• 50:05

Episode number: 6

Funding & Maintaining Startups

with Tracy Osborn


Tracy Osborn, designer, developer and founder of WeddingLovely.com, stops by the show to discuss what it took to build and launch her own startup. We discuss her career transition from employee to freelancer to startup business owner, as well as funding options, ups and downs of running her own company and, finally, what success means to her.


Sponsored by

  • Solspace
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Episode Transcript

CTRL+CLICK CAST is proud to provide transcripts for our audience members who prefer text-based content. However, our episodes are designed for an audio experience, which includes emotion and emphasis that don't always translate to our transcripts. Additionally, our transcripts are generated by human transcribers and may contain errors. If you require clarification, please listen to the audio.

Lea: You’re listening to CTRL+CLICK CAST. We inspect the web for you. Today we are talking about startups with special guest Tracy Osborn. I’m your host Lea Alcantara and I’m joined by my fab co-host.

Emily: Emily Lewis.

Lea: This episode is sponsored by Solspace. Solspace is a ten year old…

Lea: You’re listening to CTRL+CLICK CAST. We inspect the web for you. Today we are talking about startups with special guest Tracy Osborn. I’m your host Lea Alcantara and I’m joined by my fab co-host.

Emily: Emily Lewis.

Lea: This episode is sponsored by Solspace. Solspace is a ten year old web development firm with experience in the most challenging of project settings. Solspace builds versatile tools that elegantly meet complex needs. Solspace happily serves mom and pop shops and Fortune 100 multinational organizations with equal ease, effectiveness, respect and craftsmanship. Visit solspace.com to find out more.

Emily: CTRL+CLICK would also like to thank Pixel & Tonic for being our major sponsor of the year. Hi Lea how are you doing?

Lea: Pretty good how about you?

Emily: Not too bad. So I know that the last time we talked you were getting ready to head to Portland for ExpressionEngine Conference and Refresh Portland, how did everything go?

Lea: It was really great. I thought that a Brad Parscale and team did a great job running the conference considering it was his first conference. So everything ran really smoothly and it was great to see the gang back together again. Always feel a little bit like family reunionish whenever the ExpressionEngine community gets together. So I also came away with stuff that I could work on right away too and so whenever I go to conferences I don’t really expect to say learn something brand new perhaps, but perhaps getting reminders from people what you should be doing or even just best practices over how they run their business or their development and that was always really good.

Emily: What was the highlight for you? I mean, other than seeing everyone.

Lea: Something’s just specifically I thought Matt Weinberg talk on SEO stuff was really good. That comes to mind immediately because I immediately emailed you right after saying we need to do this. So whenever there is something that’s actionable I think I think is always really useful. So that came out of my mind that I thought wow I’m really glad I went to that talk.

Emily: And how about the Refresh Portland where you gave your branding presentation?

Lea: Well Refresh Portland was really great. It was a small little meet up about maybe like 16 people, but I really like that because I was able to have a lot more interaction and a lot more discussion this time around and I really made an effort to make sure that this time around this presentation was less of talking at people. I think it made it a much, much better experience. I also broke into song.

Emily: No kidding. Did you really?

Lea: Yes because the title of the presentation is called Getting to Know Brand You.

Emily: Oh my God, you sang that song.

Lea: And I sang Getting to Know You from The King and I. [Laughs]

Emily: Oh no I really wish I had been able to go.

Lea: Yeah, yeah so and I sang it with a British accent and everything too. So not even like just singing it normally. I had to do it in Deborah Kerr’s voice. Yeah that was a lot of fun.

Emily: Good, well I’m glad you had a chance to go out there. I had my kind of round of conferences earlier this year. It’s the same for me. I always walk away feeling engaged and inspired and just little ideas of things that I can do. It’s always worth it, conferences I think. Well at least the ones I’ve been too. I haven’t yet been to a really bad one.

Lea: Yeah I know I mean a lot of that is dependent on who goes, I think too. And everyone at the EE Conference in Refresh Portland were fantastic.

Emily: Fantastic. Well let’s get to some news.

Lea: Sure.

Emily: Well we’ve got a little bit of news in our neck of the woods. You and I are starting a business blog series on emilylewisdesign.com and you wrote the first post. It went out live last week where you talked about the process of getting your visa so that you could come and live and work in the United States.

Lea: Yep and for those just turning in to CTRL+CLICK our very first episode talked about how we started working together and we promised that we’d be writing about it so.

Emily: Yeah we did what we promised. [Laughs]

Lea: Yeah exactly. So now it’s out and if you want to find out more about how we run our business make sure you subscribe to emilyLewisdesign.com and we’ll get more good stuff out for you.

Emily: Yeah it will be great. So there is also a bit of news in the world of content management systems.

Lea: Yes before we get into that I just want to mention that we are just having news based on the CMS’s that we are actively following or using and try to keep it to major updates. So if there is like a tiny little build update we won’t really necessarily mention that but if you think that as a listener that we over looked something please let us know at ctrlclickcast.com/contact and we’ll be sure to get it on our radar.

Emily: Absolutely. So the first of the news is from EllisLab expression engine version one support is ending this December on the 7th. So if you are maintaining EE version 1 site you might want to start looking to see if there is anything you need help with right now. [Laughs]

Lea: Yeah or if there is an opportunity for an upgrade path etcetera. It’s going to be a little bit difficult I think for some sites.

Emily: Some sites I think if you haven’t upgraded there is a reason why you haven’t upgraded.

Lea: Yeah for sure.

Emily: Just the complexity of it or something like that.

Lea: Yeah exactly. And in other CMS news Craft seems to be building up to something big for November. They had a post on Pixel & Tonic called Psst [Laughs] and then there is a picture of Guy Fawkes on the front page of Pixel & Tonic. So I’m guessing that means there is going to be a ‘revolutionary’ release on November 5th. For those that don’t know what we are talking about. I think most geeks will recognize that it’s from history as well as what’s that movie.

Emily: V for Vendetta.

Lea: V for Vendetta. So if you don’t know anything about that we’ll link to the Wikipedia explanation in the show notes.

Emily: [Laughs] All right, well let’s get to today’s episode. We are talking about funding and maintaining startups with Tracy Osborn. Tracy is a designer, developer and speaker. She is also the founder of WeddingLovely. A subscription based wedding planning service and one of the F11 class of 500 Startups. Welcome to the show Tracy thanks for joining us.

Tracy: Thanks for having me.

Lea: So Tracy can you tell our listeners a little bit more about yourself?

Tracy: Sure thing, I mean you kind of ran over the basics in the intro. I started out as a designer and then I picked up programming and so I’ve inclined myself as a designer developer which is still blowing my mind being a designer for so long [laughs] because it all just seems like it is this really, really hard thing to get into. Now I’ve kind of officially added it to my title, which is just kind of amazing. An I’m from California, but right now I’m actually travelling through Europe. So I kind of took about one fourth of the year off kind of work and travel, just seemed kind of fun.

Lea: Oh that’s fantastic speaking of Europe like what brought you there, what are you up to?

Tracy: I mean it was like, put my house, the place that I’m renting… I was able to rent it out on Airbnb.

Emily: I love that service.

Tracy: Yeah and then I went to Europe and now renting places in Europe. So it actually works about better because I live in California so rent prices are through the roof. So I was able to rent my place for a good amount of money. So I’m kind of saving money by being in Europe, imagine that. [Laughs]

Lea: That’s kind of an odd statement actually.

Tracy: I know. [Laughs] I’ve been through Brussels and a bunch of Germany and right now I’m in Prague. So it’s been a really good time.

Emily: Was it just something you wanted to kind of change your environment or was there a conference that you wanted to be sure you could attend?

Tracy: I’ve actually missed a bunch of conferences including one of my favorite conferences in the whole world which is Brooklyn Beta. [Laughs] I missed a bunch by traveling. I considered flying in just for that one, but then I realized the plane tickets would be too expensive. But I mean really, founding WeddingLovely I’ve actually been able to travel while working on it which has been awesome and so I want to take advantage of the fact. Say if I was working a ‘real job’ with hours and having to go into my office and what not, I wouldn’t have this opportunity. So I felt like the best time to go out and see the world while working. It’s something I needed to do sooner rather than later.

Lea: So let’s start at the very beginning, how you got to this point. So we talked about how you started you career as a designer. So before we get into how you got into development, tell us a bit about your design roots and how you got started on the web.

Tracy: Sure I made my first website when I was 12 which was the 90’s sometime, I’m not going to do math right now. [Laughs] And this is you know the days of doing template websites and it was very, very new. I discovered when I was 12 and all through our high school that it was fastest way of getting an easy A in any kind of project for high school because everyone was like, oh website you made a website for your project.

Timestamp: [00:10:00]

Tracy: So it was like A’s throughout high school because I was just making websites for all my classes. And I had this idea that, oh because I can do websites oh I can totally program you know in HTML and CSS… well CSS didn’t exist then. So HTML is nothing like programming. But I went into computer science at Cal Poly San Luis Obispo.

This was my first foray into developments and computer science at the time was teaching Java which most developers I tell them about that and they go, urgh [laughs] because Java is not a great language and I hated it. I couldn’t figure it out. I mean I remember one of my second quarter of classes we started talking about GUIs and everything up until this point is in all command line. So we started doing GUIs which are graphical user interfaces and I had this like, oh this is what I’m good at. I actually like making interfaces which is what the class wasn’t about at all.

I made it through a year of computer science and again I thought I hated it and I didn’t really want to do programming again and so I switched over to graphic design and I finished up my degree in graphic design. I was going to be a product designer. I wanted to work on wine labels, but the year before I graduated a friend of mine had a startup and literally a bunch of guys working in a garage and he was like, okay I know you can still do web design and I didn’t actually – I had no CSS at this point even though CSS had been around for a few years. So they said, like you can do some kind of web design, you can graphic design how about you come with us before you finish up college at this ‘startup’… a bunch of dudes in a garage working on this website.

I thought it was going to be temporary. I ended up working with them for four and a half years. They moved from the garage into an office in Foster City in the Bay Area and then right before I left them they moved into a giant office in San Mateo. So they are doing very well and it was this really great – like I guess a kind of a startups intro for me because I had to teach myself web design when I was there. I taught myself CSS. I taught myself how to do web design and how to do conversion testing, how to do SEO – it was just SEO, very SEO focused company.

So I was kind of being thrown into this world and I had no one above me to teach me anything which was kind of actually really, really fun and I liked having that control. So after four and a half years I kind of realized that I wanted even more control. I didn’t want to have a company on my head. So I left them. I did some freelancing through web design for a while and then I decided just to start my own company and try to jump into that. So that’s kind of how I all grew together.

Lea: When you say start our own company you are talking about WeddingLovely.

Tracy: Yeah kind of… so the first prototype I guess is – or I guess the first version of WeddingLovely is actually called WeddingType. Like I must say if I’m at weddings, it’s funny because I looked at weddings a lot of people are like, oh you must be married, which I’m not married. Like, oh you must like really love weddings and want to be a wedding planner, which is not true. Yeah it can be kind of crazy.

But as a designer I love wedding invitations I think invitations are just gorgeous, they are this pieces of print design that have so much tradition and importance around them and so WeddingType. I wanted it easier for people to make their own wedding invitations because there is a lot of people out there who don’t have a design eye or have a lot of skills in that area, but they are still making their own invitations and I saw a lot of these and they are usually like Times New Roman or Courier or something like that.

So the very first iteration of the company was building an online kind of like “typography for wedding invitations.” So a person can put in what they want, their size and they would format it in a very nice way so that it can be outputted as PDF and print it. Now this is all theoretical. So I wanted to build, this never actually happened.

I found a cofounder who can program. I was doing design. We applied for YC and got a – excuse me, Y Combinator – then got an interview, didn’t get in and just immediately after not making it into Y Combinator cofounder and I realized that things weren’t working out so he left.

So then I’m stuck with this very ambitious idea, but no code really and no knowledge on how to program. That was the point where I said, okay you know what I’m just going to learn how to program and I’m going to build my own startup, but I couldn’t build that very ambitious idea because doing perfect typography outputted as a PDF is very, very difficult. I decided to switch to something a lot more simpler which is a place to showcase really great wedding invitation designers on a directory which is a lot easier to build by a programmer.

So that is weddinginvitelove.com. It’s a wedding invitation designer directory which still exists now. It was the very first thing I ever launched and now WeddingLovely is officially eight different websites, a bunch of different directories and a bunch of other things too. And I had to change the name of the company from WeddingType to WeddingLovely when it was out of doing just invitations into supporting wedding planners and wedding photographers, wedding venues and what not.

Emily: Wow so when you decided to teach yourself to program what did you start with?

Tracy: I was so like a little bit scared from Java [laughs] and luckily I started dating someone and he is still my partner today, but he is a really great Python programmer and so he kind of just started showing me a little bit of why Python is a lot easier to pick up because it’s a very clean and beautiful language and it’s so much nicer than Java and it’s not even funny how much nicer it is. So much easier to pick up. I didn’t try to understand all of Python and Django is the specific platform I’m using and I didn’t play with all of it. I actually I launched about six weeks after I started I decided to learn programming and I basically got this like very, very simple MVP version of the website out which was quite fun. It’s more fun I find to have a live working website out there that people can use kind of really inspired me to keep working on it. Now this was just a side project at this point. But I use Python and Django and I know a lot of people like Rails. I’ve tried learning Rails and I don’t know it still. But I still Python a really, really great language to learn.

Emily: How long did it take you to feel or maybe to build your most, for lack of a better word, tangible thing. Like what was the learning curve for you the time frame?

Tracy: So I mean the tangible thing – the first version of WeddingInviteLove launched six weeks I would still consider myself barely knowing anything, but I did get something out there.

Emily: That’s cool.

Tracy: So that was really great and then it’s just kind of interative process where people I worked with would ask for features. So either a wedding invitation vendor or a user would be like, hey I really think you should use this and then I would learn more Python and Django by building that feature. So I have to do a lot of Googling on how to do something like that and then I try to hack it together and see if it worked, but during this process essentially teaching myself Django and Python while working on WeddingLovely.

So it took six weeks for the first product to launch. I kept iterating on that and then the big turning point is this second major product. Consider the first major product today is a vendor directory which WeddingLovely has eight of those now. And then the second major product is weddinglovely.com and this was launched about two years after I did WeddingInviteLove and what weddinglovely.com is, it’s like an online planning and guidance app. So someone can put in their wedding date and they are looking for an eco-friendly wedding and then they live San Jose, California and it kind of creates a little plan for wedding planning. So they can say okay, I am eight months out, these are things that I need to have done, be doing you know, immediately. These are things I can just wait on. So find your photographer and venue first work on other things later, and it was my goal to kind of build something so people can have a plan for wedding planning. It’s going to really involved and kind of scary process because there is so many like pieces you had to put together.

Building that was a lot more complicated that building a directory because while, A, I’m working with customer with all their information and then I had to build this like if this person is in this place of wedding planning then he needs to surface up this template and then the person needs to be able to mark the template as like we don’t need that template anymore and it was very complicated. When I worked on that I’m like, oh my gosh this is so much easier and I realized how much at that point that I learned Python and Django and it was kind like this, Ahh! And I think at that point that’s when I changed my Twitter description because it used to say designer and part-time developer and when I did that I kind of realized myself that I could change it to designer AND developer taking out the front, and I remember doing that being like, oh my gosh I actually am a developer. So it’s been three years of working WeddingLovely now and I can still consider myself the intermediate programmer. But I guess what I’m trying to say is I’m very happy with where I am right now, it’s really, really fun.

Lea: So you are talking about Python and Django, do you have any specific resources or tools that helped you hone your skills?

Tracy: Yeah there is two places that exist that I used. One is called Learn Python the Hard Way which is the title is kind of…

Lea: It’s kind of intimidating there.

Tracy: But it’s actually like learn it the easy way. And it’s a very, very simple like introduction into programming logic and so I needed that refresher because there was logic in Java and I kind of had a knowledge about how for loops and if statements work, but it was my refresher into learning how that works in Python and its free online. I think you can buy a book, highly recommend it.

And the second thing I used at the time was a tutorials… I think it’s called Getting Started with Django by Kenneth Love and he is currently working on a video series rehashing those tutorials so is a good intro into Django and how Django works in terms of building a web app. So the third thing also, is that yeah this didn’t exist then because I’m hoping to build an introduction into Python and…

Timestamp: [00:20:00]

Tracy: …Django for web designers and so I’m actually working on a book right now. I’m shopping around for publishers which is a little scary, but taking the knowledge that I learnt from learning Python and Django. I find that a lot of these – lots of tutorials for Python and Django for build web apps are kind of based on other programmers. So I kind of jumped into all this programming terms that’s very confusing to say a web designer like I was and so I’m kind of creating right now a tutorial that helps web designers pick up programming and that kind of speaks the web designer language. So that’s not out yet, but that’s what I hope we can work on and it will help more people go through the same process I did.

Emily: Since you went through this process and you seem to be – you seem too really like it, the evolution of your skills… is it something you would recommend to any web designer to pick up programming?

Tracy: I find a lot of web designers and I especially did, you work in the web and you keep being like, I wish this product existed. I have these constant ideas of things that should exist and the fun thing is that if you’ve done programming theoretically you can build it. You can build the things that you wish exist and it’s actually quite fun because as a web designer you control only the front and interface, but then when you pick in programming then you control the whole thing, the whole interaction. It was really exciting for me to build this full system where not only was I building what people were using on the front end, but building the actual web app themselves.

So any if any web designer out there had this ideas for something you can pick and build I would totally recommend learning Python and Django or Rails and Ruby or another language that’s out there. Because it’s so much fun to actually build a web app I find at least very fun and it allowed me to not do any like full time freelancing anymore. I turned it to my full time job. I mean I don’t make that much money, but I’m in Europe right now and I’m able to travel with it which is awesome so if anyone has the idea that maybe jumping in and learning programming I’d say totally go for it.

Emily: I have a question about startups in basic definition of them – what defines a startups and I guess my point of reference is both Lea and I have had our own businesses are those considered startups? What’s the difference between a self independent employed person and a startup?

Tracy: I actually have no idea. [Laughs] Depends on what you want to call yourself. I don’t know if I’m a startup anymore. It is kind of a buzz wordy term that you kind of think of the Silicone Valley startup that’s raising millions of dollars and that’s going to you know either flame out in one year or sell to a big company for a 100 million dollars in two years or something like that which I mean it seems both of our companies don’t really fit that definition. But who knows maybe it’s an inspiration term, all this like ideas, I’m very excited about building something. I mean I guess I don’t know but you know whatever you want to call yourself.

Emily: Having been a freelancer for a period of time versus what you have done with WeddingLovely are there any differences or benefits that having the startup that you didn’t have when you were freelancing?

Tracy: Its funny because in both cases I’d say I’d be working with ‘clients.’ When I was a web designer I was working with someone, but say its building something that they are building themselves. So I mean as a web designer someone has an idea of building a to do app and so I will be helping them build the front interface for it. So I’m kind of helping them achieve their vision whereas now it’s my vision and I can work on what I want to build and I have a lot people who kept emailing me saying, hey I really think WeddingLovely should do this and support this and what not, but I have like the choice in whether I really want to jump into doing that and sometimes I do. It’s really great actually to get a customer emailing me like, hey I really think you are missing this and I actually put it up that night and I send an email the next day I’d be like, hey its actually live and they are like, oh this is awesome. Its more control and I think it’s really fun – you know I pick and chose what I want to work with and what kind of features or where I want to grow.

Lea: It really feels like pursuing your passion when you had this idea, but I feel like in the world of startups it’s kind of like a chick and egg thing. Do you find startups have more people pursuing a passion for an idea or is it really a passion for entrepreneurship in general?

Tracy: I think it depends on the idea. The funny this is that I get a lot of people who ask me, like why weddings you must love weddings and a lot of it is I want to change the world of weddings and make them simpler and a little bit less insane. I love working with wedding vendor’s especially small business and local wedding vendors, the people who are kind of its hard for them to get marketing or get out there because it is like another one person working on their company. Both are very important and if you don’t have the passion for entrepreneurship to do a startup probably you’re not going to get very far.

I was working with someone before and it didn’t work out because it felt like that person really needed to have the strengths of having a company around them, a lot of stability. So you need to have like this ability to be like, I’m going to be without stability and without a lot of rules and be able to be work a lot in the freer and maybe scary environment. Also important to be really interested in the idea that you are working on because that’s where I think a lot of the creativity comes from.

If you are not interested in the idea, you’re not going to be passionate about figuring out what is missing from that field and so I find a lot actually with weddings. I run into a lot of people who look into weddings, I talk with a lot of startups and they look into weddings like, oh people spend so much money here I’m going to start a startup here because people spend money it’s going to be so easy to make money. And I can kind of tell they are not interested in the idea of the weddings more of themselves they are interested in the money and more often times than not these startups stop existing after a year because they find out it’s a lot harder. It’s not just like money is being thrown at them. It’s a lot harder to make money and then they go under. I mean when WeddingLovely kind of was launching there was probably say eight or so of other startups at the same time they are starting at the same time and majority of those don’t exist anymore. And I think for me one of the problems might have been the founders were more into it for money than being really passionate about the idea themselves.

Emily: So speaking of money when you were coming up with first of all these directories you mentioned and then WeddingLovely like where did you get the money to pay for I mean ultimately your time, but then anything else you needed to do.

Tracy: Well luckily so I guess that I had that one job that I worked for four and half years and when I got the idea that maybe I wanted to go do something on my own I started saving money. So I had about $20,000 dollars saved up by the time that I left that job which is kind of hard to do when I only had – let’s see I was only making $15,000 dollars a year. So it took me a few years to get to that point. But I left my job with a nest-egg saying okay I have more or less half a year to a year depending on how I save and scrimped to have something happen. And the second thing is that when I launched WeddingInviteLove that first directory I was still doing part time freelancing so I could still make money. so I had that kind of a backup in case things didn’t work out and so once WeddingInviteLove I launched paid profiles and when I started growing I was able to cut back more and more on the freelancing and then the big turning point was when I was accepted into the 500 Startups Accelerator and like you mentioned the fall 2011 batch and I had my one and only investment which was 50,000 dollars for a piece of my company to be inside the accelerator. So at that point I was able to stop freelancing and just live off of that investment.

Emily: Can you describe 500 Startups a little bit for our listeners?

Tracy: Sure thing. It’s a startup accelerator so it’s kind of summer school for startups. I forget how many companies, it must have been something like 20 or so companies in Mountain View, California and they all came together for a three month time where there is a pilot class is going on every day. So every single day there is some kind of events. They are bringing a speaker and the speaker talk about SEO or talk about conversion or talk about design and so you can attend this session’s kind of all work together in this big room on your startup and at the end of three months then we have this thing called demo day so you debut what you’ve been working on for the last three months to a – actually we had three demo days, so rooms of investors with the hopes of raising a seed round between 500 and a million dollars or more depending on how awesome you were.

I ended up not losing money which was not a function of 500 Startups themselves I had the opportunity, but its other than that the program was really great for me to meet other people in the startups worlds and it’s also kind of like a stamp of approval for your company when you accepted them into a program like this because will say, if 500 Startup likes you that must mean your company is really great and so it kind of opened a lot of doors.

Emily: So you had to come to 500 Startups with your idea first.

Tracy: So I got a little bit lucky, before 500 Startups I was accepted into a program called, I guess it’s a little bit different now, but it’s called The Designer Fund. They are kind of looking for designer founders that they could support and kind of help them grow their companies. It’s because designer founders are very, very rare because usually yeah when it comes to starts up usually you know we have like the CEO the marketer the type person, the CTO the programmer type person and so designers have been kind of traditionally left out of that equation. So I joined The Designer Fund which is an awesome program and now they are working on a thing called Bridge. So they are a little bit different. The Designer Fund has a lot of connections with 500 Startups. One of the founders of Designer Fund used to work with 500 Startups and so when I was accepted into that program I was able to get immediate interview with 500 Startups through that. So that was the first door that opened up…

Timestamp: [00:30:00]

Tracy: …to me. So then I had that interview with 500 Startups and they accepted me from that interview into the program which was kind of awesome because I’m a solo founder as well and usually these accelerators they all look for someone with a partner. So it’s kind of its like really, really great awesome moment.

Emily: You mentioned you were a solo founder and that’s less common than someone with a partnership. Do you know why they seek someone with a partnership?

Tracy: They like to say their chances of success are higher which I’m not sure but when you have a partner with you especially when you’re going through ‘like real startup’ you know those big scary exciting ones where like everyday it’s a little bit different like one day it’s amazing and everything is going great and the other day, urgh everything is going horribly. I lost these customers. The company is going to fail and so it’s like this giant rollercoaster and if you have someone going along that rollercoaster with you it makes it so much better because you have someone to talk to who understands.

There is also you know when you are kind of partner you are sharing the workload and so if someone can work on the marketing. You know one of the person working on the programming, you work together you theoretically get a lot more work done. Like I said I decided to do it myself and so I kind just started doing marketing, programming, designing all of myself and I’ve never been open to the idea of a cofounder but the other problem is that it’s hard to find say ‘cofounder’ when they haven’t started the company with you from the very beginning. It’s kind of hard to feel like a founder or something when it’s already been existing for three years underneath another person. So that’s another reason why I’m still continuing to be a solo founder and sometimes I wish I had a cofounder what not but other times I have gotten so far on my own and I really like doing things myself. Maybe [laughs] I kind of like controlling it, so it’s kind of a theme. So kind of happy of how things have gone and again I got into 500 Startups without a cofounder, which was great and there is few other startups in there without a cofounder including a couple of other women run startups that had no cofounder which was even more, so it was actually really great to find people like that in that program who were like me.

Lea: I’m curious about the initial investor who invested what $50,000 dollars you mentioned towards WeddingLovely.

Tracy: Yeah 500 Startups themselves.

Lea: Yeah so how does that deal work? So they give you $50,000 dollars how do they expect to get a return on their investment.

Tracy: So it’s essentially I got $50,000 for 5% of the company and that’s their standard term for almost everybody. It’s actually a really great deal because technically in an imaginary world this values a company at one million dollars which still blows my mind. [Laughs] So I have – they especially own 5 percent of WeddingLovely and at that point having WeddingLovely Incorporated which is a whole other business and get lawyers and all that sort of stuff and in terms of getting a return on investment that is hoping they get a return. We actually went through an almost acquisition with Etsy a while ago. So that would have been really good for wedding – that’s pretty much when they get the return on investment is if you get an acquisition which is a lot more likely than the other alternative which is an IPO. So they kind of hope for those events for a company to get big enough and most importantly enough it gets acquired or IPOs and then they get their money back hopefully with two, three, ten whatever times their original investment which is one reason why 500 Startups has such a rigorous application process because they are trying to – you know they are not going to invest with anybody. They are going to invest that money with people they really think is going to succeed.

Emily: Now when it came to the process of getting the investment like did you actually have to talk to them about financial things or were you able to just keep your focus on what your area of expertise is?

Tracy: Thankfully, I guess that I got lawyers and I got an introduction to my lawyers which is Gunderson, in the Bay area through 500 Startups. Once I started working with Gunderson, they were able to take over most of the process because they are actually 500 Startups lawyers as well and I had to sign some things and say, that’s okay they are not going to you know – it’s not going to be in conflict. That meant that they could set up most of the paper work for me and so I would just get emails from them saying okay, now is the time you need sign this papers for incorporation, all these papers for the investment and they usually run down the details with me which is really great and then mine was a little bit more complicated and again they took care of most of this which was awesome because oddly, WeddingType, the previous company was an LLC and then I was going to be billing WeddingLovely Incorporated which is a C Corp and so instead of just transferring one to another, because WeddingType was an LLC in California and then WeddingLovely is going to be a corporation in Delaware, oddly, they set it up so WeddingLovely corporation bought out WeddingType LLC. So I had to sign all this papers for like a merger and all these kind of things and then WeddingType LLC had to be officially like closed down as a company and then WeddingLovely is the one that existed at the end. So at one point I had two companies and one bought out the company, which was very strange.

Emily: You mentioned Delaware I’m curious were you formed as S Corp in Delaware because of the tax benefits that Delaware offers or it just happened to be Delaware?

Tracy: It’s actually C Corp in Delaware and this is again another place where I’m very happy to have lawyers because I know there is a reason why you incorporate in Delaware and it has to do with taxes or it has to do also with the Delaware is set up. [Laughs] All I know is that it’s advantageous to be in Delaware and that’s where they recommend everyone to incorporate at and so I was like okay sounds good to me.

Lea: Interesting. In regards to like getting funding etcetera now that you have the knowledge that you have would you have done anything differently in regards to getting money? Because there seems to be this movement towards bootstrapping versus getting funding versus whatever and there is certain amounts of freedom by just using your own money and you did save up you own money, but would you have tried to get money now that you know what you have?

Tracy: Most people usually just like due solely bootstrapping or they do solely raising money so after they get like the initial investment then they go and raise the seed and they go raise Series A. Well I kind of did a little bit of both. I raised that initial $50,000 dollars from 500 Startups and all indications were pushing me into doing a Series A and etcetera. But I decided to stop and bootstrap instead and there is a couple of reasons I did that and I wouldn’t change anything because I thought 50K was actually very helpful and I’m very happy that 500 Startups has been okay with me not raising more money because its allowed me again control, [laughs] it seems to be a theme here. When I don’t have investors who are kind of like really looking for an internal investment, they are very involved which would happen if say I raise a Series A because they would get more involved and then you’d have a board of directors and people owning more and more parts of the company and they can tell you what to do.

And with the wedding stuff especially let’s say for example when it comes to pulling in vendors my vendor directory is we do not create accounts for people without them explicitly doing so. So I would say there is a couple of other vendor directories out there that would like create a listing for someone automatically and then they can say – they find a listing and there will be a big button saying hey, sign up here and you can claim this listing. That’s a way you can like make it look like you have thousands to hundreds of thousands profiles and websites without actually – vendors actually signing up for anything. And so that sounds really great because then you say oh I have 10,000 vendors.

So it’s very important for me though to have these vendors actually apply on their profile on the website because then I can sort of contact with this people and then I can start working with them towards a paid account or to help them build their company and what not. And I also wanted to make sure that I wasn’t going to be initially pissing them off because it was [laugh] like you know they are like why does this website have my company on it already. But I kept talking to people like why don’t you do this you’d have so many vendors. You would like have so much more – like better metrics for your company. But it felt so slimy and I had to make sure that I can do those kind of decisions without having to like argue with someone about it. And then WeddingLovely at the point already started making money and I was kind of like okay maybe this is actually possible. I kind of grow this company using the money from WeddingLovely and not have to take on investment.

So the downside to that is that WeddingLovely is growing slower than probably would if I had a million dollar investment because you know if I had a million dollars I can hire you know three developers and two marketers and a bunch of designers and what not and theoretically create this like giant company that can be doing really awesome things and potentially growing faster. But by not raising money I’m able to grow it in the direction I want to. It’s still growing day after day and I can continue growing the company in a less slimy way then I’d feel like some…

Lea: [Laughs] An ethical way. Speaking of growth and revenue are you willing to disclose what kind of revenue you’re making?

Tracy: Yeah I mean I make between $2,000 and $5,000 dollars per month depending on what’s going on and I several different sources which is really great. Yeah I work with wedding vendors they sign up for a free account and they have the option of doing a paid account so a lot of revenue is coming from this vendors who are on paid accounts, weddinglovely.com that planning app I mentioned is also a paid product. People who are weddinglovely.com are planning a wedding with us that’s another source of revenue. I don’t want to put advertisements on these vendors’ pages I work with or on the planning app I think that’s a little bit unethical.

And the third source of wedding revenue is our wedding blog. So we actually run advertisements on wedding blogs kind of like cyber ads and sponsors post and it’s our only place we do advertising in WeddingLovely. So not on our vendor directories no on our wedding planning app, but that’s our third source of revenue and that’s kind of where the revenue ups and downs come from depending on how much advertising we sold that month.

Timestamp: [00:40:00]

Emily: So how long did it get to that point where you had some sort of regular source of revenue and profit?

Tracy: Profit definitely, because it all depends [laughs] I don’t think so.

Emily: Sure.

Tracy: Yeah it depends on how much I decide to pay myself, which again is still very little. My current salary is $25,000 dollars a year which is a little bit fun to live on sometimes. But in terms of revenue how long – I mean it kind of has just been growing slowly. The biggest jumps like I said one of our own sources of revenue is our wedding planning app. So when that launched that was a jump in terms of revenue which was really awesome, but in terms of vendors and in terms of the blog, those two sources of revenue it’s kind of been growing slowly overtime kind of corresponds with say how much page you use and how many vendors and how many people we work with which is nice because I can continue to trump that growth upwards in that its very stable so far.

Lea: So I’m curious then – you are talking about your growth, what are your plans for making it grow even further?

Tracy: I actually have a launch that’s going to be happening next Monday. So I wish I can announce it here. That’s going to be a few days after the podcast launch. So that’s going to be awesome, but I can’t say much so its checkout weddinglovely.com and you can see it if you are curious on Monday. I believe its November 4th.

In terms of growth one of my biggest goals is for vendors you want to see people’s reviews for wedding vendors and you want to see the previous people that they work with and what they say. There is a lot of websites out there that have new listings, but the reviews are all five starts because someone leaves a bad review that vendor complains, usually gets taken off the website and so you can only really see positive reviews and so one of my goals it’s something kind of a balancing act. One of my goals is launching a new review system for wedding vendors that’s going to be a little more balanced and again the balancing act is that I don’t want to make my vendors mad because sometimes you just have a very terrible client. A terrible client who doesn’t understand anything and starts complaining and it’s all actually their fault. That can happen, but I’m working on the system so you can kind of help start picking up some of these poor vendors that are out there. Whereas you can also showcase this really, really amazing vendors and have kind of – this review system hopefully will help people see both of those types of vendors and help them chose. So that’s one of the biggest things I’ve been working on in the backend that hasn’t launched yet, but are trying to build like this more honest and open review system for wedding vendors.

Emily: Do you have any plans for hiring? I mean you mentioned you had some part time people working on your third property the blog I think. Do you have any plans to – if you hit a certain benchmark in terms of profit to bring on a programmer or bring on someone who can focus exclusively on some other area of the business?

Tracy: Really I’d love to. When I had the 500 Startups money the 50K I hired someone full time so salaried, she is making twice as much as me which is good, knowing my tiny salary that’s not that much and money ran out very quickly when you have a salaried person all the time. So she had to be let go which was a really sad day for WeddingLovely because she is awesome, but couldn’t afford having a full time person at the time. So then I had to drop down to just me. The company actually went through this scary period where I had to layoff that person, it was horrible, the company was still kind of losing money and so we got kind of like this scary point where then finally the financial stabilizer started going upwards again. So for a while it was just me on this very tiny salary making sure the company didn’t go under and now it’s been growing enough where I can hire two part time people which is awesome and I’m hoping that it can continue growing where I can turn one of those part time people into a full time employ, start paying myself a little bit more of a reasonable salary. So yeah totally would love to hire, just have to wait to that point when I can do so.

Lea: With that I’m wondering what would you have done different when starting up you business to help set up for this type of movement and growth.

Tracy: I don’t know if I would do anything differently because everything I have done has been a lesson.

Lea: Yeah.

Tracy: I’m only at the point where I am right now because I’ve made say what could be called mistakes, but – so hiring that one person and getting the company to a really scary point in terms of finances because the company couldn’t support that person without raising money and then we didn’t lose money that was kind of scary. And it taught me a lot about money management though and now the company is got more even-keel and the bank has it going upwards rather than downwards. So I mean when I say that experience had gone away. If that experience wasn’t there would I really be really where I am right now. I don’t know. Everything I have done there has been – there really hasn’t been any really horrible disasters that I would take back and overall the whole process of working on WeddingLovely has been overall positive and so I don’t know if I would take anything back or do anything differently because I have learned so much from working on this.

Emily: So its sounds like your definition of success is very holistic it’s maybe not just about profit. So how do you gauge whether you are successful with WeddingLovely?

Tracy: As the only fulltime employee this would change if I had other people with me, but as the only full time employee its whether I am happy with what I’m working on and whether I am enjoying life right now because life is really short and biggest catalyst for me leaving that full time job I had is that while I was making money with it and it was kind of exciting it was also not what I wanted to work on fulltime and I actually really did not like my life at that moment. I actually almost moved to New Zealand to become a white water rafting instructor because I was just I’m done with the internet. You know I want to do something completely different. As long as I am enjoy what I’m doing and I’m happy with my life I consider myself successful. You know the company is till like I said it’s growing, it’s growing very slowly, but its growing. So I am very happy with that.

If I had a fulltime employee and I had other people working under me whose livelihoods depended on me then obviously that would change because then I’d be very focused on making sure I did not ruin their life accidentally by [laughs], it’s actually very real fear for me which was really having another person work with me because I was like I can’t just make sure that I am happy I have to make sure they are happy as well.

Lea: Sure.

Tracy: Right now it’s you know very selfishly kind of just whether I am happy with what I’m working on, whether I feel fulfilled and love what I’m doing which so far so good.

Lea: I mean you are in Prague, so hard to complain about that.

Tracy: [Laughs] As long as I have the internet which is the worst part about traveling while working and so sometimes we’ll – there was one point in Cologne where we got to our apartment and there was no internet and we were like well you said you had internet. They like, oh I ordered it, but we don’t have it. [Laughs] I have to company to work on.

Lea: Yeah that would be an issue I think.

Emily: Now Tracy do you have any resources you can recommend for anyone who is contemplating starting up a business or starting a startups?

Tracy: One of the best places for startup news and entrepreneurship is what’s called Hacker News and that’s run by Y Combinator so that is news.ycombinator.com and its basically a forum/message board where people can post interesting links now usually all are around startups or entrepreneurship or running a company or something like that and its very inspiring and there is lots of really great links that are on there. So I consider that kind of essential reading for anyone who is working on a startup or running a business.

Other than that, this might not be what you asked, but very important is to have a good support system. So you have family and friends and people you can talk to. I say that’s crucial for anyone starting a business and just make sure you have that first because it can be a very tough journey and just having kind of an offline life where you can escape to and people you can talk to and take care of you is very, very important.

Emily: That’s awesome that was actually going to be part of my final question which is what’s the final piece of advice but sounds like having a support system is really important when your venturing out on your own.

Tracy: Yeah partner/boyfriend, don’t know what to call him, he also does startups as well. So I have been able to watch him. He had his company sold at Google a few years ago and now he is working on a new thing right so it’s been very inspiring and having someone going through the exact same thing as I am right now. So that’s been crucial for me for feeling like I am not alone.

Lea: Fantastic! Man, there is just so much to talk about but that’s all the time we have for today. Thanks for joining us Tracy!

Tracy: Thank you so much for having me.

Emily: In case our listeners wanted to follow up with you where can they find you online?

Tracy: My personal website is at limedaring.com so that’s kind of where you can see the social media links and all that and that’s also my Twitter handle and then WeddingLovely… no missing consonance or vowels or anything like that just weddinglovely.com and that’s my company website.

Lea: Perfect. Now we’d like to thank our sponsors for this podcast Solspace and Pixel & Tonic.

Emily: We also want to thank our partners Arcustech, Devot:ee and EE Insider.

Lea: And thanks to our listeners for tuning in. If you want to know more about control click make sure you follow what’s on Twitter @ctrlclickcast or visit our website ctrlclickcast.com.

Emily: Don’t forget to tune in to our next episode when Jonathan Snook will join us to discuss modular CSS be sure to check out our schedule on our site ctrlclickcast.com/schedule for more upcoming topics.

Lea: This is Lea Alcantara.

Emily: And Emily Lewis.

Lea: Signing off for CTRL+CLICK CAST. See you next time.

Emily: Cheers.

Timestamp: 00:50:19

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Emily Lewis and Lea Alcantara

CTRL+CLICK CAST inspects the web for you!

Your hosts Emily Lewis and Lea Alcantara proudly feature diverse voices from the industry’s leaders and innovators. Our focused, topical discussions teach, inspire and waste no time getting to the heart of the matter.