Connecting through Play: Kristi Herold

‘Play is really important when it comes to building good bonds and friendships and having a healthy culture.’

Kristi Herold founded the Sport & Social Group and JAM, which offers virtual social events to help teams connect through play.

‘I’m a big believer in asking for help, and I’m always willing to give it too.’

Kristi started cultivating her entrepreneur’s mindset at a young age under the guidance of her father who was also a businessman. She combined her love for active living and her knack for business in her organization and company.

We cover different topics such as

– building a great team

– overcoming adversities

– finding the goal of your entrepreneurship

Connect with Kristi through these channels:

LinkedIn: https://www.linkedin.com/in/kristi-herold-8a7180

Twitter: https://twitter.com/KristiHerold

JAM website: https://www.workplayjam.com/

John: Thanks for tuning in to Local SEO Today. Don’t forget to subscribe and share this episode. My guest today is Kristi  Herold, the founder of Sport and Social Group, and a finalist for 2020 RBC Canadian Women Entrepreneur Momentum Award. Thanks for being on the show today, Kristi.

Kristi: Hi! Thanks for having me, John.

John: I’m excited because you’re local as well. You’re here in Toronto and I know I spoke to your brother so I’m excited to hear about your entrepreneurial journey. If you can share with our listeners about who you are, what you do, and what do people know you of?

Kristi: Sure. Yeah, I am, as you said, the founder and CEO of the Sport and Social Group which is…We’ve grown to be one of the largest adult recreational sports lead providers in the world. We currently get about 150,000 participants playing team sports on an annual basis in nine different cities in Ontario and Canada…Ontario, and the United States rather. And pre-pandemic, we had 40 full time employees, 350 part time employees and we had hit a number where we had had over one and a half million participants play in our league since we had started back in 1996. Having said that, the pandemic here was pretty hard. Our core purpose has always been connection through play and since the pandemic we’ve not been allowed. We’re now in our 12th month where we are not allowed to operate our sports leagues. So we…I think it was May. By May, we had pivoted to starting a new offering, which is connecting corporate teams through a new kind of play. We’re not playing team sports anymore. We will again, when we’re allowed but we are now running remote games and events to help corporate teams stay connected through play. So, our core purpose has stayed the same. It’s all about connecting through play. And we’ve now helped over 50,000 participants since May of 2020 connect through the playing of remote games and events. Things like, Name that Tune Bingo and Survey Says, which is like a family feud style game show or scavenger hunts. We’ve got five different escape rooms, we have a whole bunch of different events and games that we offer. We’ve hired out of work actors and comedians to be our amazing hosts. And we’re doing this…So we’ve gone from running this b2c business geographically focused to now a b2b business that’s global. We’ve run events for companies in Thailand and India and all over North America,  all over Europe. It’s amazing because we can connect companies that have global offices. They  might have someone sitting in New York and LA and Toronto and London, we can connect them all for a very affordable rate through one fun game, you know, a lunch and laugh, or a happy hour, and they can all have some laughs together and stay connected. Because play is really important when it comes to building good bonds and friendships and having a healthy culture. So, it’s been really a fun…It’s been an interesting year. A lot of challenges but we’ve created something really positive from it with this new business of Jam and the website for jam is workplayjam.com . So yeah, that’s who I am.

John: That’s amazing, Kristi  because knowing what I know about Sports and Social Group, I was a member for, I believe, five years playing volleyball and basketball here locally when I was in my 20s. It was a great way for me to not just get exercise but connect with people that were also in the same kind of age group but wanted to play and exercise and have a social network, right? So, I met some really good people along the way, and I still connect with them today. So, I know you’ve been doing a great job at what you’ve been doing. So, I’m very proud of what you’ve built.

Kristi: Thank you. That’s so…It makes me so happy to hear when people have played with us and have created relationships and friendships. And that’s the power of play. When you play with people you do form really strong bonds, whether it’s playing Ultimate Frisbee or beach volleyball together or whether it’s playing a game of bingo or having a scavenger hunt with your fellow colleagues over zoom call. Play is really powerful. It’s an incredible…I’m a big believer, you know the saying, “An apple a day keeps the doctor away.” Well, I believe play each day keeps the doctor away. I think it’s a really important, healthy thing that we need to make time for in our lives.

John: Amazing. So, I know now you’re busy with this business but maybe if we can take a step back in your journey. I know…I spoke to your brother as well, Cameron, great story and very similar upbringing, I’m sure for you.

Kristi: We were raised in a pretty entrepreneurial household.

John: But what happened afterwards? Like, did you go to school? And if you don’t mind sharing with the audience member a little bit about your journey?

Kristi: Yeah. And so we grew up in Sudbury. Our dad was an entrepreneur and so we all sort of dabbled in running our own little businesses growing up. We had to work for what we wanted in our lives, we had to pave our way through university. So, we knew we had to save money for that. So, I ended up going off to Queen’s University. I had to study Commerce because I thought that’s what you did when you wanted to run your own business. I knew I wanted to run my own business. So, I thought, “Oh, I better go do a business degree.” The very first day of Intro to Biz class in my first year of Commerce, the professor asked who in the class intended to run their own businesses one day and I put up my hand thinking everyone was going to. And there was myself and one other person in a class of 200 people that put up their hand and I was like, “Oh, my gosh, I think I’m in the wrong place.” Anyway, I ended up doing a commerce degree at Queen’s and after first year university, the Dean of Commerce called me into his office and he said, you know, your marks have gone down a lot since you began here. It looks like you’re on the ski team and on the rowing team. I think because you’re on two teams, it’s showing that you can’t…You’re not able to handle both, your marks aren’t very good. And I said, “You’re right, Sir. I will next year. I will just do the ski team and I’ll drop the rowing team.” And he said, “Okay, I think that’s a smart move.” Said goodbye, walked out of his office and I was laughing to myself. What he didn’t realize was I was running two businesses while I was in university. So, my ski team and rowing team had nothing to do with my poor marks. It was the fact that I was running two real life businesses. I was running a College Pro Painters franchise, and I was running a custom clothing business selling sweatshirts and baseball hats to kids on campus. Suffice to say, I kept running my businesses and I did very well with them. They paid my way through university and got me a down payment on my first house and my marks never improved. I was not a very good student. I was more a student of real life business experience than I was Commerce. So, after university, I left Kingston and moved back to move to Toronto, and so I’m now a small town girl living in the big city. And I was looking to meet people and I thought maybe I could join a soccer league even though I wasn’t a very good soccer player, I just liked to play sports. And anything I looked into was really competitive. And I’d heard about this Sport and Social Club in San Francisco and so I thought, “Hey, maybe that’s something I could try in Toronto.” And so I left my job at that time. I had done three years as a franchisee with College Pro and I’d been working for one full year as a general manager for them. And it wasn’t…Working as a general manager, didn’t have the entrepreneurial spirit that I wanted in my life. So, I made the decision to leave College Pro and start Sports and Social in 1996. And in that very first year, we had 250 teams play a variety of five different sports over that first year and then fast forward, I guess for the next 10 years, I sort of was focused on very local growth. I wasn’t looking to expand at all. I wanted a lifestyle business because I also had three children in that next 10 years between 2002-2004. So, built up a nice, great team of people who were making the operations run smoothly, and we just had nice steady growth by delivering good word of mouth or good customer service was helping us build our business through word of mouth. We weren’t really focused on building a brand and we stayed very local. And then the next 10 years, from sort of 2006 to 2016, I stepped back and had…My team was doing a great job and I was very part time. I pursued some passion projects, started a community musical theater group connecting people through playing on stage and we raised over a half million dollars for charity with those musical theater groups over the years, which is something I’m really proud of and have a lot of fun doing. But by 2016, I was bored and needed to change because it was now 20 years into this business. It was doing well but I needed something different. And I was trying to figure out what am I most excited about? What gets me feeling excited? What’s the legacy that I want to leave? And at the time we had about 70,000 annual participants playing in the Sport and Social Club league and I thought, “Imagine if we could get a million people playing every year.” That would be something to be super excited about. So, that became the new vision in 2016, was to really grow and expand. So, since 2016, we’ve done eight acquisitions of smaller leagues. We’re now, as I said, in nine different cities across Ontario and Michigan and we were before the pandemic, we were getting about 150,000 people playing and we’re going to go back to…We’re gonna go back to getting people playing again, as soon as we’re allowed. In certain cities we are actually allowed but like, in Michigan we’re not. We’re not operating in most of our Ontario cities. And so we’ll get people playing sports again. But now we’ve built Jam, workplayjam.com. And it’s just exciting to me to think in our first year, it looks like we’re gonna hit seven figures in revenue. Our NPS score is 80, which is amazing, like, people are absolutely loving what we’re doing. Over 65% of our clients have booked multiple events with us and so if we’ve gotten 50,000 people connected through play in our first year, I believe as we are able to open up sports again, we’re going to get…In the next three years, I’d like to get a half a million people playing annually, and by the next six years, get a million people playing annually. That’s the long term vision but ,you know, playing both sports and in jam remote events, helping organizations like yours, where you’re working remotely, stay connected playfully. 

John: I love that. I mean, that’s the biggest purpose, right? Like, for you it’s about connecting people and, you know, for you to know what you want and see more of a legacy where you’re making a difference in people’s lives, right? By connecting people. So powerful. I love it.

Kristi: Some of the stories we have, John, from our Sport and Social I mean, it sounds  like you’ve made some friends that are gonna be lifetime friends, which is awesome. And that’s so common to hear. We also have, you know, thousands of people who have met their spouse, their life partner and had babies because they met playing dodgeball, or they met playing basketball or soccer. And we’ve had people…We’ve had three of our members get our logo tattooed on their body because of their life changing experiences from playing in our leagues. And one story always makes me tear up every time I think of it. We got an email about five years ago from a member who advised us that, she said, “Your leagues have literally saved my life.” And she explained that she moved to the city of Toronto, didn’t know a lot of people, was feeling really lonely, sad, depressed, anxious. A colleague invited her out to join the soccer team. She wasn’t a great soccer player but she kind of was like, you know, in the depths of depression and figured, “I’ve got nothing to lose.” Went out and made a ton of new friends playing recreational soccer. And she said, “You know, this saved my life.” Which is just incredibly touching. I’ve had people tell me, they’ve lost…One guy has lost I think about a hundred pounds because he just got all in on playing sports with us and it really helped him change his lifestyle. So, there’s just so much positive that happens from connecting through team sports and now, it’s amazing to hear the impact we’re making on corporate culture. People are just saying how much fun they’re having when they take a break for an hour, jump on a zoom call. It’s not a long drawn out meeting and they don’t have to do anything except show up. And then our hosts entertain them and connect them through playing of games and we get them laughing and kind of…It’s good team building. And so we’re just…It’s an all around positive impact, which makes it really easy to get up every day and get excited about the work we’re doing.

John: I love that because you’re making a difference, definitely. And you’re building a huge community of people that are like minded. So, with similar interest, right? Let it be sports, let it be online games, whether it be play, right? You never know what’s gonna happen. And like you mentioned, there’s weddings that happen, children, there’s, you know, depression. I love that because making a difference is what resonates with me like, I’m a big believer of giving. Adam Grants, you know, Give and Take. Being there whenever people need assistance, like, don’t push people but when they’re ready, they’re gonna reach out.

Kristi: Be there to serve, right? Yeah. 

John: Be there to serve and constantly just be aware that you’re here to serve a purpose, right? In life. You have a bigger purpose and vision. So, I love that. In terms of like, growing up, I know your parents were entrepreneurs. Did they give you a lot of like, advice or was it more like people that surrounded you like, how did you get into entrepreneurship?

Kristi: Sure. Yeah. So, my mom was not an entrepreneur. She was a homemaker. She was a trained nurse but most of my growing up she was a homemaker and amazing at it. Like, I kind of grew up wanting to be a mix of both my parents because they were both such awesome role models for us. My dad was definitely the entrepreneur. I remember very clearly he never…I don’t think he preached as much as he led by example and I am very curious by nature. So, I asked a lot of questions. I remember one dinner table conversation asking my dad, “How much money do you make? And how much money does your business make?” And my mother was horrified. And she said, “Kristi, we don’t talk about things like that.” And my dad said, “Well, wait a second, Judy. Yeah, we do. We have to talk about this. How else do we expect her to learn because they’re not going to teach her this in school.” And I guess he felt like, I was probably at an age that I could be responsible enough that I wasn’t gonna be blabbing it around, you know? I think I was probably 13 or 14 at the time and so he walked it through with me. And another time I remember, I was 15 and I started a lawn cutting business. And I didn’t have a driver’s license, because I was only 15. So, I made pamphlets with…I drew up pamphlets, and my dad would…They would help support us however, they could. So, he took my little drawing and he took it to his office and he photocopied me like, a hundred copies of my little pamphlet. And then I went door to door in my neighborhood, anywhere that I could walk to, and I delivered the flyers. And I ended up getting about 20 customers. And I’d spent my summer walking, pushing my lawn mower because I didn’t have a car, you know, push it around and I would cut people’s grass. And I kept clear track of how many hours I spent, and how much money I made. And at the end of the summer, I kept this little, you know, handwritten. It was a spreadsheet, effectively handwritten. And I showed my Dad, “Look, I did this many hours of work, and this is how much money I made.” And he said, he stood back and watched me and he said, “That’s fantastic. I’m really proud of you. And you know, how does it feel?” Then he said, “Have you ever thought about how much more you would have made if you had someone working for you?” And I was like, “I don’t understand how would that have made more money? If they’re working for me, then I have to pay them?” And he said, “No, well, what happens, Kristi…” And he explained that, if I’m charging $15 an hour to a client to cut their grass, and I’m paying a student, you know, back then I think I was probably paying $5 an hour to a grade nine boy to cut grass with me. He said, “You know, if you’re charging 15, and you’re paying an employee five, you’re making $10.” And I was like, “Oh my gosh, I’m making a full 15 on myself and I can make 10 off.” I actually think it was 15 and seven. So, I think I was making about seven off of, you know…And so it was like, the light bulb went off for me. So, the next summer I hired two boys to work with me and I actually got my driver’s license and we got…So, we were able to go and get further clients. So, that’s the kind of way my dad would teach. In another time. I remember when I was running College Pro, my very first summer. I had half of my painters…I had, I think I had eight painters. Four of them quit. They worked on May and June and I needed them till August. Four of them quit on me by the end of June. And I was like, “Oh my God, now I have to start hiring again. I have to train them again.” And I talked to my dad about it. I was really frustrated and he said, “Have you considered that it might be how you’re…How you’re approaching working with these employees?” And I was like, “What do you mean?” He said, “Well, you know, have you shared with them what your goals are? Are you looking to get them on your side? Are you incenting them with bonuses? Or are you being a bit of a dictator?” And I was like, “Oh, yeah. I think I’m being kind of bossy like, I’m telling them what to do. And I’m not really incenting them to help me get to my goals.” And so he was kind of…He opened my eyes to maybe having a shared goal with my team and the second half of the summer was so much better. And I was…I started bringing treats to them on the job site. I dropped off popsicles and pops and little things that didn’t cost a lot but showed them I cared about them. And those same group of painters that I had for the second half that summer stayed with me for the next two summers after that, and what a difference it makes when you’ve got a shared vision as a team. You know, so my dad was really inspirational to me, he taught me a lot just by asking questions and kind of pointing…Just building awareness around different ways of doing things and definitely instilled an entrepreneurial spirit in all of us. My other…Both my brothers are entrepreneurs as well.

John: That’s amazing. I love that because having someone that close to you, being able to give you advice, honesty, transparency, and giving you support along the way as opposed to…Yes, you’re gonna fail, you’re gonna make mistakes but how do you learn, right? That’s the only way to learn, by making mistakes. So, that’s entrepreneurship and without that, I mean, I don’t think you would be the person you are today, right? Like…

Kristi: Oh, for sure. Yeah, I would be the worst employee like, I’m definitely not cut out to be anything but an entrepreneur I think.

John: That’s amazing. So, over the years, as you’ve grown your company, were there people along the way? Were there groups of people that supported you? Did you go through mentors along the way, masterminds, courses, coaches, like, because as you evolve, as you grow in the business, when you look at a bigger vision, the legacy of yours…Were there people that supported you along the way, or…

Kristi: Oh yeah, absolutely. I think, early days, I relied on my dad a lot. It did… I remember kind of pretty clearly, getting to a point in my mid 30s when I thought, “I think I’ve kind of outgrown my dad’s advice, now.” Which was interesting. And I’m still very close. We’re still very close but I don’t really talk to him about business as much anymore. And I sort of moved into a phase where my brother Cameron has always been he…I mean, he’s a coach of, you know, he’s a business coach and has been for many, many years and he’s a wealth of knowledge, written lots of books and I mean, he’s pretty incredible. So, he’s been a fantastic resource, mentor, support, ask kicker. He kicks me in the butt all the time and he’s, you know…I know I’m gonna get candid feedback from him. He doesn’t pull any punches, that’s for sure. Early days, I also remember getting shut down. I went and talked to a very successful businessman and he was the friend of a father…The father of a close friend. And I was excited to share my idea for Sport and Social. And I shared it with him. I’d walked into his downtown Toronto, fancy building, and I was just getting ready to start the Sport and Social Club. And I shared my idea. And he’s sort of scoffed and said, “No, this won’t work. And here’s why.” And he had these reasons. And I was like, “Wow.” Really heartbroken by it and I remember walking in his office and taking the subway home. And I thought, “You know, I don’t agree. I’m not. I still think this can work. I really believe in what I’m gonna do here.” And so that kind of spurred me to almost prove them wrong and I’ve never had a conversation with him since. But I will never forget that conversation. But also early days, I had other sort of more experienced businessmen who really supported and loved what I was doing. I remember Pete McCaskill was such a support early, early days, like, the first year of running Sport and Social Club, he was the lead on the Gatorade. They ran the Gatorade account, like, all the experiential marketing and he loved what we were doing and he’s been a support ever since. And same with Jim Sanderson from Wilson Sports. They came on board as a partner before I even had people signed up to play sports. So, there have been amazing people, early days and then my team is amazing, like, every step of the way we’ve had…Culture is really important to us and I think we’ve worked really hard to have a group of people that really compliment each other. Our core values are strong, and we’re all about teamwork and delivering what we promise and getting shit done. I mean, those are…It’s a team who’s driven to provide great service and so I really am fortunate to have such a good team of people. And then in terms of other networks and such, I did join EO, the Entrepreneur Organization. I think it was in 2013, I went to the…I did the entrepreneur master’s program at MIT and then after that, it was a lot of  EO people, mostly EO people. And so I joined EO after that,  had an amazing group of forum mates there and I was in that forum group for about three years, and then left the forum. But I’m now in a different forum not through EO anymore but a group of business entrepreneurs that I meet with once a month. I also meet with a group of women entrepreneurs, once every six weeks. And then I’m in the Mastermind Talks group, which my friend Jason Gaynard started, that has just an amazing network of awesome people and we tend to meet in person once a year but we have a…When we can. We didn’t get to this past year. We have a Facebook group that we share, you know, you ask and you share and you give and it’s all about trying to help each other out as a group of entrepreneurs. And it is a powerfully…It’s just so positive and powerful. This group of amazing people that you can kind of ask for help from and give to. And so definitely a lot of resources. I think network is so important because it’s good to be able to give back as well as ask for help and I am not shy to ask for help. That’s for sure.

John: And that’s a big thing, like, acknowledging where the gaps are, acknowledging where you’re at in terms of your journey, right? As an entrepreneur, early stages, very lonely and you feel like you’re spending spinning your wheels now, what’s gonna happen? As you mature, as you’ve been in it for many more years, cultivated team, values, lifestyle, like, all these things, then you have more clarity. You have a better vision, right?

Kristi: Yeah, absolutely. And you know, you’re right. Like, an entrepreneur…You can’t know it all. You’ve got strengths, right? We all have strengths, and we all have weaknesses. And there’s…And so I’m never too shy to sort of…I actually love being the dumbest person in the room because I love surrounding myself with people way smarter than me so I can sort of learn from and ask. You know, before I’d done these acquisitions, I knew nothing about mergers and acquisitions. In fact, the words mergers and acquisitions, when I was in finance class in universities make me feel nauseous and so when I decided to grow the company by doing acquisitions, I was like, “I don’t even really know what this is all about.” I spent a year going out for breakfast, lunches, after work drinks with people who would…Whoever would meet with me to explain the strategy of doing a roll up, to explain the strategy of, you know, buying smaller groups and, you know, get the economies of scale being, you know, getting smaller groups all under one. And it was really helpful, because I knew nothing about it. And I still ask people all the time for help on this, that and the other thing like, I’m a big believer and ask for help. I’m always willing to give too, whenever I can.

John: But I love the fact that you’re not just vulnerable but you are ultra curious. And you are an action taker. There’s so many people that are passive, they’re waiting for things to happen. They’re waiting for the next big idea to happen.

Kristi: Yeah, it’s a pro and a con. I mean, I think some people in my life are a little too, like, could you relax already because I think I want everything when I decide I want something done. I want it done yesterday. And I’m a bit of a dog with a bone. You know, my husband would sort of suggest that, like, when I get something in my head, I don’t let go very easily. Definitely get shit done is one of our core values. And I’m definitely an action taker for sure. It’s a positive but it can be a negative. I’ve done it, you know…

John: But you have to surround yourself with like, people that are real with you, right? They’re gonna speak the truth. They know you. That’s what you know, building a team, like, you’ve built and people that you respect and they respect you. And this is, like, relationships that matter is what really is all about, in terms of life, right?

Kristi: My COO is Rob Davies, he started playing in our sports leagues in 97, or 98. He actually met his wife playing for our league. He applied for a job with us in 1999 and he’s now a business partner so I’ve been working with him for about 21 years. I think of him like a little brother but Rob is, we always joke…I’m the gas pedal and he’s the brake. It’s very much the sort of visionary-integrator relationship we have, like, we sort of joke that I’m lightning, and he’s thunder. I go around and strike hard and he’s kind of the thunder, warning people that I’m coming. But we have a really good…He’s the one who…He can be really candid with me and you know, he always jokes, “You’ve got 10 ideas a day and occasionally one of them is good. Most of them aren’t so good.” And he’s never afraid to tell when they’re not good. Which is great.

John: But that’s what you need, right? People that ground you to a level, like, think about what you just said, slow down. I’m the same way as you, right? Like, three am I would wake up with a bullet note, task list of notes with ideas, and I would blast it off to certain people on my team. They’re like, “What are you doing waking up at three? First off…And why are you coming up of all these…”But that’s because we’re entrepreneurs by spirit, right? 

Kristi: You can’t control it, like, it’s who you are, right? Do you keep a pen and paper beside your bed with…Or do you take notes in your phone?

John: I would wake up and I would be taking notes. And then I would open a calendar, I would start writing notes and messaging people and they think I’m crazy. 

Kristi: My dad, I remember as a kid, my mother got so frustrated by my dad waking up in the night and having ideas and turning the light on. She bought him a pen that has a light in the pen so he could write his ideas on a pad of paper and not wake her up. And so actually I’ve been getting up and when I get my ideas in the middle of the night. And I would type things on my phone but it’s not good to look at that screen, right? And so I actually just about a month ago…And I also didn’t want to turn on the light and bother Dave sleep. So, I bought myself a pen just like my mom had bought my dad with a light in the bottom. So, I keep a pen with light so just for that purpose…So you can wake up in the night, get it out of your head and then you go back to sleep. And in the morning, you can look at it with a little more clarity perhaps but also know you haven’t woken up the whole house by turning the lights on.

John: Tell me a little bit about like, the upbringing of your children because I know you mentioned you have three children and they basically…During that stage of growth, building Toronto Sports and Social Club, like what…How did you do it all? Like…

Kristi: Okay. Well, first of all, so in 1990, when I started Sports and Social Club in 1996, I was dating this guy Raul who a year later became my husband and then also became my business partner. So, Raul and I built the Sport and Social Club together from the get-go. We got divorced, I think in about 2012. But we’re still business partners and friends. In between 2000 and 2004, we had three children. And so he and I were a great team. We used to really, you know, whoever…If someone had an important meeting, the other person would be the first one home to take care of the kids and get dinners ready and that kind of thing. We really played off of each other well that way. And in terms of…And now, my new partner, Dave and I, we have three. We each have our own three kids. We’re Brady Bunch, because his last name is literally Brady. We’re literally The Brady Bunch. Three girls, three boys and so I call them my three bonus kids. But I’m always…I think I drive the kids a bit crazy because I’m constantly like, you know, they’re teenagers they all have…They need summer jobs and so I’m constantly like, “Hey, you should do this as a business. Have you thought about trying this.” And I will say my three kids have actually…They’ve each run their own businesses of some sort, Cassidy’s 20 now, but as a 12 year old, she started a dance camp at the ski club that we were at. So, after ski lessons were done, she would take a group of kids and teach them dances. And so the parents could go have a drink in the bar. And she’d have 30 little kids that she’d teach dancing in the brown bag lunch room. She did that for about five years and made great money for herself, or for the march breaks and Christmas camps. And love doing it. And the kids loved having to do it. Andy, who’s 18 and a first year Business School at McGill right now. Last summer, she ran a little…A grocery delivery service because it was hard to get a job last year with COVID happening. So,  she ran a grocery delivery service for all the cottagers in our area and I think she learned a lot from doing that, build yourself a website and, you know, marketed it and got clients. So, she would run into town so people could stay at the beach and get their groceries for them. And then my son Dax, who’s 16 going into…He’s in grade 11 right now. He also ran a little business last summer. The summer camp at our cottage was cancelled, so kids couldn’t go to summer camp. So, he organized a group of…He would take up to six kids at a time and he ran a little sports and adventure camp every day for about three hours every afternoon. And he’d take the kids on hikes and he’d play, build sandcastles with them, he’d take them on scavenger hunts, play sports with them. So, it was amazing. Parents were so excited to again get the kids out of the house away, like, out playing. It was a great opportunity for Dax. And so they’ve all had a little taste of what it’s like to run their own businesses. It’ll be really interesting to see if any of them choose to run their own businesses later in life. But I’m excited that they’ve all had a little taste of it. And there’s no End of discussion around it because I just can’t help myself. I talk about it all the time and they’ve also…Every single one of them actually has worked at Sport and Social Club. They’ve all…Cassidy was trained as a customer service rep, she worked for us for I don’t know from the age of…My kids when they were…The rule was once you turn 12, if you have a PA day, you don’t get to stay home and watch TV. You come to work. It’s a family business and you come work. And so they’ve all done a lot of work at the Sport and Social Club. And Cassidy did customer service, Andy has worked operations and learned how to do scheduling and stuff. And Dax, actually, he was a league Ambassador with our Sport and Social Leagues. He used to run for hockey games but then when the pandemic hit, he’s now a Jam host. So, he hosts some of our remote events and he’s amazing. He’s really engaging online and people love him. So, it’s really been fun to see the kids. They’ve all had a taste of working in the family business. They’ve all had a taste of running their own little businesses. So, we’ll see how it…We’ll see where they end up.

John: That’s amazing. And I think understanding like, being the parent and the lifestyle that you kind of built in this business allows for it, right? Allows you the opportunity to harvest people like, that you love and want to support, to gain, get exposure. Learn from it. Not a lot of businesses allow for that, especially if you’re a professional service, right? Like, there’s a skill set that needs to be involved around like, the actual technical skill versus the business that you’ve built. And a lot of people can only imagine and dream of something like, what you’ve built. It’s amazing.

Kristi: Thank you. Yeah, pretty…I’m pretty grateful for the ability to get up every day and push play. I’m pretty grateful for that, for sure.

John: A couple questions regarding like, mistakes and challenges, were there many setbacks over the years? What were some of the major ones? And how did you overcome them?

Kristi: Oh, goodness. You know, the life of an entrepreneur, there’s ups and downs every step of the way, right? Over 25 years of building Sport and Social Club, I mean, the most major setback is this pandemic, without a doubt. It’s just been…It’s rocked us to our core. I mean, I was thinking we were pretty diversified by being in nine different cities. I didn’t think…I’d never in a million years would have imagined I needed to diversify against a global pandemic. I just never could have envisioned that. I never think people would have to stop playing softball, you know, I just….It’s still kind of hard to fathom, isn’t it? So, for sure this past year has been extremely challenging. I can’t think of any clear cut examples, though. There were many, many days and weeks of stress here and there with Sport and Social and I think, you know, I’m certain we made mistakes along the way. Lots, lots and lots of them. I think the key has been always, let’s not beat ourselves up over our mistakes. And I’ve never, you know, I’ve had employees make very costly mistakes before. I would never fire an employee because of a costly mistake. I would, however, wanna ensure that they would never repeat that mistake, right? Let’s learn from our mistakes. I think as you mentioned earlier, it’s so important to recognize. Making mistakes, that’s okay. It’s normal, and it’s healthy. As long as we learn from them. Now, this past year, we didn’t make a mistake, the pandemic was really out of our control, right? We didn’t make a bad business decision. So, it’s been challenging because it’s hard to be told by our government, “You’re not allowed to operate your business. But we’re also not going to give you enough money to cover your costs and good luck.” It’s been a really challenging for a lot of small businesses out there. You think of all the gyms and health clubs and restaurants and family businesses, retail shops that are being mandated to close. And it’s challenging and frustrating, for sure. And yet, here we are. And so I’m incredibly proud of my team, that we were able to find a way to pivot and create this whole new business of workplayjam.com. To be able to get this people jamming and connecting through play in a whole new way and to now know, we’ve got a whole new business…Revenue stream. We really are a lot more diversified now. Going into the future, we have a b2b business that’s globally focused, that’s virtual and we have a b2c business that’s geographically focused, that’s in person. Both with the core purpose of connection through play. So, I think we have learned a lot from our experiences and we’ll keep learning as we go. Every single day is a new life lessons being learned.

John: Yeah, I love the fact that you know, just allowing to help others evolve, right? Making mistakes is a part of life. How do you learn from it? How do you pick yourself up? How do you grow? And hopefully it does…It’s not detrimental to your business, right? And these setbacks like,  this pandemic, no one could have forecasted the…Like, travel, tourism industries…I deal with a lot of small business owners, and a lot of them been impacted but fortunately, digital is still, you know, a part of their business and a lot of them can elevate in that sense as well. 

Kristi: Yeah. I feel really, you know, the travel industry. If you’re in a travel industry, it’s crushing. It’s been crushing for them. And same with live events, like, that’s gonna be…

John: Yeah, corporate live events, weddings…

Kristi: It’s gonna be longer coming back, right? And so I do believe when people are allowed, I mean, I’m really hoping that by this spring, we’re able to get people outdoors playing because…Hey, if you’re…The rules in the redzone right now…You can have 25 people in your backyard for a keg party but you’re not allowed to have those same people cross the street and play softball? Bit of a problem with that. So, I’m hoping that we’re gonna  get that changed so we can get people…Because people need physical activity. They need it for their mental and physical health. So, I’m hoping that by spring, we’ll get people playing outdoors safely in a physically distanced way and where we’re not able to be physically distanced wearing masks, you know, I think we’ll be able to…We’ll be able to hopefully get that happening sooner than later because it’s an important service we’re providing people. 

John: Yeah, definitely. Just the last couple questions Kristi, it’s been such a pleasure to get to know you more. What drives you today like, what are your clear goals because it seems like you pivoted last year. You’re now  doing this b2b space and b2c has always been the key driver and your play message, right? What does legacy look like for you? 

Kristi: I’m so driven by the idea of getting a million people playing and I used to think it was gonna be a million people playing team sports. It’s not. It’s  gonna be a million people playing and connecting through play. Whether it’s team sports or playing, you know, survey says, or name that tune bingo, or whatever other game we’re offering them online. It doesn’t have to be soccer. It can be any of the above. It’s just connecting through play. I’m so driven to get them to know that we’re positively impacting the lives of a million people every year, that is what I want to be able to say. I want people to remember me as that’s the girl that pushed play. That’s the girl that got us connecting through play because of what she and her team were doing. You know, we had laughs, I connected with laughs, I connected with fun. I smiled, I had a better day because of those experiences that Sport and Social Group and Jam are providing. That’s the legacy I’d like to be known for.

John: That’s amazing and you know me with a younger son. I spent like, as a parent you understand like everything you’re doing is about them, right? It’s about like, having a better future for them, training them with all the core values and habits and all that stuff.  I play all day long when he’s home and that’s the most important thing about life, right? Like, that smile, the time that you have to enjoy one another, right? 

Kristi: That’s what makes memories, right? You don’t remember…You’re not gonna sit back and think, “Oh, wasn’t that an amazing business meeting we had?” But you will remember, “Remember that time when we did that lunch and laugh and we had the scavenger hunt. And Sam came running back wearing that crazy superhero costume?” Like, that’s the things that people remember, is when they play and connect with laughs. 

John: And there’s two things I value the most in life, it’s relationships and experiences. And those two things alone will make and break everyone’s lives , right? 

Kristi: Totally agree. 

John: If you don’t live with good people that surround yourself in community or sports or whatever it is like, job, family, friends. Find people that resonate with you, find things that are connecting in different aspects. You seem so upbeat. It’s amazing and I’m glad that at least we’re connected. I love it.

Kristi: I agree. Thanks, John. I really appreciate having you having me on to chat and share some of the stuff. The one thing I will just want to add on to what you just said, the idea of relationships and experiences, I couldn’t agree more. And something that happened with the early when we…The early advent of Jam last summer. We had a client who had so much fun. We ran their company picnic for them, it was online. We did family scavenger hunts and we got all you know adults and kids all experiencing it together and they had so much fun. They called us the next day. They said, “We are b2b business, we often send baskets to our corporate clients as gifts we’re wondering…Can we send them a gift certificate for a jam event because we’d like to give them the gift of this experience that we just had.” And we were like, “Oh, my gosh. Yes, that’s brilliant.” And so that’s become the thing that…Where a lot of people are starting to think of us as an offer, as a gift when you have a corporate client. What a great gift to give the gift of experience, right? It’s not a super expensive offering that we have so people can give the gift of play to their clients which is super. It was a really awakening moment when I heard this client wanting to do that. It’s been amazing to think that…

John: It’s another revenue stream, right? 

Kristi: Yeah, it’s just more events and getting it…Helping more people connect and play.

John: It’s amplifying your message, for sure. With positive experiences, right? Like, this is what…I deal with so many business owners and for me it’s more about like, just understanding the value of like, what you’re offering but the people you’re impacting more so and the value you’re bringing to these people. If you can really give them a really good experience along the way they’re gonna be with you for a very, very long time. So, customer service is great, understanding the value that you bring and continue doing…Improving, right? Continue getting better and…

Kristi: Yeah, listen to your customer,  right? 

John: Exactly. All these things are so important. So, last question,  aside from business…I know we’ve been talking about business and we talked about family a lot. Is there anything that we’re missing in terms of what molds you as a human?

Kristi: Honestly, like, I didn’t really clue into this until about five years ago. When I look back at what makes me who I am and what’s my, you know, people say what’s your superpower? What’s your secret sauce? I’m all about…I’ve realized like, in high school I started the social committee that didn’t exist and I led that and ran scavenger hunts and  car rallies and stuff for people in high school. I’ve always been the social convener of my friends. I’m always the one saying, “Let’s get together and do this.” And I’ve realized I’m all about Sport and Social Club, Jam  and even my community musical theater. I’m all about connecting through play, that’s what I live and breathe. I just naturally…I’m drawn to doing that  and I mean aside from that I’m a really active person. I love making time for adventure. I love to travel so I’m really missing the travel right now. I’m excited to get traveling again. And, you know,  I just love to be active, you know, whether it’s doing peloton workouts, or yoga, or playing…Throwing frisbee with my kids and playing guitar that’s my little meditative practice. I’m not very good but I love to play guitar and belt out tunes like, sing by myself and entertain myself. That way is a  little bit of how I spend my time. 

John: That’s amazing. I love how you’re living life, right? With purpose and that’s what life is about, right? Like, take control of it, do something that you love, be passionate doing it and surround yourself with people that support your cause, right? 

Kristi: Totally. Yeah, I think what it was that there’s a quote and I forget how it goes but, you know, “I’ll sleep when I’m dead.” Basically. There’s too much living to do right now and as George Bernard Shaw, my favorite quote ever is George Bernard Shaw saying, “We don’t stop playing because we grow old. We grow old because we stop playing.” So, I just never want to stop playing sounds like, you’re similar. So, I love the hearing that you’re playing with your son that…I love seeing that you have a basketball photo behind you. That’s awesome. Sounds like, you embrace play in your life which is so fantastic.

John: Yes, I definitely do. Well, thanks a lot, Kristi. So, how do some of the listeners get a hold of you, reach out to you if they have any questions or check you out online? 

Kristi: I’m on linkedin Kristi  Herold, k-r-i-s-t-i Herold, h-e-r-o-l-d. I’m on linkedin and instagram kristiherold_ and then workplayjam.com is the best way to learn more about the really fun events we have that can connect corporate teams through play. There’s so many different offerings with our amazing hosts that will keep people laughing. Laughter is guaranteed that’s…We have a money back guarantee. If you don’t laugh you’re getting your money back. 

John: So, that’s awesome. Well, thanks a lot Kristi. It’s been my pleasure to interview you, had a lot of fun.

Kristi: Thanks so much for having me. 

John: Thank you.

Kristi: Take care.