Ep # 6 | The Power of Story and Experience Sharing

Stacy Stahl

Stacy Stahl is the founder of HowHeAsked.com – the digital destination for all things marriage proposal. How He Asked, acquired by XO Group, Inc. in September 2016 to allow The Knot to better serve its audience even earlier in the wedding planning journey, provides a platform for couples to share their engagement stories. Outside of work, Stacy loves traveling and recently visited her 40th country. She grew up in Florida, and lived in New York City and San Francisco before moving to St. Louis with her husband and one year-old golden retriever. 



Shantel: Hey Stacy, welcome to the show. We're so excited to have you!

Stacy: Thank you. Hi. Hi everyone.

Shantel: Hi. Well let's just jump right in. We are excited to learn more about your journey, How He Asked and where you're at right now.

Stacy: Yeah. Absolutely. I'm so excited to be here. Thank you for having me. I'm the founder of a marriage proposal website called, How He Asked. We are a way for couples to share their marriage proposal stories and because we have a library of over 12,000 stories, we've also become a resource for men, women who are planning their proposal. We were actually acquired by XO Group who owns The Knot, The Nest and The Bump, back in September of last year. I'm working through a really fun transition right now, from being and independent, private company to being owned by a larger really great public company.

Shantel: That's exciting. Congratulations.

Stacy: Yeah. Thank you. Thank you.

Shantel: Well I would love to hear a little bit more about how you got started and what inspired How He Asked specifically and what made you imagine more and step outside your comfort zone to start this.

Stacy: Absolutely. For me, it was a lot of sweet spots as they call that ... As I call them. Just feeling a bout of excitement for the idea and combining that with feeling like I had 50% of the tools I needed on day one to just test something out. Then the other part of the puzzle is just continually keeping myself open to people and resources that could walk me through the remaining part that I didn't know.  I started a site. I was 23 or 24. I only had two jobs out of college. Both of them were at startups. I sort had this risk taking experience, but, it was two years long. On one hand I wasn't encumbered by the corporate ladder that I think people are trying to put themselves on. But, on the other hand I didn't have a crazy amount of experience. The last company I worked for was a for moms by moms daily deal site. That was back when Groupon was huge and whatnot. Most of our senior leadership were women. I felt really empowered just being in a company where the CEO was a woman, most of our senior leadership were women, and it was such a great community. Anyway, that was in San Francisco. I grew up in Florida and one of my friends asked me to be part of his proposal to a good friend of mine from growing up. He asked me to fly back to Florida from San Francisco, which is like literally the furthest you can go across the country. I was kind of clueless as to why he'd want me, a friend, to be a part of his private proposal. But, I went. It was one of the best moments of my whole life. Just seeing how happy my friend was and just being a part of the next moment and step of her life. I'm a very emotional human being so it just brought all the tears out.  When I got back to San Francisco ... Again, being part of this womeny sort of company, everyone literally ... The words were, "Oh my gosh. Tell us how he asked. How he asked." There was a friend that joked and said, "Gosh. This is kind of silly how these people who don't even know this girl really want to know her proposal story." Then, here I was sharing it with such excitement. I almost cried again just sharing it. I remember going home and saying, "You should start ... Or, someone should start a site that just collects all these stories so people can read them and yada, yada, yada." Again I was looking in the mirror and said, "Why don't you try it?" I honestly that night bought a couple of domain names. I had traveled a lot after college and obviously grew in the social media era so a lot of the things I needed to get started on this were creating a WordPress blog and opening up social media accounts. So, really the barrier to entry was just so low for me. Obviously taking it to a level where I was working with advertisers and growing audiences at different conversations. But, just starting it, it really was like, "You know what? I have nothing to lose and it's really not that much effort. So, let's see where it goes." That's sort of the founding story for me. Yeah, again, it was very low risk at the time. I think it really helped my mind just organize the risk. It just felt like, "Okay. Why not? Let's do it. Why not me? Why not now? Why not buy this? Let's try this." It's [inaudible 00:04:43]


Shantel: That's amazing. Speaking of the risk factor ... I imagine being surrounded by inspiring women was a big factor in allowing you to do that. But, did you grow up around anyone else that inspired you to imagine more and become an entrepreneur, or, was that the pivot moment for you when you joined that first company?

Stacy: Yeah. No. That was a great question. I grew up around entrepreneurs. Both of my parents have always worked for themselves. Always run their own businesses. Small family businesses that ... My parents have a roller skating rink and a bus company. They did ink cartridge or print it printer thing. My dad's family had a glass business way back when. So, I've always seen my family work for themselves. Work creatively. Take on new businesses. Set ... let other one's sale. Yes. I was exposed to entrepreneurship from birth basically. In general as I grew How He Asked I think that connecting with other entrepreneurs in phases ... In the exact phase you're in, but, then in phases and levels beyond what you think you're in or where you think your business is, is also very helpful. For me to balance of finding people who literally are trying to figure out accounting for their small business ... At the same time I talk to people who had sold five companies already was really important for me. To keep myself grounded, yet to also understand that I had this trajectory that I wanted to go down and other people had done it and they'd reached the end of the rainbow. It can be done.

Shantel: Being an entrepreneur is sometimes very lonely. Surrounding yourself with people who know things can certainly help you as you continue to grow and evolve. I want to unpack the sale a little bit. I think a lot of us either haven't been in that situation yet, or, are approaching an opportunity like that. Can you tell us about the resources or people you turn to when that conversation started to get brought up?


Stacy: Yeah. I ... The company who bought it is ... Most people know them as The Knot. Their parent company is a public company called XO Group. I worked with the organization for a few years. I'd cross paths multiple times with either editors or some of the sales team or their ad operations team and even the CEO. My husband was at a gala and someone said, "You remind me of this guy so much." It turned out that he was the CEO of The Knot. Point being I had had a relationship with them in many different ways over the years. The conversation about the acquisition came at a point where I had thought about it many times. I think they had likely thought the partnership would be a good idea. So, really I had educated myself the whole way through. How do I structure our first partnership such that it wouldn't limit me from future partnerships with them, future acquisitions, whatever it may be? I really had to open up my books and the people and my resources really early on. I just found people who had done advertising partnerships, revenue shared deals. I was close with the CEO from the company that I used to work with. I would constantly pick her brain on these types of things. I really just went to anyone who had had similar experiences in completely different businesses so that I could set myself up with the scenarios that I might face. I think one of the things that ... I think the word entrepreneur ... One of the biggest traits of an entrepreneur is that you tackle firsts and fears. I had never done what I ... Most of the things that I did with How He Asked, I had never done them before. Now, maybe when I start a second company I'll have less first. Right? I'll know how to set up ... I keep saying an accounting. It's such a pain point for me. I'll know how to set up my books from day one. I will know what legal paperwork to have in place before I start having certain conversations. So, sure. But, going back to my first business, I think a lot of the conversations, and the things we're doing are firsts for everyone. Just to be able ... And that creates fear. Right? Because if you don't know what you are doing. You automatically think fear. But, the truth is maybe you haven't done, but, someone else has done it. If you can find someone else whose done it and have them experience share with you, then you can just sort of see yourself in that situation. See someone else in that situation and just have this confidence that, "Okay. Someone else has done it. Why wouldn't I be able to do it?" Or, "I might have questions and that's okay, so did this person." I think asking for help ... Especially in really specific situations can really help alleviate ... Or at least it did for me. Alleviate a lot of those, "Oo, can I do this? Oo, am I going to mess up? Oo how do I say this?" You really just learn how to say those things. You learn what the situation might look like and you go into it.

Shantel: I think that's great. Speaking on that a little bit, did you always know you wanted to scale and sell the business? Or, be acquired? Or, was it something that evolved over time and it switched from lifestyle. And, if so, when did that moment happen for you?

Stacy: Yeah. That's a really great question. And, truthfully I went back and forth a lot on that. I enjoyed growing the business. I had a few people on my team who I really loved getting to know and really loved them supporting a business and me supporting their growth. That dependency together was really meaningful to me. But, at the same time there was a point where I knew that I didn't want to build the company past where it had been. Or, that I didn't want to take on new verticals. I knew that there would be an end point for me and for the company. Again, I knew it was my first company. I knew there'd be more. As much as I loved the brand and what my small team were building and how we were doing it, I did feel like there would be a tipping point. Truthfully the tipping point came at the perfect time. Because, the brand had tons and tons of growth which, really excited me. I felt since we had reached a level of traction out there in the market, that then I was suited to be under another umbrella company that ... The types of partnerships that we were doing with our advertisers, the types of scale that our traffic was grown into, we got up to snuff. For lack of a better word. Thankfully, we became appealing to another company. Just the maturity of our own company. And, again, the types of things that we were working on matched a lot of the same things that other bigger, larger companies work for. Really, again, I'll go back to that sweet spot word. I did go back and forth on what I cared about or what I wanted to do with the company. But, we reached this point that was perfect. I think on the other end at the table for XO Group, they had seen the same thing. So, really it was the sweet spot and seamless turning point for the company. That's when I had all the confidence in the world that this was the right decision.

Shantel: I think that's great. And, a true testament to what you've built. Kudos to you.

Stacy: Oh. Well, thank you.

Shantel: You're welcome. Is there anything looking back that you know today that you wished you would have known when you started How He Asked? Or, during the sales process?


Stacy: Yeah. Gosh. That's a good question. There are so many things. I think the biggest thing for me is that when you are building something with ... You have this drive to you and this excitement. You're feeling is like, "Just go. Just go. Keep moving, Keep moving." I would 75% continue to support that belief. But, because of my experiences there's that other chunk of me that says, "Take a minute to slow down. Make sure that you have all of your mission statement, your finances, any of your legal entity ... Have everything figured out. Take good notes on the steps that you take."  One, if you ever need to go back and reference these things ... If you're selling the company. You have it on record. And, two, it really helps you understand your business better. To keep track of what worked and what didn't work. In a way that you can visually see. Because, in my case I could sit here and think through things that worked and didn't work. Or, things that I wish I did more of, or, I wish I did less of. But, in the moment right now I feel like, " Oh no. It all worked great." You sort of forget what actually happened. I think what actually happened are the lessons that can cause you to grow faster, stronger in your next phase and so on. I think what I'm trying to say is take record of more things in the beginning so that you can really use your experiences as hard learning lessons and not just memories of craziness.

Shantel: What would you think would be the biggest mistake that you've made as an entrepreneur so far?

Stacy: I think there's two things that I could have been better at. One of them was tracking. Whether that's keeping the best record of finances, or, whether it's like I was saying before, just understanding what happened to the business, why that happened when it happened and calling out learnings from that. I think being strategic and having plans around where I was and where I was going, that's something that I didn't do enough of. I think I relied a little too much on serendipity and this mentality of, "If you just do it, it will come." I believe in that. I really do. I think going forward into my next endeavor, having a solid foundation even in the early days and early months is really important. I think taking the time to say to yourself, "Hold on. Let me get things in order here. Let me write down my mission. Let me write down my values. Let me really go through some of these core parts of the business that in a year you can go back to and check yourself on." Or, in two years or in five years you can go back on it and see, "How am I doing here?" I think that foundation can be really helpful to just keep your mind on track. To keep your business, the physical business that's sellable one day, right in order. That was definitely a mistake of mine. The second mistake I think ... At a certain point you limit yourself to what you know. As an entrepreneur, as a business owner, you can very easily get consumed by what you're doing. A lot of people work from 9 to 5 at another job. They clock in, clock out for all intents and purposes. They come home and they can separate themselves. But, if I can open up my work, my line of business from anywhere and it behooves me to work harder and it behooves me to continue growing something, why wouldn't I open my laptop at 9:00 PM? Because of that, I think my mind was constantly focused on my business, my business, my business. And, yes, I sought out mentors. I listened to tons of podcasts and other inspirational speakers and motivators to get me going. But, I still kept my knowledge very limited. Very much to content, digital media and whatnot. I think that one ... I don't know if it's a mistake or just now I know and now I see the importance of it, but just learning about other industries. Figuring out what self driving cars are doing. Right? Yes it has no application to How He Asked, but, perhaps there's a technology that sparks an idea in my own idea. I think you can just never get enough of outside industry learning and even studying psychology, body language, things like that can all help you more than you know. The take away here is to don't limit yourself to just the industry that you're in and knowing everything about that, but, to also branch out.

Shantel: As an entrepreneur I think always learning and growing is extremely important. On that note, outside of podcasts and books, are there anyplace that you go to find inspiration? From a morning run? Or, do you read certain journals and articles? Where do you go for that source?


Stacy: I think two things. That's a really good question. One thing I do, or, I have been noticing helps more and more is actually just alone and quiet time for me. A lot of the ... Like I said before, you can get so in your mind and committed to the day to day of your business and making sure that everything's working that you don't take enough alone time, or, quiet time. To actually sit and let your mind unwind and let your mind ... Not unwind like just breathe in and breathe out, but, truly release all of the ideas and excitement in the things that came to you in that day. Just let go of the waste. Really, if I sit in silence, or, if ... I have a dog, I take her for a walk. I don't bring my cell phone. I don't listen to any podcast or bring any outside distractions. I just let any of the waste and thoughts and energy just leave me. Then I get left with the core "aha" moment of my day. That's where I can then plan for the next day. I think, to answer that question, it's looking inward to find some of that knowledge and that guidance. It's becoming more obvious that a lot of my intuition can lead me into a good place if I give it time to process itself. Aside from looking inwards, I would say, I do a lot of ... I'm a very social person. I love hearing other people's stories. Whether that's listening to podcasts or going to a happy hour, a meet up group or calling a friend who's an entrepreneur and hearing their stories. To me story sharing and experience sharing is ... One, it allows me to relate to other people. Two, it allows me to see the ... I don't want to say struggles. But, it just allows me to see what other people are going through. It makes me feel less alone. Especially when you have a good, humbling conversation. I think you can just get a little more out of it verse constantly turning to these inspirational podcasts, or, inspirational speakers, or TED talks that sometimes are a little less tangible. For me, I like to really bring it down to actually finding a person I can have a conversation with and hear true things to learn from them and of their experiences. Even ask the hard questions, or the questions that maybe are less glamorous. At that point I can really get to an understanding of another person and how it can potentially ... What that can mean for me and my future.

Shantel: I love the concept of experience sharing and sharing stories. Because you learn so much from someone else and what they've been through. Even if it's not totally applicable to what you're going through right in that moment.

Stacy: Yeah. Absolutely.

Shantel: Let's talk about your day to day. How does it vary now verse when you owned the business outright and what does your day to day look like?

Stacy: Yeah. As I said before, my day to day when I owned it ... Yeah, I still have a lot of ownership in the company as in responsibility, accountability. I still care so much about it. But, actually owning the business it took over my whole life. Right? What is the meaning of this every single day? Will I sell it? Will I keep it? Will I grow it? What will I do with it? All of those questions surrounded my mind. Sometimes more than, "Hey how's my email inbox? Hey, did I ever get back to that advertiser with a creative idea?" Now, because I have been able to alleviate some of that entrepreneurial pressure, I can create a structure that to me it helps with some of the results and outcomes that come out of How He Asked.  On top of that, because I have a larger team and more resources and I'm just exposed to more minds and more people who are invested in the company, I have just been able to stretch How He Asked imagination and the things that we can and are doing a lot more by being part of a bigger company. I think there's ... As far as How He Asked, and the tasks I have to do for How He Asked, it's maintained itself pretty steadily. But, I think some of that emotional attachment has washed itself away, but, replaced with just a whole new experience that I'm less responsible for emotionally. If that makes sense? But, I still am invested just as much in.

Shantel: In addition to extra resources and brain power, are there any tools or techniques that you use daily to stay organized and to be inspired to imagine more?

Stacy: Well, I talk to myself all the time in the mirror.

Shantel: That is quite a beast of a tool.

Stacy: But, you're not surprised are you? Again, like I said earlier, sometimes some of the things that we do or don't do in our lives are because of ... I don't want to say self talk like the negative self talk. It's actually the opposite way. Right? So sometimes I'll wake up and say, "Oh, my body's killing me for some reason. I don't want to get up. I don't want to do this. Yada, yada, yada." And, the only way to get myself out of that is to talk to myself. Right? You have to shut those thoughts down and say, "No. Today's a great day. The weather's looking wonderful. You have yoga scheduled. You have these ... So, let's go." You have to sort of talk to yourself to push yourself out.  Unless you're crazy and you just wake up every morning just running out the door to everything you have to do. I'm not like that. You have to talk to yourself. When I think of talking to myself in situations like that, why wouldn't I want to also talk myself through some of the big pieces of business, or, some of the big conversations that I have to have? When I was going through the acquisition process, I'd never had even close to the level of conversation that I was having in these meetings. I don't think the word was scared, but, I had just never done it.  There was a lot riding on these conversations. A lot ... there was a lot of my business that I had to express. There was a lot of myself I had to express. When I talk to myself and just tell myself, "You got this. You know your business. If you want to practice in front of the mirror with me right now, I can listen to you." You really can get a lot out that's inside of you. That helps organize some of the crazy clutter that just goes on in your mind. I'm sort of assuming that everyone has a crazy mind like me. But, if you're listening to a podcast and want to learn more about yourself, you're probably not too far from that. So the tool for me is talking to myself in the mirror. Asking myself, "What's the meaning in this?" Why do I do this? How can I create success in this situation?" So, there's that and then I make lists for myself every single day. I have a list of work items, household items, happiness items. I travel a lot so I probably have a trip to plan on the right. I really keep a lot of lists and columns. That really helps me tackle things. Whether they're like big things that I want to do or just a grocery list. Again, it keeps my mind in check when it otherwise is just running a thousand miles a minute.

Shantel: Self talk and affirmations and just positivity is important. Especially when you're faced with some of the tough things that happen in business. I think that's great.

Stacy: I agree with you. Yeah. No. I definitely agree with you. I think there are some things that ... I have a handful of those entrepreneur friends that I speak to on a regular basis and it's funny I sometimes will compare some of their tactics to mine and say, "Gosh. That person's so organized." Or, "Gosh that person's never missed a beat." Or, "I'm kind of shocked to hear they've never done that."  I think the self talk part for me can help weed through the good and bad for me. If I have a conversation with someone and I feel either impressed by an idea or something just really resonates with me, then I remind myself of that. Then I can include it in my life a little bit more. Then if there's something that happened that I don't agree with or that I wouldn't add to my tool kit, in the moment, because I am speaking to someone who I respect, I might feel like, "Oh gosh. I don't do that and they do." But, then if I can talk to myself later and just decompress it all, I can say to myself, "You know what. That's not for me." Again, I think you're constantly hearing thoughts, advice, things you should do, things you shouldn't do, tools to use and whatnot. I really think that obviously explore them all, but, in the end if it works for you, you'll use it and you'll know. If it doesn't work for you, when you start to use it you just ... If it's not natural or if it doesn't actually solve the problems that you're trying to tackle, it's okay to walk away from them. Because it doesn't work for you and it worked for someone else, it's fine. I have to remind myself of those things sometimes.

Shantel: Yeah. I mean the world is polluted with a lot of things you should be doing and could be doing and I think it's great that you have that perspective and you can take a step back and think though it on your own.

Stacy: Yeah. Oh, yeah.


Shantel: Speaking of experience sharing, what is the most valuable piece of advice you've ever received?

Stacy: Oh my goodness. I've ever received? Oh my gosh. I give a lot of advice, but, no. Oh my gosh this is so hard for me. No. I received a piece of advice ... It's not that hard actually. It was actually the first piece of advice I ever received from a boss. It was the first week at my first job in New York at a start up. I remember feeling really excited because I found something on the website that was broken, or something that read wrong or didn't connect or whatever it was. I remember running to my boss saying, "I found something, I found something. Look. Look. Look." It was a good problem to find. Yes. No one had found it. Great. But, my boss said to me in the kindest way, "Never ever, ever, ever come to me with a problem. Come to me with a solution to the problem and we'll go from there." That was really impactful. Because, first of all it guided my journey as an employee for the next two years. I felt like it really made a difference. I remember giving that piece of advice to one of my first employees. It's so funny because about a year ago I reached out to her and asked her ... I just asked her if she had any feedback on our experience together, this and that. She said the biggest pieces of advice she ever received ... Or, the best, I should say, was the same advice that I was given. Because, on her first week, which I didn't even realize, I guess she had come with a problem that wasn't solved and she said, "From then on." For me that was a really big piece of advice I received, because then I could pass it along as well. It just repeated itself in my life. Yeah. Don't come to your boss with a problem if you don't have a solution.

Shantel: I think that is powerful, powerful stuff.

Stacy: Right?

Shantel: Yeah. I mean I think it empowers people. It allows people to flex thinking out of the box. I think that's great.

Stacy: I know at ... With Imagine, you guys are ... You have a big team of very creative people. I think ideas can fly left and right. Do you have that same experience of needing to walk this balance of, I want to hear what's going on in the field? But, I also want you to tell me what the solution is and not just come to me with, "Oh there's too many people doing this. What should we do? You know what I mean, I'm sure.

Shantel: I mean I'm finding that the team has amazing ideas and oftentimes they're far better than the solution that I would have come up with. I think it's finding a balance of empowering them to voice that and not be afraid to come with a different idea. Absolutely. It's important for people to feel ownership over the projects they're working on so they don't just become a cog in the wheel. I think that's great.

Stacy: Yeah. And, I think that's what I felt. That's such a good point. When he ... I didn't feel scolded when he said it to me. I actually felt respected. Because I felt like, "Oh. You don't want me to be just a whistle blower, you want me to be a problem solver." That really changed the game for me. I think creating a culture like that even for yourself or for a bigger company that you run is really important. It made a huge difference.

Shantel: Absolutely. Well, I appreciate you sharing that. What is next on the horizon for you?

Stacy: Oh gosh. Well, I am still working with How He Asked and XO Group. The most entrepreneur ... Not most, I would say a good chunk of entrepreneurs will do some sort of ... What do you call it? Like a transition of sorts and we're still going through that. I really enjoy working with them. It's giving me a whole different perspective. For me learning to bridge my excitability and, "Oo, let's do everything yesterday. With some structure and some protocol and little bit of a different hierarchy." It's actually given me exposure to something that ... My team was three or so people. We were very small and close knit and had this open forum where truthfully, anything could get done yesterday. Now, I'm moving into just seeing the mechanics of a larger organization and how successful ... How to reap success in that environment is really helpful to me. But, I also am starting a non profit. It's sort of in the works. Essentially it's a way for people to share kind, motivating, uplifting and positive things with people they care about. They sort of do it anonymously. I should use air quotes, "anonymously". When the recipient receives the message, they can read it, they see all the fields and they can likely guess who it's from. But, to really unlock who the sender was, they can either donate to a charity of their choice or they can "say it forward." Say it forward means to send something kind to someone else. Again, it's in the early stages, but, that's the general premise and I'm super excited.  Other than that, I'm kind of laying low, hanging with my dog and working a big job.

Shantel: Nice. Well, I'm excited to have you back to hear more about the non profit as that gets going.

Stacy: Oh. Well, thanks.

Shantel: Thank you so much for spending some time with us and talking through what makes you imagine more.

Stacy: Oh. Yeah. Absolutely. Thank you so much. Your questions were all really great, and I love being part of your journey. Thank you for having me.