12 Deepak Tailor BODY 1aDeepak Tailor is founder of LatestFreeStuff.co.uk, a website that makes it’s money (and make a lot of money) by giving stuff away, for free!

He won the coveted Great British Young Entrepreneur of the Year 2015, he has written and published a best selling book on Amazon book and recently appeared on popular BBC TV show Dragons Den, pitching his business to some of the most powerful business leaders in the world such as Peter Jones and Deborah Meaden.

We speak deeply about:

  • How Deepak started his first businesses with no other intention than to generate beer money whilst at Uni, and then to fund a trip around the world – and how that has led to him running a highly profitable internet business. Deepak is very open about sharing his revenue and profit figures with us, so that’s really interesting
  • How to scale a startup within a co-working space
  • Why writing a book is such a powerful and under-utilised form of marketing
  • Why Deepak walked away from a significant investment from a very famous entrepreneur

This interview is a little different to the ones you would have heard to date. Why? Because this was actually recorded at the very end of last year, and was one of the very first Rebelhead interviews we ever recorded. It was so early that we didn’t even have a name for the Rebel Wrap Up round (as you will hear), and I was very rough around the edges in terms of interview style!

12 Deepak Tailor BODY 3

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  • I wanted to dominate not just the SIM cards industry, but everything to do with free stuff
  • I’m always the quietest person in the meeting room, because I’m always thinking  
  • I’m such a big advocate of co-working space to grow a company
  • Don’t just go and live your 9-5 job, start something
  • Over the last couple of years I’ve tried to create boundaries between work and home life
  • You have to take that step from becoming a bedroom entrepreneur, to having something tangible, and taking it to the next level
  • Be more controversial and disruptive
  • I would say go fully at it, rip everything apart that you’ve learnt, an
  • Find the gaps in the industry you’re going in to and do things differently
  • There’s always inefficiencies in every single industry, and you just need to find those gaps
  • I had to make a change, I had to be disruptive in this industry
  • Lose the fear, because that’s the only thing that held me back
  • Go and take small steps and actually go and do it
  • Pushing people to actually take that motivation is the hardest thing12 Deepak Tailor BODY 2
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Time Stamped Notes

00:03:30 – Overview of Deepak’s business Latest Free Stuff
00:09:06 –  Selling spy cameras online (spotting the supplier list while working in Harrods and seeing the HUGE margins)
00:13:01 – Funding his travelling by working a few hours a day on his own sites
00:14:04 – On starting the UK’s biggest comparison website for SIM cards
00:15:34 – On how Deepak started LatestFreeStuff
00:17:42 – How do you make money giving stuff away for free?!
00:23:12 – Dealing with uncertainty and protecting the downside
00:24:19 – On employing his first member of staff
00:26:44 – On the money that LatestFreeStuff makes
00:28:21 – Going on Dragons Den
00:47:07 – On the power of a co-working space for StartUps
00:50:20 – Why Deepak runs monthly Meet Ups
00:53:28 – On Winning ‘The Young British Entrepreneur of the Year 2015’
00:55:32 – On why and how Deepak wrote an Amazon best selling book as a marketing tactic
00:59:19 – Work hours and the lifestyle of an entrepreneur
01:03:20 – Single most important decision that has contributed to Deepak’s success
01:07:34 – The best advice Deepak ever received

The Rebel Wrap Up Round

If you could go back to any point in your life, and have 1 hour with your past self; what moment would it be and what would you tell yourself?

01:04:06 I would go back to when I was 16 years old, and tell myself to start a business now. Don’t wait. Don’t waist time. Just get started now.

What advice would you give to anyone listening to this who wants to become a creator entrepreneur?

01:06:03 Just go for it!

What is the best piece of advice you have ever received, who gave it to you and how has it positively affected your career?

01:07:35 When I was scared to launch my first ever website because I was worried it wasn’t perfect enough, someone said to me – just go and do it. It removed the fear, and from now on my advice to anyone is ‘just go and do it’.

What is the one generally agreed upon rule or conventional piece of wisdom, that you disagree with?

01:09:05 Market research. Because people will test and test and test without ever doing anything!

What’s your definition of entrepreneurship?

01:13:51 Building a product where it didn’t exist before and creating wealth.

Who is the most disruptive, rebellious or revolutionary entrepreneur of the last 2 years?

01:14:31 The founders of Tinder. Because it’s owned by Match.com and they disrupted their own industry

Who do you nominate to be a guest on the RebelHead Entrepreneurs podcast?

01:15:49 Chris Holbrook. Free Post Code Lottery.

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About The Author

Max Pepe

Max spent the first 8 years of his career in music, touring and recording with two UK / US rock bands. With a passion for marketing, Max launched a digital marketing agency in 2012. In three years grew a team from 2 people to 30, driving 800% growth year on year. Max now believes there is a massive disconnect between the world of business and the world of creativity. To address this problem, REBELHEAD was born. Max speaks regularly around the world about marketing and entrepreneurship. In 2016 gave a TEDxTalk titled 'Challenge the Concept That You're Either an Artist or a Business Person'. Aside from Rebelhead, Max is VP Marketing for award winning mobile tech company, Mozoo - and consults on marketing and growth for scale ups.

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