Heroes in Business - Mark Josephson, CEO of Bitly & Castiron Co-Founder, fmr. Senior VP of Revenue & Marketing at AOL

Episode Date: March 14, 2025

Join us for an exciting interview with Mark Josephson, CEO of Bitly, Co-founder of Castiron, and has served as Senior Vice President of Revenue and Marketing at AOL, as he shares his journey and insights with David Cogan, the renowned host of the Heroes Show and founder of the Eliances community. Don’t miss this chance to hear from a leader in digital innovation! castiron.me

Up in the sky, look, it's captivating, it's energizing, it's Eliance's Heroes. Eliance's is the destination for entrepreneurs, investors, CEOs, inventors, leaders, celebrities, and startups. We're our heroes in business aligned. Now here's your host flying in, David Kogan, founder of Eliance's. That's right and boy do we have a full day today so really appreciate it. Make sure you stay tuned the entire time. I'm going to tell you who we have coming on next but later on we've got the co-founder of Zillow

coming on, the co-founder of Hotwire coming on, NASCAR race car driver. I'm not going to share with you who's that name yet, but he also is the owner of the team, owner of the car. You'll recognize his name, but I'm very excited to have our first guest here today because remember we share the secrets, the secrets of what makes them so successful. And I'm so excited. We have with us today Mark Josephson.

Now he is the former CEO of Bitly. Clearly you know Bitly, what they've done like six, I think I got the stats here, 600 million links you shorten per month. Like that's just phenomenal. Like how did you get the role for that position as CEO? Sure. So I was CEO of Bitly until about two years ago. And so I joined the company in 2013. And so much of, first of all, thank you for having me. I'm so excited. The intro music was awesome. I'm all fired up. So much of success in building a company and growing a career is about relationships

and how you treat relationships, how you treat the people you work with and the value that you add. So my job at Bitly was through my relationships in the industry, I've been building technology businesses in and around New York City for 25 years. So I got the chance to work with some investors with whom I had worked before.

Yeah. And I mean, you've been quite a career. I mean, you've been with about.com also and what GM at about.com, right? Yeah, but started working with that company back in 1996. And then spent five years helping to scale it up through the dot com boom, scale it back during the dot com bust, and really learning how to build and manage a company and a startup in a high growth phase that's, you know, hands on experience, can't beat it. So Mark, then what got you to start? And by the way, I want you to steal the thunder of what you're doing now, because I love it. And it's definitely something that's needed.

I love the site. I love what it's doing. Mark, please steal the thunder of what you've co-founded. So thank you. We started a company called Cast Iron. Cast Iron is a mission driven company that helps entrepreneurs become successful business owners. And we start with entrepreneurs in the independent food space. These are entrepreneurs who are making food out of their licensed home kitchens or out of commercial kitchens. And our entrepreneurs, our artisans, are not your typical entrepreneurs when you think about it on shows like this and in the trades, if you will. These are entrepreneurs by necessity.

These are people who aren't necessarily connected to the systems of success that East and West Coast entrepreneurs tend to think about. So we wake up every day trying to figure out how to help these passionate, whether they're making sourdough bread or custom cakes or cookies or kombucha or hot sauce or meal prepping. How do we help them start and launch an e-commerce business? What are the tools they need? What are the resources they need?

What's the easy button that they can press to help get themselves from zero to one? Yeah, you know, when I went there and I heard you were coming on and I was studying and looking at your site, it's like one of those, aha, why didn't I think of it? Like something, you know, somebody created the crafts with Etsy, right, that she morphed into things and so on and so on. But you created it for those that are chefs cooking doing their own. And again, like you said, in a kitchen that's, you know, right? Well, that they're able to, you know, yeah, licensed and regulated. Yeah. So I mean, and it's like, I know so many people who do that, like a lot of people, you know,

at the fairs, right? That, you know, you see all of these that have been popping up that are extremely popular. Are those your type of potential clients? Exactly, yeah. That's exactly who we're talking to. Our customers are doing this, largely already doing this. They're just doing it not as efficiently as they could. You'll see them on Instagram with DM to order

or on Facebook saying, fill out my Google form to get your custom cake. And that just means they're not streamlined. They end up getting into this business thinking, I make the best cakes in the world. Everybody wants them for the birthday parties. I can go into business. And the truth is they can, but they end up spending 75% of their time doing things that aren't related to making the product and delivering the joy that a great cake can do. They're doing back office stuff and administrative. It's just not that software can solve that problem. Right. But Mark, how did the idea even become like, what was the exact time spark that it was like,

yeah, this is needed. Yeah. So a couple of things. One, I partnered with a, with a venture fund in Indianapolis, HiAlpha, uh, who are some of the smartest, nicest, most creative folks out there. And we went through a process together called sprint week where we took a germ of an idea and prototyped it, took it to market, tried to figure out if we had some legs and it was in that process. That we were looking around at the

food vertical and how consumer behavior has changed, how in the pandemic, the number of restaurants that went out of business, the number of restaurant workers who lost their job and food service workers who lost their jobs, and some of the other macro trends. So we watch very closely things like Substack and reporters leaving big brand publications to go independent. And that's a very similar motion that we see happening with Cast Iron. And then honestly, I had a friend who made

artisanal ice cream and sold it on drops on Instagram for 10 bucks a pint and they sold out all the time. I have, I knew this really talented woman in my town who was a classically trained pastry chef Who moved to the suburbs started her family and was delivering hot fresh cinnamon rolls every saturday morning and This is a thing people are doing this and

we're so like Beyond passionate about helping them be successful and get those first steps going? Sure. And I'm sure everybody wants to send you samples because I'm talking with Mark Chosesson, former CEO of Bitly, co-founder and CEO of Cast Iron. Now, you see the link below, you can go to castiron.me, castiron.me, because you're listening, watching me. David Cogan, host of the Alliance of Heroes show. The only place where entrepreneurs align. Make sure that you check out our past interviews by going to alliances.com. That's E-L-I-A-N-C-E-S dot com.

Once again, the only place where entrepreneurs align. So what advice do you have for someone who's really looking to, you know, right now we're going to have a lot of people listening and watching and they're like, yeah, you know, I've got this business, I'm trying to take it off. Maybe it's in the, you know, something that would match of what you provide with Cast Iron. They've got a lot of demand in the local area where they're at. Maybe they're making cookies, whatever it have you be. How do they apply or how do they get on the platform? Sure. So if you're passionate about food and a talented artisan and think you can start to sell it or already are, come to CastIron.me, click on apply now, and you can get started for free. Our product is free.

We only make money when our artisan sells something. And if you're not quite ready to press get started, look at our blog. Our blog is hundreds of articles written about how to get started, how at our blog. Our blog is hundreds of articles written about how to get started, how to price, how to test, how to explore what the local rules and regulations are. Really a one-on-one on what it takes to get started and to do this. So, and we also have a community of other artisans

that you can talk to and network with and learn from. So we're trying to give all the resources that you can have to help you get rolling. Mark, we have a question that was submitted and this is in regards to selling on CastIron.me and I'm sure others actually probably have the same type of question. How do you know what to price your item at when you're listing it? Yeah, pricing is one of the biggest traps we see our artisans falling into across every category, really. You know, there's lots of different pricing strategies. The most important thing

that we like to advise our artisans on is understanding their costs, really understanding their costs. And the biggest actual trap they fall into is don't forget to pay yourself. So you have to assume you're paying yourself for your time plus the margin on your on your ingredients And so and don't be afraid to price your stuff at a premium. It's artisanal. It's special. It's valuable It's celebrating and supporting local businesses, which are the pulse of the local economy and the global economy really so stand up for what For a price for a nice strong price for what yourself what you're selling Mark, I want to forget don't forget to pay yourself what for a price for a nice strong price for what you're selling.

Mark, I want to do don't forget to pay yourself. Very important. Make sure you pay yourself so you could survive and continue to do it and grow. Yes. Have you seen some of the some of the ones listing on your on your site, just like really start to take off? Like, maybe help us understand like, why are there some and what are those sectors that are just going skyrocketing versus others? Yeah, so we're still early, so we're learning a lot about the different sectors, but I'll tell you, I never knew there were so many custom sugar cookie makers

in the world, and how many people buy each other really beautifully designed cookies for Christmas, for Thanksgiving, we're seeing Valentine's Day now go crazy. It's really, really amazing to see the creativity of folks. The things you can design on a cookie are remarkable, really remarkable. The sky's the limit. I can't wait to go order some. Make sure again you go to CastIron.me, CastIron.me. Mark, I want to do some snooping now. We're going to do some snooping. We're in your, I believe your office or something like that. I see a number of pictures. I see a column of pictures, different things. What's something maybe unique, something treasured,

something that, you know, hey, God forbid there were to be a fire or something like that. You're like, I got to take this item out. Or what are you most proud of where we're snooping around in your old office area? Gosh, one of I most proud of is probably the deal trophies from the two companies that I've helped build and sell with my teams. So that's Bitly and a company called Outside Dot In. But that's the easy answer. The thing that I care most about and was most thinking about,

I don't know if I can turn my camera around. Oh, yeah. Definitely. This is a present I got for my 16th birthday, which was many years ago, which is a giant Bruce Springsteen born to run album And this has followed me everywhere since I was 16 years old. My wife won't let me put it anywhere but my office and

If I follow one true boss, it would be Bruce Springsteen. So that is coming with me everywhere I go. Phenomenal, phenomenal, phenomenal. Do you have kids? I have three boys, yeah, 1917 and 14. Wow. So what kind of maybe secrets do you share with your three boys about being able to? Because you have and you continue to have a very successful career. You've been with some major companies that people know about.

Now again, and I mean, from Bitly now again, is with the CEO and co-founder of Cath Iron. What kind of things do you share with them about how to make their mark in the world and society like you have and continue to do? Well, that's kind of you to say. I learned everything about being an entrepreneur and everything about being a father

and a good person from my parents. My dad was entrepreneurial and my mom was one of the kindest people I know. The thing that my wife and I talked to our boys a lot about being kind. And kindness, it can come in big ways and have big ways to, you know, big examples of kindness, but they can also be little things,

just acknowledging somebody who might be having a tough day or did a particularly good job on something that makes your job easier or you like the t-shirt they're wearing. We talk a lot about kindness and kindness means if you're a kind person and looking for opportunities to be kind, then I think that translates really well to business because you can be empathetic and really understand your customer's needs and try to solve those problems that they have. And so we don't talk about business as much as we talk about how to leave interactions

and with the people you interact with feeling better and in a better spot. I love it. I love it. Well, Mark, you created a better way first to track and use website addresses with Bitly Italy now creating a way for culinary professionals to elevate their business Stop worrying about building your own website and managing all that stuff. Why do that? Cast iron dot me and creating it that's the hero Mark Josephson former CEO Billy Kofan

cast iron go to castiron.me and we're gonna have to have you back and try to introduce you to Bruce Springsteen how about that? I'm back anytime say this when and where. I love it I love it.