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January 5, 2025 13 mins
From Homeless to Millionaire The Pie Crust Cookie Story

Have you ever wondered how a single idea, born out of necessity, could spark a radical transformation and lead to unimaginable success? In “From Homeless to Millionaire: The Pie Crust Cookie Story,” we take you on an inspiring journey of resilience, innovation, and unwavering hope. .
In this riveting episode, we peel back the layers of adversity that once seemed insurmountable. Our guest recounts nights spent on cold sidewalks, periods with no stable income, and the overwhelming sense of isolation that often accompanies homelessness. Yet, amid the bleakest moments, a spark of culinary creativity emerged. With little more than a rolling pin, basic ingredients, and a heart full of grit, our featured entrepreneur crafted what would become a game-changer: the Pie Crust Cookie. This modest treat found its way into local farmers’ markets, igniting an unexpected following that paved the path for a miraculous comeback.
As the sweet scent of freshly baked dough captured hearts and taste buds, it also opened doors to partnerships, mentorships, and opportunities that once seemed out of reach. We dive into the gritty details behind every pivot—starting from an impromptu street cart to negotiating shelf space in major grocery chains. Hear the triumphant stories of forging business relationships based on sheer perseverance, and discover how staying true to a simple yet distinctive recipe catapulted our guest from an overnight wonder into a bona fide enterprise. Each step along the road was a lesson in gratitude, innovation, and fearless ambition.
Throughout the conversation, you’ll gain insights into the emotional toll of surviving on the streets and how hope can be a lifeline during life’s darkest chapters. Our guest openly shares the power of mindset, emphasizing the critical role self-belief plays when everything else falls apart. We also talk about the importance of community, from local volunteers who offer a helping hand to the compassionate strangers who become lifelong customers. In peeling back the layers of this remarkable story, you’ll see that passion, coupled with unwavering determination, can spin even the simplest idea into a recipe for monumental success.
In “From Homeless to Millionaire: The Pie Crust Cookie Story,” each tale of adversity turns into a masterclass in hustle, perseverance, and creativity. Listen in if you’re searching for more than just a feel-good narrative—this episode offers actionable tips on how to leverage limited resources, cultivate an entrepreneurial mindset, and stay committed to your vision even when the odds are stacked against you. Our guest’s climb from sleeping on park benches to generating seven-figure revenues is a testament to the human spirit’s boundless capacity for growth. Tune in to be moved, motivated, and reminded that success often starts in the most unexpected places. Don’t miss this truly inspiring episode!

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Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
Okay, So have you ever heard of those stories where
somebody takes like a hobby and it turns into a
million dollar business.

Speaker 2 (00:07):
Oh yeah, definitely seems like everyone's got a side hustle.

Speaker 1 (00:10):
These days, right, Well, that's exactly what we're diving into today.
It's this really cool story about this woman, Janie Degan.
She makes these pie crust.

Speaker 2 (00:18):
Cookies, Pipro's cookies. Okay, I'm intrigued already. What are we
talking about, like a mini pie or something.

Speaker 1 (00:23):
You'll have to wait and see. I'm not spoiling it yet,
but we found this awesome CNBC Make It video all
about her. It's fascinating how she went from like overcoming
all these personal challenges to building this whole nationwide brand.

Speaker 2 (00:37):
Yeah, the whole turning your passion into profit things. It
can be a bit oversimplified, can it. Like it's not
always a smooth ride exactly.

Speaker 1 (00:46):
And her story is like the perfect example of that. Like,
you wouldn't believe this, but she was actually superintendent before
she started selling cookies.

Speaker 2 (00:54):
Well really, it's a pretty big chot, right, And in.

Speaker 1 (00:57):
The video she talks about how, you know, she struggled
with the diction in her early twenties, and then even
after getting sober, that fear it kind of stayed with her.
She felt like stuck when she tried to go back
to work.

Speaker 2 (01:07):
Oh wow, I can see how that would be so paralyzing.

Speaker 1 (01:10):
Yeah, totally. And so baking kind of became her outlet,
like a way to kind of take control and build
something from scratch.

Speaker 2 (01:17):
I get that. It's like that feeling of accomplishment when
you create something with your own hands.

Speaker 1 (01:21):
Yeah, exactly. And get this, it all started because somebody
bought a cake from her, and like that one little
thing gave her the confidence to start thinking bigger. It's
pretty amazing how these small moments can lead to like
huge life changes. Right.

Speaker 2 (01:39):
Absolutely, It's like that saying, you know, the journey of
one thousand miles begins with a single step.

Speaker 1 (01:44):
Okay, so now that we've set the stage, let's talk
about these pie crust cookies.

Speaker 2 (01:48):
What are they? Exactly? So picture this. You've got that buttery,
flaky pie crust is the base, and then on top
of that, you've got this layer of like gooey pie filling,
you know, like your classic apple pecan chocolate, and then
to top it all off, a crumble topping.

Speaker 1 (02:07):
Okay, stop, stop, stop, I'm already drilling. But seriously, what
makes these cookies so special?

Speaker 2 (02:12):
Like?

Speaker 1 (02:12):
Why are people going crazy for them?

Speaker 2 (02:15):
I think it's, uh, it's got to be a few things.
It's the nostalgia of pie, you know, but in this
convenient cookie form, and then of course the taste, the textures,
the flavors, it's all there. Oh and actually in the video,
Jenny mentions how people kept telling her the cookies were scalable.

Speaker 1 (02:30):
Scalable. I mean, it's a cookie, right, Like how scalable
can a cookie?

Speaker 2 (02:34):
Really?

Speaker 1 (02:34):
Right?

Speaker 2 (02:34):
But that's what's so interesting about this whole thing. When
we talk about scalability, we mean like being able to
produce and sell something in large quantities without you know,
sacrificing quality or efficiency. And these pie Crust cookies seem
to have like hit the jackpot on that. They're pretty
simple to make, the ingredients are easy to get, and
they appeal to pretty each everyone plus who doesn't love
a good cookie.

Speaker 1 (02:54):
Yeah, I mean you can eat them on the go,
you can pack them in your lunch. They're definitely tapping
into that whole like I eat a treat, but I'm busy.

Speaker 2 (03:01):
Thing exactly convenience is king these days.

Speaker 1 (03:05):
Okay, so we've got a delicious, scalable product, but scaling
a business is a whole other challenge, right, Janie talks
about facing a lot of obstacles along the way.

Speaker 2 (03:14):
Oh yeah, for sure. She was very open about the
long hours, the money struggles, and then on top of that,
you know, the pandemic hit. It would have been so
easy to just throw in the towel. Yeah, But her
determination it's really inspiring.

Speaker 1 (03:28):
I mean, she was already running a successful cake business
when she started making these cookies, so she wasn't exactly
starting from scratch.

Speaker 2 (03:34):
True, but the pie Crest cookies were what really like
catapulted her to the next level. She was selling tons
of them at these street fairs and that's when she
started hearing that word scalable over and over again. But
turning a street fair hit into a national brand that's
a whole other story.

Speaker 1 (03:50):
Yeah, totally different ballgames. So how did she make that leap?

Speaker 2 (03:53):
Well, the pandemic actually forced her hand in a way.
She had to pivot to e commerce to stay afloat.
It was a risk move, especially with everything going on,
but it turned out to be brilliant.

Speaker 1 (04:04):
So instead of just selling locally, she was suddenly able
to reach customers all over the country exactly.

Speaker 2 (04:09):
And the numbers are crazy. She's selling something like thirty
thousand to seventy thousand cookies every single month. That's a
serious operation. You've got to think about buying ingredients in bulk,
managing production, shipping, fulfilling orders. It's a whole logistical dance.

Speaker 1 (04:24):
It's not just baking anymore. It's like systems thinking exactly.

Speaker 2 (04:28):
And what's really cool is that even at this scale,
she's managed to keep that handmade quality. She's not just
pumping out cookies in a factory. She built a whole
team that's dedicated to like keeping her standards high.

Speaker 1 (04:40):
Speaking of her team, that's another fascinating part of her story, right.
Her approach to hiring is really unique.

Speaker 2 (04:45):
It is she's not just looking at resumes and experience.
What she really cares about is enthusiasm and work ethic
and she specifically talks about hiring people who've faced, you know,
challenges in their past, people who were normally incarcerated, homeless,
or in recovery.

Speaker 1 (05:02):
That's so awesome. It's like she's built a business on
second chances. Like everyone deserves a shot to contribute and succeed.

Speaker 2 (05:08):
Yeah, And what's really interesting is how that philosophy seems
to be like baked into the product itself. You can
tell there's a sense of care and attention to detail
in every single cookie.

Speaker 1 (05:19):
It makes you wonder if there's a link between employee
satisfaction and customer satisfaction, Like, if her employees feel valued
and supported, does that translate into a better product.

Speaker 2 (05:29):
That's a really good question, and you see more and
more businesses starting to realize that creating a positive work
environment it's not just about being nice. It's about building
a solid foundation for success.

Speaker 1 (05:39):
So it's not just about making toasty cookies, it's about
building a company with.

Speaker 2 (05:43):
Like heart exactly. It's a good reminder that business can
be a force for good, not just in terms of
the products we create, but also in terms of the
impact we have on the people around us.

Speaker 1 (05:53):
Now, I know Jane's got big plans for the future.
What's next for her and her pie Cress cookie empire.

Speaker 2 (05:58):
Well, she's got her site set on New York City,
expanding her retail locations there makes sense, you know, with
her starting out there and all, but she also seems
to understand that, you know, a lot of the future
is online.

Speaker 1 (06:10):
Yeah, that e commerce thing, So continuing to grow that
side of the business too seems like, I don't know,
kind of a lot to handle both of those. I mean,
like with the online and in person.

Speaker 2 (06:21):
Stores, it definitely is and that's where her you know,
that adaptability really shows. Remember like she wasn't even thinking
about shipping cookies across the country when she first started out,
but then the pandemic happened and she didn't hesitate, you know,
she just went for it.

Speaker 1 (06:36):
It's kind of wild how sometimes those things that you
don't expect they push you in a direction that ends
up being even better. It's like those wrong turns that
lead you to like, I don't know, a hidden gem
or something totally yeah.

Speaker 2 (06:49):
And it makes you think, right, like, what might have
happened if she just stuck to that one original plan.
A good reminder that sometimes you got to be flexible,
you know, open to new things, even if they weren't
what you were initially going for.

Speaker 1 (07:02):
Okay, So speaking of plans, I'm curious about, like how
she actually got the whole operation running on such a
large scale, like thirty thousand to seventy thousand cookies a month.
That's not something you can just bake in your kitchen.

Speaker 2 (07:14):
Right, Oh, absolutely not. And this is where the you know,
more technical stuff gets really interesting. The video doesn't go
into all the details, but we can make some guesses,
right based on like how these things usually work.

Speaker 1 (07:24):
Okay, Yeah, so, like what are some of the key
things that have to happen when you're trying to like
supersize a baking operation like that.

Speaker 2 (07:31):
Well, first off, ingredients, Yeah, got to get those in bulk,
so you know, Janey's probably working directly with suppliers, you know,
get the best prices on everything, flour, sugar, butter, all that.
And then equipment. You got to think industrial size mixers, ovens,
maybe even a whole separate area just for cooling and
packaging all those cookies.

Speaker 1 (07:51):
Yeah, it's like taking a regular kitchen and like multiplying
it by a thousand or something. But it's not just
the equipment, is it. You need people who can handle
that kind of volume.

Speaker 2 (07:59):
Too, exactly, So probably a team of bakers working different shifts,
you know, so the cookies are always baking, and then
more people to manage all the other stuff, like keeping
track of how many cookies there are, packing orders, shipping
them out, and dealing with customers. It's a whole like
synchronized operation.

Speaker 1 (08:17):
And I bet on top of all that, she's still
got to be thinking about new flavors, seasonal stuff, maybe
even completely new products. It's wild how she manages to
stay creative while also running this massive business.

Speaker 2 (08:30):
That's what separates the you know, the real entrepreneurs from
everyone else. I think, being able to balance that big
picture of vision with you know, the day to day stuff.
And it's clear that she really loves what she does.

Speaker 1 (08:41):
Yeah, you can totally see that in the video. She
talks about how she still gets excited about trying out
new flavors and like seeing people's reactions.

Speaker 2 (08:49):
And I think that's crucial, you know, for any kind
of success. It's that excitement, that drive to keep pushing
and trying new things even when it gets hard. That's
what keeps you going.

Speaker 1 (09:00):
What's interesting, I bet a lot of people would assume
Janie had like tons of business experience going into this.

Speaker 2 (09:05):
Right, but that's not the case at all. No fancy MBA,
no years in the food industry or anything like that.
She just learned as she went made mistakes, adapted and
figured out what worked.

Speaker 1 (09:15):
So it's not like you need some I don't know,
a big degree or tons of money to start a
successful business.

Speaker 2 (09:21):
Not necessarily.

Speaker 1 (09:22):
No.

Speaker 2 (09:23):
Jenny's story shows that it's more about like being resourceful, determined,
and willing to learn new things. She saw an opportunity,
she had a great product, and she made it happen.

Speaker 1 (09:33):
It makes you wonder, like, what other pie cress cookie
moments are out there just waiting to be discovered, right,
what other simple ideas could become something amazing, you know,
with the right mix of passion, skills and maybe a
bit of luck.

Speaker 2 (09:46):
That's the question, isn't it? And I think we should
all be asking ourselves that, like, what are we really into?
What problems are we seeing that you know, maybe we
could solve? What unique skills do we have that we
could use.

Speaker 1 (09:57):
Yeah, it's easy to get caught up in the day
to day stuff and for get to like look up
and see the bigger picture totally.

Speaker 2 (10:04):
But Jennie reminds us that sometimes those unexpected paths, those
are the ones that lead to the best places.

Speaker 1 (10:10):
There's this part in the video where she says it
feels like she's playing dress up sometimes and she hopes
she never loses that feeling. I love that it's like
the joy of making something new, that sense of wonder.

Speaker 2 (10:21):
Definitely, and it reminds us that success doesn't have to
be all serious. You know, it can be fun, it
can be playful, it can reflect who you are.

Speaker 1 (10:29):
I think there's a big lesson in there for everyone.
We hear all the time that we have to grow up,
be practical, you know, follow us that path. But Janie's
story shows us that sometimes those paths that we make ourselves,
the ones that are driven by passion and willingness to
like embrace the unknown, those are the most rewarding.

Speaker 2 (10:48):
Couldn't agree more. And I think that's a great place,
you know, to leave it for now. Jennie's story is
a great reminder that anything is possible if you're willing
to take risks, be resourceful, and you know, keep believing
in your dreams.

Speaker 1 (11:03):
So well said. Okay, all you listeners out there, what's
your pie crest cookie just waiting to be discovered? What
little steps can you take, like right now, to turn
your passions into something amazing. We'd love to hear your thoughts.
You know, there's something else about her story that really
sticks with me. It's not just about the cookies themselves, right,
it's how she runs her whole business like she's really

(11:24):
trying to do good with it.

Speaker 2 (11:25):
Yeah. Yeah, we talked about it a bit earlier, but
I think it's worth going a little deeper. Her whole
hiring philosophy. It's a great example it.

Speaker 1 (11:33):
Is, I mean, putting enthusiasm and work ethic above someone's past.
That's already pretty cool, but then actually looking for people
who might have trouble finding jobs otherwise that shows real
commitment totally.

Speaker 2 (11:45):
It makes you think about the impact that business can have.
You know, it's not just about what you sell, It's
about the opportunities you create for people.

Speaker 1 (11:52):
Right, It's like those ripple effects exactly.

Speaker 2 (11:55):
And with Jane you can tell that, like her dedication
to her team, it shows up in the product. Remember
how you were saying you can almost taste the care
and attention in those cookies.

Speaker 1 (12:04):
I do. Do you think that's really connected? Like when
people feel good about their work, maybe they just put
more into it and then as a customer you can
actually feel that.

Speaker 2 (12:12):
I think. So it's about creating a workplace where people
feel like they're part of something bigger, Like they're not
just there for the paycheck, They're part of the mission.

Speaker 1 (12:19):
It's kind of like that, do what you love and
the money will follow thing, right.

Speaker 2 (12:22):
Maybe, But I think it's more than that. It's about
finding that balance between what you're passionate about, what's meaningful,
and you know, actually making a living.

Speaker 1 (12:32):
Yeah, that's a good way to put it, And that's
why Jane's story is so inspiring. She's not just making money,
she's building something with like real soul.

Speaker 2 (12:40):
I totally agree. It reminds you that you don't have
to pick between doing good and being successful. You can
do both, and honestly, when you do both, that's usually
when the really great stuff happens.

Speaker 1 (12:51):
Okay, So, as we wrap up our deep dive into
Janie Degan and her pie Cress Cookies, what was the
biggest takeaway for you? What really stuck with you from her?

Speaker 2 (13:01):
I think for me it's that reminder that success isn't
always a straight line. It's okay to take detours, Yeah,
to try things out, even if they don't work out.
Sometimes those messy moments are where we figure out what
we're really good at.

Speaker 1 (13:14):
That's a great point. Okay, so for everyone listening, if
you're feeling inspired, let us know what you're thinking. What
are your dreams? What can you start doing today, even
just a little thing to make those dreams happen? Remember
like that saying it all starts with one step, just
like that first pie cress cookie.

Speaker 2 (13:30):
And who knows, maybe someday we'll be doing a deep
dive into your success story. Until then, keep exploring, keep creating,
and keep diving deep
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