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I will say I've had many poor roommates over the years who have dealt with my kitchen antics.
I take over the entire kitchen and there's, you know, just powders all over the countertop.
Almond flour, hemp seeds, coconut sugar.
Caitlin Smith was a mad scientist on a mission.
She knew there had to be a way to make delicious snacks with healthier ingredients.
I didn't found this company to make money.
I squarely remember points in our history where I was like well, I could lose all of my money and this would still be worth it.
You've got to have incredible talent at every position.
It's like this huge push.
There are fires burning when you're going home.
Can you believe it?
Such an idiot.
And then you go back to, this is totally going to be amazing.
There are so many easy ways.
I have no idea what to do.
Sorry, we made a mistake.
But you have to time it right.
Oops.
Working out of a three-bedroom apartment.
Stuff that just seems absolutely nut balls.
Ten years later, we're like, well, that's just how you do it.
We haven't made it just how you do it.
This is Masters of Scale.
I'm Jeff Berman, your host this week on the show how Caitlin Smith grew Simple Mills into a better-for-you brand powerhouse.
From tinkering with recipes in her apartment kitchen to selling the company for nearly 800 million.
It's an incredible story of scaling with purpose.
Caitlin, welcome to Masters of Scale.
Thank you.
Thanks for having me this morning.
I've been so looking forward to this because I'm a longtime consumer of the products that you have brought to market.
And before we get to Simple Mills and the company that you've built and now sold, take us back.
Where does the origin story start on your entrepreneurial journey?
For me, it really started with changing up my diet.
So back in my early 20s, I was a management consultant.
I was traveling around a lot and eating a lot on the road.
And to be honest, I really wasn't feeling my best.
One of my friends suggested to me to take a look at my diet and change up what I was eating.
And so I switched to a primarily whole foods-based diet.
And with that, I mean, just everything changed.
And it was shocking to me how much our food affects.
And I'd been brought up believing that it affects your waistline, it affects diabetes.
But I think especially over the past 10, 15 years we've gained such an appreciation for all of the other things that food can affect as well.
And as I started to personally have this realization, I grew really motivated and inspired to help change what people are eating and really change our food industry.
And so I kind of set out on this ambitious mission for myself where it's like okay, how do I change what people are eating and make it easier for people to eat real food and eat things that are nutrient-dense?
And that's really where Simple Mills began.
It's one thing to have this insight to change your diet to have the experience.
It's another thing to say I want to help other people make this change in their life.
It's yet another thing to start doing it.
What was the first thing you did?
Probably the very first thing that I did was start working on recipes.
And I didn't know exactly where I was going just yet.
I was thinking about how to use the simplest ingredients possible to create nutrient-dense, easy-to-eat solutions.
I was thinking about.
Maybe it's meal kits, maybe it's an easier way of being able to cook salmon for yourself in the evening and a sauce that goes alongside that, or Or maybe it's a bread mix that can go alongside your dinner.
And so as I started experimenting more in the mixes and playing with different ingredients, then that's really where I started going down this vein of developing baking mixes that are made out of really, at the time, extremely unconventional ingredients.
If anyone knows anything about our brand, we make a lot of things out of almond flour.
So these mixes are made out of almond flour.
And this is a time where nothing in the grocery store is made out of almond flour.
I think it had just shown up as an ingredient on shelves.
And then I'm thinking about, okay, what do I sweeten it with?
And my mom finds coconut sugar on the Internet.
And I'm like, oh, cool.
This is a much better sweetener.
And so start developing these products in my kitchen, mixing things together, seeing how they react.
You're literally in your home kitchen doing this.
Yes.
This is my kitchen in Atlanta.
I will say I've had many poor roommates over the years who have dealt with my kitchen antics before.
I take over the entire kitchen and there's, you know, just powders all over the countertop that I'm playing with a lot of different ingredients.
And some of the things turn out, some of them don't.
And I'm asking friends and family to try like, oh, does this one taste better?
Does this one taste good?
And seeing what I can come up with.
What then, is the jump from being in your apartment in Atlanta playing with these new ingredients, figuring out recipes that will work, to actually creating a brand and showing up in a store.
How do you make that leap?
So many steps.
So, I mean, I'm doing everything from researching how to create an ingredient label and FDA rules.
I'm learning the FDA rules.
Literally going on the Internet to research this.
Yes.
Yes.
Literally Google, searching how to create even just an LLC, searching how to find a commercial kitchen in Atlanta because, of course, to manufacture products that are available for sale.
They need to be made in a commercial kitchen.
I'm researching how do you get into retail stores and how are products delivered?
And so, for our first customer was my local Whole Foods store, which was the Whole Foods Ponce de Leon store in Atlanta.
And I called up that store's, like you know, maybe five minutes from my apartment, and asked them OK, how do you get in here?
How do you get into Whole Foods?
And the store buyer is like, well, you come down here and you talk to me.
And he's like, you want to come down on Thursday?
And I'm just in the research stages.
I don't feel like I've got a complete recipe or anything.
But I don't think you ever really feel ready as an entrepreneur.
And so I say, well, I'd love to come down and meet with you.
But how about Saturday?
Now, the background here is I'm still working full time as a management consultant.
I'm flying every Monday, flying back every Thursday.
And he says, sure, yeah, come down and meet me on Saturday.
So...
I meet him on Saturday and bring him some baked muffins and he tries them and he's like these are really good.
He's like, that mix made these muffins.
Like, yeah.
But he couldn't believe that those simple and nutrient-dense ingredients could create something like that.
And so he's like, all right, let's get you in here.
And so started all the paperwork, which takes a while.
And at that point, Caitlin, did you have a brand?
Did you have a label?
Did you have a commercial kitchen?
Like, were you there already?
Or was it like you got the yes and then you had to figure it out?
I had developed a label on Facebook.
I don't know if this website still exists, but it was called 99designs.
So you could basically crowdsource logos and crowdsource package designs, and all of that for a low cost.
So I kind of rigged up my printer to be able to print the package designs and got this like massive ink cartridge from China, just to keep the cost down as much as possible.
The least organic thing that you were working with there.
Yeah.
I mean, you just like do these crazy and creative things to just try and figure out like I need to put this into a package.
As far as commercial kitchen, I did start searching then for a commercial kitchen.
I mean, getting into Whole Foods at the time took four months just to get into that one store.
Because of the paperwork and the approval process and all of that?
Yeah, exactly.
How big is that first order from that one local Whole Foods?
It's probably something like four cases, maybe eight cases, where a case has typically six units to it.
Okay.
So it's not a huge order.
Not huge.
The toughest part was actually trying to figure out how much I would need, because that's an initial order.
That's like just to get product on the shelf.
But the question is how fast do the items leave the shelf?
And so I found a contract manufacturer up in the Northeast to help me manufacture it.
It's like what size order should I place and how much?
You know?
How many pounds of almond flour should I send?
So I remember, after that manufacturing run, getting all of it back to Atlanta and looking at it and just thinking oh, I made way too much.
Oh, I made way too much.
This is going to go bad.
So then my parents were like pawning it off to our friends and family.
And then like two weeks later, I was like, oh my gosh, I don't have enough.
Oh no.
Because that first run at Whole Foods sold out quickly?
Yeah.
We sold through it a lot faster than I anticipated.
And we also started adding on other Whole Foods stores in the region too.
So you know, dialing in how much to make and when, especially in those first couple of years, and then also funding the working capital for that.
Because, of course, you don't get paid the day that Whole Foods receives the order, so you're floating money for a period of time, like it was very hand-in-mouth.
I ended up selling my car and uh, maxing out all my credit cards and spending all my savings just pretty much on working capital.
Wow, were you also going to friends and family to get them to start putting up money, like a lot of entrepreneurs do, or was that not part of the journey there?
Well, the funding journey started a little bit later.
So one thing we haven't talked about just yet is I at the same time that I started Simple Mills, I was also applying to business school.
And in my mind they were like these two completely independent things that didn't really have anything to do with each other.
And it's just kind of what you do as a management consultant several years in.
And so I went up to Chicago to go to the University of Chicago, their business school, Chicago Booth, and started at Booth around the same time that we were going into our first stores.
So we're probably in something like 10 stores when I start at Booth.
And in my mind, the business was always number one.
So like in order of prioritization, if something had to fall, It was never the business.
And so I was taking courses that let me work on the business.
Like I would take entrepreneurial selling.
I would take accounting because I was also doing our QuickBooks and trying to figure out how on earth you classify these transactions.
And one of the classes I ended up taking was the New Venture Challenge course at Chicago Booth, which the focus of the course is fundraising, and I get in the course and I'm like that's all great.
But like, I don't, I don't really need to raise money.
Because why, why didn't you think you needed capital?
You know, it was obviously really naive, but I think that for one, I really underestimated what it takes to build a consumer brand, and particularly the marketing investment and also what things cost.
Like it's one thing to make things on a, I don't know, printer in your living room.
But as you scale, a good package design is an example.
Doesn't cost what it costs on 99designs.
And having a really good package design is something that is really important.
It is your number one marketing vehicle as a consumer brand.
So there was the underestimating what things cost and what was needed.
But I think also really underestimating the working capital requirements of the scaling brand.
And so I had just kind of this perfectly little built model that as a consultant does.
And I was like, all the money we'll ever need is $200,000.
And I had like a family friend who was like, oh, yeah, I'll give you $200,000 for that.
And so I was like, I'm set.
I don't need to raise money.
But as I would have it, the deal with a family friend fell through.
Hmm.
And that was really heartbreaking on multiple levels.
And I think around that time, I was starting to realize just how much money we were going to need.
And thankful to the coaches at Chicago Booth who were helping me realize that we were going through the PLs of public food companies.
And they're like, look at how much they spend on marketing.
I mean for a sense of scale for your listeners.
I mean a lot of times to watch A single brand or a single product line.
In some of these CPGs they spend 50 million.
Yeah, five zero million dollars.
Yeah, it's not like my like $200,000 is going to cover working capital and everything else.
And I don't know salaries.
I guess I didn't think I needed any people on the team.
Well, and also to your point, your earlier point about Whole Foods so frequently in these CPG deals you're not getting paid on the purchase order.
You're not even getting paid on the delivery of the product, right?
And so you are fronting a lot of capital here.
So you've got a lot on the line.
At what point do you say, oh, shoot, I'm really going to need a lot more money to get this done?
I think it's right around that time that the deal falls through with a family friend.
My parents end up, they were really upset about this because they've been a longtime family friend.
And I come home and tell them this and they decide to mortgage their house and give me $200,000.
Whoa.
Yeah.
It's a big bet.
Yeah.
Still ahead how Caitlin Smith built her team, scaled Simple Mills and eventually decided to sell the company.
This is Mike Nicholas Capital One, business customer and co-founder of Ansett Uncles, a plant-based restaurant and community space in Brooklyn, New York.
And he's telling us how they started a product line.
We already had a space in the community.
The food was an extension of our lifestyle and our values.
So we know we wanted to create something that was an offshoot to that.
Our pepper sauce, that's my grandmother's recipe.
That's like a liquid gold, right?
If someone wants to approach us and ask us, what do we do?
We provide flavor.
Growing a product line is no small investment, but Mike and his wife and co-founder Nicole, were able to manage with the help of their Capital One business cards.
Working with Capital One Business, we're able to leverage our limits and utilize those points, making sure we can continue the scale at the speed that we need it to go.
To learn more, go to CapitalOne.com slash business cards.
Welcome back to Masters of Scale.
You can find this conversation and more on our YouTube channel.
And be sure to check out the link in our show notes to subscribe to our newsletter.
Before the break we just heard that Caitlin's parents had mortgaged their home to give her 200000 for the business after a deal with an investor fell apart.
Did you have concerns about them doing that?
Oh, yeah.
I mean, we ended up raising our first round about four months later.
And when we raised the first round, I actually asked that half of it get paid back, because it's so stressful having your family's money on the line like that.
Sure.
Yeah.
What was that conversation like with your parents when they said we're so upset about this family friend deal falling through and we want to mortgage the house and give you the 200?
They were just determined to do it.
They were angry.
I think I, more than anything, I was kind of resigned.
I was like, oh, I guess this happens.
And they're like, this is not okay.
Like, he's trying to renegotiate this deal because he sees how well you're doing.
So you take the $200 from your parents.
What happens between getting that capital and raising money four months later?
I started talking to people left and right and left and right.
And it's hard getting funded the first time as an entrepreneur.
It's also 2012.
It's become a lot easier to get funded as a consumer business in the past 10 years than it was then.
But at the time, everyone just wants the tech unicorn.
And so why am I going to invest in a baking mix company?
Well, I think this is really important and hopefully helpful for entrepreneurs who are raising money in categories that are not AI, for example, right now.
How did you figure out who to pitch and how to tailor the pitch so that you would have a shot at raising capital in a category that didn't have a wealth of investors rushing into it?
I think casting a wide net first and foremost.
I mean, I was talking to probably eight different investors every day.
I do think that another aspect of this is really kind of looking at the angel investment space, because all of our initial investors and in fact for a long time, like our first three rounds were all angel investors.
They're the same people who who just kept coming back.
And there's something about angel investor groups where they can take a little bit more of a passionate and liberal approach than perhaps a group that's focused on something really specific.
That also gets a lot of high demand to it.
And so those angel investors really turned out to be a big deal.
But talking to that quantity of investors, I think was a big part of our success in getting funded.
And just to give you a little bit of an anecdote on this, I had talked to so many investors that the way that we got our lead investor which finding a lead is, I think, the key to getting a successful fundraise done.
He goes into a Whole Foods store to look at our product on shelf in Charlotte, North Carolina.
I live in Chicago.
He looks at the woman next to him, asks her, what do you think of this brand?
And she says, I'm looking at investing in it.
Stop.
Yeah.
So it is, at the point where I have talked to so many potential investors, that two potential investors are standing side by side in a Whole Foods store in Charlotte, North Carolina, talking to each other about the fact that they're interested in this brand.
Wow.
Did they both come in?
She did not.
But he he called me up later that day and he's like I want exclusive rights to take a look at this deal for a week.
And I said, yes.
And at the end of that week, we had a term sheet and we're moving toward a signed agreement.
And how much did you raise in that round?
A little bit over two million dollars.
How did raising that two million change the business and change what you were doing?
What happened once you got that capital?
So raising that money really, it enabled us to level up a little bit what we were doing.
To give you a sense, in our first call it eight years of business.
I think we raised less than 10 million.
Hmm.
So we've been extremely capital efficient over our history.
So we're not kind of going out and getting fancy office spaces.
We're not going out and paying crazy salary packages to people.
But we're doing the stuff that really matters.
So we did invest in a new package design, which is, you know, we've had iterations throughout our history, but it's largely the package design and brand that you see today.
So this was a large investment.
I start hiring team members for the first time.
And I start with some junior team members and then also identify some experienced talent that I could bring into the team and really help me grow my understanding of the consumer product space better, which was just huge.
We start leveling up our manufacturing operations and also getting our first full-time salesperson, who knows the space well.
It enables us to do the fundamentals.
Caitlin, beyond building out the team, I'm curious about the role of being at Chicago for business school.
What role that played in this?
A lot of entrepreneurs who are experiencing the journey that you're on might have considered dropping out of school.
Well, I did drop out after the first year.
Once I raised money, our investors were like, so you're not going to keep doing this, right?
And the answer was right.
I'm not going to keep doing this.
So was Chicago the right choice?
Should you have gone and spent a year in Chicago?
Or, in hindsight, do you think you should have just powered through with being an entrepreneur without business school?
I suppose.
First of all, I think that so many things happen because you're in the right place at the right time.
So I couldn't go back and change that.
I would not go back and change that because fundraising was so much easier having been at Booth.
Even the courses that I took, like entrepreneurial selling, super helpful.
It was also a great opportunity to take a break from my career in a safe environment where it's not like I was backtracking on my career, but also gave me the space to really explore what this could be.
So I wouldn't take that part back.
I also wouldn't take Chicago back either, in that I didn't realize just what a ripe consumer brands environment I was stepping into by choosing that city and that school.
There's probably no better place in the United States to recruit consumer talent.
Why is that?
The business schools there focus on it.
It's also where a lot of the large CPGs are located.
And this maybe I would share for future entrepreneurs, being where the talent is, is huge.
And also affordable talent too.
Some cities can be extremely expensive.
And so your dollars, it will go so much further in a city like Chicago.
It strikes me that in those first several years, as you were building Simple Mills and You went from what even is coconut sugar and where do I get it to an increasingly crowded landscape of I guess we'd call them maybe better for you brands.
Were there moments where you hit challenges because that marketplace was getting more crowded?
And how did you figure out how to keep breaking through with your products without exorbitant marketing budgets?
I think for us, the most important thing has been the product positioning from the very beginning.
And that what I wanted to create, and continue to create today, is these products that are made with astounding ingredients and putting them into delicious tastes and forms that consumers love.
And so using these unconventional ingredients like almond flour and crackers or We've got cookies made out of watermelon sea flour or, a couple of years ago, we came out with these cheddar pop-ums, which are like these snackable cheddar crackers made out of butternut squash and red bean.
And so as a food product, first of all, must taste great.
And, second of all, when you're able to offer a lot of benefits on top of that, which is a stunningly simple ingredient.
To act and ingredients that work hard for people is kind of a no-brainer.
Take us forward to late 2024, early 2025.
You made a decision to sell the company.
Why?
Oh, you know, I think that throughout our history, my goal has been to make this as large and impactful as possible.
So one of the things that I tell our team is that The larger that we grow, the more impact we're having, both in terms of the crops that are grown across our country and across our world the impact that we're having on more people.
And as we thought about partnering with Flowers, it opened just our eyes to so much opportunity to expand in ways that we could not do on our own.
What's an example of that?
So I think that one accelerating our distribution, getting into more stores which, to your point, on a crowded marketplace, that is something that's really important.
And also important as you see your competition making moves like this too.
Another is continuing to accelerate our innovation pipeline and putting the right resources against that.
I think another is we increasingly... are able to and are focused on reaching a broad consumer base.
And so being able to reach that broad consumer base versus, just as I put it, the people like me who are already trying to make good decisions with what they're eating.
So we just saw so much opportunity in it.
And also, it really helped that we got to know Flowers over a number of years.
I've known Ryle as the CEO for over five years at this point.
And the cultural match between our organizations, the degree to which we see the world the same way, the degree to which he's excited about what we're doing and our mission as an organization.
It was just a really wonderful fit in a way that a lot of times these things aren't.
And so we just became more and more excited about it.
I mean, I didn't found this company to make money.
I squarely remember points in our history where I was like well, I could lose all of my money and this would still be worth it.
How has your role changed now that you're part of a bigger company?
In some ways, my role is very similar to what it was just continuing to craft the vision and future of our organization, motivating our team.
But I think that the context within that changes and that when you have a partner that has new capabilities, new things that you can take advantage of, new potential, there's a world of opportunity that needs to be assessed and figured out.
You and your leadership team have to figure out what that means for your organization and your strategy.
And so it's very exciting in that way.
It's also, I think I kind of expected you get on the other side and you're like okay, I get a moment to breathe.
And I think it's been kind of the opposite, because there are so many exciting things that you could do together that you have to kind of figure out how to moderate at the right pace.
Yeah.
Entrepreneurs who've had these kinds of exits talk about where the exit is not the end.
It's a really important step on a journey, but it is just a step on the journey.
Yes, that's very true.
Caitlin having now sold the company for nearly 800 million, if I'm not mistaken.
Can we go back to your parents taking out that mortgage and giving you the first 200000?
When you called them and said, mom, dad, guess what?
How did they respond?
They're mad that I made them give $100,000 back to the other investors.
They're like, it would have been double.
They're like, we would have kept it in there.
I'm like, I couldn't have tolerated it.
Oh, how great.
That's perfect.
Caitlin, you are a premium food brand, premium grocery product.
You have navigated through COVID.
You've navigated through some rough economic times.
How do you do that when you are a more premium brand?
It's interesting for me.
This question goes back to culture, because I think that having an organization that is rooted and can move through change and ambiguity well is such an essential element of success in these times of great change.
And so one of the things that we have done over our history is looked at each of these large events, and there have been a lot of large events.
You talk about COVID.
I think another one is there was just mass supply disruption.
And how do you take these situations and not just make it through them, but see the opportunity in them?
My favorite book is The Art of Possibility.
And it's really just that.
It's thinking about like okay, reframing these things that come across your desk, and what is the opportunity in this?
And so, if you think about something like mass supply disruption that followed COVID, we really took a number of measures proactively to To prioritize being in stock.
We maintained something like a 96 fill rate when competition was happy to be at 80, meaning we were filling retailers' orders.
And that really built our relationship with them.
It also meant that our product was on shelf when other items weren't.
And so it really enabled us to grow during that time.
Use that just as an example of, you know, looking at these things opportunistically and thinking okay, what can we uniquely do here?
What are we positioned to do that could enable us to win in this environment?
What's a lesson from art of possibility that has stuck with you and you have infused into the culture of simple meals?
One of my favorite things that talks about is uh, Michelangelo used to look at a block of marble and think that is a beautiful statue waiting to be carved.
If you can look at people that way, if you can look at situations that way, it really opens you up to all these different options that maybe you didn't see before.
An early stage founder bumps into you walking down the aisle of a Whole Foods where Simple Mills products are on the shelves and says, oh my gosh, I'm such a fan.
I've just started a business.
What's one piece of advice you would offer me?
I think that the openness to learning is just absolutely critical.
So I had an advisor early on who told me that being an entrepreneur is one of the most downwardly mobile professions out there.
And what she meant by that is that if you're successful, then at some point your job will outgrow you.
And for me, that really honed me in on the degree to which I needed to be constantly learning and changing.
And so it does create this curiosity of okay, what is the next thing I need to be learning for this stage?
And I'm not the same person, person that I was two years ago, not the same person I was five years ago, 10 years ago.
And also, by the way, all of those versions of me couldn't have done what I'm doing right now.
But also this version of me right now.
I'm not sure could have done those things 10 years ago either.
So it's adaptation to the time and continuous expansion of what I call your toolbox.
Like if you could imagine that you're walking around with this bag of tools.
Over time, you can add more and more tools to that.
And you can be a lot more conscious about which tools you pull out at what time, which enables you to be a lot more effective as a leader and enables your organization to grow and change.
And, by the way, not just you but also your leaders have to do that too, which means that you have to be concentrated on their growth and development so that they're making the next leap and the people under them are making the next leap, which is a lot easier said than done.
Yeah.
Caitlin, wonderful having you.
I love that as a place to close.
Thank you so much for being on Masters of Scale.
Thank you for having me.
Thanks again to Caitlin Smith for joining us.
The driving force behind this scale story is a simple one.
Caitlin believed there had to be a better way of doing things.
Whether you're baking snacks, building apps or looking for a problem to solve, that belief can carry you a long, long way.
I'm Jeff Berman.
Thank you for listening.
Meet Emily Worden.
Capital One business customer and owner of Emily Worden Designs, a handcrafted, fine jewelry store in Richmond Virginia, that got its start in a dorm room.
I said I was going to try it for a year.
I signed up to do craft shows.
Trade shows got into a few local boutiques and then things just picked up from there.
Emily's steady success at trade shows gave her the capital she needed to invest in a storefront.
Every cent that was made was going back into the business.
I was nervous that we weren't going to get enough traffic, but we had a huge turnout.
With Emily Warden Designs firmly establishing itself in the Richmond community, Emily would need to significantly increase inventory in order to keep up with demand.
And she looked to her Capital One business card for support.
The purchases were so high, I needed to get a business credit card.
And I looked at Capital One.
The options and the cash back was so amazing.
It gives me even more of a push to take a leap in getting one or two extra stones because I have that extra cushion.
To learn more, go to CapitalOne.com slash business cards.
Masters of Scale is a Wait What original.
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Associate producer is Masha Makatonina.
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Mixing and mastering by Aaron Bastinelli and Brian Pugh.
Original music by Ryan Holiday.
Our head of podcasts is Lital Molad.
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