Securing Simma's Bakery Cheesecake on Ice

🎙️ Bob’s Food Tour — Stop #10: Simma’s Bakery

By the time the group steps into Simma’s Bakery, there’s already a rhythm to the day. The laughter is easier now. The pace has softened. People aren’t rushing from stop to stop anymore—they’re settling into the experience.

Simma’s doesn’t shout for attention. It doesn’t need to.

There’s something about a bakery that invites you to slow down. Maybe it’s the sweetness in the air, or the quiet care behind each case of desserts. You can feel it before you even take a bite—this is a place that’s been doing things well for a long time.

And then it happens—that first taste.

Not overcomplicated. Not trying too hard. Just… right.

It’s the kind of flavor that doesn’t demand a reaction but quietly earns one. Heads nod. Eyes close for a second longer. Someone says, “Oh wow,” but softly, like they don’t want to interrupt the moment.

Conversations shift here too. They become a little more personal, a little more present. Maybe it’s the sugar, or maybe it’s just what happens when people slow down enough to enjoy something simple and good.

Simma’s becomes a pause in the tour—not a stop to check off, but a moment to take in.

A reminder that not everything memorable has to be bold or loud. Sometimes it’s the quiet places—the ones that have been doing it right all along—that leave the deepest impression.

Not flashy. Not rushed.

Just timeless.

Stories from the Shop

Transcript

SPEAKER_01 0:00

So it is Friday, May 1st.

SPEAKER_00 0:02

Yes, it is.

SPEAKER_01 0:03

You and uh eleven of your closest friends from the Wisconsin Athletic Club have been rolling through the streets of Milwaukee.

SPEAKER_00 0:12

In a massive van, right?

SPEAKER_01 0:13

Oh, yeah. A 15-passenger van. And you've been at it since like 8 30 in the morning.

SPEAKER_00 0:17

Which is just a marathon.

SPEAKER_01 0:19

It really is. I mean, this is the legendary Bob's food tour. You are 12 people strong, you're navigating the city on a super strict schedule, and you have just finished an incredibly heavy, just profoundly satisfying lunch at Balastraries.

SPEAKER_00 0:35

Best way to do it.

SPEAKER_01 0:35

Right. So we're taking a stack of sources today. You know, the official food tour itinerary, historical records of Milwaukee's culinary scene, some detailed bakery menus. And the mission of this deep dive is to guide you through the very next phase of this massive undertaking.

SPEAKER_00 0:51

Aaron Powell Because stepping out of that van and into the next location, it isn't just about eating anymore.

SPEAKER_01 0:56

No, it's a full-blown logistical mission.

SPEAKER_00 0:58

Yeah, pulling up to any restaurant with a 15-passenger van full of hungry athletes, I mean, that is a massive disruption to a dining room's ecosystem.

SPEAKER_01 1:06

Oh, total chaos, usually.

SPEAKER_00 1:08

Exactly. Yeah. So a huge amount of credit for your survival so far really goes to Frank over at Balastra's.

SPEAKER_01 1:14

Shout out to Frank.

SPEAKER_00 1:14

Seriously. Based on the tour notes, Frank was basically keeping his eyes peeled for your group all morning.

SPEAKER_01 1:21

He knew you were coming.

SPEAKER_00 1:22

Right. He coordinated the timing with the Bob's food tour organizers to make sure your 12 top was handled without, you know, a a single dropped plate or delayed order.

SPEAKER_01 1:31

Which is no small feat. Handling a sudden influx of 12 people during a lunch rush. The kitchen basically has to rearrange its firing order on the fly.

SPEAKER_00 1:39

Yeah, and Frank made sure your group was taken care of so smoothly that your itinerary didn't lose a single minute.

SPEAKER_01 1:45

Not one minute.

SPEAKER_00 1:46

I mean, hospitality like that, it's the invisible engine of a marathon day.

SPEAKER_01 1:50

Frank is absolutely the unsung hero of the midday slump. So you leave Balestraries feeling victorious, right? The heavy sliding door of the band slams shut, and you're off to stop number 10.

SPEAKER_00 2:01

Stop ten, wow.

SPEAKER_01 2:02

The GPS takes you to 817 North 68th Street in Wabatosa.

SPEAKER_00 2:08

A legendary address.

SPEAKER_01 2:09

You step out and you are standing right in front of Simma's bakery. Now, the goal of this deep dive is to unpack the history of this absolute local icon. We need to strategize exactly what you should buy to eat the second you walk through the room versus you know what needs to be packed away for later.

SPEAKER_00 2:26

Because the crucial context hanging over everything we discussed today is that, well, after Simma's, you still have five more stops ahead of you.

SPEAKER_01 2:34

Right. Stop 10 out of 15, you are past the halfway point, but the finish line is still hours away.

SPEAKER_00 2:40

Long way to go. Yeah. And coming off a heavy Italian lunch at Balestrary's, the palate needs a severe pivot.

SPEAKER_01 2:46

You need sugar.

SPEAKER_00 2:47

You need sugar, you need butter, and you need a location with enough cultural gravity to justify its placement as a like a tent-pole stop on this tour.

SPEAKER_01 2:57

And Simma's fits that profile perfectly.

SPEAKER_00 3:00

Oh, 100%. The sources show this bakery actually opened its doors back in 1982.

SPEAKER_01 3:05

1982.

SPEAKER_00 3:06

Yeah, originally founded by Simma herself. And today it's Mark and Peggy Carolla who are at the helm.

SPEAKER_01 3:11

They're the ones keeping it going.

SPEAKER_00 3:12

Right. Continuing to build on a reputation that spans over three decades now.

SPEAKER_01 3:16

You know, keeping a bakery relevant and thriving since 1982, it feels almost impossible.

SPEAKER_00 3:22

It really is.

SPEAKER_01 3:23

Like thinking about your group from the Wisconsin Athletic Club, keeping a business running at an elite level for 32 years is a lot like maintaining a grueling daily workout streak.

SPEAKER_00 3:35

Oh, that's a great way to look at it.

SPEAKER_01 3:36

You don't just wake up one day and accidentally do it. It requires punishing stamina.

SPEAKER_00 3:41

Absolutely.

SPEAKER_01 3:42

And the sources highlight that in 2017, the Wisconsin Bakers Association awarded Simmons the Bakery Operation of the Year.

SPEAKER_00 3:50

Which is huge.

SPEAKER_01 3:51

Right. Winning an award for Operation of the Year sounds vastly different than just, I don't know, winning a blue ribbon at a state fair for baking a really good chocolate chip cookie.

SPEAKER_00 4:00

Yeah, totally different ballgame.

SPEAKER_01 4:02

So what does a bakery actually have to do to win a statewide award for its entire operation?

SPEAKER_00 4:07

Well, like you said, a blue ribbon for a cookie just means you nailed the ratios of butter to sugar to flour on one specific day.

SPEAKER_01 4:15

Right. Anyone can have a good Tuesday.

SPEAKER_00 4:17

Exactly. Operation of the Year evaluates the invisible machinery of the business. The judges are looking at the whole ecosystem.

SPEAKER_01 4:26

Like the logistics.

SPEAKER_00 4:27

Yeah, like how they manage their supply chain, how they handle sanitation.

SPEAKER_01 4:31

Oh, sure.

SPEAKER_00 4:31

The financial viability of their margins, and even their staff retention. Because the bakery industry is notoriously brutal.

SPEAKER_01 4:38

The margins have to be tiny.

SPEAKER_00 4:40

Razor thin. Margins on flour and sugar are basically non-existent. The hours require bakers to clock in at two or three in the morning.

SPEAKER_01 4:49

Brutal.

SPEAKER_00 4:50

And consumer tastes shift wildly from decade to decade. So surviving that requires just militant consistency.

SPEAKER_01 4:58

It's the mechanics behind the counter. It's making sure the dough is needed exactly the same way on a random Tuesday in February as it is on Christmas Eve.

SPEAKER_00 5:05

You hit the nail on the head. And honestly, the most vulnerable moment in any business's lifespan is the transition of power.

SPEAKER_01 5:11

Oh, when Simma stepped away.

SPEAKER_00 5:13

Right. When a founder like Simma, who holds the original vision, the recipes, the community goodwill, when she steps away, the business usually fractures.

SPEAKER_01 5:22

Because the new people try to change things.

SPEAKER_00 5:24

Yeah. Successors often try to cut costs, or they just lose the invisible culture that made the place special to begin with.

SPEAKER_01 5:30

But the Corollas didn't do that.

SPEAKER_00 5:32

No. The fact that Mark and Peggy Corolla took over and subsequently secured a statewide operational award tells us they managed to systemize the founder's magic.

SPEAKER_01 5:41

Wow. Systemized magic.

SPEAKER_00 5:44

Yeah, they documented the unwritten rules, maintained the culture, and modernized the business side to outcompete basically every other bakery in Wisconsin.

SPEAKER_01 5:52

Okay, so knowing that Symos runs this tight award-winning ship leads us directly to the crown jewel of their menu.

SPEAKER_00 5:59

The big one.

SPEAKER_01 6:00

The big one. This is the item they proudly, boldly advertise. They challenge visitors right on our website, asking if you are ready to taste the best cheesecake you've ever had.

SPEAKER_00 6:10

It's a bold claim.

SPEAKER_01 6:11

They formally claim the title of Milwaukee's Award-winning cheesecake.

SPEAKER_00 6:16

And you know, when a bakery with an operation of the year pedigree throws down a gauntlet like that, it is a thesis statement they are prepared to defend every single day.

SPEAKER_01 6:24

Because cheesecake is tough to get right.

SPEAKER_00 6:26

It is notoriously unforgiving. Most people don't realize it's not actually a cake.

SPEAKER_01 6:32

Wait, really?

SPEAKER_00 6:33

Structurally, it's a baked custard.

SPEAKER_01 6:35

Oh, interesting.

SPEAKER_00 6:36

Yeah, the chemistry relies entirely on the delicate coagulation of egg proteins suspended in dairy. If you bake it too fast, the eggs basically scramble.

SPEAKER_01 6:45

And nobody wants scrambled egg cake.

SPEAKER_00 6:47

Right. The texture becomes super grainy.

SPEAKER_01 6:49

Which I guess is why you see cheesecakes crack down the middle all the time.

SPEAKER_00 6:52

Exactly. The cracking happens when the edges bake faster than the center. It causes the custard to swell up and then violently contract as it cools.

SPEAKER_01 7:01

So how do they avoid that?

SPEAKER_00 7:02

To prevent that, an award-winning cheesecake requires a precise water bath or a bain marie.

SPEAKER_01 7:08

A bain marie.

SPEAKER_00 7:09

Yeah, the baker surrounds the spring-formed pan with boiling water in the oven. Because water cannot exceed 212 degrees Fahrenheit, it acts as a thermal buffer.

SPEAKER_01 7:18

Ah. So it controls the heat.

SPEAKER_00 7:20

Right. It ensures the ambient heat around the custard never gets hot enough to curl the eggs or dry at the top.

SPEAKER_01 7:25

That makes sense.

SPEAKER_00 7:26

And mastering that process on a massive commercial scale, day in and day out, that is an immense technical achievement.

SPEAKER_01 7:34

Okay, but hold on. Let's look at the reality of Friday, May 1st here.

SPEAKER_00 7:37

Okay.

SPEAKER_01 7:38

You are at stop 10. You have five stops left. You are traveling in a 15-passenger van that is going to be baking in the afternoon sun.

SPEAKER_00 7:48

It's going to get warm in there.

SPEAKER_01 7:49

Very warm. Buying a highly delicate, temperature-sensitive, dairy-heavy baked custard right now seems like a massive tactical error.

SPEAKER_00 7:58

I see where you're going with this.

SPEAKER_01 7:59

Doesn't buying a premium cheesecake in the middle of the afternoon basically guarantee it's going to spoil before you finish the tour. Shouldn't the group just wait until the very end of the day to buy perishables?

SPEAKER_00 8:09

See, waiting is the amateur instinct.

SPEAKER_01 8:11

Oh, really?

SPEAKER_00 8:12

Yeah. The veteran movie, like the true Bob's food tour level execution is deploying the equipment you brought with you.

SPEAKER_01 8:18

The coolers.

SPEAKER_00 8:19

Exactly. This is why there are coolers sitting in the back of that van. It is a high-stakes game of dairy Tetris.

SPEAKER_01 8:26

Dairy Tetris, I love that.

SPEAKER_00 8:27

You're faced with the variables of time and temperature. And instead of letting those variables dictate your schedule, you conquer them using the cooler real estate.

SPEAKER_01 8:36

Because if you wait until stop 15, you risk the bakery being completely sold out of their signature item.

SPEAKER_00 8:43

Precisely. You never leave Milwaukee's best cheesecake to chance.

SPEAKER_01 8:47

You gotta lock it down early.

SPEAKER_00 8:49

By purchasing the cheesecake now at stop 10 and packing it in the ice, your group secures the prize. You lock down the award-winning asset, entirely neutralizing the threat of spoilage for the remaining five stops.

SPEAKER_01 9:02

So it shifts your mindset from reacting to the environment to mastering the logistics of the tour.

SPEAKER_00 9:08

You become culinary tacticians.

SPEAKER_01 9:09

I love it. You acquire the target, put it on ice, and proceed to the next location with total peace of mind.

SPEAKER_00 9:14

Exactly.

SPEAKER_01 9:15

But uh that only solves the problem for later tonight.

SPEAKER_00 9:18

Right.

SPEAKER_01 9:18

We have to acknowledge human nature here. You are standing in a legendary Wahuatosa bakery. The air is thick with the smell of caramelized sugar, butter, vanilla.

SPEAKER_00 9:27

It's intoxicating.

SPEAKER_01 9:28

You are not gonna buy a box cheesecake, bury it in a cooler, and then walk back to the van empty-handed to stare at eleven hungry friends.

SPEAKER_00 9:37

No, absolutely not.

SPEAKER_01 9:38

You need something to eat right now.

SPEAKER_00 9:40

The entire sensory environment of a bakery is engineered to trigger an immediate craving. Walking out without consuming something on the spot takes a level of willpower that frankly just doesn't belong on a food tour.

SPEAKER_01 9:54

It's against the spirit of the day.

SPEAKER_00 9:55

Exactly.

SPEAKER_01 9:56

And our sources show that beyond the cheesecake, SEMAs has a massive array of specialty desserts sitting in the display cases.

SPEAKER_00 10:03

They have so much.

SPEAKER_01 10:04

They have mini pastries, cupcakes, cookies, intricate dessert bars, and various morning goodies. Yeah. But they also dedicate a huge portion of their business to these massive signature cakes for birthdays and showers and what they advertise as the best wedding cakes in town.

SPEAKER_00 10:19

Aaron Powell, which is quite the claim.

SPEAKER_01 10:20

Yeah. These are designs that range from understated elegance to completely over-the-top, multi-tiered constructions.

SPEAKER_00 10:27

So the menu presents a pretty severe dichotomy. Well, you have highly portable immediate consumption items on one side of the room and grand, monumental, highly fragile event cakes on the other.

SPEAKER_01 10:40

Right. So let's apply this to the WAC crew. You have 12 people on a tight schedule with five stops to go.

SPEAKER_00 10:48

Yep.

SPEAKER_01 10:48

I look at those mini pastries and bars like mid-marathon energy challenges.

SPEAKER_00 10:53

That's a perfect analogy.

SPEAKER_01 10:55

They are quick, concentrated bites. We need to fuel the group and keep morale high, but you absolutely cannot induce a massive sugar crash before stop 11.

SPEAKER_00 11:05

No, that would ruin the rest of the day.

SPEAKER_01 11:07

So it seems obvious that the group should completely ignore the massive signature and wedding cakes today and focus all their energy on raiding the mini pastries case.

SPEAKER_00 11:15

Well, from a nutritional and logistical standpoint, the mini pastries are the only viable option for the van.

SPEAKER_01 11:21

Right.

SPEAKER_00 11:22

The key to surviving a multi-stop tour is aggressive portion control.

SPEAKER_01 11:26

You have to pace yourself.

SPEAKER_00 11:27

A single mini pastry provides the exact spike of dopamine and blood sugar needed to bridge the gap to the next stop without causing that heavy lethargy that destroys the back half of a food tour.

SPEAKER_01 11:36

That makes total sense.

SPEAKER_00 11:38

Furthermore, a mini pastry is structurally sound enough to be eaten in a moving vehicle.

SPEAKER_01 11:43

Oh, logistics again.

SPEAKER_00 11:45

Yeah, it doesn't require utensils. It can be passed easily from the front seat to the back row. And most importantly, it minimizes the crumb radius.

SPEAKER_01 11:53

The crumb radius?

SPEAKER_00 11:55

Yes.

SPEAKER_01 11:55

The driver of that 15-passenger van will be deeply grateful for a minimized crumb radius. You do not want 12 people eating flaky croissants that explode into a thousand pieces over the upholstery.

SPEAKER_00 12:07

It would be a nightmare. But, and this is important, ignoring the wedding and signature cakes completely, that would actually be a mistake.

SPEAKER_01 12:15

Really? Why? You aren't going to buy a three-tiered wedding cake and try to wedge it into a cooler.

SPEAKER_00 12:20

No, definitely not.

SPEAKER_01 12:21

Yeah.

SPEAKER_00 12:22

But walking through their cake galleries and admiring the craftsmanship is a vital part of the Sim is experience.

SPEAKER_01 12:28

But why spend time looking at massive event cakes if nobody in the van is actively planning a wedding at stop 10 on a Friday afternoon?

SPEAKER_00 12:34

Because you were traveling with 11 friends from the Wisconsin Athletic Club. This is a tight-knit community, right? Over the next 12 to 18 months, the people in that van are going to experience major life milestones.

SPEAKER_01 12:47

Oh, I see where you're going.

SPEAKER_00 12:48

Someone will get married, someone will have a baby, someone will celebrate a massive anniversary or a milestone birthday.

SPEAKER_01 12:54

Right. Life happens.

SPEAKER_00 12:55

So looking at those cakes today is practical scouting. You are evaluating the highest tier of what a 2017 bakery operation of the year can actually execute.

SPEAKER_01 13:08

You are future-proofing your social calendar.

SPEAKER_00 13:10

Exactly.

SPEAKER_01 13:11

Six months from now, when the WAC crew is trying to figure out who to call for a centerpiece cake for a massive celebration, no one has to scramble or read random online reviews.

SPEAKER_00 13:21

You already have the answer.

SPEAKER_01 13:22

You can just say, hey, we know the place. We saw what they can do during box food tour.

SPEAKER_00 13:26

It anchors the bakery into the shared history of your friend group.

SPEAKER_01 13:29

That's brilliant.

SPEAKER_00 13:30

So the stop serves a dual purpose. You get the immediate sugar rush to survive the afternoon, and you gather vital reconnaissance for the future joys your community will celebrate.

SPEAKER_01 13:40

Wow. Okay, so bringing all of this together gives you a crystal clear blueprint for conquering stop number 10.

SPEAKER_00 13:47

It really does.

SPEAKER_01 13:48

You walk into 817 North 68th Street with an appreciation for the sheer endurance it takes to keep a bakery operating at an elite level since 1982.

SPEAKER_00 13:58

Right.

SPEAKER_01 13:58

You respect the systems the Corolla's put in place to maintain that legacy. Then you execute the cooler strategy. Dairy Tetris. Dairy Tetris. You secure Milwaukee's award-winning cheesecake immediately, utilizing the ice in the van to neutralize the afternoon heat and lock in that perfect water bath baked custard.

SPEAKER_00 14:16

And you handle the immediate fueling by deploying the mini pastries.

SPEAKER_01 14:20

Yes. Distribute those mid-marathon energy gels throughout the van to keep spirits high and the crumb radius low.

SPEAKER_00 14:26

Very important.

SPEAKER_01 14:27

And before you leave, you take a lap past the signature and wedding cake galleries, doing the necessary scouting for the next time your WAC crew needs to mark a major life event.

SPEAKER_00 14:36

And, you know, if someone in the van is already mentally planning that next event after seeing the display, they don't need to hold up the tour trying to negotiate a custom order right there at the counter.

SPEAKER_01 14:46

Right. Keep the line moving.

SPEAKER_00 14:47

They could just reach out to Simmons later. The number is 4142570998. Or they can just drop an email to info at SimmonsBakery.com.

SPEAKER_01 14:58

Perfect. So you grab your pastries, you load the coolers, and you slide the van door shut, ready to tackle the final five stops of the day.

SPEAKER_00 15:06

On to stop 11.

SPEAKER_01 15:07

But as the van merges back onto the Wawatosa streets, I think it's worth considering the broader perspective of this entire undertaking.

SPEAKER_00 15:15

The underlying psychology of organizing a day like this, really.

SPEAKER_01 15:18

Yeah. When you embark on a massive 15-stop marathon starting at 8 30 in the morning, relying on the hospitality of guys like Frank at Ballistraries, managing the complex geometry of coolers and pacing your sugar intake.

SPEAKER_00 15:33

That's a lot.

SPEAKER_01 15:34

It is. Are you really just there to taste the food?

SPEAKER_00 15:36

That's the real question.

SPEAKER_01 15:37

Or does the true flavor of the day, the thing you will actually be laughing about in the WAC locker room years from now, come from the shared endurance, the logistical victories, and the memories forged in a crowded van with eleven friends sitting right next to you?