Jack Dorseys Last Boss

Tony Stubblebine The Top Podcast Episode191

In Episode #191, Nathan speaks with Tony Stubblebine, the CEO and co-founder at Coach.me. Listen as Nathan and Tony talk about different branches of coaching and the latter’s claim to fame as Jack Dorsey’s last boss.

Famous 5

  • Favorite Book? – The Hard Thing About Hard Things
  • What CEO do you follow?— Evan Williams
  • What is your favorite online tool?— Evernote
  • Do you get 8 hours of sleep?— Sometimes
  • If you could let your 20 year old self know one thing, what would it be?— Have faith in yourself to work on a life mission instead of thinking about salary and location of a job.

Tony Stubblebine co-founded Coach.Me (formerly knows as Lift) on the idea that positive reinforcement and community support could be deployed universally to help people achieve their goals. Prior to Coach.Me, he was the founder and CEO of CrowdVine Event Social Networks, which builds simple and powerful social software to help people connect and meet. He was part of the Wesabe launch team, Director of Engineering at Odeo.com and Engineering Lead for O’Reilly Media. He is the author of Regular Expression Pocket Reference (O’Reilly).

Time Stamped Show Notes:

  • 01:00 – Nathan’s introduction to today’s show
  • 01:54 – Tony joins the show.
  • 02:27 – Tony refused to be interviewed for the book Hatching Twitter so that he could write his own book one day. His claim to fame is ‘the last boss of Jack Dorsey.’
  • 05:01 – Tony talks about Coach.me which hit 1 million users.
  • 07:16 – Mechanically Coach.me was a success because it was successful in revenue, conversion, and results from the service.
  • 09:10 – Coach.me takes a 50% cut of coaching fees as a revenue source.
  • 10:03 – Digital coaching is when the coaching happens on a messaging based relationship. Coaches can pay a smaller cut to use the tools from Coach.me.
  • 11:18 – In 2014, they grossed 82K$, 2015 they grossed 650K$. They project 2 million dollars in 2016.
  • 12:22 – There are roughly 5K coaches in the database, of which there are varying degrees of commitment by the coaches.
  • 13:49 – Rolling notes can be open or closed based on a business’s scaling.
  • 14:34 – Tony talks about LTV (lifetime value) and how his business interacts with the metric.
  • 16:12 – Many people tend to hire more than one coach. Unlike other branches of coaching, Coach.me has enough information to know what’s working and what isn’t.
  • 16:47 – Jack Dorsey was a good employee while he worked under Tony.
  • 17:42 – Host Gator: Powerful web hosting made easy and affordable
  • 18:20 – Famous Five

3 Key Points:

  1. Digital coaching is a branch of coaching when the client maintains constant communication through digital media.
  2. Rolling notes is a way of raising funds that can be open or closed depending on business scalability. Burned money is cash that is leaving the bank account while running a business.
  3. Many people tend to hire more than one coach. Unlike other branches of coaching, Coach.me has enough information to know what’s working and what isn’t.

Resources Mentioned:

  • Edgar – Nathan uses Edgar instead of other scheduling tools for Twitter because Edgar cycles through content over and over (buffer/others you have to re-input content over and over – time consuming). In the last several months, Edgar has driven Nathan over 3728 clicks that he didn’t have to work or pay for.
  • Host Gator – Powerful web hosting made easy and affordable
  • me – Tony’s business
  • LinkedIn – Tony’s LinkedIn
  • The Hard Thing About Hard Things – Tony’s favorite business book
  • Evan Williams – CEO Tony follows
  • Evernote – Tony’s favorite online tool


Show Notes provided by Mallard Creatives