A Night at The Cake Bake Shop: Work + Life Through the Eyes of Gwendolyn Rogers

a night at the cake bake shop

a night at the cake bake shop gwendolyn rogers

When you walk into The Cake Bake Shop and see all the glittery perfection laid out in front of you, it would be easy to assume that Gwendolyn Rogers has done this whole restaurateur thing a time or two. Or, at the very least, that she has a stable of enthusiastic investors and advisors to help bring her dreams to life. And you would be oh so wrong. While her cakes and goodies are served up on fine branded china, nothing along her journey of making The Cake Bake Shop into a reality was handed to her on a silver platter. Girl went out and made it happen.


After spending an evening with Gwendolyn at her shop in Broad Ripple, it became abundantly clear to me that this woman has more grit, business acumen, and determination than most other entrepreneurs I’ve met. The lessons she shared with us that night are so relevant, not only to starting and running a successful gourmet sweets shop, but also to building a career and life you love. And as she spoke, I just knew I needed to share them with you all!


So, here you have it…9 tips to following your passion and building a life you love from Gwendolyn Rogers (numbered quotes are hers; my interpretation / explanation follows).


9. “There’s always someone looking for what you have to give.”


Two of the biggest questions aspiring entrepreneurs face are, “what am I going to do?” and “how much am I going to charge?”


Gwendolyn’s advice? Follow your passions – do the thing you like, not the thing you think you’re supposed to like. Do it the way you’d want it done. Make the thing you’d want to buy. Bake the thing you’d want to eat. Paint the picture you’d want to hang. Odds are, there are other people out there who share those same tastes.


Maybe the harder part, though, is putting a monetary value on your work. Because even though you know the time, effort, and heart it took to create that work, you’re worried that people will think it’s overpriced and pass you over for another option. But here’s the thing: if you do things you like, are passionate about and are good at, people will find value in it. Don’t sell your art, your creation, your talent, or your time short…there’s always someone looking for what you have to give.


8. “Start slow, wherever you can.”


You don’t have to make a huge jump into entrepreneurship and build your dream all at once. In fact, that might not be at all financially feasible. But what you can do, at any time, is start solidifying the vision, piece by piece. Build and compile usable assets over time.


For example, the first purchase Gwendolyn made for The Cake Bake Shop was a $200 trash can that she kept in her garage for years until it was time to bring her shop to life. Second purchase? Pink Cake Bake umbrellas…and into the garage they went. Each trip to Michael’s yielded a bit more glassware or a few more silk flowers with which to create beautiful, sparkly arrangements for the eventual store.


The point is this: you don’t have to do everything at once. You don’t have to have the entire plan in place. If you know generally where you want to go, dedicate a small amount of time or money on a regular basis to lay the groundwork for what is to come. Start with the name. Get the URL. Trademark it. Build the brand. Start accumulating. And on and on until it’s time to jump in with both feet. As the old saying goes, “how do you eat an elephant? One bite at a time.”


a night at the cake bake shop

The infamous Earl’s Court Chocolate Cake


7. “Don’t be afraid to lose, because you’re going to lose a lot.”


People will tell you no. Plans will change. Ideas will fail. Unexpected expenses will pop up. Suppliers will disappear. Promises will be broken. Employees will quit, banks won’t approve you for a loan, and some customers will find any reason they can to be negative or write a bad review. That’s life, and that’s business. There’s really no other way to put it – if you’re striking out on your own, you’re going to have to grow some thick skin and get comfortable being uncomfortable. Because losing over and over and over again…well, that’s how you eventually win.


6. “Be super confident, because life is too short not to be.”


Which brings us to #6. If you need to effectively double your rate of failure in order to succeed (Thomas Watson Jr.), you need to be super confident as you plow forward. Learn how to be secure in yourself. Stand up for your ideas. Fight for your future, confident in the knowledge that the life you desire will eventually come due to dedication to your work. (And if you aren’t there yet in the confidence department, fake it!)


People sense weakness and uncertainty, and they’ll jump on it. You’ll have doubters – probably more than you would have imagined – so confidence in yourself is key when it comes to realizing your vision and building your dreams.


5. “Go after what you want.”


Story time: ever wonder how Cake Bake has so many famous fans? It’s because Gwendolyn puts herself – and her cakes – in the right place at the right time. She doesn’t ask for permission from anyone…she just goes for it. Because if Matt Damon in a Cake Bake hat or comedian TJ Miller smashing his face into the Millionaire Cake as the finale to one of his shows has any chance of benefitting her business, she finds a way to make both happen (srsly – check out the insta. There’s plenty more where those came from, including the cast of Jersey Boys and Steve Martin and Martin Short in just the past few days!).


What’s even cooler is that these aren’t just publicity stunts – many celebs have become actual fans and customers of the Shop, visiting when they’re in town for shows and ordering goodies online for special events. Now that’s good business.


But you know what? Going after what you want applies to pretty much everything in life, too. We’ve become so accustomed to sitting back and almost being observers in our own lives, rather than full-scale participants. We shrink back and say “oh, I could never!” Wrong. You can…and sometimes you really need to.


What’s that thing you’ve been chasing (or wishing for)? What’s one action step you can take THIS WEEK to make it a reality?


a night at the cake bake shop

All pictures courtesy of The Cake Bake Shop instagram (@thecakebakeshop)

4. “Inspiration can come to you anywhere as long as you’re open to it.”


Inspiration is all around us. If you’ve ever read Elizabeth Gilbert’s book Big Magic, you know what I’m talking about. Ideas want to be realized, to come to life. When you’re closed off to inspiration – because you’re too busy, because you’re not paying attention, because you ignore it when it strikes, because your ideas scare you (because you’re scared of where they might lead), because you’re not sure what to do – things feel difficult. But when you’re open – you’re curious, you brainstorm about new ideas, you allow yourself the time and freedom to think, you engage in authentic conversation with interesting people, you put down the phone for a few minutes and detach yourself from social media, you quiet your mind – ideas will find you.


Need an example? Gwendolyn and Alison (Director of Kitchen Operations at The Cake Bake Shop) once found inspiration for a new cake in a picture of a beautiful brocade blue couch. A simple text including a picture of the couch and the question, “how do we turn this into a cake?” lead down an amazing path of creativity and learning new techniques in intricate cake decoration. And if that cake never makes it to a cake stand in the shop? No worries…because the important part is that they were curious and open enough to engage with a crazy idea. The more you practice, the more inspiration will seem to strike.


What’s the idea you need to begin to engage with, or where can you carve out the time to open your mind and heart to what’s trying to make its way to you?


3. “Become an expert in everything.”


Do you want to know how The Cake Bake Shop was built, how it was decorated, and how it runs every single day? It is as amazing as it is because Gwendolyn dug in, got her hands dirty, and became an expert in every single aspect of store and business operations. You become an expert by being there for everything, every second of every day, and learning while you do it.


A short list of examples of Gwendolyn’s expertise: fixing the baking equipment, tiling the floors, updating the website, finding suppliers, creating the decorations, sourcing materials from other countries in the most cost effective way, creating a nationally-recognized brand, pricing, PR, coming up with new recipes…and the list goes on and on. Talk about jack of all trades!


Think it sounds a little intense? Think someone should learn a bit of delegation? To some extent, there should probably come a point where you can step back and watch your creation run seamlessly without you – and for Type A’s like Gwendolyn (and myself), that can be a hard place to get to.


BUT…in the early days? It’s on you. It’s your money on the line (savings, kids’ college tuition, mortgage, etc). It’s your name on the line. It is, quite literally, your future on the line. Are you going to hand it over to someone else in the essential stages of its development and hope it gets done right?


a night at the cake bake shop

Caramel popcorn cake…a personal fave!


2. “Wherever your life is taking you…go with it.”


Be willing to let go of the things you think you have planned. Life has a funny way of presenting you with challenges and opportunities that bring you to critical junctures, where you have to make a decision: do I trust where this seems to be leading? Or will I hold on to my “plan” with a death grip, even if it doesn’t seem to be where my life is taking me?


Gwendolyn’s advice: as much as possible, take it one event, one decision at a time. Embrace what’s happening, and go with it. Better yet, go FOR it.

And drumroll please, as we get to Gwendolyn’s #1 life lesson…

1. “The people you meet will change your life.”


This message really hit home with me, because in this season of my life I have come to realize just how true this is. No matter how good, smart, dedicated, or determined you are…things get done through people. Life is meant to be lived in and through relationship with others.


People are put in our lives for a reason, and every “reason” is as unique as the person we meet. Maybe it’s a soulmate – a person you instantly connect with. Sometimes it takes a while to find where people fit…like a connection that leads to a connection that leads to a connection that completely changes the trajectory of your business and brings you opportunities that you’ve never imagined. Or maybe it’s someone that just offers a piece of advice that frames something in a way you’ve never thought of before.


Bottom line: people are important. Maybe the most important part of this whole equation / journey. You must foster authentic, loving – not self-serving – relationships. As Gwendolyn says, “utilize every single contact of every person you’ve ever met,” and you just might be surprised at where life will take you.


Last Words


I wish you guys could have all been there to experience this discussion. Talking with Gwendolyn in person is an experience that can’t be truly replicated through the written word. But, I hope some of the tips and lessons written here hit home and help to clarify your path forward a bit more.


And, if you’re ever in Indy and get the chance to visit, it goes without saying that you MUST make your way to The Cake Bake Shop. People talk about these cakes for a reason! It’s so much more than that, though. The “actual” food (from French Onion Soup to Croque Monsieur to quiche to charcuterie – yes, I’ve eaten them all) is just as well prepared and swoon-worthy, the drink selection is different from what you can find in most any other place Stateside, and the environment / atmosphere is not to be missed. If you want to hear about my favorites…just ask ; )


All this, because one woman trusted in the path her life was leading, dug in, built authentic relationships, and brought a dream to life.


a night at the cake bake shop

If you go to The Cake Bake Shop and don’t instagram it, did you ever really go?

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