Ish: I am. Thanks for having me, John.

John: Ish is the founder and CEO of the award-winning marketplace Open Sponsorship, a VC-backed startup connecting brands like Glass Door, Verizon, and DraftKings to pro athletes, teams, and events. Ish was recently named on the Forbes 30 Under 30 list and is an expert on sports sponsorship. Ish, take a minute. Fill in some gaps from that intro and give us a little glimpse of your personal life.

Ish: Absolutely. Thank you for the introduction. I was a sports agent. Prior to that, I had been a management consultant. I graduated from Oxford and then I had a big career change, as I’m sure many of your listeners have. I decided that my passion was sports. Someone had recommended why don’t I look at sponsorship because it’s the backbone of all sports. I took their advice. I flew to India, thinking if I’m gonna do one big change why not do two? This was back in 2009. Became a sports agent. Fast forward, did very well, moved to America, and then one day I had this moment. I thought why is our industry so difficult? I looked at other industries and their recruitment (dating, real estate) where there have been these agents who sat in the middle, and thought why don’t we have Airbnb or Match.com for our industry? That’s what we started.

John: One thing that I’m curious about is what you consider right now your area of expertise. What is that?

Ish: It’s interesting because I’d say that we sit at the cross section of sports – obviously, sports is a big one for us; for me, I’d say business of sports, particularly. Don’t start quizzing me on the 1980s World Series statistics or anything like that. The business of sports is a big one. Marketing because sponsorship is a form of marketing, and then I would say entrepreneurial as of now, given that I’ve been a tech entrepreneur for just over two years.

John: What don’t we know about sports sponsorships? ‘We’ being a typical entrepreneur that you really think we should know.

Ish: That it’s accessible and it’s completely justified. To be honest, it’s so much that you don’t know as an entrepreneur that you think, “Well, why would I need to know?” But 14 percent of all marketing spent in North America goes to sponsorship and 70 percent of that is in sports. But yet that 14 percent is heavily made up of your Fortune 500 or even higher: your Nikes, your JP Morgan Chases. That’s because most people think sponsorship equals a million dollar deals for Steph Curry or LeBron James. That’s not the truth. There are New York Jets players sitting in New York who would love to be working with Silicon Alley and the same for Silicon Valley and the same for Minnesota or Austin.

Sports sponsorship is valuable. It works and it’s really fun and it’s accessible and it doesn’t cost an arm and a leg.

John: You say it’s really fun. Why don’t you give me one of your most fun examples of this actually working in a real case, a real live situation?

Ish: We had a startup out in Chicago who had one of – I think it was one of the Bulls players tweet about their brand and say – it was a paid endorsement deal, a couple of hundred dollars. This player was like “Here’s a cool startup in the area.” What their business was was to if you were out of your home state then they would collaborate – it was almost like Meetup for fans outside of their home state. Obviously, it’s very hard to get on cable the matches that you wanna watch if you’re not in that region. It was like a Meetup and you meet these people and you go and watch these games together. They said, “Told my friends outside of Chicago – sorry. Told my fans outside of Chicago use this app to go find other Chicago fans and get together.”

Just on the back of that one tweet they raised money, they won competitions, they got all this validation. The reason was is because at the end of the day when you turn around and say, “Hey, look this Bulls player believes that we’re the best place to go for this,” everyone else just believed it. Obviously, the player did it because they liked the business, but at the same time it’s a sponsorship deal.

John: I guess a question that I would have and probably a lot of other people is why is this professional MBA player who’s making hundreds of thousands, if not millions of dollars a year in the most likely case, why are they doing a tweet for a couple hundred bucks?

Ish: Great question. The main reason why is because sponsorship is not done just for money. That’s influence in marketing. That’s what you think of when you think of influence in marketing: people who become rich because they’re famous and they use their brand. Athletes have always been doing sponsorship, well before influence in marketing; obviously, music as well. There is a component which is a nice money to have – Roger Federer is one of the highest-paid athletes in the world and a lot of that is based on sponsorship.

But for a lot of these NBA players who are not LeBron James or not Steph Curry, for them it’s just a case of kudos. A great example here is during the NBA finals last year, the playoffs, there was a guy on the Hawks called Taurean Prince. We did a peanut butter deal with him. He did like peanut butter, so it was quite fun. He posted it on the morning of his last playoff game. On his comment stream, it was, literally, fans being like “Oh my god, man. You’ve made it!” This is a guy who’s playing in the finals at night, and people are going, “Oh my god, you made it! Look at you! You’re in the big leagues now.” That’s how athletes think about sponsorship and brand personality, which is it’s cool. Someone wants to support me. I rub off on them; they rub off on me.

And another way to think about it, especially – I was at CS last week with a lot of NFL players. A lot of them are thinking about it because it means that they’re defining their brand now, so when they finish playing they look at guys like Shaquille O’Neal or Byron Davis and they think, “How do I become that?” Sponsorship is one of those ways of defining a brand.

John: Great example, Ish. Thanks for breaking that down.

Let’s go in a different direction, now. Your journey has been one of ups and downs as an entrepreneur. I want you to take us to the lowest-of-the-low business moment that you’ve experienced. Tell us your worst entrepreneurial moment.

Ish: It was so funny to think of this because you never really have one – fortunately, it’s not like I’ve just gone bankrupt or I don’t have one of those turning points in the business. But there was a good six months of low. There were so many different points in that time that I could pick. Obviously, I’m only gonna pick one, not to bore your listeners too much.

One thing that really stuck out to me: obviously every entrepreneur has problems raising money at first and defining business and thinking about subscription models and whatever else. One of the worst moments for me was probably hiring. I really struggled with that at the beginning because you’re creating something new. It’s not like you can say, “I’m creating a new CRM so let me look at someone who’s already created a CRM” and trying to hire someone from that. No one’s done this before. Who do you go for, an ex-sports agent or go for a techie or whatever it may be.

I remember there was this moment in time where I hired someone fairly early on into the life of Open Sponsorship. He walked in and about one hour in I was “Ah, this was not the right person.” You’re such a small team that you can’t make up for the fact if you’ve hired wrong. By the end of the week I had fired him. It was really tough because you are so optimistic when you’re hiring as a new entrepreneur because you want – you’re like, “Wow! You wanna work for me? That’s amazing! Let’s make it work.” Interviews are such very nice places where everyone says the right thing and you’re listening for the right thing and that kind of thing. Then they walk in and you’re putting them into your payroll system and you’re like, “What I am doing? I really didn’t want you on my team.”

I’d probably say my worst moment was that point where day one, only two hours in, one hour in I was like “I’m gonna have to get rid of you. But when is the right time? Tomorrow? The end of the day? The end of the week?”

John: Like now. This very moment in time. Fire Nation, it never gets any better. It only gets worse. Help yourself. Help that person. Get them out the door. They’re not the right fit. They’re not gonna thrive in that situation. What’s the one takeaway, Ish, you wanna make sure that we get from that story.

Ish: When you’re early on it’s really attractive, especially when people come to you and say, “Listen. I’m good for that role.” I call it opportunistic hiring, where someone fits something that maybe you weren’t 100 percent looking for but you’re like “We’ll make it work and you’re ready to work for lower salary, and you’ve got a bit of experience that I don’t have.” I would still say – I don’t like that phrase, hire slow fire fast. I don’t think it’s about hiring slow. That can kill you. I think it’s just about making sure that you’ve not got your blinders on and you’re thinking, “Am I actually, day one, am I actually gonna want to work with you? Do I want you to sit next to me? Do I want you to sit next to me for the next one year, at least?”

Really think about those things rather than just saying, “I’ll give it a go,” like I did. Give it a go, come in, and then realize minute one this wasn’t right.

John: What’s one of the greatest ideas you’ve had to date? One of those ah-ha moments that you’ve turned into success. Tell us that story.

Ish: When we first started I looked at Airbnb and I thought, “They’ve got a great marketplace. Let’s do exactly what they’re doing.” So, it was 3 percent commission and I followed their metrics and followed their UI and everything else. What we realized is is there aren’t many places where people will come on and just use it for fun even if they have no intention of buying. But when you have athletes on one side that is what happens. We called it ‘kick-a-brands.’ They’d come on the platform and they’d message athletes or these agents and be like “I love you” and “Here’s my product and I have no money but will you work with us?” It was really difficult because you’re like “How can I monetize this? What’s going on? No one’s taking it seriously.”

One thing was we set up subscription, which was really difficult because as a previous sports agent the word subscription didn’t even exist in my vocabulary. And the second thing was we thought if we’re gonna have subscription then we have to create [inaudible] [00:10:17] engagement and all the owners come in on the brand. So, we set up what we called a campaign feature. This was quite early on and it’s been perfected a lot. Essentially, the same way that previously, back in the day, a recruiter would have to look at a whole vast amount of potential employees and figure out who was the right one and look at resumes, and then suddenly platforms like AngelList came along or even [inaudible] indeed. They were like we’ll let the employer build a job posting and that applicants supply – we take that for granted but that was a very novel idea when it first came to recruitment.

In the same way, we have our brands complete this campaign about who they are and what they’re looking for and then our athletes and agents apply. It’s changed the whole way that we do things. It’s changed engagement. It makes the storytelling easier. It was such a simple idea but it’s probably one of the biggest pivotal things about why we’re so different.

John: Fire Nation, what’s working for somebody else might not be the exact ingredients or recipe for your success. You always have to be testing. You always have to be having your finger on the pulse and be iterating on what’s working. Don’t be afraid to pivot.

Now, that was my big takeaway, Ish. What do you wanna make sure our listeners get from your ah-ha moment?

Ish: I think you said it absolutely perfectly, which is always be testing. And also, really understand… Don’t sit back and think, “That’s an anomaly.” When brands started coming onto our platform and messaging all these athletes I could have been like “They’re just small brands and we’ll get the big brand,” but we didn’t say that. We thought this isn’t the behavior I was expecting. When the behavior you’re expecting doesn’t happen, you have to fix it. Too many people close their eyes and go, “Well, you know, that’s an anomaly.” That’s not an anomaly; there’s something going wrong if the behavior – even if you have a product and people aren’t using it the right way, there’s something that you need to change. Don’t blame it on the end user.

John: Fire Nation, if you think Ish has been dropping value bombs, you’re right. And more coming up in the lightning round when we get back from thanking our sponsors.

Ish, are you ready to rock the lightning rounds?

Ish: I’m ready.

John: What was holding you back from becoming an entrepreneur?

Ish: Everything. For me, I kind of dove in and I didn’t realize how hard it was to build tech. I imagine people now realize it’s even harder and they find partners and everything else. I would say that, not having the CTO (I’m non-technical) was an issue and it probably delayed our launch by a good nine months. I knew I was an entrepreneur because I was planning it but it definitely delayed the business, not being technical.

John: What’s the best advice you’re ever received?

Ish: Don’t think of yourself as asking for a favor. Think about what good you are bringing to the other person. If you can’t think of any good that you’re bringing to them then probably don’t ask for the favor. But try and change your mindset.

A great example of this is let’s say I know someone who could give me an introduction for sales. Previously, I might have thought, “Do I really wanna ask them for a favor of introducing me to that person? How does that put them in place?” Now, I think about it as the person they know is missing out if they’re not connecting with athletes because I firmly believe that that brand is perfect for what we do. Therefore, the person I’m asking to introduce me is actually doing them a solid, as well. They will be thankful that “Hey, you introduced me to this awesome company and that’s helped my business.”

John: What’s a personal habit that contributes to your success?

Ish: I’d probably say lead by example. I have no fear about working harder than anyone else. On my team I’ve got no ego in terms of coming in first or leaving last and working at the weekends when everyone else isn’t working. So, I don’t demand people to work harder than me. I just hope that see me working harder and that makes them work harder, too.

John: Recommend one Internet resource.

Ish: Probably controversial, here. I would just say Google. There is no question that someone hasn’t answered on the worldwide web. There is no excuse to not know anything. Your best friend is Google, if you know how to use it. Even to the point of type in the right words at the right beginning of the sentence to get the right answer. Don’t be scared to look things up. Keep hunting until you find the answer. It might be on page three because everything on page one and two is not that relevant. Find answers using the Internet.

John: Recommend one book and share why.

Ish: I love Ben Horowitz, The Hard Thing About Hard Things. It’s almost like a manual for an entrepreneur, for a CEO. The beauty of it is it’s not – I read it about a year ago and then I re-read it about two months back. There are different parts of the book that speak to me now than spoke to me back then. Also, it’s a very honest book into how he was feeling. I think that’s really nice, to be able to say everyone goes through these ups and downs.

John: Fire Nation, I know you love audio, so if you’re currently an audio member, head over to eofirebook.com and you can listen to this book for free.

Ish, I wanna end on fire, so give us a parting piece of guidance. Share the best way that we can connect with you and then we’ll say goodbye.
Ish: Thank you. Twitter, LinkedIn, I’m Ishveen Anand everywhere that you can see me, and obviously, if you’re interested in what we’re doing at Open Sponsorship then please reach out by email, as well.

John: A parting piece of guidance.

Ish: Don’t give up. It’s a really tough journey, no matter – you raise money, it’s tough. You don’t raise money, it’s tough. You employ someone, training is tough. It’s always really tough. Don’t give up and surround yourself with great resource. That could be great podcasts, like yourself; the Internet with answers; or a solid group of friends.

John: Fire Nation, you’re the average of the five people you spend the most time with and you’ve been hanging out with IA and JLD today. So, keep up the heat and head over to eofire.com. Just type ‘Ish’ in the search bar and it’s gonna show right up, the show notes page. Get on over there. There are the best show notes in the biz: timestamps, links galore.

Ish, thank you for sharing your journey with Fire Nation today. For that we salute you and we’ll catch you on the flip side.

Ish: Thank you.