speaking logos - grayscale

“It was such a pleasure to have Willo kick off DATA2014 with her inspirational ideas! Her unique and creative perspective really fed the minds and hearts of our crowd. She is a game-changer... and a life-changer! We love Willo!”
- Kim Chestney Harvey, The Creative Technology Network

For a list of my current topics, or to inquire about my availability for customizing a talk
or workshop specifically for your event, please contact me.

Speaking & Events

Opening Keynote at DATA 2014: Design, Art and Tech Awards

I’m thrilled to announce I will be delivering the opening keynote at DATA2014; a summit that epitomizes the work I do celebrating creativity and innovation!

DATA2014Design, Art + Technology Awards
Interactive Exhibition and Creative Technologies Summit
May 7-8, 2014 ~ Pittsburgh, PA

DATA 2014 is a national celebration of creative technologies in Pittsburgh, PA.

Founded at the intersection of Design, Art and Technology, this two-day event is an opportunity to engage with folks from all around the country on the newest trends in creativity and innovation. DATA is an event like no other — a mash-up of networking, interactivity and new ideas — showcasing the year’s most innovative art and technology projects, experiments and achievements.

The DATA conference brings together artists, entrepreneurs, geeks, investors, makers, innovation leaders, students and regular ole folk to be inspired by each other, discover new opportunities, and find out what’s next. Topics span the creative tech gamut, including design, gaming, film & television, robotics, mobile applications, education, edutainment, new media advertising, industrial design, architecture, animation, social networks, music, fine art, and much more. This day-long think tank is packed full of workshops, panels and talks on the newest and most exciting innovations and ideas!

This is going to be an incredible event! I recently discovered Penelope Trunk of Brazen Careerist will be speaking, too. I’ve known of her work for a long time, and am looking forward to seeing her keynote.

If you’ll be at DATA2014, please find me – or send me a tweet @WilloLovesYou – and say hello!

UPDATE: A short documentary video, and a few photos!

DATA2014 DATA2014


Click here to view more >

My talk was focused on how we are rapidly evolving individuals, we must develop compassion & courage to birth our big ideas into the world!

Don_t get tsunami_d by the fear


Also! Audrey Russo, the President and CEO of the Pittsburgh Technology Council, and I were also on an episode of Our Region’s Business while I was there:

Our Region_s Business

Pittsburgh is awesome!

Portland-bound for Pioneer Nation! #pdxpioneer

I’m thrilled to be contributing (a keynote) at the inaugural Pioneer Nation!

Pioneer Nation

March 26-28, 2014
Portland, Oregon

The world is changing as more people choose to work for themselves. We’re inviting independent entrepreneurs, small business owners, and freelancers to join us for an all-new adventure.

Put on by my friend Chris Guillebeau — who’s pioneered several amazing books and the World Domination Summit (WDS) — Pioneer Nation is specifically designed for creative entrepreneurs, small business owners, and freelancers. YES! That’s my jam.

Pioneer Nation

I work with Creative Entrepreneurs and passionate individuals who want to thrive in all areas of their lives. This means that our work starts with Clarifying their Vision & Goals, and then often translates into my supporting them with the tech and business aspects; effectively helping them take their creative ideas to the next level. These principles will be at the core of my keynote, and I’m super excited to see what fun conversations are ignited as a result!

Portland is also one of my favorite towns, too, so I’m stoked to be back there; surrounded by Badass Activators & Conscious Creators.

If you’ll be in Portland, I would love to connect with you! I love meeting new people, and have made so many incredible friends from WDS, that I know Pioneer Nation will be just as amazing in that regard. Can’t wait!

Please find me — or send me a tweet @WilloLovesYou — and say hello!

Hugs & high-fives,

UPDATE: Pioneer Nation was so much fun! Below you’ll find few fun tweets & photos from my talk. Video should be up soon, too!

UPDATE 2: The video has been posted! Click here to watch it AND get a free download of my Systems to Support you & your business!

Embodied Leadership: Practical Tools for Tangible Change [ Microsoft Workshop ]

Embodied Leadership = How you’re showing up

Microsoft Willo
Delivering my talk/workshop, “Embodied Leadership: Practical Tools for Tangible Change,” at Microsoft’s ‘Make it Happen’ Career Conference

How are YOU showing up in your life?

I do Heart-Centered Coaching. I work with Creative Entrepreneurs and passionate individuals who want to thrive in all areas of their lives.

This means that my work starts with Clarifying their Vision & Goals, and then often translates into supporting them with the tech and business aspects; effectively helping them take their creative ideas to the next level.

So, while I’m coaching & consulting, we’re not just looking at the tasks and to-do lists, but we’re going deeper, and looking at all the aspects that are going to enable us to BECOME and CREATE what we want to see in our lives.

What does being a Leader look like for YOU?

Leadership in your life doesn’t have to mean leading teams, or becoming the CEO. It’s about TAKING THE LEAD in your life.  Recognizing that you have a choice in how you CHOOSE TO SHOW UP.

It’s accepting 100% Responsibility for who we are now, and the willingness to get curious and discover where we may have room to grow.


Learning Edges = Opportunities for Growth

What are your learning edges? 

When we lean into our Learning Edges – our opportunities for growth – we’re opening ourselves up to more of what we want in our life.

Who you want to become starts with EMBODYING it today. Right here, right now.

A helpful framework for this can be to begin by looking at it holistically:

  • PHYSICAL: How we’re taking care of ourselves, our health, our bodies.
  • EMOTIONAL: How happy we are, and what our heart is saying.
  • MENTAL: How clear & focused our minds are. If we’re feeling lost or overwhelmed, and where we may need more structure.
  • SPIRITUAL: And lastly, how connected are we feeling. Are we clear on our purpose, and are we fully engaged; recognizing our actions are serving more than just us. We need to feel like we’re a part of something and making a difference.

What aspects of you/your life, if you gave it a little more intentional energy and focus, would greatly improve?

What’s the first step you will take?

Microsoft Website

Wednesday, March 26th, I delivered a talk/workshop, entitled “Embodied Leadership: Practical Tools for Tangible Change,” at Microsoft’s ‘Make it Happen’ Career Conference.

Sponsored by Silicon Valley Women at Microsoft, this conference supports professional and leadership development for Microsoft employees in the Bay Area. It focuses on insight and strategy to make ideal careers happen – YES! My favorite.

Thank you for having me, Microsoft!

Mentoring, speaking and supporting other awesome women!

I met Julie Ann Horvath at the Farmhouse Conference and she’s amazing! She’s not only a designer at GitHub, but she’s the Creator, Organizer & MC of Passion Projects; a monthly event where she invites badass women in tech to come in and share their awesomeness.

Passion Projects

Passion Projects

Tonight my good friend, Laura Gluhanich (aka @lauraglu) will be speaking on Your Presence Is A Present , and I’m looking forward to seeing her rock it.

Additionally… this weekend, Julie is putting on GitHub’s First Public Speaking Workshop For Women, and I’ve been invited to be a mentor/contributor!


I’ll be there, with several other (incredibly awesome and admirable) women, mentoring, working and hacking all day. We’ll be talking about things like writing a proposal and personal bio, writing in general, talk outlines and flows, how to handle Q&A or discussion formats, how to have (or fake) confidence whilst on stage, and how to show your passion.

I absolutely love what a champion Julie is for supporting women in the creative/tech industry, and I’m super excited to meet all the other rad women flying in from around the country for this awesome event!

Keynote Speaker: Women Entrepreneurship Retreat 2014

Women Entrepreneurship Retreat 2014

I’m thrilled to announce I will be delivering a keynote at the 3rd annual Women Entrepreneurship Retreat!

Friday, April 11 – Sunday, April 13, 2014
Ben Lomond, CA (near Santa Cruz, ~1.5hrs from SF)
Register Now

Capped at an intimate max of 55 rad women, this retreat is geared toward entrepreneurial women starting and/or running smaller organizations (this includes sole proprietors and freelancers).

This year’s theme is Guerilla Business Tactics for Women. Essentially, the art of doing more with less.

“Your competitors are bigger, better funded, and more established than you. That’s when you use every secret, hack, and shortcut you can get your hands on.

Among other things, we’ll talk about secrets for establishing credibility, covert tactics for getting access to the right people, and quick and dirty hacks for doing all sorts of thing you thought you had to pay big money for.

Each of the workshops and keynote talks will address a critical area of business, through the lens of guerrilla tactics. You’ll leave the weekend an empowered rebel, armed with unconventional tools and techniques that aren’t taught in business school. I bet you even have one or two tips of your own to share, don’t you?”

My keynote will be focused around a topic I help many of my coaching/consulting clients with, “Structure & Focus: Implementing Systems for Success.” I’m looking forward to learning and connecting with all the other amazing ladypreneurs there, too!

Join me at this beautiful retreat center in the mountains north of Santa Cruz.

Claim your spot & register now! 

MCing TEDxFidiWomen 2013

On December 5th, I was on stage for two big events.

The first of which is I had the honor of MCing TEDxFidiWomen 2013!

Willo MC Ignite MakeAStandLemonade

This is me introducing 9yr old speaker, Vivienne Harr, who has raised
over $100,000 with her Make A Stand Lemon Aid to help end child slavery!

I had first attended TEDxFidiWomen, in 2011, which synchronistically led to this post about Jennifer Sherman’s inspiring talk, my launching my “Ladypreneur: Women Winning at Work” tumblr, that was then featured in Glamour! Not to mention all of the amazing women I met, and whose words and wisdom impacted me that day.

One of them being the ever-awesome SARK, who I’d met & spent time with way back in ’97 (which is also when/how I met Andrea Scher!), and I was able to relay to her that – inspired by her bio in Creative Companion, that I read while I was living in Boulder – I too now “live in a Magic Cottage with my cat in San Francisco!” :p

The next TEDxFidiWomen I attended (2012), I contributed by designing an animated timeline of ‘Key Events in the Women’s Right’s Movement,’ that played throughout the day in the gallery:

TEDxFidiWomen timeline

As you can see, I’m a big fan, so I was honored to support and contribute again by MCing the event! All of the speakers were *amazing* (you can watch all of their talks here!), not the least of which was the fabulous 9-yo Vivienne who’s on stage with me in that photo above.

In fact, super cool is that I know Vivienne’s parents from way back before they were even married! We were friends in 1998, when Eric was speaking at the Learning Annex, and I was the Events Coordinator there. It was so awesome reconnecting with him & (his now wife!) Alex, and meet their super cool kiddos! So neat how life works that way, huh?

On December 5th I was not only on stage all day MC’ing TEDxFidiWomen, but after dinner I hopped in a cab & cruised over to the Brava Theatre where I hopped on stage and delivered my first Ignite talk! I’ll post about that, with the video of my talk, when it’s published. It was two exciting events in one jam-packed-with-awesome day!

I already have 4 exciting speaking events lined up this year, not to mention my own events/retreats (details coming soon!)… and, yes, I’m definitely planning on delivering my own talk at TEDx as well. Considering how much joy, knowledge and opportunity* they’ve brought my way, it’s about time, huh? :)

*In 2012 I also supported sweet Tanya Geisler by designing keynote slides to accompany her brilliant words of wisdom, and we’ve been working together ever since!

Big thanks & kudos to my awesome friends Michelle Fetsch & Gretchen Sweet, for putting on another great year, and here’s to an awesome year ahead!

Speaking at Farmhouse Conf 5: The Collapse of Hope & Letting Go of What Could Have Been

I had a last minute opportunity to speak at the 5th and final Farmhouse Conference:

Stories About The Collapse Under an Avocado Tree in Hollywood, California

Avocado treeThe famous avocado tree – massive, like a big green umbrella above us

Shane Becker, the organizer of Farmhouse Conf, attended YxYY event over the summer, so that’s how I’d met him and heard of Farmhouse. In fact, many LA and SF Yaysayers were in attendance, so it was an unexpected bonus to see & reunite with all of them!

Well versed in the heart-wrenching art of letting go, I contributed:

The Collapse of Hope & Letting Go of What Could Have Been

Launching our big ideas into the world takes courage & moxy. We dive in, our eyes twinkling with possibility and hope, and if we’re lucky we catalyze collaborators, supportive fans, customers and a community along the way. But what happens when you’ve lost that loving feeling? Or when you realize it’s time to let go of the baby you’ve put your blood, sweat & tears into and move on? Letting go of what could have been may just take more courage & moxy than getting the idea off the ground in the first place.

Willo speaking at Farmhouse 5Photo by  Tj Nelson Jr – view all

I shared how challenging it was for me initially to let go of my WilloToons line, and the challenges I’ve faced in taking big, bold leaps over the last few years (detailed here). All of which that has inspired my Connect video series, our ReConnect ecourse, my 1-Day Major Movement ‘Skydiving’ offering, and more.

I related the ‘collapse of hope’ to the letting go we experience in any relationship. That even if it’s best for all involved, there’s still a healthy amount of grieving and mourning that takes place.

I talked about the importance of recognizing that when we do let go, there’s always a thread that carries through; that we are never starting over. Which is much of what has inspired my latest offering, Harvest & Thrive.

Lastly, I shared that for us to really and truly move on, we must do the work to heal our hearts, so that we may be strong enough for the next big jump. We must go through a process of forgiveness and acceptance; of others as the case may be, but most importantly ourselves.

All of the talks were filmed, so I’ll be sure to update this post with the video when it’s available.

alexis farmhouse sketchLive sketch by Alexis Finch (aka @agentFin)
“Though we suffer the collapse of hope, we grieve & are resilient, so start again.”

The collapse, watercolor by Rachel Weidinger“the collapse does not need to enter your heart”
Watercolor by Rachel Weidinger

The entire day was amazing. I was delighted to meet/hang out with amazing folks, like fellow speaker, Nirvan Mullick, the filmmaker & hero behind Caine’s Arcade & the worldwide Cardboard Challenge; igniting entrepreneurship, play & imagination in kids everywhere!

nirvan willoThis is Nirvan’s original Fun Pass from Caine’s Arcade!
You must watch the video if you haven’t seen it yet.

Willo O'Brien & Jessica HischeMe with another fellow Farmhouse Conf speakers;
letterer, illustrator & designer, Jessica Hische

The entire conference went on late into the evening with fun performances by Mates of State & The Blue Ribbon Glee Club. It was a really fabulous day, and I was thrilled to have been a part!


Have you experienced a collapse of hope?
What have you had to let go of?

Share with us in the comments.

Celebrating the launch of Harvest & Thrive!

Today I am THRILLED to announce the launch of my most comprehensive offering yet!

Harvest and Thrive

Click here to view the full course details »

The seedlings of this idea came to me almost a year ago, and since then it’s been slowly taking shape. It’s morphed, evolved, and become what it is today in a way that has me totally dumbfounded and humbled at the wonders of the creative process. I was actually feeling pretty stuck with it at one point. Not even totally realizing I was stuck, because I was so busy running my other ecourses, putting on YxYY, traveling, and feeling *completely over the moon* in my growing coaching business.

But this one kept knocking at my door.

I’d have new ideas for it all the time. I’d write them down, share them with friends, and get super excited. I’d make some progress here and there. I’d record a video, write some emails, schedule some plans… but somehow it just wasn’t coming together. Then recently – actually just a short 30 days ago! – it all came to me like a lightning bolt. WOW is that a cool feeling.

Couldn’t be more fitting really, because it literally felt like the door blew open, and the crisp fall air brought in leaves of clarity and guidance. It was like finding the last few pieces of the puzzle, and having the whole picture finally come together. Huzzah!


What a gift…  This year I’ve taken to calling myself a Doula for Hatching Big Ideas. Not only is it more interesting than saying I’m a Coach & Creative Business Consultant, but it really holds such a deep resonance for me. I help birth beautiful ideas. Ideas that light up people’s hearts!

I love that I get to work with so many brilliant souls, coaching them through untangling their fears, experiencing major shifts, and supporting them as they make big, bold leaps in their lives, artistic passions and careers. I also love that I get to experience this process in my own life & business, with my own creations, and that the two are so closely married.

Feel all that love and celebration? ❤
I think that’s why I’m so excited to share Harvest & Thrive with you today.
This is me taking the next step on my path. This is my calling. This incarnation has been calling me for almost a year, and I listened. I listened and let it guide me, and here we are. It’s here!!

It’s also my gift to you. My way of serving the world. My way of sharing and giving all that I have learned in coaching others, and coaching myself through my own creative process. It feels like a gift to me to be able to share it with you! I think that’s what they call a win-win, which is pretty much my favorite way of doing business. ;)

I would love to have you join me for this experience. If not the entire course, then whichever one of the modules feels right for you (yes, they’re available individually)! It’s a grand experiment, and it’s going to be really fun to see what comes of it.

Thank you for reading my shmoopy post. I wish this feeling for everyone! :)

Big love & hugs,


Mentoring at Women 2.0 Conference in Vegas, baby!

I’m thrilled to have the opportunity to mentor at yet another amazing conference full of entrepreneurs, innovators and forward-thinking creatives!

women 2 logo

2020 Vision: Designing Work, Life & Play
November 14-15, 2013. Bellagio Ballroom, Las Vegas.
A must-attend conference for investors, entrepreneurs, engineers, and designer



I’m a huge fan of Women 2.0, and have had the pleasure of participating in many of their events over the last few years. I mentored at their SF Pitch Conference earlier this year, and helped out as a volunteer at their Pitch conference on Valentine’s Day last year (see photo on the right). In fact, that was an exciting day, as that evening Brandon drove over the paperwork to me to sign for Stitch’s seed round!

I also co-hosted (spoke at) one of their Founder Friday events last year while I was serving as Co-Founder at Stitch, and it’s thanks to their awesome Women 2.0 Co-working event in 2009 that I met some of my dearest friends!

Designing Work, Life & Play

I love the title of this upcoming Women 2.0 conference, too: Designing Work, Life & Play is my specialty! As a designer who now works coaching & consulting entrepreneurs on work/life integration, I might have to start using that as a tagline! ;)

Lunch Mentorship with Seasoned Founders

Women 2.0 structures their mentorship sessions in a roundtable format during lunchtime, which I’ll be facilitating on both days at the conference. I’ll be matched up with 5-7 attendees, and we’ll all have the opportunity to ask questions, share resources and form lasting connections. It works, too, for I’m still in touch with a few of the women I met there earlier this year!

Vegas is rockin’ & rollin’ right now with the Downtown Project, and I’m excited to go back and visit all my friends there! Will you be in Vegas around this time? Let me know!

UPDATE 11/18: I’m back & it was a blast! 

I ran into several women who I had met at the last Women 2.0 I mentored at, AND a few that I’d met at SXSW V2V a few months ago. And, as per usual, I met a whole slew full of new amazing men & women who are starting companies, making huge career transitions, seeking and/or offering investment capital. So neat to see how these connections create a ripple effect propelling ideas forward and bringing people together!

Willo O'Brien mentoring at Women 2.0
Action shot from Thursday’s Lunch mentoring session – great group of ladies!
Photo by the talented Elvina Beck

Willo O'Brien at Women 2.0 Conference in Vegas

Thanks for another inspiring conference experience, Women 2.0!

Mentoring at SXSW V2V in Vegas, baby!

I’m excited that I get to take part in two awesome, inaugural conferences happening in the burgeoning startup scene in Las Vegas!

v2v_logoFirst up is the first ever South by Southwest in Vegas, SXSW V2V! I’m one of the experienced mentors that attendees will have access to throughout the 4 jam-packed days. Sessions are available with me on Monday morning, starting at 10am. So curious to see how this goes!

If you’ll be there, book your session online now & let’s rap about creativity, self-care, culture and community, marketing, launching, iterating, kicking ass… life! I’m all about it.

I’ve only taken a peek at the schedule, but I’m super excited to see Scott Belsky of Behance/99U speak on Monday afternoon. Additionally, I have a number of other friends who have either moved there, work there part time and/or will also be speaking/mentoring at the conference… so this should be fun!

Come November, I’ll be flying back to Vegas to once again be a mentor at the awesome Women 2.0 Conference… this time it’s the Las Vegas Edition! I’ll do another post about that soon, but suffice to say I’m honored to lend my time to these awesome communities.