Working with Your Best Friend with Swoon

So I would say, one, for anyone that's thinking about starting a business, I definitely recommend a partner. But even in the partnership, to really kind of be open with how you're feeling.

They actually say that having two founders increases the odds of a startup success 30% more investment.

In this podcast, we share how we grew a seven-figure food business out of our two-bedroom apartment in Chicago, all all during the height of a global pandemic and bring in expert entrepreneurs to share their stories and wealth of knowledge in business strategy and innovation. I'm Annie Slobodsky.

And I'm Morgan Lerner. And let's bite into business, shall we? Hello everyone. On today's episode, Running a Business with Your Best Friend, we are bringing in the special founders of Swoon, a zero-sugar Simple Syrup and Mixers Company, paving the way in the health and food and beverage industry. And like Annie and myself, Jen and Christina were best friends before they were co-founders. So we'll be talking about all the benefits of working with co-founders, specifically when they're your best friends, the benefits, the challenges, and the funny stories with it. So without further ado, let's bite into business, shall we? So for those of you that are just tuning in, it's maybe your first time here. Annie and I started this business, our banana bread business, back at the University of Michigan. We were neighbors in the freshman dorms and bonded over banana bread. We both grew up eating the beloved treat, and our grandmas had famous recipes. And we spent 3 years combining both recipes to create the most indulgent, tasty banana bread that just so happened to be made with wholesome ingredients. So that's what brought us here today, still best friends and business partners to this day. But you guys, Jen and Christina, I know you have a little bit of a similar story of being both best friends and business partners. Could you give us a quick explanation of how you guys got started and developed your partnership?

Yeah, so very similarly, we definitely started as friends. Um, Christina and I were in business school together and in the same section. Both of our last names are Ross, so we were seated right next together. Um, mine with two S's, Christina's with one. And honestly, it was just kind of friends from the very, very beginning, and it was and didn't even think of like, oh, let's start something. It truly started with— Christina is a huge host, and in business school you do a lot of hosting and going to people's apartments. And one day I was over at hers and she was making a mojito, like pouring in sugar and looking at me. And I'm like looking at her, I'm like, I don't want that. I can't have that. I'm type 1 diabetic. And she was like, oh man, I can't make this. And we were like, wait a second, like, who actually wants this? Like, all of our friends are like, can I have a vodka soda? How many limes can I add to it because sugar is just so bad for everyone and not just, like, for diabetics like myself. But again, we started as friends and even more so started, like, at a party with each other.

That's crazy. It's a very similar story. I love that we were both, you know, school kind of fate brought us next to each other for both of us. I would love to hear more about, you know, you guys obviously sort of came up with the idea together because you didn't want to drink a super sugary drink, but what do you think now that you're running the business together, the benefits are of having another person?

So many. I think one of the things that I've never gotten used to is just how up the ups are and how down the downs are. And so having a partner to really ride those roller coasters with you, to offer perspective, but also to feel as much as we feel when you're going, and it is, is invaluable. I think of it almost like a sibling. And when as a sibling, you kind of are frustrated about your parents or going through something with your parents that the sibling just doesn't need the context and the explanation. I think that that's sort of what having a true partner and co-founder is for me on the business. Someone who's willing to talk about it all day, every day, all the time, and never get sick of it, who's again really in the trenches and knows all the nuances and feels all the feelings around it is a huge support.

And so true. There's only one other person, the other co-founder, who can fully empathize in your role. Maybe someone else in the company could, but not maybe to the extent, because the co-founder and the founder experience certain stresses that only that role will face because a lot falls on your shoulders.

Do you think that you would have that same in it together sort of moral help if you guys weren't best friends first? Like, do you think you could have that same feeling of dependency in a good way with somebody who you just happen to go into business business with without that base?

You know, I think that's really hard to answer, and obviously a lot of other co-founders have done that, but I think the great things of starting as friends was like there is just that base of trust. And so, and, and kind of having, you know, shared experiences, but also kind of like a shared idea of what you want and shared beliefs in different things. And so I think because we didn't come at this from starting a business and it's like, what do you think, what do you think, we really kind of got to know each other organically and then felt that. So I think that's a nice piece that's just always there. Even if we don't agree on how to get from A to B, we definitely know where we want to go, get to be in the long run, and kind of have the trust that we both want the same things there. So we can have that discussion and kind of that back and forth and knowing that we want the same outcome.

It's funny you say that. One of the things that I think Morgan Lerner and I value so much in our partnership is what you're saying about how we think about things so differently. I definitely think that that's something that is a benefit of having a co-founder because you have somebody whose brain works so differently with such different perspective that just allows you to talk through those ideas. And I think that that's just challenging when it's not somebody who's an equal partner but maybe somebody that's an employee that's a lower level. I definitely think that's a pro there.

Yeah, I feel like it kind of goes, goes back to the basics of of teamwork, of how two brains come together and most likely reach a better outcome than if it was just one. Um, and we actually, digging into this episode, we found some really interesting data to support this. So they actually say that having two founders increases the odds of a startup success with 30% more investment. So ones with two founders get more investment, and then they have three times the customer growth rate, which is kind of crazy, and a higher likelihood that the startup will not scale fast. So scaling strategically. So a variety of, of real benefits and data to support the benefits of having another founder, which we thought was really cool and, and validating. But some other things that you guys touched on too that, that we totally agree on is in those tough times you have someone else that's supporting you. So I think, you know, COVID is an interesting example of— we've had lots of supply chain issues and price increases and shipping things that have really thrown some big business at us. And if it was one of us facing that with all the pressure on our backs, it would have been a whole nother story. But we had both of each other to go through that and come out of it stronger. So I'm, I'm very thankful in those moments to have Annie, especially because it's someone else to be that soundboard, that moral support beyond just two brains working together. Like you guys said, it's that support system too.

Yeah, absolutely. And I think we also try to have it translate to the team also. So given that Jen and I have— and I'm I'm sure you guys can relate, given that Jen and I have a personal relationship too. We try to bring that to the team. And we really believe that that sort of honesty and acknowledgment of having full lives and having moments that your personal life is clouding your professional decisions or making you just a little bit less focused and having a friend that you trust that you can tell that to who also is your partner that can step in in those moments and sort of be that lever back and forth we also try to translate to our team and ask them to also be very open with us and to that way be able to together tackle the problems and acknowledge people's lives outside of work and how that impacts their work at different points. So I think that's something else that we really value in our friendship is that we just care about each other and we care about what's happening in all of our lives. Different points in our, in our business, we've needed the other to step in more because of things happening personally. And that comes without any resentment and that comes without any judgment. Again, because you think of the person as a complete person.

Right, right. I think that speaks to the benefits of having a relationship with your founder and the benefit of that specifically, because there's a benefit of having a partner in general. But if you have that relationship, it's what you're talking about. I think there's that level of trust. There's some love involved, not just a business partnership. I like what you said about how it translates to the team because you have that empathy for life outside of work and work-life balance, um, which is really important.

I think that point of work-life balance too, for having a, a co-founder that is a friend specifically, we value work-life balance as well. So if something comes up with family or if something comes up with friends or you just need to take a few days off, I never have to worry about, you know, somebody steering the ship because it's so hard, as you guys I'm sure know, having a startup and being able to turn off at night or when you're on a day off. But having someone who you trust so implicitly to be able to step in during those times is definitely super helpful. I definitely echo your point there. Do you guys have any memories or points in the business where you think that, that, you know, something either crazy happened or work stress-related where you were gone, that the other person, you know, stepped in and really showcased that benefit?

Many.

Yeah, I mean, I think kind of like throughout the years there's definitely been stuff personally. You know, Christina's had kids, I've gotten divorced. Good and bad across the board on a lot of different things. And I think it's, you know, yes, those are the big things that kind stick out in our minds. And I think it's— the other one was always able to kind of like pinch in and be there. But I think the thing is, there are so many things that we're not really sort of like counting of, oh, I did this, Christina did that type of thing. It just is what it is. And I think it's that we do kind of are just going to be there for one another, right?

I think that's the beauty of when you have a really good partnership, is it's not— you're not counting. It's just an understanding and a mutual understanding. It's kind of a dance sometimes. Maybe there are periods where one person has to step in consistently, or for different things it plays to different people's strengths. So I think it's, it's a little bit uneven, and maybe a dance is kind of what I said.

Totally. And I think the other benefit of it is really being, as Jen was saying, synchronized on the sort of— I guess in friendship you would call it values, and in business you can call it values and goals. You can be very different. In fact, many of us are attracted to very different types of friends that push us in different directions that you can learn a lot from. Same in business, right? You kind of want to be two puzzle pieces versus two of the same thing. And there is this sense of whether you're pinch-hitting. Like, shoot, my daughter had a horrible time getting back in the groove of school this year and was just having a really hard time separating and going into school complete Dumbo style, arm over the teacher's shoulder, like, Mommy, screaming at me. You're sitting there shaking in your boots. And Jen and I have a call immediately afterwards. In our monthly board call, and I'm like, Jen, I'm just not— like, I am— I needed 30 minutes to, like, recover here. And, you know, Jen and I have prepped it. She knows how I think about things. She knows what my perspective is going to be at this point, and she can really step up to the plate and, and take the ball. Or when it comes to our team also, you know, we stand by each other's decisions. And so if someone gets to Jen first on something that typically I'm deciding on, but I'm out of pocket for whatever reason, that's the decision that we go with and we support each other in that. And I think that that definitely helps both internally and externally to have such a united front.

I joke sometimes, Annie and I say this, we joke that we're like a married couple. And what you said kind of reminds me of that. So the kids are getting to me, oh, you have to step in. It's— it goes beyond business. But I think we've learned a lot from that of just life skills and interpersonal skills and communication from experiences like that. Obviously, we haven't had kids, but similar, similar um, experiences. But what do you think you guys have learned if you had to take away a few things from being friends and business partners and just from a business partnership in general?

I mean, I think like one of the best things about having a partner and a friend is that there is one there. And so I think to really not kind of hide or like keep your feelings to yourself, like when, you know, as Christina was saying earlier, like it's great that someone knows the ups and downs. But I think also a lot of times when I'm feeling up, it might be when Christina is feeling down, or vice versa. And so you kind of at first might want to keep it to yourself of what you're nervous about or kind of what you have anxieties. But at the end of the day, there's really no benefit in that. And what I found is whenever I've shared that Christina has a different perspective, she can kind of talk me through it. So you're not sitting there and in your own head spiraling, you can have someone there, one, sometimes to spiral with you, but other times really to kind of pull you up and just kind of level you out. So I would say for anyone that's thinking about starting a business, I definitely recommend a partner, but even in the partnership to really kind of be open with how you're feeling.

Annie and I were just talking about that because we, you know, had some serious conversations with our manufacturer and those are some of the things that give us the most stress. Because in some ways it's out of your control, but it's literally the production of your product. So it's so important. And in those moments, it's often one of us gets kind of sucked in and maybe down, and the other person's like, it's okay, it'll be okay, it always is. So it's exactly that. And you need that sounding board to literally tell you everything's gonna be okay.

I feel like one of the other, like, learning lessons from working so closely with one of your close friends is the fun that it brings to the work is so incredibly valuable. Like when you're at a startup and you're working crazy hours that are just endless all the time, having someone who you love being around who makes things enjoyable, it just makes the work not feel like work. Morgan Lerner and I, I don't know if you guys know this, actually just went on QVC. The day was a little scary and we were getting ready to have our first TV debut And I was thinking the whole day, like, if this was just me and I was the only founder and I was like shaking in my boots by myself and no one was there to like make jokes or understand what was going on, I'd be freaking out. But we were like dancing in my kitchen and it was fun and scary at the same time instead of just being sort of crazy. Do you guys have any moments like that where, you know, big business things are happening, but the friendship sort of saves the day and making it light and fun?

One of the things that comes to mind is we were looking to package a product in a very specific, particular way. And so you go very deep into the R&D process, you go very deep into the science of the actual ingredients and into the manufacturing process and the sheer joy of going to a run and Jen finding a place that could do it and my being ecstatic. I remember I was at a dinner with some friends on a beach and it was this romantic, beautiful circumstance. She texted me. I was literally jumping up and down. Jen is in the middle of the country, like totally different vibes. And you know, you're like, oh my God, they can manufacture it. This is amazing. They got the hot fill process to be at 189 degrees when we thought they couldn't get above 186. And we did it, you know, like that sort of like very like specific kind of minutia that you get really deep into, but obviously is make or break for the business in terms of, you know, creating a quality product and sort of creating, you know, elements of on the R&D side of innovation that haven't been done before. And so I think those I definitely relate relate to is just like the, like, you know, right now we're all dealing with supply chain, you know, expensive freight and finding a cheaper freight option, and you're like, yes, it's as if I won the lottery. So I do, I do think it's both there for, as you're describing, to, to catch you in the moments where your knees are knocking against each other, but also to, to understand all of the, the building blocks and all the steps that it takes to to get a product out there.

That's so true. You face so many problems that you feel are sometimes unfixable in the moment, and then you get to the other side and you're like, yes, we got a solution.

Totally.

That's awesome. I'm like, which product was that?

TBC.

Oh, to be continued. That took me a second.

You guys, you know, because you are so close, do you think there are any additional challenges you face that other co-founders who don't have that external relationship may face. You know, to give you guys an example of something that Morgan and I were talking about is it's really hard to disconnect for the business. So sometimes, you know, we still want to have best friend nights and watch a movie and hang out, and it's so hard for us to like put the business in a box. And one of the things we say all the time— okay, this is the last thing, this last thing we're gonna say, and we say it like a thousand times because we can't, we can't put it away. Um, so is there anything like that that you guys struggle with as friends that are also business partners?

Yeah, I mean, I think that's very true and I don't think we've ever been able to put it away, but I think then the nice thing is that kind of whenever we're together or if we're like out, you know, I remember this summer we were both doing a demo and it's like, you know, when there were no customers there, it was just as much chatting about one problem with the business and then it was about something in our personal life and kind of just like that ease of back and forth. So I do think, yes, the, the negative of it is like you never turn off from the business, but at the same time you also never really turn off from the friendship either. And it kind of can just go so seamless. So I don't know if it's like, in the— at the end of the day, such a negative, but it's true.

It's, it's—

you're never gonna just be able to just hang.

That's so true. Some of the challenges end up being positives. It's like, okay, maybe it's harder to disconnect, but we have so much to talk about and it never ends. And then sometimes work doesn't feel like work.

It's—

we're hanging, but we're working, right?

Like, sometimes I feel like Christina are like talking over text, over Slack, DM on Instagram, like 3 different conversations. 2 maybe are about work, one's about personal, and it's just like all happening at the same time.

Yeah, I mean, I think in a funny way the negative impact might be on our personal lives and our friendship and our personal lives. I think the reality is I think there's only benefits on the professional side that I can think of. And I think it is something that we have to be super conscious of, just like you guys said, to remember we're also friends and we also have interests beyond swoon, which doesn't always feel that way. And again, I think that's probably our friendship may suffer a little bit because of that versus the business. So it is a good reminder that you all are suggesting. But again, I think there is this completeness, which again, I just liken to a sibling relationship, like the people who will know you and have known you for your entire life. I think Jen in that way is very kind of 360 friend for me. My husband always jokes with Jen that she's the person in his life that has the most impact that he never speaks to. Because again, like, I go to bed and I wake up talking to Jen, and whether we can do something or not depends on Jen, and whether I'm happy or not depends on something related to business decisions that we're doing that Jen knows all about. So he's like, I feel like I just need to call Jen more often to get a better sense of you, Christina.

Yeah, I think one of the other things, um, when thinking about challenges, and I think this could also be turned into a positive for sure, but when you have that personal relationship outside of business and it is harder to separate the two, sometimes you can take things more personally. You know, if maybe my work wasn't up to standard and Annie comments on something, it's easy for me to be like, oh, and take that personally. But I think what we've learned over the years is that's just when communication becomes extra key. So that's also, you know, whether it's siblings or— we joke about the marriage piece, it's like, that's because the communication is so key. So whenever we have an issue now, we get to the point, it's just, you know, you sit down and you talk about it, or we bring it up right then. And that's been such an awesome positive for us to learn that kind of over-communication, communicating about everything. So that's again kind of a challenge and a positive. I don't know if you guys can relate to that one.

I'm sure that's definitely, I think, true to all of these. The negatives can be, be turned into positives because there's, you know, they're double-edged sword, the good and the bad. But moving away from the negative, because I think it's clear we all think there are more positives than negatives, we'd love to hear a story, your favorite memory of working together. I know it's probably so hard to, to boil it down, but you can try and throw one or two out there.

I don't know if this was like a favorite moment of like working together, but a real like surreal moment was when Christine and I were out in New Jersey meeting with someone. We were at a coffee shop and had our product out there. We were walking back to the car and someone stopped us. They're like, oh my God, I love that. Like, this is amazing. Like, I haven't had a drink without sugar in so many years. And then when we told them we were the founders, she like totally lost it. And it was like, wait, they're talking to us? Like, a very much like pinch me moment. And it's again, you like work so hard on it. You like work on the product.

Product.

And then, but to actually like come to like seeing a customer, meeting customer in real life, and having them like love it is, is such an amazing feeling.

Oh, those are the most gratifying moments. It's funny though, you're like, oh, are you sure?

Me right here?

And then you're like, okay, 100%. We actually were at, um, Jen's house this summer, and her brother-in-law and sister had invited some friends over, and we were sort of sitting on one side of the porch, they were sitting on the other side, and somebody got up, went inside to the refrigerator, came out with a can of Swoon, and starts telling the other friend about Swoon and how, you know, "Have you tried this? This just started showing up in my grocery store," going on and on. And Jen and I were just chatting, and all of a sudden, I see Jen's ears perk up. She pops over, and she's like, "I'm so sorry. I have so many questions. I have to ask you more." So I think, again, witnessing those moments of, like, like, you know, we always joke and I really mean it, like, I don't think I'll ever stop holding my breath when someone cracks the can open and takes a sip. I don't think I'll ever stop being surprised that someone's heard of it or purchases it on their own. Experiencing that together and like understanding the like, oh my gosh, element of it together is extremely, extremely fulfilling. 'Cause you're like, oh my gosh, you saw it too. You heard her say that, right? Like, I'm not making this up. Like, tell me this is actually happening. I do think, you know, this is when you're deep in it and, and you're a founder, there's so many insecurities, there's so many questions that you have, so many decisions that you make, and you kind of just, regardless of what numbers are coming your way, you still feel like there's more to do, more to accomplish, more people to reach, more message refinement to make sure that what you really want to get across is getting across. And so having the ability to pull out every so often with your co-founder and celebrate those moments together means a lot.

Right.

Especially because you've worked so long and so hard on something, you know, back, way back to the college days. To see it, you know, come to life and in customer's hand must be so gratifying.

For sure, it really is.

I wanted to end the episode with a fun little thing. So for people tuning in, and this is totally on the spot, if you guys have any insider news or things coming up in the Swoon world or something you're really excited about, exclusive for the people listening, anything fun you could share as a little sneak preview review?

Yes, next month we are launching a new great fall flavor for my half-and-half lovers like Annie out there. I think it is gonna also suit your taste buds. So it is orange colored, the can. It is not orange flavored. It is very fall-like. And if you sign up for our SMS list, you will get true insider information and discounts. But no, we have a really exciting launch coming up in a few weeks. Wow.

I'm like, let me see.

I'm literally gonna text you right after this and get on that list.

We were slacking this morning as a team wondering if we heat it up and add a little alcohol, if it works. So just drop in, drop in some little pieces of knowledge.

Cocktail lovers, maybe with a side of banana bread, like, would be the perfect kind of pairing.

For sure.

That'd be a fun little content post, a pairing. We're there.

Oh, for sure. Okay, I'm telling you, the mug cake was so easy and delicious to make, and I was a hero with my kids. They got to put all the ingredients in themselves. They could eat the whole thing.

Totally.

Which is a real struggle in terms of someone who, who is trying to, to cut down on sugar for my kids. I'm like, yep, you can actually have the whole thing. So I think there's a good pairing in there for us.

Love that. Well, it's been so fun to have you guys. I'm so glad we got to do this. Thank you guys for tuning in today. And like we talked about, having a business partner is a true game changer. They help you through the tough times and can also complement your weaker areas, quote unquote, lead to stronger, better business outcomes, especially when they are your best friend, not just a business partner. And there may be some challenges, but the result is more more love, more meaningful memories that make some of the hard work not feel like work. And that is all for the episode of Bite Into Business. I hope you all have a wonderful rest of your day and week, and we will catch you guys in 2 weeks to talk about working with people to get what you want. Thanks, guys!