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We’re a tribe of proud dreamers at heymama. We’re always working towards bettering our businesses and ourselves as we chase that one thing we’re all seeking: success. While we dream big and have goals that we have our sights set on, what is often more difficult for us to discuss (and sometimes accept) is an inevitable part of this journey: failure. Mama to one, Diane Loviglio is a seasoned start-up professional and founder of Boon + Gable who became interested in normalizing this missing part of the “success” conversation in her early start-up days when she started chatting with other founders in her circle and discovered that they all had one thing in common: they had all struggled somehow on the road to success. With this revelation on her mind, Diane then helped to co-find FailCon, a conference devoted to openly discussing failure and changing the way we talk about those unforeseen obstacles in our business and personal pursuits. Here, Loviglio gets “real” about failure and success, and why finding a squad — and a healthy dose of humor — are key to getting us through tough times. Read on…

What is your professional background like? What did you do before creating Boon + Gable? What need in the market did you see?

I started Boon + Gable from the frustration that I had while shopping. I would go to stores and sometimes ask for help, sometimes not, but would always come out of the store empty-handed or having bought the same thing I already had at home, and I felt really frustrated. So that’s where the idea came from, and it’s my second start-up. My first was in the clean energy space, and I actually went to school for Architecture and Anthropology, so it’s pretty different. But I did go to a tech-school at Carnegie Mellon.

You co-founded a conference called FailCon in an effort to normalize this phenomenon we call “failure,” and to help people realize that even the most established businessmen and women have had their fair share of obstacles while climbing the ladder of success. Can you tell us about how and why you started the conference?

I had just moved out to San Francisco from Pittsburgh, Pennsylvania, and I started my first company in the clean energy space. I had never had a start-up before, as I was fresh out of college. My co-founder, Kurt Brown, had founded two start-up’s before. He had a Computer Science PhD and had done a lot of different start-ups so he knew all about the start-up thing, but me being new to it, I wanted to learn from a lot of other people, especially those in Silicon Valley — that’s where we were. I wanted to make sure that I didn’t make the common mistakes as a newbie start-up founder. So I would talk to this person, and then get coffee with her, and then jump on a phone call with him. I was talking to all these people and I was like, “These stories are amazing, like oh my gosh! Their experiences are such a wealth of knowledge.” Then, I was like, Well, I’m not a blogger, but I want to get this information out there. What’s the best thing I could do? I could write a blog, but that’s just me alone in front of the computer. I thought, What if we just had a one-day event where people just felt like it was okay to talk about these failures, because a lot of startup founders have a lot of anxiety around that. What is going to get these stories out there?

The cool part about FailCon is that it was a very uplifting day, like “Damn, good for her! It’s amazing that they got through that,” and “Oh, they’re also struggling.” It was positive and reassuring. So we did it for a couple of years, and then I started it with another girl who was doing events, and she took the conference international; she went to Brazil and whole bunch of other places. Everyone was reaching out saying, “Woah, we need this in our city!” And we were like, “Oh, we’re not getting paid! We’re just doing this for the good of the community!”

Talk about failure

“We felt like failure was taboo when we started [FailCon]. Now, we talk about failure and we can actually say the word out loud.”

We think failure is important for us to talk about because, more often than not, struggles precede great successes. Do you think we’re getting better at talking about failure in modern day society? Do you think we’re getting more “real” about what the road to success actually looks like?

Honestly, we’re totally getting more real. I think failure is still the worst thing that can happen to you [laughs]. It’s scary, you don’t want to talk about it, you don’t want to face it, but you can come out of it being like, “It’s not that bad.” But I do think we’re better at talking about it than we were before. Now I feel like people brag about their failures, which isn’t the right response either. Anyways, we felt like failure was taboo when we started [FailCon]. Now, we talk about failure and we can actually say the word out loud. The issues don’t have to last forever. And so, we haven’t produced a FailCon show in like eight years. But it’s an initiative that really resonated with people. NPR came and supported us and called it “a breath of fresh air.”

Can you name a few people that have been featured at the FailCon conferences?

Travis Kalanick from Uber! Which is super interesting, because at the time, it was still called “Uber Car” and I didn’t even have the app. People weren’t even using it — it was so, so early. Like it was still a thing, but not everyone was using it at all. And in Travis’ history, he talked a little bit about Uber, but he also talked about how all the companies he had started beforehand didn’t really work out for him — Uber wasn’t the first time he was a founder.

We had Joe Gebbia, one of the co-founders of Airbnb come talk. Their talks were pretty classic — like there was a time when they were really, really down, and they were like, “Oh, this isn’t going to work.” So they kind of just talked about their struggles, just like showing the graph of how things dropped, and then how things eventually started to take off. I just remember their PR people being like, “But we’re not going to talk about anything else, okay?” The PR people were so afraid to talk about failure. But now, I’m sure they would be like, “Sure, sure, sure!” So some of these people are really hard to get, and others told us “no”. They were like, “Yes I’ve failed, but there is no way that I am going to talk about that publicly.”

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What tips would you give to a businesswomen who’s hit a rough patch? What is a healthier way to view “failure” instead of considering it a “defeat”?

I think the best thing is just to find your squad. I think it’s about finding people online, finding them in person, getting coffee with one, going to groups, and talking about things that are both working and not working — just knowing that you’re not alone. That’s the most useful. And knowing that there isn’t an easy pass and there’s no right answer. If there was a right answer, we’d all be shouting it! I talk a lot about how startups are similar to babies, and this was before I had a kiddo. I think in the parent community, everyone is very accepting of the idea that your second parenting experience is different from your first — like no two are the same. And that’s exactly true for startups, but I don’t think the startup community is there yet. I think the startup community is definitely still like, “There’s a pattern of recognition! If you didn’t do that, then you’re going down. And you shouldn’t take this path,” etc. I truly believe that there is no right way. So Kurt like, he got lucky. Yes, they all did great stuff, but they also got lucky. I think the same follows for parenthood. We have an amazing three year-old daughter, and she’s like really well-behaved. I think we just got lucky. For a while, I thought it was all about the parents, and now, I’m like, “Nope, we just got lucky!” [laughs]. 
FailCon co-founder Diane Loviglio with her husband and daughter

Can you share a personal failure that you learned a lot from? What was that experience like?

I don’t know if I have one mentor or that “one experience that changed the whole world”. Being a second time startup founder has given me a lot of confidence and strength, in terms of like, “Oh, yeah, I’ve seen that,” or “Oh, that’s the way it is. Don’t crazy on that. That’s actually normal even though it doesn’t feel normal.” Your second company is different from your first like I was just saying. So going through that before has helped a lot. I remember as a little kid, I was playing in a piano recital — the only piano recital I had ever been in — and I knew this song by heart. I think I still brought up my sheet music with me, but suddenly, during it, I just screwed up. I froze. I couldn’t get back into it. I started again and got through it, but during those few moments, I was just staring at the piano and feeling everyone staring at me, and I was like Whoa. And I remember my dad saying afterwards to me, “You did the best you could.” I don’t know, I was like six, or 10! But now, if I ever fail on the piano, I already know what that’s like — I’ve already done that! It’s kind of just like practice too, right? Like, I’ve already done that path, and something else could happen, but I’ve already done that.

What do you do when faced with an imminent failure? How do you turn that into a positive experience or “teachable moment”?

I try to laugh it off, honestly. That’s how I respond to the Trump presidency like, “What did he just do? Okay, stop! Like, what is happening?” I kind of like to use jokes, even if it’s some nervous laughter. It’s a coping strategy!

How do you talk about “failure” with your little one? How would you approach a conversation about unforeseen obstacles with them either now or in the future?

Yeah, we just want her to never think that she can’t do something. We don’t want her to block herself. She says, “I can’t,” a little bit, and it worries me a little, but I think it might just be a phase. But I say to her, “Why do you say that? Of course you can!” Just to make sure she doesn’t talk herself out of it. We’re just like, “Actually, we think you can. Why don’t we talk that through?”

You’re very much into volunteering and we love that! What causes do you hold near and dear to your heart, and why are they important to you?

Growing up and going to school for architecture, I did a lot of work with Habitat for Humanity. Then, when I first moved out here and doing my first start-ups, I was volunteering at a underserved public school that was only a few blocks away. Now with kids, it’s definitely different for sure. We are trying to think of things we can do with her to involve her. As a company, we volunteer at the local food bank. During Hurricane Harvey, we just packed up a whole bunch of things for those impacted, including diapers for like a diaper bank. I’m not sure she’ll ever remember helping with that, but instead of just doing that alone, we did that altogether and got her involved. One day down the road maybe we’ll have a conversation about it, I don’t know, but just being able to have her own that I think is important.

3 pearls of wisdom


Family dinner time. Trying to make that a norm is important to us.


Keep your phone at home sometimes. Take in the outdoors. Look at things you don’t normally look at. Doodle.


Know that others are struggling, especially working mamas like us. Know that you’re not alone!

xx Diane Loviglio
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