Leap Academy with Ilana Golan - Wistia CEO, Chris Savage: Master the Art of Pivoting: How to Adapt and Grow Against the Odds

Episode Date: December 12, 2024

Chris Savage is a master at pivoting. He co-founded Wistia with his best friend in his living room, originally aiming to create an online filmmaking competition platform. When that didn’t work, they shifted to portfolio tools and later to secure video hosting for businesses, which became Wistia’s core offering. Chris wasn’t afraid to turn down major clients like HBO when their goals didn’t align. Despite running a $300k monthly loss and receiving multiple life-changing acquisition offers, he rejected them and took on $17.3M in debt to continue growing the business. In this episode, Chris opens up to Ilana about the highs and lows of building Wistia, how he made tough decisions, and what it takes to build a lasting business. Chris Savage is the CEO and co-founder of Wistia, a leading video-hosting platform designed to help businesses create, host, and analyze video content in a way that maximizes engagement and drives growth. In this episode, Ilana and Chris will discuss: (00:00) Introduction  (00:19) The Twists and Turns of Launching Wistia (05:02) Pivoting and Finding Success in the Unexpected (08:22) From Zero to Paying Customers (10:14) Rejecting an HBO Deal and Searching for Investors (14:51) How Focus and Authenticity Drive Success (18:02) Building a Serious Business with Fun Marketing (20:33) Learning to Make Tough, Risky Decisions (23:11) Chris’s Secret to Balancing Creativity and Speed (26:34) The Struggle to Close Deals and Break Even (30:31) How He Pushes Through Hard Moments (31:05) Turning Down Life-Changing Offers (35:23) What Chris Learned from Taking Time Off (38:24) The Power of Building a Personal Brand (43:05) Why Wistia is the Top Choice for Video Marketing (46:17) Chris’s Top Business Lessons Chris Savage is the CEO and co-founder of Wistia, a leading video-hosting platform designed to help businesses create, host, and analyze video content in a way that maximizes engagement and drives growth. A strong advocate for the Boston startup ecosystem, Chris is passionate about exploring unconventional paths in tech, entrepreneurship, marketing, video, company-building, and behavioral economics. Before founding Wistia, he contributed to an Emmy Award-winning documentary and, in 2009, earned recognition as a Top Young Entrepreneur by BusinessWeek. Connect with Chris: Chris’s LinkedIn: www.linkedin.com/in/cjsavage Chris’s Twitter: https://x.com/csavage Resources Mentioned: Webinar Wizard: https://wistia.com/webinarwizard  Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

The most valuable things, they don't happen quickly. They take a long time. Chris Savage, co-founder and CEO of Wistia, a video for business which we're using as well. Everything we do is about making it easy for you to get more value out of your video and enable you to use video better. From starting in his co-founder's living room, Wistia has

since grown into a multi-million dollar business with over 200 employees and millions of customers. We thought we would do this for six months and then get rich. We thought that's how startups worked. It took a lot longer than I thought before things really start to connect and work. It's very hard to know if you're doing the right stuff, but if you do it long enough you end up training your intuition. Based on everything that you've gone through, what would be an advice to your younger self? The first thing I would say is... Chris Savage, co-founder and CEO of Wistia, a video for business which we are using as well. And from starting in his co-founder's living room, Wistia has since grown into a multi-million

dollar business with over 200 employees and millions of customers. But Chris, it wasn't an overnight success. Take us back in time to your college days. Definitely not an overnight success, no. Yeah, I started with my best friend from college, Brendan Schwartz, and we thought it would be an overnight success. We thought we would do this for six months

and then get rich. We thought that's how startups worked and that's not how they work. It took a lot longer than I thought before things really started to connect and work. And it ended up being a lot more fun than I thought. And I also realized you can take things much farther than you think.

And so, yes, that's how I would think about it now. And I want to go there for a second, because it started with some kind of movie that you got involved and it took off, but how did that morph into Wistia? It's just such a beautiful story. Yeah, so basically I had worked on a feature-length documentary in college and was very fortunate that we got distribution and won a bunch of film festivals and stuff and I

Watched the filmmaker who had put so much into this movie I watched it basically at the last second not get full distribution and this is before streaming online really So that was an industry that was gate-keep which is not surprising That's how the entertainment industry works. But I saw that so early and I was like, ah, this seems rough. This seems like a hard thing to work on something and actually have everyone tell you it's really great and then still not get distribution. And she'd spent four years, five years on it.

I had spent three and a half years on it, four years on it myself. So that was the backdrop. And then I graduated from college in 2005. The movie came out at the same time and very soon after YouTube launched. And I saw YouTube and I was like, Whoa, this is different. And one of the things was different about it was I had tried to be a part of these online film communities before YouTube. And I was pretty tech savvy and had a bunch of short films and I could get the videos online and they never took off.

It was very bizarre. There's a lot of community building and not that much sharing of video. And so seeing YouTube was so different and after digging into it, it seemed like it was this confluence of different things. It was broadband Internet and open source tools to do the encoding of the video. And everyone had flash in their computer. And as we looked into this, Brett and I started realizing like, wait a second, there shouldn't just be one company that could figure this out. Anyone could do this.

It's actually open source things. And so that got us riffing on ideas for what this company could be. Started very close to where I came from, which was gonna be a filmmaking competition website. And then very quickly we realized, okay, we don't have connections to brands and all these other things.

And it evolved from there, but that's what got us to start. And I think it even won an Emmy award. It was, theoretically, it looked like a success, and then you were not able to really take it forward. Am I right? That's right. Yeah, we won an Emmy and the thing that was so interesting about that was I was involved in a movie that was winning film festivals and people didn't seem to care. It was not what I thought

the reception would be. And at the same time, actually, I saw this competition that was for a movie. It was called Slither, I think. And basically they said, we're going to release a bunch of footage from this movie. Anyone can edit it into a trailer and we're going to use the best trailer as the trailer. And I remember seeing this competition thinking, Oh my gosh, if I win this competition, it's probably going to be better for my career than the feature length documentary. You get like 25 grand if they use your thing.

And I was like, well, that's amazing. And being able to say you did a national ad, that would be incredible. And so it was this weird thing of this online filmmaking competition. This was a one-off where like, this would be better for my career than the feature documentary. And that was what made us think something really big could be happening here.

And that was enough to start, which was the important part, but it was not an overnight success. We started and then pivoted and pivoted and pivoted and found our way to what the beginnings of what WSTI is today. But yeah, was that understanding and this counterintuitive idea of like maybe online will really democratize this? And it totally did. It just took a lot longer than we thought. Which always does, by the way, which is interesting because there's these myths that just caused us to think that things will happen faster. But talk to us for a second.

So you were a very early adapter and you really understood what is the change that is happening and you knew that you want to jump on this. But share a little bit around the pivot that you needed to do, the experimentation that you needed to do in order to find the market fit, which is always just such a hard thing to do because everything looks so green. We started on this idea of the competition website, and we quickly realized we needed a two-sided market. To make it a real business, we'd have to have a lot of people who wanted competitions. And then we'd also need a lot of filmmakers to do the creation of the content.

Well, which brands do we know? Well, we don't know any of them. Like we're just going to college. Like, are they going to talk to us? And so pretty quickly, we're like, this is not a good idea. Actually, this is a bad idea for us to do. But we got off of that idea. And then we went towards our next idea, which was, was well let's still help filmmakers maybe what we can do is just help them get their video online help them build a portfolio this is an idea that makes a lot of sense because there's been a bunch of companies that have done this successfully we started doing it we built a portfolio builder we built the video hosting part of it and then we launched it and started trying to get people on it. We got maybe like 500 active people using this thing, which at that time, again,

I thought we'd be doing this for six months. I thought it would go viral. Side note, we did some side projects that did go viral. So we had actually experienced that. And this was not viral. This was like slow steady getting more people on there. And we started thinking we need to make money because how are you supposed to survive? We didn't raise money at this point. And my co-founder and I are like a year out of college when we started.

And the only reason we could survive is we were living in a 10 person house and it was so unbelievably cheap. My girlfriend and I split a room and we split food with everyone in the house. This is real. My total expenses on food per week at that time were $15 a week. Oh my God. I spent $60 on food a month and my rent was $320

and I bought nothing else. So basically I was living on $400 a month. And my co-founder, Brennan was basically in the same spot. And that is the only reason we were able to start the business. We got our expenses so low, but we still were gonna rent out of money. And so we had the same spot. And that is the only reason we were able to start the business. We got our expenses so low, but we still were going to run out of money. And so we had the portfolio site. We're like, oh, if we put ads on this,

how much money could we make? And we'd had a thing go viral that we put ads on. We made very little money. We're like, hmm, this might not be the way. We tried to talk to the people who were building a portfolio. And they're like, this site's cool. Like, what am I going to pay for? You already gave me the thing.

It's like, hmm, this doesn't seem good. The one thing we were doing that I would highly encourage anyone who's at the early stage to do is we're just going to a lot of meetups and meeting a lot of people. And so every month we're going to a couple of these things at least and just getting out there and talking to people

and saying, everyone has their business card and says what they're doing. And we're like, oh, where's the video guys? We're trying to do video stuff. And then people would be like, can you help my business with video? And we'd be like, no, we help artists. We're not in the still businesses.

Let me tell you, when we were like three months from running out of money, we started talking to the businesses pretty quickly. And what we discovered was that some of the things we had built were actually quite valuable, but not in the way they were packaged. So we built the video hosting. We built a private way for people to share videos. And that was so that I used to edit movies that I'd send ship DVDs every night and didn't make sense.

Why can't you just put it online? So we solved that problem and people saw that. And they're like, that's interesting. Just this private secure way to share stuff. But they weren't filmmakers. They were companies. And so we went into our first potential customer, told them we could give them this thing to privately share video, made up a price. And they said, if you can give this to us, we'll pay you. And so we did it and they paid us and that's how it started. And it was like one new customer each month at the beginning, which again felt painfully

slow but looking back on it was actually kind of fast. There's actually a need. You're actually creating medicine versus a vitamin. People actually need it, willing to pay, et cetera, et cetera. And the thing that opened our eyes was we were quickly talking to huge brands. Our first customer was a medical device company. They started talking to PBS and we started talking to production companies. Our second customer are like fifth customer Cirque du Soleil. And they were using us to share videos privately of people who apply to be in Cirque.

So it's like fire breathers and gymnastics would upload it to Wistia and then their team would look at it and it was like it's so crazy to me in hindsight that I mean I remember so vividly doing the demo to them sitting on the foot of my bed in this 10 person house. Brendan's upstairs in his bedroom. There's no video. You can't see anybody at this point. So stressed as I'm doing the demo, you know, just like can't believe that I'm tying these people. And they're like, this looks good. I'll do it. I was like, oh my gosh, this is amazing.

I mean, we couldn't even take their credit card. We were like faxing things to close deals at that point. It was ludicrous. I love this story. And then you need to go raise capital, right? Which is very, very hard. Can you talk a little bit about it? Because again, I think there's a little bit of a myth.

We see all these people raising millions and you're like, okay. And then, you know, just so hard to continue when you get the first few nos. We got to about six or seven customers and we realized, okay, this is gonna be bigger than we thought. But we need help and we're figuring out everything ourselves and brendan's building everything himself.

I'm doing all the sales and marketing i'm like blogging two times a day i mean it's not that different from now and sex just kind of funny but. We're like we need help and throw those meetups are going to meet some people we really liked who seemed like they believed in what we were doing. And we started realizing, hey, maybe we should hire two of these people. The sales guy and this engineer, we need help on building the product faster, an engineer would be good. And then we need someone who knows how to sell, we think. And actually, he closed a deal before he even joined the company. He sold a Wistia account to prove to us that he was going to be a good hire. That's a good hire by the way. They were adults and we were children and so they needed a real salaries.

We basically now are covering our basic living expenses. So I'm getting $400 a month. The bread is getting $400 a month. We've not changed our living expenses. We're saving money on top of that, which is an incredible feeling. But I can't hire someone for a hundred thousand or something. So it's through wanting to hire them. We think, okay, if we hire people, we'll go faster.

We should raise money. And so we set out trying to raise angel money. And I quickly found my way to one angel investor, this guy Ashton Piri, and he was super interested and asked a lot of good questions. And he also really believed that we could take this a very long way. It was surprising to meet this person who was like, of course you could take this, this is gonna be massive.

And I'm like, oh, you think this is gonna be massive? He's like, oh, this is gonna be huge. This is gonna be so big. He got excited and then we just hustled our way again, randomly through the community, meeting random folks. But it probably took us five months or so to close the first round. And the interesting thing was like we'd show the deck and which are current customers show prospective customers. And on the list of prospective customers was HBO.

And we're talking to HBO about them using us for all their dailies, which no one could believe me as a filmmaker. I could not believe this. It was insane. I remember when we first started talking to them, I didn't really believe it was them. They said, we just want to try the product. Okay. And they start uploading footage in and we go look.

And it's footage from the Sopranos that no one's ever seen. Behind the scenes footage of the Sopranos. That's the first thing that gets uploaded. What that meant was it was extremely attractive to angel investors. When they saw this, they're like, oh wow. These children are like talking to this company about the deal like this.

And by the way, the quoted size of the deal was like $750,000 a year. So we looked at them like, this is just, we just got it made. This could happen so fast and all this kind of stuff. And without going too long into this story, we eventually actually had to walk away from the deal right before we were going to close the angel round.

And we had to walk away from it because while they were really interested in what we were doing, they were like, hey, for us to use this, it needs to be on premise. It needs to be in a closet basically at HBO's offices, which is terrifying to us because it was all in the cloud and we'd never done a deal like this. And we realized that if we were to do that, we would probably have to move to LA. And that was the only way we'd be able to support it. And then if we were to move to LA and we just got the movie series, like, is this really going to be that big of a market?

And we were just like, oh, this is well, it sounds amazing. So we decided to say no. And I remember the feeling of going back to the angels and telling them, we said no to HBO. And I remember the feeling of going back to the angels and telling them, we said no to HBO. And I thought no one would write a check. And again, I think this is one of those moments that it took many years for me to realize that's probably why they wrote the check,

was we actually had conviction of what we're trying to do, which was build this thing for SMBs and not go do it on-prem and whatever. So yeah, I could go on and on and on about that. But it was very hard, but also in a way, it was just being honest, I think, about where we were and then being optimistic about what we believed, but also saying it might not work. As a co-founder, when you start a company, you need to, or even when you just lead a company, you need to make some really hard decisions and you're never need to, or even when you just lead a company, you need to make some

really hard decisions and you're never going to have all the data you want in order to make the right decision, but you're going to have to make those decisions. You made this big decision in order to basically scale the company. How do you look at scaling the company? The thing that I underappreciated back then that I appreciate now is that a lot of times we don't realize how long it takes before something works. I was talking about this before. You think it's going to happen really fast and often it's like you have a good idea. It often takes a lot longer than you think.

But once it's working, there's usually a reason why. It might be that you have a great brand and an easy to use product in a market that's craving this, like that's the hole in the market. It might be because you have the cheapest solution to an age old problem that everyone understands. So if you come in really cheap, they're going to pay attention. It might be they're doing something completely new that no one's ever seen before and it causes like a different person to be the buyer or something of a product and it could be changes where the budget is whatever it is often we get something working and when growth starts to happen.

To keep growing you often just have to keep doing that thing it's just how it shows up and how you have to accomplish it is very different do you want to to stay focused on what's different and unique, but the how you get there might change tremendously. And so what I think we didn't really appreciate at the time was that what people wanted was something really easy to use and something that anyone who was using video could use confidently. We did a lot of different things, but if you look at where we are now, that's basically exactly the same thing that we do today. When things started to take off for us, it was when we started having a lot of fun in our brand and we started being ourselves. We were transparent about the fact that we were a six person company when we were later six people. We made fun, silly videos, which was the counterintuitive thing to do because businesses are serious and B2B is serious. So why would you trust a company that's making these fun, silly videos?

It's like, no, because we're actually authentic. I'm afraid to share who we are. That is attractive. And that worked in our market. It also meant we're using our product in the marketing. And you look back and like when I pull the thread, it's like the same exact thing today. But it wasn't obvious then that those were the things. It was like those things and 15 other things we were doing.

And the hard part was sorting through which of the pieces are actually driving growth and which are actually not. So when I think about decisions around what we're going to do about what we're going to build, like any big decision, I try to look at it through that lens, how can we keep delivering on the thing that caused stuff to work in the first place? And how do we stay focused? Focus is the hard part usually. But the last piece is the way we deliver it's very, very different. The products different, the brand is

different, the content is different, the people is different, spend more on ads, all these different types of things. But ultimately, the thing you're delivering stays the same. And I want to go there for a second with you, Chris, because I think a brand is something or some kind of a balance between what you want to be perceived in authenticity is really confusing, especially when you're talking sometimes to these big brands, you want to sound very serious and official versus fun and engaging and happy, weird videos. How do you make sense out of it as a leader that on one hand people tell you, you will not be fired if you're in IBM, but you will be fired if you're a startup coming in, right? And you screw

up. So how do you balance it? You landed on the fun, authentic side. I think it's whatever needs to work for your market. If we were doing outbound sales, and we're selling enterprise deals, you see people do wild, crazy things to try to get someone's attention. But ultimately, if you're selling a massive deal, you're helping people decrease risk or manage costs or increase revenue, they have to believe you're going to do that. So a brand that has them believing that is really important. And I think for us, what we found is that a lot of people knew that they needed to use video, but that they're afraid and they're particularly afraid they're going to hurt their brand. That was one of the most common things we heard was like, Oh man, if I use video and it goes poorly, it's going to hurt my brand. That was one of the most common things we heard was like, oh, man, if I use video and

it goes poorly, it's gonna hurt my brand. I still hear that all the time. People afraid to get on camera, exactly as you're saying. And so if we can show you a reverent, silly, funny, but educational things, and you can kind of subconsciously realize, like, for example, we have a campaign right now that's called Webinar Wizard. And it's a song. and it's an incredible song. It's really amazing.

You can see if you go to wis.com slash webinar wizard and we're doing all these ads of this thing and there's a wizard dancing around and the song gets stuck in your head. This thing, if you see it, you're like, wow, this is silly. This is absurd, but it's amazing. I get it. If you can put that together subconsciously, no, like, hey, if they can do this, then what can I do? That's permission almost to use the product, right? And we're doing all the stuff,

I didn't understand the connections earlier on to how much, what we really need to do with our brand was give people permission to market in this different way, show themselves in a different way. And then if you use Wistia and you feel like this is a place you can do that, then we're delivering, right? And so it just depends on the customer. And I guess that's my point.

If you have something that's working early, what you wanna do is just pay super close attention to why is it working. If you could figure that out, then you could scale it. And what I'm hearing also is your growth as a leader, right from somebody, right from the dorm rooms, basically in college, and suddenly running a 200 people team, et cetera, et cetera, multimillion.

What do you feel helped you grow as a leader to be able, with your money mindset, suddenly dealing with a lot of income and revenue, etc. debt sometimes, right? What helped you grow there? On the money side, you basically figure out that in the early days, we're making decisions a lot of times the decisions scare you. You're like, oh man, this really needs to work.

And so you feel this commitment to the decision and the product or whatever it is you're doing. Turns out you still want that feeling. You crave that feeling. And so you feel this commitment to the decision and the product or whatever it is you're doing. Turns out you still want that feeling. You crave that feeling. I think that's really important is, yeah, the business gets bigger. So those types of decisions are bigger and the risks you're taking might feel somewhat similar to the early days. Not the same.

It's not life or death the way it is early days often, but it is often the difference between growth or not. And so you start to search for that feeling, get comfortable with that feeling. I think the other thing is when you're in it, it's very hard to know if you're doing the right stuff, but if you do it long enough, you end up training your intuition. Brandon and I like to say we had instincts

that turned to conviction through failure. So we'd have an instinct on the ways we're making decisions on things we put in the product, on how we decide to launch products, on almost anything. And then when we'd go against our instinct and it wouldn't work, go, ah, even though it was the first time I was doing it, my instinct was actually right.

So now it's moved from instinct to like, I have conviction. Like this is the way. And I think that there's gonna be a lot of things like that in your business where you need to hold the line on a hard decision where you don't have data or results for a long time. Often the most valuable things, they don't happen quickly. They take a long time.

And so having conviction to stick with your approach is really, really, really important in those cases. And in early days, you know, it's trial by fire. And so often you have to do that. When you get bigger, you often don't have to, you have more options. And that actually creates more choice. And that can be a problem because you can lose focus

or not take things as far as you should. What you just said, I had to write it down because that happens a lot in hiring. That happens a lot with different growths in different directions. Hiring is classic mistake zone for this. Right. But as a leader, how do you balance between on one hand, you want the chaos, you want the speed, you want the creativity, you want to let your teams get freedom, but on the other hand, you need to drive results and not throw spaghetti

on the wall. How do you see it as a leader? Yeah, the way that we do this now is we're trying to be really clear about our strategy, our mission vision, where we're going, who our target customer is. And then we have a big list of assumptions that we're constantly testing. And we're making plans based on the assumptions. And as we make investments, we say, are these assumptions working or not? And

like, there's a constant learning element in the business. And then what we do is I found actually what you want is the right structure. So you want to give people the right structure and ownership so that they can actually work creatively to solve the problems that they're working on. And so for us today, what that looks like is we have OKRs, we have like a three year goal, and then we have OKRs for the year that ladder into that three year goal. And they are basically are all customer problems. And so we don't presume to know the solution in most cases. Every once in a while, we'll know it. But usually we say we don't know what the solution is. We just know it's a really important problem to solve. And so then what you want is a team that

can stay on that problem. And what I've learned over and over again is if you get a group of smart people, you get the right balance of a team. They're creative, they plan, they're thoughtful, they learn really quickly. Then basically what you need to do is get it out of their way as much as smart people, you get the right balance of a team. They're creative, they plan, they're thoughtful, they learn really quickly. Then basically what you need to do is get it out of their way as much as possible and say, the most important thing is for you to ship consistently. And so we encourage everyone on our teams

to try to be absolutely shipping constantly. Product teams ship every two weeks, go-to-market teams are responding to that. So every day there's new things going live in the product every single day and we don't necessarily know which of the things are going to be the biggest or the most impactful but we do know the customer problems we're trying to solve and those stay the same as we constantly ship through different solutions. And so really it's about speed and the way you get

the speed is by creating enough structure and ownership so that the teams know, hey, I have freedom in this lane. And then what we praise is fast shipping. Which I love because that's how you learn, right? That adaptability, that experimentation, you get the feedback really quick instead of, I still remember some of my enterprise companies that I was with. We had the requirements and nine months or 12 months later, something would ship and the requirements probably already changed. So I think that agility is really critical.

It's also just this basic assumption of like, we don't know all the answers. So if you don't know all the answers, like let's say you're 50% right, 50% wrong when you make decisions. Okay. If you launch one thing a year, that could be bad. You might have a year where your thing just, your one thing sucks. So instead, if you could break into smaller pieces,

then maybe you can actually ship much faster, you waste less time, the speed of learning goes up, and ultimately the pace of improvement is much faster. It actually took us a long time to figure this out of how to do this at scale. And now it's crazy, it's unbelievable. If you were to look in our Slack and see what's happening, every single day, there's new things go out the door.

Tons and tons and tons of new things are working incredibly well. And when I go back to what input drives this output, it is shipping customer value every two weeks. Chris, could you share a hard moment? Because again, you're running this big thing for many years now. What was a hard moment that you needed to catch yourself? There's been a lot. So the first hard moment I think about when you say that,

after we raised money, we had 10 paying customers, we had this amazing forecast. I was pretty sure that in two or three months, we're going to be profitable. And then we didn't close a single deal for like four months. And that was hard. That was painful. Right at the last second before we raised the money. We were working on this one bigger deal. It was like 10,000 a year. And we closed it. It's like, ah, this is going to be what every deal is like. They're all going It was like 10,000 a year and we closed it. It's like, ah, this is gonna be what every deal is like. They're all gonna be like 10,000 a year. So then that summer, we just raised the money. We had all these new investors like,

oh, let's look at you all. We're like, yeah, we're going enterprise. We're gonna do 10,000 a year deals. And so that's what we tried to sell that summer and basically couldn't close a single one. And the guy who joined us to help with sales, I remember vividly October of that year, he's on the phone with somebody.

He's like, OK, yes, you're going to do it. Fantastic. That's amazing. I'll send over the order form right now, click. And we're like, oh my god, we broke our drought. We got a customer. But who's the customer? And he's like, oh, remember that machine company

I was telling you about, this machine and tooling company? We're like, yeah. He's like, well, the marketer there wants to use this for his kid's hockey team. And we're like, oh, okay. How much is the deal? He's like, oh, I sold it to them for $12 a month. And we're like, oh, you know, it's just like,

this isn't gonna be good. And at the time we had this sheet, we were all in person, a sheet on the office that showed every day in the month and like how many deals. And Brendan went up there and he put like a little line and it was like $12. And we were losing $40,000 a month. So our goal was to get to break even. And he was like $39,988 or whatever. And that was pretty rough.

But the funny thing is, of course, we realized we need to give ourselves more flexibility. It's too early to pick just one size customer. And so the person who's doing sales starts testing more pricing. And we start closing deals at $100 a month, at $150 a month and yada yada. And then eventually by that next summer,

we have 30 paying customers. We're like, okay, this is better. And we make a change. You could find the price online, you could sign up online, it would start at $79 a month. And that summer, we went from 30 paying customers to 200. And I remember thinking, Oh my god, we finally done it. This is it. And then I got a call from our lawyers and they're like, hey, remember that funding round you raised? We never sent you the bill, so you need to pay us this bill now. And it was a $40,000 bill, and we had like $75,000 in the bank.

So half our money was going to go, and then we were going to have payroll, and very quickly we were going quickly run out of money. And so it was like one hard moment, okay, over at the nether, extremely hard moment. And we were just really fortunate that that summer had turned out the way that it did because I went to one of our angels. I was like, hey, I've got good news and bad news. Here's the bad news. We're going to run out of money. It happened really suddenly. We got this huge bill we weren't expecting. But the good news is, look at this customer graph.

I think if we just keep doing this, it's going to work. He looked at this and he was like, you're right, and he wired us a check for $100,000. Then he said, Chris, I want to fly you around on my jet and I want to help you close this round because I don't want you to waste any time. And we went around and basically within a few days, closed the round. And that was the last time we ever raised equity.

Oh my God. I mean, the roller coaster, how do you even get up in the morning and keep on going? What do you do? It is a roller coaster. You start to love it, I think is the thing actually. You start to realize that a lot of the hard moments, what it takes is focus and commitment and working with great people.

And that's how you get through hard moments. Sometimes the hard moments are short and sometimes they're really long. But it basically always comes back to if the culture's right, if the people you're working with give you energy and if those people believe in what you're trying to do, it's a lot easier to get through the hard moments.

First of all, you've been around for a while, you had an exit opportunity, you decided to decline which is insane or not, but tell me what made you decide not to sell. Basically, we had to sell the business. Three different companies trying to acquire us. Brendan and I talk about all the time, and we eventually start getting to what would we do if we sold? Okay, well, it's a life changing amount of money. We'd not have to work again, but would we work again? Well, we'd work again.

The two of us would work together. That's clear. We have a unique partnership. We're still best friends. We've been best friends from the beginning. By the way, the way you do that is you put your friendship first, which actually matters, because then you show up and you care and you give each other hard feedback and all that kind of stuff. Counterintuitive thing.

But anyway, we'd work together. What type of market we get into? Well like we'd get into this SMB market. We think it's underserved. We would still focus on video where this is like 2016, 2017. And it feels like the tech around video is changing tremendously. Like it's getting cheaper and cheaper to make videos. And so there's more ways that people can use videos. So like, okay, we'd do that.

We'd focus on a company where we could be really creative. And we'd run the business really profitably because we at that moment, we're not running profitably, we'd run profitably for many years after we got traction. And then we ran at a loss trying to grow faster. And we admit to ourselves in this moment that it's not working, we're both unhappy. And the thing we would do is we just basically trying to rebuild with you. That's what we do if we sold the company.

So it seems very stupid to give up on this company 10 years in when we're still in control, we could fix it. And so that is what led us to say, hey, actually, let's not sell. Let's just get this business back to a better place, to a place where we feel like it's creatively fulfilling, but also we think that's gonna do better. Let's get back to being profitable that we think that counterintuitively, that's actually gonna let us be more long-term focused, more patient in our investments if we're profitable.

And we think it'll probably be more fun. And so worst case scenario is if it doesn't work, we're gonna have to sell the business anyway, but at least we'll have tried. We bet on ourselves in the first place. Let's bet again. And so we got really excited and I think this is an interesting point here because we got so excited and actually the reality is look We're still losing three hundred thousand dollars a month at this moment Bank accounts going down. We have lots of things that aren't working the business You would think this was like a bad moment and you would think

this would be very stressful like on the roller coaster. This should seem like the bottom and it kind of was but the thing that was funny is what turned it around was instantly having a plan. We're like, ah, we're going to raise debt and actually because we're not going to sell we're going to buy back control from our investors and we're going to get a return for our employees. It'll be like we sold, they'll all be happy.

But for us, it's going to force us to be profitable. And we think that's the right thing for the business. And so we basically are signing on a take on debt, running at a loss, have to turn it around. And I wasn't stressed because I had a plan. I was sleeping really well, I was really relaxed. And so that was funny. It was like, oh, having the plan is the important part.

And then we went and enacted the plan, raised the debt, 17 million in debt, did the buyback, got the business back to being profitable pretty quickly. And then, of course, the focus on the other side of this allowed us to get much more profitable than we were expecting much more rapidly. The team suddenly we'd done something pretty polarizing and that meant that everyone who was there really wanted to be there. And we didn't understand that there are people who are there for the wrong reasons.

And so suddenly the team felt much more unified and excited. Hiring when we start hiring and got much easier. It was like all like upside down backwards. And it was just basically having conviction about what we actually want to build. Worked out better than I could have imagined. That's incredible. And I think not only from the business side of view, but having that plan, also, you started being very intentional about the life that you want to

live together with this business. Can you share a little bit because I think that's super interesting. I remember my wife was like, so you're not going to sell? I was like, no. She's like, you've told me for a long time, you're going to sell this business someday. And we're waiting to do stuff until he sells. I was like, uh-huh. And you know what I decided was, what

if we act like we sold? Instead of selling, let's act like we did sell the business. What would we do? And what we got to was, maybe we should really start taking very real vacations and taking more time off and really giving more ownership and responsibility to more people on the team. It was interesting timing for me because my first child she was probably one and a half when this all happening and so I was like yeah I will take more vacation I'll spend more time with my family and.

Of course again what ends up happening is you start taking more vacation and it turns out a oh, a lot of people didn't need you for certain things. So I would come back from vacation and people would have made all these decisions that previously I would have been involved in. And guess what? They mostly made great decisions. And so what does that mean? I get less emails now and I'm in less meetings. The team is growing and people just start taking more responsibility. I didn't understand how vacations kind of cause people to take more responsibility.

And also sometimes things didn't go well. And then you figured that out and it was like, oh, I'm holding this thing together. And I didn't realize how much I was doing that. And so, yeah, all these, again, just really counterintuitive things. But then when you start living a life while having a business, you start realizing it's actually really easy to keep doing this. The way I would sum it up is building a business is stressful. It's just like trying to get in shape or get really strong or something.

Go to the gym, lift a bunch of weights, you stress your body. If you just keep lifting every day and you never take a rest, you literally don't recover and you don't get any stronger. But if you actually take rest, you do. So what does it look like at work? You get stressed. But if you actually take weekends off and you actually take vacations, you recover. And guess what? It becomes easier to handle more stress, you're training your body, you're training your mind. And so I think that's, again, one of the things that people miss is they go way too hard, especially after the business is up and running. And then they

burn out. And so if you take actual breaks, you don't burn out. And this is different than what I was doing at the beginning, to be clear. I was working every weekend, I was working at nights, I was doing all that stuff. But once we had enough momentum, I was able to add in the time and it had a tremendous impact.

And I love that distinction, right? Because I think there's also this myth of, let me just sit on the beach all day and create freedom and success. That doesn't happen. You do need to work hard. But sometimes we say life is in phases. Different things will be important for you in different phases of your life.

It just go all in whatever it is. But you also had and I'm just curious where it stands for you. There's always this do you build the brand of the business? Do you build a personal brand? Where do you see that? Because I think you also shifted a little bit and I think it's super fascinating to me. Early days of Wistia, I was just like constantly posting.

I said before we had this portfolio site, I was like, what can I do? I was like, I can build a blog. And I posted twice a day and made this creative arts blog. And I had, again, had no idea how successful it was. I thought it sucked. And I had thousands of people subscribing to the newsletter reading all the stuff. You know, I was like, oh, okay.

Like Lynn Heights. I was like, that was I didn't realize that happened there. And then when we figured out Wistia, I was basically sharing the story on Twitter all the time. Like we did this thing today. That thing, you know, it started with like what I had for lunch and it turned into, here's this product feature, we're thinking about XYZ. And that worked, I thought, but I wasn't really sure how well it was working.

At some point, I stopped doing it, probably like 2019. I was like, I don't really feel like this is worth my time as much anymore. So I stopped investing in it. And then COVID happened and I really stopped doing it. And then in 2022 or so, I felt like, wow, we are executing really well. We have set off on this bigger, broader strategy. WISD is no longer just hosting an analytics platform.

We're building editing tools. We're building creation tools. We're building a webinar platform. We're building group recording. We have all these things now, but we're building them then. What can I uniquely do? What can I do that just I can do? And I started thinking,

I can tell the company's story in a different way. I can tell the company's story from my perspective. And I used to do that, and I think it was working, and I just didn't keep doing it. And so in 2022, I started posting a little bit on LinkedIn and posting about Wistia, but posting about my life as an entrepreneur, posting about what it's like to be a parent as an

entrepreneur, posting about some of my other interests. And a lot of stuff took off and I was like, whoa, look at these interactions. And then over time I've invested more and more in it and realized some really interesting things about building a personal brand. It's shifted how I think about brand building. Where I still think there's a place to be building a company brand. I think you're crazy not to be

building a company brand. But the expectations for startups for those brands keeps getting elevated. Distribution is free, but that means you're competing with everybody. So you're competing with Netflix, you're competing with viral YouTube videos, you're competing with games, you're competing with everything as a company brand. And we're also as a society being trained to trust company brands less. And actually, if you look at how we're spending our time, we're spending our time on social media where we trust individual people. And I think this is rooted in something that's always been true, which is if you have a group of friends and you have your techie nerd friend, you ask them tech advice. You have your friends willing to soccer, you ask them soccer advice. That's how it works. You have friends, you ask

word of mouth. But now it's possible to build these relationships with people in kind of a parasocial way online. And so we have our friends in person and we have our like online friends who we trust on different topics. But on the B2C side, this has become a tremendous way of how we discover and learn about products. It's becoming the dominant way. And so what I realized is starting to really happen on B2B too. And so it's kind of fortuitous that I looked at this telling the company story approach thing on LinkedIn. Because now the content that we post on my LinkedIn gets huge numbers of organic views. And it's not all whiskey. It's like 10% whiskey or something. But some of it is. And it's very different how it's engaged with.

If we post something on my LinkedIn, people ask questions and give feedback in a way that is very like you would talk into a person. Then on the company page, people will be like, this is cool. They'll like it, but they don't give the same kind of feedback and stuff. And so I realized basically we all have an opportunity to build both of these things, build the company brand and build the personal brand. The difference with the company brand is you can't get free distribution anymore. All the social platforms, if you want to get your stuff seen, you basically have to pay. But the social platforms, if they basically force individuals to pay, they're going to

lose all the content. And so therefore, it seems likely the individual content will probably continue to be free. So I look at it as paid versus organic, a lot easier to get organic on personal, a lot easier to do the paid thing on the company brand. That's exactly what we're doing. And I think that's just so important for listeners to understand. You might be posting from a business page,

but that usually gonna go crickets unless you pay for it. So if you really wanna build your own brand, that's gonna take you further, but also it's going to paint that more authenticity. If people will relate to you better. And I just love that. So for those who don't know with Wistia enough, why should they use Wistia versus YouTube? I can tell you what we're used to doing, but I'm curious what you say, Chris. Which is a video marketing platform.

Everything we do is about making it easy for you to get more value out of your video and enable you to use video better. So we have a player. That's really the start of the company is like having this player and hosting. The player looks amazing. It's really fast, gives you amazing analytics. There's no related videos. You control the whole thing. You can put your brand and you can add calls to action,

collect the leads. And so it's just very different from YouTube because YouTube is not about that. YouTube is about getting you to spend time watching things on YouTube. And I love YouTube, I'm constantly watching things on YouTube but there's a reason why they have recommended videos. There's a reason why they do that.

It's like they want as much watch time as possible and then they want to put ads on it. And obviously if you're making content that's low in your funnel or you're selling access to or something, you don't want ads on it, you don't want related videos. So that's where the business started. And now the way we've really done is said,

hey, we see that as video has changed it's become much easier for anyone to make a video. You and I are using a remote recording platform. Things like this didn't exist in like 2018. We all see our computer as a camera now. And that has changed expectations for video at work. And so I see all the time, someone says to a product marketer, Hey, can you make a launch video for this? You used to say that you said, say, do we have a budget to shoot a video? Now you say, can you make it? So expectations have changed for video. A lot of our customers are basically their video is a part of their job. It's not their whole job.

And they're using 15 tools to get their jobs done. And so we said, hey, can we just maybe cut that down? Can we evolve with you to be more of an all in one platform? And by doing that, we can save you huge amounts of time in the in between of things. And that led us to basically building an editor into Wistia that uses AI so you can edit by adding the transcript and has music and stuff like that, building recording tools, we have single person recording, we have group recording, we have a social clips tool, so you can take long form stuff will help you find clips and you can cut it down

to put it on social. And then we have a webinar platform. And the way you put these things together depends on what you're trying to do, but we'll see people who they do a live event, their recording is instantly in their Wistee account, they edit it, we see most webinars are edited, and then they can quickly publish it from the same place

or send it to an email list or make clips from it to put on social. And the whole thing is if we can cut down on that time and give you one tool, then you get much more time back, much more leverage, and then often people just end up using video better. Incredible, Chris. And for us, I mean, we use it for a lot of the things

that you just mentioned, the webinars. For those who don't know, if you embed a video from YouTube on some kind of other platform, you're usually going to get other recommendations and you don't want to send people off your own website, right? So this is how we started with Swistia and from that point on, you know, it became a webinar and so many other things. So I just, I personally love it. Chris, based on everything that you've gone through, what would be an advice to your younger self if you could go back in time?

The first thing I would say is be patient. This stuff takes a lot longer than you would think it does or than we're led to believe. But if you can be patient, you can find things that work and you could scale them. Your own imagination is your limiter on how far you can take stuff if you have a business that's online. The second thing I would say is pay attention to qualitative feedback. I think whenever you're doing something new, you always get qualitative

feedback first, which is people saying, I like this, I don't like this. Things getting mentioned when you're in a sales call, the things that someone tells you in person that they wouldn't have told you otherwise. You're going to need to get really good, the things that someone tells you in person that they wouldn't have told you otherwise. You're gonna need to get really good at that because that's how you get to make decisions faster, is you get a lot of qualitative feedback and you parse it down to like, what are they really saying? So I would say really pay attention to that.

And then the other thing I would say is you really wanna trust your instincts. It's so easy to think that other people have all the advice for how you should build a business because they've done something before. And the thing I've learned over and over again is that once you start your company, you are the expert. And I think that's a really hard thing to realize. You might be day in day out on your business. You ask someone else for advice. the advice sounds good. You take it, it doesn't work. You're like, what's going on?

And it's like, no, you maybe knew you shouldn't have taken it because you're the expert at your own business. And I think that's the thing that we all forget. We are the experts at our own business. And that is why, when you can really start to notice your own instincts, when you're building your instincts and things are working,

you should actually trust them. And so that's what I would say if I could go back and do it again. That's really powerful because somehow you have all these experts and the grass always seems greener on the other side and it's just so easy to be tempted to go in all directions. But eventually nobody really knows except for you. But that's also scary to think about that. It is scary. But when you can flip to realizing you're the expert and you can trust your instincts, it is extremely exciting. And it is a hack that lets you go much faster.

Chris, thank you so much for coming to the show, for creating Vistia that we love, and for just sharing this incredible story with our listeners. Thank you so much. Awesome, well look, thank you so much for having me. This was really fun.