233. Go Solo or Find a Cofounder? Choosing Your Founding Path

0:01Welcome to Startup to Scale, a podcast by FoodBevy. I'm your host, Jordan Buckner. Join me as I talk to aspiring entrepreneurs, seasoned industry experts, and everyone in between as we unlock the keys to growing from startup to scale.

0:18Being a founder is one of the most rewarding and isolating journeys that you can have. In this episode, I'm sitting down with Howie Sheriff to explore the emotional and strategic decisions behind building a business alone versus being on co-founders. We'll talk through both sides of the conversation and unpack how to know if you're meant to build solo or with a team, the pros or cons of going it alone, and what to look for in a co-founder and what to avoid. Just before we get started, I'll give a little shout out to our FoodBevy Insider Boxes. We just dropped our Fall Edition, which is available at insider.foodbevy.com.

0:57It's the best way to taste and explore all the newest CPG launches that are going out right now. We have my favorite new product, June Pistachios, Mark Samuel's Kettle Chips that he launched, David's Protein Bar, IQ Bar, and a ton of other products. So definitely check that out. So to today's conversation, Howie, welcome to the show again. I always love having you on. We have a blast hanging out together.

1:23Howie Sher:We do, and I appreciate the invitation, Jordan. Great to see you again. So to set the stage a little bit, you have ran your own CPG brand. You come from a family business, and right now you help dozens of other CPG founders navigate the growth challenges in their business. And on my side, I have run multiple companies, done that solo, had co-founders, and so I'll be sharing some of my experience as well. But Howie, for you, tell me a little bit about partnerships just in the businesses in your experience and what that looked like from family businesses to solo. Sure. Everybody has their own unique journey.

2:07Howie Sher:And mine started in family business. I was fortunate enough to see two generations in the lunchroom when I'm 12 years old. And there would be certain circumstances that come up in me with my wide eyes and some of the words that were floating around I had never heard before. So that's unique. But my experience in the supermarket space and growing up in the grocery store, I've always said I keep my youthful energy from a revolving door of 16 to 18-year-olds, that it's their first job. And me as a 12-year-old, when it was my first job, the respect that I knew that I had to give that person of my age in aisle four, that it's an open area.

2:49Howie Sher:Me thinking of it as if aisle five, you can hear me. And me respecting grandma in aisle five brings me to a place of partnerships and co-founders. if someone's going to get into a business and launch a brand. The value of different skill sets, different life experiences, different perspective, someone to lean on, someone to laugh with, someone to cry with. I believe as having attempted to fly solo, how lonely that is. At certain times of every day, there is great value to creating partnership and you have to give the other people grace and space in order for them to offer up their unique skill sets, their thoughts.

3:37Howie Sher:It can't always be what you think. Grandma's right over there in aisle five. And how I say this to my peer, how she receives that, I need to be very aware of. Someone's always listening. And if we approached life in a way that we're talking to each other, that there's that third person there to hear how I'm saying it. I think there's great value to that. I like that start. Now, Howie, most people who I meet end up starting a business alone, maybe with another person. And so what's even the point of having a co-founder and what does it mean to have one? So I'm big in analogies and think about getting on that roller coaster.

4:18Howie Sher:You have the safety bar that comes down and clicks in place. And there are times where you're on that ride by yourself. Just imagine the twists and turns that come along with the excitement of that big dip. There's something special about looking over at that person and seeing the smile on their face or that moment of surprise where I don't know if I can do this anymore. That having somebody else to lean on, and you know, you said it in a singular way. When people ask me, should I, shouldn't I have co-founders? I put an S on the end because I'm a big believer in an odd number because there's certain things that are going to creep up from time to time, that odd number is going to break the tie.

4:59Howie Sher:You're not always going to agree with one other person. And sometimes that leads to not comfortable. And with your business and you're looking at what are your nuts, did you decide to go in that solo or did you think about bringing on business partners? From the very beginning, my legal advisor, that's my bronco, sometimes he feels like my brother and sometimes he feels like my uncle. Unrelated, but definitely feels so because he cares about me and he realized at the very beginning my layer of empathy. And let's do this. Let's ask ourselves, who are we and how are we wired? And we're looking at bringing other people in.

5:41Howie Sher:Who are they and how are they wired? Have you known them for a long time? Have you just experienced grade school, junior high, high school with these people? Or did you meet them in the professional space? These things need to be considered, but it starts with you. And I started What Are You Nuts with great desire to bring others in. But my layer of empathy at the beginning was probably too thick because I wanted to wait till roots grew under the ground to hold that thick trunk that created the branches and leaves growing off before I brought others in. And before I knew it, I turned around and it's eight years later.

6:21Howie Sher:And I want to say, had I begun with two others, it would have given Woody and Nuts a better opportunity to still be here. And I'm not saying that's a guarantee it would be because you have other factors that are involved, but I will tell you, I believe we would have been better served as a brand, as a company. And I had outside investors. I had advisors and consultants that I brought in, but from the day-to-day employee perspective, it was just me. Let me tell you, Howie, on my side, my first real company, my first registered LLC was a meal kit delivery company called Chopbox. And with that, I started on my own.

7:01It's kind of like a blue apron or plated when those were big. And I didn't even think about a business partner quite honestly at the beginning. And I did everything myself. Like literally I was updating the website. I was doing all the marketing, finding customers. Actually, I worked at a commercial kitchen, right? Where I'm like chopping up onions and garlic, putting together recipes, photographing the meals, delivering them to customers around Chicago. And like literally, if something had to be get done in the business, I was doing it. And after a few months of it, I was like, wow, like, this is all the work I'm burnt out.

7:39We had zero investment is all just my own savings. I was funding off of it. And I had the feeling of like, I could really use someone else's help to do this with. But I did not have enough cash at the beginning at that time to hire someone kind of full time. So it was in this conundrum of thinking like, wow, I need someone essentially to help me run the business to have as a partner in this that I could trust. But I also don't have a lot of money. And so when I ended up pivoting that business and going into my CBG product, T Squares, I did like the opposite. I found three co-founders to start that business, and that was T Squares.

8:25And at the time, I was like, I don't want to do this alone so much. I'm going to basically bring on all these people as a team. Now, one of them worked kind of day to day in the business and two more as a strategic level, but we meet every week to talk about all the big decisions. And so I saw things from both sides of being a solo founder and from having a large number of co-founders in the business. And there's definitely, you know, implications with each of those and seeing kind of how that led.

8:55Howie Sher:And when you were a solo founder, didn't you find yourself gravitating to what you enjoyed most as to what you were doing first and the things that you were uncomfortable with didn't get as much of your time attention or your brain power? Like you find yourself kind of going through the motions, doing the best that you can. I definitely did. Right. And one thing that really stood out at one point was I want to do everything from behind my computer at first. And it's like all the marketing. And then I realized like, okay, this isn't actually driving the growth that I need. And I forced myself to like go.

9:32Yeah. Right. Like set up an apartment buildings in Chicago, in the lobby when people were getting home to give them samples of food to try it out, right? And it was like way out of my comfort zone. So it was like the good thing, I didn't have anyone to lean on, so I had to grow there. But at the same time, as you mentioned, the stuff that probably needed to get done that I wasn't skilled at would always take a backseat. I'm curious as well, like from your perspective in talking and meeting with a lot of founders, some of the long-term implications of having a co-founder in the business. And if you've seen good relationships, or relationships sour over time as well.

10:11Howie Sher:Both. And I'm going to tell you, not enough people concentrate on the beginning. Even when they're at the beginning, just the core and the essence of what I mentioned earlier of everyone shows up with their own persona, with their own tendencies. And if you've not experienced each other in the workplace or when things are tough, and it's only fun and games that you know each other, that's going to be a tough one for me to suggest it's a good idea. But you really have to be honest with each other and do some role play of knowing there's going to be a lot of unknown. It can't be specific role play.

10:45Howie Sher:But should we come upon challenge, let's set up a gold standard of how we're going to address it. It doesn't have to be Robert's rules, but it needs to be agreed upon. It can't be expectations that we're working off of. And again, the respect of they're bringing in a different skill set. They're not you. And you need to get out of your own way to believe that maybe it's more of your dollars or more of your knowledge or more of your instinct that overrides theirs. If you're already there at the beginning, you're finished. You need to put that all over here and at the very most, meet yourself halfway and let them in.

11:26Howie Sher:And if it's two other people, meet yourself one third of the way. It's not all about you. You're not that smart. You're not the king or queen. You need to allow people to express themselves. You need to create a safe space. You mentioned you do a weekly check-in with each other on the critical points of the business. I ask, did you have an equal amount of time for personal time with each other to just go bowling or fly a kite or walk or eat together without talking about business? That's off limits. Because if you don't, it's going to be more likely that you head down a path of sadness and brokenness.

12:04I hear you. I think one thing that I learned very early as well, as you mentioned at the beginning, is about setting expectations and understanding your own as well. Because I think when I went into those relationships, I had an expectation that my business partners would put in the same amount of time and thought into the business that I thought I was doing at least. And for some of them, they were like working full-time jobs, but it was an unreasonable for me to expect that of them, especially if I didn't express that. Right.

12:40Howie Sher:That's why I'm just going to interject. Yeah. You can't have any partnership based off of expectations, not a life partner, not a spouse, not a business partner, truly not a friendship. If it's going to be a great one, you need to make agreements. Expectations create pain because you're thinking in your head and then you're showing up with what you're thinking, that's an expectation. If you speak of it and say, can we agree to this? That's something more real and more tangible because they have their own expectations. When you're showing up with yours, let's get that word out of our vocabulary and out of our thought process.

13:17I think that's so good. Those unspoken expectations can destroy any relationship, as you mentioned. The other thing that I think is so important as well is when you bring on a co-founder, what you're really doing is giving or selling part of the ownership of your business to somebody else. And I can tell you from experience that we have to go through a restructuring. It's almost impossible to take back ownership or re-divide ownership in the future. And so if you don't think about, it's not just bringing on a partner, It's actually bringing, you know, giving away or selling. So an earning part of the business that you no longer have.

13:56And that ownership is hard to get back. So I think that was a really tough thing as well.

14:01Howie Sher:I hear you. And I think as founders, singular, sole proprietor, if you're going to bring somebody else into your mind as a possibility, as a partner, you're not giving anything up. You're earning their knowledge. you're earning a layer of respect to you if they want to go into business with you get out of your own way this is them putting something else aside to apply their knowledge and their skill and their experience with you not for you they're not giving you you're partnering together to build together to experience joy and pain together and that's the mindset you hope that people come into a partnership with.

14:44Howie Sher:And it's the rarest of rare that this doesn't have to be coached or advised because this is not a natural thing, especially when you have in your mind your idea. Unless at the same exact time that both of you thought the same exact thing to bring this food or beverage to market, that doesn't happen. It's typically an idea that then gets fermented and grows in a way that you're sharing your thought with someone else, I'd like to do that with you. You're exciting them and they want to apply themselves to this. And this, that can't become you either. A friend once told me, if you're making t-shirts, you're not the t-shirt as much brain power as you're putting into bringing that t-shirt to market, selling millions of those t-shirts.

15:33Howie Sher:You're not the t-shirt. You are a human being with feelings, emotion, ideas, not to the list you're not a t-shirt i love that i mean in thinking about that i know you've had experience on this side right like being a solo founder can be lonely and what are some of the biggest emotional challenges that founders face in those early days of the business they're growing so being fair to everyone that's listening to this i show up as a cpg founder age 40, married with three children, none of which I knew they were going to college or hoping they would go to college. They have their next chapters. But here I am thinking the fifth generation is going to have the same opportunity that I did working with my best friend, my dad.

16:20Howie Sher:That was removed. And here I am to launch a product. Everyone that's listening has their own journey and where they show up. So as a 20 something or early 30 something or even 40 single person that doesn't have a life partner in place or children dependent upon them. That's very different than the experience that I lived. I'm working with a couple founders today that are rising seniors at a university with this incredible idea that they're wanting to bring to life. I have another set of co-founders that are also the same age and their products already on market. They're at a very different place at a very different pace than 40 year old Howie was.

17:01Howie Sher:So you have to start with who are you and where are you and how are you wired? What's your makeup? How much are you anxiety ridden just as you are as your daily being when it's deciding what you're going to have for lunch or now it's two hours past the lunch hour and you're getting close to dinner? I mean, it's simple things like this that days go by and it gets away from you. And there you are by yourself having to make business decisions. wired the same way you are with personal decisions, and then it becomes all-encompassing. You have a hard time separating yourself from personal and business, and that's where the scary gets.

17:42You know, it really resonated with me, too, when you said making personal time within the business relationships, because I think, frankly, that's something that every relationship needs to be cultivated, and if it's going to last because towards the end of you know t squares we were in business for about five years before dissolving it you know some of those relationships began to fray and in some cases to sour and i think a lot of that was because we didn't you know make time for like building and continue the personal relationships right everyone's life is going in there's on a different direction.

18:20And so how do you maintain that shared vision together to make sure you're arriving? Otherwise, your visions will start to change and you'll start to kind of split into different directions. You know, I'm kind of curious if you have any stories where you've seen co-founder partnerships start to go wrong. And if you were able to have any ideas on what caused that breakdown so that others can learn from it. And, you know, I'm happy to share some of my stories as well.

18:48Howie Sher:Yeah, I think from my perspective, the professional breakdown comes from the personal breakdown and not respecting each other. And there are things that are going on in other people's lives that not everyone's comfortable sharing. So when that's occurring, on top of the business challenges that arise, it's very difficult to get it back on the rails. So I think it's easier for me to answer rather than specific scenarios of what occurred and why it shouldn't have, is what can be implemented from day one. I think of, as you were talking, how about an internal company co-founder book club that's relevant to a certain aspect of a business that you all acknowledge you want to learn about and that you could speak to that topic every couple weeks after you read a few chapters, you make that promise to each other and you work on creating an atmosphere of appreciation, of wanting more from each other, of not just having it be.

19:53Howie Sher:So you're in Chicago and I'm in St. Louis. I referred to bowling. How about pretending like we're in San Diego? We're going to go surfing to take our market from business. There needs to be something relevant and connects you, whether it's retreats or quarterlies, that the agreement is you're going into it to grow, to respect, to learn from each other, not to tell, not to boast, not to rest on what's been accomplished, but lean into what yet is to come and how can we best do it collectively, the collective in a team. I'm a team sport guy. I was always the littlest physically on the team, but I needed to find a way to be on that team.

20:35Howie Sher:And maybe I thought it was the bear chasing me. So I was fast and no one could catch me. I didn't want to smell the breath or feel the sharp teeth of that bear. And I wanted to be on that team. And I learned from my teammates that some of which reached the major leagues from a baseball perspective, said to me one day, my get after it-ness in practice pushed him to be better. And if I can apply that in business and have the honor of working with founders of businesses or in my past partners in business, not just my father, the general managers that ran our supermarkets or my investors that believed in me and the brand and the togetherness, that my willingness to persevere and keep going, and it ended.

21:23Howie Sher:It had to end. I couldn't do it by myself anymore. And the revenue wasn't there to have other people be compensated for their knowledge and their hard work. It took me a couple of years to get over that, but now I can apply these experiences just like I am with you, that if we have to look at things personally with some introspection and allowing others that are very different than us to be able to find their own and you respect that as to why you got into it in the first place. You can't get too far down the road with brokenness if you don't start with the solid beginning. And it comes with really listening to each other, really respecting to who is this person, skill, what are their tells?

22:07Howie Sher:What are their tendencies? You asked, what are the signs? If someone shows up with an incredible way of communicating, a cadence, they text back quickly, they email responses very concise and full of feedback from your question. If they look you straight in the eyes, the body language, when you're in a room together, If any of that starts to change, that's a big hint that there's something not right. And if you care enough about the business together, if you care enough about each other personally, you lean into that when you start to see it. It takes courage to do that. I love that. I think that's so key in identifying those moments.

22:45And from personal experience, there were some of those changes and partnerships that I've had in the past. And I think were signs that it was time to move on. There are a lot of founders, especially now who I talk to who are building their business solo. And those support systems, whether it's a co-founder or someone else, are really crucial. And so I'm curious, how can founders build a solid support network even without having a co-founder?

23:11Howie Sher:I shouldn't have to build it. It better be there already. Do not do this if you don't have an incredible support system. Partner, spouse, family, friends. you know, you're not going to go out to dinner with two couples on a Saturday night and tell them everything that's going on about your business. They have their own lives. They have their own businesses that they're in. Let's just be together. But yet you need to feel comfortable if there's things that are in your head that you're not going to be discussing on a professional level, that you're surrounded by people. And I should also add investors that appreciate who you are, what your needs are.

23:51Howie Sher:They have theirs, but you need to make sure that that support system is in place before you flip the switch and say, hey, let's do this. I'm going to do this. It's a slippery slope if you don't have that incredible support system around you. In my case, I had my wife. Just that human touch on those nights where I knew what I was waking up to and I couldn't figure it out when I went to sleep that night. Just knowing she was there next to me and how much she believes in me, there's something so special to knowing there is that support system around you. And you're never alone if you knew you had it in the first place.

24:28Howie Sher:And you continue to be transparent and open to those that love you and those that support you. Truth is never going to change. So if you bury it and wait weeks and then show up and start to tell your support system, yeah, I should have told you this weeks ago, you can't see the brokenness that already exist that super glue is not going to put it back together yeah i hear that i mean i talked to a lot of other founders who um i think you'll want to one of the benefits of having co-founders is that when there were problems or issues in the business there was someone in terms like a work business relationship to tell that to throughout the times right because i also know right for a lot of you know partner spouses that you're going through it with do you want them there in like the heart part times.

25:16It can be, it can be wearing to tell them every little thing that happens and every child like, Oh, a distributor did this. And like the big things, like you definitely want to share them, even the medium things, but you know, incorporate the little things, let your partners