Ep 084: Jack Ray

From police force to Founder, with Billing Better’s Jack Ray

Jack Ray shares his journey from police officer with the Metropolitan Police to entrepreneur by founding Billing Better.

Three key juicy bits from this week’s episode:

  • Finding a gap in the market by becoming more aware of your own surroundings
  • Turning an idea into a commercially viable business
  • Creating a system for managing your money as a business

In this episode we discuss:

  • 01:21                    Introduction to Jack Ray and Billing Better
    • Why Jack started his own business [02:23]
    • Identifying a gap in the market [04:21]

    06:50                    The first steps Jack took to build his business

    • Reaching the target market: students [07:48]
    • Billing Better’s financial strategy [9:10]

    11:58                    Billing Better’s competitors

    13:00                    Acquiring customers in the beginning

    15:16                    Getting support for the business

    18:17                    The importance of having a few key people to turn to for advice as a new entrepreneur

    19:27                    When Billing Better finally became profitable

    • Juggling a day job as a police officer with being a startup entrepreneur [20:34]

    21:24                    Hiring the first few employees and outsourcing

    29:42                    When Jack started to pay himself

    32:19                    Why Jack never sought investment for Billing Better

    • Billing Better’s current revenue [34:26]

    36:00                    Jack reflects on the freedom that entrepreneurship brings

    39:03                    Jack’s biggest failure and lessons learned from it

    41:35                    Billing Better’s system for managing money

    44:29                    Billing Better’s three core offerings

    46:44                    Jack’s parting advice for those looking to start a business

    47:44                    Jack’s vision for the future of Billing Better

Links Mentioned:


  • We just had to find a way of getting the word out to people. If we did that, the product would eventually sell.
  • The biggest failure I made in the beginning was not implementing a proper system for how we manage money.