I’m a big fan of partnering with others to create successful products and services. It’s what I’ve done in the majority of my successful businesses.
Of course, there’s a right way to approach collaboration, and a potentially disastrous way. And it’s almost maddening how much of a gut check it is when it comes down to it.
Today we’re chatting with Tracy Osborn – designer, developer, and the founder of WeddingLovely. She taught herself to code in order to launch WeddingLovely and runs all design, development, and marketing … but she originally thought she needed a co-founder.
Tune in to learn how to avoid making the wrong decision when it comes to partnering with others. Also, discover that learning to code may not be as difficult as you think.
The Show Notes
When Collaboration is the Wrong Choice for Startups
Tracy Osborn: Hi, my name is Tracy Osborn. I’m a designer, developer, author and entreprenerd. And I’m totally unemployable.
Voiceover: Welcome to Unemployable, the show for people who can get a job, they’re just not inclined to take one — and that’s putting it gently. In addition to this podcast, thousands of freelancers and entrepreneurs get actionable advice and other valuable resources from the weekly Unemployable email newsletter. Join us by registering for our Free Profit Pillars Course, or choose to sign up for the newsletter only at no charge. Simply head over to Unemployable.com, and take your business and lifestyle to the next level. That’s Unemployable.com.
Brian Clark: Hey there, Unemployable people, this is Brian Clark. Welcome to the show.
Today, we’re talking to Tracy Osborn. She is the entrepreneur behind WeddingLovely, which is a wedding planning app.
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Let’s get to our conversation with Tracy, because it is very interesting to hear her journey and how she ended up building WeddingLovely. But I think an interesting aspect of the conversation really has to do with one of my favorite topics, which is collaboration. However, in this case, we’re going to look at a scenario where it was best avoided.
So, let’s talk to Tracy.
Entreprenerd – I’m definitely stealing that.
Tracy Osborn: Yes, you may.
Brian Clark: Good, thank you. I need permission.
Tracy Osborn: The patent on it.
Brian Clark: Yeah, copyright, trademark and patented – “entreprenerd.
Tracy Osborn: Someone’s going to listen to this, and they’re ready to go, rush out and patent it or trademark it.
Brian Clark: But that’s exactly what an entreprenerd would do. So, how are you today? How is sunny California in the dead of winter?
Tracy Osborn: It’s glorious. I know, it looks so good right now, except it’s kind of cold out. And I say this as a Californian, which is ridiculous. Because anyone else from other places in the country that have snow is like, “60 degrees is not cold, but I’m really freezing in my house even though it looks so beautiful outside.
Brian Clark: And you’re moving to Toronto. I hate to tell you this, but…
Tracy Osborn: I know.
Brian Clark: It’s cold there, just a fair warning.
Tracy Osborn: The first time I ever went there, my then boyfriend, now husband, he’s helping me pack and he’s like, “No, more layers. And I’m like, “This is all I have. I have no more layers.
Brian Clark: More layers? That’s a very Colorado thing to say also.
How Did You Get Started?
Brian Clark: Well, you have such an interesting story, and I’d like to explore it a bit today. But I guess we should go back to the beginning. Not birth, but sometime after birth, where you got started in life in… I guess design really should be the starting point, right?
Tracy Osborn: Yeah, technically, I mean, I won’t go into it. But technically, I fell into trying to do programming first and I went to school for computer science. And long story short, I had a horrible time, so I switched over to an art degree and focused on graphic design. That’s what my degree is in.
Brian Clark: That is so interesting, because I do want to talk more about the programming thing. Because I saw your background. You have a major in fine arts, right?
Tracy Osborn: Yes.
Brian Clark: And I’m like, “Wow, this is amazing, because the old stereotype of the liberal arts major — we can’t do math (and that’s true for me), we can’t code, we can’t do anything. So, you actually did go to school for computer science and then shifted.
Tracy Osborn: I was like, “Hell, no, I hate this.
Did You Do Freelance Work Before Becoming an Entrepreneur?
Brian Clark: That’s such an interesting dynamic, because you hear all the time (Dan Pink is big on this) that it’s the creative liberal background, the well-diversified, you call yourself a jack of all trades, master of none. But that’s the type of person that can succeed.
And I think your story to a certain degree is a prime example of that, because you did shift into more of an artistic mode of expression. And yet, you ended up teaching yourself programming, which I think is fascinating.
Did you actually do any sort of freelance design work before you got into your more entrepreneurial ventures?
Tracy Osborn: Yes, I did. I’ve only had one job, and it was very much a startup. We started in a garage and I was the designer there. I worked with them for four and a half years before I decided to leave. And around this time, I met my now husband, and the summer I was trying to figure out what I wanted to do. So, I started doing some freelance on the side, because I knew I wanted to work for myself.
I freelanced. My husband was going through YCombinator and I had the opportunity to work with quite a few of the companies that were in his same accelerator batch. I worked with Reportive and a few others. And I will say it was fun. The Reportive site, which is still up even though Reportive was bought by LinkedIn, if you go to reportive.com, you can look in the source and it still says “Designed by Tracy Osborn.
It’s my claim to fame. It was fun working for myself and I really loved that experience. But working with clients was very frustrating as a designer, because I wanted to be…
Brian Clark: You’re the first person to ever say that.
Tracy Osborn: Yeah. It was just like they would say, “We want this. And I’d be like, “Oh, that’s a bad decision.
Brian Clark: “Make the logo bigger is the joke among designers.
Tracy Osborn: And I’d be like, “That’s not the right decision. I’d try to explain why, very professionally in terms they could understand. And like, “No, that’s what I want. And a little piece of my soul would dry up a little bit.
So, I decided that I really wanted to work for myself and by working myself, I wanted to make myself the boss, instead of having someone else telling me what to do.
How Did Your Business Get Started?
Brian Clark: So, at some point, and you keep referring to boyfriend/husband, which makes me think that it’s a recent development. But one of your actual claims of fame other than source code mentions is WeddingLovely, which is a wedding planning service that’s completely online, right?
Tracy Osborn: Yeah. So, I keep mentioning Andre, that’s my husband. I watched him go through YCombinator, and again, worked with those YCombinator companies. And startups, they looked so much fun.
So, I went through this whole process of trying to find a cofounder for this idea, for this wedding website I wanted to work on and got onto Hacker News. I had this whole post like, “I am a designer. I have this idea for a company. I need to find a cofounder.
I actually got a lot of people emailing me and I’m like, “Oh, I’m totally doing this right. I’m getting this cofounder. I’m working for myself. And eventually, partnered with someone, we got an interview at YCombinator and everything just completely fell apart the morning of our interview.
So, we didn’t get in and…
Why Did Working with a Cofounder Fall Apart?
Brian Clark: Okay, wait, wait, that’s too good to just gloss over. How does it just fall apart?
Tracy Osborn: Cofounders are so hard, because they can make or break a business. I thought I was doing it correctly this first step into running my own business by doing this whole interview process with all these people I don’t know. Because I didn’t have anyone close to me that I could partner with. So, I was like, “Oh I have to find a person to partner with.
So I went out, I had phone meetings with a whole bunch of people and then I knocked them down to some coffee meetings with a whole bunch of people. Knocked it down to working on the small projects with a few people, and then found one person I thought I totally jived with and we decided to partner up and start building this thing. And we applied for YCombinator, but we were working remotely and he was in San Francisco and I was in South San Jose.
We didn’t have experience with each other before working together. And we got this interview without having a product, like any kind of MVP, any kind of a minimum viable product out. And that morning, I think it was our first real type of really, really working together especially in this high stress environment of having this very important interview that afternoon.
This is six and a half years ago, so I can’t remember exactly, but it was just very obvious, I think, that morning that we actually did not want to work together.
Brian Clark: It’s better to find out at the beginning than later.
Tracy Osborn: Yes, exactly.
I remember sitting in the coffee shop after the interview, he had already left, and I sat there thinking to myself, “Oh man, if we get into YCombinator, there’s going to be a problem, because I already know I don’t want to work with this person. I don’t think we could work well together. But thank goodness, we didn’t get into YCombinator.
Brian Clark: I’ve never heard anyone say that before. “Thank goodness I was not accepted in that thing. But sometimes it can be a blessing. Things work out the way they do.
What Inspired You to Create WeddingLovely?
Brian Clark: So, let’s back up a little bit. What inspired you to come up with WeddingLovely in the first place?
Tracy Osborn: Well, this first website I was working with this person had to do with my background in design. It was going to be a Web app that helps people to design their wedding invitations. And I am not actually a weddings person, which might sound really weird, because I work on a wedding startup. But I am a design person and wedding invitations are the one kind of design that’s always going to stay in physical format.
There are a lot of online wedding invitation companies that you can send via email. But really, because it’s such an important event, there are always going to be paper invitations being sent through the mail. And I love paper invitation design. I think it’s gorgeous.
So, I wanted to help people originally design their own invitations if they didn’t have any kind of design skills. That’s really hard to do though, because there’s going to have to be this PDF generation crazy typography that has to be all done perfectly in the back end.
And when I switched my idea, which I haven’t gotten to yet, but yeah, little hint. When I switched my idea, I had to do something easier, but I still wanted to work in some way, shape or form with these invitation designers in this field that I’ve already started exploring.
Brian Clark: Yeah, it’s almost like, this is probably a bad analogy, but CafePress for wedding invitations. You’re taking digital inspiration but making it real somehow.
Tracy Osborn: Yeah, and minted.com is a good idea and something I was really interested in building myself. They’re doing a good job on that with the ability to do this design work in the browser with that company.
But when I switched my idea (and I’ll get into that now), what happened after the interview is that the cofounder and I split up. I realized that the only way for me to move forward with really my own company, I couldn’t just go out and find a cofounder and have them build it. I’d have to build it myself.
And I had to look at the programming, like the fact that I hated programming and I had a horrible time in college. I had to get over that and I started teaching myself programming to build basically a directory to help people find wedding invitation designers.
So, instead of helping people build their own designs, I just decided to make an easier app, and this app would help people find designers near them.
Brian Clark: Right, connect with the right people. That’s an interesting leap to me. And it sounds like something I would do. But you’re like, “Okay, this cofounder’s not going to work. I’ve got to teach myself to code, even though I hated it in college.
Tracy Osborn: Well, I was like, “I’m not going to a job.
Why Did You Tackle Coding Yourself?
Brian Clark: No, but was outsourcing development not just something that was…I mean, was it an issue of economics or control or what were you thinking there?
Tracy Osborn: Funny, because I don’t think I ever even thought of that. I think once I realized that finding a cofounder was not the way to go, that I love learning — and again, I’m going to keep mentioning him, because he’s been such an influence in my life, my husband. He works in Python, he’s a startup person, he’s a programmer.
I think he was pretty crucial to helping me realize that I should learn how to program and just do it myself. Because he was like, “Well, you’re learning Java in school and Java is a lot harder to learn than Python, so maybe try Python, maybe try doing this yourself.
So, I listened to him and he helped me figure out the essentials of Python. And I’m using a Django framework with WeddingLovely and the sites that WeddingLovely runs.
I think he was pretty crucial in making me realize I could indeed learn how to program and not be scared away anymore.
Brian Clark: That’s very cool actually. I think that from a personal development standpoint, that was an awesome choice. But from an entrepreneurial standpoint, I had to partner and/or hire people because I cannot code. I mean, I can help with features and I can help with usability, but I can’t do the code.
Tracy Osborn: Yeah, but coding is a lot easier now.
Brian Clark: Yeah, it’s true.
Tracy Osborn: We haven’t chatted about it yet, but the book series about teaching people how to code…
Brian Clark: Yeah, I was about to say also that worked out for you in multiple ways, learning how to do code. We’re going to talk about that in just a second.
What Made an Incubator So Important to You?
Brian Clark: I want to talk about one more thing before we do, which is 500 Startup. And that’s a colorful character named Dave McClure, right?
Tracy Osborn: Oh, yeah.
Brian Clark: So, you had this experience with YCombinator. It didn’t really work out, but you still wanted to go back to the incubator thing.
This is interesting to me, because I’m in Boulder and Techstars started here and it’s a huge thing here. But I don’t think that would ever be attractive to me. Again, I’m a self-professed weirdo in many ways, so I wouldn’t take that as anything.
What about that do you think was important to you?
Tracy Osborn: I kind of fell into 500 Startups. It wasn’t a big goal of mine. I will say that YCombinator, just because of who they are, I did apply for them before 500 Startups, didn’t get an interview. A lot had to do, I think, because I was a solo founder.
With 500, that summer, I started WeddingLovely or the site that started WeddingLovely, which was weddinginvitelove.com in January. And a product design blogger, Swiss-Miss, she posted her website. It started taking off, I started building it.
I heard about this organization in San Francisco called the Designer Fund. It’s all about helping designer founders. And I was like, “Oh, that sounds perfect. I want to be a part of this organization that’s dedicated to designer founders.
I spent that summer essentially stalking one of the people who runs Designer Founders. Nowadays, a lot of people aren’t using Foursquare anymore, but I think at the time, this was like the heyday of Foursquare. And on Facebook, he’d be posting his Foursquare check-ins or events he’d be at around the Bay Area.
So then, I just started showing up to all these events. I’d be like, “Hey, I’m Tracy Osborn, have I told you about this website I have? And then later on, I’d show up with another friend that was a mutual friend of ours. That person would be like, “Hey, have you met Tracy? And he’d be like, “Yeah, I met her at this other event.
I essentially just followed this person at Designer Founders around really doing the hustle, because I really wanted to be a part of this organization that’s helping designer founders. And I did get in, thank goodness, and it was a really great experience.
Excuse me, I called it Designer Founders. I had the wrong name. That’s a different organization. It’s Designer Fund, excuse me. And Designer Fund, it’s Enrique, he’s the founder and he used to be a part of 500 Startups. So, when I got into Designer Fund, he got me an interview with Dave McClure and I was like, “Whoa, that sounds like fun. Let’s do it.
Brian Clark: Cool. So, how did that go? And how was that different than the YCombinator thing?
Tracy Osborn: Yeah, it’s totally different. I know they have an application process now, but at the time, it was just invite or an insider in 500 Startups has to get you an interview. So, that’s how I got with Enrique.
The funny thing is when I mentioned before about my whole cofounder search, I wrote a blog post that said I’m looking for a cofounder and got onto Hacker News. And then I kept doing that, I kept writing. Another post I did that got really big was I wrote about the experience of learning how to program and starting the site, titled “I’m a designer who learned how to program and in six weeks launched my website, something like that.
All these posts kept showing up on Hacker News, and was really great for my career to constantly have basically these little advertisements about me. And then people in the…
Brian Clark: Yeah, that content marketing thing may catch on.
Tracy Osborn: Yeah, exactly. The people would know me in the Bay Area as “the weddings person. I would go to events and I’d be like, “Oh, hi, I’m Tracy Osborn, I’m working on this thing called WeddingLovely. And like, “Oh, you’re the Hacker News weddings person.
Brian Clark: Oh, nice. There you go.
Tracy Osborn: Yeah, it worked out super well. I wish my articles now would go on Hacker News. I have not had as much success since then.
But at that interview with 500 Startups, one of the partners was Paul Seng, and I had an interview with him first. And he had seen those articles on Hacker News and he’s just like, “I love what you’re doing and you’re super persistent. He actually called me a cockroach, which I think is hilarious. And he said it’s because I will never ever die. Which was true. And he was like, “You’re in.
Then I had a meeting with David McClure, and he’s like, “Well, tell me about your thing. Okay, we’ll be in touch. I’m like, “Well, Paul’s already said I’m a part of 500 Startups, and it totally threw Dave off, because I think this was done without his knowledge. And he looked a little peeved. But eventually, they were like, “Okay, fine. You actually are in 500 Startups.
Brian Clark: That’s a great strategy. If someone told me that, “Well, I was told that I already worked for you. “Oh, well then, of course, yeah.
Tracy Osborn: I kind of just fell into it. Well, now, I’m here.
Brian Clark: That’s interesting. Okay, so let’s get back to you taught yourself these programming languages, and it is more doable than it has been. But still, it’s a learning curve.
Tracy Osborn: It is.
Brian Clark: And so you decided that you were going to teach people what you learned. Now, you went about this through the Kickstarter process and I want to start there because I find that very interesting. Was it because you wanted like an MVP process of its own? Is there a demand for this or were you really looking just for funding?
Tracy Osborn: A little bit of all of the above. The Kickstarter was kind of a no-brainer once I decided that I wanted to write a book. And I did get some publishing offers.
But as a designer, I was like, “Well, what’s a publisher going to give me? They’re going to do the design for me, which I could do myself. And I really like working for myself, so I might as well do it myself. And they’re not going to give it much else other than a very tiny royalty.
So, I decided to work really work for myself. I decided to self-publish, and Kickstarter was a way to get preorders and get people to know about the books that I was writing, start getting the word out there. But also a way for me to get funding, because as a designer, I really wanted to have a physical book.
I could make so much more money or at least, I’d have a lot less expenses if I did not do a physical book. And I kind of, I don’t know, shake my fist sometimes about how much it costs to print and ship all these physical books. But having a physical book is so awesome and it’s so great to be able to bring to events, and just so awesome to take to people and show off the design that I did.
So, when I had to do a physical book, I had to pay about $5,000 to get them printed and I had to that before the book was even out. So, I needed that funding from Kickstarter to afford that.
Brian Clark: Yeah, it makes a lot of sense. I mean, you give away everything including your soul, in my opinion, when you go with a traditional publisher. But they take care of that expense stuff if you’re lucky, and it’s hard to get an advance anymore. But yeah, I’m a big fan of selling stuff that doesn’t exist yet. I’ve done that myself.
But, yeah, Kickstarter is amazing. It does test the demand. But it seems to me that for this particular project, I think you knew you had a winner there.
Tracy Osborn: I was pretty sure, because I mean, even though it’s a niche, because the book Hello Web App is teaching Web development using Python Django. So, exact stuff I used to build WeddingLovely.
I knew I wanted to write it, because over the five or so years of working on WeddingLovely, I’d figured out a lot of tricks and whatnot about Python and Django. And I kept thinking to myself, “The process of me learning to code was really frustrating, because everything was written for other developers. I really wished there was a book, like what I eventually wrote. “I wish that existed when I was learning how to code.
So I was like, “Okay, well, at least I know this doesn’t exist and I know that I can teach you it in a way that I think would be a lot easier for people like me. Since then, it’s done really well. So, yay, my assumptions were correct.
Brian Clark: Yeah. I just want to point out one important thing, what you just said: “The thing I wish I would have had is the beginning of so many smart product development choices, right?
Tracy Osborn: Yes. It makes life so much easier when your customer is yourself.
Brian Clark: Yeah, I’m a big advocate for that, and yet, people are like, “What do I know? Well, you know lots of things. You have preferences as a consumer. All you have to do is shift your hat to producer and figure out a way to get it done. And I think that’s exactly what you did. I did go check out the original Kickstarter, and it made so much sense the way that you positioned it.
Something else that I wanted to point out is so many designers turn out to be great founders. I mean, that’s becoming more and more. And, personally over the last decade, my right-hand person has always been a designer, because I can’t do anything without him. If I were one, I guess I would be perfect. But no, I’m just kidding. There’s a little humor there.
Tracy Osborn: Only so many hours in a day.
Brian Clark: Yeah, exactly. You’ve almost convinced me to learn how to code. I can’t learn design as well. I’m one of those people that I spot good design, but I’m not sure I could do it. I’m not sure what the distinction is there. And you could probably give me your thoughts on that.
Tracy Osborn: Oh, one thing I want to mention about Kickstarter, the other thing about Kickstarter is that it’s the easy way, or at least the nicer way, of asking your friends for money.
Brian Clark: Exactly right. “This is official. This is not me just sticking out my hand.
Tracy Osborn: Yeah, exactly. It’s harder if I said, “I’m building this book, and I went to all the people who had eventually — all my friends and people in the programming community — and said, “Hey, I did this book, can you give me money? It’s a lot harder than when there’s Kickstarter.
I will say that the Python community — I know there’s a lot of really great communities out there, and I’ll say that Python is one of my favorite communities. The people who work in Python and opensource and people who are on the teams that really help aid Django, which is the framework and the growth for that, they are so incredibly supportive.
When I announced I wanted to work on this book and support Python and Django development and bring more beginners in, so many people who weren’t interested in the book for themselves, but just wanted to support me, were able to do so through Kickstarter.
Brian Clark: Yeah, that’s an excellent point. I always say you have to be a member of the tribe that you want to be a leader of first. So, you find that support within the community, because you’re doing something good for the whole, even though it’s also good for you.
Tracy Osborn: Yeah, and I did tie my Kickstarter for PyCon, the big Python conference. And I was able to run around to all the big wigs that are in the Python community in person, and be like, “Hey, I have a Kickstarter. You should help me out here. People I didn’t even know I was able to talk to in person and get them to help me with the Kickstarter. But they also were able to share it on their social media and share it with their friends. And I was able to get on stage and tell people about it. So, I did aim that Kickstarter as well to help me out with marketing to the Python community.
Can Anyone Learn to Code if They’re Willing to Work?
Brian Clark: Smart. All right, so Hello Web App, we’re going to link this up in the show notes. If you think you can’t code, you’re probably wrong. You do have to do some learning. But it is doable. And the more and more I’m having these talks with designers who became coders, it seems like a natural progression, html beginning point.
But I don’t think that’s necessary. I mean, is that your opinion? That basically, if someone’s willing to commit to learn, they can do that?
Tracy Osborn: Yeah, I’m so happy that things like Django exist, these frameworks, because it takes a lot of the hardest parts of programming and just kind of hides it behind a curtain.
All you have to do as a beginner is to figure out how to interact with these pieces that are all built for you. It’s a lot easier now to build a Web app that you can have a login system, you can have a database and you can have all this dynamic data coming in. But you don’t have to do the crazy hard programming things you would have had to do, say four or so years ago.
Brian Clark: Excellent. So, back to this full circle move, to the frigid climate of Toronto.
Tracy Osborn: It’s frigid and humid. That’s the two things that I don’t want to deal with. I mean, not at the same time, but the winter is going to be frigid. The summer is going to be humid. My husband’s going to kill me when he hears this, because I told him how much I want to go to Toronto, but I do spend a lot of time complaining about the weather, because I love my California.
Brian Clark: Well, best wishes. And happy husband, that goes a long way.
Thank you so much for being here. I think you have a remarkable story. I think you have remarkable tenacity, and you dodged a bullet with that cofounder.
Tracy Osborn: Yes, I know. Cofounder. It is a thread with my husband, with my friends doing startups, myself. Cofounders can make or break your business. And if you can’t find a cofounder, why not just learn how to program and do it yourself?
Brian Clark: That’s why they call them solopreneurs, people.
Tracy Osborn: Aha, entreprenerds.
Brian Clark: Entreprenerds, that’s right, I forgot. I’m stealing that.
Okay, Everyone, thank you for tuning in. We will have more for you next week. Until then, keep going.