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Episode 455 | Things I Would Have Done Differently with Tracy Osborn of WeddingLovely

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In this episode of the rest of US I talked with Tracy Osborne of wedding lovely about things she would have done differently. During the nine years she ran wedding lovely. This is starting to the rest of US episode four hundred fifty five for the rest of us the podcast developers designers awesome in building launching at growing suffer products with you've built your first product. Are you just thinking about it. I'm rob today with Tracy Osborne. We're GONNA share our experiences to help you avoid the same mistakes we've made Oakland this week's episode of sort of the rest of us on this show we talk about building startups in an organic sustainable fashion then well. We are ambitious founders who want to grow our companies. We don't do it at the expense expense of our life. We've many different show formats often times we will talk about tactics and teach things we answer listener questions. We have some founder hot what seats and today I'm doing an interview but it's more of a conversation with Tracey Osborne founder of wedding lovely which she ran from from twenty ten until late twenty eighteen and I believe she actually shut down technically in early twenty nineteen tracy and I now work together at tiny siege. She's she's the program manager for the accelerator and we've known each other for several years now. She's put microcosm in twenty sixteen and believe that was the first time we met in person and then obviously obviously we've gotten to know each other much better over the past three or four months as we've worked together on tiny seed what I like about Tracy story is that it really is a story of highs highs and lows from teaching herself to code to bootstrapping the company in two thousand ten and then going through to accelerators accelerators. Although one of them really didn't put much money in winding up going through five hundred startups wedding lovely was really hitting on all cylinders and then catastrophic stuff tough happens and it's fascinating to hear her thought process of some regrets thinks she would have done differently and other things that didn't turn out but she made the best decision she could at the time and so I really appreciated Tracy's honesty and transparency and interview today I think it makes for an interesting story like several of the guests we've had on recently who are able to dig into decisions. They made things they might have done differently as well as things that that they did do right and the learnings took away from from running a startup as quick background wedding lovely was a blog and a wedding marketplace that matched up wedding vendors with couples who were we're going to be married engaged couples and with that bit of background will take you right into the story. Thank you so much for listening. If you enjoy this interview. I really appreciate appreciate it if you'd reach out on twitter I'm at rob. Walling and Tracy is at Tracy makes so let's dive in Tracy. Thanks thanks so much for joining me on the show this week. Thanks for having me so listeners already have some context about wedding lovely and how you started at. I want to start by looking at the decision you made to move from bootstrapped to taking fifty thousand dollars in funding from five hundred startups what led to that happening and how Oh did you make that decision. That was a really tough decision because I think before five hundred dollars happened. I was fully in the boost dropped camp and this is two thousand thousand eleven so there wasn't you know tiny didn't exist all these other alternate funding or different paths. They didn't exist so it was like. Are you going to do a full funding route or go bootstrapping that was it there was no middle ground and I was fully in the bootstrap camp. I think I was already falling Patrick McKenzie patio eleven's writings about this at the time and <music>. I joined the designer find San Francisco which is totally different than how they are now. At the time it was kind of like a small small accelerator ish thing where we got a really really small chunk of money and just worked together for three months meeting up every week just to work on our projects together and one of the designer fund founders was a a mentor at five hundred and he decided to set up interviews with five hundred just in case for everyone who was in designer fun so for me. I was like okay. This is a good practice. This is great for me to go in and practice pitching and whatnot and it was a really interesting experience because I met with Dave McClure and Paul Singh <music> who is involved with five hundred anymore with Paul. I and Paul was like I've seen your articles. I've seen you talk about wedding lovely what you're building. I think you're awesome a call me cockroach which I thought was awesome. He's like you'll never die. You're persistent. You're in there like you're in and I was like well that was easy and then I sat down with Dave McClure her. I gave my presentation and he said all right. We'll get back to you soon. I was like Oh Paul said I'm in and that totally Dave McClure off because they didn't talk about this. I think I totally threw it off through everything offered Dave McClure and probably what they're planning and at that time. I wasn't sure I was take it yet but it was kind of thing whereas like okay cool. I have this opportunity opportunity to go through five hundred my husband had just gone through Y C and I knew I knew I was really into bootstrapping beforehand but it was just it was like okay. I have this offering table. Let's see what happens those kinds of the thought process about it like not everyone gets this kind of offer this this chunk of money and I wasn't ready. I I don't know like hindsight being twenty five. That's where I hesitate now because I looked back at the decision it'd be like I should have thought more about this. I should have thought about what goes into like know more about what goes into funded company that kind of growth. That's that's a required when you're a funded company. When you have investors what's involved with raising a full series a that kind of stuff but it was kind of like okay? This is going to be a learning experience. I have this is opportunity here. I wash my Hawaiisale. Let's do it the hard part that I see with the five hundred startups investment was that they only gave you fifty fifty grand but it came with the expectation of well now you're on venture track and it's not enough money to act like a funded start up in my opinion but it sounds like you you wanted added to or felt the pressure to start acting like a funded start up yeah for sure and it was there are so many other complicating factors my time in five hundred was I. I did not utilize it as well as I should have and I'm taking a lot of stuff. I've learned actually from being in five hundred to what we're building. A tiny sued some of it was I was a solo founder and ends complicating factor is funded another wedding company the same time in my batch and they do also thing where they they also required you to get desks at their space and they've sat us across from each other and we were not friends. I WANNA be friends with them but the other people they're very aggressive very that's like stereotypical startup like that bad stereotype. You might think of started founder. That's how they were from H._p.. H._B._O.. Show Silicon Valley or something exactly I were not friends and it Kinda IDA's felt so awkward being there with a competitor and they actually pivoted more into my space during the batch and so I didn't show up to any of the networking stuff. I didn't do any like the evening stuff. I didn't really connect with the other founders say my own little world heads down work on things hired someone at that time brought her on this is the time that I found a CO founder which talk about later but in terms of five hundred. I didn't really involve myself in the program. I didn't really utilize the mentors are there. I didn't do any I think using the hell. The five header gave me and I look back in that time. Wow I wish I could redo that because it was my my social anxiety just came into play. There and I didn't use it as well as I should have right because as as we've we've heard from so many people in the tiny batch the community and the mentorship is is at least as valuable if not more valuable than the than the money they invest and I it sounds sounds like you feel like you squandered that opportunity a bit absolutely like you know. Networking is so important to one's career and the connections I could have made hey during that time like who knows where I could be right now. Maybe the same but like if I use those connections there's some people in my batch that have gone out onto really really amazing things like what I was looking for a job those kind of connections. I would have been really awesome if I was trying to find a job somewhere but I didn't like. I've completely lost contact with them. I wasn't the friends with them during the badge I who knows what would have happened so I look back in that time if I could have redone the accelerator program absolutely be involved in using the opportunities are available available something I didn't do. I regret that. Do you regret the decision to take the funding. I think I would say no. We'll do a whole podcast and how insane the weddings industry is and I talked to a lot of people who are jumping into the wedding industry because they look at it as like this this industry where a lot of people are spending a lot of money and therefore it's GonNa be really easy for someone to build a startup. Just take some of that money. Oh yeah they're just you know Alfred spending thirty thousand dollars a wedding purse O- pay ten dollars fray APP egg. It's way more complicated than that and the thing with wedding history because there's so much competition there's so many start the ups and so many people trying to like compete for people's attention and you'll have one hundred percent sure and after year because all these people are dropping out of your platform it means that advertising is a really big thing. Advertising is really expensive and so that chunk of money did help like I could apply it to things to help boost the business as like absolutely necessary. I think in the wedding street if you're targeting people who are getting married so money was used. I also use that to hire someone that was great. I did learn a lot from being in the program. They look back on it being like okay that it was a really good learning experience and I wish I could Redo it but I don't wish I did something differently. I guess that's why I say I wasn't perfect. It wasn't a perfect experience but I learned from it and for better or worse. That's how I got. 'em Right now and at the end of the program there's a Demo Day and that's where folks raise essentially raise their seed round or precede receive around these days. I guess and you decided not to raise around. I believe you had a co founder by that point. Do you want to talk a little bit about the Co founder and then a decision you made need to pause funding a right eskimo day approached right yeah the roller coaster of wedding lovely. This is the peak like I was. I was in five hundred again with using the program as much as I could have but at the time I was like cool. I'm doing everything right because absolutely amazing awesome person Julia Grace. I believe she's a director infrastructure threat at slack now she reach out to me asking me if she could co founder and I was like just person is amazing. She's amazing Genera. She would be Great C._T._O.. Absolutely come join wedding lovely so Julia joined. I was in five hundred at the time I was travelling in New York and Oh. I can't remember his last name. Kellyanne Kellyn was the C._T._O.. Of ESI and he invited me to come into Oetzi for lunch and I was like you know again cloud nine. I'm kicking ass. Everything's going Awesomely C._T._O.'s ESI. It's the are inviting me to lunch so I go over to at sea for lunch and he drops the bomb on me saying like hey. Let's talk about acquiring wedding lovely. I was just like again of cloud nine. Oh my God I'm doing everything right so the day was like right around the corner and Juliana side dot to like really pursue it because we wanted to focus on on being acquired by eds because I loved at sea Oetzi was would be a great fit for wedding lovely what they were doing at the time they're they're switching some focus into wedding so it would have been a really awesome fit for both of us. I did do day through five hundred and I gotta say I bombed the first two months. I was much better presenting. I am now but I I look back on my first two pitches pitches at Demo Day because they gave us two two minutes to be on stage. It's really stressful. There's an audience of people and I just I did not do well for the first two by the the third one we did in Newark. I finally got my Yup Do you have a regret regret around that of just knowing most acquisitions fall through but it doesn't feel like that when you're in conversations with them. It feels like it's going to happen and so do you feel your judgment was clouded there or do you feel like you made the right call again. Hindsight being twenty twenty definitely judgment is clouded. I like not as good as a public speaker whereas I am now. I know that I didn't prepare enough. I know that I kind of this. It's a silly thing to think about but I was like oh just roll up and I just give my little two minute presentation speaking of like two minute presentations are the hardest thing in the world like it's really hard to give like a proper presentation such a small amount of time so it's really hard to hit all your marks and stress about like making sure you remember every single moment in that presentation because you have such small amount of time so yeah. There's some there's a lot of regrets for that again. It's also an opportunity if I kicked kicked it all the park. Even though I didn't I didn't decide to raise money then but the connections I could've made in that audience of the V._C.'s who were there people I could have met the people I could have connected with. This is another thing that I regret not doing like I'm a huge fan of networking and meeting as many people as possible and becoming friends with with as many people as possible because those are the the things that are going to transform one's career down the line and a lot of the things that where I am right now just because of connections I made beforehand like this tiniest thing. It's probably 'cause I met you Microsoft Microsoft like you who knows what's going to happen down the line and I regret not like trying to pay attention during those days and making those friends and making those connections and just being consumed by eggs -iety making my presentation and that running out I've done very similar things especially early the on this probably ten years ago but I would go to conferences and I was so I'm an introvert and I don't like meeting New People and I get stressed about it and I wouldn't meet this. The other speakers occurs and I was anxious to talk to people and so I know how that feels and I learned from that pretty quickly because I saw other people having those relationships and I saw they did both for their kind of sanity and wellbeing but also for their businesses and just the opportunities that affords saying yes to the things that scare the hell out of you often will lead to things years down the line as you're saying that you never could have predicted but that change they changed the game for you and I literally look back at my history not to go off on a tangent here. I had a very similar experience where I had never met Jeff Atwood of coding horror he and I blog and we used to email back and forth and we'd linked to each other's boy. Put them in this is two thousand five six seven. I never met him in person. He was running an event and I I was super terrified but I went up and I was just like hey man. I'm rolling and he's like hey I love your blog blah blah blah and we were talking and he's like you go into business software and it was like no. I'm not really just kind of not my thing and he's like well. We'll you should go let me just linke over to Joel's Polski and so just that that step moving forward like it. These are the things of like getting over those fears <unk> overcoming fears and taking risks is really what this is about even if even though it's hard I have something similar. If we'RE GONNA go even farther back in time I feel like like my career is is directly leads from my university graduation graduating with an art degree. I was really into web design but none of my classmate all my classmates were into product design or more like physical mediums and our keynote speaker at our commencement was a designer from apple came in and speak and I was like Whoa a web person. She's talking about women's stuff. I talked to her afterwards and she said and this is two thousand seven she said if you want to get into the web industry you need to go south by South West and again. I have so much anxiety I told podcasts about how much social anxiety I have. <hes> did a keynote drink okon you us about it and it was the most terrifying thing I took her advice and I myself a hotel room and I went to stop ourselves. Alone didn't know anyone there and it's overwhelming and I love the party. I just walked in panicked and walked out on the flight back. I I haven't sitting near some attendees and those people became my friends in the bay area that interests me to more people and two more people that I I went to conferences with and that's like a direct line to where I am right now. There's a concept that Jason Roberts on texting talks about. It's called Your luck surface area increasing senior luck surface area by doing a lot of things and I've often thrown around. I love the quote from Thomas Jefferson of like the harder I work the luckier yet but this is different because not necessarily hard work unless you consider just getting over your own fears hard work which I probably do but it's like taking risks often equates eventually you take enough of them in it gets you to to some quote unquote lucky outcomes but they really aren't lock you know right. I am so happy like on the anxiety topic it's still rears its head now but like ten years in like actively working working on reducing it and making sure that I I've going out there like being open to these opportunities has been. It's been a hard but it's been worth it. I'm glad Obama better now and so two to resume the story you were you were talking to you weren't putting much effort into the fundraising and preparing for Demo Day kind of counting on their Nazi thing working out. They did ultimately make you an offer what was what was that like when you received the offer and was was email. Was it a phone conversation. Talk me through the emotion of that well. Does it back one step. It was funny because I had I had the final meeting in York and again cloud nine like we've flown into New York put up in a really fancy. The hotel offered like a non fancy hotel and they're like no. We're going to put you up in the says but it's like the one where all the celebrity stay at in Manhattan so like put me up in a fancy hotel. Now we had the holidays meanings met with Chad Dickerson went out to a fancy dinner afterwards with me Julia and all the top level team and again. I'm just like I am kicking being but this time I'm talking with five hundred Dave McClure helped me out. Give me prop two four like what happens in an acquisition and how do compose everything saying and how to compose myself and I had other advisers in the bay area there helping me figure out valuation like didn't want to give a first number ourselves but I wanted to have a good range range of what a good valuation for my business would be so. I don't make bad decisions so I thought you know I'm the prep work was great and I think I did everything right for that but it came. I'm in an email and it was <hes> financial person one of the C._F._o.. It was a financial analyst or someone at N._C.. You Send Me over or knows a call. It was a cost also sat down with me and Julia it was a call and they gave us a number and the number was one fourth of what the lowest valuation all of my advisors said that wedding lovely is worth especially considering that as he had told me that they were going to keep the website up so it wasn't just GonNa be an aqua hire or they were going to use the properties and I was like okay. Thank you don't say they are the call. All Hung Up. Julian are like Oh crap and you know we would back and forth and like okay. It's a negotiation so what is like give another number and see if it it can beat somewhere in the middle so we sent back an email saying thanks that was not what we're looking for. Blah Blah Blah. Here's what we're actually think. The business is worth and they responded bonded with completely unexpected back. This respond with okay does not look like a fit goodbye just like devastating 'cause I expected this whole negotiation process and it was so weird. It's so weird to me today that that's how it happened and like all of my advisors. The mayor like what is he doing. This is not how an acquisition process is supposed to go we just went through for all the effort and they just went away and it wasn't like my counter was outrageous so that was weird and really devastating and and like I said we didn't do the like the full fundraising process when we had the best time for it which was demo day we didn't do. We didn't follow up on those those meetings this analysis like two or three months afterwards our momentum stalled. There's no like big you know five hundred startups day anymore and it was like kind of like okay. What do we do would we lost new product launch that we raise money then and then it got really confusing and really weird and very depressing and very crazy and that was about the time that Juliet decided that she wanted to move on to other opportunities? It's always like this high that was on before just like free fouled like it was horrible. It was the worst part of the business just a couple of months. It just went from top to bottom bottom. I mean looking back. Do you wish you take an offer. Have you ever thought about that. Even though it was low it wouldn't have made sense at the time if you had everyone would have been like you're nuts but what if you had do you think that would have been a good thing I go back and forth on that all the time it was. I can't say numbers that came him out to be kind of like a hiring bonus essentially in so if I was like okay I'm going to be a proper founder. I'm glad I did not take it because that was ridiculous number like everyone agreed read that it was a ridiculous number. I shouldn't take it up by you know having that stamp of approval that oh I got acquired by Oetzi on my resume what doors without of open because people just look at those those titles that achievement and then assume you're so much more awesome than you're actually are I wish I had I wish I had that which I had an acquisition on my record hard working at N._C.. Probably would have been really great fine. I would have avoided that devastating drop of what happened afterwards with Julia leaving layoff if someone that's when I switched to business back to bootstrapping because there was no way I was going to be fundraising at that point and I was just like kind of gave up on it and the way the wedding lovely was built. I could just put on autopilot so at that point I was just like okay business. Go do your thing and I'm just GONNA go over here in a corner and curl up and be really sad you're at the highest point and within a couple months you have lost this acquisition offer that you really thought was going to come through Oetzi essentially walked away from the table cable which is kind of surprising I had in different acquisition talks that that I've had companies have walked away from the table but they'll come back a couple of weeks later. Did you think thank you expect them to do that or when. They said they were gone. You were like this things done this a while ago. I'm trying remember exactly what happened but I know that the feeling was this thing is done on and I'm trying to think we had an advocate at the company and we shot to the advocate. He was like this is weird. I'll get back to you. Oh and it sounds. I think what happened. The end sounds like there was some weird miscommunication. Something happened on S._e.. Side that I am not privy to but something nothing happened on that side where they're like wait this decision rocket. I do it and it wasn't how you do with wedding lovely. I think something something with financials or something but it was just like now we can't we can't do this right now. Wow and so that falls apart and then Julia leaves shortly thereafter so what does that like. I mean when Julia calls or emails or that happened. How does that make you feel? Obviously there's gotta be some despair and stress but were you were you at that point. They can like this isn't going to work like I should just shut. Shut this down. Everything's everything's falling apart. The day of Julia's sent me an email insane all right. I'M GONNA come to your house work. 'cause we didn't have an office. I think we had an office for a little bit in mountain view at the time I think we shut down also because everything was free falling and she asked to come over to my house and so we sat down my house and she was like okay. I'm just gonNA open with this and if your exact word she said but essentially it was like you know wow this has been a really interesting experience. I'M GONNA move onto designing else so kind of like call us back. I did not expect that and I think I just like okay. Maybe you should go home now. I need time to process this. Thanks for driving all the way down to my house. She left and I walked around the neighborhood with my dog. Just dying just like Oh my God what just happened. I can't believe this happens and like I was really bad at Julia for a long time and I'm not mad at her now by the time it just it felt very personal like it was very much she she didn't believe in me and a lot of a lot of the business lot of wedding lovely a lot of it's my personal mistakes I made as being the founder and the person started as CEO and I was number my title which is weird. There's a lot of mistakes I made but I took it so personally. I did not like her. Art At heart out to take it personally. It's hard to take the company failing personally and I think it's a lot of the reason why I didn't shut down because I was like clinging to this idea of I'm not a failure and if I shut down the business right now then it's me admitting that I'm a failure that everything fell apart and it's all my fault so by keeping the business up it was like no I'll keep growing. I'll keep building in the business I it's it's still going on and it's still making me money and I'm glad they built in the way that I don't have to like continually spend marketing money on it because I was marketplace yes and the marketplace part was pretty active at that point so I had these businesses working with me and it was just like it was just me trying to prove to the world that I can still make money lovely success. I guess the question that comes to mind is truly was with you for eight months and she was a co founder who came on two years after you started the company Tony. It's all hindsight again because he thought it would work out but do you do you regret that decision of bringing a co-founder on not Julia because we know Ju I mean I mean you're friends with Julius. She's a rock star so not for her in particular but do you think this would have been better easier different. If you had just not evaluated that you've taken a CO founder Ron I in hindsight being twenty twenty. I wish that I I was like okay. I'm GonNa say the founder but you could be the C._T._o.. I think that would've switched something in my brain. I think I think a lot of my being so offended by quitting. I was like what you're a founder like. This is supposed to be your baby but no it's because she started so late. It's not her baby. It's my baby. I built you know the first version of all the websites I built everything from scratch myself. Of course it's my baby and she came in and she updated some things she built some things yourself but it wasn't. She didn't have like personal feeling like I did and I think it was a disservice to everyone. Call her a CO founder when I think it C._T._O.. Or some of these other titles would have been a but are fit and then when she left. I think mentally just like we're logic. Thing would have felt a little better. I don't know that's how I feel about it and also just like you can't bring ah CO founder and a couple of years in I think they're no longer founder quote. I agree with that. I think the title is the issue here and I don't think bringing Juliane was a mistake stake at all especially at the time it was a good move and even in retrospect you made the best decision at the time but it rings true to me that that that title may be wasn't wasn't right because if a co-founder wouldn't have left I shouldn't say wouldn't have but there were I think there would have been more conversation more more consideration because you're right having only been there eight months. She was US less less tied to it than you yeah and like we didn't have a lot of a lot of good conversations back and forth I I didn't actually treat her like a CO founder and that's my fault you know the business I was running all the administration of the business. I was running all vision for the business like where we're going what we're doing whatnot and I wasn't really involving her those conversations which is absolutely a huge mistake because I wasn't allowing her also to feel to make it her her baby as well so when she left I remember being Guzman because I had no idea she was unhappy or that. She wanted wind lever. She's looking for other things. I had wished that she had told me that she was out there looking for and their job 'cause she. She told me she had a job lined up but then I was like you know years later I looked back back in that being like by was involving her either and if I we should have had that personal connection if we're gonNA make founders together of talking to each other and talking about things are going going right what's wrong and evolving her and how the business going and hoping her letting her be part of that planning in those process I probably would found out from her earlier on that. She wasn't then happy but I didn't know that and I think that was a big failure on my part as being a founder of wedding lovely and so you mentioned earlier that that after Julia left you went back to bootstrapping and was that the point where you put it on autopilot because I have a blog post from you in two thousand sixteen where he talked about putting it on autopilot but what what was the timeline like there. This is where things get a little bit like wavy thousand six hundred like now yeah it's. There's like a points where I was like okay. A wedding love is running itself. I'm just going to spend a little bit time on it. I started working on my business around then we wasn't really business. It was like I'm on my side. I'm just GONNA start writing a book because I need something they bring me joy in my life and right now what a lovely is not it this was twenty sixteen or this was twenty twelve twenty six okay. It's it's it's been so long that some of are these these dates kinda get mixed up but after Julia laughed I discarded during the business for a little bit not really working on it. I remember what I was doing. I think I've spent a lot of time but just in a depressed prostate. How does that manifest itself with you where you're just like sitting at your computer responding to email and you know not not actually working but feeling like you were trying trying to work or are you just avoiding work altogether? I think I did the bare minimum to feel like Oh. I'm still running why they monthly so I was still responding to support emails I was I think I'm still running the blog so that was a big part of wedding lovely that there was a wedding blog <hes> a lot of his income came through that because we had affiliate revenue and I was still dedicated to at least doing daily post every day because I was one of the ways one of my things I did well with wedding lovely was by having this big group of businesses that was writing wedding all this kind of representing and I tied them into our blogs. We got free content from that by sharing the businesses were doing so it'd be like photos from our photographers or real wedding post from our planners or dies into like looking at invitation designs from our designers and this allowed me to work with the companies that are on wedding lovely and give them something of value and also encourage them to move to paid accounts. Let's by running this weddings blog so that was probably the largest piece of involvement I had was I continued run this blog grabbing the content and from these people I had a contractor I was working with so I didn't have to move who thinks wordpress. I just took what emails sent to her. She put onto wordpress for me. Then I came back in and set up on social media set up the scheduled post and stuff so I I read that and it was like oh I'm still running a business. I told myself I was running a business but I was looking at the numbers. It wasn't looking at how many businesses were joining over time like was number going going up or down. What was my traffic like? It was complicated because I have different properties those running so look at traffic for all eleven properties was terrible and that's why I never looked at my analytics. Analytics and I didn't pay attention today. The data's going on and I just kind of just ran the blog and accept that the money that came in went straight through my bank account and yeah yeah kind of ran it as almost a side business or like a true lifestyle business that definition of literally just kind of is a salary and you're not you weren't more ambitious officious with it. It sounds like and at that point you have a blog post from two thousand sixteen and I'll quote unquote yourself back to you but you say the planning and marketplace could place sides of wedding lovely would probably grow faster with dedicated marketing and sales work but we'll grow naturally slowly but surely on their own two thousand sixteen is already shaping up to the the biggest year yet even though I haven't had much time to work on winning lovely. I'M NOT GONNA shut wedding lovely down even though I'm looking for a full-time job since it does largely run and grow by itself. Ideally I'll be able to keep feature growth as well by eventually hiring a remote developer. That's my baby wedding lovely. How does how does it feel to to hear that? Oh my God I haven't read those in a long time and everybody should read them because I have almost a memory of that. It's so funny who is that person what a lovely had this little peek because the marketplace was growing like I said it was growing and I was great because I didn't have to worry about it <hes> and then they affiliate sales on the other side was growing pretty steadily is one of the things I knew that would go away but Google's Magic S._E._O.. Turned in our favor and one of our blog posts got to the top of the results for very big listing and therefore the tons of money was coming in through affiliate revenue and saw the time. I was like Oh wow I'm doing this lifestyle business right. Our income has doubled overnight. I can use this income. I THINK AS Roma's time is when I decided to hire someone fulltime to kind of run everything for me like a a marketing person but she also helped do emails shoot also I ideally it was supposed to be like she was going to help do vision and run the company and ended up not happening which is fine by by hired someone in Florida I had a contractor the same person doing wordpress but she kind of grew into more social media stuff in Washington. I also hired a full time virtual assistant assistant in the Philippines and she definitely did all the all the nitty gritty stuff so I was able to train her to help out with the social media stuff and do all the support emails and kind of release me from doing a lot of those day to day things so then I was only doing salary taxes bookkeeping that kind of stuff so that was kind of like going back into like Hey I am doing this right. I'm doing it like a different way than when I was doing the whole Esi staff but I was like cool. I'm doing this lifestyle business the right way. Have people employed that businesses growing. I can start paying myself again. At some point I think at that time I started paying myself. I think thousand bucks a month which is peanuts but it was cool to be able to employ people and pay myself and was after I call it was fun. I don't know if it's recall always things are such is so hard looking back on that because you don't know what's going to happen right yeah but I mean in terms of what I've have learned and that time of having employees and running a wrote business and I brought me so much joy honestly to have these employees and be able to especially Johnny Marketing Person I reveled in being a good boss and I think I did everything correctly like she like she like she was engaged. She was working on things. I was kind a hands off. I directed her. I helped I was able to pay for classes like online classes to help improve what she was working on and you know hopefully now like i. I hope she takes it to her current jobs. It was really fun. I love being like okay cool. You know I'm working on this book business. That's bringing enough money to run myself so I'm pappy taking majority of the income coming lovely and putting it towards these other people and giving them a okay lifestyle. They seem to be pretty happy so I it was fun what happened between then and two thousand eighteen because at the end of October two thousand eighteen you shutting down so this whole time all the for the last five or so years. It'd be like I would like to sell this business says some pay. I'm just waiting for the right moment that ended up not ever panning out and two thousand eighteen is win that Google Magical nece just reversed itself and I knew I was going gonNA happen like Google with Google taken away Ale one day on the number one search results and then one day or not and I I had rescued this post a few times already by by switching things around and returning hurting the S._E._O.. Juice back to where it was and this time I wasn't able to do it. I knew that to fix the post or fix the income that was coming in. It'd make some like spent a lot of time time on it or write new post or do something because instead of our income increasing by half overnight it drops by two-thirds overnight. I was like the big panic moment of it was like it was that moment where I was like finally make a decision about this because now it's just not easy money anymore. Forced your hand. So was the majority of the income of the business coming from this one one this one post I leaned into it and that by beer regret because it's happening and that was like this is going really well. I'm GonNa Start More Posts Amadou more things for affiliate revenue and that kind of helped buffer everything and maybe like worried less about the income coming out of the business side where less income coming from other sources and know that when it dropped I totally like went to drop. I was not bad. I was like Oh look at happened expecting this to happen some day and I was you know if I wanted to continue working yeah wedding lovely at that point. I could be like okay cool. Let's switch our focus really quickly back over the business side because our metrics on business. I was not great. The people we had almost nine nine thousand businesses and pay hundred paying customers. This is embarrassing to say but it was like I wasn't really worried about it because I had income coming for those surface sources and I wasn't really looking looking for like ten percent month over month growth. I was just looking for just enough Totally understand how hard it is to quote unquote autopilot website or software company or a startup. I've heard people talk about like a sap should just be built to be profitable. Just like dry cleaner or a car wash right. The thing is is a most dry cleaners and car washes. Don't last ten twenty thirty years they do go go out of business and be it's way more volatile with these types of businesses because as you said Google can change overnight and other competitor can spring up just the online marketing stuff changes so fast that truly having a business that is profitable and lasts for ten years online without quite a bit of concerted effort every twelve twelve to eighteen months to fight the fires. I've done it. I mean I've I've owned fifty at least fifteen different software products and other probably ten fifteen different websites that made money from every conceivable thing from e commerce to content to add words to selling software one time to selling multiple software or subscription software to INFO`products. I've done them all all and in the end putting something on autopilot is so so hard to actually last anything more than one two or three years and that's that is why the multiples on a a lot of these companies are so low you know you'll see content site self for two years of its net profit and it's like well. That's preposterous. That's just crazy. That's a deal but then you get into it and you realize oh google smacks exit around every six months and you experienced that in full force and it sounds like if you had been focused on wedding lovely you would have probably diversified the revenue streams right you would have had to I use the S._E._O.. Because getting money from S._E._O.. Is Great from affiliate stuff. That's a great way to do it but to rely on it as the as the core focus and build most of the company on it obviously isn't GonNa last forever yeah and like I said I was not mad when I went away I was I knew that was going to happen. It happened earlier than I thought it would be like listening to this time because I was like that was a lot of effort. It was never like you said it never was completely hands off my brain power even hire people all I was saying so much brainpower on it after shut it down it was like this whole process of like laying off people I hired and shutting it down and Africa shut down people any hackers article that I wrote at the peak doc which was great at the time and now it's kind of like oh no because it's like talking about how amazing things are like that blog post. It's amazing czar and people are like why don't you just keep running it. Why don't you just keep it up the background? Why don't you put it back back to his autopilot? I get this email pretty often and it's because the brain power required just even have something there knowing it's they're getting even even a few emails every day or every week about it you know having the deal when something changes in your server and you have to go upgrade the server because everything broke or something like that like it takes Oughta time and it's really hard to focus on doing something else appropriately wean your split focus like that yep focus such a huge thing and it's it's. I think it's undervalued in kind of in our space in the blog posts that you you published in. I believe it was October two thousand eighteen about shutting down you said You you look back and you talk about your decision to put it on autopilot and you said my passion has largely moved elsewhere to hello web books. It's been my focus for the last couple of years but wedding lovely largely ran itself and it's making a good amount of revenue through affiliate and subscription accounts so I hired a team to keep it running a few years ago and stayed on as an advisor. It was the Lazy Way <music> out the business wasn't evolving significantly. No new features were being launched but the businesses and engaged couples that used our services seemed happy. I was able to employ a few folks who seemed happy as well so why not continue with it and that that kind of summarize it sounds like you still feel that putting it on autopilot probably wasn't the best idea but it was working for people you know people were using it. You're employing people and it was just a decision you made at the time yeah in the theme of this episode is always hindsight is twenty twenty like now that I have. I'm working at ninety eight having a job at the time I was like so hesitant to shut things down because I knew that I'd have to go in the process of actually finding something else like the book stuff stuff wasn't supporting me full time and I had the Sison whether I want to launch a new book or termite book thing into a publishing platform like go all in on this other project. I I was working on or find an actual job and I was so scared of finding jobs. You're working largely for myself for the last ten years in the only other two places I've been employed. They'd were terrible terrible experiences so I was like dedicated to working for myself. I thought that I could not have a boss and now that I have a job that I really enjoy. It's like what you know. It could have been four years ago when I dislike run the business and I had employed people and it wasn't really something I was interested in but it's kind of working on these other things you know if I made a decision for years ago to shut it down like where would I be now. I don't know the answer is and I'm really happy again with the path I taken but it is interesting to look back on that with the knowledge knowledge I have now and looking at previous decisions and be like Oh interesting. It's funny having this blog posts because I could see my thought process back then for better for worse. That's the hard part art. Is You said you had two jobs. You didn't like them and therefore in your head jobs are bad and you'll hear the same thing you'll hear people talk about venture capital. Oh Oh I read to tech crunch articles of a founder getting screwed by his V._C.. Therefore venture capitalists bad or you'll hear oh a business built their revenue on Organic Search S._E._O.. Theo and then google smacked him around and now they went out of business and this is a it's a common story. I've had entire products. Just go under because of Google therefore I'm never going to do organic search. It's like no these conclusions are too broad you know and they can shift. They frame your mindset in a way that you don't even you don't even realize and often times. It's if you found the right job up then it would be good. If you find the right money under the right terms it would be good if you use Google for the right purposes which is to get you enough money to that. You can hire for people to have other revenue streams diversified then. It's a good thing but it's it's thinking about it in in that way. We're all guilty of this and it's not something that's that's easy to I do but I think about some roles that I've hired for where I remember thinking. There's no way I can find someone to do this. There's no way that I can. We just can't hire for this role so I'm going to have to do it. I mean even program manager of tiny seat. It's like this is my is my accelerator on our night started this who can possibly run it in a way that that work and I remember I kept telling myself but if we find the right person and it'll work you know and that was what I had to tell myself to take that risk and of course we found you and you're the the right person and it makes sense and I'm so glad that you have taken over so much of the role that I would be just bogged down with day to day and not able to do the things that I need to do. Yeah it's funny about momentum. A lot of the wedding lovely was just not may not momentum but it's just being like feeling like I'm on a certain path and it's so hard to change path. It's so hard to consider consider the other paths are available when you have your currently in a Rut in I was in a Rut for a really long time and it was really hard for me to see over the edges of that right to see what else is out there or to conceive of the the work that would be required to jump out of the path I was on and I just like push out the pushing it year over year a year and telling myself myself like okay. It's great that I'm only making thirty or forty thousand dollars a year because I'm working for myself and I got the travel a lot. I've got to work abroad for a long time. I gotTa do a lot of really really great things. I allowed me to launch this book thing which also led to a whole other <hes> interesting set of experiences and learnings but a lot of interests like I got into this this right and it was so hard to move out of it and now that I'm out of it. It's interesting to look back on this experience being. I'm glad I had that experience. I learned so much from I've done so much much with it but I wish I doubt sooner. I wish I looked at the metrics. I wish I looked at how things were going. I wished I considered that there's other things out there that could fulfill me in the same way it would and I know they'll take those learnings to whatever I'm doing in the future so as all okay really great learning experience. I learned so much from it. I wish I did some things differently but I'm glad that I did it. Final question is as we wrap up wedding lovely could have worked like as an idea it was provided value oh you and and it could have provided you full time income and employed people. Why didn't it work wedding industry? Oh Man I could talk for ages about this. I'LL WE'LL TRY TO KEEP IT SHORT A. I'm actually don't like the wedding industry myself which is funny running a start up on the wedding industry but I told myself I jumped into the wedding streaks. I wanted to switch how it was done. I didn't really like this focus on consumerism and weddings and I wanted to have a place where it was like you know instead of worrying about building this this event where you have a to do list of five hundred twos long. What if you had a website that was more like a friend helped me through the process telling you just like the the the big things you have done like getting a photographer and why is she the photographer and what's going on so that was a good idea and I wanted to lead into this even better ideas I in the wedding industry? I wish there was a place like an all one booking platform like airbnb like they're a how great would be if you're getting married and you had this one platform to find people read reviews talk with them do some messaging and do the payments and everything under one area rather than like juggling. All these different vendors like that's one of the reasons like weddings are really crazy and there's such an opportunity here for that but but because it's like it's such a high churn like insanely high turn business where you know if you're going to work with people who are getting married and these people are going to like leave the platform Germany year enough to find a whole new set of customers kills anyone jumping into this industry. I did the best I could by working on the business side of things but combining the fact that the winning industry is really hard. It's really hard to have repeat customers. It's really hard to build a sustainable business on it and then the fact that I have not interested in going to wedding fairs I- I- eloped in Vegas I was not even going to touch a full wedding myself. It's not something I'm really passionate about. I'm passionate about changing it and I was able to use that passion in in that way but a lot of that also went into why it was not good for me to run budding lovely as long as I did and also why wedding lily itself didn't work tough business industry and little lack of product founder fit. It sounds like exactly I mean again fun process. I taught myself with a program program by building wedding lovely I by design skills improve. I learned how to do all this crazy back in stuff bill this like crazy marketplace. I learned marketing and sales sales to an extent like I it was a huge learning process and it was fun working industry I met I met him amazing connections. Would I ever do a wedding syrup again new. Oh I've definitely want to move onto. I like advising wedding startups and telling them all the terrible stories I have and advising them to well. I'll ever ever tell some of the change by trying to tell all the problems that happens in the wedding history when you're building an APP and why it's not as easy as you might think at a lot of people I find think it's easy but I've tried and to be the person who is very clear about the problems. I've had so that people can learn from it. Thanks so much for coming on the show Tracy with folks want to keep up with you online. Where would they do that? Personal websites TRACEY OSBORNE DOT com. I'm also on twitter as Tracy makes and instagram and other social media sounds sounds great. Thanks again thank you. I want to thank Tracy again for coming on the show. I like her story because it's not very often that someone runs a startup. It's hard for nine years and puts it on autopilot and hires a team to run it and just has these kind of the ups and downs and the experience she did and and her willingness to to relive that with today is much appreciated that wraps us up for the day. If you have a question for us caller voicemail number at eight eight eight eight zero one nine six nine zero zero or email us at questions at startups for the rest of US Dot Com our theme music is an excerpt from out of control by Moot. It's used under creative Commons subscribed to us and I tunes by

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