I'm Michelle and this is my Fuck Up Story


Before we get started on this blog, here’s a little context…

Last night, I was a speaker at an event called “FuckUp Nights” cohosted by Eve Encinitas and Co-mmunity La Jolla.

Sooo… What is Fuckup Nights exactly?

Here’s a little bit more about the event: “Fuckup Nights is a global movement and event series that shares stories of professional failure. Each month, in events across the globe, we get three to four people to get up in front of a room full of strangers to share their own professional fuckup. The stories of the business that crashes and burns, the partnership deal that goes sour, the product that has to be recalled, we tell them all.” https://fuckupnights.com/


My Presentation

Here are my slides and my speech (pretty much verbatim, since I practiced from this script 4x in the car yesterday before going in) alllll about my personal/professional Fuck Up. Enjoy!

FUN_Michelle Wintersteen.jpg

Why I’m Here:

My name is Michelle and this is my fuck up story. (but you already knew this because you are here reading it).

I grew up in San Diego and went to college at the University of San Diego (you can read my alumni spotlight here) where I double majored in Fine Arts and Art History.

I was a member of a sorority (go Gamma Phi) but also am part of a sorority at home, as I am the oldest of 5 sisters.

I also come from a long line of female entrepreneurs, my great grandmother, grandmother, aunt, mom and sister are all business owners, so it’s no surprise I would be one too.

FUN_Michelle Wintersteen 1.jpg

My Work:

I started my business, MKW Graphics, between my junior and senior year of college. Within the art department, I always felt like I created better work when I was presented with a ‘creative challenge’ as I felt that I rarely fit the stereotype of the ‘tortured artist’ squirreled away in the studio. I was way too much of a people person for that. After graduation, I took my business full time and started working for creative entrepreneurs who wanted to make their brand visions…visual.

After taking just about every graphic design job under the sun in order to make connections, get experience, and grow my portfolio, I started to find is that what I was offering went far beyond graphic design. My ‘foot in the door’ was helping my clients with their logo designs. But as most of us know, just a logo doesn’t quite cut it.

My passion for small businesses helped me take the logos and create brands to support them. (Want more here? Read: The Difference between a Logo and a Brand Explained in Cake) Designing just logos turned into designing fully functional brands -- with vibrant websites, print collateral, digital collateral, social media, content marketing etc.

FUN_Michelle Wintersteen 2.jpg

Favorite Clients:

Two of my favorite clients are these two people.

Lauren Allen (middle) is a corporate dropout who drove circles in the parking lot of her office building desperately wanting to start her own thing. Lauren took a leap of faith moving out to California to start her business coaching practice.  We connected through the networking group Boss Babes Brunch Club and created her brand, Right Hand Business Coach together.

Braden is a small business lawyer who took a risk in his own way (no surprise there), by hiring me to design his brand for his legal practice (Braden Drake Law) before even getting his bar results back.

The three of us were in a bi-monthly networking group together and really enjoyed supporting each other’s businesses, passing referrals, collaborating and co-working regularly.  Back in spring 2017, Braden pitched Lauren and I on an idea that also happened to be a risk.

FUN_Michelle Wintersteen 3.jpg

Taking a Leap of Faith:

I am not the kind of person to be intimidated by taking risks or ‘leaps of faith.’

  • Entrepreneurship is a leap of faith.

  • Moving out of an apartment to go travel the world is a leap of faith.

  • Jumping off the 11th largest bungee in the world in the middle of Africa is for sure a leap of faith.

Which is exactly what I did. (Read More: Real Life: Feeling OK about not Having a Plan)

In 2016, I packed up my apartment in Solana Beach and set out for a year and a half of adventures with a digital nomad travel group called WiFi Tribe, working remotely from countries like Costa Rica, South Africa, and Croatia.

All I need to do my job is my laptop and a solid wifi connection, so I took an opportunity to travel the world, working remotely, meeting amazing people and having incredible experiences. (I you’re interested in more digital nomad stuff, Read: Mobile Office Life: Working Remotely in 2017)

let’s write an ebook!

Braden approached Lauren and I about co-authoring a guide for small business entrepreneurs, aka mine, Lauren’s and Braden’s ideal clients.

When someone starts a small business, they are most likely passionate about their small biz idea, but don’t know what’s involved in taking that dream to all the way to being a legit small business.

We spent 8 months writing, editing and revising our respective chapters, and then I spent 100+ hours designing (because if my name was going to be on it, the design was going to have to be on fleek), the Small Biz Start Up Guide.

The Small Biz Start Up Guide is a 100+ page, no-fuss, e(work)book that walks new entrepreneurs through the small biz planning, legal and branding process.

SBSUG (for short) would not only be an ebook, but would also be an entrepreneurship BRAND, supporting small biz owners, hosting events, writing blogs, etc. to better serve the audience we knew so well… so we thought.

FUN_Michelle Wintersteen 5.jpg

Beware of Kool-aid

We live in the era of the digital product.

Thanks to the advancements of social media and the online marketing space, it seems as if everyone’s brother’s friend’s mom’s dog has a podcast, a course, a challenge, a product or a ‘passive income’ revenue opportunity.

And to be honest, I was drinking that kool-aid, too!

I read Tim Ferris “4 Hour Work Week” and saw the appeal of ‘making money in your sleep’ like a bright shiny object. In fact, I was halfway there already! I was traveling, sipping coconuts, visiting exotic places, and curating my instagram feed to look as if I DIDN’T work that much…(lies, I was working all the time, if not more than when I was in the states).

Safe to say, the Start Up Guide FELT LIKE this kind of opportunity.

We set for a mid July 2018 launch date, curated our social media hype, built out an email list, and waited for the orders to come through…

FUN_Michelle Wintersteen 6.jpg

Ready. Set. Launch.

That July, we sold two.

Two copies. Two is better than nothing though! People just had to hear about us! I was convinced of it! We had our website up and running. We were on Pinterest. And Facebook. We were on instagram SLOWLY growing our following. I was telling everyone I knew about start up guide, but alas… minimal sales.

Then the nerves crept in, doubt crept in, and the feeling of “I just spent SO much time on this freaking project and it was all for not” overruled.

FUN_Michelle Wintersteen 11.jpg

Time to Pivot?

I panicked and I got frustrated. (Here’s me frustrated)

Lauren and Braden and I went back to the drawing board. How were we going to let people know about start up guide. We thought maybe events? We had connections at the co-working spaces and hosted 3 events related to our chapters. Total flops. Minimal attendance, and pretty much a world wide waste of time.

I felt like I didn’t want my name on something that flopped, LET ALONE something that I had such a big role in.

This was a side hustle. This was a personal project, this was something that I wanted to see be successful.

I put Start Up Guide on a back burner, and took on more client projects, filled my calendar, and did the bare minimum for SBSUG marketing.

Sales to Date:

It’s October. We launched in July. And we have sold 7 guides. What I do know about Small Biz Start Start Up Guide is that the content is good. Not only is the content good, but it’s helpful…But my FUCK UP is in the branding and marketing and that’s what I do for a living.

This is a big chip on my shoulder that I have carried around for a while and I think, to do it all again…

Here’s what I would have done differently:

FUN_Michelle Wintersteen 8.jpg
  1. We had no (well, very little) audience/community before we launched: I think that this is our biggest fuck up. No one likes being pitched on something used-car-salesman style if they have no idea what it is. Braden, Lauren and I all had our own audiences, but Small Biz Start Up Guide as a brand might as well have been an alien. We did NOT groom our audience through a ‘know-like-trust’ strategy.

  2. We failed to justify the price value, and in doing so, didn’t position ourselves competitively within our market: The SBSUG is $127. This is much more expensive than your standard ‘Small Biz for Dummies’ book you can find on amazon. We didn’t spend ENOUGH time explaining WHY we priced the book at that level and how what we offered was DIFFERENT that what you could find elsewhere.

  3. We weren’t where our audience was. We hosted events at co-working spaces. If someone is already working in a co-working space, not only do they most likely already have a business, but their business is successful enough to PAY for an office space. And although I still believe they would find what we had to say to be helpful, pitching them on a $127 guide on how to start a biz was a fuck up.

FUN_Michelle Wintersteen 9.jpg

What I learned:

I give a big ol’ middle finger to Start Up guide, but with a smile on my face. I’m not one for quotes, but there’s one that my mom told me when I was younger that has always stuck:

“Everyone you meet in life is a blessing or a lesson.” Which I want to apply now to “Everything we do in life is a blessing or a lesson.”

Start Up Guide for me is both a blessing AND a lesson.

It’s a BLESSING in that I am lucky enough to be able to work for myself, travel the world, do what I love and STILL be able to take on personal projects that push me mentally and creatively. Start Up Guide is a LESSON in that not everything has to be successful. Not everything has to go flawlessly, and that not every endeavor is going to be a home run. It’s also a lesson on not getting caught up in the trends, the fads, or the fallacies that we can all just ‘make money in our sleep’ as the passive income gurus love to brag. (PSSSTTT… it’s kind of marketing bullshit). It’s a lesson on collaboration, hard work, and pushing oneself to do something you’re proud to put your name on. As much as I see SBSUG as a flop, I am still glad to have my name on the cover and my face alongside my colleagues. Even if no one buys the damn thing.



In all, I found that sharing my FuckUp story out loud in front of a group of strangers to be extremely cathartic. I think that when we share our failures, it helps us celebrate our successes. I think that the more we can all be open about how we grow, what sucks, what works, the more we can support one another through all our seasons of life and business. I really truly loved this event and would LOVE to be a part of more events like this in the future.

What do you think? Leave me a comment below, or better yet, share your personal #fuckupstory!


Still scrollin’? Here are some other blogs you might like: