Matt Singer, "Music Moves Him," Ep 27

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While in prep school Matt Singer performed at a religious ceremony and became fascinated with the impact his music had on the congregants. This fascination led Matt Singer to major in music at Yale, where he graduated Summa Cum Laude, and to think of how to make a life in music. Matt hit the streets soon after graduating to start his music business. For ten years he built Dawn Treader Production with marquee names such as Paul McCartney, James Earl Jones and the New York Philharmonic. Relying on the emotional connection possible on TV, he sold the CDs he produced by the tens of thousands on QVC. In 2007 he joined co-founder Amanda Eilian, in starting a company that is now changing the way large enterprises communicate with their customers and employees via video. Videolicious makes it easy for employees to produce polished videos personalized to particular clients that make emotional connections. The platform is now used by 4,000,000 users in 100 countries, it’s even taught at 90 schools of journalism. Backed by Amazon and VC money, this startup is poised for continued growth.

This is the story of someone who followed what seems to be an impractical passion but managed to create something that is useful to large numbers of paying customers. Listen to this candid and introspective conversation with a young man who thinks deeply but acts practically. In particular, I liked what he had to say about how founders can prepare their psyche for the arduous journey of building their startup:

“It turns out that anything that you accomplish in life actually brings a crush of responsibility, so you really just have to enjoy the journey because there is no magic carpet ride of happiness that comes with any accomplishment.”

Click here to read full episode transcript.

Here are the topics covered and some quotes:

  • Matt Singer Bio
  • Matt Singer Actively Looks for a Way to Turn His Passion for Music into a Living, and Succeeds
  • The Story of The Talk Market Which Became Videolicious
  • How Matt Connected with his Great Co-founder, Amanda Eilian
  • What Videolicious Does Today
  • Sal Daher Reads a Review from Listener ChangDS and Ask Listeners to Leave a Review on iTunes
  • The Pivot that Turned The Talk Market into Videolicious
  • The Vision Stayed the Same, the Implementation Changed
  • Great Point about Finding Your Focus
  • “From the perspective of entrepreneurs, I think it's just good to note that you can have a vision but there are a lot of choices along the way in terms of who should you really sell to.”
  • Videolicious is Taught at 90 Schools of Journalism – It’s Becoming Ingrained
  • Instead of a Sales Binder Videolicious Allows You to Send Your Customer a Compelling Personalized Video
  • “Video is becoming the standard way that people create content.”
  • Videolicious’ Board Has Been Very Supportive – They’ve Been Amenable to Reasoned Arguments
  • “Yeah, you've heard that theme of focus, focus, focus, but exactly what that means is not always super clear.”
  • "Wow. What do I need not only just to get in the door, but also to keep them forever?"
  • How Matt Singer Got Amazon as an Early Investor in His Company
  • How Videolicious’ VC Backers Help with More than Money
  • The Interesting Route Videolicious Took to VC Funding
  • The Path Ahead for Videolicious – Making Video Creation Ever Easier & More Effective
  • Matt Singer’s Three Bits of Advice for New Founders
  • “Definitely finding a great co-founder is important… someone that you can really work with… work through thick and thin, because there's going to be ups and downs constantly and so it's great to have someone that can support you and you can support them.”
  • “…thinking through the entire lifecycle of your customer from the acquisition to renewal.”
  • Having a Long-term View Is Crucial in Selling to Enterprise Customers
  • Because Everybody Works from Home, Videolicious Looks for Self-starters
  • ” I do find that being able to tell the story and the vision is a good way to attract talent.”
  • Other Startups That Matt Singer Admires – Companies That Make Using their Product Super Easy
  • What Matt Singer Has in Common with C.S. Lewis
  • “…most technology is pretty disruptive for your average employee. It's different than what they're used to doing. That's what you have to contend with as a startup, you assume that's a big jump, even if your product in the isolation is easy.”
  • Matt Singer’s Parting Thoughts – A Truly Valuable Observation
  • “It turns out that anything that you accomplish in life actually brings a crush of responsibility, so you really just have to enjoy the journey because there is no magic carpet ride of happiness that comes with any accomplishment.”

Transcript of Matt Singer, "Music Moves Him," Ep. 27

GUEST: Musician, Thought Leader & Founder Matt Singer

SAL DAHER: Welcome to Angel Invest Boston, conversations with Boston's most interesting angel investors and founders. I am Sal Daher, and my goal for this podcast is to learn more about building successful new companies. The best way I can think of doing this is by talking to people who have done it, people such as startup founder, music entrepreneur and thought leader, Matt Singer. Matt, I'm delighted you're joining us on our 27th episode.

MATT SINGER: Delighted to be here.

SAL DAHER: It's great you're here.

MATT SINGER: Thank you.

SAL DAHER: By the way, here is not our usual studio, but the Four Points by Sheraton, Norwood. We are recording here to accommodate our guest, who will be addressing the Inside Sales Conference shortly.

Matt Singer Bio

Matt Singer grew up in idyllic Exeter, New Hampshire, where his dad was a beloved and respected physician. He studied at Phillips Exeter Academy and got to be concertmaster of the school's symphony orchestra. Matt then attended Yale, there he studied music composition and media technology, graduating summa cum laude. This sound like the biography of a brainy, hard-working kid who went on to Harvard Law and then to a highly lucrative M&A practice on Wall Street, well, it's not. Soon after receiving those academic accolades at Yale, Matt was hitting the streets to build his first business, Dawn Treader Productions. The hustle paid off, Matt produced and released a number one Billboard classical CD with Paul McCartney, Billy Joel, Ray Charles and prominent orchestras in New York and London. He also produced a national PBS TV special with George Clooney and James Earl Jones. The studious Yaley became an accomplished seller on QVC, where he sold over half a million CDs and DVDs. Matt also displayed a knack for dealmaking, setting up marketing partnerships with Dayspring Hallmark and LL Bean.

After 10 years of running his own business, Matt had the idea to go off and found a company with a co-founder, the company that has become Videolicious. That venture-backed startup makes it really easy for anyone to create sophisticated video production on mobile devices in minutes. The company has more than four million users in 100 countries. I'll ask Matt to tell the amazing story later on. On his own right, Matt is a thought leader in the use of mobile technology to reach customers and is even an inventor on a patent in this area. I think we can all learn a lot from Matt.

Once again, I'm really glad you're here, Matt.

MATT SINGER: Thanks for the kind intro.

Matt Singer Actively Looks for a Way to Turn His Passion for Music into a Living, and Succeeds

SAL DAHER: The kind of intro your mom likes, right? Matt, as a service to our young listeners, it's a tradition in our podcast that we like to have our hugely successful guests talk about how they found their calling in life, how did you decide not to pursue that putative career on Wall Street or become a physician like your dad, but instead to go into the music business?

MATT SINGER: Sure. Well, I grew up playing music, I grew up learning music and I think I was always really drawn to the ability to uplift people emotionally, so there was something about that emotional power of the medium of music. I do remember when I was in high school, I played for a particular religious ceremony, a Christian ceremony in a church, and people were crying, and I just remember thinking myself, this is really powerful, to be able to speak to people and reach people in ways that really change how they feel.

SAL DAHER: Awesome. It was a follow-your-passion kind of thing.

MATT SINGER: I think so. It was passion, but just I felt like at the time my best use of my abilities was to deal in the emotional arts. It's interesting because that still applies with Videolicious, the topic that I'm speaking about today is about emotional engagement, so I've been drawn to that side of the coin, the idea that there is opportunity to not just make people feel good, but also to help drive business and relationships and sales and things like that in the arts of emotion.

SAL DAHER: So, you have this passion for music and its capacity to move people in an emotional way and you found a way to make a living at it?

MATT SINGER: Yeah. I knew it wasn't going to be easy. In college, I really tried to learn as much of a vocational set of skills I could, which is sometimes hard in a liberal arts college, but the first second I got to school, I walked the halls looking for other musicians to create a professional band with, and just try to eat up every possible skill I could. I think I was also just drawn really immediately, not just to the music making, but the business side of it. If there was a way to do something creatively that's a little bit different than the traditional path ... I think that really helped turn it into a living.

The Story of The Talk Market Which Became Videolicious

SAL DAHER: Wow. Tremendous. How did The Talk Market, the predecessor to Videolicious, come about? Please tell us the story.

MATT SINGER: Sure. In the music industry work that I had, we found a really, really powerful way to sell things, and that was through QVC, the TV shopping channel. Some of you may not be super familiar with it, but it is an incredibly powerful medium-

SAL DAHER: Get us into the time machine and go back and tell people what QVC ... Is it still-

MATT SINGER: It's still going very, very strong. Certainly, the internet has disrupted it a bit, but look, television is really popular still, people still watch TV and-

SAL DAHER: It makes an emotional connection.

MATT SINGER: Yeah, video drives sales. I think they're still doing $7, $8 billion a year. It's a big business for sure. Yeah. So basically that was one of the primary drivers of sales for me in my previous company. Being able to put together groups of musicians, perform on television, get people really emotionally engaged and then have them pick up the phone and buy something.

So, I got together with my cofounder, Amanda Eilian, and we wanted to take that power of video to drive sales and unleash it to the masses, give more people the ability to do it because the core challenge of using video in general is that, up until recently, video production is expensive. QVC, they have a massive studio complex with all these cameras and equipment and expert people, and certainly there's always going to be a high-end craft of video creation, but we wanted to see if we could democratize it a bit because we saw, and my co-founder worked with other companies that sold through QVC as well as an investor, we saw that video truly works. It has an amazing power to get people to buy. There was moments when I did business there and we drove $20,000 a minute in sales, and this was just a small company just getting this medium and being able to sell all this continent and product.

SAL DAHER: So, you were trying in the first instance of Videolicious, The Talk Market, you were attempting to disrupt QVC's business, you were trying to create a QVC for the internet?

MATT SINGER: Not exactly. I don't think we were going after QVC. It was more just spreading the love around, spreading the power around-

SAL DAHER: Right, trying to create a QVC-like situation in the internet.

MATT SINGER: That's right.

How Matt Connected with his Great Co-founder, Amanda Eilian

SAL DAHER: Okay. Now, how did you connect with Amanda in the first place, with Amanda Eilian, your co-founder?

MATT SINGER: Yes. I met her through my wife, Fiona, they were friends at Georgetown, and then I did some consulting work for her private equity firm when they were looking to invest in or acquire companies that were selling through QVC. So we talked about and worked on, basically, some of the dynamics of what it's like to sell using video and things like that, and so basically we got together one night and thought about the power of this medium and how could we use technology to give it to more people.

SAL DAHER: Excellent. Give us a little bit of background on Amanda. She was at Georgetown, Harvard Business School, Baker Scholar, private equity, so she's more on the finance side?

MATT SINGER: Yeah. It's an amazing partnership. She's incredibly smart and talented, and ... Yeah, as opposed to my musical, touchy-feely background, she has a really great strong business background in M&A from Merrill Lynch and private equity, and she's just accomplished angel investor herself with a lot of great exits, so it's been powerful to have the Ying and the Yang of someone who has a real investor mindset, who ... I think good investors basically look the positive and the negative in the eye, it's about assessing risk so it's their job to look at things and say like, "Let's not get too excited," or too into ourselves, "let's figure out the numbers and what does the story really tell us." That's really important to the survival of the company is that mindset. I think I've learned a lot from Amanda over the years, I've probably become more around to her side of the coin, but the artiste and the goes-to-a-sales pitch, and I see the eyes of people and I get excited, I think we're going to do this, and she definitely can see through some of that in a good way, in a way that allows us not to sit on our laurels.

What Videolicious Does Today

SAL DAHER: Excellent. Please tell us what Videolicious does today. What problem does it solve for its users?

MATT SINGER: Sure. As you mentioned, Videolicious is a super-fast and easy way to make super high-quality videos. We focus on the enterprise so we work with a lot of very large companies, with tens of thousands or hundreds of thousands of employees, and they use Videolicious to create videos for the sales process, so prospecting videos, pre-meeting videos, post-meeting videos, follow-up videos, they also use it for recruiting videos to approach candidates or to highlight specific jobs, they use it for corporate communications, both internally and externally, for training on specific product features, so it's almost like a Microsoft Word or PowerPoint video. The idea is that there's a billion people in the world that use content creation for texts, for spreadsheets, for slides, and until recently, it wasn't possible for them to do video productions to create videos as well, and since video is so popular, it is the most popular format in the world, and Cisco keeps saying every year. 80%, 85%, 90% of the internet is video, so more and more people are looking to create video in their jobs. That's what we're about, enabling that to happen in a really high-quality way.

SAL DAHER: Tremendous. Coming up next, we'll ask Videolicious cofounder, Matt Singer, about the pivot that set his company on a new and highly promising course.

Sal Daher Reads a Review from Listener ChangDS and Ask Listeners to Leave a Review on iTunes

First, I wish to thank listener ChangDS for this review in iTunes, "It's obvious tons of prep work goes into producing each one of these podcasts. The questions are great and the dialogue is lively between Sal, the host, and his guests. Really enjoyed listening to the variety of people who have been guests on the podcast." Thanks, ChangDS. You've done your bit to help this podcast get found by more people.

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The Pivot that Turned The Talk Market into Videolicious

Matt, please tell us about the pivot that turned Talk Market into Videolicious. How could you tell it was time to pivot? How did you decide in the new direction?

MATT SINGER: Sure. We've had trajectory where the world of technology has changed, and when we started the company, we had this vision of empowering sales with video, and it's pretty consistent to what we do today, but form factor was very different. When we started the company, the iPhone didn't actually even exist or just barely existed-

SAL DAHER: Right. So the company was started back in 2008?

MATT SINGER: In 2007, technically. Yeah.

SAL DAHER: This is just when the iPhone came out.

MATT SINGER: Yeah, exactly, exactly. The iPad was about to come out. Basically, the first version of the product was something that we had to put in a suitcase, it was a computer with cables, connected to a camera and a microphone, and I would carry it around in airplanes and bring it out and set it up frantically in presentations, but we actually sold these systems to a lot of companies, Walmart, Best Buy, Costco, the Gap, Macy's, Cole's, basically almost every major retailer got this system where they would churn out sales videos-

SAL DAHER: But let's step back because this is one of the themes of my prior episode, Episode 22, Professor Ed Roberts, he says founders always forget the pivots. I guess it's such a painful experience, they don't want to remember the full details, but originally The Talk Market was a little bit like a marketplace where people who had interesting things that were visually appealing would sell. I say this because I was an early investor in The Talk Market and, subsequently Videolicious. So basically you created this technology to address this market, these small sellers, a little bit like Etsy on video, but then the going was really tough. You figured out that growing that to scale was just going to take you a long time, and so forth, and I guess you started going over to corporate clients, Walmart and so forth, and take this technology that you developed originally and you started selling to them. Please continue with that story.

MATT SINGER: Yeah, sure.

The Vision Stayed the Same, the Implementation Changed

SAL DAHER: Unpack the pivot.

MATT SINGER: No, you're 100% right. Look, the vision has been, again, surprisingly consistent-

SAL DAHER: It is the same vision-

MATT SINGER: Yeah, yeah, the question has really been what's the technology ... Again, it's over a pretty significant period so, understandably, that would evolve. But, yeah, what's the technology, what's the medium, who's the market.

Great Point about Finding Your Focus

“From the perspective of entrepreneurs, I think it's just good to note that you can have a vision but there are a lot of choices along the way in terms of who should you really sell to.”

From the perspective of entrepreneurs, I think it's just good to note that you can have a vision but there are a lot of choices along the way in terms of who should you really sell to. It's interesting, there's so many slices to that coin, so a lot of software and service company, SaaS companies, they initially start with small businesses and then they go to midmarket and they go up to enterprise, but then, again, there's also within each of those areas, there is specialization. You could be small business, but you could be, let's say, a real estate agent small business or things like store-owners. Yeah.

I think maybe if I were to talk to myself in the founding stage, I would walk myself through some of those questions because it's true that you may think you're focusing ... In other words, "Hey, we're empowering people to sell with video, with great ideology," but there's so much to focus ... Even in this speaking engagement today, this is about inside sales, so a lot of enterprises use our technology to drive their sales, but sales in the enterprise is not a monolithic activity there is pre-sales, and there's prospecting, there's account executives, there's account managers, there's account directors, and each of those functions have specific things that they do in the sales process, so definitely there's ... They always say, obviously, focus a lot as an entrepreneur, but what that exactly means, I think, is not always that ... It could be even more than what you're thinking, if that make sense.

Videolicious is Taught at 90 Schools of Journalism – It’s Becoming Ingrained

SAL DAHER: Yeah. No, no. This is an interesting direction you're going in here because focus for an enterprise that has very limited resources, much more limited than well-established operating businesses, is really the most important thing, market discovery, figuring out where is the most effective use case for you to address. I know that you guys went through ... For example, you got adopted at 90 schools of journalism as the standard for creating video in the news business, you've been adopted in the real estate business, I know that Century 21, or various parts of that, use your service, so you seem to have gone through all the different verticals and now you are working very hard on large enterprise companies. For example, I noticed that the SAP is using your technology for creating sales videos. I think it's an internal ... For training, I don't know what they're using-

MATT SINGER: No, actually, again, a lot of companies use it for external facing pitch videos. They want to create more of a personal connection to the sales process, and you think about today's toolkit there's basically phone calls and emails and meetings, and the meetings are great because you can relate to people and express body language and tone and things like that, but you can't scale meetings very well, so video is a very powerful way to do that.

SAL DAHER: There's also stuff you can do in a video in terms of visuals that you can't do in a meeting.

MATT SINGER: That's right.

Instead of a Sales Binder Videolicious Allows You to Send Your Customer a Compelling Personalized Video

SAL DAHER: I was reading through your material, you were saying that the idea of instead of sending a binder to someone, you send a video right tailored to that particular client's needs, perhaps with some exhibits and showing and so forth before you actually go and see the client.

“Video is becoming the standard way that people create content.”

MATT SINGER: Right. It's amazing, that is becoming the trend. Again, it's a little bit of an adjustment for sales people to learn the craft of video, that's where our company spends a lot of time in teaching people the soft skills around video, beyond our technology, but, yeah, it's amazing. It makes perfect sense, think about Facebook, more, more it's just video, or Twitter, it's just video, Snapchat is almost all video so, of course, as people switch to their professional lives, they're not going to want to see just static pictures anymore or phone calls. Video is becoming the standard way that people create content.

SAL DAHER: That is really, really tremendous. Now, what role did your board play in helping you accomplish your pivot?

Videolicious’ Board Has Been Very Supportive – They’ve Been Amenable to Reasoned Arguments

MATT SINGER: Our board has been amazing, they're wise and they're really supportive. Again, I think usually when we present evolution in learning, it's based on a lot of discussion and factual observation, and so as long as we make a case based on what we're seeing and the trends that we're observing, they've been really, really supportive. It's the obvious next step in hindsight always, as you evolve the product and focus more but, again, it's not obvious when you're in the middle of it because, again, you don't realize the shades of focus, not to keep coming back to that theme, but that's definitely been a powerful lesson for me as a CEO that ... Yeah, you've heard that theme of focus, focus, focus, but exactly what that means is not always super clear. Again, it could even just mean building features for one specific type of employee that actually helps them measure the ROI that they get so they can renew that customer after three years, or something like that.

“Yeah, you've heard that theme of focus, focus, focus, but exactly what that means is not always super clear.”

 You don't think about that where you first think about just selling the product and getting the first deal, but to build a lasting SaaS company you have to keep them for decades. Again, if they can easily measure the results of whatever your product does for their specific job function, then they may leave you. That's another level focus, it's just taking you to the next level where you're like, "Wow. What do I need not only just to get in the door, but also to keep them forever?"

"Wow. What do I need not only just to get in the door, but also to keep them forever?"

SAL DAHER: Yeah. When I'm thinking about this, and I'm thinking back on your 10 years in the music production business, I can see how your street hustle of being out there, talking to people that you might do business with in the future, and so forth, has helped you tremendously, and that is very important for really understanding people's needs, is the fact that you're with them all the time. You travel a tremendous amount, you're not a CEO that's in the office all the time, you're quite the opposite, you're traveling all the time, I know that for a fact ... Just a disclosure, Matt is married to the daughter of my long-term business partner, Robert P. Smith, Fiona Smith, Bob Smith, who's an accomplished photographer, she has her own business in that, so I know Matt ... I was at his wedding, I've known and admired him for a long time so I'm really tremendously glad to get this chance to ask questions and to share his just really inspiring story with so many of people.

How Matt Singer Got Amazon as an Early Investor in His Company

Now, early on, your company, when it was The Talk Market, got funding from a mega strategic player, how did that come about and how has it worked out?

MATT SINGER: Sure. You're referring to Amazon, they've been a longtime investor in Videolicious. Yeah, we love them. They're just great investors. It’s interesting, it really came about from being an early user of Amazon Web services, Amazon Web Services was just taking off when we started and we actually engaged with some of their team on the product side, we were building the technology and using it in a certain interesting way and ... We even caught some bugs. We were on the phone with some of their development team far away, and that team basically forward us to the corp dev department, and they were interested in what we were doing.

I think because our approach to video, not over-speculate, but we had a very sales-focused bent in terms of the video creation. It wasn't just video to make a pretty video, it was coming from the world of QVC, thinking about video driving commerce and, obviously Amazon is amazing in the commerce area, so I think that was some of the attraction.

SAL DAHER: Yeah, interesting. Are you using AWS now?

MATT SINGER: Sure, yeah.

SAL DAHER: Very good. Very interesting.

MATT SINGER: Big fan.

SAL DAHER: Yeah, I can imagine. Videolicious has also gotten funding from VCs, what have they contributed other than money? Please, talk about that.

How Videolicious’ VC Backers Help with More than Money

MATT SINGER: Yeah. We love our investors. They've connected us with customers, connected us with other investors, just given us advice on various phases of the startup world. Yeah, it's important to try to get a value more than money from your investors. Yeah, the good ones will definitely provide that. We've gotten some amazing customer relationships from our investors that have been really, really meaningful and helpful.

The Interesting Route Videolicious Took to VC Funding

SAL DAHER: How did you connect with your first VC investor?

MATT SINGER: It's been a really broad past, we've connected with people through AngelList, we've met them at events, we got intros-

SAL DAHER: You actually connected with somebody through AngelList who wrote you a check?

MATT SINGER: Yeah, I think we got in-

SAL DAHER: A VC or an Angel?

MATT SINGER: Yeah, both. We got in before it probably was so big that it's impossible-

SAL DAHER: Matt, by the way, is a very early adopter. He was on Twitter ... I can imagine you must have a pretty cool Twitter name.

MATT SINGER: I guess. But, yeah, look, we're grateful for AngelList, that was a great resource for us at the time. We definitely searched far and wide and we weren't afraid to be creative, and that definitely paid off.

The Path Ahead for Videolicious – Making Video Creation Ever Easier & More Effective

SAL DAHER: Excellent, excellent. What's your vision for Videolicious now that you have millions of users and have worked out how to grow?

MATT SINGER: The creative path of just making video creation easier and easier just keeps evolving, and that's what's really fun and exciting. As we see it used more in the enterprise, we learn more about employee needs in terms of their specific job functions and how to make their job easier, make it more fun and just what works and what doesn't. I think one of our big differentiators besides the fast and easy video creation technology is quality, that we're keenly aware that video is not a magic ploy. It's not you just stick a video in an email and, oh my goodness, now you're going to close the deal. It's the same thing as text. I can send you an email that said like, I don't like you very much, and people would actually run away, and the same thing with video, you can send a video where you sound bored and you don't want to be in the video and you're grumpy or something like that, and that's actually going to make it worse for you than if you use video at all.

We're just constantly laser focused on optimizing that side of the coin, which is a complex challenge, there's a technology component to it, but there's also an enablement component ... Sometimes just a smile is what matters. People communicate so much with just body language-

SAL DAHER: Maybe you could have something to the text, it's easy software to write, if someone is smiling, "You are not smiling."

MATT SINGER: Trust me, we have a lot of cool stuff like that, and it works. I can't reveal any secrets here but-

SAL DAHER: We suggest looking at the camera and not the roof.

MATT SINGER: It's amazing how much that drives results, that's the thing. Yeah. There's fun technological challenges to solve that, but that's our passion is that it's not just about helping you create a video for video's sake, it's about helping you make a video that really drives a business result.

Matt Singer’s Three Bits of Advice for New Founders

SAL DAHER: Excellent, excellent. Matt, what three bits of advice would you give a new founder?

“Definitely finding a great co-founder is important… someone that you can really work with… work through thick and thin, because there's going to be ups and downs constantly and so it's great to have someone that can support you and you can support them.”

MATT SINGER: I think, certainly when you start out ... Definitely finding a great co-founder is important, I think a lot of people say that, someone that you can really work with, who you can really work through thick and thin, because there's going to be ups and downs constantly and so it's great to have someone that can support you and you can support them. I think that's just really, really important, psychologically in addition to strategically.

“…thinking through the entire lifecycle of your customer from the acquisition to renewal.”

Again, we talked about the focusing thing, but exactly what that means is just thinking through the entire lifecycle of your customer from the acquisition to renewal. That's, again, something that you feel like it's a high class problem, renewal, when you first start, but that's super, super critical.

SAL DAHER: In the long run that's what keeps you-

MATT SINGER: Well, right-

SAL DAHER: Controls your cost of customer acquisition.

MATT SINGER: Exactly. Think about how much easier it is to keep a customer than-

SAL DAHER: Than to get a new one.

MATT SINGER: Yeah, exactly. If you're aware of that challenge and what's going to drive their decision up front, you can build the product better to address that. That's definitely something that I didn't think about from the very, very beginning.

Having a Long-term View Is Crucial in Selling to Enterprise Customers

People have said this before, but having a long-term view, just being ready for the long-haul, especially if you're selling to large enterprises, those deals take a long time, so the scaling is going to take a little while so you have to be ready for the long-haul.

SAL DAHER: Very good. You've built an effective team at Videolicious, what advice do you have for the startups on attracting and retaining good people?

Because Everybody Works from Home, Videolicious Looks for Self-starters

MATT SINGER: Sure. We have a little bit of a unique bent on that because we have a fully distributed workforce, everybody works from home. Almost 30 employees, and they're in various parts of the world. For our needs, we look for people that are real self-starters because since we're not shoulder-to-shoulder in an office, they have to really be passionate about their work and love what they do and want to do it because we're not micromanaging, but we found those people, and they're great and they're amazing to work with.

” I do find that being able to tell the story and the vision is a good way to attract talent.”

I do find that being able to tell the story and the vision is a good way to attract talent. In general, people do want to feel like they're part of something and part of a clear mission, and if you as a founder are passionate about that and excited about that, that can definitely catch fire and get people excited. I think that's something that is within a founder's control to be excited about their own business and be able to tell the story well. It's important for a lot of things like selling the product to and raising money, but, yeah, it comes through with recruiting as well.

Other Startups That Matt Singer Admires – Companies That Make Using their Product Super Easy

SAL DAHER: Matt, is there another startup, other than Videolicious that you were really admire?

MATT SINGER: I love to look at startups that where the usability and the overall usage is almost automatic, things like Slack or I think companies like InVision have had great products like that where users can figure it out and just go, I think that's incredibly difficult. To pull that off, you have to have a product where you're innovating on something that people already have done and they just are improving upon it, they're familiar with the work functions. We are more in the realm where usually the things that people have not done. Most of the people who use Videolicious have never made a video before, so that presents certain challenges.

But I like to learn from startups that have taken processes that people are familiar with and improved upon them and created products that have users using them without even much help, or at least from a distance it doesn't seem like that. That's impressive to me, and I try to see what we can learn and emulate that wherever possible.

SAL DAHER: That brings to mind is the name of your company, Dawn Treader Production, is there any connection with C.S. Lewis in that?

MATT SINGER: Not any connection at all.

SAL DAHER: Not any at all? Okay.

MATT SINGER: There's a story behind that, which I can't really...

What Matt Singer Has in Common with C.S. Lewis

SAL DAHER: But it's funny because C.S. Lewis used to talk about writing so that someone can understand it perfectly, basically his prose was very user-friendly, and he spent an unbelievable amount of time to get his prose to be user-friendly. It's easy to write prose that's not user-friendly. I guess, in that example it's exactly what you're doing, you're just spending an unbelievable amount of energy to make things easier for the user.

MATT SINGER: Yeah, and it’s funny because ease-of-use is partially about the UI and the UX of your product and things like that, but it's also about what their job is today and how you're possibly trying to change it. That's where it gets complicated because, again, if someone's already, let's say, shoveling snow and you create something that helps lift that shovel, that's a pretty easy user experience jump, but if someone's shoveling snow and you're saying, here's a paintbrush, that's ... Even if you have a super easy to use paintbrush like that, that may be kind of hard. Yeah, I think that's where the art-

SAL DAHER: We have super-efficient paintbrushes for removing snow.

“…most technology is pretty disruptive for your average employee. It's different than what they're used to doing. That's what you have to contend with as a startup, you assume that's a big jump, even if your product in the isolation is easy.”

MATT SINGER: Exactly, exactly, but that's the thing, most technology is pretty disruptive for your average employee. It's different than what they're used to doing. That's what you have to contend with as a startup, you assume that's a big jump, even if your product in the isolation is easy.

Matt Singer’s Parting Thoughts – A Truly Valuable Observation

SAL DAHER: Take a moment and think if there's anything else that you want to say in concluding.

MATT SINGER: Sure. Just in general, really, really, thanks again for having me on the program. It's great to be here and to see you. Yeah, I think it's just the entrepreneurial life is really fun and exciting, at least I found it to be. As long as you go into it knowing that you're going to face come challenges, and that's basically the fun part. My daughters are really into pop music, and we listen to that song, The Climb, and I relate to it in the sense that you have to really enjoy the journey-

SAL DAHER: How does the song? How does it go?

MATT SINGER: It's going to get me emotional, so-

SAL DAHER: No, go ahead and sing. Go ahead and sing.

MATT SINGER: No, no, it's okay. Basically, it's true that you have to be ready for the journey and you have to enjoy the journey. I found that to be true in my last startup, too. I remember when I first solidified the production with Paul McCartney, as an aspiring music entrepreneur I thought, "Hey, if I get to do something like that, I'll get to ride this magic carpet of happiness for the rest of my life," then I realized that once that deal got struck, I got overwhelmed with the responsibility that came next. Like, "Hey, he's a major artist that I have to be careful and take a lot of care to not mess it up and represent him well in this music creation," and things like that.

“It turns out that anything that you accomplish in life actually brings a crush of responsibility, so you really just have to enjoy the journey because there is no magic carpet ride of happiness that comes with any accomplishment.”

So, I thought about this phrase, success brings more work to do, just that don't get caught up with this idea that, "Hey, if I only get X, then I'll feel amazing and my life be complete." It turns out that anything that you accomplish in life actually brings a crush of responsibility, so you really just have to enjoy the journey because there is no magic carpet ride of happiness that comes with any accomplishment. Any deal you sign, any money you raise, all of that brings this crushing responsibility, so as long as you know that going into, then you're going to be a little bit more even keel. You'll be like, "Of course we're going to be great if we raise that round, but then I'm going to have like six new bosses and tons of pressure to hit the numbers," so it's just one more step along the way. I think maybe that's the thing I'd like to share is just success brings more work. Just keep it in mind and try to enjoy each stage versus putting your emotions into any particular accomplishment.

SAL DAHER: That is extremely wise, very wise. Matt Singer, I'm so grateful to you for vaulting over all the logistical obstacles to be in our podcast. I hope our listeners have found this interview to be as rewarding as I have. Listeners, if you enjoyed this podcast, please review it on iTunes, write to me at sal@angelinvestboston.com with critiques or suggestions. Do sign up for future in-person events. This is Angel Invest Boston, conversations with Boston's most interesting angels and founders. I'm Sal Daher.

I'm glad you were able to join us. Our engineer is Raul Rosa. Our theme was composed by John McKusick. Our graphic design is by Katharine Woodman-Maynard. Our host is coached by Grace Daher.