Welcome to the Tough Cookies series where we interview and celebrate the strong and determined individuals who are making waves in the tech industry.

This week we are speaking with Chris, founder and CEO of Box 2 Media and The Pitch.

Starting his career as a journalist and editor with a primary focus on small businesses and startups, Chris went on to found Box 2 Media with the flagship brand The Pitch. He is known for his involvement and support for startups, whether that’s through mentoring or taking companies through a pitching boot camp across the country.

A pioneer and cheerleader for small businesses, we couldn’t wait to ask a few questions…

So tell me a bit about Box 2 Media and The Pitch – what do these brands do and how did they come about?

Box 2 Media is a B2B content agency that specialises in creating content aimed at small business owners. We work with partners like Microsoft, Crowdcube and Greenwich University to help them build their audiences.

We’ve been lucky enough to interview hundreds of entrepreneurs and we’re a small business ourselves, so we know the challenges inside out. Having that background means we can create content that inspires action – it’s not just about driving traffic.

We also run a startup competition called The Pitch. We’ve had everyone from the founders of startups like EatFirst and Resolver to Fitness First and Starling Bank take part.

You started your career as a journalist and editor writing about startups – what brought about this interest?

I’ve always been fascinated by business and economics. I started writing about large, listed companies about a decade ago. It got frustrating because it became a game of access. The stories were handed out, everyone was really careful about what they say.

Small businesses employ the vast majority of people but were largely ignored at the time. The opportunity was to be able to share the human side of starting and running a business. The grit and determination and the beauty of the struggle before the corporate mindset takes hold.

You are also a mentor for the Princes Trust! What are the biggest struggles your mentees have?

There’s a lot of nuts and bolts stuff about starting a business, primarily sales, finance and marketing.

The biggest thing with young founders is self-belief. Backing themselves to start turning an idea they love into a business. Money’s a big factor. They often won’t charge what they’re worth or be afraid to ask for money at all.

I think most founders struggle with self-doubt at times, it’s something I’ve spoken to my mentor about.

What makes a good mentor?

Be honest and open and not too prescriptive – it’s about helping them find answers.

There are broad pieces of advice that are useful but very quickly you’re going to have to be able to relate to what people are going through. That normally means you’ve been through it in the last two to five years.

If you run a business, you should always be mentoring people that are a stage or two behind you and getting help from people that are at the next stage.

What are your top tips for entrepreneurs to find a mentor?

It doesn’t need to be someone that’s far ahead in business or well known. They are difficult to reach and have probably forgotten what the nitty-gritty you need to talk about is like.

Look for someone that is a stage or two ahead of you, likely with a similar type of business. Keep them updated on how you implement their advice. Respect their diaries. Know that the advice you need will evolve as your business does, so there’s no set length for these relationships.

Finally, always go in offering some value if you can and start with a small ask.

What has been your career highlight?

I broke a story about national minimum wage abuse that snowballed into legislative change. Niche, but it’s nice to make a difference on the business pages.

It was lovely to see my grandma’s copy of Recruiter, the first publication I wrote for full-time, on her tea trolley, so she could show people when they came over.

And what has been the lowest point in your career and how did you overcome it?

There’s nothing that’s been truly horrible. Running a business does push you through a series of highs and lows. The most difficult period was probably my business partner leaving the company but it worked out in the end.

Finally, what is your favourite flavoured cookie?

Double chocolate chip. Take the best thing and double down.