Chris Savage of Wistia

Founder Coffee episode 029

I’m Jeroen from Salesflare and this is Founder Coffee.

Every three weeks I have coffee with a different founder. We discuss life, passions, learnings, … in an intimate talk, getting to know the person behind the company.

For this twenty-ninth episode, I talked to Chris Savage, co-founder of Wistia, a leading video platform for marketers and salespeople.

Before starting Wistia, Chris worked as an editor of a documentary that ended up winning an Emmy award. He then launched Wistia with his best friend, with the confidence that a small team could do something impactful.

They together saw the potential of video and started a competition website for filmmakers. It finally pivoted into a video platform that helps businesses work effectively with video.

We talk about how they grew Wistia from 2 to about 100 people, how they resisted acquisition offers and raised debt funding instead, how Chris’ role evolved over time, and why you shouldn’t do anything if you’re not obsessed by it.

Welcome to Founder Coffee.


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Jeroen: Hi, Chris. It’s great to have you on Founder Coffee.

Chris: Thanks for having me.

Jeroen: You are the co-founder of Wistia. For those who don’t know Wistia yet, it must not be a lot of people, what do you guys do?

Chris: We are a company based in Cambridge, Massachusetts, and what we do is we have a platform that helps people market and sell better at video. So our core product, Wistia, we launched a long time ago, and it allows you to basically control and measure the entire video experience of your site, so you can make your videos more effective. You can better understand their impact on your audience.

Chris: We also have a product called Soapbox that’s a Chrome extension that lets you actually make videos. It’s a really simple thing where you record your webcam and your screen simultaneously, and then you can create smooth edits between them. So you can make something that looks professional really easily.

Jeroen: Yeah. If I understand well, what you guys basically do over, let’s say, embedding YouTube in your site, is really making something that is a better fit for marketers and salespeople; where they can exactly see who watched what and when. What else does it do?

Chris: That’s exactly right. We track how every viewer watches every video second by second – what they skip, what they re-watch, so you get a picture of how your audience is responding overall, which can help you make the content more effective in the future. We take that data and we put it into other marketing platforms. For example, we integrate with HubSpot. What that means is that you can take your viewing data and put it in HubSpot, and then you can understand which of the people in your lead database are actually watching your videos. So you can create automations and stuff like that.

Chris: Because we’re so focused on helping you and your site, our player is the fastest loading player on the internet. We do a ton of hard work so that you get the SEO benefits so that YouTube doesn’t. Like, when you embed a YouTube video on your site, what you’re effectively doing is making a link back to the YouTube page, and what that means is that if you have core terms or things that people are searching for that are really important to your business, you’re putting your own page against that YouTube page, and guess what? YouTube does incredible SEO, so they’re always going to beat you.

Chris: So you have to think about the power of video. What is your strategy? If your strategy is trying to get traffic to your website, you’re going to want something probably like us that gives you more control. You’re still going to put your content on YouTube, you’re just going to put it at the top of the funnel. If you are in pure media play where you’re just trying to get the views on YouTube, and then make ad dollars or something, you’re not going to want to use something like Wistia.

Jeroen: Yeah. Basically, okay, it’s trying to make something that is better for marketing and salespeople. Is this the initial thing you started off with as a concept, or has this grown over the years?

Chris: Oh, no. No, we always knew we wanted to focus on video. When we started, we started because we saw that the technology behind the online video was changing dramatically. It used to be really hard, and you had to be technical to make online video work, but very quickly, because of some open source tools, it was going to become very easy.

Chris: We thought this could be a huge opportunity for video on the web, and the initial idea we had was we would make a competition website for filmmakers. We were going to try to have a company, like a big brand, sponsor a competition where filmmakers could make an ad or a trailer or an episode of something or what have you, and we’d try to connect filmmakers and brands, and the hope was that the filmmakers would get a lot of publicity if they won the competition. The brands would get a lot of goodwill because people were doing the competition.

Chris: We were excited about that, but we got a few months into it and realized we don’t have any connections to brands. It was going to be really hard going. It’s a two side market problem. So after three months of starting the company, we were trying different things, and it took us about a year to realize, businesses are going to start to use video too. They value their time, and will spend money to solve problems. Maybe we should focus on that.

Jeroen: Yeah. Makes sense. It’s like, before, you weren’t doing anything with video, or it just grew on you at some point and you started Wistia?

Chris: Yeah. My dad is a computer science professor at Brown University, and he’s a huge early adopter. So I grew up around technology. Getting a DVD player the day it came out or getting the Microsoft Flight Simulator the day it came out, and all of those things. I remember when we got the internet in fourth grade, and I was just enamoured with it. I was spending all of my time on it. Then in college, I ended up focusing on doing film and video, and my dream was to make movies. So what ended up happening, I think, it’s like those two things combined into what Wistia is.

Jeroen: Yeah.

Chris: It’s funny, because even today, we made this huge piece of content last year called 1-10-100, which is a feature length documentary in four parts. It’s an hour and 42 minutes long. It’s been really fun to do, really well received and it just won a Webby. It’s like, wow, this is what I dreamed of doing 15 years ago. I just didn’t think it would happen like this at all.

Jeroen: It’s basically a few pieces falling together, in terms of background and your passions. It seems like a great founder-startup fit.

Chris: Yeah. Also, my co-founder and I were best friends before we started the company, and have continued to be best friends. We love working together, and we love the process of trying to solve hard problems. That’s what gets us excited. It’s funny, because even in the first year, we made no money. We just subsisted on almost nothing, because we were living in a giant house that had a million people in it, and it still was really hard going for many years. But even though we were making no money, or then very tiny amounts of money – we couldn’t afford a new printer at one point; we loved the challenge.

Chris: The cool thing has been, that I would have been doing this for almost 13 years this June, and the challenges are still super fun. So it feels like this very fortunate thing that we found actually pretty early on, that we like solving these types of problems, we like creative thinking, we like being in charge so that we can screw things up and it’s okay, and we can try and create a place where other people can feel like they can innovate too, and are encouraged to do so. So, yeah, I feel very fortunate.

Jeroen: Right. I’m on your LinkedIn profile here, and it looks like you only had one job before this, for about three years? Correct?

Chris: Yeah, yeah.

Jeroen: And that was in movie making.

Chris: That’s right.

Jeroen: Cool. How was the jump, exactly, from being an editor at Big Orange Films to starting your own company?

Chris: It was interesting. That company, Big Orange Films, did this documentary, and I started on the documentary as an intern. So I never really made much money when I was there, it was very, very meagre. We were a very tiny team, and while I started as an intern, at that time, to do the editing, you would record all the stuff. We recorded on DV film, but you didn’t want to run the DV film through the tape player too much, because it would actually ruin it. So every time we shot an interview or something, we would copy it to VHS. I would take the VHS and I would rewatch it over and over and over and transcribe all the interviews. I manually did that for a summer.

Chris: Then we took the interviews and we started to try to edit together the story from those transcriptions, and I just wouldn’t really go away. I was in college while I was doing this work, so I just thought it was really fun, so I ended up shooting interviews and editing and ended up being one of the producers on that project. We actually did really well. We won an Emmy and won all these film festivals and stuff, and it was incredible to be a part of this super tiny team and see what we could do. It was fundamentally three or four people really working on that movie, and yet with these three or four people, we were able to make something that people really liked.

Chris: When we jumped into Wistia, I had that confidence that a small team could do something impactful. It didn’t really occur to me that Brendan and I wouldn’t be able to be successful, because it felt like, well, if we could work on this movie for a while, we could do this too. That wasn’t even my movie, and I was trying to convince someone else that the things I thought were the best things to do. In this case, it was like, well, Brendan and I are going to be in charge. We can do whatever we want, there’s no one stopping us. That will probably be really fun, and we assumed we’d be successful. We actually assumed we’d be successful in six months and we’d sell the company, and obviously that didn’t happen.

Chris: But, yeah. It was an interesting transition. Part of it was really easy, and part of it was really, really, really hard, because we were doing something completely new, figuring out everything by ourselves, and things were much slower going. They took much longer than I thought they would.

Jeroen: If I hear it well, your initial motivation of starting Wistia was working with a small team, making something successful, selling it off. How did that evolve in the meantime? How do you look at building Wistia right now?

Chris: Yeah. That was the initial goal, the point of starting the company was to sell it in six months, and after a year of not really making much progress but really enjoying it, and a few more years later after raising some angel money and getting customers and still being tiny but really enjoying it, things just started to shift. We started to realize, it’s not about the end. It’s not just about the outcome for us of selling a company or something. It’s actually the journey of building it that is the fun part.

Chris: We faced a really big decision in 2017, because we had three different companies trying to acquire Wistia at the same time, and if you’re running a tech startup, people will poke around, and there’s lots of different ways to get acquired. We’d always just ignored all of those people who were poking around. But in 2017, the company was probably 80 people. We had been pushing really hard to try to grow revenue, and we had been actually acting like we raised a lot of money. We had never raised a lot of money. We only did two angel rounds and raised $1 million, but we had become profitable and we saved up money, so we were reinvesting everything into growth.

Chris: As these acquirers came along, Brendan and I started talking to them, and then actually got some offers and were sitting there with an offer, thinking, oh, maybe we should sell the company. It was interesting, because when you’re faced with that decision, you think that’s why we started the company. That’s why most people, when they talk about doing startups, aren’t talking about it for the journey they’re going to be on. They’re talking about it for the exit. You raise money to get acquired.

Chris: So we were sitting there facing this acquisition offer, and realized if we sold the company, we would try to do our time at the company that would buy us, which was going to be two years, and then we’d probably go and we’d work together again and we’d start up something new, and we had an idea of the space that we’d work in, because we feel like there’s other problems we’d want to solve that we hadn’t solved. But an idea of the type of culture that we’d want to build and the type of brand and who we would want to hire, we realized we would try to rebuild Wistia.

Chris: It was funny, because we thought we’d rebuild Wistia, and we started to realize, what’s wrong with Wistia now? Why are we even considering selling? And we realized we were actually unhappy at that moment, and we were not happy with how we were running the company, the decisions we were making weren’t focused on the long-term enough. We weren’t taking the right creative risks.

Chris: So what we ended up deciding to do was not to sell. But the second we decided not to sell, that actually made us misaligned with our angel investors. We’d only raised $1 million, but they had put $1 million in, and angel investors expect to make money. So they obviously wanted us to sell. We had also given stock options to our employees. So we also told them, these stock options will be for when the company sells, so if we’re not going to sell, we’re going to need to do something.

Chris: So that was June of 2017, and we decided that what we wanted to do was do a deal to take back total control of the company and get a return for everybody, and be clear that we’re trying to build a lasting business. So we ended up raising debt, because we had not been running the business properly. We had been putting everything back into revenue growth, so we didn’t have the cash. We ended up raising $17.3 million in debt, and using that to basically give people an offer that if we sold the business to our angel investors and to the team, they could all get liquidity, and then we told everybody what we were going to do is we were going to flip the company back to being profitable. We told them we’re going to focus on the long-term and we’re going to do creative work. That’s where we’re going to do our best work, and if it doesn’t work out, then Brendan and I will have taken on this risk, but we’ll have taken care of everybody else, because they will have gotten a return, and we’ll have to figure out what to do.

Chris: But we felt comfortable with it, because it felt similar to starting the business in the first place. Taking a bet on ourselves again, and we did that deal in November of 2017.

Jeroen: How many of the angel investors and employees actually wanted their money at that point?

Chris: It was an interesting mix. The angels, some of them sold completely, some of them sold partially. We had a couple who didn’t want to sell at all. That’s, of course, the funny thing about angel investors. You have to have a good amount of money to be an angel investor, so when someone comes back and they say, here’s some money, they’re like, eh, I don’t really need it. You’re like, great.

Chris: With the employees, we instituted a profit sharing program. We said, if you are still a stock option holder, that’s fine. But that’s going to be the way that you’re incentivized, and if you’re not a stock option holder, you’ll get profit sharing. For most people, it was a better deal to then sell their shares and then also get profit sharing, and it worked out incredibly well. I can’t even tell you how well it worked out. Or I guess I can because we’re talking.

Chris: But the funny thing was that once we switched to profit sharing, it made the financials of the business way more real for everyone. We always had disclosed our financials to the team on a monthly basis, and the first time that Heather, my VP of finance, got up there and said, “All right, here are the numbers. Here’s how we did, this is how profitable we were. Does anyone have any questions?” There’s all these hands that shot up saying, “Why are we spending so much money on this? Why are we not spending enough money on that?”

Chris: Basically, you could see how the business was being run would have a very direct impact on yourself, and when you’re building to sell a company, it’s all fuzzy. Are you going to get a 4X valuation on your revenue, are you going to get a 10X or 100X? Well, it depends on what size you are, how fast you’re growing, what market you’re addressing. There’s all these factors. So it’s impossible to understand the value. Then with profit sharing, it’s very possible and very clear.

Chris: So it really aligned the company. Last year, 2018, was incredible. We ended up growing faster than we expected, being more profitable than we expected, and that was all because the team got excited and aligned, and we got focused. We worked on the right things. It was really cool to see it work.

Jeroen: Along the way, you haven’t picked up any equity venture funding? Is that a conscious decision?

Chris: Yeah, that’s a very conscious decision. We never had any venture financing, and the reason is that we were concerned about the incentives being misaligned. If you go look at the venture math, the way that it works is that the people running the venture fund take a fee to manage the fund, but then they take a percentage of the returns, and they have a very long time horizon, which is usually good, which is 10+ years, 10-14 years for an early stage fund.

Chris: So the way that venture guys and gals make a lot of money is by getting really big funds, and then living off the management fees. As long as it looks like your companies are performing well, you can raise another fund that’s bigger, and people believe you’re doing good work, even though you haven’t actually gotten returns yet. That’s the first piece.

Chris: Then the second piece is that the way that the funds work is they need to have a few companies that return the whole fund, that are way more than a 10X return, like a 20X return or a 100X return, and without that, you’re not going to have, usually, a very good returning fund. So, for the venture investors, they’re incentivized to encourage every company to be a 100X company, which seems like a good thing if you’re an entrepreneur until you’re actually running a company and you realize, oh, I can get a 10X on this or a 8X, or I just love what I’m doing, or I want to be more patient or whatever, and a venture investor does not like that. That’s not helpful, usually.

Chris: So they’re encouraging you to run the company as fast as possible, and you’re sitting there thinking, I have a valuable thing. Maybe this could be a $20 million business that I’d love to run, and I can have great products and customers, great experience for my team. I have a big impact on my community. But that’s basically irrelevant for venture investors. So we always were trying to protect our optionality and felt like if we signed up for that, we’d be giving up this thing we were building. Had we done that, I think we would’ve failed, because we would’ve pushed too hard at some of the moments that would have broken us, instead of actually giving us an advantage of being able to be more patient and more long-term.

Jeroen: Yeah. So you guys are in it for the long run, you and your co-founder.

Chris: Oh, yeah.

Jeroen: I would like to ask, in the next 10 years, can you still see yourself working at Wistia?

Chris: Absolutely.

Jeroen: Awesome. If you’re thinking that long-term, where do you see your business going in that period? Where do you see the future of video for marketing and salespeople?

Chris: I think there’s a lot. It’s really interesting, because the market is very large, so there’s a whole segment of the market that we still talk to. It seems crazy, but they’re just getting started with video, because I think video can be so scary. People will say to me, oh, video can be really impactful on your brand, but it also could really hurt you, right? I’m like, yeah, if you make a really bad video, you’ll look like a joke. If you make an amazing video, you look incredible. And that scares a lot of people away until there’s that one person in the organization that says, I think we’ve got to do it, or I trust myself, or I trust this outside production company, or I think that our market will like authentic video or whatever, and then that person takes a risk and then it works.

Chris: So it’s been this interesting thing in our market where it’s actually slowed the growth of the market over the long term, which seems like a bad thing, but for us, we’re so patient that it’s been fantastic. There’s a ton of people who still have to figure out how to get confident using video well, how to get confident on camera. We try to help them with things like Soapbox, and I think we’re going to see more technology that helps you make videos that look professional.

Jeroen: Right. So you’re going a bit away from the delivery and the analytics, more towards helping with production.

Chris: That’s part of it. I think we’re doing that. I think you’re going to see tons of companies attempt products that help you with the production of the video, and they’re going to do more automated creation of video, automated editing, automated filters. You’re just going to see way, way, way, more options for people who have never made a video, and you’re going to try those products and you’re going to look at the video and you’re going to be like, do I think it’s good or not? I think we’re going to see a lot more of that. We’re just scratching the surface there.

Chris: Then I think the way that video is used in this space is going to change, because where Wistia sits today, we help people mostly with the video on their website, and it turns out if you have no video on your website, you’re probably missing an opportunity, because we’re living in a world where expectations have changed, and there’s people who want to read stuff, and there’s people who want to watch stuff, and there’s people who want to listen to stuff. So if you don’t give those people who want to watch something a way to watch, they’re going to move on to the next thing, so you have to do that.

Chris: There’s an opportunity there, and our products are really centered around that. But a few months ago, we launched a product called Channels that lets you build a Netflix like experience on your website for watching videos. We think that people are going to make more content that is educational and entertaining that lives on their site. Something that they can control. If you look at YouTube, Facebook, Twitter, LinkedIn, they’re all really powerful social networks that are constantly changing the rules on you. They’re doing that because they need to monetize with advertising. Inherently, you have to think of those as a collection of audiences that you can try to get in front of, but there are no guarantees. So we think more and more people are going to invest in trying to own that experience themselves, and we’re going to start to see more video content that is basically not just optimization focused, but engagement focused.

Jeroen: Yeah, and also, you keep people more to your site, I guess. Earlier today, I read someone on a Facebook group asking, hey, how can I turn off these YouTube related videos?

Chris: You can’t, yeah.

Jeroen: Because we also see the issue. You basically post an onboarding video or something, a video that explains your software, and then just after your video, they play the competition.

Chris: Yeah. They changed the rules on that five months ago. Literally every single YouTube embed on the internet, if you had it turned off, which you could turn off before, they’re like, no – you get related videos now. If you know what you’re doing, you can set it up so it’s only your videos. The related videos, when you click them, it brings you back to YouTube.

Chris: So it’s like a free service, and whenever you’re using a service that’s totally free, you have to remember, you are the product. They’re using your traffic on your website and your viewers to drive more people to watch things on YouTube.com, where they can serve them with more ads and they make more money. That’s just how it works. When they did that, it was not surprising to me at all that they did that, and people were upset. But it’s been free the whole time. They had to pay money at some point. They’re making a lot of it, but that’s just how it works.

Jeroen: Right. Okay, enough about videos. You guys are now about 100 people, right?

Chris: Yes.

Jeroen: You started off with the two of you?

Chris: Yeah.

Jeroen: How did your role change over time, and how has it changed recently? What is it that you are busy with right now?

Chris: My role has changed a ton. In the early days, my title was CEO, but I was a blog writer, support responder, social media manager, product designer, everything. One of the hardest things about growing is you do something until hopefully you get good at it, and then just when you’re getting good at it, you have to find somebody who can do it better than you – of course, when the company can sustain this. You do that over and over and over again.

Chris: So you’re constantly figuring things out and handing them to somebody else. At some point, you build confidence that you can do that, and that’s exciting. But as that happens, the other thing that happens is that you’re more responsible for communication internally and externally, and thinking longer term. That was one of the surprising things to me in the early days, with just Brendan and I, we had a ton of time. We were just coming up with wild ideas for things we could do to get people to pay attention to us, things we could do to build on the product. You have time, and with that time, you spend it on creative thinking, you spend it talking to potential customers and all that kind of stuff.

Chris: Then everything gets super insanely busy. You feel like you have no time at all, and you feel like you’re scrambling, scrambling, scrambling, scrambling to just make things work. And then at some point, if you’ve given up enough ownership to other people in the company who can do those things better than you, you end up again with time, and the time is actually incredibly important, because you have to think longer term. You have to spend more time doing the stuff you were doing at the beginning, like talking to prospective customers, thinking about shifts that are happening in the market, and it actually is work. It’s the same work that it was in the beginning. It just feels weird because it’s this big transition.

Chris: Today, I spend my time trying to think about where things are going, looking at what our customers are doing, what our challenges are that our customers have, what our partners are thinking, what other entrepreneurs are thinking, and I try to make it hopefully a little bit easier by thinking long term. I try to make it easier to make some of the short term decisions we have to make.

Jeroen: So you’re basically in charge of forming strategy based on what you see and what you hear, right? And then communicating that to your team.

Chris: Yeah.

Jeroen: If I would ask you now what keeps you up at night lately, in the last few weeks or months, what would that be?

Chris: That’s a good question. I am sleeping pretty well right now.

Jeroen: That’s good.

Chris: Children waking me up is probably the thing that gets me up the most. We’re doing a lot of new, big, and different things than we’ve done before, which is exciting, and I would say that I lose sleep when I worry that we’re not thinking big enough, or I think we’re going to be behind on something or whatever. But these days, the company operates so concisely and clearly, and we have clear goals and clear responsibilities and stuff, that there’s not a lot of stuff that keeps me up at night in the short term.

Jeroen: Was it different at any point?

Chris: Oh, yeah. Oh, of course, my gosh. Yeah, there’s been years where we were pushing the business really aggressively and losing money that I was up at night all the time, and super, super stressed out. In the years before we did the buyback. At one point, we built a strategy, and we were like, all right. We’re going to start aggressively losing money trying to grow faster. So every month, even though you talk about investing in a long term thing, if you’re losing $100,000 in February, and you plan to lose $130,000 in March, because you’re hiring and you’re spending more money on advertising and other stuff, it is going to keep you awake.

Chris: If you’re behind in your revenue, and instead of being down $150,000, you’re down $180,000, all these things start to get stressful, because you start looking at that burn thinking, wait a second. We were profitable, we could last forever, and now we’re losing money, and if these things that we’re attempting don’t work, we’re going to lose money even faster, and that’s going to increase the stress. That’s going to increase the short-term focus. That’s going to decrease our ability to do the work that we think is our best work.

Chris: So, yeah. I’ve had years of sleeping poorly, being super stressed. I would just say at this moment, we’re running the business profitably and thinking long-term. It allows you to handle bumps much more easily.

Jeroen: Yeah. How do you think you got from that place a few years ago to where you are now? What are the key things you did to get from there to here.

Chris: The buyback was the first thing, and realigning everyone on what we were doing. Raising the debt forced us to be profitable, which we knew would be a good constraint, and that forced focus and prioritization, and that was all really helpful. That changed who wants to work here, because we had some people who were just here for an exit. They essentially got one, so they left. Then there are people we’ve hired who are here for the journey, so we’re doing better work than we’ve ever done. We changed who was on the senior management team, and we went from a place where it was unclear what that team was to a very clear, very well run team with everybody on it, completely owning what’s happening in their departments. That changed what I worried about, what I could think about.

Chris: So there’s an enormous list of things that have evolved and changed and gotten us to a place where we are. Yeah, it lets me sleep easy at night, which I think is actually important, because that is also the same thing that lets you think about the longer term things, and have more confidence in doing bigger things.

Jeroen: You mentioned that you, as a founder, subsequently have to take things that you’re doing and that you’re good at, at that point, and then find someone who does it better, and always work on delegating the next thing. Are there any things left you think you could delegate at this point, and what would these things be?

Chris: It’s funny you say that. There definitely always is something where I think, how will I delegate this? No one else can do this, and then six months later, I’m like, yeah, someone else can do it. Yeah, I think it’s interesting. Maybe three years ago, we had no one at Wistia whose title was research. So research on the market, research on customers, research on what they were doing was a very shared thing, but that felt like something that I was spending my time on, a good percentage of my time when I had it, trying to figure out, what do people want?

Chris: Then over time, we realized we could actually structure that and have it be a real role, and there’s people who could do that 1,000 times better than me, and my approach was very haphazard and their approach was very methodical and thoughtful. So now we have, I think, three or four people in research, and just a simple example of something that didn’t seem like it could be delegated, and then it turned out it was in many people’s jobs. They could do it far better.

Chris: That happens, that continually happens, and I think it just comes down to looking at how you’re spending your time and trying to figure out, am I delegating solutions, or am I delegating problems for people to solve? For a long time, you’re delegating solutions that you’ve come up with, and then you are delegating the problems to solve, and then you’re delegating the finding of the problems. Then you’re delegating the evaluating of the problems that are found. It just keeps going as the company grows.

Jeroen: Right. Then the next step is the definition of what constitutes a problem?

Chris: Exactly, yeah.

Jeroen: It’s basically, you just have to give away the overall strategy, and you can just let the business run by itself.

Chris: Yeah. The funny thing, though, is even if you give up pieces of the strategy, what you end up getting is more leverage on people who are digging deeper on things coming back. So the decisions that you’re making are inherently longer-term. That also lets you, at least for me, it lets me weather ups and downs much more easily, and have much more confidence in terms of the direction we’re going in. We have lots of competition, and you’ll see them do things that’s similar to something we just did. But it’s like, you dig in a little bit deeper, and it’s like, do they get what we’re doing or not? And it’s like, oh, from how they do it, they don’t know what they’re doing. We know what we’re doing, we know where we’re going over the long term. So you can end up in a really different spot.

Chris: But without that time, without the team, and without the talent of people around you and that process, you wouldn’t be able to do that. It’s just a lot harder to build out that long-term vision that is actually being fueled and updated and evolved based on what’s happening.

Jeroen: Yeah. All these things you’re doing, what is it for you, what is it that gives you energy at this point? Has it changed over time, is it still the same thing?

Chris: I get energy from working with incredible people, and I get energy from delighting customers. I get energy from trying to come up with creative solutions to problems. That, for me, means solutions that people haven’t done before. It hasn’t actually changed. It’s just the mix of stuff, and it’s the scale of the problems. The problems that we’re solving are bigger than they used to be, but it feels similar to when we were 10 people.

Jeroen: But it’s a bit more abstract, I guess. It’s not as direct anymore, where a customer says, I have this issue, and you solve it for them. It’s more taking that on a way higher level and then going across the scale of all your customers and saying, this is a major thing we should be working on. Did I say it correctly?

Chris: Yeah, exactly.

Jeroen: Cool. You guys are based in Cambridge, Massachusetts, you said?

Chris: Yeah.

Jeroen: Are there any other cool startups we should know from around there?

Chris: Yeah, there’s a ton. It’s funny. There’s a lot of B2B marketing and SaaS stuff here. So you have Appcues, which is close by. They’re really great and really fun. Jonathan, their founder, worked out of Wistia for the first year he was working, so it’s amazing to see them do so well. Help Scout was here for a long time and has a presence here. Litmus, Insight Squared, HubSpot, obviously, are here. Yeah, there’s a ton of companies that are here that are full of bright people.

Jeroen: Why do you think it’s so much more tech? Is that linked to the university?

Chris: I feel like it’s like, people always said that the investors in Boston were more conservative. A lot of SaaS, you can do such a rigorous analysis on it when you’re looking through the unit economics, I think it lends itself pretty well to this investor base. There are some consumer companies that have done really well here. Actually, there’s a fair amount of them, like TripAdvisor, Kayak, Wayfair and Simply Safe. They’ve all done incredible. I think there’s something about the investor mix that just lends itself well to SaaS, and SaaS, there’s a lot of marketing in SaaS. I think that’s credit to HubSpot, credit to Constant Contact. There’s just a lot of interesting martech here.

Chris: Yeah. That’s the best guess that I have. If you have a better one, I’d love to hear it.

Jeroen: No, I’m not operating in Boston, obviously. It seems like when I look at Boston from here, it looks like a place with a lot of smart people, with big universities, great research facilities, and all that. It seems kind of logical, I guess, to have more of the analytical part of tech and more B2B. I never thought about the more conservative investors, but it seems like a plausible explanation.

Chris: That’s what people talk about here when they complain about stuff, because obviously, people complain. They’re like, yeah, they’re not so sure, don’t take a risk? Okay. Great. It’s just, that’s what I hear is the complaint.

Chris: We never raised venture here or anywhere, so I’m a step removed from it all.

Jeroen: Yeah, obviously. So, I’ll be wrapping up. What’s the latest good book you read, and why did you choose to read it?

Chris: That’s a good question. What’s the latest one that I really liked?

Jeroen: And why did you read it?

Chris: Why did I read it? I read Shoe Dog by Phil Knight recently, the founder of Nike.

Jeroen: Awesome book.

Chris: Yeah. Really enjoyed that, and I just loved the behind the scenes of how companies are built. It’s pretty relevant to what I’m doing. It’s just normal people trying stuff. I feel like so often, we miss the story that gives you the full context of just normal people trying to figure stuff out. Usually it’s extreme persistence or a really unique founding team or the right time to market or whatever, and then some people that are fortunate enough to figure that out, realize, wow, this is something I love doing, this is something that has hit in the market. I would be crazy to give this up. I love those stories.

Chris: I also read recently How to Change Your Mind by Michael Pollan, which is a book about psychedelics, and that was incredibly interesting. If you have any interest in that at all, which I didn’t even realize I did, is a very, very interesting book, where he talks about the effect that it has on the brain, and how kids’ brains and very little kids, how they operate, it’s as if they’re on LSD, and he describes a bunch of psychedelic experiences that he had. This is the same guy who wrote Omnivore’s Dilemma, but I could not stop reading that book. I thought it was really, really interesting.

Jeroen: Yeah, I’m currently reading a book in a similar area, a bit theoretical, I must say. Behave.

Chris: Okay.

Jeroen: I don’t know if you’ve heard of it. It’s by Robert Sapolsky.

Chris: Okay.

Jeroen: It’s a bit heavy, so I’m struggling right now, even though I had some medical background. I’m reading it and I’m just constantly thinking.

Chris: It’s dense?

Jeroen: Especially because before it, I read Shoe Dog as well, and Shoe Dog was amazing. You could just read through it. It’s the most human entrepreneur story I’ve ever read, probably, just the way he wrote it and all the details. It was great. Then I went to do this hugely theoretical book, which is very interesting, but It’s a bit of a pain.

Chris: Yeah. I hear you.

Jeroen: Now, the final two questions. Is there anything you wish you would’ve known when you started out?

Chris: Anything I wish I had known when I was starting out. There’s a lot of things. I’m trying to pick the one. I think the most important thing that I have learned over these years is that you have to pick your co-founders wisely, and you have to invest in that relationship like it is a marriage. You need to confront hard problems, you have to celebrate wins, you have to be clear about how you are dividing ownership, and I have watched over and over and over again, so many other friends and founders lose the importance of those relationships as they build their companies, or they meet someone they’ve known for two weeks and then they start a company with them. And I think that you are signing up for a long journey. Even the companies that think that they’re going to sell quickly, just know, never guarantee that you’re going to sell quickly. Quick is five years.

Chris: So if you don’t feel like you really want to spend all your time with somebody, you want to go through some of the hardest moments of your life with them and the most joyful, if you don’t take that seriously, that could easily sink you later, and I think we got really lucky with that in the early days. We said our friendship is really important. We put it first. We actually invested in it, and we’ve learned how to have hard conversations. So it means that we’re aligned all the time, and working on the right stuff, and can do great work together, and that, I feel very, very fortunate about. I think we could have invested earlier in that. But starting again, I would say, for any founder, they should be asking themselves questions around that.

Jeroen: Yeah. Definitely agree, because it’s at the core of it all, right? You can have a great idea, but in the end, it’s two or three people starting out, working together. If that fails, you can have a great idea, talk about building a great team and all that, but it’s going to be hard.

Chris: Totally.

Jeroen: Finally, a bit of a similar question. What’s the best piece of business advice you ever got?

Chris: It’s funny. It just changed. I always think I’ve gotten the best advice, and then we go through another challenge, and I get the best advice again.

Jeroen: With the challenge. I hear you.

Chris: Yeah. In the early days, don’t do something if you’re not going to be obsessed with it. It’s just too easy to give up, and when there’s too many challenges and you need blind faith, you have to truly be obsessed with solving the problem. Then I think at some point, my dad gave me some advice. I was talking about our dreams of Wistia, and said, our dream is to get to $60,000 a year in revenue, because Brendan and I can each make $30,000, and we’ll be able to survive on that. My dad was like, look, if you’re right about this thing, it’s going to be a lot bigger than that. You guys need to prepare for success, and you need to think it through. What would you do if this was successful? What are the moves you could make, what are the things you would say no to?

Chris: It was funny, because there were actually some pretty big decisions we faced in the first few years where we said no to some giant customers, and no to some angel investors and stuff, because we tried to treat it like, well, if we are successful and still doing this in five years, are we going to want those customers who don’t feel like the right fit? Are we going to want those angel investors who don’t seem like they’re aligned with us? They felt like hard decisions to make at the time, and now looking back on it, they were some of the best decisions that we made, only because we tried to imagine, well, if we’re actually doing this, we’re actually successful, that the weight of those bad decisions will live with us. That turned out to be really good advice.

Jeroen: Awesome. Thank you again, Chris, for being on Founder Coffee. It was really great to have you.

Chris: Thanks for having me.


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Jeroen Corthout

Co-Founder at Salesflare
I'm Co-Founder of Salesflare, the simply powerful CRM for small businesses. I love growth, automating sales, and building beautiful products.

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