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Mar 6, 2016 · 22m · top-founders

Jack Dorsey's Last Boss Tells True Story in Episode 191 with Tony Stubblebine

Tony Stubblebine · 13m spoken Nathan Latka · 6m spoken
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In this episode of The Top, host Nathan Latka interviews entrepreneur Tony Stubblebine, who recounts his early experiences managing Jack Dorsey at Odeo and explains how he pivoted and scaled Coach.me into a multi-million-dollar coaching marketplace.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Nathan holds 34.5% of the talking time here. How this is scored →

Nathan as informed peer 3.2 Guest teaching 3.0 Guest disagreement 1.0 Nathan pushing back 1.8
05100:0010:0020:001:38–4:55 · Nathan as informed peer 3/10 Tony Stubblebine on Odeo and Twitter's True Origin Tony shares insider history regarding Odeo, Jack Dorsey, and the inaccuracies of early media accounts of Twitter's founding. Nathan acts primarily as an engaged interviewer, interjecting briefly to defend podcasting's resurgence.4:56–10:52 · Nathan as informed peer 4/10 Transitioning from Lift to Coach.me Digital Marketplace Tony details the pivot from Lift to Coach.me and explaining the digital coaching mechanics. Nathan interrupts Tony's monologue to keep the pacing brisk and direct the focus onto marketplace revenue splits.10:52–16:40 · Nathan as informed peer 6/10 Coach.me Financial Growth, Fundraising, and Improving Lifetime Value Nathan demonstrates high fluency in SaaS and fundraising metrics, breaking down net burn and rolling convertible notes for the audience. Tony candidly shares gross revenue, burn numbers, and LTV increases.16:41–21:40 · Nathan as informed peer 3/10 Reflections on Managing Jack Dorsey at Odeo After briefly discussing Jack Dorsey's work ethic at Odeo and a sponsor break, Nathan runs through his rapid-fire Famous Five format. Tony provides thoughtful, reflective responses about his habits and career philosophy.21:43–22:40 · Nathan as informed peer 0/10 Episode Conclusion, Personal Announcements, and Next Episode Teaser Nathan delivers a solo outro recapping the episode, promoting his upcoming webinar, and previewing the next guest.1:38–4:55 · Guest teaching 5/10 Tony Stubblebine on Odeo and Twitter's True Origin Tony shares insider history regarding Odeo, Jack Dorsey, and the inaccuracies of early media accounts of Twitter's founding. Nathan acts primarily as an engaged interviewer, interjecting briefly to defend podcasting's resurgence.4:56–10:52 · Guest teaching 4/10 Transitioning from Lift to Coach.me Digital Marketplace Tony details the pivot from Lift to Coach.me and explaining the digital coaching mechanics. Nathan interrupts Tony's monologue to keep the pacing brisk and direct the focus onto marketplace revenue splits.10:52–16:40 · Guest teaching 4/10 Coach.me Financial Growth, Fundraising, and Improving Lifetime Value Nathan demonstrates high fluency in SaaS and fundraising metrics, breaking down net burn and rolling convertible notes for the audience. Tony candidly shares gross revenue, burn numbers, and LTV increases.16:41–21:40 · Guest teaching 2/10 Reflections on Managing Jack Dorsey at Odeo After briefly discussing Jack Dorsey's work ethic at Odeo and a sponsor break, Nathan runs through his rapid-fire Famous Five format. Tony provides thoughtful, reflective responses about his habits and career philosophy.21:43–22:40 · Guest teaching 0/10 Episode Conclusion, Personal Announcements, and Next Episode Teaser Nathan delivers a solo outro recapping the episode, promoting his upcoming webinar, and previewing the next guest.1:38–4:55 · Guest disagreement 2/10 Tony Stubblebine on Odeo and Twitter's True Origin Tony shares insider history regarding Odeo, Jack Dorsey, and the inaccuracies of early media accounts of Twitter's founding. Nathan acts primarily as an engaged interviewer, interjecting briefly to defend podcasting's resurgence.4:56–10:52 · Guest disagreement 1/10 Transitioning from Lift to Coach.me Digital Marketplace Tony details the pivot from Lift to Coach.me and explaining the digital coaching mechanics. Nathan interrupts Tony's monologue to keep the pacing brisk and direct the focus onto marketplace revenue splits.10:52–16:40 · Guest disagreement 1/10 Coach.me Financial Growth, Fundraising, and Improving Lifetime Value Nathan demonstrates high fluency in SaaS and fundraising metrics, breaking down net burn and rolling convertible notes for the audience. Tony candidly shares gross revenue, burn numbers, and LTV increases.16:41–21:40 · Guest disagreement 1/10 Reflections on Managing Jack Dorsey at Odeo After briefly discussing Jack Dorsey's work ethic at Odeo and a sponsor break, Nathan runs through his rapid-fire Famous Five format. Tony provides thoughtful, reflective responses about his habits and career philosophy.21:43–22:40 · Guest disagreement 0/10 Episode Conclusion, Personal Announcements, and Next Episode Teaser Nathan delivers a solo outro recapping the episode, promoting his upcoming webinar, and previewing the next guest.1:38–4:55 · Nathan pushing back 2/10 Tony Stubblebine on Odeo and Twitter's True Origin Tony shares insider history regarding Odeo, Jack Dorsey, and the inaccuracies of early media accounts of Twitter's founding. Nathan acts primarily as an engaged interviewer, interjecting briefly to defend podcasting's resurgence.4:56–10:52 · Nathan pushing back 3/10 Transitioning from Lift to Coach.me Digital Marketplace Tony details the pivot from Lift to Coach.me and explaining the digital coaching mechanics. Nathan interrupts Tony's monologue to keep the pacing brisk and direct the focus onto marketplace revenue splits.10:52–16:40 · Nathan pushing back 3/10 Coach.me Financial Growth, Fundraising, and Improving Lifetime Value Nathan demonstrates high fluency in SaaS and fundraising metrics, breaking down net burn and rolling convertible notes for the audience. Tony candidly shares gross revenue, burn numbers, and LTV increases.16:41–21:40 · Nathan pushing back 1/10 Reflections on Managing Jack Dorsey at Odeo After briefly discussing Jack Dorsey's work ethic at Odeo and a sponsor break, Nathan runs through his rapid-fire Famous Five format. Tony provides thoughtful, reflective responses about his habits and career philosophy.21:43–22:40 · Nathan pushing back 0/10 Episode Conclusion, Personal Announcements, and Next Episode Teaser Nathan delivers a solo outro recapping the episode, promoting his upcoming webinar, and previewing the next guest.

speaking balance: gold is Nathan, purple is the guest (3 minute bins)

0:00 · Nathan 73.2% · guest 26.8%0:00 · Nathan 73.2% · guest 26.8%3:00 · Nathan 12.9% · guest 87.1%3:00 · Nathan 12.9% · guest 87.1%6:00 · Nathan 3.3% · guest 96.7%6:00 · Nathan 3.3% · guest 96.7%9:00 · Nathan 33.1% · guest 66.9%9:00 · Nathan 33.1% · guest 66.9%12:00 · Nathan 27.4% · guest 72.6%12:00 · Nathan 27.4% · guest 72.6%15:00 · Nathan 41.1% · guest 58.9%15:00 · Nathan 41.1% · guest 58.9%18:00 · Nathan 26.9% · guest 73.1%18:00 · Nathan 26.9% · guest 73.1%21:00 · Nathan 75.2% · guest 24.8%21:00 · Nathan 75.2% · guest 24.8%
Sharpest disagreement ▶ 2:26 Dismissing media depictions of Twitter's origin

Tony bluntly dismisses the famous New Yorker article about Twitter as complete falsehood and claims only he knows what actually occurred at Odeo.

 Hardest push from Nathan ▶ 8:58 Cutting off guest to focus on unit economics

Nathan directly cuts Tony off mid-sentence to force the conversation onto the core mechanics of how Coach.me makes money.

 Biggest teaching moment ▶ 15:11 Breaking down unit economics and LTV progression

Tony educates Nathan on Coach.me's evolution from simple habit-tracking with low lifetime value to high-retention multi-coach digital messaging.

 Nathan holds their own ▶ 13:40 Nathan explains rolling notes and supply-demand leverage

Nathan jumps in to define rolling convertible notes and explains the tactical advantages founders gain by leveraging them against strategic investors.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Tony Stubblebine on Odeo and Twitter's True Origin 3522 Tony shares insider history regarding Odeo, Jack Dorsey, and the inaccuracies of early media accounts of Twitter's founding. Nathan acts primarily as an engaged interviewer, interjecting briefly to defend podcasting's resurgence.
Transitioning from Lift to Coach.me Digital Marketplace 4413 Tony details the pivot from Lift to Coach.me and explaining the digital coaching mechanics. Nathan interrupts Tony's monologue to keep the pacing brisk and direct the focus onto marketplace revenue splits.
Coach.me Financial Growth, Fundraising, and Improving Lifetime Value 6413 Nathan demonstrates high fluency in SaaS and fundraising metrics, breaking down net burn and rolling convertible notes for the audience. Tony candidly shares gross revenue, burn numbers, and LTV increases.
Reflections on Managing Jack Dorsey at Odeo 3211 After briefly discussing Jack Dorsey's work ethic at Odeo and a sponsor break, Nathan runs through his rapid-fire Famous Five format. Tony provides thoughtful, reflective responses about his habits and career philosophy.
Episode Conclusion, Personal Announcements, and Next Episode Teaser 0000 Nathan delivers a solo outro recapping the episode, promoting his upcoming webinar, and previewing the next guest.

Statements from this episode (11)

Assertion Not checkable as stated
Stubblebine refused Hatching Twitter interviews to write his own book
“You know, for the book Hatching Twitter, I'm the only person at Odeo who refused to be interviewed for that book, and basically I did it so that I could write my own book one day.”
Tony Stubblebine Mar 6, 2016 ▶ 2:26
Opinion
Stubblebine: Hatching Twitter has minor factual errors but feels broadly true
“The book itself is basically true. The story rang true. A lot, all, almost all of the facts that I knew about were wrong in some minor way as I read the book, but the actual story of it felt true.”
Tony Stubblebine Mar 6, 2016 ▶ 3:06
Opinion
Stubblebine: Twitter's early turnover was team upgrading, not co-founder feuds
“It wasn't that the co-founders were feuding at the, or that there was any sort of scandal. It was just, they're constantly trying to upgrade the team in order to keep up with what Twitter ended up being, which, you know, obviously had nothing to do with where …”
Tony Stubblebine Mar 6, 2016 ▶ 3:32
Insight
Consumer eyeball startups now require 50 to 100 million active users
“The standards for an eyeball business, when I started working in startups in 2005 was our rule of thumb is if you got 300,000 users, you are guaranteed at least a major acquisition. And now if you can't get 50 or a hundred million users, you're not really anyt…”
Tony Stubblebine Mar 6, 2016 ▶ 5:20
Assertion Not checkable as stated
Stubblebine: Coach.me hit a 5% freemium conversion rate in early testing
“We were running the free side of the challenge and the paid side. And our conversion rate was like five percent. So, you know, like in freemium conversion, like you're lucky if you get to three percent.”
Tony Stubblebine Mar 6, 2016 ▶ 7:49
Disclosure
Coach.me takes 50% on marketplace leads and 10% to 30% on coach-sourced clients
“We take a cut of the coaching. All the coaching happens through our online tools, and we take, if we bring the client, we bring a ton of the clients, we take 50%, and then if they if they bring the client, they take somewhere between 70 and 90%.”
Tony Stubblebine Mar 6, 2016 ▶ 9:08
Prediction Not checkable as stated
Coach.me grew from $82k in 2014 to a projected $2M in 2016
“And so in in 2014, we are, we grossed 82,000 dollars. In 2014. And in 2015 we gross 650,000 dollars, and in 2016 we think we'll gross two million dollars.”
Tony Stubblebine Mar 6, 2016 ▶ 11:13
Assertion Not checkable as stated
Stubblebine: Coach.me Pays 150 Coaches Monthly
“What I would say is we pay out to a 150 per month and we probably have 10 or 20 that take it really seriously.”
Tony Stubblebine Mar 6, 2016 ▶ 12:05
Assertion Not checkable as stated
Stubblebine: Coach.me Net Burn Is $20K Per Month
“It's like. 20,000 dollars a month.”
Tony Stubblebine Mar 6, 2016 ▶ 13:07
Assertion Not checkable as stated
Stubblebine: Coach.me Doubled User LTV From $42 to $90
“And so our original LTVs were like 42 dollars per user. I really remember that number per year. Per year. And so I was like, shit, this is not like, we got to get this quality up. And we started digging into it. We did this round of, oh, well, there's a bunch …”
Tony Stubblebine Mar 6, 2016 ▶ 15:39
Opinion
Stubblebine: Jack Dorsey was the only reliable employee at Odeo
“The you know, the whole team was really chaotic, and I mostly spent time dealing with other people's problems, and Jack was the only reliable person.”
Tony Stubblebine Mar 6, 2016 ▶ 16:55
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