and BetterCut
[00:32:43] David: hmm.
[00:32:43] Kyle: too, right?
[00:32:43] I mean, like you're people,
[00:32:45] David: Yeah.
[00:32:45] Kyle: no one stays forever and they go on to other things and they can contribute to the business. So I think it's better. Um, I think that, uh, Atlanta probably didn't participate. In Zerp [00:33:00] as much as the rest of the world, we still did to an extent, I think, um, but, you know, because of that kind of more traditional business environment, uh, I mean, even us, if you look at our numbers compared to our West Coast competitors, we burned way less capital.
[00:33:17] Um, and had way better unit economics
[00:33:20] David: Mm hmm.
[00:33:21] Kyle: and it's kind of cause we had to, and I'm glad we did. I
[00:33:24] you see, I
[00:33:25] David: for me, the Atlanta thing was very, it's, it's interesting to look back on because you do realize that there are these, there are amazing founders, amazing entrepreneurs, amazing companies, and in these markets that are, there's many others that are like Atlanta, you know, in the, in the country and in the world, and they don't, If you don't have the sources of capital, if you don't have people who've done it before, it's really it is hard I mean, it's a it's the the friction is much higher and as you start to have that in the ecosystem It starts to to kind of smooth out that that [00:34:00] growth and that I don't know.
[00:34:01] It's it was because now I mean now in atlanta you can go somewhere and be in a building With surrounded by a bunch of other tech companies and be having coffee and run into another fountain. Like that didn't exist that literally have to seek each other out. And especially to get like, there wasn't the, I mean, there were no network.
[00:34:23] I feel like I went to a networking event. It was like 12 people, you know, like it was like, there was there that didn't exist.
[00:34:29] Kyle: right, what is it? Wednesday, you know, at lunchtime right now, if you go to InTown Golf Club, there's five tech founders in there having lunch today right now. I'm pretty sure of it.
[00:34:38] David: Right.
[00:34:39] Kyle: then if you go, and then after this afternoon, if you go to the Atlanta Tech Village and grab a coffee, there's four or five tech founders in there having coffee.
[00:34:46] And it's a four minute mile. Like once you see it, it's a lot easier to do it.
[00:34:49] David: Exactly. Yeah. I, so you mentioned your competition, um, and you've had some pretty fierce competition, uh, you know, let's say, I don't know how [00:35:00] you want to say that, but the, over the years, um, how have you competition. Do you, is, are you kind of obsessed about beating the competition and kind of head to head?
[00:35:14] We're going to out feature them out, sell, you know, or is it, we're going to go down this path and build what we're building and kind of try to put blinders on to, to that competition.
[00:35:24] Kyle: We said we were going to outlast them
[00:35:26] David: hmm.
[00:35:27] Kyle: we thought about it. But let me talk about competition. I'll share kind of some of my thinkings here. Uh, I grew up, uh, and I've always been a great, uh, fan of and lover of, um, fresh water. Boating and, and water sports, right? So I grew up on a Mastercraft and I have one now.
[00:35:47] Mastercraft and companies in the entire world. This is like a 50 year old business and they're number one. They have nine competitors fighting over a small market with incredibly [00:36:00] tough margins. This is like the company of my youth and they have a 300 million market cap. So all things in perspective, right?
[00:36:07] We've, we've built a company that 8x their market cap, which is wild to me, right? Um, so all things in perspective at sales loft mastercraft, we have an infinite market Because there's new companies coming up every day that, I mean, like a virtually infinite market. And we really only had one competitor at a time, which we routinely fought and beat.
[00:36:30] So with less resources than those competitors, right? So that gave us a lot of confidence. I mean, it started, I mentioned the Yesware thing. Um, they had raised a bunch of money from Foundry and Bradfeld. We didn't put a target on them, but we knew we were better and we knew we were going to be better. And so we did.
[00:36:45] And then I remember ToutApp raised money from Andreessen Horowitz.
[00:36:48] David: Yeah,
[00:36:49] Kyle: when they raised that round, they, the CEO tweeted, this is the last round that's going to be raised in this space. We went on to raise 200 million, you know, and, [00:37:00] uh, and then they got gobbled up by Marketo, you know, not to be seen of again.
[00:37:04] Then the biggest competitor for us was InsideSales. com. They raised like a hundred million dollars between Microsoft and Salesforce. com. Um, they ended up having us try to buy their assets and we like, wouldn't even low ball them because we didn't want to do it. Cause we'd rather just take their customers, you know?
[00:37:21] Um, and then the next one was outreach. You raised a ton of money and, and we've surpassed them now as well. And I think they burned a ton of money. They zurped it out. You know, all of these companies were great competition. They encouraged us to fight harder. They made the market better. Uh, they pushed us, but we just had the mission of we're going to outlast and, um, and we're going to do it the right way.
[00:37:42] We didn't say we're going to strategically be much different than them, other than the organizational health and values piece, which I think was important thing, quite frankly. Um, and we have new competition today, so, uh, you know, game on, but,
[00:37:55] David: yeah,
[00:37:56] Kyle: you know, our friend David Cummings, who founded Pardot, sold it to [00:38:00] ExactTarget and later Salesforce, I asked him, I said, what was the biggest surprise of the Pardot journey?
[00:38:05] And he said the single biggest surprise of the entire journey was how nasty the competition with Marketo got. Like how kind of like edgy it felt like they got on him. And, and we felt the same thing with one of our competitors, quite frankly. Um, but at the end of the day, you know, you can't control what they do.
[00:38:24] You can only control how you act. And I think everybody
[00:38:26] David: right.
[00:38:27] Kyle: And, and so we just wanted to be the best we could be, care more about the customer than anyone else. Out innovate, out execute, and outlast.
[00:38:35] David: I think, I think going back to what you said earlier, and I really think that this is important for people to hear is I do think that the authentic. authenticity about this market and, and loving this customer and, and the, the seller and the problem. I do think that is actually what if you, because competition has gotten so crazy, like the competition.
[00:38:59] [00:39:00] Now, if you start a company today. Within a year, someone's copying you. Probably 10 people are copying you. Within a couple of years, you've got 100 competitors because it's just too easy. It's too easy to build the products. It's too easy. And so you can't, actually the product is not, at least in my opinion, I don't think the product can really differentiate or can't differentiate long enough, fast enough.
[00:39:21] Like, you have to have the team.
[00:39:24] Kyle: Yeah,
[00:39:24] David: The community, the thought leadership, like that actually is the I feel like for some period in SaaS the product was the differentiator and now the product has become, I don't know, does that make sense? Like,
[00:39:42] Kyle: absolutely. Our number one, our original marketing mission was to do everything that we can. This is the marketing team. Was to do everything that we can to help our customers sell better, period. And even if it has nothing to do with the product, right? We'll come in and give you a lesson on the 10 best ways to hire [00:40:00] your sales team, right?
[00:40:01] Like we're going to do everything we can to teach you how to sell better. And sometimes that might include the product. Right? Um, and so, yeah, I'm, I'm game with that. I mean, if you understand your customers, if you care about your customers more, then you're going to understand them more. If you care about serving them better, then you're going to come up with the solutions better.
[00:40:19] You're going to deliver those in a way that helps your customers get to where they need to go. And so, yeah, I mean, that's differentiation and sure. I mean, like. A lot of these apps. Now, I think at the stage where sales loft is today, uh, the edge case learnings of, you know, connection with 10, 000 CRMs and email servers and all the enterprise security capability, like all those edge case builds, that would be very difficult for a company to just kind of rail off and copy.
[00:40:49] And that's, you know, we've had big hyper funded competitors that moved into our market, but never really did. Because. We've got, you know, 12, 13 years of these edge cases. [00:41:00] Um, so I think there is some of that as you get into enterprise software, but for early stage, I agree. Yeah. It's easily copyable, copyable.
[00:41:07] David: do you think, in your space specifically, what is the impact that AI is having and will have? I mean, obviously it's vast,
[00:41:19] Kyle: Yeah.
[00:41:19] David: curious to get your take since you were really at the beginning of
[00:41:22] Kyle: Yeah. I mean, I think the contrarian perspective that I have on that is that everyone overestimates how much and how fast it's going to impact. Um, you know, I can go back seven, eight years ago where investors looked at me in the eyes and go, you know, I know AI is not impacting sales today, but it will within the next 18 months.
[00:41:43] And then 18 months later, I know it's not, but it will within the next 18 months. And that story is continued, right? We're pretty far into the large language model revolution right now. And there is not, there's no like standout startup sales AI solution. [00:42:00] We've been baking it into our application and our offering way before people were using GPTs, you know,
[00:42:06] David: Mm hmm. Mm
[00:42:07] Kyle: we didn't even call it AI.
[00:42:08] It's just smart, you know, it's just like using data to help make recommendations, like that's the way we thought about it, you know? And, and we hired people that, you know, were understood AI and were, you know, app applying it, but we, you know, we never really market it. I think we kind of felt like that the marketing was a little bit of, um, too much sizzle and not a lot steak.
[00:42:28] You look at what salesforce. com does, like, I mean, what did Einstein came out? I don't know, seven years ago.
[00:42:35] David: Yeah,
[00:42:36] Kyle: I don't think it ever turned into a product. Like, I mean, half the shit they say on dreamforce never becomes a real product. I remember there was a talk, our VP of sales at sales off gave when he was at Salesforce and we saw the video and I'm like, You pitched all that stuff.
[00:42:48] Did that ever come to, no, never once, you know? So I think, I think there's a lot of that. Um, but in reality, what we're doing at sales off is we're saying [00:43:00] one, what are the actions that can be done without the need of a seller? Okay. Let's automate those things. Two, what are the things a seller needs to do and how can we really speed it up?
[00:43:11] And how can we populate the action they need to take in their execution queue and make it easy for them to act on it, right? And so it's getting really smart about next best action. It's getting really smart about using the data that you have to prompt communications for the sellers, to prompt next steps for them.
[00:43:30] Um, you know, and it's offloading some of the work to robots, but not too much because at the end of the day, like. A customer can sniff out a robot from a mile away and it's the same thing as spam. Um, you know, the best spam filter in the world is the human receiving it on the other end. And so I think, I think, you know, it's got a long way to go, but it's, it's still, it's less, it's less sellers.
[00:43:52] Per ticket, if you will. Um, but it's not replacing their work. It's empowering them to do a better job, kind of like [00:44:00] the Jarvis and Iron Man suit for Tony start.
[00:44:03] David: Yep, I like that. Um, now you, you're no longer CEO at SalesLoft, you're chairman. Um, why did you step down as CEO, um, from, from the company, you know, when you did?
[00:44:21] Kyle: we sold the company in December, 2021. In Q1, 2021. I went to the board and I said, I want Loft to participate in a liquidity event this year. Now, that didn't mean it needed to be majority or a strategic, you know, a minority recap would have worked as long as there was a tender offer for the way I positioned it.
[00:44:44] The way I stated it in my head over and over again is I want Lofters to participate in the value they've created in the case that the market might change dramatically because Tech markets can change dramatically, right? So that was the first [00:45:00] thing that kind of, you know, I thought about was, um, was that.
[00:45:05] The second thing I would say is, um, Tom Noonan, board member of ours, he was a CEO of a company called Internet Security Systems. He told me a story about in the dot com bubble, how his company had an offer to sell the business for three billion dollars, and the board turned it down because they wanted to remain independent and go public.
[00:45:26] His son was a fifth grader at the time and they ultimately sold the company for two and a half billion dollars. But when his son was a senior in high school, um, and that was lots of international travel, lots of dilution, hiring and firing, ups and downs, challenges here, challenges there. Um, and I didn't want that to happen for me.
[00:45:46] David: Hmm.
[00:45:47] Kyle: So that was really a motivation. Um, some other motivations were COVID, COVID changed, um, the way things felt for me a good [00:46:00] bit, you know, I'm like, I was like, my superpower is like walking in the office, dude. Like I'll walk in the office and I'm, I'm pumping everybody up. I'm loving every lofter. I'm getting them together as much as we can.
[00:46:14] There's no place that I would have rather been in the world at that time. Um, than standing on stage with lofters, customers in the market, in the room with us. And, um, and that was just like my favorite time. And that went away in a moment's notice with COVID, right? I mean, we had, we had our, our annual sales conference set to go off in mid March in San Francisco.
[00:46:39] And we had like 2000 people that had bought tickets with 2 million in sponsorship sales. We had paid the speakers already. We had paid, you know, we'd like deposit on the hotel. And, um, and I was like, that was it, man. That was the, that was the most alive that I could feel every single year [00:47:00] was marching into Rainmaker and, and just step it on that stage.
[00:47:04] And that went away and that changed things for me. You know, I still love the company. I still love my job. I still love our customers, but I didn't get to exercise my passion in the way that I had prior. And so that kind of weighed on me a little bit. Um, but I'd say the very biggest reason that I wanted to do this deal was that, uh, the day I met my wife, who, you know, from college at Emory, April, uh, on our very first date, she asked me what my dream was.
[00:47:29] And I told her it was to start a technology company that made a dent in the world. And I asked her what her dream was, and she told me that it was to restore the glory that once was in the tangerine and citrus business, in the Florida citrus industry, which she's a fourth generation, uh, Floridian farmer.
[00:47:47] And so here I am now, 15 years married. April's been supporting my dream for over a decade. And now I have an opportunity to go and support her dream [00:48:00] and, you know, get some liquidity and apply it to that. And that was the kicker for me that said, go time.
[00:48:05] David: COVID one for me is one that I, that really resonates with me. I, I, I, when I went back to the office in like June of 2020, I think I actually cried when I walked, like actually walked in the office and everyone's hoodies on the back of their chairs and literally coffee cups were where they left them.
[00:48:25] Like, and I, I was like, wow. This is gonna be different, and I hate it, honestly, like, I, you know, um, I mean our offices were in the same building for a long time in Atlanta, like, when I would come there, I I would be in that office at 7am and I'd be leaving at 10pm and I loved, I loved every, I, that was for me, like, coming there, flying down there, staying at that shitty Spring Hill Suites and like, going around the corner.
[00:48:49] Kyle: of us would be hosting a party that week.
[00:48:51] David: that was the best. That was, I'm, I, I think it really, um, I'm with you. That, that for me was like the biggest change for me. Like [00:49:00] that, all that energy that I had every day. Cause it's a hard job to do. It's exhausting and I would get energy from that. And that, when I didn't have that, it became really hard, um, for me.
[00:49:10] You know, that, that was, um, so I, I think that's, that's a good, um, call out. Let me, let's, I want to ask you what is. The biggest challenge you ever faced. I know they're countless. What was the biggest one you ever faced and and how did you overcome that?
[00:49:27] Kyle: yeah, early in the sales off journey, we had a prior product to what we sell today. It was a data solution. Think like Zoom info, collect phone numbers, email addresses, title of, um, marketing and sales prospects. And the way we did it was we had created a Chrome extension that allowed users to capture information that they found on their own LinkedIn search searches.
[00:49:50] Um, it's called Prospector and it was a wild success. It went from zero to 7 million in ARR in a 18 month period of time. And, um, it didn't use the [00:50:00] LinkedIn API. What it did is it allowed users to, their Chrome extension would scrape what was on their website in front of them. Um, but it was the fastest and best way on the internet to build a most accurate targeted list of leads.
[00:50:13] We built it. We sold it. It really worked. It scaled, but it was kind of like a house built upon the sand because it wasn't our environment. It was LinkedIn's environment and they didn't like that. And so they came after us. They couldn't technically shut us down because we didn't use the API. Um, but they threatened to sue us and yelled at me across the table once.
[00:50:36] Uh, but the worst thing was I walked into the office one day and Katie Christian, one of our incredible customer service success execs, walked up to me and she goes, Kyle, um, my LinkedIn is no longer, I no longer have a LinkedIn profile and neither does anyone else at the company. And so LinkedIn as a negotiation leverage tactic [00:51:00] had removed our LinkedIn profiles.
[00:51:02] For everyone who had like linked sales loft to their LinkedIn. They just, I don't know, they just shadow banned it, I guess you'd say. Right. And so you could type in California sales loft and it was their Google search index, the result, and you click in and go no longer available. And so I was, it, it was, uh,
[00:51:21] David: didn't know this part of the story. I didn't know. I didn't know that part of the
[00:51:24] Kyle: yeah, so it wasn't, um, you know, I laugh about it today, of course, but, uh, and the moment, It really hurt me because I felt like I was in direct violation of my own mission to love and serve our lofters. My actions led to their professional network and quite frankly their career opportunities being eliminated, right?
[00:51:47] Like, their career asset was eliminated because of my actions. Now, I didn't feel we broke any rules. We had attorneys on our side that said we could fight and win against LinkedIn. [00:52:00] So it costs you a ton of money and they have a big legal staff. Um, but we also had the beginnings of what at the time we called sales off cadence.
[00:52:10] That is now the flagship of sales loft was in the works. We had been building it and we had started distribute it and it had a lot of really good traction. So that was the hardest moment. And I remember having, um, like, I don't know what you call it, but like chest,
[00:52:25] David: Heart palpitations.
[00:52:27] Kyle: palpitations. I remember having, um, uh, dinner at my parents house and I'm like eating my food so fast and like.
[00:52:35] All of a sudden I just feel like locked up in here and I'm so stressed out about, can LinkedIn shut us down? Are they going to fight us? Or like, we're going to disappear. And then I just like, I did the wrong thing. I should have like told them instead of just like snuck out and hit around the corner and I'm just like, you know, and so that was the lowest moment, but we ended up, um, coming to a good deal with LinkedIn, you know, we saw their [00:53:00] perspective that they felt like that we were, Helping their users violate their own terms of service.
[00:53:05] So we were enabling, we were putting them, the user, our users in an environment where they could easily kind of violate their own user terms of service with LinkedIn, you know, gray area. I, you know, I don't think it's illegal. It's certainly not illegal, but, um, what we realized is we don't want to build a house upon sand.
[00:53:22] You know, we want to build something that we own and that we control and that we can edit without having to worry about the, You know, JSON on LinkedIn site change, you know, like it was a cat and mouse game. And so we built sales off cadence. It became the flagship. We went back to LinkedIn. I went back in and I made a deal with them, verbal deal.
[00:53:41] Hey, we'll shut this product down. Um, but I want some time and I want your verbal agreement that you'll take a strong look at using our new software for your sales team and consider giving us integration with LinkedIn Sales Navigator. Um, long story short, LinkedIn invested, they bought the product, and they gave us the first crack at the Sales [00:54:00] Navigator integration.
[00:54:01] And we went from, in LinkedIn's eyes, we went from the doghouse to the penthouse of partnerships. We made them a ton of money at exit, which was super cool. Um, but yeah, that was a trying moment for sure and really scary.
[00:54:12] David: I remember sitting with you And you're telling me this and I'm like and how much revenue do you have now? And it was six million seven whatever it was and I was like And that's gonna go
[00:54:22] Kyle: Cashflow positive too.
[00:54:23] David: like I remember and you're like it's gonna go to zero I'm like, that is a lot of revenue to make up. And yet we have this product, whatever. I'm like, this is a fucking, this is going to be, this is going to be like, you know, one of the craziest comeback stories. If you go from seven to zero, you know, and, um, that was, I mean, To get to 7 million of revenue is hard, you know, to get to like, to get to that and to get that fast is like, it's hard even today, you know?
[00:54:51] And, um, I remember, I remember that. And I was really like, I didn't know the part about them shutting off the actual LinkedIn
[00:54:59] Kyle: [00:55:00] Yeah.
[00:55:00] David: that,
[00:55:00] Kyle: we made a tombstone, RIP Prospector, and we like signed it and put the dates, and then I had like carried it with like some incense in my hand, like, oh, yeah, they're walking down the halls and I. Popped it right down the middle of everyone. And I, you know, we made, we made a hard turn and we went all in on the future of the company and it turned out
[00:55:21] David: amazing, I want to, I want to transition to you. So, so what is your, where are you from originally?
[00:55:27] Kyle: Uh, grew up in, in the suburbs of Atlanta, Georgia, Little Bristow mountain area, Atlanta, Georgia. My dad was a Georgia Tech grad. I knew I wanted to be a Yellow Jacket my whole life. So I went to school at Georgia Tech and, um, you know, Atlanta, Atlanta is my favorite city in the world.
[00:55:43] David: Did you always know you were going to start a company?
[00:55:46] Kyle: Yeah, I think so. I mean, I was like. I sold beanie babies and baseball cards and like comic books and I bought and sold bicycles and computers when I was a kid. I was like, Oh, like the [00:56:00] 1996 Olympics came to town in Atlanta and I bought the lapel pins and would sell them like frenzy down at Centennial Park.
[00:56:07] I just, I loved, like loved, I mean, I remember like selling GI Joes in the neighborhood and kids eyes are lighting up and I'm like feeding off that energy, you know? And so for me, it's like when someone need something, want something, or maybe even doesn't know how valuable something can be in their life.
[00:56:24] And then someone just helps them get it. Like that is just so cool to me. So I've always been a fan. And I think that led to just knowing that, um, that the only way that I would feel fulfilled or that I was doing my part was to, you know, be an entrepreneur.
[00:56:39] David: Do you think that that was, do you think you were born with that? I mean, do you think, like, everything you're describing, like, were you just born that way? That's, that's in your DNA?
[00:56:49] Kyle: I had some super serious complications, health complications as an infant and as a child. And they led to some like insecurities in me where I, I mean, I [00:57:00] had a nurse that would come to my house once a week for the first 10 years of my life and drop a gamma guard, like IV fluid in my body to fight off infection.
[00:57:09] And so I kind of had this, um, maybe like something to prove from an early day. Like, I don't know. I felt like everyone else was normal and I was like the sick kid. And so I needed to like, prove that I wasn't that guy. And so I think maybe some of that insecurity led to like, wanting to stand out, be different, makes it happen.
[00:57:26] So I think to be real introspective and kind of transparent, I think that might've come from that.
[00:57:31] David: What was, like,
[00:57:33] let's say, your biggest break? You know, like, in your career, if you think back, like, was there a moment in time, a person, like, a break that put you on the path?
[00:57:43] Kyle: Well, I went to rehab. Uh, yeah, I mean, in college I, I partied too much and, you know, got in trouble and got arrested and ended up going to treatment and actually fundamentally changing my whole life. And November 29th, 2002 was [00:58:00] the date. Um, and that was a big, big, what I realized up at that point. Kind of going through this program, I realized that my whole life, I had these like talents and skills and capabilities and that I had used them, like squandered them basically, but also had used them like selfishly.
[00:58:17] And I came to this conclusion that I'm like put here for a reason. So I want to use these talents and skills to make the world a better place. And that's what I'm gonna do for the rest of my life. And so I like kind of the script flipped for me in 2003 and my whole life changed in that moment. And so entrepreneurship was, was great because it was the best platform for me to use, to make a difference in other people's lives.
[00:58:39] Yeah. So, you know, a little bit of trouble, a little bit of stupidity. A little bit of like trying to be cool to, you know, probably goes all the way back to childhood insecurity, quite frankly, you know, worked through it with my, uh, CEO coach a bunch.
[00:58:56] David: April, you mentioned before your wife. I mean, she's been there for this whole [00:59:00] journey. Um, and, um, can you talk maybe about how that relationship, you know, and, and her putting her stuff on the back burner till now?
[00:59:08] Kyle: Yeah.
[00:59:09] David: cause, cause I feel like in our conversations, a lot of things have, like the support that you had was, was a big part of the success.
[00:59:17] Kyle: Yeah. You know, when you, when you do like, uh, one of these forums, whether it's like YPO or 10X CEO, you know, any of these things, like you read blog posts, you hear a lot of like, entrepreneurship's a lonely journey, you know, and that's one that I never really felt. And I think that's because of my wife and my dad and the friend network we had.
[00:59:36] I mean, even our relationship was so important to me because I could call you and share the problems. And then you would like share your problems. And then I didn't feel like a shitty, you know, like a shitty CEO, like I was a loser because we both had the same problems, you know, or we had different problems, like, I don't know, like sometimes you feel like if things are going wrong, you suck and it's like all on you.
[00:59:56] And, but entrepreneurship is all about going through [01:00:00] all that stuff. And, and so I had a lot of people that I could really count on in April was the biggest. You know, she's the biggest and she didn't just kind of hold back and like watch and, you know, she, I mean, she, she, she served the mission by helping.
[01:00:13] And then also she was like the breadwinner when we didn't have any money.
[01:00:17] David: I
[01:00:17] Kyle: That's all the money in the business. Like I had a, like 80K due to Kyle Porter note on the balance sheet for like two and a half years, three years. And April was like earning a W 2 income. And so, yeah, couldn't have done it without her.
[01:00:30] And, you know, it's just as much, uh, my journey as her journey. Um, but now we're in a flip situation where she's. She's working Kyle Porter energy right now on her business.
[01:00:42] David: so, so I wanted to ask you that, like, what are you doing now? Like what, what is the plan for this next
[01:00:49] Kyle: Yeah. So, um, you know, quite frankly, I think I got burned out a little bit through software. Um, I don't know if burned out's the right word. I don't think like people get burned out unless the mission changes. The mission [01:01:00] changed for me and software wasn't the answer for what I was looking for at this point.
[01:01:04] I still love it. I still talk LP in funds. Um, I helped start a credit fund called Conductor Capital, uh, and we do, uh, debt loans that are non dilutive to growth stage SaaS companies between 5 and 20 million ARR
[01:01:20] David: I didn't know
[01:01:21] Kyle: that are growing 25 plus percent, like EBITDA neutral ish, cashflow neutral ish. Um, and so, you know, had, had SalesLoft been more debt capitalized at exit, we all would have made more money because of dilution.
[01:01:34] Um, you know, we were 95 percent equity, um, you know, capital. Uh, and so I think there's a founder friendly way to grow in an anti dilutive way. And so that's conductor capital. Um, and if anyone, you know, wants to explore our debt facilities and credit, um, we'd be open to talking about that. So I do that. Um, and then, you know, I'm into, I'm into the tangerine and citrus business.
[01:01:57] So, uh, we've acquired a [01:02:00] business. We've, uh, grown groves. Uh, you know, bought land and, um, you know, we're pretty aggressive into tangerine farming. Live on a tangerine farm in central Florida. Uh, the kids are picking fruit and selling it at the farmer's market. Um, and my wife is extending the fourth generation to the fifth generation.
[01:02:16] And, you know, we have a intellectual property for the best variety of fruit in the state, in the U S. Um, actually I looked it up on perplexity AI the other day. I said, what's the, uh, what's the best tasting tangerine in the world? And the first answer was, uh, Noble Juicy Crunch. So I was pretty excited about that.
[01:02:33] Uh, and our goal really is to take Juicy Crunch worldwide so that we have year round supply of a product that right now, demand is here and supply is here. So we, we work in a market where demand outstrips supply 5 to 10X. And so the goal is to create supply. Have
[01:02:49] David: Amazing.
[01:02:50] Kyle: And it's cool being on, you know, like being on a farm is really fun.
[01:02:53] I got three kids, 10, 7, and 3. Um, you know, they're out on their dirt bikes and four wheeler go [01:03:00] karts and we got horses next door. We got boats and guns and you know, it's the country life and I got a I got a half acre of personal, um garden out here with every fruit and veg, you know variety we've got. I hear chickens are coming.
[01:03:14] This is my wife tells me chickens are coming soon. Um, so, you know, we'll see how that grows and changes but uh, you know, we do have uh fun on the farm, but You know, I still, no matter what I do, you know, I love, I love entrepreneurs. I love what you're doing because of how many people you're helping and serving.
[01:03:32] And, you know, that's a passion of mine that'll never die. Uh, you know, I want people to find fulfillment through entrepreneurship. And I know that for many people, that's the way they're going to use their talents and skills to make a difference in the world. And so I'm here to help on that journey too.
[01:03:46] And, you know, I probably take about three, four mentor calls a week with various investments I've made. Um, you know, once we get this thing, this, uh, farming thing on autopilot, we'll see what happens. It's [01:04:00] conductive capital, investing in the farm life.
[01:04:02] David: Awesome.
[01:04:03] Kyle: really
[01:04:03] And uh, and
[01:04:04] I'm spending a lot of time with family and friends, you know, quite frankly. And, um, and I'm doing, um, baseball coaching. I'm reading with the kids and, you know, I'm riding, I'm riding my dirt bike with my three year old in my lap while I ride.
[01:04:16] David: Oh, like,
[01:04:17] Kyle: She always wants to go faster and she always wants to go on longer journeys. I'm like the only, I'm like one of the only dads at all the field trips. I dropped the kids off for school every day. So it's, it's good times and, you know, really grateful for the, the journey that's led us to this point.
[01:04:31] David: um, I say all the time, you know, like I, I first six years of my kids lives, something like that. I didn't see them, you know, I didn't, I didn't, um, that was the sacrifice to make, you know, six, seven years. And we were watching videos the other night and I was like, I don't even remember that entire age, you know, and, uh, and I think that it is a gift and lucky to be able to, to spend the time with them, you know, um, now, and, and, uh, and it probably [01:05:00] won't last too long because then they're not going to want to hang out with us.
[01:05:02] So
[01:05:02] Kyle: Hey,
[01:05:04] David: you have a three year old. So you have, you have like a little bit of,
[01:05:07] Kyle: well, one of the things I'm doing and maybe, uh, you, maybe you've already thought of this, but, uh, so my daughter's 10 and we made a pact three years ago that every single year for the rest of our lives, we're going to take a trip to go see a band she likes. So.
[01:05:22] David: just you, just you and her.
[01:05:23] Kyle: So we went to Luke Bryan two years ago, went to Luke Combs last year, and I think we're going to go post Malone this year.
[01:05:30] Um, uh, he came out of the country, uh, um, and then my son, we have a pack that we're going to go to every MLB ballpark in the nation, and we don't know when it's going to be done by, but we've got three of them so far, and we're going to keep going. So I'm doing these things so that I like have like, regimented ways to stay in their lives when they're 14, 15, 16, 22, you know, who knows, right?
[01:05:54] So we're going to keep trying to do that as long as they'll let me.
[01:05:58] David: I love
[01:05:58] Kyle: And that's just a way to kind of try to [01:06:00] stay in, you know,
[01:06:01] David: I love that. What, what is, last question for you, what is the one thing, you know, knowing everything you know today, um, at this point in your career, what's the one piece of advice you would go back and give yourself before you started your career?
[01:06:13] Kyle: I don't know if it sounds cliche, but I think it's just, just keep going, dude, just don't stop. Don't let anything stop you. Just go, go, go, go, go. Because when you just put your head down and drive and figure out everything on the beach, go fast, do things the right way along the way, just, I mean, think for the 40 year vision, but just go for it now.
[01:06:37] And like, I think that's probably the only thing I can think of. That, you know, I know it sounds a little bit like anyone could say, just do it. Right. Or whatever. Um, but that's, that's me, man. That's, that's how I feel.
[01:06:48] David: I think people need to hear that, actually. I think people need to hear that. I think that actually is something that you know. It's people say, you know, you stay in the game long enough, [01:07:00] you know, you'll, you'll find some, some path, you know, and I think, um, so I, I, I think that's great
[01:07:07] Kyle: tell people when they're, when they're founding, when they want to start a company, I'm like, you've got to pick a problem in a market. that you're passionate enough about serving to where you can get punched in the face for a decade, right? Like I, like you can punch me in the face a million times and I'm still coming back to help sellers.
[01:07:26] You know, like it's just, I just love it so much that you can't keep me away from it. And so I think you got to, you got to be able to manufacture the passion for the thing you're doing to withstand the ups and downs that come with the journey.
[01:07:38] David: Kyle, thank you for doing this with me. Um, it is really like, it's good to go down memory lane on some of this stuff and some of the stuff I didn't know. And, and I think people are gonna really, I, the transparency and the honesty, I really means a lot. So thank you for doing
[01:07:54] Kyle: Dude, my pleasure. You're doing it, dude. Like, I don't know how you were [01:08:00] right out, uh, stepped out as CEO and you had a book and I'm like, that thing was awesome. I read every word of it. I agreed with so much of it. Um, and the, the, the cast you're doing, like, I love what you're doing for entrepreneurs, founders, and executives who want to take that next step up in their career.
[01:08:16] And it's super cool. And you got a lot to share and say. And, uh, you know, I know I learned a ton from you along the way. I mean, do you remember all these phrases where we're like, dude, the market could totally evaporate on like five years before it actually did. You and I were like, we're totally scared.
[01:08:30] The market's just going to disappear, you know? So we're going to get the best deal we can right now. And in case this happens, we'll be, you know, and I mean, I took your mentality on that one and I took it all the way to the end, you know? And, um, and I just, I'm really grateful for what you've done and.
[01:08:45] What you've done for the community. I mean, like going all the way back to the very beginning Vocalocity days, right? Ziva, uh, you know, you're a star dude and I appreciate everything you do.
[01:08:54] David: Thank you, Kyle. Thank you. Hopefully everyone, you enjoyed this episode. I hope you share with your networks and, [01:09:00] uh, we'll see you for the next episode of Not Another CEO Podcast.
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