Tracy Osborn Founder of Wedding Lovely

Episode № 16

Tracy and I talk about her experience building and running Wedding Lovely, raising some funding for it, losing a co-founder, and even going through a heart-breaking acquisition process with Etsy. Through it all, she's kept going and even published books to help others build their own web applications. She's a brilliant example of someone that simply won't give up, and while there's no IPO looming, she's making a great living doing what she loves with a small team.

Garrett Dimon: Hello. We’re here today with Tracy of Wedding Lovely and Hello Web App. I’ll let her talk about Wedding Lovely a little bit. Hello Web App is a book to help you do the development side of launching an app and doing some of the logistical things in there. Hello, Tracy. Welcome.

Tracy Osborn: Hi. Yeah, thanks for having me.

Garrett: Of course. I guess the way to start out would be, give me a little background on your career trajectory and arc. What led to Wedding Lovely and then kind of talk a little bit about what Wedding Lovely is. And then we’ll dive into all the really really fun stuff.

Tracy: Okay, cool. I have an art degree. So, I went through school for graphic design. I touched a little bit into computer science, so I was like ugh. And so I went to art and I thought that I wasn’t going to touch the programming side of things. Then I kind of gradually fell back into programming because after school I started work at a startup that was doing SEO stuff, and worked with them for four and a half years starting from a garage into an office.

That was really cool to work at the small startup because it taught me a lot about teaching myself. There was only 13 people at this startup. And after four and a half years I was like “Well, I’ve learned a lot from working at this startup and from being with these people but I’m in the Bay Area. This was a startup. It’s kind of getting a little tiring after four and a half years. So, what if I started my own startup as you do when you’re living in Silicon Valley? Everyone and their mother has a startup.”

So then there was a summer of doing some freelancing and I played briefly with trying to find a co-founder. Because as I had an art degree, I didn’t know programming. I was like, “Oh, I need to go find my technical co-founder.” And that lasted about three months. I actually got a Y combinator interview with this person. But the day before that interview, things exploded and I was like, “Oh, this is why you don’t get co-founders from the internet. You actually aren’t compatible in that period of time.”

So, long story short at that point I decided to jump in to programming, taught myself Python, and I launched a directory of wedding invitation designers. So this is really how Wedding Lovely started, not because “oh, I’m interested in weddings” but it was like me as a graphic designer wanting to support other graphic designers. People who are working with wedding invitations and wanted to have a place. Something that was easy for me to program, which is a directory. Get, make a place for people to find graphic designers to help them design their wedding invitations. I thought that would be a cool niche. That’s where the whole wedding thing started.

And when this directory started taking off I was like, “Well, I could just clone that directory and make one for planners. And I can clone that directory and make one for photographers.” And that went for like… I did eight clones. These were not on their one-code base, which is looking back on it I was like, “Whoa, that was really terrible.” Because when adding something new something new I’d copy and paste it between each of these project clones.

So this was, Wedding Lovely has been eight years ago so this is early times. Now those clones have merged into one general vendor directory. Those individual websites still exist, Weddinginvitelove.com is still a place where people can find wedding invitation designers. There’s also one site that combines everything into one big vendor directory.

And on the other side of the business now is there’s a wedding planning app that I built to help shuttle people. Help them plan their wedding in a more sustainable fashion. I wanted to have a place where I’m like “Hey ignore all the traditions and all this BS really that’s in the wedding industry. Use my planning app.” I’m trying to be very real, and down to earth, and friendly with it. And then also help support the small businesses that we work with since they are included in the app as well. That’s kind of this monster.

I actually got a Y combinator interview with this person. But the day before that interview, things exploded…

Garrett: No, that’s awesome and I love the progression on development. And I think one of the things that I love hearing is… So, with programming there’s so much people want to put people down, you see all that and it’s like you don’t want go to Stack Overflow or ask questions. But to me, I love how naïve we all are when we’re getting started. And it’s like “Oh, I can just do this.” And, more often than not, if you just start and kind of do it, things take shape. Even if it’s painful and messy and wrong, eventually you figure it out. But if you know too much, you’re like “Oh I could never pull this off.” Whereas if you don’t know as much and you’re learning as you go, you kind of have the courage to be like “Eh, what the heck.”

Tracy: Yeah. Definitely.

I taught myself a lot of code while building this. Every time I had to add a new feature, I’d be like “Aw crap, I’ve got to figure out how to code that feature.” So then I would go and figure that out and be like “Oh wow”. And then I’d pick up what I learned and look at my old code and be like “oh crap”. And then I’d go fix that. And it’s just been these iterative process.

There’s still things in there that are terrible, but it works. So when I try to teach people how to code through Hello Web app, sometimes at workshops I’ll actually show the code base for Wedding Lovely. Because even to people who don’t program, they can look at it and they can see things that aren’t-

Garrett: Yeah.

Tracy: You know, that’s, things are being repeated, things are super wordy. They can see that it’s awful, but I’m like “Hey.” And yeah, I’ve been running this for eight years. So you can code something and it won’t look beautiful, but if it works, that’s all you really need to do. That’s the only thing you need to do in order to launch something and start working on it. To see if it works.

Garrett: Well, there’s never really time to improve it, which you have with most of these apps. An eternity of, if there was time, there was always time. And so every now and then, if I needed a break I’d circle back and fix something that I hated. And you know it kind of slows you down. But in a way that feels better and it’s reassuring. It’s like “All right, I cleaned that up.” And then it enables new, better features down the road and that kind of thing. So it’s, sometimes it’s okay to get a little sloppy I guess in the beginning. I think the biggest challenge is just when you’re getting sloppy and you don’t realize it’s sloppy.

But it’s another thing when you know what you’re getting yourself into, and you go “You know what, I’ll make this straight off now, and I’ll circle back when I’m, when I need to.”

Tracy: Yeah. One thing that helped is that I had friends that were, knew about security issues. So I was like “Okay, I know my code’s horrible, but just make sure I’m not introducing some vulnerability.” And there were a few really stupid things back in the beginning of the app, and my friends were like “Oh hey, you need to change that. Otherwise people can delete other people’s objects willy nilly.”

And I’m like “Oh, learning experience.” So as long as I got, having people I can be like “Hey I don’t know anything. Just please check it for security issues.” That was really helpful.

Garrett: And I would say that’s probably the biggest thing, I think, getting started. Is not being aware of that kind of stuff. And that’s hard. Because there are people that dedicate their whole careers to doing that and know the ins and outs, andthat’s certainly a challenge. So yeah.

Tracy: Yeah.

Garrett: The thing, so it’s not traditional SaaS.

Tracy: No.

Garrett: You’re not charging subscriptions. But it’s providing a healthy income, and you mentioned that it started out as being paid originally.

Tracy: Yeah.

Garrett: And you’ve drifted away from that. Can you talk about that?

So when I talked to customers about why they would cancel or talk to people why they didn’t show up, this was constantly that thing I had running up against. Was you know, I can just spend more time by using free resources. So why would I pay for your app?

Tracy: Yeah. So the way Wedding Lovely makes money, couple different buckets. The primary way is by selling premium accounts to the small businesses that are all on Wedding Lovely. So they can opt in. I call it the Certified Lovely Vendor program. So it sounds all lovely and sparkly. And it’s essentially a review process, where me and my people I work with review people’s applications, give them a stamp of approval, and then they float to the top of the search results and all that. So that’s how we make the majority of the money. There’s also affiliate links through our blog and sponsor posts and whatnot through our blog.

And then I always wanted to monetize every part of the process. As you naturally do. Get revenue coming in from multiple services. So when the planning app started, it was like no brainer. Going to charge for this wedding planning app that we launched. And I believe the pricing was eight dollars per month, or a 70 or maybe 80, 79 dollar flat fee. And it was a pay product for about a year, and it was a very interesting period of time. Also the app was a little bit different is that the app was help you plan your wedding and also build in a wedding website.

And the wedding website was actually the most popular feature for people planning their wedding, because they were using this planning guide, but they really wanted that wedding website. Which also blew my support requests through the roof. Because people have a wedding website and there was, they can change fonts, they can change colors. But then it’s like they’re emailing me saying “Oh, can I add sparkles. Oh, I want to have extra images on my homepage.” And then every single person wanted something completely custom. And I started doing that, and it just got overwhelming. Because at the time, this was just me working on it. I think I had maybe a couple people, part-timers. But I was the only full time person.

And the other part about the planning app is that people were… You’re in the wedding industry. There is so much free information out there. Because wedding blogs are such a huge thing, and wedding magazines are so big. And you’re competing with people who’ve kind of become brand names in weddings. And you’re trying to attract people who are just planning their wedding. And first thing you do is you start searching for wedding blogs. You go to these big brand names and they have their own free advice. And if I got people onto Wedding Lovely, and I said “Hey, this is everything you need to track and plan your wedding, has all this great advice, your life will be simpler. But, it’s eight dollars a month.” People will, spending you know 35,000 dollars on their wedding, were like “Why would I pay eight dollars a month for your thing when I could just be looking at this free advice out there?”

The thing with weddings is that people aren’t looking to save time. A lot of people want to jump into weddings and build an app, because they’re like “Oh my God, I’m going to save someone so much time with my planning app.” People don’t want to save time. They want to have this reassurance that they’re planning the wedding the best way possible. They enjoy that time spent on planning their wedding. And if it takes more time to go out and read all these free articles, these really good free articles, and free advice, and free planners out there, why would they pay for an app?

So when I talked to customers about why they would cancel or talk to people why they didn’t show up, this was constantly that thing I had running up against. Was you know, I can just spend more time by using free resources. So why would I pay for your app?

Garrett: Yeah. So it’s a combination of every market, every audience and their needs. They aren’t always rational or predictable. And especially with consumers. It’s just difficult. Even though they’re in a mindset of spending money, it’s not, this isn’t money that’s going to show up at their wedding.

Tracy: Yeah. And you know, there’s a psychological thing where when you say “I’m going to save money by not spending money on that app.” But they’re still spending 10,000 dollars on a venue. But hey, at least they saved money in another place. You have to get over that urge to try to save money in these small areas. Because it makes them feel better overall.

Garrett: So you talked about support a little bit. How much time at that point were you spending on support versus… I guess it sounds like that’s probably not a feature you’re offering anymore and it’s not…

Tracy: Oh yeah.

Garrett: So how has that changed support and the time and the investment you have to spend on that front?

So the support requests for the brides and grooms were kind of driving me up a wall. And spending a lot of time. So I made a decision that I valued these businesses. I thought these businesses would be better for me to work on long term.

Tracy: Yeah. So the app was making money and people were using the wedding website, and I was getting a lot of people saying how much they loved my wedding website feature I built into there. But that support was just murdering me. And before, with my customers being businesses… I don’t want to go into cliches about the whole bride and groom people being bitchy, versus businesses. But really, they’re harder customer to please and talk to. Because the process of planning a wedding is very stressful. And in talking to small businesses, support requests were way better. Because small businesses are naturally a little more understanding when I’m like “Hey, things screwed up and I did this.” And people are like “Ah, yeah, that’s totally fine.” It gives a different dialogue between businesses. It’s a lot more friendly, I like it a lot more. Saves my mental mentality.

So the support requests for the brides and grooms were kind of driving me up a wall. And spending a lot of time. So I made a decision that I valued these businesses. I thought these businesses would be better for me to work on long term. You know, if I was a VC, I have VC money, but I didn’t end up raising anything more. So it was moved back to bootstrapping. If I had a 32 person team under me, I could totally handle support requests and build the product that people want me to build. But if there’s going to be just me and maybe a couple part-time people under me, then I needed to put the business in a sustainable place. Which was working in businesses only, and cut out these support requests. So I ended up by making the planning app free, I would also maximize the amount of people using the planning app, and then moving on to working with businesses I work with. So I give a better value to those businesses. So I ended up ripping out the wedding website, and it was hard to code this again. Which was like, all the people after this date get access to these features. And all these people after this date, all these features have to disappear. But I set it up so the wedding website part didn’t exist anymore. I did a partnership with another wedding website company, saying “Okay, hey. You get a discount on wedding websites with this company, but we’re not offering this anymore. Previous people will be supported.” Made the app free, and decided to just cut off that chunk of revenue. But overall, it made my life so much simpler. And long term, people don’t even remember that it was paid anymore.

Garrett: Well in hindsight, I’m sure looking back on that it’s oh such an obvious, easy decision.

Tracy: Yeah.

Garrett: I’m guessing it probably wasn’t as easy of a decision in the moment to make such a shift like that. I mean, did you debate that for a while, or does it just kind of…?

Tracy: Honestly, I think I just kind of rage quit? So it wasn’t that hard of a question. It was just kind of, things were building up for a while. Also, when I was building the planning app, I was trying to fundraise. And so having this stars and rosy view of “Oh, we’re going to make so much money on this planning app. And here’s where it could evolve.” I pushed it really hard, and then we didn’t raise, so then I went back to that bootstrapping model. And then it was just like “I am done with this.” And I think this was like a period, there’s been periods of time working on this. Because over eight years where I’ve gotten very frustrated. And I think that was a period where I was just like “You know what? Flipping the table. Changing the way this was working.” Going back to the small business part of the company largely runs itself. So, maybe around this time is also when I started working on the Hello Web app. I don’t quite remember when that came in. But the books came about the time of my life I needed to have something else positive to focus on. Because I was getting really frustrated by the way that Wedding Lovely was going.

Garrett: So in terms of hours a day, what would you say it was before versus now on support?

Tracy: Oh interesting. I hesitate to say this, because it’s probably not going to sound like that much. It was probably only three hours of emails in the morning.

Garrett: That’s a lot.

Tracy: But when I have to do it. Yeah, yeah. Marketing and sales, and also design and development, it was just kind of like “This is ridiculous. I don’t enjoy this.”

Garrett: Yeah. Okay. And so, but that was before or that’s current?

Tracy: The support, that was before, yeah.

Garrett: Okay.

…one of the best decisions I ever made for running Wedding Lovely is I hired a virtual assistant

Tracy: Well I mean now is kind of weird. Because one of the best decisions I ever made for running Wedding Lovely is I hired a virtual assistant. Which just sounds so Tim-Feriss-Four-hour-work-week. But I actually hired a Philippines based virtual assistant who does support for the businesses that I work with now. And so I don’t touch support, which is like “Oh my gosh. So much better”. Life is so much easier. Because mostly support requests was just the same thing over and over. It’s like “Oh, what’s my password? How do I change my user name? I can’t figure out how to end an image.” And it was, even though I had canned responses for each one of these scenarios.

Garrett: Yeah. It’s a distraction.

Tracy: Yeah, just having someone else. I’m like “Here’s the canned responses, you deal with them.” I should have hired this virtual assistant five years ago. She’s been working for me full time for about a year. I’m paying her 500 dollars a month. As far as I can tell, she’s super happy by working with me. I love working with her. Oh my gosh. Hire a virtual assistant.

Garrett: Yeah. That’s something I regretted with Sifter. And it wasn’t so much the volume of support requests. For me I was always afraid, they’re moderately technical, right? And just developers and it was a struggle. Like “How am I going to find somebody who understands their context?” And so that was my fear, was I couldn’t just hire a virtual assistant. I had to hire somebody who knows development.

Tracy: Right.

Garrett: And it would be much more difficult. Because by the time you know and have that experience, the last thing you want to do is be a support person. But it can be such a distraction. Just the intermittent interruptions. So it’s definitely hard to juggle that.

Tracy: Yeah.

Garrett: And it takes away from the time that you should be spending.

Tracy: So what’s funny is that through the distractions, I have a new, I wouldn’t call it an issue. But I have my virtual assistant, I have another part-time person that’s been working with me for six years in Washington, and then I just hired a old part-time employee that had to leave because she needed full time and I couldn’t afford it. This was like two years ago. And then she messaged me in January being like “I want to come back, even if it’s part-time.” And I’m like “Well, we still can’t afford full time, but how about I just…” I’m actually not paying myself for Wedding Lovely right now. I took what I was paying myself, and I’m shelling to her. And she’s, because I’m in the middle of writing another book. And I was again going through that period of being burnt out. And I’m like “Here, you run the company and I’ll help you.”

So her and then my two other assistants are kind of running Wedding Lovely for me right now. But it still means throughout the day I get them pinging me being like “We don’t understand how to deal with this solution.” It’s getting better since January, but it’s still, now I’m struggling with internal company support. I’ve never had a team under me like this before. So I’ve been learning a lot about, “Oh wait, now I have to manage.” And not being paid for it. But that’s okay, because I love my little product and it’s surviving by doing this.

Garrett: As the companies evolve the problems don’t go away. They just change.

Tracy: Yeah.

Garrett: I think is all it is.

Tracy: And they’re kind of trying to, right now this last month has been trying to encourage my right-hand woman. I’m like “You can make more decisions on your own without asking me. I trust you.” And it’s just getting over that little hump.

Garrett: Yeah. It’s tough. It’s a transition. And I think it’s easy, I was scared of that transition. I was like “I don’t know. I don’t have time to hire somebody to help me.” And the thing is, you almost don’t have time not to. But it’s still a scary kind of, “How would it work?” But everybody I’ve talked to who’s done it has always said really really good things.

Tracy: Yeah. And it’s cool when I see the email thread between the three of them. There’s a problem and they start solving without me. And I’m like “Oh, it’s so awesome” I can spend more time on my book looking at this. And problems are being solved and I’m watching other people work on them. It’s actually this really cool feeling.

Garrett: Yeah. So then now, I guess now you’re kind of shifting away from it. How does your time break down now versus, or I guess really just before you did that and then now. How are you splitting up your time? Is it purely focused on the book, are you mixing in with other things, how’s it?

Tracy: Yeah. Every morning it’s always probably about an hour of working on emails. Usually through Wedding Lovely, and answering questions from my team. Writing is really hard for me, so like yesterday I got nothing done. I guess I got some things done, but I wish I could be like “Yeah, every day is two hours of emails and then six hours of straight writing.” But it’s kind of just walking in circles around my apartment not doing anything. Mostly, whenever there’s political news going on, I just can’t focus. And so today is probably going to be another bad day for me.

Garrett: Yeah.

Tracy: Regardless of that.

Garrett: That’s hard.

Tracy: Yeah. So, now I’m trying to spend most of my time. I’m trying to get this. One of the reasons why I’ve like “Okay, I need to stop focusing on Wedding Lovely.” Because it’s going fine on its own. Because I have this idea for this book, this design book. I’ve been talking it up for two years, and I just was not releasing it. I kept doing this conference talk, being like “Oh yeah, I have this book upcoming.” And people are like “That sounds awesome.” And then half a year later I still haven’t started working on it. So I’m trying to force myself to get a… The first draft is finished, I have an editor now, hopefully by summer it is out. And then I will probably move into supporting these books and helping sell them. But jumping back into Wedding Lovely, and continue working on it and design and develop it. Like right now, no major features are being worked on. But I have this gigantic list of things I want to build.

Garrett: Okay.

Tracy: So, probably when this book is out and I can focus on it, I’m going to jump back over. Probably not be paid for it, but that’s, I don’t know. I want to see it succeed. So I’ll just continue building on it.

Garrett: It’s funny that you talk about that and not getting paid. I mean, presumably if you were just doing it full time by yourself, you would be deriving a full time income. Safe to say.

Tracy: Yeah. This year. Since I fired myself, Wedding Lovely’s doing way better. I’ve never been, a full time salary I could get as a developer or even as a designer. I would never have gotten that in previous years.

Garrett: Yeah.

Tracy: A lot of the reasons why I thought a web app was good, because it brought in income. I also had the really lucky deal when I was in San Jose where… This sounds really lucky. There was a long story. But I had no rent in San Jose. So I was able to focus on building these things without having to worry about spending out 1500 a month on rent. I now live in Toronto. I have rent again. But I was lucky that I was able to work off a very low salary. To just futz on this and play with things and then get it going. Anyway, like now, I could actually make a good salary if I shoveled all the money to me. So I probably would pay myself a little bit. Make sure there was no profit at the end of the year. Play that game.

Garrett: Everybody glorifies, says “Oh you have your own business. You must be so successful.” So many of the businesses. The thing is, you’re just shuffling the money back into the business. To grow it. I don’t think I paid myself what could arguably consider market rate until about six years in.

And so, it’s one of those things where it’s like “Yeah, it’s neat. Theoretically I could pay myself more.” But you want to grow the business and invest in the business.

Tracy: And it’s also if you can pay yourself less and have freedom to mid-afternoon go to the market rather than being stuck at a desk.

I’d much rather work for myself at a much lower salary than have a full time job. I played with that last summer. I got a full time job. And four months after working at this job I was laid off because they had budget issues. But I was very happy to be laid off.

Garrett: Yeah.

Tracy: And I was like “Okay, full time job, and it’s nice and I had a great salary and that was awesome.” But when the day I got laid off, it was the happiest day. I was like “Cool, I don’t have to worry about that anymore.” I like working for myself. I like making my own hours. I like working on this app. I like seeing it grow and see people use it. Even if it’s not a runaway success. Anyone looking at Wedding Lovely, I’m sure could have a billion ideas. Like “Why aren’t you doing this? It would be so simple if you did something else.” You know, I have a really loosey goosey feel about it. And as long as I’m happy working on it, I’m not going to stress out too much about what I’m not doing or how much bigger it could be.

Garrett: Yeah. No, that’s huge. I think a lot of people too get carried away thinking that they’re going to launch something that’s going to take off and they’re just going to sit back and cash checks. But everybody I talk to, it is almost… Every now and then it happens like that. But even some of those stories, there was two years before they took off where it was really really painful. So.

Tracy: Yeah, you can’t count on it. Again, with Hello Web, I’ve been trying to teach people how to, my goal was to help people build web apps. Because I really enjoy the process of building this web app. And the actual process to get a launch was pretty simple. And I was like “Well, I might as well just write a book on this.” Because it was pretty simple and I can put it into a very tiny book. And at the end of the book, people will have a web app. They won’t know how to code, which is fine in my opinion, because like I said I learned how to code by building my app. So I figured if I can teach people how to build their own app, they can teach themselves to code by building something real. I think it’ll stick better. At least, it did for me.

But I also do a conference talk called Marketing for Developers, and one of the big things is you’ve got to do marketing. Because a lot of people are like “How do I go viral?” Or like “What will happen when people see my app?” And I’m like, “You’re not going to go viral. People aren’t going to see what you build.” Then there’s this whole other process of you can build a web app, but now what? How do you get people to see it?

Garrett: And as developers, none of us want to do the marketing.

Tracy: No.

Garrett: At all right? We just want to build the web app.

Tracy: Yeah. And just sit back and wait for the money to come in.

Garrett: Yeah. Marketing is definitely, I feel like that’s the one undervalued skill for designers even, too. Designers and developers.

Tracy: Mm-hmm (affirmative)

Because if you build something in weddings, you have to get customers. New customers. Whole new set of customers, pretty much year after year after year.

Garrett: Building… Everybody thinks “Oh, well if I just build a good product then I don’t have to market.” And I think it was, I don’t know if it was Steve Jobs or whoever, but it was marketing is the price you pay for, the tax you pay for developing or building a bad product.

Tracy: Oh yeah. That’s a good one, I should keep that.

Garrett: And so, but then everybody thinks “Oh, well if I just build a good product then I don’t have to market.” But it’s, I think it was Steve Jobs: “Marketing is the price you pay for building a bad product.” But then everybody thinks if they just build a good product they don’t have to market.

Tracy: I was having an argument yesterday with someone about how simple it would be to launch something in the wedding industry. And I was like “Well how are you going to get customers?” Because if you build something in weddings, you have to get customers. New customers. Whole new set of customers, pretty much year after year after year.

Which is what kills wedding apps. And he’s like “Well, it would be word of mouth. People who use my app are going to love it, and they’re going to tell people and it’s going to, I’m just going to grow from word of mouth.” I’m like, “No, you’re not.” People also in weddings, it’s like PTSD after a wedding is done.

Garrett: Right.

Tracy: No one wants to talk about how they did their wedding, what apps they used, and share that information with friends and family.

Garrett: They’re just done with it.

Tracy: Because they don’t want to think about it anymore. Word of mouth is not going to happen.

Garrett: So, moving on to some of the more challenging things. I’ve got a few questions along these lines. What’s been the toughest day that you’ve encountered with a business, and how did you get through. What was the day and how’d you get through it?

Tracy: So Wedding Lovely launched in 2010. 2011 I went through 500 Startup’s incubator program. So they offered to fund me, and I just I was doing a bootstrapped business and I was like, “You know what, I’m going to switch it over to a VC business.” So I went through 500 Startups, and then a very very awesome person was like, “I want to be your co-founder.” And I was like, “Boom. I am doing things right.” And then Etsy came to me offering to do the acquiring process. And I was just on top of the world. I just went through 500 Startups, I have a new amazing co-founder, going to Etsy, being flown to Etsy and staying in this really fancy hotel, and meeting all the heads of Etsy. And I got the offer from Etsy, and this is where things just started going downhill.

Because the offer from Etsy… All of my advisors doing this acquisition process. Of course I went to other people. Being like “You’ve been acquired. Please help me. Be my advisor.” And all the advisors were like “That is a shit offer. And there’s no way you should take it.” So I turned down Etsy’s offer, tried to negotiate, they were just like, “Nope. Bye.” And then my co-founder and I were like, “Let’s try to build this business.” But four months later, she sat down and was like, “No, I’m out. I have a new job, I’m starting tomorrow.” Which was really shitty. So that was like the lowest, absolutely lowest point. Where I screwed up this momentum after demo day by pursuing this acquisition. I didn’t fundraise immediately after demo day, which is where the momentum is. Turned down the acquisition. And this person who was supposed to be my partner… After, I think she was at Wedding Lovely less than a year. Wasn’t like “Hey, we’re having problems, let’s talk about this.” It was literally like, “I have a new job, I’m leaving. This is my last day.”

Garrett: Yeah.

So much depression. I don’t think I did anything for the following month. I had already laid off the employee that we had due to budget issues. And so it was just me. She left, it was just me.

Tracy: So much depression. I don’t think I did anything for the following month. I had already laid off the employee that we had due to budget issues. And so it was just me. She left, it was just me. And I was lucky that Wedding Lovely was working with these businesses and that it kind of ran itself. Because I don’t know what I did. I don’t even remember. It was terrible. I think it was during December, so maybe I got distracted with family and just ran off. And I think it was only a few months later where I was like, “Okay, maybe I’ll actually start adding more features and working on this again.” It was a really tough period to have this person that was supposed to partner with me and said “I believe in you.” Just to be like, “I don’t believe with you.”

Garrett: Yeah.

Tracy: “In what you’re doing. At all.” Yeah. That was…

Garrett: That’s the situation where it would be so easy to just give up.

Tracy: Yeah, and it’s kind of funny looking back on that. I could have just really easily just shut down and started on something. But it was throwing me money.

Garrett: Yeah.

Tracy: I still was being paid from it. I think my salary was 20k. So, not that much.

Garrett: Yeah.

Tracy: But again, I didn’t have rent. So I was like, “Well, I might as well just go…” Do whatever I did during that time and just enjoy having an extra 500 dollars every couple weeks.

Garrett: Yeah.

Tracy: To keep things afloat. Yeah. I could have shut down. A lot of times I’m like, “Wow, if I shut down this four years ago, who knows what my life would have been?” I could have started or joined another startup as a designer. I could have started another thing. I have so many ideas I’ve wanted to build that I haven’t built yet. But you know, in hindsight’s always 20/20.

Garrett: Yeah, oh of course. So have there been plateaus in growth that you’ve had to break through? And if so, how did you break through them? Was it a certain strategy, was it just time and tenacity?

Tracy: Yeah. It’s always been going slow. Even during the exciting points where we had VC funding and all this other stuff. And that’s one of the things that’s always been hard for me. Because every time I look at the growth graph, I’m like “Oh, we’re just at that moment where it’s going to go that rocket ship.” And that rocket ship has always just been like this constant, steady, uphill slog.

And then other problem is with working with these businesses and doing this marketplace when I’m saying “Hey, I’m going to help you find your vendor.” When we first started, my first launch, that first directory, there was ten people on it. So it’s useless.

And so with the marketplace where it’s just like, “Oh, okay, we just hit 8,000 vendors. Now it’s really useful to people. Now it’ll take off.” So a lot of it was me saying, “Okay, I don’t have this explosive growth. But I also don’t have the number of vendors in the directory that would support this?” I don’t know, maybe I’m just fooling myself. But it was this constant like, “It’s okay. Maybe it will happen. Oops. Later on.” So, in terms of plateaus. I guess plateaus really have been just mental plateaus for me. Going through these periods of depression where things didn’t go too well. And then somehow being like, “Okay, cool. I’m going to start working on this again.”

And then, vendors. Every time I think about quitting, vendors send me a really nice email talking about how awesome it is. Which is like, “Oh, okay cool. I’m going to continue working on this a little bit more.”

Garrett: That’s a really key point, I think. Because when you’re running a business, or really doing anything, the only people you hear from are the people who are almost satisfied. Because the people who are completely not satisfied don’t care and aren’t going to take the time. And the people who are satisfied aren’t going to bother, or they’re going to email you and make a request. Nobody ever, not nobody but, one in 50 will email you and tell you, “This is really great. It solved all my problems.”

And so you just don’t hear from them because they’re happy, and they’re focused on doing their thing. Which makes sense. But as a business owner, it’s so hard to force yourself to remember that and to say, “You know what? There are people using this and paying for it and appreciating it and getting value out of it.” Because you don’t hear from them.

Tracy: Yeah, one of the best things I ever did actually was changing my auto-responder emails. When a business signs up for Wedding Lovely, they get opt into MailChimp auto-responder. You know, one week, two weeks, six months, et cetera. And I switched them over from html, very newsletter-y looking emails, to things that look like personal letters from me. And that has, the amount of people that respond to those. Even just to say, “Oh, thanks for the information.” Has gone way up. Which has been so great for mental, feeling like you’re doing something awesome.

By having these random little responses. I am so happy that I switched over to this plain text, very like, “Hey, by the way. Did you know you can add another image?” I know that a lot of people have been talking about that. And I’m just going to jump on that pile and say, “Don’t use HTML emails. Just write something that looks like it’s a human.”

Garrett: I did the same for Sifter. I did it with just one email, though. And originally I sent it out by hand. And eventually got to the point where I automated it. It was still plain text, but generally, I was way on top of it. I would reply within five minutes to that email. And there was even one time where somebody asked me, they’re like, “Is this automated?” And I replied back, “Nope. It’s real. There’s a human on the other end.” And then, he kept poking and testing, because he though it was this whole…

Tracy: A really, really smart automation.

Garrett: Yeah, really. And I’m like, “No. This is legit. What can I do to prove it to you?” And he’s like, “Wow. That’s really fast.” Because it was too fast. He didn’t believe it could be real. So anyway, yeah.

I had that same response. And to me the whole goal was just to create an interaction and make it so people realize that I was approachable and they could ask for things, and request for features, and share ideas or whatever. And that really helped.

Tracy: Yeah, it took me a long time to move off of Gmail with everything. There’s this new app, and I’m not being paid by them, I just started using them. It’s called Front. And it’s the first support software that doesn’t… Not first, there are probably other ones. But it’s the first one I’ve used that didn’t make it obvious that responses were coming from a support software.

So I was able to set up all of our random emails like hi@ and hello@. So that the virtual assistants and then the two other, I call them minions lovingly. The two other minions I work with, you can see when someone’s going to respond to something. But when they respond it’s not like that dot, dot, dot, dot “Respond above this line”.

Or something that looks really fake. I used Gmail and just used filters and we all kind of coordinate for so long because I wanted to have it look like, “Hey, we are actually responding to your email. We’re not some…” I say “We’re not some foreigners in a different country.” Except again, my virtual assistant is in the Philippines. But she’s amazing. An awesome person. And not some random support staff I hired. She’s a full member of Wedding Lovely.

But it looks like this app is a lot of money, but it’s the first support app I’ve used that has that really personal feel.

Garrett: Help Scout works that same way. That’s what I used with Sifter, and that was the selling point for me, it was the same thing. It’s like it was a human app. It didn’t feel like, you know.

Tracy: Yeah, there’s so many out there, so many support apps out there that don’t do that. And when you get that email back, and it’s like “respond above this line,”” it’s like, “Ugh.”

Garrett: There’s nothing I dread more than getting a response from Zendesk. As a customer of the company. And then it’s from Zendesk. And I’m like, “Crap.” This is going to get lost, they’re not going to care.

Tracy: Talking to a robot.

Garrett: It immediately sours and scares me away.

Tracy: Yeah, that was one of the thing that was really important for me with Wedding Lovely. Because there’s so many wedding businesses out there that are very faceless.

Garrett: They have to be. Right? If you’re doing consumer stuff, you can’t scale handholding everybody.

Tracy: Yeah, so I use a lot of smiley faces. It’s actually in our brand guidelines internally. I was like, “Smiley face and exclamation points, and when we make a mistake, it’s going to be like hey, we screwed up, and it’s going to be human.” And so the businesses I work with and consumers are both like, “Oh, you can actually talk to a real person.” Actually, there’s in the planning app, I have this little box that says, “If you have any questions about venue, send it in and we’ll reach out to our business partners.” And very few people use it. I need to, I hope more people use it, it would increase my support I get. But, it’s always fun when someone’s like, “Hey, I’m trying to decide between these two venues.” And I have these vendors I work with, so I can message them in the area. I’m like, “Hey, what’s your opinion between these two venues?” And they respond back and they send that feedback over to the consumer.

And they’re like, “This is amazing.” And then the businesses are like, “This is really cool. You’re acting with Wedding Lovely.” And it increases their appreciation for my company.

Garrett: Yeah, absolutely.

Tracy: And it’s this win, win, win process. I need to get more people using that. But the whole acting like a human, helping people plan their wedding has been really important to me.

Garrett: And I think a lot of people too are almost scared of being too tiny, right? They’re afraid people won’t trust them if it’s a small business.

And I think the reality is, if we all think about it, we enjoy interacting with small businesses. Because, I guess with technology there’s some fear there and trepidation. Because if you’re too small, how can you be doing things right? But in general, for support and that kind of thing, to know that you can talk directly with the team running it, there’s a connection there that you can’t replicate and the big companies can’t compete with.

And there’s a lot of people that certainly appreciate that. So it’s not a bad thing to reveal like, “We’re not some huge, faceless corporation.”

Tracy: Yeah. It’s funny, I just did a big update to the back end of Wedding Lovely. And I sent a message out to all my customers like, “Hey, I did this huge update, you can’t see anything.” Because it’s all in the back end. But I was like, “Hey, but some things might be acting wonky because I might not have found all the bugs.” And there were bugs. And they would email back, email me and be like, “Hey, this isn’t working.” And I’m like, “Hi”. If I haven’t talked to them before I’m like, “Hi, I’m the founder of Wedding Lovely. I also coded this, so it’s my fault, but I’m working on it.” And they’re like, “Oh, that’s funny.” Almost say like, “Hey, I’m the one who actually built this and I’m sorry because I broke it.”

Garrett: People are incredibly understanding.

Tracy: Yeah.

Garrett: So, we kind of ran a little long. But I’ve got a couple more, and really they kind of go hand in hand. But if you could go back in time and tell yourself one thing. At the very, very beginning of all this. And know that you would listen to yourself. Whether it’s something like, “Watch out for this.” Or, “Go invest time to learn this, be prepared for this.” What would that be?

Tracy: I love Etsy and that acquisition process was really fun to go through. But that was the turning point for my company, as I mentioned before. And I would be, when it comes to acquisitions, it’s super cool when someone as awesome as Etsy comes to your company and says, “Hey, we’re interested in maybe buying you.” And it’s like, “Boom! Oh my God, amazing.” If I was able to up front be like, “Also, I can’t accept anything lower than this.” It would have saved me so much time and that momentum in my company wouldn’t have dropped. I always look back at that moment of just feeling like, “Oh my God, this is it. I’m going to be acquired by Etsy.” And not really thinking about what would happen if we weren’t. I wish I was more suspicious. I wish I… It would have been nice not going through the process. But at least just being up front about making sure expectations are at the right level. Would have changed probably the entire direction of this company. That would be one. And the other one would be, I did this, I talked about it in MicroConf last year, where I launched Wedding Lovely as a bootstrapped business. I’m like, “Yeah”. And I started making money. I put in paying features pretty early on. But if you want to build a business that’s VC backed, it’s a lot better we don’t have money. Because they can’t point at any numbers and be like, “Well, why aren’t you making more?”

When you’re not making money yet, it’s like the sky’s the limit. And it’s all this imagination. So I went with bootstrapping, and I went through 500 Startups, raised VC, then I went back to bootstrapping, and then later on someone, a investor came to me being like, “I believe in you. Here’s a 20,000 dollar check.” And I was like, “Ah.” I got stars in my eyes again, and I took it, and I was like, “I’m going to fundraise again.” Which, four years after a company starts is a terrible time to fundraise. Because A, I had numbers that people could point at, and then B, it’s like, if you’re not successful in four years, why would you be now?

So that fundraising kind of failed. I kept that 20,000 dollars, and she’s invested with me. But I know she’s disappointed with me. So that’s flip flopping. When you start a business, you can flip flop once. But don’t go back and forth. Because every time I switched… The way you build a bootstrapped business versus a VC business are so different.

Garrett: Different, yeah.

Tracy: And every time I switched, I put the brakes on stuff and turned a different direction, and then everything got jumbled. So, people will be like, “Hey, pick one and stay with it.”

Garrett: And so the next question is, if you were starting over again today, would you still do Wedding Lovely or would you go in a totally different direction?

Tracy: I love Wedding Lovely. I would… I am not a weddings person. I like working with small businesses. I got married a few years ago and I eloped in Vegas, because I was like, “I am not going to do this wedding stuff.” And I sent a message to the vendors I work with being like, “Oh cool, I got married.” Because again, that whole being human with them. And a lot of them messaged me like, “Really? You eloped?” I had this opportunity where I could have worked with the businesses.

Garrett: You run a wedding website.

Tracy: Yeah. I could have, and a lot of wedding businesses do this. Where they partner with their wedding businesses, they get a deep discount on services from these partner wedding businesses because they turn into this cupcake beautiful affair and then those images go onto wedding blogs, and then everyone gets the traffic from that. I had this opportunity to, not really exploit, but do that.

Yeah. My husband’s wedding ring is actually a free wedding ring, wedding band. It was less than a hundred dollars worth. But we were, I was interviewing this jeweler, and he was like, “Oh, cool. You can have this wedding band. You’re engaged. Here you go.” Like, “Cool, free stuff.”

Garrett: Nice, yeah.

Tracy: So yeah, not a wedding person. I eloped. Being in the weddings industry has been very frustrating, because that customer acquisition year over year is such a weird business that I probably would choose something completely different and my life would be a lot simpler. But, I’m here now, and I’m stubborn. So might as well just keep running it, even though I’m not really running it right now. I have my minions.

Garrett: Yeah. Right on. Okay. Well so that’s all I’ve got. Thanks for being on. This is has been awesome. And I think there’s a lot of really interesting stuff in here. So, it should be fun.

Tracy: Awesome, I love talking about how much of not a huge success I am.

Garrett: No, no. But it’s so easy for people to get caught up on whether they’re a relative success in the larger market. But that’s not, to me that’s not the point, right? It’s getting people to have the confidence and be able to set their expectations correctly. To be ready to stick it out in the long run, right?

Tracy: Yeah.

Garrett: Because so many people have out sized expectations, and then they give up too soon, or they never even start. And I think there’s a lot to be said for helping people anticipate that pain and say, “Oh wait, yeah, that’s going to suck. But I can handle that when I get there.”

Things are going to go wrong. And the more we all learn from where we all went wrong. Whether it was chasing an acquisition or whatever it was, then the next person can be like, “All right, I know to be a little more skeptical now.”

Tracy: Yeah, exactly.

Garrett: And that can make a world of difference because that next person now might say, “You know what? I need this amount to even talk to you.” And they’re like, “Oh, well yeah, we’re not even going to come close to that.” Cool. You just saved yourself a bunch of time selling your product.

Tracy: Yeah.

Garrett: And so I think there’s just too much hidden wisdom. Because we go through all these pains and we don’t share them enough. So.

Tracy: Yeah.

Garrett: I think there’s a lot of that, and that’s good.

Tracy: And there’s a lot of stuff you only learn when you go through it.

Garrett: Right.

Tracy: I’ll probably make the same mistakes again, because it’s… When you get the stars in your eye, nothing can go wrong feeling, it’s hard to get over that feeling, too.

Garrett: Yeah. It really is. But hopefully, this will help.

Tracy: Yep.

Garrett: All right, well thanks again. Thanks so much.

Tracy: Yeah, thank you for having me.

Garrett: Of course.

Support Starting & Sustaining

This episode is just one piece of a much bigger puzzle. Starting & Sustaining is a complete system to help you build and launch a web application with less pain and fewer mistakes.

The Package

An illustration of the checklist, book, and spreadsheet.

The Audiobook

An illustration of Starting & Sustaining on a mobile device audio player.

The Book

An illustration of Starting & Sustaining on an iPad.
An illustration of an envelope with a wax seal.

Once-a-month emails Focused emails on SaaS topics like email, security, onboarding, pricing, and more.