Kevin Garber: [00:01] This week on the "It's a Monkey Podcast."

Ryan Frankel: [00:03] I don't think there's a catch or solution that you can apply to anyone who wants to become an entrepreneur, and whether or not you should get an MBA, or whether or not you should have work experience beforehand, or even get a college degree. I think it really depends on who you are and what you want to do.

[00:19] [background music]

Kevin: [00:21] Hello. Good morning, good evening, wherever you are in the world. My name is Kevin Garber. I'm the CEO and co-founder of ManageFlitter. It is Wednesday the 8th of February if you're watching us and listening to us live on Periscope.

[00:40] It is Friday the 10th of February if you're downloading this on your podcast app or even watching us on YouTube. We now upload our podcasts to YouTube. You can head on over to YouTube and subscribe to our channel and you'll get pinged up when we release a new episode.

[00:57] As usual with me is my co-host, Kate Frappell.

[01:00] Kate, thanks for joining us.

Kate Frappell: [01:02] It's good to be back.

Kevin: [01:04] If you haven't listened to our previous episode, episode 79, you really have to head over to it, itsamonkey.com, and listen to our previous episode. We interviewed David Heinemeier Hansson who is the CTO and co-founder of Basecamp, which is a project management software that has over 100,000 paid users, incredibly successful business.

[01:24] We chatted today a bit about all things relating to startups, Donald Trump, the tech industry and Donald Trump. That podcast has already smashed through all of our listenership records. David is a very smart and very opinionated guy, but not in an opinions-for-opinions sake. He is really a well-thought, and answers to the questions that we put forward to him. If you haven't listened to that show, please head on back to that show, and have a listen. I'm pretty sure, you will enjoy it.

[01:51] As always this week, we've got a fantastic show coming up. We will chat to Ryan Frankel, who has written a book about his startup experience. He started a company called VerbalizeIt. He is the former co-founder and CEO of VerbalizeIt.

[02:05] He has written a book called "The Making of an Entrepreneur, Lessons from a Winding Journey Towards Entrepreneurship." I chatted to him a little while ago about his entrepreneurship journey. As usual, we're going to kick-off the show with some goings on in the tech industry. Our industry moves almost at the speed of light, and there's always things happening.

[02:23] Kate, this week, I believe Google has rolled out some features to what they called G Suite, which is a combination of Gmail, the documents, the file system, the calendaring system that companies use throughout the organization.

Kate: [02:38] Yes. Google have released Cloud Search, I think, in the last day or so. Basically, it allows you to search within your company's Google files or your emails, docs, spreadsheets, events, and they've even added a corporate directory so you can connect with other people that you work with, get their contact details. I believe there's also easy way to either, start a hangout with them, send them an email, and even call them.

Kevin: [03:07] I think this is, and also one of the use cases, is to help surface some of the information that remains locked up in especially bigger corporates. Even in companies' outsize that someone does a document, people aren't aware of it. When people want to find it, they can't find it.

[03:24] There's all these amazing information and inside an organization, but is locked up. Now, Google are trying to allow for searching across different elements across the organization to try surface bits and pieces that may be relevant to someone else, right?

Kate: [03:39] Yeah, they're doing that. There's also a type of machine learning which guide you through your days or recommends what are things you're going to need. It will give you your calendar, and any relevant docs related to that. It learns what you're going to need from its files, I guess.

Kevin: [03:58] Quite interesting would be as a default in an organization to have document sharing set as on as a default, right? If you want to make it private, then you have to toggle it off, but as a default, all the documents are public.

[04:13] If you're working on a document, say you're working on documentation around setting up a new server, that Google can be predictive in a way and say, "Hey, there's the ten, there's ten documents in organization that seem to be matching a little bit what you're talking about. Click here to view them."

Kate: [04:31] Yes, I believe that's what they're doing. They're maintaining their current permissions. If you're invited and you currently have permission to folders and files, then you'll be only able to see those.

Kevin: [04:44] Currently, in the current Gmail Suite, like the one we're using internally, it doesn't allow searching across different users and organization in such an easy way?

Kate: [04:55] Not as easy. No. Not in a business and enterprise plans which this one is targeted to.

Kevin: [05:01] Right. I'm sure it's probably really useful, user permissions and across different departments and organizations, and they thought about it.

Kate: [05:09] We don't always want people saying everything like "You might only want to share document with two other people."

Kevin: [05:14] The interesting thing with Google and the Google Suite...I can't even keep up. I seem to have renamed their suite of products a few times. I can't really keep up with how they have gone from Google Docs to, and then Drive, and is Docs the same as Drive, but Docs includes spreadsheets and the word processor. They seem to have, somehow, approached...They sort of seemed to have missed a lot of the nuances of the way organizations use these products, right?

[05:43] I mean, we've even hit up ourselves. We are small organization. We've even hit up ourselves a few times against limitations a year ago when we're making some changes, etc. This is where, I think, the Microsoft...They've been at this game a lot longer. They might've worked out how organizations like to do things.

Kate: [06:05] At the moment, we hook in another program called AODocs, which allows you to organize your files. Also, I think the big benefit is you can't delete files if someone else arranges them. For example, if you create file, I can view it and edit it and stuff, but I can't delete it by accident.

Kevin: [06:25] Right. I've never quite understood why we use AODocs. I know you, guys, have a reason for... [laughs]

Kate: [06:30] Yeah. Well, apparently, the Cloud Search will eliminate the need for AODocs.

Kevin: [06:33] Support AODocs is now going to be redundant. That's the problem if you build businesses on other businesses, which we've done at ManageFlitter. Our business essentially sits on top of Twitter and soon to be Instagram as well. It's fantastic because you can leverage the success of another platform. It's got existing users, but you are exposed to what's known as platform risk.

[06:56] Jo, who set up the AODocs...She said it's about ownership. She's watching us on Periscope. I think she's our most-committed Periscope fan.

[07:05] [laughter]

Kate: [07:07] Number one fan.

Kevin: [07:08] Actually, why don't you go get Jo, and we'll get her to explain exactly...

Kate: [07:13] what AODocs does.

Kevin: [07:14] what AODocs does. Maybe that might fill the gap of us understanding what this new Google product is. We're just going to hop on out of the studio and call Jo who rolled out the AODocs across, which is a product that plugs into the Google Docs product. It allows for some more control. This is Josephine Pinto, who's the business operations manager at ManageFlitter.

[07:44] Jo, you were the one that was actually were involved in transferring some of our Google accounts, etc., a year ago. Tell us about this whole AODocs. Have you read about the new Google product that's being released across the enterprise, the G Suite?

Josephine Pinto: [08:00] G Suite, yeah. That's live. The one that I'm really hanging out for is Team Drive.

Kevin: [08:06] What's Team Drive?

Josephine: [08:07] Team Drive is more about the ownership of the documents that you've got on Google Drive.

Kevin: [08:12] Is this part of G Suite?

Josephine: [08:14] It will be part of G Suite. I'm not exactly sure. I'm thinking it's actually going to be released at the end of the year, maybe next year. The way that this is related is AODocs allows us to make sure that the business files are owned by the business.

Kevin: [08:32] Not an individual?

Josephine: [08:33] Not an individual.

Kevin: [08:34] It's been a problem in the...This is what I was referring to previously about Google not working out things properly is that, previously, if someone left the organization and, say, they worked on an important proposal and you wanted to deactivate their Google accounts, away goes all the documents. Was that correct?

Josephine: [08:55] That's exactly right.

Kevin: [08:56] AODocs was a way where you could decouple the ownership of the document from the individual user.

Josephine: [09:03] That's right. It gives you more power and control over who you're going to share that document with.

Kevin: [09:09] Now, has G Suites plugged that hole?

Josephine: [09:13] Not yet.

Kevin: [09:13] Still not.

Josephine: [09:15] It's still on an individual basis.

Kevin: [09:17] Still, if you have an individual tied to a document and you deactivate that account, that document is gone.

Josephine: [09:26] Yes, exactly, and that is why we use AODocs right now.

Kevin: [09:30] OK, so mystery solved. [laughs] Jo, thank you very much for joining us, and by the way, how was your...? We had you on a few podcast ago talking about your Android phone. How's the Android phone going? What's it called again? The Pixel.

Josephine: [09:45] The Pixel XL.

Kevin: [09:46] The Pixel...How's the Android phone going?

Josephine: [09:49] It's actually going really well. I've gotten used to it. All the disadvantages, I obviously didn't need them. They did not make much of an impact because I'm enjoying the phone right now. I guess the only disadvantage is the accessories.

Kevin: [10:07] Accessories being apps or actually hardware accessories of cases and things like that?

Josephine: [10:13] Yeah, hardware cases, extra little bits that you can use.

Kevin: [10:16] Apple have always had the most options for that.

Josephine: [10:19] Yeah, that's right.

Kevin: [10:20] Always had the most interesting options for that, and also the Apple Watch. I believe there's some new Android Wear watches coming out as well, so we'll have some choice. You recommend that phone? You're happy with it?

Josephine: [10:34] Yeah. Very happy with it and I do recommend it.

Kevin: [10:36] Better than the Samsung, the blowing up Samsung?

Josephine: [10:39] Don't know about that. I'm actually hanging out for the... [laughs]

Kevin: [10:43] The Note 8.0Josephine: [10:44] the Note 8.0Kevin: [10:46] You're die-hard, Jo.

Josephine: [10:45] I am.

Kevin: [10:46] They love people like you real brand evangelists. Have you found any advantages in having native Android in the latest version? Do you get a lot more frequent updates, or is there any time where you feel that you've benefit from having such a clean version of Android?

Josephine: [11:05] To be honest, I haven't noticed a difference.

Kevin: [11:08] Right.

Josephine: [11:08] It's all the same to me.

[11:10] [laughter]

Kevin: [11:12] Interesting. Josephine can tell you the business operations manager manage for that, which basically means she does everything. Thank you [laughs] for joining us and giving us that information about AODocs, so interesting, too. If you've had that issue in your organization before someone leaves and you don't want to lose the documents give AODocs a go. Thanks, Jo.

Josephine: [11:31] No worries. Thank you very much.

Kevin: [11:34] We've got an office full of smart people here we're lucky we can just drag them into the studio. That was Jo. That's juice sweet which we'll post a link to. We post a link to all these stories on itsamonkey.com.

[11:51] Other big new stories, Kate, Twitter have been pushing hard on fixing up some of the problems with trawls, and spammers, etc. They've rolled out a whole heap of changes this week.

Kate: [12:05] Yeah. They are putting their money where their mouth is, and rolling that, changes to curb abuse and bad behavior on Twitter. They're keeping the main and unsavory content out of sight. They've put a few new changes in, one of them being, a safe search preference. You can toggle that on and off.

[12:24] Another one being, they're automatically hiding inappropriate tweets beneath a show less relevant replies option. You'll have your regular stream of replies, and then there'll be an option at the bottom that says show less relevant replies. Then you can say the potential inappropriate ones.

Kevin: [12:43] The director of engineering, he's got a great Twitter handle @mrdonut. He twitted at about a week ago, "Making Twitter a safer place is our primary focus, and we are now moving with more urgency than ever. We heard you, we didn't move fast enough last year, now, we're thinking about progress in days and hours, not weeks and months."

[13:01] Twitter have come under a lot of criticism. In fact, there were even rumors when they were trying to get bought a while ago. That's some of the potential acquiring customers such as Salesforce and Disney not being back, because of the trawling and spamming issues.

[13:15] Twitter is in a difficult situation in that it is an open social media network, as opposed to Facebook which is linked into more closed social media platforms. As an open social media platform, I guess a little bit like Instagram, Instragram has got a problem as well with spam comments...

Kate: [13:34] Yeah and automation.

Kevin: [13:36] and automation. Open social media networks definitely it's trickier to deal with it. That being said, they can always do a lot more. It's good to see that Twitter are at least tackling this.

[13:49] There's been a lot of issues with people leaving Twitter. Even just saying, especially celebrities, and sports people, etc., that just get slam patrols, and they just say I just don't want to deal with this anymore.

Kate: [14:05] One other thing they're doing as well is they are going to be doing a better job of keeping banned users from re-joining the service in another name.

Kevin: [14:14] Now, what I found interesting about that is they didn't say how they're going to do it, right?

Kate: [14:18] No. They don't want anyone to game it.

Kevin: [14:20] Yeah, they don't want anyone to game it. I was thinking, "How are they going to do that?" I'm not exactly sure, because people can use multiple email addresses, they can even use multiple phone numbers. How are they going to do that? I don't know.

Kate: [14:34] Not too sure.

Kevin: [14:35] Not too sure.

Kate: [14:36] In the article he says, "Human review is a machine learning technology."

Kevin: [14:40] Unless what they do is there's some cookie bits and pieces with an IP address, maybe if they see that some things come from the same computer with the cookie, they'll push it through to a human and they'll check that. I don't know, unless they've got some really smart technology.

[14:58] What worries me a little bit is one of the issues that we face in ManageFlitter is we have users that get caught up as false positives in some of their efforts. I'm a little bit concerned that some legitimate users are going to get hammered a bit with some of these new initiatives, especially initially.

[15:14] They'll eventually work it out. I'm curious to see how they're going to get this right, because that is not a simple issue to solve. It sounds something like in a human real world, it's quite easy to ban someone from coming to a restaurant, you put a photo out there and you say, don't let this guy in. It's simple.

[15:35] On social media platforms something like Twitter to not let that same human just create new accounts? Good luck with that one.

Kate: [15:43] Yeah. In terms of false positives, how hard is it to be banned on Twitter? You must have to do something quite bad in the first place.

Kevin: [15:51] There's very few people that they've actually banned permanently. There's that one right wing commentator he's got a very long surname, so I won't even pretend to pronounce it. He was going to speak at Berkeley a week ago, and there were rights of his appearance there. It's very divisive figure.

Kate: [16:10] Twitter banned him.

Kevin: [16:12] Twitter banned him a while ago, before this happened. He's the one that I'm aware of. I'm sure there are other instances. Twitter does have a terms of service, and if you're in breach of their terms of service, they can actually deactivate your account.

[16:26] Usually what they do though, if you fight both Facebook, and Twitter, and I assume Instagram as well, if you breach or do something, they'll put you in jail for a while. All right?

[16:38] I've had even friends on Facebook that people like midwives, and things like that, that have posted images that Facebook doesn't like and they...

Kate: [16:47] Yeah, turn it off.

Kevin: [16:49] turn off their account for a month and tell them that you've been a bad person and don't do this again. Because of that, you can't use your Facebook account [laughs] for a while.

Kate: [16:56] So, it's embarrassing.

Kevin: [16:59] I do hope they sort that out because it's...I haven't probably three or four times of my life. I'm quite a big Twitter user, but I try to stay away from tweeting controversial things. Probably three or four times, I've had smacky tweets my way. It is quite unpleasant and it's a little bit confronting.

[17:21] I really do feel for the people that get hammered with hundreds and hundreds of abusive tweets, and offensive tweets. It's not really what the social platforms are about.

[17:32] Again, it's very hard to balance the freedom of speech versus this trawling issue. It's a very difficult issue. It started in the days even with YouTube, when YouTube comments used to be a nightmare. They were famous for being a nightmare. Then they locked it in with your real Google identity and that helped a bit.

Kate: [17:53] Yeah. For really sure you have to have a Gmail address now. Most people do. You have to hook in a Gmail address to get into YouTube.

Kevin: [18:01] And, one of the strengths and weaknesses of Twitter is you don't have to reveal your identity which is bad because you can hide behind it. It's good because say a kid in a conservative community can be anonymous and discuss and reach out to accounts that may be supportive of him, and it covers more people, even people in countries where there's no freedom of speech, right?

Kate: [18:27] True.

Kevin: [18:27] People can't tell who they are and that's a good thing. So, these are not straight forward issues at all. I'm glad I'm not the person that's given the task to make sure people who have been banned do not set up another Twitter account because I'm not quite sure, but an interesting challenge nonetheless.

[18:46] But, most of us standard Twitter users will be OK.

Kate: [18:52] Let's hope.

Kevin: [18:53] Let's hope. You're listening to Episode 80 of the "It's a Monkey Podcast." We've put together an hour of informative chat around technology, startups, entrepreneurship, self-improvement, anything related to the entrepreneurship, tech, economy journey we chat about.

[19:11] We're going to take a short break. After the break we're going to be talking to Ryan Frankel who has written a book about his startup experience. We'll be back after this short break.

[19:39] [commercial break]

Kevin: [20:23] You're back with "It's a Monkey Podcast." We talk about everything tech, tech economy startups, entrepreneurship, Blockchain, Cryptocurrency, all those exciting bits and pieces.

[20:34] Here at work I sit with three computer screens open and one of those screens has got my TweetDeck with Tweet streams running like crazy. That allows me to pick up interesting bits and pieces and interesting tweets. I divide my Twitter account into Twitter lists of various categories of tweets I don't want to miss on entrepreneurs, etc.

[20:56] And, a couple of weeks ago one of the Boulder, Colorado entrepreneurs, I think it was Brad Feld, twitted out about a new book, an autobiography of an entrepreneur, and I'm a bit of a sucker being an entrepreneur. I just love hearing about people's paths and I was interested to discover a new book, "The Making of an Entrepreneur," by Ryan Frankel.

[21:17] I'm happy to say I've tracked him down. Ryan is obviously the author of this book, "The Making of an Entrepreneur, Lessons from the Winding Journey Towards Entrepreneurship," and he's also the former CEO and co-founder of VerbalizeIt.

[21:27] Ryan, thank you, so much for joining us on the show.

Ryan: [21:30] My pleasure. Thanks for having me.

Kevin: [21:32] So, by the age of 28 you had worked for Goldman Sachs, you had received over a million dollar investment in your business, you had refused an investment from a Shark Tank episode, I believe. You had bounced around between a few different cities. And, the real interesting part of your journey hadn't even begun yet.

Ryan: [21:51] That's right. The real journey began when I was a graduate student at the Wharton school at the University of Pennsylvania. All of the years of experience I had leading up to that point in time gave me a lot of the tools to become an entrepreneur.

[22:07] When I was in grad school, the idea started hitting me straight in the face for this business. The next four years was really kind of a bumpy ride filled with a lot of highs, a lot of lows, which eventually resulted in an exit to sale to another technology company.

Kevin: [22:26] We'll talk a little bit about that exit a little bit later, but one of the parts in your book, I mean, your book is really interesting in the sense of as an entrepreneur I think we don't realize that, I wouldn't say we sanitize things to most people, but we leave out a lot of the gory little details and the setbacks and the millions of decisions and judgment calls we have to make. I always enjoy just seeing all the bumps in the road and the gory details.

[23:00] Something that made me smile was you, obviously, you had received your MBA from Wharton, which is one of the best schools in the world for that. You went to the Techstars talk on valuations and the person giving the presentation said, "If you've got an MBA member on your team, you can discount the valuation."

Ryan: [23:18] Yes, that was funny. We had just flown in from Philadelphia out to Boulder, Colorado and we had just rolled into the office and I got there in the nick of time. I barely was able to attend my graduation. Myself and my co-founder were both wearing our Wharton fleeces. We were freezing in Boulder, Colorado, and we're sitting there, she saw our Wharton fleeces and decided to make a joke at our expense.

[23:45] Needless to say, it had the whole room laughing, but it also had us both a little concerned as to what we really got ourselves into.

Kevin: [23:52] We won't go into a major tangent, but what are your thoughts on the MBA and if you want to be an entrepreneur? It's definitely, I think 30 or 40 years ago was the quintessential qualification, but now it's really a little bit more complex, isn't it?

Ryan: [24:13] It is. I don't think there's a catch all solution rule that you can apply to anyone who wants to become an entrepreneur or whether or not you should get an MBA or whether or not you should have work experience beforehand, or even get a college degree.

[24:26] I think it really depends on who you are and what you want to do. For me, I needed to rebrand myself. I'd done finance for four or five years. I didn't have an idea for an entrepreneurial adventure and I wanted to surround myself with a broader group of individuals. And so, for me, Wharton was the fantastic launching point for my own career. But, certainly there are people out there that don't even graduate from college who become hugely successful entrepreneurs. It really depends on what you're looking to get out of it.

Kevin: [24:59] I think another interesting point that I read in your book when you were in an accelerated program, Techstars, which is one of the most well-known accelerated programs, it really dawned on you then that business and startups is all about execution, not ideas, right?

Ryan: [25:15] Exactly. I've always said it's sort of ideas are a dime a dozen, but it really comes down to how well we all execute on them. How well you execute them on a business idea is really a function of what skills and what experiences and to some extent what relationships do you bring to the business.

Kevin: [25:34] Going back to that. You had this business idea. You decided to accept the offer to get into Techstar. Techstar, I think their standard terms are six percent and throw in $100,000 convertible note. Is that correct?

Ryan: [25:49] That's correct.

Kevin: [25:50] First, let's just step back. Tell us about the product and what problem you guys were aiming to solve.

Ryan: [25:58] We were trying to solve a problem specific to travelers not being able to communicate when they are visiting a country in which they don't speak the native language. And so, the idea was born out of my own unfortunate travel experiences where I get very, very sick while traveling abroad in China and couldn't communicate with any pharmacist due to the language barrier.

[26:26] I obviously survived that experience, but it got me thinking about what solutions were already available for people like me who love to travel, love to communicate and interact with people from all walks of life, but don't necessarily speak every language under the sun.

Kevin: [26:43] Sorry to interrupt you, but I had an exact experience that you had in Japan, in Tokyo. I never get sick and I'd been snow skiing for a week and struggling to find the right foods to eat and I got so sick and I could just not communicate in a pharmacy. They gave me some pills, it was just on a wing and a prayer. They sort of worked, but that was the exact issue. I would have loved your app at the time.

Ryan: [27:06] Yes, you definitely felt the pain point then. So, we looked around and said OK, you know, there's machine translation, things like Google Translate, which at the time and to some extent today, they weren't really all that high quality.

[27:21] On the complete other side of the spectrum, you had very, very expensive call centers staffed by professional translators and interpreters, but the price points were astronomical. So, for a consumer traveling abroad, you were sort of stuck in the middle.

[27:39] Our focus was to take the best of both. Take the sexiness and the technology and the sleekness of a Google Translate, but have the translation itself be powered by real people. And so, we built an app that enabled travelers to instantly connect with another person that, that person being a live translator/interpreter to help them facilitate a discussion across language barriers.

Kevin: [28:10] You guys hit upon a problem that a lot of non-technical co-founders hit upon is that you were missing a technical member of your team, right?

Ryan: [28:20] We were. Neither of us were technical by nature, and being in a technology incubator like Techstars, you obviously need to grow fast, and to grow fast, especially when you're talking about building a technology platform, you need people capable of helping you do that. That was a big concern of ours going into the program.

Kevin: [28:42] How did you guys, it's one of the questions I see on the startup groups the most, is "How do I find a technical co-founder? The demand for smart technical people around the world is just through the ceiling. These people are just so sought after. How did you find your technical co-founder?

Ryan: [29:02] We actually never had a technical co-founder, but we did hire a number of technology colleagues, professionals. The way it worked for us was being in Techstars coupled with the passion that we had for our own specific business gave us a little bit of credibility in the community.

[29:21] If a company is able to get into Techstars, they must have something going, which that was kind of the mantra at the time. And so, when we got into Techstars, we received hundreds of indications of interest from technology professionals to join the team. We found a couple actually based in Boulder that summer, who worked out phenomenally well and joined us full time after the program ended.

Kevin: [29:45] I think a lot of people don't realize you can actually, and of course, it requires a little bit of funding, but you can hire someone and then retrofit a co-founder onto them, bring them up as co-founder after they've started out as an employee, technical employee, and did well.

Ryan: [30:06] Exactly. You see someone do well, you want to make sure that they're engaged and excited about the business. I've see a dozen or so businesses in the last couple of years that I know personally where someone who came on as a fairly mid-level technology professional ended up taking a very, very senior CTO or VP of engineering role.

Kevin: [30:26] So, you guys went to Techstars and you had this idea. I liked one of your demos you spoke about where you were doing a live demo, which is always risky even if it's just a SaaS product, let alone something where you're tapping into a human network.

[30:46] Your first go of it, no one answered the call. No one actually...didn't deliver, but then you tried it again and you got someone good at the end of the line. You obviously impressed people with your demo.

Ryan: [30:59] That was a very memorable experience. We were in a conference room at a technology meet-up in Philadelphia. We had a live demo. None of the translators picked up the phone the first time we were around.

[31:14] The way it typically works is if the first translator available doesn't pick up, the technology cycles to the next one, the next one, until someone gets your call. No one picked up. I was standing there on stage. I turned bright red. I was embarrassed. I luckily made a quick joke that our translators were being bashful.

[31:34] We decided to try again. You could hear the audience just pause, hold their breath like, "Oh, God, please let someone pick up and save this guy on the stage." Fortunately, they did. It was one of our best translators who picked up. She gave a perfect translation. The rest, we were off and running, but that was one of the more interesting and memorable moments from our early days.

Kevin: [31:59] At least, it gave you good content for your book, right?

Ryan: [32:01] Exactly. [laughs]

Kevin: [32:01] A colorful content for your book.

Ryan: [32:03] Exactly.

Kevin: [32:03] I also say that to my girlfriend when we meet a lot of bumps on the road. I go, "It's going to be a great chapter." [laughs]

Ryan: [32:09] Exactly.

Kevin: [32:13] Take us through big picture from there on out right through to your exit and where you're at the business side of things and the product, what happened to it, and where it's at today.

Ryan: [32:27] Sure. We took the business through Tech Stars. We went on "Shark Tank," which is a TV series here in the US on ABC, and decided to turn down a couple of the deals in the aftermath. We ended up raising $1.4 million from a bunch of great angel and small institutional investors. That gave us about two to three years of runway. We did a smaller convertible note, another $800,000 or so. We raised about $2.2 million in total between 2012 and 2016.

[33:04] Coming towards the middle to the end of 2015, my co-founder and I decided it might be worthwhile to look at exit opportunities. We put some feelers out there, connected with an acquaintance of mine, who is a CEO of another technology company. He and I have become somewhat friendly over the years.

[33:30] When he learned of our interest to position our business inside of a larger company, we had a number of good discussions, a lot of bad discussions, bumps on the road, moments when the deal was dead or was going to fall through. At the end of the day, they acquired our company in May of 2016 and have completely assimilated the product, the team, and some of the technology into their own business, where it sits today.

Kevin: [34:00] We got a lot of questions around what is their product.

Ryan: [34:06] They provide a translation software that enables companies to utilize technology to translate their content, whether or not their companies themselves provide the translators or if they lean upon our acquiring company to find the translators.

[34:27] This company that acquired ours was a very, very successful in building software specific to translation management. The nice natural tuck-in for us was a lot of their clients were looking for translators to do the work themselves.

[34:46] Our acquirer initially didn't have a great solution for that. We also provided a much more near-instantaneous quoting tool to help companies figure out right away what it was going to cost to translate their content. Both of those made for a natural tuck-in.

Kevin: [35:06] Was it the type of exit that you had hoped for, in terms of ROI for your investors and obviously, for your own sweat equity and blood, sweat, and tears?

Ryan: [35:19] Now, at the end of the day, when we started the company, we thought it was a billion-dollar company. We were certainly not acquired for a billion dollars. From an ROI perspective, especially on our supporter's capital, we had higher aspirations, but it was still a very nice exit.

[35:35] It enabled us to be proud of the technology and the team we built and to place it in another company. It gave the entrepreneurs behind the business a tremendous learning experience. All in all, we're very, very happy with it, but yeah, mixed emotions along the way, for sure.

Kevin: [35:52] Why did you guys decide to exit? You speak in your book about this. It's definitely one of the big questions that an entrepreneur faces a lot, almost even as soon as you start getting some traction. Business is all about timing, as you know.

[36:13] You think about there's the option to get more funding and to build out. There's the option to sell it. There's the option to keep on going. These are difficult questions. What made you guys decide, "Well, this is the time for us to seek an exit"? Was it personal? You guys were burned out. Were there other factors in the mix?

Ryan: [36:37] It was a combination of both. On the personal front, we had been burning the midnight oil for four years. My co-founder and I worked tirelessly throughout the days, the weekends. Over a number of years, that does take a toll on you.

[36:54] There was certainly a personal side to it, but the real reason to pursue an exit was we felt like we could grow a lot faster and achieve our objective a lot quicker as a part of a larger organization, rather than just being a standalone entity.

[37:12] When we looked at our growth rate, our trajectory as an individual company, and we compared that to what would happen if we aligned ourselves with a company with a bigger customer base, for example, what that would do for our own prospects. It naturally made sense to us.

Kevin: [37:31] You guys didn't think of getting more funding and to build it out yourself?

Ryan: [37:36] No, we didn't. We had raised enough at that point. For what we had raised, we had higher growth trajectory aspirations. Rather than go back and reformulate again, we stumbled upon a great relationship with our buyer.

Kevin: [37:52] A few aspects in your journey as well which were quite interesting that I don't think get spoken enough about, particularly, you speak quite a lot about your girlfriend, who's now your wife. She seemed like she was a real rock for you in the heady early days of it all.

Ryan: [38:12] Yeah. I always like to say she was our biggest investor. She invested her love, her heart, her emotion not only to me but to the company and our team. She was our biggest advocate. She was always there for me, for sure, but also there for my colleagues, hosting events for them as well.

[38:34] Anyone out there who has ever tried to start a business or has started a business knows there's a lot of highs and excitement that goes along with building a company from the ground up, but there's also a lot of lows.

[38:46] I've always believed that the successful entrepreneurs are able to balance the highs with the lows to remain even-keeled throughout the journey. She taught me a lot about that. She allowed me to remain even-keeled. She was a huge supporter.

[39:02] I've seen it the other way, too. I've seen entrepreneurs who are significantly smarter and more successful than I'll ever be, but their loved ones aren't all that supportive. They don't like that lifestyle. They don't understand that risk profile. That takes a toll on the entrepreneur himself or herself.

Kevin: [39:20] I've seen that as well, where partners just aren't empathetic to the journey. It's fair enough. It's not their choice. It's not their journey, but at the same time, the reality is that the entrepreneurial journey is all consuming.

[39:36] I heard an interview the other day with some chap that had built out his business and sold it to, I don't know if it was Salesforce, eventually for a lot of money. He said, "Through all these 10 years or whatever it was, I was always waiting for the time when we would just hit that smooth wall and be plain sailing for six or eight months. It just never happened. It is quite an intense calling. The toll on family and friends is pretty significant.

[40:09] I went to a talk a few years ago by Frank Lowy. You might not know his name, but he founded Westfield shopping centers in Australia. He's one of Australia's most successful entrepreneurs. Post war, he started with nothing and now has the biggest shopping center company in the world.

[40:28] In his talk, one of the first five minutes, he spoke about his wife and how she has been amazing. One of his big boats, actually, which I see in the Sydney Harbor every now and then, is named her. It definitely came through as a positive.

[40:46] What came through as well is that you were lucky enough to be born into a family where your father built a business and you saw what was possible with hard work. You saw what was possible by just -- I say this in a positive sense -- an ordinary guy just applying himself and working hard, right?

Ryan: [41:06] Yeah. I've always said we're all a sum of our environment. I was very fortunate enough to be raised by two parents that enabled me to become an entrepreneur. I learned from my father's experiences. My mother taught me everything there was to learn about the nuances of education and how to grow a business. I was very lucky. Not everyone is that lucky. I realize that, and I very much appreciate that.

Kevin: [41:31] You're in Florida now. I'm talking to you in Florida, right?

Ryan: [41:37] That's correct.

Kevin: [41:39] You guys went from New York to Boulder for some of the Techstars stuff. How did you guys land up in Florida?

Ryan: [41:51] We actually started in Philadelphia when I was in business school, went to Boulder, then we actually relocated to New York, just given the international city that New York is and how that aligned nicely with our international focus, our language translation focus.

[42:08] After we sold the business, and actually a little bit before we sold the business, my wife and I, we had had enough of the rat race of New York. New York is a fantastic place. I could definitely see myself going back there in the future, but after having lived there for 8 to 10 years, off and on, we both wanted to try something a little bit newer.

[42:29] We had talked to a lot of people down here in Miami about the growing entrepreneurial culture. There's certainly a great lifestyle, an outdoorsy culture. On the personal side, I like to take part in triathlons and running events. There's a lot of that down here, just given the weather. We moved down here earlier this year. The rest, we fell in love and now we're permanent residents.

Kevin: [42:56] You'd really love Australia, particularly Sydney. It's good weather. Everyone has outdoor lifestyle. Have you ever visited?

Ryan: [43:02] I'm visiting in March...

[43:04] [audio cuts off]

Kevin: [43:06] welcome. Drop us a line. I'd love to show you some of the sites. I think you're going to love it.

Ryan: [43:11] Perfect. I will definitely be in touch then.

Kevin: [43:15] What's next in store for you?

Ryan: [43:16] I'm currently working on the next entrepreneurial venture. The last couple of months have been truly exciting for me. I'm starting a new company and getting to flex some of those muscles in the brain that I haven't tapped into in a while. The things that you forget, you have to do it the early stages. I'm having a ton of fun taking the next business off the ground.

Kevin: [43:40] What's the startups seem like in Miami? I visited Miami once. You don't hear that much about Miami startups and big exits from it. There's that one VR company that's been in the press, the Magic Leap, I think it is. They're based in Florida somewhere, but what's the tech startup scene and startup scene in general like there? You mentioned it's growing.

Ryan: [44:01] I would say it's burgeoning and growing. Miami is a sprawling city, unlike Philadelphia, for example, where there's just so many academic institutions centered in a very small area that there's just so much talent and access to capital.

[44:22] It's a little bit different when you're in a larger city, but there are neighborhoods, there are communities, incredibly impressive communities down here with entrepreneurship. You just have to seek them out a bit more. I would think about Philadelphia, New York, San Francisco, Boulder, and a handful of other US cities as tier one places to start a company. I would say Miami is not quite tier one, but it's on its way.

[44:51] One of the main reasons why I wanted to come down here was to play a very small role in the growth of the entrepreneurial community and also be inspired by entrepreneurs from all walks of life. Miami is a very international city. Tremendous Latin American imprint here. There's a lot to be learned.

Kevin: [45:12] Yeah, it's a fantastic place. I went down there for a long weekend when I was in New York for a couple of months last year. Really, what surprised me was it does feel like a Latin American city. It's fantastic.

Ryan: [45:27] It is. It's like being abroad but being in the US, so you get the best of both.

Kevin: [45:31] I did say I got some strange looks, though. I'm vegetarian most of the time. I got some strange looks when asking for some vegetarian food. [laughs] It was a little bit different to some of the hipster suburbs of New York with raw food and macrobiotic food and everything. That was a little bit different.

Ryan: [45:50] Exactly. You don't want to tell someone you don't want their empanadas down here.

Kevin: [45:54] Exactly. Ryan Frankel is the author of "The Making of an Entrepreneur, Lessons from a Winding Journey Towards Entrepreneurship." I got through about 49 percent of your book, squeaked it in over the last couple of days. I look forward to reading the rest.

[46:09] Ryan is also the former CEO and co-founder of VerbalizeIt. I appreciate you joining us on the show. Good luck with the next stage of your journey. Please enjoy Australia and reach out to us.

Ryan: [46:19] Perfect. Thanks for having me on the show. I look forward to talking soon.

[46:57] [commercial break]

Kevin: [46:57] Maybe it's because I'm an entrepreneur for my sins, but I never get bored of hearing other peoples' journeys. Everyone is unique. There's obviously common threads, one of which is you have to work really, really hard.

[47:17] I always find these people have surprises. Things either go better than they have expected or probably a little bit worse than they expected. Another common thread is you need your supports team as well. Ryan spoke a lot about his wife. I spoke with him about that, about the support team.

[47:35] They're all unique in their own way. I enjoy hearing the journey from thoughts to execution. They were lucky that they actually got an acquisition. They got an exit out of it, which very few businesses get as well.

Kate: [47:47] I find it interesting, too, that he made the point they have to take the ups and the downs. I feel like the whole entrepreneurial thing can sometimes get a little bit essentially sparkly and amazing, but people would forget that there's a lot of downsides, too, that you have to deal with.

Kevin: [48:06] Yeah, but like a lot of things in life, the glamour is what people notice. Even the rock star lifestyle, if you look at famous musicians, that on the road, it looks very glamorous, but you speak to any musician that's been on the road, the glamour goes out really quickly.

Kate: [48:23] It's like that famous picture of the iceberg. Have you seen that?

Kevin: [48:27] I think so.

Kate: [48:28] People captioned it. What people see is just the tip. It's all nice and clear. Then underneath the water, you see how big it is. They captioned that like hard work and perseverance and a lot of stuff.

Kevin: [48:39] Yeah. As David Heinemeier Hansson said in last week's podcast, it's easier than ever to start a business. He said it's not easy, but it's easier, right?

Kate: [48:51] Easier now.

Kevin: [48:52] It's easier now. You grew up in a family with the father that owns a business as well, so you probably have some sense of the ups and downs.

Kate: [49:00] Yeah. It's a different industry altogether.

Kevin: [49:04] It's not a tech business...

Kate: [49:05] No.

Kevin: [49:05] but still, a business is a business. You need more money in than out. You have staff issues. You have all those issues.

Kate: [49:12] Definitely. It's interesting to watch him and learn hard work and how it pays off and managing people.

Kevin: [49:23] Which is the trickiest one...

Kate: [49:25] Yes.

Kevin: [49:26] Which is the trickiest one. We're taking a little bit of a digression, but Facebook today reaffirms Sheryl Sandberg. She's the Chief Operations Officer. I'm not sure what her official title is, essentially, the 2IC to Mark Zuckerberg.

[49:42] She said that they're rolling out a whole new bunch of benefits for staff, including four months paid paternity and maternity leave, a whole bunch of bereavement leave, so that if someone passes away close to you or even one step away from you and carer's leave as well, a whole bunch of this paid leave...

Kate: [50:07] On top of annual leave?

Kevin: [50:09] On top of annual leave, yeah.

Kate: [50:11] Wow!

Kevin: [50:11] Saying that their staff are their biggest asset. They're looking after them. I think their intentions are genuine, but it's also because they want to hang on to their good people. It's a competitive thing as well. Even for companies like Facebook, they have to get creative around the staff side of things. It's definitely the trickiest side of things.

Kate: [50:36] I've seen a few personal social media lately of these bigger companies and the packages they give people when they're going on maternity leave. One from Spotify had a little T-shirt. It said something about welcoming the newest band member or a little pair of headphones and stuff. They're really going all that to make people love their job.

Kevin: [51:01] It's great. The downside or the challenge, I should rather say, is as a business, you have to have resources for that. Not all businesses do have resources for that. A lot of these businesses are funded or they're highly profitable, but there's definitely value in creating a company that factors in that people have lives.

[51:25] You do have to first get an escape velocity. There's a saying in business that for four to ten years, you have to work more than ever, so that after that, you can pull back and you can work less than ever. You have to achieve escape velocity, which means you have to overcompensate and do a lot.

[51:48] Yes, it was interesting that Ryan grew up exposed to that. I also grew up with a father that started a business as well. Just as Ryan said, he said that his father was an ordinary guy that achieved just by working hard and treating his staff well. It's the same, that's what seeing my family with their business.

[52:10] If someone's listening to this podcast, I promise you that the people that are starting businesses, you're not more stupid than them. It's very unlikely.

[52:18] Go for it, if you've always wanted to. We always say on the podcast the only person that's not allowed to go for it is Kate, because she's my right-hand person.

[52:27] [laughter]

Kevin: [52:28] I'm kidding. I'd always support her. It's definitely one of the challenges in our industry. We've had two of the technical team members, James and Charl...

Kate: [52:39] Both start their own businesses.

Kevin: [52:41] Both went to start their own businesses, so it's definitely a challenge in our industry.

Kate: [52:46] Interesting to see how they're going.

Kevin: [52:48] It's interesting. I think they're both going pretty well, both super smart guys. They are missed in the tech team.

[52:56] It is a challenge in our industry. If you're listening to this podcast, and you've also always wanted to start a business, it is easier than ever. David Heinemeier Hansson gave some tips last week how to bootstrap it.

[53:09] Ryan Frankel, it's interesting, different to David, is very pro bootstrapping and going at your own...They did raise some money. They weren't technical people, so they couldn't code it up themselves.

Kate: [53:22] They needed help.

Kevin: [53:23] They needed help doing that, whereas David is a super, super smart, technical person. It helps if you can actually, in a way, do the work yourself.

Kate: [53:34] It's a huge barrier, too. Not always, but often, the people with the ideas don't always have the skill set to make them happen. They've got to find someone else to help them. Then, you've got to rely on that person and have the money to pay that person. It's snowballs effect.

Kevin: [53:49] It does. That's why, in the early days, for a tech business, if you're the one that can code it into, learn how to code to prototype is not impossible. You don't have to be the best coder in the world to create a prototype that someone can look at and say, "Wow, I'd love to use that," or even someone to get one person to pay for it.

[54:09] If you just get one person to pay for it, that's a very, very important signal. You can create things or you can get an outsourced person through Upwork at $5 an hour, $10 an hour to create a prototype. There are ways. You've always got options. If you're hungry enough, you've always got options, but some...

Kate: [54:28] There's plenty of design programs to try to make the coding process of websites and prototypes much easier. You don't actually have to touch the code. You just move elements around the page and that's kind of thing.

Kevin: [54:46] As always, these things are not easy to execute on.

[54:52] Anyway, that's episode number 80. Thank you for joining us. You can head on to the show notes at itsamonkey.com. The single thing that helps us most is if you put a review on iTunes that helps other people discover this podcast. Also, tweet us, email us. We love to hear from our listeners, and we will chat to you next week.

[55:13] Thank you very much.

Kate: [55:14] See you later.

[55:15] [music]