Episode 010: Jay Boolkin - Promise or Pay

We all make promises to ourselves, whether through making a New Year's resolution, or just setting a goal for ourselves to be healthier, lose weight, save money, travel to particular destinations, etc.  Often though, we fail to meet our goals, usually letting them fall by the wayside within a few weeks.  I recently recorded a podcast about goal setting which, in addition to the 6 steps to achieve your goals, includes the tip to share your goal with others to add incentive to achieving your goal.  Jay Boolkin, the founder of Promise or Pay, has come up with a novel way to incentivise your goal setting, through a donation to charity if you fail to meet your goal.

Promise or Pay is all about helping people make positive behavioural changes while creating a more engaging and empowering way for individuals to donate to charities.   According to Jay, "the likelihood of success increases by 33% if the goals is shared with others, and 72% if money is put on the line".

Listen here:

Jay has always been passionate about creating positive social change, studying humanitarian and social development courses at university.  He even put together a team of 6 volunteers together to start a small organisation called the Yolk Project, helping organisations around the world to incorporate social technologies into their external communication efforts.

After putting his education to good use working for NGOs and not-for-profits in Australia, USA and India, the idea for Promise or Pay came to him while he was working in Cambodia as a youth ambassador for development.

The desire to use technology to improve the lives of as many people as he can, rather than the on-to-one experience he was used to, has given Jay the drive to work on Promise or Pay full time.

Winning a competition through Social Startups (link here) allowed Jay to have a beta site built and begin the journey in earnest.  Not being a tech founder has presented challenges for Jay, but as he says, he "wouldn't change anything".

Since conceiving the idea for Promise or Pay, Jay has won, or been a finalist in a number of pitch competitions over the last two years, including:

  • Sydney SHINE Awards - Young Entrepreneur Finalist - 2015

  • General Assembly PitchFest Winner - 2015

  • Optus Digital Life PitchUp Winner - 2015

  • Macquarie Group Foundation Kickstarter Finalist - 2015

  • Deloitte Australia Social Innovation Pitch Competition Winner - 2014

  • The Guardian’s Activate Tech Talent Day Honourable Mention - 2014

  • Sydney Genesis Challenge Best Social or Not-for-profit Startup Finalist - 2014

  • Social Startups MVP Winner - 2014

Jay's biggest tip for startups is to enter as many competitions and pitch events as possible.  Not only do they give you an opportunity to fine tune your pitch, but the credibility that the awards give is enormous.  It's not always easy, especially for an introvert, however pushing yourself out of your comfort zone brings about many opportunities that you may normally miss.

There is a common saying that practice makes perfect, and this is certainly true for Jay, spending hours and hours perfecting and practising his pitch.  It is clearly obvious that the results speak for themselves.

Jay's biggest challenge has been being a sole founder, in taking all of the responsibility and having to own every failure.  Having a clear plan with action goals has been a great motivational tool to look back on and see the progress he has made.

With modest signups and donations made so far, Jay's big, hairy, obnoxious goal is to have helped 500,000 people achieve their goals within the next three years.  In order for Jay to reach this goal, he needs everyone to sign up and make a promise.


Competitions and Pitch Events

Take advantage of all competitions and pitch events.  Every event will give you an opportunity to practice and fine tune your pitch, and every successful win will add credibility to your startup.

Be Prepared

Practice, practice, practice.  Then practice some more.  When you think you've done enough practice, go and practice even more.

Be comfortable with being uncomfortable

Take on the challenges that you would normally avoid, because that's where opportunities lie.  Roadblocks will start to disappear as you become more confident.


If you have goals that you have set for yourself, jump on the Promise or Pay website and sign up to make a promise.  Then share with all of your friends so they can support you in your goal challenge.

You can follow Promise or Pay on Twitter and Facebook, and you can reach out to Jay via email.

Thanks for listening

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