Ginny Jacobs of Surprisingly Baked: “A goal or purpose”

A goal or purpose — You must have something you are working towards which is clear in order to ride these highs and lows. Simon Sinek talks about finding your “why,” and I have tried to remind myself of this in every instance of stress or difficulty. If you lose sight of the end goal, every hiccup […]

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A goal or purpose — You must have something you are working towards which is clear in order to ride these highs and lows. Simon Sinek talks about finding your “why,” and I have tried to remind myself of this in every instance of stress or difficulty. If you lose sight of the end goal, every hiccup along the way will feel like the tsunami that will ultimately crush you and your business. By focusing on the end result or your ultimate goal or purpose, every frustrating or trying moment feels small in comparison.

Being a founder, entrepreneur, or business owner can have many exciting and thrilling moments. But it is also punctuated with periods of doubt, slump, and anxiety. So how does one successfully and healthily ride the highs and lows of Entrepreneurship? In this series, called “How To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur” we are talking to successful entrepreneurs who can share stories from their experience. I had the pleasure of interviewing Ginny Jacobs.

In late 2019, Ginny Jacobs finally nabbed her dream job in the hospitality business and moved to the D.C. area. A few months later, the pandemic struck — and Surprisingly Baked was born. Like many other Americans, Ginny started baking during the quarantine as a way to curb stress. She and her fiancé, Guy Cook, tested and tasted brownies, cookies, and other treats. She began experimenting with cookies and brownies baked with surprises inside, including Oreos, Nutella, caramel, frosting, and more. When Ginny’s corporate job finally shifted from “working at home” to “furloughed” to “laid off,” she decided to go all in. In just a few short months, demand for Surprisingly Baked’s tasty treats has grown, as has the brand.

Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

I moved to the D.C. area at the end of 2019 for a job in the hospitality industry. That was my dream job at the time! However, a few months later, the COVID-19 pandemic hit, and I found myself unemployed. That’s when Surprisingly Baked was born!

What was the “Aha Moment” that led to the idea for your current company? Can you share that story with us?

I had this idea for a long time. Years ago, I baked an Oreo-stuffed chocolate chip cookie recipe with a girlfriend, and thought, “wouldn’t an entire bakery dedicated to stuffed baked goods be so fun?” Each goodie would contain a “surprise” inside, like a box of chocolates! I thought this element created a fun experience — not only do you get a delicious cookie, you have the added element of surprise!

The bakery idea was mostly a pipe dream — something I might do after retirement, I thought. When COVID-19 hit, and we were stuck in quarantine, the idea came back to me. I knew this was my chance.

In your opinion, were you a natural born entrepreneur or did you develop that aptitude later on? Can you explain what you mean?

I’ve been a doer, creator, and entrepreneur for as long as I can remember! By age 10, I was already organizing the little girls in the neighborhood to put on shows, created a summer day camp, a spa, a restaurant, and a rock concert — you name it, I attempted it! Once, we even pulled off a full-length performance of The Nutcracker ballet in my school auditorium — choreographed and directed by me — and 50 people turned up. I think it was not a matter of “if” I would ever start my own business, but rather “when.”

Was there somebody in your life who inspired or helped you to start your journey with your business? Can you share a story with us?

There are so many!

First and foremost, I couldn’t have started the business without my fiancé, Guy. He was my emotional support system and our sole source of income until the cookie business got up to scale. Entrepreneurship gets incredibly hard at times, and he has been my rock. He has provided stability, and always has a positive attitude.

What do you think makes your company stand out? Can you share a story?

Our branding and authenticity. We don’t take ourselves too seriously (with the exception of making seriously delicious cookies). All of our products and content are relatable to our customers and target market. I think there is also some aspect of connection that our brand evokes — whether it’s the nostalgic branding of our products or the open dialogue and honesty in our sharing on social media platforms.

One of my favorite stories: meeting a new customer at our very first pop-up shop back in October, which was at a fall festival at an apartment building. We met a lot of folks that day, but there was one family that came up two more times. After tasting the cookies, they realized they needed more! They were very complimentary, which made me happy, but I never gave it much thought beyond that.

A couple of months later, after the holiday season, I was looking through customers that had the highest spend — mostly from sending our cookies as gifts to friends and family. There was a name that kept coming up; only later did I put two and two together to realize it was the family I met that day in October! That stuff is hard to track — meeting customers face-to-face and getting their continued support — but is invaluable and by far the most rewarding part of being an entrepreneur.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

  1. Tenacity. Many, many times it would have been easier to throw in the towel or call it quits. But I persevered despite the challenges that lay ahead of me. We have had companies and retail accounts request more cookies than we’ve ever produced. It was scary, but I always said “YES!” There have also been many, many late nights when I could have given in to fatigue or taken the “easy” way out, but I pushed through. As an entrepreneur or anyone taking risks in business, you have to get ready to hear “no” over and over again, and not let it get to you. There’s a common misconception that entrepreneurs are “risk-seeking” — they love the fear, the adrenaline. That’s not true for me. I am scared all the time. I am scared at least once an hour for my livelihood, my team members’ livelihoods, and for the business as a whole. Everything is terrifying. But I don’t quit — I push through that fear.
  2. Drive and desire to succeed. You could describe my desire to succeed as desperate. I want success and to be the best, so badly, and will do anything to achieve it. I remember my dad once told me, “there will always be people who are smarter, more of this or that, but you can ALWAYS be the hardest working person in the room (or class, job, etc.) because that is a choice.”
  3. Adaptability/flexibility. Spoiler alert: things will NOT go to plan while owning and running your own business. Ever. Accept and prepare for that. This past week alone I had two different team members call in sick during our biggest production week ever. And then an order for a key ingredient got canceled for no apparent reason, leaving us to scramble. Without a giant tub of maraschino cherries, we couldn’t produce a seasonal item, our “Cherry Baby” cookie, in honor of cherry blossom season in D.C. I didn’t have time to panic. We just had to be ready to pivot and make do. In this case, it meant running to the grocery store to buy some tiny, expensive jars to hold us over until the bulk ingredients arrived. You can always plan for COGS and run the numbers, but that doesn’t always take into account the hiccups, along the way, which mean higher costs. We still weren’t able to make enough products and had to shut off orders, which is never fun.

Often leaders are asked to share the best advice they received. But let’s reverse the question. Can you share a story about advice you’ve received that you now wish you never followed?

“Good things come to those who wait.”

In my corporate jobs, I had bosses or mentors that would advise me to “sit tight” or “pay my dues” before expecting to move up the ladder or before accomplishing all that I was capable of. While I’m sure they had only the best intentions, I think that’s an outdated mentality in today’s fast-paced world.

So much of Surprisingly Baked’s early success has come from my willingness to go for it, ask for what I want, and really just not wait for success to be handed to me. Good things do not come to those who wait. Good things come to those who ask and who go after it!

When I first decided to “go for it” with Surprisingly Baked last summer, there was minimal business planning, and zero time spent fiddling with Excel to run the numbers (although my fiancé, Guy, did finally convince me to calculate my cost of goods sold (COGS)). One day the company didn’t exist, and the next day I had an Instagram, a website domain reserved, and an LLC filed. I could have devoted the first few months to planning, researching and developing. Instead, I decided that the best way to learn was through action and doing.

Which tips would you recommend to your colleagues in your industry to help them create a work culture in which employees thrive and do not “burn out” or get overwhelmed?

Make time for yourself, learn to say “no”, and learn to say “yes!”! I realize this sounds contradictory, but we read so much about turning down opportunities and saying “no” to this or that when it may spread you thin. But I think, especially for women, we have to get comfortable accepting help when it’s offered.

What would you advise other business leaders to do in order to build trust, credibility, and Authority in their industry?

Be honest and transparent! Share anything and everything. Social media (Instagram in particular) is great for this.

Can you help articulate why doing that is essential today?

Connection is essential in today’s world, especially when we cannot connect in person. People love to feel “part” of something. Let them! Give them the chance to vote on your next flavor or app feature, or if you can’t do that, at least give them insight into your process.

What are the most common mistakes you have seen CEOs & founders make when they start a business? What can be done to avoid those errors?

I see many entrepreneurs spend months in a “planning” phase or “research and development.” Maybe I err on the side of being too trigger happy, but I think many founders would experience more success and higher sales if they did that planning and research through “doing.” This doesn’t mean creating 25 products, heading into big-box retail, and then seeing what works and what doesn’t (unless you have unlimited capital and time, then by all means go for it!). Instead, start with two products. Get as many sales as you can — farmer’s markets, online, pop-ups, small retail accounts — whatever works! Once you’re selling, start iterating and improving based on consumer feedback, as well as buying trends.

Ok fantastic. Thank you for those excellent insights, Let’s now shift to the main focus of our interview about How to Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur. The journey of an entrepreneur is never easy, and is filled with challenges, failures, setbacks, as well as joys, thrills and celebrations. This might be intuitive, but I think it will be very useful to specifically articulate it. Can you describe to our readers why no matter how successful you are as an entrepreneur, you will always have fairly dramatic highs and lows? Particularly, can you help explain why this is different from someone with a “regular job”?

This is so accurate, and I don’t think these feelings ever go away — whether you are just starting out or running a multi-million- or billion-dollar corporation. It is truly a roller coaster because the peaks and valleys are SO extreme and you feel them so much more deeply when you have skin in the game. When you lose a sale, as an entrepreneur, it’s not just the frustration from the feeling of losing, or a lost commission, or even just an angry boss — it’s the possibility that without that deal, your business may not live another day.

On the flip side, when you do land that deal, commissions and happy bosses are great, but what about being able to entirely change your own life and other peoples’ lives? For example, when we recently won a huge account that requires us to put out thousands of cookies each week, I had the opportunity to hire more people and create more jobs.

I think the highs and lows of entrepreneurship feel that much more extreme because every moment and every event can make or break your company. So much is riding on every decision, deal, or moment, that it’s impossible to not feel everything.

Do you feel comfortable sharing a story from your own experience about how you felt unusually high and excited as a result of your business? We would love to hear it.

All of our retail accounts have been inbound leads, for which we are so grateful. Whenever someone reaches out, the elated feeling of “we’re doing something right!” is indescribable. It’s so validating and rewarding to know that all the hard work, sweat and tears, and highs/lows are paying off and that this will in fact be a real business!

Do you feel comfortable sharing a story from your own experience about how you felt unusually low, and vulnerable as a result of your business? We would love to hear it.

I feel like it’s important to highlight or clarify that there are A LOT of moments in which I felt unusually low, vulnerable, or discouraged. Not just in the course of a year or month, but throughout each and every day.

There was one day during the busy holiday season when someone reached out on Instagram to tell me one of my cookies wasn’t filled with enough frosting. It might not sound like a huge deal, but when I read this message, I completely broke down into tears. This was coming off of nearly a week of working every waking hour to get Christmas orders out the door in time, having to let go of someone who wasn’t producing the quality we required, but was a good person, and all-around stress from every other email of “where is my order?” or “will this get here in time for Christmas, if I order today?”

The thing is, this person’s concern was perfectly valid and warranted. We had just received more orders in a day than we did in the first two months of business. We weren’t meeting our own standards for high quality. At that moment, I almost felt like I couldn’t go on.

Based on your experience can you tell us what you did to bounce back?

You have to think of the big picture and the long-term. If you get too bogged down in what’s happening that day or that minute, you’ll drown. Something that helps me too is thinking of each trying experience as a future interview answer (like now!) or a chapter in my book

Ok super. Here is the main question of our interview. What are your “Five Things You Need To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur”? Please share a story or an example for each.

  1. Support — Friends, family, community, anyone who is on your side. Being an entrepreneur is lonely, trying and just plain hard. Friends will bring you back to reality. Resources can help you problem solve and tackle big issues (more on that later). There have been countless times I’ve come home in tears from a crazy day in the kitchen and have spoken to a friend or family member and instantly felt a sense of calm and perspective. In the example I provided earlier, regarding the “minimal frosting” situation — it was my fiancé and my best friend from college (via text) that helped me work through what was really upsetting me (the lack of control over my product) and work through how to fix it moving forward (measuring specific amounts of frosting rather than eyeballing it.)
  2. Outlets/Escape — Take a walk, listen to music, something to distract yourself. Einstein talks a lot about combinatory play — the idea that doing one thing can help stimulate your brain in another area — and I couldn’t agree more. Some of my best brainstorming, ideas, or even problem-solving are done on days “off” when I’m out of the kitchen and able to take my dog for a walk in the great outdoors.
  3. Resources — Books, podcasts, Facebook groups, mentors. Perspective is one of the most helpful ways to manage the challenges of entrepreneurship. Knowing that others have gone through very similar situations and come out on top is priceless. Every day, I read and listen to audiobooks or podcasts during my drive into the kitchen. I read somewhere that you are a product of the five people you spend the most time with. Given that we’re in quarantine, and not many of my close friends are entrepreneurs, I try to surround myself with some of the greats through reading! Some of my recent favorites are Supermaker by Jaime Schmidt, Think Again by Adam Grant, and Onward by Howard Schultz. I also recently began participating in a SCORE mentorship program through the SBA and I am connected with an entrepreneur who has already successfully exited their business. You don’t have to have money or know a ton of people to tap into some of the best resources out there!
  4. Healthy Lifestyle — I am guilty of not practicing what I preach here, but I am realizing more and more the power of eating healthfully, exercising, and getting my sleep on my day-to-day energy and health. It’s so easy to let healthy eating and exercise be the first to go when you get busy, but whenever I take the time to add these back into my routine, I notice a difference in my productivity and energy. A friend of mine from college also created an awesome app that helps with healthy eating on the go called Wellory. Find these little tips, tricks, or apps that help you stay on track and prioritize them!
  5. A goal or purpose — You must have something you are working towards which is clear in order to ride these highs and lows. Simon Sinek talks about finding your “why,” and I have tried to remind myself of this in every instance of stress or difficulty. If you lose sight of the end goal, every hiccup along the way will feel like the tsunami that will ultimately crush you and your business. By focusing on the end result or your ultimate goal or purpose, every frustrating or trying moment feels small in comparison.

We are living during challenging times and resilience is critical during times like these. How would you define resilience? What do you believe are the characteristics or traits of resilient people?

Resilience, to me, means removing myself from what is happening to me. For example, losing my job due to COVID-19 pandemic didn’t happen as a result of something I did. Yes, it sucked. I felt I had finally found a job and a team I truly loved, but dwelling on it doesn’t help.

Did you have any experiences growing up that have contributed to building your resiliency? Would you mind sharing a story?

It’s going to sound silly, but I didn’t get the part of Sandy from Grease in my 8th-grade school musical and was crushed. I actually spent an entire day in a dark room crying and felt absolutely crushed. I ended up choreographing the entire production, which in the long run, turned out to be a much more valuable experience. How many 14-year-olds can say they created dances for a full-length production? And managed to get a bunch of 14-year-old boys to learn all the steps?

Flash forward to many years later, I spent the first five years of my career (right out of college) in sales. This means hearing “no” on a daily basis and learning how to build a tough shell for these instances. So, having survived “the great Sandy heartbreak” taught me to cope!

In your opinion, do you tend to keep a positive attitude during difficult situations? What helps you to do so?

I try to take everything as a learning experience. Starting this business is like earning a free MBA! I had to fire someone on the spot when they came to work high on drugs and acted in an inappropriate manner. Not only was that scary, but I had to do the entire production of 100+ cookies by myself. Rather than dwell and sob over the situation, I tried to almost look at and consider the situation from the outside in — like an anthropological study of sorts!

Another tip my fiancé always reminds me of is to think of horror stories and bad days as chapters in your future book. Or think of them as talking points when I go on the podcast “How I Built This with Guy Raz.” Envision yourself doing a dream interview, or writing a book about your success, or speaking at your college’s commencement ceremony. Your failures and setbacks will provide the best stories!

Can you help articulate why a leader’s positive attitude can have a positive impact both on their clients and their team? Please share a story or example if you can.

Your attitude is contagious — whether it’s a positive or negative one.

Ok. Super. We are nearly done. What is your favorite inspirational quote that motivates you to pursue greatness? Can you share a story about how it was relevant to you in your own life?

“If you wait for the fear to go away, the opportunity will go away too” — Leslie Blodgett

This quote prompted me to take action and start a business. I think we go through life with many “one day” ideas or thoughts, thinking that later in life we’ll have more time, or more money, or more courage, none of which I’ve experienced to be true. I think it also inspired me to realize that other entrepreneurs experience fear, too. I am realizing that there will be fear, but that it’s okay.

Another quote: “What would you do if you weren’t afraid?”

This is a common one, but an easy one to overlook, as a result. Someone recently posed this to me in a serious manner, and I found myself immediately thinking of Elon Musk — a man with seemingly little to no fear. If I wasn’t afraid, I thought, I’d have big aspirational dreams like Musk — like reinventing the automobile industry or inhabiting Mars. How many women would have the audacity to dream so big?

How can our readers further follow you online?


This was very inspiring. Thank you so much for the time you spent with this. We wish you continued success and good health!

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