Chin Weerappuli, The Underdog Family

[00:00:00] Sanjay Parekh: Welcome to the Side Hustle to Small Business Podcast, powered by Hiscox. I’m your host, Sanjay Parekh. Throughout my career, I’ve had side hustles, some of which have turned into real businesses, but first and foremost, I’m a serial technology entrepreneur.

In the creator space, we hear plenty of advice on how to hustle harder and why you can “sleep when you’re dead.” On this show, we ask new questions in hopes of getting new answers. Questions like: How can small businesses work smarter? How do you achieve balance between work and family? How can we redefine success in our businesses so that we don’t burn out after year three?

Every week, I sit down with business founders at various stages of their side hustle to small business journey. These entrepreneurs are pushing the envelope while keeping their values. Keep listening for conversation, context, and camaraderie.

Skill-based volunteering is the anchoring philosophy of The Underdog Family, a nonprofit based in Denver, Colorado.  The Underdog Family, or TUF, provides website design services to small businesses 100% free of charge. They utilize a team of highly skilled professionals as pro bono volunteers.  Today on the show, I’m speaking to the organization’s founder, Chin Weerappuli. Chin, welcome to the show!

[00:01:20] Chin Weerappuli: Thanks for having me.

[00:01:22] Sanjay Parekh: So I'm excited to talk to you because I think what you're doing is really kind of fascinating. But before we get into The Underdog Family, tell me a little bit about your background and your history and kind of how you got to where you are now.

[00:01:34] Chin Weerappuli: Yeah, absolutely. So my name's Chin Weerappuli, Born in Baltimore, but pretty much spent my whole life in in Michigan. And for me to kind of tell you the story, the origin story of The Underdog Family kind of have to know a little bit more about me as a person. Where when I was in high school there's a natural disaster that affected the island of Sri Lanka, which is where my parents immigrated from back in the late seventies.

And at the time, you know, my dad really encouraged me to kind of get involved in the Sri Lankan community, help fundraise, help raise money, and in my high school kind of circle of friends, it wasn't a lot of money, but what we raised, I was able to see the real impact of that. Especially the impact for those who need it.

You know, supplies, blankets, things like that, that we were able to send. And it planted a seed in me from a really young age where I always wanted to find opportunities to give back where I could. Fast forward, you know, after attending the University of Michigan, I got a job in healthcare software consulting where I was on the road, you know, Monday through Thursday, pretty much every single week.

This was back in 2012. And while exhausting and exciting, it also kind of created this idea that it was tough to be involved in the community since I was always kind of in between multiple cities. But, 2020 comes around March, and all my travel gets shut down because of the COVID-19 pandemic. It was the first time in my life, really, post college that I was in one city.

I was in Denver, Colorado where I moved in 2018. And I kind of looked at myself being like, here's an opportunity, you know I thought for the eight nine years that I wanted to get back to giving back to my community, but I always had this excuse of I'm not really around. Well, it's put up or shut up time, Chin, you know, if you truly mean what you want, what you what you think, you can act on it right now.

So, when my travel was shut down shortly after, you know, there's a lot of social unrest the murder of George Floyd occurs, and there's this event in Denver and across the country called Blackout Tuesday that was designed to support black-owned restaurants small businesses in your community.

And I remember going to one of my favorite restaurants, just down the street from where I live in the Five Points neighborhood of Denver and seeing, you know, a line around the block, a lot of people trying it for the first time I was speaking to, to quite a few of them and they mentioned, you know, oh yeah, this place is great.

One of my friends told me about it, but I couldn't find, you know, the information in advance online. I couldn't place an order. I actually might have to leave soon. And the wheels just kind of started turning at that point on maybe this is my opportunity to give back. So I won't spoil too much of it, because I know we're going to get into it, but that's kind of where I went from, you know, high school kid with a passion to, to give back to an opportunity that eventually I was able to fulfill.

[00:04:27] Sanjay Parekh: So let me ask you a little bit about your history then as a kid too. Did you ever do anything entrepreneurial growing up?

[00:04:36] Chin Weerappuli: Yeah. So actually, when I was in college, I was a social chair of my fraternity at Michigan. And I would do concerts to essentially raise funding for us to be able to do social events. So my sophomore year I had a concert with Mike Posner and B.O.B, who went on to be big name artists. Mike Posner and or sorry, Mike Posner and Big Sean, both from Detroit originally .And then senior year did another concert with Mike Posner and B.O.B and the concert company was actually called Sri Unit Entertainment to give a nod again to my Sri Lankan heritage.

[00:05:10] Sanjay Parekh: Nice. Nice. I love that. Love that. So you had a little bit of a taste of entrepreneurship and then started working, and then started this up. And so let's talk about The Underdog Family. Like, what is it? How did it get started? And what are you doing for people?

[00:05:26] Chin Weerappuli: Yeah, so I think that's a great segue to kind of pick up where I left off a little bit. Where The Underdog Family, it started in June of 2020. Again, in a period of time where we're dealing with a pandemic, a lot of people are dealing with social unrest, and the desire to really want to find things that they can give back to, things that they care about, something to give them, you know a passion and a purpose in a time where you really felt isolated.

So for me that moment when I went to the restaurant down the street from where I live, I knew that they served amazing food. I knew that they, as a restaurant had their recipes and all that other good stuff down. But it all of a sudden overnight became important to have a digital presence regardless of the business that you were in.

And small businesses as a whole, throw COVID out the window, as a whole, oftentimes you have so many people wearing so many different hats. They're already stressed. You know, you already have someone that's a cook, that's also taking order, that's also taking, you know phone calls.

And so now all of a sudden with the pandemic, there's no more in-person foot traffic, right? There's all these restrictions. You have to be able to reach people online. And so The Underdog Family really saw that opportunity where, what we could do is let the businesses focus on what they do best and take the digital stress of running a an organization in 2020 out of their hands by building, this is what we do now, we build a website for business.

We actually like to call it a digital storefront, because in addition to the website, we integrate your online ordering we integrate your social media pages also bring in your Google reviews so that when someone's visiting your site, they're actually visiting your storefront just digitally.

[00:07:07] Sanjay Parekh: Yeah. I love that. So so you're standing in line there and kind of come up with the idea to do this. Did you have any co-founders? Or did it start with just you?

[00:07:17] Chin Weerappuli: Yeah, well it did start with me. But it absolutely would not be where it's at without my VP and essentially my co-founder Derrick Knudsen. So when I had this idea, my initial thought process was Okay, I'm going to get a web designer, a professional photographer, social media consultant. I'm going to hire all these different third party vendors. And I'll just, I'll handle the cost and that'll be my contribution back to the community. But as I started to investigate, you know, each line item, it added up very quickly. You know, web design's not cheap photographers often charge by the hour.

And so it wasn't until I really met with Derrick Knudsen, who was just one of my good friends at the time, he had a background in the nonprofit space from New York. And we're talking about how we're going to make this work, and we both had such a big network in Denver, just fortunate to have a lot of friends that are doing really big things in their own time.

We're like, well, what if instead of hiring everyone, we just manage their time and allow them to give back, you know, maybe between two and six hours a month as volunteer time, because everyone was starving to be able to give back to their community, and now all of a sudden you remove costs from the equation.

You're only paying for the things that these websites charge, domain and hosting, brings it all the way down to just $500 a website for a business. And now now you're cooking with gasoline, you're building a network, you got really good, highly skilled professionals, but without the cost.

[00:08:42] Sanjay Parekh: Yeah, I love that. And for listeners Derrick Knudsen has previously been on the podcast. So if you're interested, you can go back and listen to his his episode as well.

Okay, so I, I think, you know, like everything you're saying resonates with me. I think all of us have seen this with restaurants, with small businesses where the entrepreneur is passionate about what they're doing, but honestly, they're just not good or they don't have the time to do any of that other stuff.

How are you filling that gap? How are you getting the people to come in and help you do all of those things? Because like you said, they're expensive. So what are you telling them? In terms of like, Okay, yeah, I'm only going to use you two to six hours a month. How are you convincing them? Or are they convincing themselves to come and work on The Underdog Family stuff?

[00:09:28] Chin Weerappuli: Yeah. So by and large, the volunteers that have been the most sticky for lack of a better term, the ones that have come into the organization, and then just refuse to leave are the ones that found us. So we've had, you know, a couple local publications do stories on us out in the community. Five Points Atlas comes to mind.

We've had a lot of Instagram promotions where people will just DM us and say, Hey, you know, I saw that you did a website for one of my favorite restaurants. I love what you're doing out in the community. Can I get involved? And from there it's kind of up to, you know, Derrick myself, the other people on the leadership team to find what they're passionate about and turn that passion into purpose where we know what they're going to be doing is engaging and valuable, but not overwhelming.

Some of the other tools that we have to kind of keep that balance is we do a monthly event as a team, a lot of amazing businesses and organizations in Denver support us with what we're doing where they offer unique experiences to our volunteers. A great example is we did a private tour at Denver MCA, which is the Museum of Contemporary Art.

Where we were able to see the gallery as a team, then go up to the rooftop, you know, enjoy a beverage or a snack, and you're basically building a community. So, what we like to say is it's not really work. It's almost friends coming together to do good things. And when you add that aspect of it, it takes away the burden and almost you're looking forward to it.

It's like, Hey, you know, I get to hang out with my TUF family once a month and oh, by the way, also impact all these businesses by doing great work in the community.

[00:10:59] Sanjay Parekh: Yeah, that's awesome. So the, that experience right there that you talked about were they a customer or client of TUF? Or were they just somebody that liked what you guys were doing and supported you that way?

[00:11:11] Chin Weerappuli: Yeah it's a great question. So, in the specific example with the Museum of Contemporary Art one of their community engagement directors, she was actually a frequenter of a couple of our partners saw what we were doing out in the community, just reached out to kind of network, and if there's one thing that I love more than anything else in the nonprofit spaces. Coming from a corporate background, you know, I'm kind of used to, to dealing with others in the space somewhat cautiously, right?

There's proprietary information and you know, there's sometimes conflicts of interest and you're protecting your own, your brand. But the nonprofit space, so many people are just there to help, you know, and even if it's not a traditional fit at first, you have a conversation, things start to marinate a little bit, and you're like, you know, I know I'm not directly involved in web design, but in this example, we'd love to get back to your volunteers. Or, we'd love to just kind of have you come speak about what you're doing out in the community to inspire others, to find their passion. It's just been really fun, fun to see.

[00:12:09] Sanjay Parekh: So, okay. I love all of this but let's dive into like how you started this. So you were working a full-time job, even though now all of a sudden you weren't traveling. So that gave you a little bit of flexibility to spend time on this. How did you balance that? You know, you're talking about your volunteers and how you're managing their time. Who is helping you manage your time and making sure that you weren't spending too much time between work and TUF and then getting burnt out. Like how did you balance all of that?

[00:12:36] Chin Weerappuli: Yeah. Sanjay, I'll tell you honestly, that. You know, maybe I wouldn't have done exactly what I did if I could do it all over. If I removed these headphones, there's a lot of gray hairs there that weren't there just two years ago. Because actually as I started TUF in June, I was also entering an MBA program at the University of Michigan in July. So I kind of had these three buckets going on at the same time.

But the irony of it was, you know, had my full-time job was going back to school, but TUF and The Underdog Family is almost what kept me refreshed and recharged, because I realized when you do something you're passionate about, oftentimes it doesn't drain you know, your cup, it fills it. So for me, the time management side of things was so passion driven that I rarely felt like, oh, I gotta finish my 10, 20, 30 hours this week for TUF.

And we really wanted to keep that mindset throughout where we never have a volunteer join the organization and say, Hey, we really need you to work on this, knowing that it's not why they came to find us. We'll do whatever we can to really plug people in on what they care about and it tends to allow people to manage their time in ways where it's sustainable.

[00:13:45] Sanjay Parekh: Yeah. Yeah. I love that. So let's talk about the organization a little bit. Before we started recording, you made a comment where TUF doesn't have any paid employees. So everybody is a volunteer all throughout the organization. So in terms of funding, are you, did you raise any money? Are you funding it? Or do you need to fund it at all?

[00:14:06] Chin Weerappuli: Yeah. So in our first year I'm glad you pointed out the fact that our staff is all volunteer based because they're so proud of that, to be able to say that every dollar donated goes right back into the community.

So in our first year in 2020. You know, we started in June. It took about eight weeks to get our 501c3 approved. During that time we didn't even accept donations. It was all self-funded by, by myself to get us off the ground, to start a marketing presence. We actually built two websites for businesses at that time because you know, Derrick and I, we felt like we couldn't wait.

You know, these businesses needed support right now. We knew that with every week that goes by in a pandemic that's revenue loss. You know, stimulus checks are drying up, pPPs drying up, so we wanted to get going as soon as possible. And in that fundraising period where it was all just kind of fronted, we realized how much impact we could do with less.

So as soon as we got our 501c3, we already had actual credentials that were on paper of this is what they were able to do without any external funding. We went to corporate donors banks in particular there's an initiative at the Google office in Boulder, where they do a holiday match, and showed them these numbers.

And there was just a massive massive desire in the community to give back and support something like this. So even though we don't have employees, there are still costs that we need to cover. You know, domain and hosting for websites. We like to do marketing events with our partners where we bring people together in the community.

So we do need funding, you know, and if you're out there listening, you can donate at iamtuf.org/donate. But every penny goes right back to the community. So it is less. And in from that first year, in 2020, to now our operating budget has actually four Xed. Our impact has gone through the roof.

Our volunteer base has gone from about four people full time. Or when I say full time, four people working on our operations team to about 25. So we feel like the sky's the limit and things are really moving in a positive direction.

[00:16:02] Sanjay Parekh: So just so listeners get a scale. What is your operating budget now for 2022? Like what's the target spend?

[00:16:09] Chin Weerappuli: Yeah, so it's around 35,000 right now. In our first year we raised, you know, around six. And what we anticipate is, as word continues to spend our volunteers base continues to grow you know, we're talking about, again, $500 for a website, $500 for marketing initiatives that 30,000 goes a long way. It helps multiple businesses and it really makes an impact in ways that maybe other organizations can't replicate.

[00:16:35] Sanjay Parekh: Yeah. Yeah. I love that. So, so for 2022, with a $35,000 budget, how many businesses do you see impacting, creating websites for them and all that?

[00:16:46] Chin Weerappuli: Yeah. So we have 15 businesses that we work with consistently. Right now, those are businesses that we've built websites for, that we've trained them on how to maintain their website, we've integrated various tools for them as well. We are working with partners Mile High United Way has been a great partner, the Denver Economic Development Office, to bring in more restaurants and businesses that could use our support.

But do so when all parties involved are ready and I think that's been our biggest quote standpoint where. Those 15 businesses in the first year and a half took about, you know, anywhere from six months four to six months to build out. What we're working towards is as our budget continues to expand, utilize our partners to streamline this so that we can really hockey stick up and launch anywhere from, you know, 40 to 50 businesses a year moving forward.

[00:17:37] Sanjay Parekh: So, okay. I love that. But right now you're only in Denver, right? All these businesses are there. What's the thoughts of expanding? Because this is not a need that only exists in Denver, right? It's across the country.

[00:17:49] Chin Weerappuli: Yeah. And actually something that was a really great opportunity is during my time at the University of Michigan's Business School, we did a semester based project on The Underdog Family and what expanding would mean. Where we weighed out should we launch different TUF chapters in various cities? Should we essentially you know, have us travel across the country and visit different cities? And what we realize is the biggest thing that we love about TUF, and we talked about it already here is community, right?

People come together, they're willing to work pro bono because they feel so invested in the community that they're in. One thing that I looked at specifically being from just outside Detroit is there an opportunity to partner this in Michigan and in Detroit specifically?

And we see that where there's a United Way in Detroit, you know, we've already been partnering with the United Way here. We're looking to leverage our partners so that we have boots on the ground. And then we kind of come out and essentially train those organizations on our secret sauce. It allows us to keep the community feel here.

It allows our volunteers to be able to go out and see the country be in different cities and the businesses that we end up supporting, they don't need to just get on the phone and call Denver, they would have an ecosystem of both in house, along with us supporting them from afar.

[00:19:06] Sanjay Parekh: I love that.

[00:19:09] Adam Walker: Support for this podcast comes from Hiscox. Committed to helping small businesses protect their dreams since 1901. Quotes and information on customized insurance for specific risks are available at Hiscox.com. Hiscox, the business insurance experts.

[00:19:25] Sanjay Parekh: Okay. Let's talk a little bit about kind of the mechanics of what you did here. And thinking back now in retrospect. And I'm not sure, I'm not sure if you're going to have an answer for this one. But looking back at it, what was the biggest risk that you feel like you took in building this out?

Like there wasn't really a financial risk because you've done it with so little money. So there, there was no downside there. Was there like some other risk that you, like looking back now that like, oh, that could have tanked the whole thing if we hadn't come out on the right side?

[00:19:54] Chin Weerappuli: Yeah. I mean, I know it's a little emotional, but for me, the biggest risk was getting my bubble burst on, I was so sure that when I launched this, there was going to be businesses that wanted to work with us, volunteers that were going to line up, jump right in, and we were going to take off to the moon and be able to support the community within, you know, weeks.

Surprisingly, what I saw was a bit of a process there, especially with the businesses. Because there are a lot of groups that come in promising support that oftentimes with this small business system, either don't deliver, or they're looking at it from a different angle, you know, maybe a debt equity model where if the business doesn't see an increase in revenue, then all of a sudden this company's able to kind of grab their business right from under them.

So in the first couple months we actually saw a lot of trepidation and it took trust building on our side to really, you know, be patient and it wasn't until that those first three clients took off for us to be established as an organization.

And you mentioned the financial aspect, sure, you know, that wasn't overly burdensome. But to launch something that fails when you have the most altruistic of models, would've been, you know, devastating for me just on a personal note. And then from a volunteer standpoint, if people weren't coming in, my faith in humanity, Sanjay, would've suffered a little bit being like, yo, here's your opportunity to give back to the community.

Thankfully, both those things resolved themselves where, you know, we don't really struggle to attain volunteers. We have a very inbound focused model now, and anytime we do an event, we have all of our partners rushing to come out to, to advocate for us. So I would say that risk, thankfully did not come to fruition.

[00:21:34] Sanjay Parekh: That's great. So, so thinking about both of those things. Now that you've kind of gone through that cycle and experience and come out the other side. Is there something that you would've done differently to maybe help shorten down that timeframe of figuring out this kind of chicken and egg problem that you had on both sides?

[00:21:51] Chin Weerappuli: Yeah, so our first first project dragged on a bit where, as I mentioned, there was just, there's a little bit of trepidation especially from the business side. And when we got over the hump, it was actually Derrick and I, we went back, we were told that, you know, they're not going to have the time to work with us.

You know they definitely got I don't want to say scared. But they got skittish to the point where it wasn't worth it. So we went back, just to my apartment, we pulled up all the things that we could find on various sites, third parties, Yelp, GrubHub, you know, anything with their menus, and we built a website off of public data and then displayed it to them.

And they're like, this is amazing. We're so sorry. We now see your vision. And I think, again, what we could have done better upfront is painted, like shaped the path a little bit more for these businesses. Just understanding what they've been through as a locally owned small business in the community. And made it a little easier to trust us from the start.

[00:22:46] Sanjay Parekh: Okay. Yeah. That's great. Okay. So let's talk about advice now for people that are listening to this podcast and thinking about wanting to do a side hustle or small business and kind of launching it full time. What advice do you have for somebody that's doing that?

[00:23:03] Chin Weerappuli: Yeah, my biggest advice is, you know, one of my favorite quotes is attack each day with an enthusiasm unknown mankind. It's University of Michigan quote from Jim Harba.

And the reason that I love it is because, you know, you get up there, you grind, you have to have something that you are starving for. And with TUF, I definitely had that passion from the beginning, but somewhat underestimated the resistance I would face. We just covered that.

If you don't have something you're truly passionate about, when you meet that resistance, it's going to be really easy for you to just kind of give up and find something else that maybe is easier or you feel, you know, that you can maintain quicker. Biggest piece of advice for anyone that's looking to start a side hustle is again, find something you're passionate about so that it's not just a grind. It's something you wake up looking forward to.

[00:23:52] Sanjay Parekh: Yeah, that's, that is great advice because a lot of times, I don't know how you feel, but it becomes not work anymore. Right. I don't know if this, does this feel like work to you? Or does it feel like something you just do?

[00:24:04] Chin Weerappuli: No, for me at this point, it's just something I do. You know I have my TUF shirt on right now. I love to just walk through the neighborhood, stop by, visit a lot of our partners, and I get hugs. You know, they'll always offer me free food that I vehemently deny. But that's how I feel.

You know, we initially started off as The Underdog Foundation and we rebranded to The Underdog Family because we feel like this is not just a charitable body that gives out grants. This is an organization that brings people together with a family mindset, where I don't want you to just succeed for my benefit. I want you to succeed the same way that I want my brother, my parents, my niece, you know, my family to, to thrive.

[00:24:43] Sanjay Parekh: Yeah, that's great. Okay. Last question. How are you managing the stress of doing all of this? Right. You've got business. You've gotta, you've gotta pay, you're on a sabbatical right now, as we're speaking. Like, how are you managing the stress? Like what do you do to de-stress and of relax? You know, cause if you go out to the restaurants that you're serving it's almost still kinda like work even though you're there for a meal. So, so how are you managing all that?

[00:25:10] Chin Weerappuli: Yeah, I mean, I think the biggest thing again is to integrate anything that helps you reset into your day to day with whatever work or hustle you're trying to do. So for me, it's people. For me it's interacting and networking with both those that I know and maintaining those relationships, but also getting out in front of in front of others.

And, you know, as someone that's a little bit more extroverted that really does recharge me. So when I wake up and I look at my meetings I try to space it out where I have something to look forward to, even if it's work. The other thing, you know, is try to get your six or six to eight hours of sleep.

You know, don't be pulling all nighters. And I try to walk everywhere when I go to visit these partners. So I think staying physically active and physically fit is important, too. So that you are in the best state of mind to be able to give it your all at all times.

[00:26:01] Sanjay Parekh: That is fantastic advice. Thanks so much for being on this show, Chin. I think all of us are excited. I'm excited about getting The Underdog Family here in Atlanta.

[00:26:11] Chin Weerappuli: I love it.

[00:26:11] Sanjay Parekh: We'll see that someday soon.

[00:26:12] Chin Weerappuli: We'll add to the list.

[00:26:14] Sanjay Parekh: There you go. Thanks again for coming on.

[00:26:16] Chin Weerappuli: Thanks so much, Sanjay.

[00:26:21] Sanjay Parekh: Thank you for listening to this week’s episode of the Side Hustle to Small Business Podcast, powered by Hiscox. To learn more about how Hiscox can help protect your small business through intelligent insurance solutions, visit hiscox.com. That's hiscox.com. And if you have a story you want to hear on this podcast, please visit Hiscox.com/shareyourstory. I’m your host, Sanjay Parekh. You can find me on Twitter at @sanjay or on my website at sanjayparekh.com.