Scaling Sustainably with Jon Brodsky: Lead to Succeed 42


In this episode, Naphtali interviews Jon Brodsky. Jon is’s Country Manager (US), leading the company’s growth across its core niche categories of international money transfers, personal loans, credit cards and shopping comparisons. Before that, he was the Senior Vice President Digital at Chicken Soup for the Soul, where he was responsible for product changes that helped grow monthly content reach from approximately 300,000 people to one billion people. Previous experience also includes time at, which Jon grew to 250,000 restaurants and nationwide coverage within 18 months, and, where he completed deals that generated over $300 million in annual revenue. 

Episode Notes:

  • 2:10 – Naphtali introduces Jon

  • 2:34 – Jon’s unorthodox pathway to leadership

  • 3:41 – How Jon’s competitive nature has served him

  • 4:37 – The benefits of asking the right questions to figure out how things work

  • 5:19 – Scaling reach (eyeballs on content) and revenue vs. SUSTAINABLE scalability

  • 5:47 – The difference between Uber and Airbnb and everyone else when it comes to scalability

  • 6:00 – Focus on the customer and their needs (what do they want and what are they not getting elsewhere?)

  • 6:41 – Why you should ask for money for a service, subscription or product

  • 7:45 – How do you know if there’s a demand for a product or service?

  • 8:18 – was really not such a novel idea

  • 9:21 – Why Jon mashes up new ideas with existing products and services (example:

  • 12:14 – How Jon sets goals (spoiler alert: not your normal goal setting process)

  • 13:00 – Using daily tracking to monitor progress

  • 14:05 – The only metrics Jon tracks

  • 14:30 – Why process trumps goals

  • 16:57 – Jon’s approach to delegation with internal training and letting his people fail (often and fast)

  • 18:32 – Using weekly coaching to support company managers

  • 19:05 – Startups cannot build companies by themselves

  • 20:35 – How Jon knows when to pull the plug on a failing situation

  • 21:55 – What terminated managers often tell Jon in exit interviews

  • 22:26 – The “Straight Up” honesty policy

  • 22:53 – Rapid fire

  • 23:51 – Connect with John via email, LinkedIn, and Twitter.

  • 24:24 – Stick with it and fight through the challenge

Connect with / follow Naphtali on Facebook, Twitter, LinkedIn, Instagram, Google Plus + YouTube

Get Naphtali’s book, “Becoming the New Boss: The New Leader's Guide to Sustained Success

Please subscribe to, rate and review the show. Your feedback gives social proof and encourages more folks to listen.



Google Play

Please share this recording with your networks and tag me as well.

Contact me at to schedule a free, no obligation executive/leadership coaching session.