This article is part of our Transformations series, a series of in-depth articles detailing the stories behind high achieving young authors & entrepreneurs.
Startup vs dream job? Why I chose dream job.
Jaclyn DiGregorio Focused on Her Purpose and Found Out She Could Create a Dream Job Herself.
What happens when you find out the ‘dream job’ you’ve been working for all your life doesn’t really believe in you? Maybe you sulk at the unfairness of life, or instead you kick that to the curb and do your own thing to prove them all wrong. The CUSP Method offers entrepreneur Jaclyn DiGregorio the chance to share these lessons with others and open up about her struggles with weight and depression. Sometimes that’s all the motivation we need to create our own dream job.
One of my favorite movies is Election, the 1999 black comedy by Alexander Payne detailing the complex story of a high school election for student council president. I love the film for two big reason: 1) Payne is an alum of my high school and he sets the movie in our shared hometown of Omaha, Nebraska; and 2) Tracy Flick. If you haven’t seen the movie, it is quite fun in no small part due to the incredible performance by Reece Witherspoon as uber-overachiever Tracy Flick.
When Jaclyn DiGregorio introduced herself in my class, I couldn’t think of anyone other than Tracy Flick. Lest you think this is a slight on Jaclyn, it is most certainly not. Flick’s energy is infectious and she is a natural leader. But the thing about Flick you learn in the movie is that she often runs roughshod over those around her given the clarity of her own vision and awareness of her skills. It’s easy to poke fun at the character, but ask yourself the question: “If you had a student club to run and dominate a fundraiser, would you want anyone other than Tracy Flick on your team?”
However, if I were asked to select a dream entrepreneur to back with my capital, Tracy wouldn’t be it.
Sure she exhibits hustle, killer instincts, and would probably campaign harder than anyone for an opportunity to be on a team (or be the one) in charge of creating a new idea. But ultimately, someone like Tracy Flick is all bounce and no bite. Enthusiasm for a position, for creating an innovative business idea is not the same as having a specific direction for one’s efforts. Pushing for the next big thing is irrelevant when it is merely a thing, a vehicle for advancement. A bid for student body president, like a business venture is commendable, but shouldn’t that advance what that Jaclyn wants to BE, not DO?
“Jaclyn’s almost urgent presence in the first row of our classroom, her frenetic speaking style and her unbridled enthusiasm for a prior business idea (an idea that I couldn’t quite understand despite her trying to explain it to the class no less than four times that first day) made it all too easy for me to connect this very real and capable Georgetown student with Reese Witherspoon’s fictional, do-everything future Hoya.
Jaclyn was a whirlwind of effort, standing out even in a class of other talented students. Objects in motion do tend to stay in motion, but after the first few weeks of class, once I better understood her seed of a business idea, (best described as a plate with a palm tree design on it to help someone ‘smartly’ portion their meals), I was becoming more convinced Jaclyn didn’t actually believe what she was saying. I was seeing the side of Flick I didn’t want to see in Jaclyn: someone more interested in DO-ing something than BE-ing someone.
I struggled to see how Jaclyn could possibly turn her energy into a true entrepreneurial venture. I mean it was a plate —sure, a plate with a purpose — but one lacking any sort of personal depth beyond. Three weeks into class I brought in Shane Mac, Tucker Max, Jeff Reid, Dhruva Rajendra and Julie Weber to meet the students. And as I predicted, as soon as Shane asked for volunteers to give their book pitch, Jaclyn’s hand shot up, reminiscent of Flick in Election.
She marched to the front of the classroom and launched, rapid-fire, into her pitch. The coaches I’d assembled looked at one another half expecting me, or anyone, to jump in and save them from the onslaught. Finally Tucker did.
“Whoa,” exclaimed Tucker. “Whoa, whoa whoa. You’re clearly excited about this — I don’t have any idea what this is. None. But the fact that you’re excited about it is great. Now just take a deep breath and tell us your story; tell us why you want to do this. Not what ‘this’ is — but you. What’s your story?”
Dreaming big since childhood, Jaclyn saw her destiny as becoming the next great female executive in the vein of Whitman, Sandberg or Mayer. And so she was beyond thrilled to intern for “a huge company with a beautiful office building and thousands of names and faces I had never seen before. The opportunity to climb the corporate ladder. I was in the marketing department working on display and social media advertising. I learned what I needed to learn for my position and thrived at it pretty early on.”
Jaclyn being Tracy, er Jaclyn, this meant diving into “the challenges of this business”. She was going to dominate her internship. Before she started, she did her research, spoke to her friends and confirmed that the company name was too stigmatized to effectively reach millennial consumers. So she saw her opportunity to stand out as an intern who could become the ‘company voice’ for millennials.
“I knew that many of these brands in the categories of makeup and shoes, millennials were purchasing elsewhere at a higher price”, so the issue wasn’t in their products. It was in no personal relevance for an entire demographic in their existing marketing structure. From this realization Digregorio prepared a full plan — down to the projections, logos, designs and a fancy binder to hold it all — for a personalized digital platform to win back millennial consumers. She had done everything anyone could ask for and backed it up with data, research and feedback from potential customers. Never one to shy away from a challenge, she even proposed herself to lead the project after she graduated, working remotely during her senior year and relying fully on the company’s existing internal resources so the costs to implement would be low.
Yes, she dominated.
But I can imagine the patronizing look that probably came after her presentation as her boss — a Vice President reporting up to the CEO — politely took her materials (laminated binder and all), smiled and patted her on the head with a ‘that’s so cute’ smirk.
“Listen, Jaclyn,” he replied. “This is great work — really truly great — but we’re not set up to move at that speed. You’ll learn with experience that big corporations are these slow moving ships and it will take a couple years to get that setup — even if we got it approved.”
But big thanks for the cupcake, Tracy, it was delicious.
Undeterred by the prospect of now going into her senior year without a job, she told her boss and the company she’d thought could be her career launching pad ever since she’d accepted the internship:
‘Thanks but no thanks.’
“I am young and full of ideas and drive. I still think my idea for the corporation was genius, and I realized that if I can come up with ideas like that, why would I give them to someone else so they can pay me an entry level salary. I knew at this point, I was going to be an entrepreneur upon graduation. Even if I only was successful enough to pay myself an entry level salary, I would much rather be working for myself and putting my ideas into action, then working for someone else and letting them slip through the cracks.”
Okay, new challenge: figure out a new life goal.
‘If they don’t believe in me, then I’ll believe in me,’ she thought.
And that’s where I’d misread Jaclyn as Tracy Flick. Jaclyn’s enthusiasm was masking something deeper — part of it was this rejection of her life plan by a boss who miscast her as an inexperienced entry-level cog (perhaps as I did, someone in the vein of Tracy Flick).
She had written a nearly 200-page book about this particular business idea after all. But why the plate? Why a portion control business? Jaclyn was fit and energetic, so it struck me as odd that she insisted on a kitchy product offering portion-control instructions to help manage weight. She was clearly excited about the idea, but I couldn’t quite figure out why even as we neared the halfway point of class. As someone who has seen thousands of “ideas pitched” over the years, unless there is a deep personal connection to the problem, it is unlikely the entrepreneur will stick with it.
Jaclyn hadn’t slowed down in her quest enough to share what ‘it’ was. Week after week, she continued to write more about her product with nary a word about why she cared about the plate and nutrition in the first place.
“I don’t know why anyone will care about this,” I bluntly shared with her when she asked for feedback on her book’s introduction. “Why should anyone trust you to lecture them on how to lose weight from a plate with a pineapple on it?”
Never one to back down, she smiled and said she’d revise the introduction again. I shrugged, thinking that meant more work for her without much progress towards what I was really asking.
But that was where I was wrong.
“That’s when I finally started writing about my story and the times I really struggled due to being overweight, 30 lbs overweight. It caused me to really lack confidence and it impacted all areas of my life. I was also concerned that my GPA had dropped because as a Georgetown student, I want everyone to think that I’m very intelligent. And as someone running a business, that people are purchasing products from, “Oh no she had low GPA at one semester.” I didn’t want anyone to think that about me. I remember asking, “Should I say that? What should I say about this?” And then I realized that people can relate to real people. I’m not some fake person who’s hired to act but it’s my real story. Nobody is perfect and everyone goes through bad times and good times.”
She’d been hesitant to share something so personal that offered a blemish on the near-perfect exterior she presented. She was a fixer and she’d fixed the problem. Done. She didn’t stop to think more about the challenge she’d overcome because it was a momentary blip of weakness. No one needed to know.
But now she’d been asked to tell her why — why she was authentic, real and relatable. Why she wasn’t Tracy Flick.
That was the very moment she became an entrepreneur, an unstoppable force who knew who she wanted to BE. And what she was going to do to truly BE that person. Her book went from a pitch for an idea to her story with her struggles; a commitment to her reader to join them on their own journey.
A life calling. Her purpose.
Her life’s calling wasn’t plates — but health, hers and others’ — that’s when I knew my job was to push her to focus on achieving that mission. Which was why I mentioned she should consider combining her book and plate concept into a real business launch through a Kickstarter.
Honestly, I throw out ideas to ‘wantrapreneurs’ a lot, but once I knew that Jaclyn was committed to do whatever necessary to launch her career as an entrepreneur, I was pretty sure she’d give the launch idea serious consideration.
I’d really been thinking Jaclyn would do a $5,000 — maybe a $7,500 — launch that would be easy to hit with a few targeted emails and a push among her family and friends. A way to get started with her business, show off her commitment and build momentum.
But get to $20,000 in under a month?
Whew… that’s a really big lift for a concept without a super cool tech idea or something that really captures the novelty, early adopter crowd. Definitely not a layup… more like a half court heave, if you asked me honestly.
And yet as the person who ‘kickstarted’ her to consider doing this, I owed it to her to show my support. So I pledged a couple hundred bucks and thought, “I wonder if she gets to keep the money pledged if she doesn’t hit the $20,000 goal?”
(The answer, I’d later find out was: Definitely not. Double damn.)
So I was getting a little concerned for her when she started stalling.
“I’ve read all the blogs and stories about Kickstarters,” Jaclyn insisted. “So I know stalling is normal in your Kickstarter, like it happens to pretty much everyone. I just didn’t quite expect it so early. I’m only like a third of the way there.”
I’d received a message that — when read with a bit of skepticism — was clearly expressing some real doubts about her ability to hit $20,000. She’d proposed a “Hail Mary” idea, one I was doubtful could work even with the benefit of unlimited time (which she didn’t have). And yet here’s the thing about Jaclyn: she’ll never be outworked, but she could be out-strategized. And we needed to come up with another strategy because what she was doing wasn’t working.
“What happens if you stop trying to get $5 sales and instead focus on getting $1,000 sales?” I asked.
This idea wasn’t something she’d considered. She was prepared to go door to door and sell 4,000 five-dollar cupcakes if she had to. I’d just offered her another way to get there. And she was processing this new paradigm.
“I mean yeah,” she said. “I sell 15 like that and then I’m there, huh? Why didn’t I think of that?”
I smiled. Objects in motion…
The effort put into, and growth resulting from her bookmaking process was coupled with Digregorio’s realization that vulnerability is strength.
Motivation + Authenticity = CUSP.
Concentrate Understand Supplement Portion.
Well-portioned, meaningful motivation, just like a meal, is much healthier than an endless buffet of energy. Using a book to present Jaclyn’s own self, priorities and pains was so much more compelling and necessary than having her try to launch a business while presenting a pristine facade à la Tracy Flick.
“When I discovered CUSP, I found that point that I believe most people search their whole lives for. It is the intersection of happiness and health and it’s the peak point on a graph. It’s the maximum happiness you can have while achieving maximum health. And I want to help other people find that point in their lives, because I know from my interviews that hundreds of people (I would argue millions but it would have been impossible for me to interview a million people) struggle with the same issues I did.”
As the days ticked down towards the end of her Kickstarter goal, her focus intensified and suddenly she was less than $300 away from the $20,000 goal with 12 hours to go. She’d nearly done what I thought was impossible.
“I’ll fund whatever is left to get you over the top,” I offered as we chatted with the realization it was only a matter of time before Jaclyn reached her goal — a goal that still felt like a reach when I’d chatted about it only days before with Shane Mac.
An hour later, unable to resist giving her the satisfaction of reaching her Kickstarter, I upped my pledge to tip her over. She’d done it.
Jaclyn shares “although I’ve always worked hard on school, I think that as hard as I worked on the book taught me, launching your own company is not the same. It’s not constant thinking waking up in the middle of the night with an idea and writing it on a note on your phone.” Even with her passion more focused on CUSP, Jaclyn juggled the Kickstarter effort, “realistically a 60-hour-a-week job on top of school, waitressing at The Tombs, and trying to see and spend time with my friends, boyfriend and family”.
What made that overwhelming season worth it for Jaclyn? Connecting how difficulties turned her into an expert on an experience that was not an isolated one, and how her energy could be used to help others.
“It’s not about money (although being more well off than I was growing up and spoiling my parents for the many things they have given me would be nice). It’s about changing people’s lives. When I was in that sophomore slump, I was 30 pounds overweight and had an incredibly unhealthy relationship with food. I used to write about it in my journal. About how all I wanted was to be skinnier and I wanted to be able to go to a restaurant with my friends and not feel guilty that I was about to overeat. I wanted to feel healthy and not fear food and being overweight. I wanted to love my body and love myself. But I didn’t know how.
The work and dedication Jaclyn Digregorio has put into her book, and now her business, has become compulsory in the best sense of the word.
“I think that just talking to people and teaching people about what I’ve learned and seeing how excited they are in trying to implement it in their lives, and how they tell me they can’t wait to read the book. That’s something that really makes me believe that the thing that I’m passionate about has a lot of validity and there are people out there who could really use what I have to teach.”
Brands and businesses do not succeed, cannot even be built, on ambition alone. Jaclyn has discovered that deeply personal value is the driving force behind as much as it shapes the true need for her ideas.
“I identified a need that my products solved and I tried to articulate the need and other ways to solve it. The book doesn’t really talk about the product at all but just the need and ways to solve it. I did that by interviewing people and trying to see if they identify the same needs. When I found some really great stories of people that had similar issues to me, that are in similar things the product really aims to solve, that’s what I ran with. After my first draft, I realized that everything I talked about had a theme but I needed to put them all together. That’s when I came up with CUSP. I really identified everything as in one of the four steps and really brought everything together.”
An entrepreneur is a person who organizes and manages an enterprise or business with considerable initiative and risk. But just as much, an entrepreneur is a person who manages themselves differently than their peers in order to acheive what is perceived as impossible or unknowable. In entrepreneurship, the risk is not only financial. There is no product, no book, no business without risking who that entrepreneur really is.
Jaclyn’s work speaks to this. With all she wants to give back to her parents, she shared, “they are the most supportive parents in the world. I’m sure a lot of kids say that, but I’m also sure that a lot of those kids didn’t say “mom and dad I’ve decided not to take one of the prestigious jobs I could land out of Georgetown and instead start my own company.”
Jaclyn’s journey is a reminder that for all the hustle, her innate hustle, conceptualizing and then fundraising for a business requires, entrepreneurship is successful when it is reflective and personal.
“So many people out there can relate to my experiences whether or not it’s a small way like, ‘I’ve had some issues with my weight at some point in my life or a larger way like I had an eating disorder’ and people come out with personal stories to me which is really meaningful and really impactful and inspires me further.”
It’s funny that unlike many people I advise, coach or teach, I didn’t need to push or motivate her — I only needed to focus her. This presented a new challenge because I didn’t need to inspire her to do work. Jaclyn owns this, “I think that I am an extreme risk taker and I think I convinced myself that I can do anything that I put my mind into and that as long as I work extremely hard I can defy the norms and the standard.”
Ultimately I was serving as a funnel, narrowing the tidal wave of her enthusiasm into a channel fueling what she most wanted to do. Her goal was not really starting a business, but helping others. And Jaclyn did this by sharing the tools she used to transform her life.
She set her mind to this and now graduates with the seeds of a career as an entrepreneur. She missed the final class of the semester with the excuse, “A gym hired me to be their on-staff nutritionist for the month, so I hope it’s okay if I skip the class.”
Yeah, pretty sure it’s okay.
Into this summer and fall, Jaclyn will be marketing her book, portion plates, wellness workshops, health coaching and most incredibly developing an app to help people follow The CUSP Method in everyday life. Once she graduates, she will really be able to focus on it “full-time”. She’s had to message me cancelling calls or meetings because she was “out with clients” or “working from the gym” already.
CUSP is her platform, an extension of her personality and life. So important she’s made time to get her nutrition certificate, and the connections Jaclyn continues to develop through workshops and with her new clients speaks to her credibility. Jaclyn is still as much of a tornado of effort and drive as I perceived at the beginning of the semester.
Let’s be real, Digregorio has become even more lethal. A perfect storm of focused, vulnerable and engaging success that is still gathering strength.
She was always someone on the CUSP of greatness; she just needed to slow down to recognize it.
To connect with Jaclyn for consulting, speeches, presentations, interviews or consulting work, visit https://www.cuspthreesixfive.com/. Purchase The CUSP Method on Amazon. Watch her interview on Youtube at Signal Class.