Cassie Phillipps, FailCon: Failure is the Best Way to Learn How to Succeed

Video interview with Cassandra Phillipps, Executive Producer FailCon

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Video interview with Cassandra Phillipps, Executive Producer FailCon.  Cassandra has been a startup event producer for over three years, producing and managing numerous conferences, including FailCon, SF MusicTech Summit, Inside Social Apps, Unleashed Conference, Startup Seminars, and many more. She works with clients to insure each has a high-quality and profitable event, connecting them with the best partners, sponsors, and speakers for their topics. Before moving to the start-up industry, she served as a stage manager at various theaters around the country, including the American Conservatory Theater, Chicago Court, Marin Theater Company, and Aurora. Cassandra has a B.A in Human Development from the University of Chicago. You can find Cassandra on her blog & on Twitter @webwallflower 

  • I was wondering if you could tell me a bit about your story about how you started the FailCon Conferences?

Sure I’ve been doing events in the startup community now for about 4 years. I started in 2007. Our first events were on the facebook platform which had launched in, I believe July 2007. Through that clientel we started to do events for the startup community as whole for early stage founders. Around that time I started developing my own startup which we called Trogger. Long story short we worked on it for about 9 months & it failed. We spent about $80,000 of our own dollars on it. I still think it was a neat idea but we just didn’t execute it well. While we were working on it, I was attending & producing conferences to make some money on the side. I realized very quickly that I was getting bored at these shows. I was getting bored at my own shows. I realized that the reason was was that I could be inspired by the speakers on stage but I couldn’t take their story & apply it directly to my startup. They could tell me exactly what they did & exactly how they got to that successful point but because I didn’t know the same people, I didn’t have the same funding, it wasn’t the same market, I couldn’t do that! I would have rathered heard ‘well we made these early hiring mistakes that didn’t work out so lesson learned’ or ‘well we didn’t iterate fast enough, we lost a lot of money in the beginning so that was really hard.’ Those were lessons that I could actually take & say ok don’t do that! At least eliminate those things! So from that FailCon started. That was back in February 2009 & from there it’s just grown. It started off it was going to be a half day evening seminar & everyone seemed to love the idea. They said yeah I do want more events like that that are telling me well don’t do this, don’t do that & getting really respected & really successful people on stage to say heh, I wasn’t always successful, here’s kind of the mistakes I’ve made. And the shows just really taken off!

Fabulous! I know that the thing that prompted my project was my own failure at raising venture after 5 years in London. So I can be definitely reassured that that definitely is a huge motivating factor! That you would do things you wouldn’t normally do & step outside of your own comfort zone & step outside of your own reality I guess to look at new ways of doing things! So it’s extremely valuable.

  • What would you say that people get most out of your conferences?

I would say & it kind of follows up on what you just mentioned, is looking at someone who is successful & seeing in them that they weren’t always successful. Seeing that they maybe had to mortgage their home or one of them was separated from his wife a while or had to declare bankruptcy. And they were where you are now or even lower, losing homes, losing apartments & they bounced back. They had these stories of ‘listen, once you get as low as you can get, suddenly getting higher again isn’t so hard. You realize that if that’s really as bad as I can get, well why not try again? If that’s the worse I could have? I think a lot of founders come away with both a realistic approach to what a startup is going to be like, that it’s not just these great successes. Don’t think that’s what it is: you just make a product & bam it’s really popular! But they also come away with this idea that ‘Hey I can do this & it will be really hard but these successful people started where I started & it makes that a little more tangible. It gives me & other attendees more actionable things that we can start with.

  • So it sounds like the stories are what inflame & empassion the attendees? Is that correct?

It certainly seems that way. People do ask for a mix (& I try to do this) have one or 2 speakers that are just telling their stories (those seem to be the most inspiring things). I also try to have a few workshop sessions that are what can you do right now early on to stop a failure that you’re encountering or to prevent it down the road. So there not all just stories, some of them are very actionable goals. But I do try to shelve it, like bookend it, with 2 really good stories.

  • I know you actually had a startup you were mentioning, which failed unfortunately. I wondered if you could give any tips to women who may be currently thinking about or actually doing it – raising venture or angel capital?

Sure my lessons are predominantly for web apps. (I don’t have very good advice for building the next biotech company) But my number one piece of advise for anyone working on the web & looking to raise funding for a web app or any sort of online tool, B2B or B2C, is Start with you Minimum Viable Product. The Lean Startup movement is about this & some close colleagues of mine had the same idea. Don’t try to build a huge product with 10 different features because you think they’re all cool. You’ll just never get anywhere, you’ll never be able to launch anything, you’ll be stumbling, you’ll be spending a lot of money & by the time you do release it, you’ve never tested it. You don’t even know if your customers want it. Elizabeth Yin has a great story with her past startup, where it failed for that reason. Now she’s launching something that is literally her product when she launched was some emails between friends. It was this whole idea that she could sell advertising for them. Ok great so you’ve talked to her? It’s this idea that now she’s raising funding for that. She’s a very simple one page website & as she figures out how her clients are using it & what sort of things they’re asking for she’s slowly tacking on things.

Yes it’s a very inspiring story!

Yeah & that was our biggest mistake. We kept trying to build this startup & launch it with leaderboards & points & comment threads & status symbols & website integration & facebook integration & viability. Then we launched it after 6 months of working on it & $70,000 spent & everyone said ‘I don’t really get it! I don’t really get what I’m supposed to do with it!’ And we didn’t have any time left to fix it! So that’s my number one piece of advice: launch something small really, really early then fix it as you go along!

That’s my advice too so it must come out of failure!

Yeah, yeah it seems to be the biggest mistake that every first time founder makes, trying to launch something really cool right away rather than something really small & simple (even if it’s not getting press) it’s ok just test it slowly & build up!

  • The big element really is to go where the demand is, rather than try to supplant your own ideas on top of people!

Yes we also did that too. We kept having our users say I don’t get it! And we would say ‘Well you’re not the target audience! We’ll find a new target audience!’ Bad idea!

Things we do! Well thank you very much.

  • Would you have experienced any bias for women who have been trying to raise capital at all yourself or heard stories about that?

I personally when I was talking to vcs, didn’t feel any bias. That could have been because I was young & clearly not at the family age which tends to be the bias. I was 23, obviously single, obviously not having babies anytime soon. I certainly could find stories but I don’t have them immediately any off the top of my head! The great one was Jessica Jackley, Profounder who was having twins & her actual investor writing a blog post ‘I’m nervous that she is having twins, I wouldn’t be if she was a man or wife was having twins!’ I was actually upset with people who got very angry at him, because he wasn’t attacking her, he was saying ‘Community I understand that this is not right, that this is not a good thought for me to have but tell me why I shouldn’t have it.’ And I hated the people that said because you’re a jerk! That’s not fixing this industry. So that’s a famous story of that bias!

Thanks so much for your time today, I really appreciated your feedback. I’m looking forward to the FailCon.

Thank you, I hope to see you there!

Written by
Pemo Theodore

Pemo Theodore is a Media Publisher and a great people connector. She was Founder Silicon Valley TV which served the San Francisco Bay Area for 10 years! She has produced Silicon Valley Events for Investors & Startups for 10 years. Pemo loves to video interview venture capitalists & founders to engage the human behind the success stories.. She has been Executive Producer of FinTech Silicon Valley for 6 years, organizing twice monthly FinTech talks & panels in San Francisco & Palo Alto and audio podcasts. She believes in learning through a great discussion with experts in the domains. Pemo has a talent to bring the right people together and is an incredible networker. Pemo's events have been seen as supporting Venture Capitalists & Angels in sourcing great deal flow from startups who attend her events. Many founders have received funding through meeting investors at her events. Her favored medium is audio & visual media and she has built up a great body of work of videos of panels & interviews and podcasts in Silicon Valley startup ecosystem. She has lived & worked in Canada, Australia, New Zealand, Ireland, London, Northern Ireland & Silicon Valley. Bio

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Written by Pemo Theodore