Ep 12: You can’t fail if you never give up – with Jay Winder

Jay WinderYou can’t possibly fail if you never give up! That’s the big lesson I’ve learned from my interview with Jay Winder. Being persistent is a quality that most successful entrepreneurs have. In most success stories, entrepreneurs first go through dark times. And it’s usually before success that they find themselves at the lowest point. What set successful entrepreneurs apart is their ability to never give up, and keep showing up no matter how hard it is.

Jay is the founder CEO of MakeLeaps, a company that has revolutionized the way businesses manage their invoices. Japan is a country where, very often, working hard and working well are mistaken with one another. Jay had realized that many companies were spending countless hours managing their invoices, getting themselves busy with lots of manual work. Now thanks to MakeLeaps, what used to take several people, several hours a week can now be done online in just a few clicks in no more than 15 minutes. Today, the company has grown as the leading invoicing management system in Japan with over 18,000 customers (as of Mar. 2015.)

Jay shares with us his story, including his first struggles when starting MakeLeaps. One big lesson for him was to learn how to scale down and focus. Indeed, many first time entrepreneurs fail because they want to do too much, although when you manage a product, your success depends on your ability to say no to 99% of things you want to do.

We also discuss about the importance of getting yourself into difficult (if not embarrassing) situations. “A person’s success in life can usually be measured by the number of uncomfortable conversations he or she is willing to have.” says Tim Ferriss. Being an entrepreneur is about constantly selling your idea and product. Along the way, you’ll probably get a lot of rejections and people saying NO to you. That’s something you should get yourself used to says Jay. You should get out there and become an expert at asking for money!

Another great conversation with many pieces of advice for entrepreneurs.

Question: Keeping on or quitting, how can you know the right thing to do? (reply in the comments)

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Show notes

  • (01:54) Introduction of Jay Winder
  • (04:12) Presentation of MakeLeaps
  • (09:44) Getting busy is not working
  • (12:08) Where to invest your time, money and actions
  • (18:54) Making products vs providing services
  • (25:50) Finding a massive problem to solve
  • (29:34) Scoping down and importance of validation
  • (35:16) Learning how to sell and ask for money
  • (37:30) Main struggles
  • (40:32) 3 simple pieces of advice for any entrepreneur
  • (46:09) Hacker News meetups
  • (49:46) Quick-fire questions

Thanks for listening!

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