← Liftoff with Keith: Conversations with Super Founders and Growth Experts sharing useful insights
Liftoff with Keith: Conversations with Super Founders and Growth Experts sharing useful insights
How David Politis Turned Grit Into Growth: Lessons from BetterCloud’s $100M Journey
00:27:01
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- [00:00]
David Politis
Foreign.
- [00:06]
Keith
Okay, we are back. I'm so glad they welcome David Politis, the founder, not. Not another CEO. That's a fun name of a company. Obviously a serial entrepreneur with a fantastic backstory and a. And a great going forward story. Did David, welcome to Liftoff with Keith.
- [00:29]
David Politis
I'm really excited to be here. Thank you for having me.
- [00:31]
Keith
You know, it's a pleasure. Obviously, I'm familiar with Better Cloud, so that caught my eye. And then I saw you were competing head on with me in the podcast business. Kidding, of course, but we're both enjoying the podcasting world, the media stuff. But, you know, as a CEO of Better Cloud, you were right in the middle of, you know, you know, SAS maelstrom and all great stuff. And you had a few other exited companies. But what I find really fascinating, David, is your backstory, how it all got started. I mean, it started in a crazy thunderstorm. So give us a little backstory and then let's get into what's going on now.
- [01:10]
David Politis
Yeah, yeah. I'm going to go to the beginning and just give you the very beginning of the story, which I grew up around my father, who's an entrepreneur, came to the country from Greece with nothing and, and worked in restaurants and real estate, then international finance. Anyway, growing up, the way we spent time together was at work. So he would have me come to his office, he would take me on trips, we'd go to the. He was developing in Harlem on 125th Street. He was developing brownstones, and he would have me go with him. I went to China and Russia and Nigeria and all over the world where he was doing work. And that was like my indoctrination into business at literally the age of. I think the first thing I can Remember is about 8 years old when I got to college. I tell people this all the time. He bcced me on every email that he sent, literally like, so that's how I grew up, was like, this is what I want to be. I want to be an entrepreneur. And when I came out of school, I started a company as a marketing assistant, a company in Atlanta. And it was international virtual number business. It was basically reverse calling card is the best way to describe it. And using VoiceOver IP, I was the marketing assistant, 15, 16 person company. And over the course of about six months, my first job out of undergrad. In the course of six months, everyone at the company got fired except for me and an engineer, just, just the two of us. And the founder said, dave, you'll be the CEO and he'll Be the cto.
- [02:38]
Keith
Just the two of us.
- [02:40]
David Politis
He's lit in an office. You know, an office is for 16 people. And then each of us had our own private space, you know, our own office. And. And so anyway, that's how I started my career. And I learned so much. So much. I mean, that was the biggest gift that I could have gotten in the early part of my career because I learned a lot, both how to do things and also how not to do things.
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Keith
Thrown into the deep end of the pool. And here we go.
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David Politis
Right away, right away, really. I remember one of the first days because no one was left at the company. I was picking up the phone and as like the sales calls and someone would ask for finance and I literally be like, hold on. And I would pick up the phone and be like, it's the finance department that get somewhere that I was doing that, you know. So anyway, that was kind of. That's how I got started. And then that company did really well and ended up getting to almost. At the end, it got to almost 50, 60 million of revenue. Was acquired by Vonage. Vonage pivoted around that company. It became a cloud PBX business. And that business, Vonage actually just got acquired by Ericsson for 7 billion for their B2B.
- [03:49]
Keith
Kind of offering them in the very early days.
- [03:51]
David Politis
Yeah, yeah. So that was my first experience. And then I went to a company called Cloud Sherpas, which was the first ever cloud consulting company. It was Google Cloud's first partner and helped them build that business. It was very small when I got there. My first experience with services. And then that business was acquired by Accenture and it became their cloud computing division. And then I started better Cloud about 13 years ago. And Better Cloud really evolved from a, I would say like a little tool to fill the gaps around the Google Admin console, the Google Apps admin console for IT people. And then it evolved to the first ever SaaS management platform. And we got the business. We sold the company about three years ago to a private equity firm. But we were on the way to 100 million of ARR at that time. And I stayed on for. For a year there. And since then I've been advising, investing and trying to join the media world, you know.
- [04:45]
Keith
I know. Welcome, welcome. So, so let me wind it up a little bit here for us to get going on this talk track of building growth, because that's really what I like talking about. And you took this thing Better cloud to almost 100 million, as you said. Then you had a great exit That's. But you also raised a bunch of money. But what was it like, David, to get to 1 million in AR? How was that? What was the lucky, you know, tweak turn tactic that you used?
- [05:18]
David Politis
I love. No one actually has ever asked me that, that question from zero to one. It was a lot of. They didn't call it this 13 years ago, but growth hacking. Yeah, we hire. So we were selling to it people who were using Google Workspace, what's now called Google Workspace used to be called Google Apps, Gmail Drive, all of that. Right. And there was a marketplace there, the Google Apps Marketplace. And that marketplace had a ranking 1 to 10. And it was on the homepage of the marketplace. And we knew that if we could get to the top of the marketplace, we would be getting installs just organically, just by. It's like being at the top of the App Store, you know. Right. We hired an intern and the intern monitored the marketplace every hour for three days straight. Because we didn't know what the algorithm was. He literally every hour. And he would monitor who's in every place, how many installs, like how many reviews. And we figured out that the algorithm updated twice a day. It updated at midnight and updated at 12. Actually, technically it updated at 3am because it was West Coast 12 and it was 3pm and we knew that it was updating like that. And we basically figured out what was necessary to become the number one application in the marketplace. We then spent months devising a plan so that we could drive as many installations of our product as fast as possible and to get to the number one place, because we could tell that once you get to number one, for someone to go above you, they had to get so many more installs. Long story short, it was basically impossible. And so we spent months doing this. And then on one day, we attacked every angle, every partner we had, every blog post we could do, everything we could do to get those installs. Yeah, we became number one in the marketplace. And that one move drove, no exaggeration, we were getting 200 companies a day installing our product. Not consumers, companies, 200 a day. Because they were finding us in that marketplace. And it was those customers, the people who were installing that. Ultimately, when we turned on a paywall, which was about six months after that, within the first month or two, we got to a million dollars of ARR. Because we had built up this backlog.
- [07:52]
Keith
Yeah, it's so, it's funny. So the lesson takeaway really is, you know, find that chink in the arm or that crack where that you can exploit to differentiate yourself and allow for that acceleration. And until you do it, keep looking.
- [08:06]
David Politis
For it, really, that. And I think it's about doing things that don't scale. I tell people all the time that people are trying to go from 0 to 1, 0 to 5, even you can do stuff that doesn't scale. I think a lot of investors, they ask you, like, what's the repeatable motion? And this at that scale, it's like I would go outside and just wave at people walking by and ask for them to. You know, it almost doesn't. My first company at Vocalocity, no exaggeration, I went door to door and knocked on people's doors in Atlanta businesses and tried to sell them the phone system door to door. You know, not really scalable, really was not intelligent. But I did get some customers and I. I think it's about doing the things that don't scale, is what I would say. But I like what you're saying, which is, it's that and finding this, like, where can I exploit the market kind of dynamics and opportunity.
- [09:04]
Keith
There's a saying that I kind of refresh my memory. It might not be exact, but something to the effect of 0 to 1 is art, and then 1 to 100 or 1 to 10 is math and science. And I think there's some truth to that. It's not 100% true, because you still need art, you know, as you're growing, as you're evolving your story and doing creative things. But you're right, 0 to 1 is sort of like whatever works. Knocking on doors, I compliment you, man. That's work, and that's what entrepreneurs have to do. You either have that in you as.
- [09:38]
David Politis
An entrepreneur or you don't.
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Keith
And you had it from your DNA.
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David Politis
Yeah, I think so. I think watching my dad make stuff up as he went along, you know, not knowing what he was selling, you know, just making it up, I think that was kind of part of it. But I will say it's hard. It's. It's hard to do that, especially when I think that we're so used to all the tools that exist and all the email automation and this. And, you know, and in reality, I think that that quote is good. Like the art, the. The. The stuff that doesn't scale, whatever is necessary in that 0 to 1, it's. It's. I think that a lot is possible when you do that. And I think a lot of founders are not willing, frankly, or not comfortable, let me say, not not willing. They're, they're not comfortable doing that, you know, in the beginning.
- [10:32]
Keith
So the, the follow up to that is a bit of a, of a side sidebar. I was just at Saster out here in California. It was a lovely weather. We would have loved to have had you out here, David.
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David Politis
No one invited me.
- [10:48]
Keith
You're part of the Saster world for sure. It's funny, this year was like Aister. I don't know if Jason Lemke would approve him using that word, but it was all about AI. So in this day and age, does that change in terms of how you would go to market today? And I know you have an advisory business right now where you're talking to companies that are maybe later day SaaS, maybe trying to figure out how to integrate AI, maybe evolving into an AI first or AI even semi native. I don't know what the proper language is, but it was pretty declarative in terms of the energy out there and focus all being on AI. So as you're dealing with companies today and talking to them about their growth plans and helping them scale to 100 million, what do you, what are you advising them on? Growth strategy?
- [11:39]
David Politis
Yeah, you know, I think that AI is obviously, you know, I was actually just working with one of the companies on deploying clay, you know, and you look at something like clay and it feels like the early days of outreach or my, the one I used to sales loft, you know, where you had the email automation. And if you go even further back, you, it reminds me of the days when Marketo came about.
- [12:05]
Keith
Oh, those were rough.
- [12:06]
David Politis
But those are the day, you know, to do marketing automation. The way Marketo allowed you to do marketing automation, that was mine at that time. It was like, I can customize an email and send it to these people and if they click on this, like that was amazing. If you go to outreach and sales loft, those companies now enable the salespeople to do that work and automate it. And it was a really big thing. Now you look at the, a lot of the AI tools and what you can do in terms of prospecting, what you can do in terms of understanding like who is in the market, how just doing discovery on prospects, especially if you're selling like a good size ASP product, that work could take, I mean if I did that by hand, that could take to do it right, a couple of hours, you know, to do, to do it right. You can use AI now to do that kind of research in a matter of seconds, minutes. And so I think there's things like that that are really powerful that you can use. My opinion is that if you go all AI for go to market like you, you literally just let AI do the work. You end up getting what I'm sure you get. And I get literally daily in LinkedIn which is, hey Dave, for your two person podcast company, can I sell you cybersecurity solutions that do. I'm like, what do you even. Is there any targeting? Like someone the other day tried tried to sell me literally a full like implementation service for Salesforce. We're two person podcast company. Like no one's doing the research because they're AI ing everything. So my answer to you is I think it's super powerful, but I don't think using it for everything and just letting it do the work. I think that's actually starting to hurt companies instead of.
- [13:52]
Keith
So put a human in the middle.
- [13:54]
David Politis
Of a human in the loop is the, is what I would say at least.
- [13:58]
Keith
And then if you're building that company today, I mean you are as a two person. But let's take the other example. Let's say better cloud. If you're at year two of better cloud in the middle of an AI era, what would that look like from a staffing standpoint? Because a lot of people are talking about this and let's not talk about overall company, but how would you look at building your sales and, and, and growth team today?
- [14:25]
David Politis
I would hire, I, I would 100% hire a go to market engineer. A person who really like not just can, but wants to get in the weeds on all these technology products, all these different LLMs like how to use them, how to use them in for the different parts of. Not a sales engineer. I mean not, you know, sales ops engineer, not a go to market engineer who could look at marketing, sales account management and all the tooling that exists and figuring out how to optimize that. I think that hire, in my opinion, I think if we look forward three years from today, those are going to be very expensive and pretty much required hires. I think for any scaling go to market high.
- [15:17]
Keith
I don't think we have to wait three years.
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David Politis
Yeah, no, no, yeah, I guess that's a good point. That's a good, that's a good, that's, that's actually a very valid point. I should have said three months.
- [15:27]
Keith
What do you surround that AI engineer with? Is it more traditional marketing or some more agents or what?
- [15:34]
David Politis
Look, well this is so the companies that I see using AI and go to market the best way. This is interesting. Every the best companies that I either work with or have like exposure to the CEOs are engineers themselves. Yeah. And they are the ones in these early stage companies setting up. They are engineers, they're setting up the tooling. And when you talk to them, they say, I've never done sales, I've never done marketing, but I understand how I can use these tools. And it's honestly, it's amazing what they're doing. So I think you need the go to market engineer with the go to market strategy minds. I think you need to create, in my opinion, you need that creative marketer who's thinking to themselves, how do I target this very specific icp? What content do I have to get? What mode? Like, what channel should I go through? Who should I be sending from? A big one right now is people just going straight to using their CEO's accounts on LinkedIn to do the outreach. Not even using the AES or the SDRs, just automating the CEO outreach on LinkedIn. But that you have to have someone who's that creative thinker, but they don't have to be the implementer because that go to market engineer will do that work. Does that, does that kind of make sense? No, no, no, that, that sounds correct.
- [16:59]
Keith
To me as well. I'm still fascinated to, by how you're sort of putting the puzzle pieces together as we go here because we don't have time to like sit and watch and, and make hypotheses on the, on a blackboard. I think it has to be in motion in public, in, in, in a, in a cross functional way, sharing with people. Here's where we're going. Get on board. If you, if it's broken, we're going to fix it and keep going.
- [17:30]
David Politis
Yeah. You know, the companies that are not implementing AI are the ones that are doing what they're taking all this time to do the whiteboard and think about maybe if we do this and we put in this tool and the ones that are really embracing it, they're just going and saying, look, I'm going to do my next campaign using AI something. Right. I had one company, they said we're going to implement AI Autodialer basically. And they did it for one particular SDR and they did it for one week and they tested it, but they didn't wait. I see other companies like, no, we have to first do this and this and, and I think that's what's, you're right. I think that's what's differentiating who's, who's Keeping pace. And who's not are the people who are doing this quickly and who are trying, who are experimenting but doing it in a, I don't know how to like, in a measurable, not just like, let's try seven things at one time.
- [18:29]
Keith
The point is clear. Hey, let me ask you about fundraising too, because it's something you have a.
- [18:32]
David Politis
Lot of experience, unfortunately. Unfortunately, I have a lot of experience. Yes.
- [18:37]
Keith
It would be nice to have it all organic and hold on to all that equity. Sure. But what, what are the tools of, the tools of the tricks of the trade today on the fundraising side? We could talk about tools if that's interesting to you, but that you see today in raising seed funding.
- [18:57]
David Politis
I think that when people are going out to raise seed funding, what I find is that one investor, one of my investors said to me years ago, he said, Dave, within 20 minutes of meeting a founder, we know if we want to invest or not within 20 minutes, we then spend the next month or two months validating that we should invest. But we know.
- [19:23]
Keith
I have other words for that, but.
- [19:24]
David Politis
Yeah, yeah, exactly. But, but that's what they, you know, that's what he said to me. And I think that a lot of founders, they come into these conversations and they don't, they don't realize how important the storytelling is. It's not that they don't have a deck. I'm not saying that it's not they don't have a big vision. It's. They don't know how to tell that story to an investor that says, I know what I'm doing right now, right here. I mean, I'm tactically executing, I've built a product or I'm in the middle of building a product. I have my five design, I'm tactically executing, but actually over here, fast forward however many years, I'm trying to build something that's going to change the world. That is a really hard. I find that people either tell you the story that they're going to change the world and can't back it up with execution, or they're the execution machine but can't back it up with any kind of vision for the future. And being able to tell that story, that's what I think. That's what a seed stage investment firm is looking for. They're looking, they need to return the Fund X number of times on one deal. They need to feel like this is someone who's got swinging for the fences, but also knows how to execute. Today, by the way, when I was raising my first round, I got turned down by a lot of the big firms, Sequoia and Benchmark and all that. And when I reflect on it, it's because I couldn't paint the picture of building that huge company.
- [20:54]
Keith
Right. So is that something that you work on with the companies you advise today, helping them tell that story in a more compelling way? You know, because that seems like there's a gap even with companies I meet today that, with a very dynamic CEO and I hear their pitch.
- [21:08]
David Politis
I'm like, what was that?
- [21:10]
Keith
You, you just did a product pitch or you just gave a, you know, a, a sales pitch, but you didn't give an investment pitch? Because I don't see what the, the huge opportunity is.
- [21:20]
David Politis
We're still talking. Exactly.
- [21:21]
Keith
Yeah. A market size is way too small for me to expect venture to get excited about.
- [21:26]
David Politis
Exactly. So I, what I do is I, I actually have people pitch me, then I go through with them on their deck. We work through the deck. And one of the interesting ones that I find another, another one that just very common is people don't spend the time to tell their story, the personal side or the business personal side of their story in a compelling enough way, because that's a huge part of what the venture investor is looking for. Is this someone who's going to grind? Is this someone who's going to dedicate their life to this? Is this. You know, and I think that when, when people, sometimes people have, most people have amazing stories, I mean, from wherever it comes from, but they don't take the time. Hey, let me tell you, this is how I started my career. This is how my life started. This is, you know, actually in the podcast, I always ask people at the end of the podcast, tell me your story, tell me your background. And when you hear some of these stories. Yeah, I would invest in a heart. You know, my, my parent was an entrepreneur and all my siblings are entrepreneurs. And I've always said I'm never going to work for any. And like, this is my third company. My first two fail. But because of that, like, you got to tell that story and why the.
- [22:35]
Keith
Struggle is real, make it come to life.
- [22:38]
David Politis
I think so. And then tell them, why is that story relevant to what you're building? And so I, all of this is like part of the, I would say, art of actually storytelling and, and getting investors excited. And then the other piece I'll say is I think that investors want to be everyone. Everyone wants their ego stroked. But investors, they want you to say, like, they want, they want you to listen to them. They want you to hear their suggestions, their ideas, their. And I think a lot of founders, this is me in the early days, I would get locked up when someone would give me, like, Dave, we don't like this. I'm like, what do you know? You know, this is how I was thinking in my head versus saying thank you. Taking down a note. Like, physically, I tell CEOs write it on a piece of paper so they can see that you're doing it, contemplate it, you don't have to answer on the spot. And then when you email them the follow up, say, it was great. Talking about, thank you for suggestion X, Y and Z. I've talked to my co founders about it. I'm not sure, or I am sure, whatever it is. Yeah, these are the things that people want to see because otherwise they're like, am I going to be talking to a wall? Like, is this person going to want to work with me? So there's all these, like, elements that when you're doing it the first time, you don't really understand the game, I guess I would say, you know, and. And over time, you start to understand some of these dynamics.
- [23:59]
Keith
Yeah, David, that's great. Hey, and before we wrap up, let me talk media with you. The world of podcasting. How's it treating you so far? I certainly will promote not another CEO to. To my listeners, but how's it going so far?
- [24:15]
David Politis
You know, I started this as just like a fun project, you know, and people told me, dave, you won't get past 10 episodes. I'm at 50. I'm almost exactly at a year of every week on Tuesday, releasing an episode. It was really hard for me in the beginning to interview versus being interviewed. That was a very. I don't know, I was. I don't think I was very good at it. I really had to work on that skill of how to ask the right question, you know, even how to keep the guest on track. Like, all of the stuff that I. You're very good at that kind of. That. That was a lot for me to pick up and figure out. And it was also, in the beginning, hard to say, like, is anyone listening to the. You know, no one's really, like, listening. And the last two months has been a real kind of shift. We've gotten just, I don't know why, a lot more listeners. I think maybe the substack. You know, the substack. We started and we have, I think, 5,000 subscribers, not, you know, 20,000, but it's. You can see that when you start owning the audience, you really can, can drive a lot more engagement. And that has been the last two months, has been. I feel like I'm getting comfortable. I feel like I'm, I'm getting the right stories.
- [25:31]
Keith
You know, you're doing a great job. And you're also showing your passion for the topics, the subjects, the guest, you know, real emotional connection, and the audience appreciates that. It's not you going through the motions. You, you're doing this as a, as a passion.
- [25:47]
David Politis
Yeah, exactly. Exactly. So it's been fun. I'm learning. You know, I'm learning, but it's something I never, I've never done before. So I'm like, I'm, I'm, I'm enjoying the, the journey and, you know, I, I, I hope it's so crowded out there with so many, so many podcasts, so much information, and my hope is just like, that people listen. When I get one text message from one episode and someone says, Dave, I listened to that, and that, like, made me, I showed to my wife, I showed to my kids. Literally, I'm like, you know, this person listened and they did this thing, and like, so for now, that's what I'm enjoying.
- [26:23]
Keith
You know, if I can give you any advice, it's, keep having fun with it. It makes it go by a lot faster. The other, the other parts will, will share other ideas and other, other ways to make it successful, whether it's toward the consulting side of your business or you reaching huge audiences or you, you go on the next Shark Tank. Who knows?
- [26:42]
David Politis
Yeah, yeah.
- [26:43]
Keith
But, but thanks for joining. I really appreciate it.
- [26:45]
David Politis
It was great. Thank you.
- [26:46]
Keith
Catching up. You're, you're on a, a fantastic role. If I can be of any other service, please let me know.
- [26:53]
David Politis
Thank you so much. Thank you for having me.
- [26:56]
Keith
We'll do it again.