Mar 09, 2025
How Marty Kausas Raised $17M in 14 Days
An interview with Marty Kausas, Founder of Pylon
Founder Focused
$17 million in 14 days. While most founders spend months pitching to investors and getting rejected, Marty Kausas had VCs literally visiting his apartment rooftop to close deals on weekends.
Kausas is the co-founder and CEO of Pylon, a B2B customer support platform that's consolidating an entire category of post-sales tools. From zero to $120K ARR in three months, backed by Andreessen Horowitz and General Catalyst—but the path here wasn't linear.
In this interview, Kausas reveals the brutal reality of "pivot hell," the psychology of knowing when to quit versus when to push through, and the specific playbook he used to create investor FOMO and close funding rounds at lightning speed.
Watch the full interview now on EO's YouTube channel! Below is the complete transcription of the interview. Minor edits have been made for clarity and readability.
Key Highlights:
"Being a founder is very, very stressful. Should I keep going? Do you have a job? Do you have a career that's gonna work out? My suggestion is, frankly, if you feel like you should stop going, you should probably stop going and if you can't not continue, then you should continue."
"You need to keep trying and all you need is one thing to work out and then that'll blow away all the failures in the past. I have considered giving up many times, but there was just something nagging inside of me that wouldn't let me."
"We got to $120,000 in ARR within three months of having the idea. Got our first customer in 14 days. We have raised $20 million from investors like Andresen Horowitz, General Catalyst and Y Combinator."
"I think you should stop being lazy and learn how to build yourself."
"You need to keep trying and all you need is one thing to work out and then that'll blow away all the failures in the past. I have considered giving up many times, but there was just something nagging inside of me that wouldn't let me."
"We got to $120,000 in ARR within three months of having the idea. Got our first customer in 14 days. We have raised $20 million from investors like Andresen Horowitz, General Catalyst and Y Combinator."
"I think you should stop being lazy and learn how to build yourself."
From Movies to Reality
What first inspired you to become an entrepreneur?
Marty Kausas: Might sound stupid, but I was definitely inspired by movies like The Social Network or Pirates of Silicon Valley kind of learning about how those companies got started. I guess I could relate a little bit to the characters in the movies where like, oh, I'm kind of nerdy too. I like computers. I like programming, and maybe this could be a path I could go on to.
YouTube videos were an early teacher for me and then started making games in high school, building websites, and it was only kind of sophomore year of high school where I joined our robotics team where I got really excited about after leaving high school, I went to Purdue to study computer science. I immediately fell in love with hacker culture. There was this club Purdue Hackers where every weekend they would spend time just writing code and just trying to build games or applications.
YouTube videos were an early teacher for me and then started making games in high school, building websites, and it was only kind of sophomore year of high school where I joined our robotics team where I got really excited about after leaving high school, I went to Purdue to study computer science. I immediately fell in love with hacker culture. There was this club Purdue Hackers where every weekend they would spend time just writing code and just trying to build games or applications.
How did your experience at big tech companies like Airbnb shape your entrepreneurial journey?
Marty Kausas: While I was in college, I started to do internships, of course, so I worked at places like Qualcomm in San Diego. I worked at Yelp as an intern and then Airbnb at Airbnb, and I joined the payments team there and so I was working on back in infrastructure helping basically money move around the world, to be honest, I don't feel like it prepared me that much for startups. I actually think it probably was not helpful. It was anti-helpful. I learned all the things not to do because big companies operate so differently and so slowly compared to startups.
While I was at Airbnb, I really was not enjoying the work I was doing. I was like looking at all these other founders who were starting companies on the side, even the ones who were failing. I was more excited about what they were doing and the path they were on than what I was doing at Airbnb.
While I was at Airbnb, I really was not enjoying the work I was doing. I was like looking at all these other founders who were starting companies on the side, even the ones who were failing. I was more excited about what they were doing and the path they were on than what I was doing at Airbnb.
Welcome to Pivot Hell
Tell us about your journey from leaving Airbnb to finding Pylon. What was that process like?
Marty Kausas: When I left Airbnb, I started working on one idea which was a health tech idea. We're trying to build an app for people with Parkinson's disease to better understand their condition. It was a terrible idea for a lot of reasons, and we spent a whole year on it. At the end, I decided to pivot not only away from the idea in the industry of health tech in general, but also the co-founder I was working with.
Even when I started working with my now co-founders at Vina Robert, we spent months pivoting together until we finally came up with Pylon. What we were interested in doing was building a really big, fast growing company.
Even when I started working with my now co-founders at Vina Robert, we spent months pivoting together until we finally came up with Pylon. What we were interested in doing was building a really big, fast growing company.
You mentioned "pivot hell" - can you elaborate on what that experience was like and how you knew when to keep going versus when to quit?
Marty Kausas: I have considered giving up many times. I think in the back of your head you're always questioning, OK, should I keep going, but there was just something nagging inside of me that wouldn't let me. Hey, you know, this is what you need to be doing, you need to keep trying, and all you need is one thing to work out, and then that'll, you know, blow away all the failures in the past.
Pivoting is really, really hard. You are going to pivot a lot and you're going to pivot so much that my co-founders and I, we call it pivot hell. Now, once you actually get into pivot hell and you start working with people and every week you might be switching ideas, it becomes really, really hard to keep going. Your parents are going to ask you what you're doing with your life. Your girlfriend, your boyfriend are gonna question, hey, like, should you maybe start looking for a real job, and you're also going to have this like creeping doubt that, hey, maybe I'm not actually good at this, and should I keep going.
My suggestion is if you feel like you should stop going, you should probably stop going, and if you can't not continue, then you should continue, and that was the case for me. I basically didn't feel like I had a choice. I had to keep going because that's just how my brain is wired.
Pivoting is really, really hard. You are going to pivot a lot and you're going to pivot so much that my co-founders and I, we call it pivot hell. Now, once you actually get into pivot hell and you start working with people and every week you might be switching ideas, it becomes really, really hard to keep going. Your parents are going to ask you what you're doing with your life. Your girlfriend, your boyfriend are gonna question, hey, like, should you maybe start looking for a real job, and you're also going to have this like creeping doubt that, hey, maybe I'm not actually good at this, and should I keep going.
My suggestion is if you feel like you should stop going, you should probably stop going, and if you can't not continue, then you should continue, and that was the case for me. I basically didn't feel like I had a choice. I had to keep going because that's just how my brain is wired.
The $10 Billion Market Strategy
How did you eventually land on the idea for Pylon and validate that it could be a massive company?
Marty Kausas: One of the learnings for us was you just have to start in a really, really big market, what type of idea you want to be working on to make something really big that can grow really fast. What we did was we kind of like observed the biggest software companies in the world and turns out aren't that many public SaaS companies. You look at them, like they're probably $76 billion plus public software companies that are B2B, and of them, almost all of them are horizontal SaaS products, meaning, hey, they're selling products that can be sold into almost any industry. So think like payroll, IT, sales, marketing, customer support, etc.
We decided, OK, let's, to make sure we don't get stuck in a market, let's go after something really big. So we chose kind of post-sales customer as a category to go explore. What we did was we went on LinkedIn and we messaged 40 people a day, that's what LinkedIn would let you do. Let's say 7% of those people respond, you know, would create a cycle of us just cold interviewing people in customer support roles that we wanted to learn from.
We decided, OK, let's, to make sure we don't get stuck in a market, let's go after something really big. So we chose kind of post-sales customer as a category to go explore. What we did was we went on LinkedIn and we messaged 40 people a day, that's what LinkedIn would let you do. Let's say 7% of those people respond, you know, would create a cycle of us just cold interviewing people in customer support roles that we wanted to learn from.
What specific insight led to Pylon's product and early traction?
Marty Kausas: I think you need to be very clear with yourself what type of company you want to build. We wanted to build something explicitly very big, and for us that meant, hey, $10 billion market cap public company that was making, let's say a billion dollars revenues and also fast growing meant that usually there's some sort of emerging trend that's happening in the world where you can capture that and grow with it. So where we saw this emerging trend of B2B communication moving away from email to kind of new channels.
Our initial insight was that a lot of people are talking to their customers not over email anymore, but they are starting to open up shared Slack channels, Microsoft Teams channels, WhatsApp. We got to $120,000 in ARR within three months of having the idea. Got our first customer in 14 days.
Our initial insight was that a lot of people are talking to their customers not over email anymore, but they are starting to open up shared Slack channels, Microsoft Teams channels, WhatsApp. We got to $120,000 in ARR within three months of having the idea. Got our first customer in 14 days.
The 14-Day Fundraising Blitz
You raised $3.2 million from General Catalyst in six days. Walk us through that process.
Marty Kausas: We raised our $3.2 million seed drone from General Catalyst in six days. That's a catchy headline, and it did really feel like we were living in an episode of Silicon Valley. The story is we were 2 months into our YC batch, 3 months old as a company overall. We were probably around like $60,000 in annual revenue at the time. 2 months into YC when people start to think about fundraising, bring on investors before the end of the batch.
What we did was we scheduled as many calls with VCs in the course of one week, try to create some sort of like time pressure between the investors themselves, spreading it out, basically going in with the mentality and kind of signaling to every investor, hey, we're fundraising really hard this week and there might not be time for conversations next week, so we kind of need to knock everything out right now all at once.
What we did was we scheduled as many calls with VCs in the course of one week, try to create some sort of like time pressure between the investors themselves, spreading it out, basically going in with the mentality and kind of signaling to every investor, hey, we're fundraising really hard this week and there might not be time for conversations next week, so we kind of need to knock everything out right now all at once.
What was your strategy for getting investors' attention and creating that competitive dynamic?
Marty Kausas: Every time we got in touch with an investor, it is important how they heard about us. So instead of just like cold emailing investors directly saying, hey, we're Pylon, like you should invest in us, we instead got founders that they respected and knew, some that were even our customers already, I go message them and say, hey VC, I know this founder, the founder of Pylon, they're going to YC right now. Are you talking to them yet? You should because they're a hot company. I think what they're working on is really good.
We've got a bunch of really great introductions through that, and that just meant that the investors were coming directly to us, like basically ready to have serious conversations and we'd skip straight to partner meetings. The social proof was just already there and at seed round, social proof is everything. Your business is still so nascent, it's so hard to kind of understand, you know, where you're going to go. So having founders vouch for you who the investors trust is really, really important.
We've got a bunch of really great introductions through that, and that just meant that the investors were coming directly to us, like basically ready to have serious conversations and we'd skip straight to partner meetings. The social proof was just already there and at seed round, social proof is everything. Your business is still so nascent, it's so hard to kind of understand, you know, where you're going to go. So having founders vouch for you who the investors trust is really, really important.
Can you break down the timeline of how the General Catalyst deal came together?
Marty Kausas: To give you a sense of the timeline here, so we start our initial conversations with investors on, I guess it was a Monday, Wednesday is when we had our first discussion with General Catalyst who eventually led our seed round. Friday we had person partner meeting with General Catalyst's investors and then Saturday I went to the apartment of one of the investors, went to the roof, had like kind of a social conversation, and by nighttime that same day they gave us a verbal offer that they wanted to invest.
The general advice that we got was, hey, find people who are good partners for the long term, who have a reputable brand. That brand then helps you bring on employees because you have that social proof and then will also help you, you know, close customers. They can help you get for the next round, so General Catalyst was basically the top of our list, and so we were going after funds like them for the seed round.
The general advice that we got was, hey, find people who are good partners for the long term, who have a reputable brand. That brand then helps you bring on employees because you have that social proof and then will also help you, you know, close customers. They can help you get for the next round, so General Catalyst was basically the top of our list, and so we were going after funds like them for the seed round.
The $17M Series A in 14 Days
Then you raised a $17 million Series A from Andreessen Horowitz in 14 days total. How did that happen?
Marty Kausas: The whole process took around 14 days. At the end of 14 days, we ended up closing with Andreessen, who led a $17 million Series A round. The process of like talking to all those investors was not easy. They actually tried to fill your calendar as much as possible to make sure that you don't talk to other people once they express interest because there's only downside for them to wait. If they express interest, then they know that other investors will suddenly get interested just because of that like social dynamic.
Low dilution was the thing that was really important for us. We just didn't want to sell 25% of the company. The only way to get low dilution is to have a competitive round. We want Andreessen to better terms, then you have to go to someone else they respect. So you have to go to like a Benchmark or Sequoia, and Andreessen has to feel like they're going to lose you if they do not lower the dilution amount. It's kind of this like social game where they need to make the terms better for you and the company.
Low dilution was the thing that was really important for us. We just didn't want to sell 25% of the company. The only way to get low dilution is to have a competitive round. We want Andreessen to better terms, then you have to go to someone else they respect. So you have to go to like a Benchmark or Sequoia, and Andreessen has to feel like they're going to lose you if they do not lower the dilution amount. It's kind of this like social game where they need to make the terms better for you and the company.
What's the real secret behind raising money so quickly? Is there actually a playbook?
Marty Kausas: When he was trying to figure out how to have a good fund, he basically was like, OK, how do you have a fundraise fast like the Twitter guys, that was the example he gave. And so he asked investors, he's like, why did the Twitter guys have such a fast fundraise? There are actually no secrets. It's, you have to have a really good team building in a really big market with a really good product that people love and, you know, high potential for growth, and you have all those things, you've kind of already done all the work, here are the numbers, here's the growth rate, here's, you know, what customers are saying, and they're just going to be convinced based off of that. So really just the fundamentals are what's actually important.
Basically riding a big wave and then we have the founder slash company that's a great surfer and so as a result you can surf the big wave.
Basically riding a big wave and then we have the founder slash company that's a great surfer and so as a result you can surf the big wave.
Living in the Office
You mentioned literally living in the office. What does leadership look like at this stage of a company?
Marty Kausas: When you're competing against an incumbent, you're not actually competing with all the employees there. Most of them are not working on R&D. Most of them actually do not care because, you know, they're just getting a paycheck. We were at the time, especially living in the office, working 14 hour days. The number of people grinding at Zendesk trying to accomplish the same thing is very few.
I think at this stage, what has worked for us in terms of what the founders should be doing, what leaders should look like is just doing the work yourself. So leadership at Pylon is very much just doing the work yourself and other people kind of following by example. So like 6 months ago we were actually living at the office. It was like Robert had a bed in the living room and that, you know, everyone just had desks around him or our salesperson, his desk that he would take sales calls at was literally like 5 ft away from Advith's bed. I was like sleeping in a meeting room for us, leadership just meant doing the work and then people kind of seeing that, kind of being motivated and excited by that.
I think at this stage, what has worked for us in terms of what the founders should be doing, what leaders should look like is just doing the work yourself. So leadership at Pylon is very much just doing the work yourself and other people kind of following by example. So like 6 months ago we were actually living at the office. It was like Robert had a bed in the living room and that, you know, everyone just had desks around him or our salesperson, his desk that he would take sales calls at was literally like 5 ft away from Advith's bed. I was like sleeping in a meeting room for us, leadership just meant doing the work and then people kind of seeing that, kind of being motivated and excited by that.
How do you handle the stress and pressure of being a founder?
Marty Kausas: Being a founder is very, very stressful. At the end of every month, that's when we do our reporting on how much revenue and how quickly we've grown. We keep doing it and a part of me feels like, oh my God, this is magical, it just keeps happening, but it's very stressful. I think the only way through the stress is by just addressing the problems and grinding really, really hard so you can more consistently maintain growth and, you know, hiring pipeline and building great product.
Both myself and I think my co-founders feel very similarly where we just want to win, we want to build a company and so we just didn't let ourselves give up.
Both myself and I think my co-founders feel very similarly where we just want to win, we want to build a company and so we just didn't let ourselves give up.
Stop Being Lazy
What's your advice for aspiring entrepreneurs who want to start a company?
Marty Kausas: I think the really important thing is to be able to build and solve problems yourself. Say, hey, I'm just going to go find, let's say a technical co-founder who will build the product for me. I think you should stop being lazy and learn how to build yourself. There are lots of resources on how to do it. You could go watch YouTube like I did, go to a boot camp or any free courses that exist around the world at this point. Just learn how to build for yourself, especially with AI. It's becoming so easy, then the world is your oyster. You can have an idea, make it, and then just try it and see what happens.
So first off, if you're not like purely set on starting a company immediately, I do actually recommend just trying to get a job at a startup. You can create a network and kind of like be immersed in the startup community. So for example, you work at Pylon, we have events here all the time for founders and other startups that are coming through. So you just have an opportunity to mingle with a bunch of people.
So first off, if you're not like purely set on starting a company immediately, I do actually recommend just trying to get a job at a startup. You can create a network and kind of like be immersed in the startup community. So for example, you work at Pylon, we have events here all the time for founders and other startups that are coming through. So you just have an opportunity to mingle with a bunch of people.
If someone is set on starting immediately, what should they do?
Marty Kausas: If you are just set on starting a company immediately, I would probably go live in a hacker house of some sort. I would probably just attend a lot of meetups. YC has meetups now and events. I would just go to as many of those as you could, find the best people, and then try to get into their networks.
What would you tell your younger self knowing what you know now?
Marty Kausas: I would probably tell myself, learn from others more. I think I'm one of those people that often likes to just go figure things out on my own, which I think is really helpful, but I think there's also a lot of advice. For example, I could have gone to successful entrepreneurs and been like, hey, what do you think of my idea like is this good? What do you think are the risks, whatever, and I probably gotten to the same point two years later in months had I just like listened to their advice, taken that instead of just trying to like discover everything on my own.
Interviews like this is that hey, I'm someone who's already gone through it. Maybe you can learn from some of my mistakes instead of going through the same 2 years of pain that I did as well. So that would be one piece of advice is just go learn from other people who have done it before and are a couple of years ahead of you.
Interviews like this is that hey, I'm someone who's already gone through it. Maybe you can learn from some of my mistakes instead of going through the same 2 years of pain that I did as well. So that would be one piece of advice is just go learn from other people who have done it before and are a couple of years ahead of you.
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