Ishveen Jolly, founder and CEO of OpenSponsorship

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Ishveen Jolly is the founder and CEO of OpenSponsorship, the largest two-sided marketplace for sports sponsorship which helps connect brands to athletes. Ishveen believes that sponsorship is the best form of marketing which brands can leverage to tell their story, whether that is by putting their logo on a footballer’s shirt or using an athlete’s social media presence to bring a brand to life. OpenSponsorship allows brands and athletes to connect in an easy, accessible way that simply didn’t exist before.

After working in the sports industry for several years, Ishveen became frustrated with the inefficiency of the sponsorship system. So many athletes are financially unable to work without sponsorship and, despite being an industry worth sixty billion, sponsorship had seen almost no innovation up to that point. The solution Ishveen designed was OpenSponsorship which launched in 2014. Since then, over 7500 athletes have connected with brands through the analytical, AI based matching and proprietary ROI tracking of the platform. In many ways, OpenSponsorship is the or Airbnb of sponsorship, securing Ishveen a place amongst Forbes’ 30 Under 30 (2015) and Inc. Top 100 Female Founders (2019).

What is your background? What made you decide to become an entrepreneur?
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Playing sports has always been the common denominator of my life – having grown up in Manchester, I chose to apply to Keble because I knew it was one of the sportier Oxford colleges. All through University I was running from one game to the next and, when I graduated, I wasn’t sure what I wanted to do next.

During Uni, I’d interned at a big company in London and knew immediately I didn’t want to be a small cog in a big wheel. So, instead, I joined a small consulting firm in the retail industry which I stayed in for two years. Your first job teaches you so much – the basics of buying a suit, building a routine. I loved the big city, but my heart strings kept pulling me back to sport.

I eventually took a precious week off work doing sports coaching in northern London and it made me realise how much sport meant to me. I don’t think I’d have got into Oxford without the confidence it had given me, and it ignited a real passion to see young girls from ethnic minorities playing sports. It was an obvious move to transition into the sports industry where I’ve been ever since.

I wasn’t born thinking I wanted to be an entrepreneur, but whenever I saw a problem, I wanted to fix it. So, when I saw sports sponsorship industry was inefficient, making a company that would fix it was the most obvious next step.

What is your definition of entrepreneurship?
Doing something new and doing it yourself. That’s the big difference. If the founders of AirBnb decided to start a second company they wouldn’t do it as entrepreneurs, they would be executives, hiring people to do the work for them. If you are successful then you don’t stay an entrepreneur forever – until then, you do everything yourself.

How and when did you know your idea was good enough to develop it?
Before starting OpenSponsorship, I did a lot of work in deal-making in the sports industry and was shocked at how inefficient it was. Whenever a process relies on a lot of cold calling you know something isn’t working! I knew OpenSponsorship would work when I realised it could be a real solution to a core problem.

What would you say are the top 3 skills that needed to be a successful entrepreneur? Why?
As an entrepreneur you need to be an implementer (the ability to actually put things into action), a problem solver, and be able to trust your gut and act when things feel ambiguous.

What is your favourite part of being an entrepreneur?
I think what I do now walks the fine line between being a CEO and an entrepreneur, but what I’ve always loved about entrepreneurship is that you get out what you put in. I’ve always believed that hard work should be rewarded. I love seeing immediate results, as well as the challenge of a steep learning curve. Ultimately though, it comes back to the genuine belief you have in the mission and why you started.

What individual, company or organization inspires you most? Why?
The people who amaze me are the ones who seek out things for the future, who think not only about our generation but ones three generations down the line. I’m particularly impressed by organisations that push a more socially conscious agenda despite it not being the essential goal of their company.

If you had 5 minutes with the above individual/ company/organization, what would you want to ask or discuss?
I’d love to discuss how you balance the desire to make a difference in the world with running a successful business. I’d also want to learn more about how you get the timing of things right, knowing when something is too soon, and how to avoid trying to do everything all at once.

What has been your most satisfying or successful moment in business?
It’s hard to pin-point one specific moment in an entrepreneurial journey. Something that meant a lot personally was when we raised money from a retired NBA All-Star. It was a real ‘land of opportunity’ moment – that I, as a girl who wasn’t born in America and had no network, could move here in 2013 and get in front of an All-Star player… just amazing! For the company, it would be the moments of realising how we are succeeding at something where many others have tried and failed. You always think you’re the first person to try something as an entrepreneur, but there will have been others who just haven’t got as far as you. Knowing that there are 7500 athletes who every morning log-in to OpenSponsorship because we help them keep doing what they love is definitely what makes me the proudest of us as a company.

What would you say have been some of your mistakes, failures or lessons learned as an entrepreneur?
As a first-time entrepreneur, there is so much unknown, and you make so many mistakes! You are constantly learning lessons – it’s why so many investors trust second-time founders. For instance, get distracted by big companies who aren’t as good for your long-term visions. There is almost a list of mistakes you will make at some point, but you also have to learn from them.

How have you funded your ideas?
Thankfully today you can set up a tech software group fairly cheaply. I did invest some personal money, and within 1 year of running the company we got into 500 startups, a technology accelerator. Since then we have gone on to raise over $5M from VCs and Angels.

Are there any sector-specific awards/grants/competitions that have helped you?
500 Startups in San Francisco were instrumental in getting us established.

If a new entrepreneur or startup came to you looking for entrepreneurship resources, where would you send them?
One of the best starting places are accelerators. A start-up accelerator is like an eight-week boot-camp, mainly for first time founders. It takes you through the 101 of how to fund a company with both general and industry specific advice, crucially helping to reduce the number of mistakes you will make. Similarly, find networks and groups early, knowing you can leave them as you progress whenever you want.

I’d also recommend ‘The Hard Thing About Hard Things’ by Ben Horowitz. It’s a book that talks about how the journey is always harder and longer than you expect, and how to be ready for it.

Have you faced any challenges as a woman entrepreneur? If so, how have you overcome them?
Definitely. In my first week on the job in India, when I was in a presentation with my white male boss, the Indian man giving the presentation deliberately faced his laptop 90 degrees away from me and wouldn’t properly engage with me until I mentioned I’d gone to Oxford. America is also difficult. In Britain we are used to female leaders while in the US it’s still up to debate as to whether a woman could be President. Depending on which country you end up in, it could be even harder!

I think it goes to show how women have to validate themselves way more, always proving why they deserve to be in a room. It’s easier for me as I can play the Oxford or Forbes card, but it is a challenge. Often men will invest in women if they are in traditionally female industries like beauty or fashion. It’s like they will allow a certain stereotype to prosper but not anything else. Life in male-dominated industries is more challenging.

What resources would you recommend for other women?
There are so many groups out there, like Ada’s List, a global community for women in tech. You will inevitably need support at different times and a variety of mentors that can speak to different issues. Build you support network because as an entrepreneur you don’t have colleagues, you have to do it yourself. Send out cold emails, say who you are, what you do and why you’re getting contact. The worst you can get is a ‘no’ – you have to be aggressive seeking out these contacts. Entrepreneurs who make it aren’t just lucky – they are the people who took more chances. Also, lean on your friendship group. As you all progress in different careers and likely different sectors you will want to talk about work. Find support in the people travelling alongside you, not just the ones who are ahead of you.

How could institutions such as the University of Oxford better support women entrepreneurs?
While I was at Oxford, we were never really taught about networking. I wish someone had sat me down and challenged me to meet people who were different from me. University is such a unique experience and you always wish you’d taken more advantage of it.

I also wish I’d been exposed to more industries – you can’t be an entrepreneur if you don’t know about different sectors and the problems in them. Industries are so much more diverse than people realise. For instance, the Paralympics are really the only time disabled people get significant media coverage despite being the largest minority in the world. Sports does that and yet no one thinks about that when you say the ‘sports industry.’ More exposure to that in University would be so helpful.

Do you have any advice specifically for other women who want to be entrepreneurs?
You have to make sure you’ve built enough credibility. Before you start your entrepreneurial journey, do everything you can to support yourself. Take a few years to work in a corporate company or bank. Build your network. It will pay off in the long run. When you’re building your start-up, you will want to lean on those younger years.

However, women do have a biological clock that men simply don’t, even with the financial pressures which fall on them. If you can squeeze things in earlier that’s good but finding a balance is a challenge.

Any last words of advice?
First, keep a diary of all the amazing people you meet that have made an impact on something you care about, small or big. Keep a record of your inspirations because so often you lost touch with them or forget those experiences.

Live life to the fullest. In my twenties I went to India and don’t really regret not doing things, but so many do. Don’t be fearful about things. Entrepreneurialism suits people who like change, who aren’t scared to mix things up and don’t need a routine.

Follow your passion when you’re young and can afford to get things wrong. Fail fast and get back on your path. Lastly, don’t just get caught up on the finish line. The end isn’t always the best part – enjoy the journey as well.