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Jun 23, 2017 · 28m · top-founders

699: The Fired ConvertKit Co-Founder You've Never Heard Of, Father Made Me Feel "Not Worth Enough"

Dan Gamito · 13m spoken Nathan Latka · 11m spoken
0:00 / 0:00

gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions

In this episode of The Top, host Nathan Latka interviews ManyChat's Dan Gamito about Messenger marketing automation, the hard-learned equity lessons from his controversial exit at ConvertKit, and his personal journey overcoming imposter syndrome and self-worth challenges.

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 46.8% of the talking time here. How this is scored →

Nathan as informed peer 4.3 Guest teaching 2.2 Guest disagreement 0.7 Nathan pushing back 3.2
05100:0010:0020:001:06–5:17 · Nathan as informed peer 4/10 ManyChat Strategy and Conversational Bot Optimization Nathan relates his personal struggles configuring ManyChat sequences and asks whether to mimic human chat. Dan corrects his premise by clarifying that Messenger bots should not be treated like email autoresponders but as conversational bottom-of-funnel touchpoints.5:17–10:01 · Nathan as informed peer 5/10 ManyChat Metrics, Pricing, and Origins Nathan drills Dan on user metrics, pricing tiers, and funding history, applying 80/20 rules to estimate user distribution. Dan shares the history of pivoting from Telegram and metrics around lead subscriber valuation.10:01–16:05 · Nathan as informed peer 6/10 Dan's Role and Controversial Exit from ConvertKit Nathan probes deeply into Dan's departure from ConvertKit, pushing him to clarify whether he was fired. Nathan brings up ConvertKit's churn rate and standard startup 1-year cliff equity mechanics to expose how Dan was terminated weeks before vesting.16:06–19:13 · Nathan as informed peer 2/10 Childhood Origins of Imposter Syndrome and Self-Worth Nathan asks a piercing personal question regarding why Dan undervalued himself. Dan opens up in a vulnerable monologue about his relationship with his father and the roots of his imposter syndrome.19:14–22:42 · Nathan as informed peer 7/10 Negotiating Leverage at ManyChat and Setting Boundaries When Dan admits he has been at ManyChat for six months without finalizing equity, Nathan takes charge and provides a detailed tactical playbook on how early employees should time-box trial periods to negotiate compensation from a position of leverage.22:42–26:31 · Nathan as informed peer 2/10 Sponsor Segment: Acuity Scheduling Nathan delivers a sponsor spot for Acuity Scheduling before conducting the standard Famous Five lightning round, maintaining a light and collaborative tone.1:06–5:17 · Guest teaching 5/10 ManyChat Strategy and Conversational Bot Optimization Nathan relates his personal struggles configuring ManyChat sequences and asks whether to mimic human chat. Dan corrects his premise by clarifying that Messenger bots should not be treated like email autoresponders but as conversational bottom-of-funnel touchpoints.5:17–10:01 · Guest teaching 3/10 ManyChat Metrics, Pricing, and Origins Nathan drills Dan on user metrics, pricing tiers, and funding history, applying 80/20 rules to estimate user distribution. Dan shares the history of pivoting from Telegram and metrics around lead subscriber valuation.10:01–16:05 · Guest teaching 2/10 Dan's Role and Controversial Exit from ConvertKit Nathan probes deeply into Dan's departure from ConvertKit, pushing him to clarify whether he was fired. Nathan brings up ConvertKit's churn rate and standard startup 1-year cliff equity mechanics to expose how Dan was terminated weeks before vesting.16:06–19:13 · Guest teaching 1/10 Childhood Origins of Imposter Syndrome and Self-Worth Nathan asks a piercing personal question regarding why Dan undervalued himself. Dan opens up in a vulnerable monologue about his relationship with his father and the roots of his imposter syndrome.19:14–22:42 · Guest teaching 1/10 Negotiating Leverage at ManyChat and Setting Boundaries When Dan admits he has been at ManyChat for six months without finalizing equity, Nathan takes charge and provides a detailed tactical playbook on how early employees should time-box trial periods to negotiate compensation from a position of leverage.22:42–26:31 · Guest teaching 1/10 Sponsor Segment: Acuity Scheduling Nathan delivers a sponsor spot for Acuity Scheduling before conducting the standard Famous Five lightning round, maintaining a light and collaborative tone.1:06–5:17 · Guest disagreement 1/10 ManyChat Strategy and Conversational Bot Optimization Nathan relates his personal struggles configuring ManyChat sequences and asks whether to mimic human chat. Dan corrects his premise by clarifying that Messenger bots should not be treated like email autoresponders but as conversational bottom-of-funnel touchpoints.5:17–10:01 · Guest disagreement 1/10 ManyChat Metrics, Pricing, and Origins Nathan drills Dan on user metrics, pricing tiers, and funding history, applying 80/20 rules to estimate user distribution. Dan shares the history of pivoting from Telegram and metrics around lead subscriber valuation.10:01–16:05 · Guest disagreement 1/10 Dan's Role and Controversial Exit from ConvertKit Nathan probes deeply into Dan's departure from ConvertKit, pushing him to clarify whether he was fired. Nathan brings up ConvertKit's churn rate and standard startup 1-year cliff equity mechanics to expose how Dan was terminated weeks before vesting.16:06–19:13 · Guest disagreement 0/10 Childhood Origins of Imposter Syndrome and Self-Worth Nathan asks a piercing personal question regarding why Dan undervalued himself. Dan opens up in a vulnerable monologue about his relationship with his father and the roots of his imposter syndrome.19:14–22:42 · Guest disagreement 1/10 Negotiating Leverage at ManyChat and Setting Boundaries When Dan admits he has been at ManyChat for six months without finalizing equity, Nathan takes charge and provides a detailed tactical playbook on how early employees should time-box trial periods to negotiate compensation from a position of leverage.22:42–26:31 · Guest disagreement 0/10 Sponsor Segment: Acuity Scheduling Nathan delivers a sponsor spot for Acuity Scheduling before conducting the standard Famous Five lightning round, maintaining a light and collaborative tone.1:06–5:17 · Nathan pushing back 2/10 ManyChat Strategy and Conversational Bot Optimization Nathan relates his personal struggles configuring ManyChat sequences and asks whether to mimic human chat. Dan corrects his premise by clarifying that Messenger bots should not be treated like email autoresponders but as conversational bottom-of-funnel touchpoints.5:17–10:01 · Nathan pushing back 3/10 ManyChat Metrics, Pricing, and Origins Nathan drills Dan on user metrics, pricing tiers, and funding history, applying 80/20 rules to estimate user distribution. Dan shares the history of pivoting from Telegram and metrics around lead subscriber valuation.10:01–16:05 · Nathan pushing back 6/10 Dan's Role and Controversial Exit from ConvertKit Nathan probes deeply into Dan's departure from ConvertKit, pushing him to clarify whether he was fired. Nathan brings up ConvertKit's churn rate and standard startup 1-year cliff equity mechanics to expose how Dan was terminated weeks before vesting.16:06–19:13 · Nathan pushing back 3/10 Childhood Origins of Imposter Syndrome and Self-Worth Nathan asks a piercing personal question regarding why Dan undervalued himself. Dan opens up in a vulnerable monologue about his relationship with his father and the roots of his imposter syndrome.19:14–22:42 · Nathan pushing back 4/10 Negotiating Leverage at ManyChat and Setting Boundaries When Dan admits he has been at ManyChat for six months without finalizing equity, Nathan takes charge and provides a detailed tactical playbook on how early employees should time-box trial periods to negotiate compensation from a position of leverage.22:42–26:31 · Nathan pushing back 1/10 Sponsor Segment: Acuity Scheduling Nathan delivers a sponsor spot for Acuity Scheduling before conducting the standard Famous Five lightning round, maintaining a light and collaborative tone.

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

0:00 · Nathan 60.7% · guest 39.3%0:00 · Nathan 60.7% · guest 39.3%3:00 · Nathan 55.2% · guest 44.8%3:00 · Nathan 55.2% · guest 44.8%6:00 · Nathan 25.8% · guest 74.2%6:00 · Nathan 25.8% · guest 74.2%9:00 · Nathan 47.2% · guest 52.8%9:00 · Nathan 47.2% · guest 52.8%12:00 · Nathan 29.7% · guest 70.3%12:00 · Nathan 29.7% · guest 70.3%15:00 · Nathan 28.2% · guest 71.8%15:00 · Nathan 28.2% · guest 71.8%18:00 · Nathan 15.3% · guest 84.7%18:00 · Nathan 15.3% · guest 84.7%21:00 · Nathan 96.2% · guest 3.8%21:00 · Nathan 96.2% · guest 3.8%24:00 · Nathan 35.2% · guest 64.8%24:00 · Nathan 35.2% · guest 64.8%27:00 · Nathan 98.8% · guest 1.2%27:00 · Nathan 98.8% · guest 1.2%
Sharpest disagreement ▶ 2:46 Messenger vs Email Reframe

Dan firmly dismisses the premise of treating Messenger bots like email autoresponders, stating that what works in email simply fails in conversational chat.

 Hardest push from Nathan ▶ 15:15 Calling Out the Cliff Strategy

Nathan refuses to let the exit stay vague, explicitly breaking down startup equity cliff timelines to highlight that Dan was terminated two weeks before vesting.

 Biggest teaching moment ▶ 2:46 Re-educating on Conversational Marketing

Dan educates Nathan on the fundamental paradigm shift from asynchronous email marketing to real-time, conversational bot interactions at the bottom of the funnel.

 Nathan holds their own ▶ 21:45 Founder Perspective on Employee Equity

Nathan demonstrates executive domain expertise by providing a framework for how startup candidates should structure milestone-based equity negotiations.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
ManyChat Strategy and Conversational Bot Optimization 4512 Nathan relates his personal struggles configuring ManyChat sequences and asks whether to mimic human chat. Dan corrects his premise by clarifying that Messenger bots should not be treated like email autoresponders but as conversational bottom-of-funnel touchpoints.
ManyChat Metrics, Pricing, and Origins 5313 Nathan drills Dan on user metrics, pricing tiers, and funding history, applying 80/20 rules to estimate user distribution. Dan shares the history of pivoting from Telegram and metrics around lead subscriber valuation.
Dan's Role and Controversial Exit from ConvertKit 6216 Nathan probes deeply into Dan's departure from ConvertKit, pushing him to clarify whether he was fired. Nathan brings up ConvertKit's churn rate and standard startup 1-year cliff equity mechanics to expose how Dan was terminated weeks before vesting.
Childhood Origins of Imposter Syndrome and Self-Worth 2103 Nathan asks a piercing personal question regarding why Dan undervalued himself. Dan opens up in a vulnerable monologue about his relationship with his father and the roots of his imposter syndrome.
Negotiating Leverage at ManyChat and Setting Boundaries 7114 When Dan admits he has been at ManyChat for six months without finalizing equity, Nathan takes charge and provides a detailed tactical playbook on how early employees should time-box trial periods to negotiate compensation from a position of leverage.
Sponsor Segment: Acuity Scheduling 2101 Nathan delivers a sponsor spot for Acuity Scheduling before conducting the standard Famous Five lightning round, maintaining a light and collaborative tone.

Statements from this episode (8)

Insight
Gamito: Email marketing tactics fail when applied to Messenger
“I think a lot of people are jumping into messenger from email marketing and they think that the things that are going to work in email are going to work in messenger. And that's just not the case. Messenger is a conversational tool. Email is something that you…”
Dan Gamito Jun 23, 2017 ▶ 2:47
Opinion
Gamito: Messenger marketing is most effective at the bottom of the funnel
“Really where, where messenger shines right now for marketers is at the bottom of the funnel.”
Dan Gamito Jun 23, 2017 ▶ 5:13
Insight
Gamito: A ManyChat subscriber is worth 5x to 10x an email subscriber
“So far the numbers are that a ManyChat subscriber is worth maybe five times to 10 times more than an email subscriber.”
Dan Gamito Jun 23, 2017 ▶ 6:44
Assertion Not checkable as stated
Gamito: ManyChat CEO grew a Telegram bot product to 100,000 bots
“He built something similar on telegram and he very quickly grew it to like a 100,000 bots.”
Dan Gamito Jun 23, 2017 ▶ 8:11
Disclosure
Gamito: ManyChat is sustaining 70% month-over-month growth
“We've doubled, we've almost doubled that. We last quarter and then we've been sustaining about 70% growth every month.”
Dan Gamito Jun 23, 2017 ▶ 9:27
Disclosure
Gamito: Nathan Barry hired him as ConvertKit's first full-time employee
“I was Nathan's first hire at ConvertKit. I was his first full-time hire and he brought me on to do marketing and this new emerging thing, which was needed called customer success.”
Dan Gamito Jun 23, 2017 ▶ 10:32
Assertion Not checkable as stated
Gamito: Nathan Barry fired him two weeks before ConvertKit equity vested
“I think my equity was supposed to vest and that director position was supposed to vest the next month, like two weeks after that. So it was a very strategic move on his part.”
Dan Gamito Jun 23, 2017 ▶ 15:16
Disclosure
Gamito: Equity at ManyChat is still under negotiation
“No, that's still in negotiation.”
Dan Gamito Jun 23, 2017 ▶ 20:49
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