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May 27, 2018 · 20m · top-founders

1037 Clate Mask on ICON, Infusionsoft IPO, Exit Strategy

Clate Mask · 11m spoken Nathan Latka · 6m 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 Entrepreneurs, host Nathan Latka interviews Infusionsoft co-founder and CEO Clate Mask to address buyout rumors, the strategic decision to cancel their ICON conference, and the company's pivot to sustainable profitability.

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 37.2% of the talking time here. How this is scored →

Nathan as informed peer 4.8 Guest teaching 4.4 Guest disagreement 2.8 Nathan pushing back 4.6
05100:0010:0020:000:49–7:22 · Nathan as informed peer 6/10 Welcoming Clate Mask and Context for the Interview Nathan presses Clate on why Infusionsoft canceled its flagship annual conference Icon, arguing it hurts developer ecosystem incentives and could be due to board profitability pressure. Clate counters by explaining the economics of SMB customers versus enterprise corporate expense accounts at conferences like Dreamforce.7:23–12:04 · Nathan as informed peer 5/10 Transitioning to Profitability and Employee Liquidity Events Nathan inquires about Infusionsoft's transition to profitability and how early employees achieve liquidity without an IPO. Clate educates on how they structured secondary share sales during their Bain round for pre-VC employees.12:06–15:30 · Nathan as informed peer 6/10 Mid-Roll Sponsor Segment: Hotjar Website Analytics After the mid-roll ad, Nathan challenges Clate on whether Infusionsoft has become a slow-growth lifestyle business under VC pressure since it has not raised capital or IPO'd in three years. Clate sharply dismisses the panic narrative, stating that profitability removes cash-burn timelines and gives the company full control over its destiny.15:31–19:40 · Nathan as informed peer 5/10 Executive Leadership Division Between CEO and COO Nathan brings up insider rumors that Clate has been sidelined into a mere figurehead role while operating executives run the company, as well as raising questions about an interim CTO. Clate immediately corrects Nathan's executive details (COO vs. CRO) and explains the intentional bifurcation between external leadership and internal operations at scale.19:41–20:13 · Nathan as informed peer 2/10 Interview Conclusion and Final Takeaways Nathan wraps up the episode by summarizing Clate's key explanations regarding the Icon cancellation, operational structure, and refusal of potential acquisition offers. Clate thanks Nathan for the chance to clear the air.0:49–7:22 · Guest teaching 5/10 Welcoming Clate Mask and Context for the Interview Nathan presses Clate on why Infusionsoft canceled its flagship annual conference Icon, arguing it hurts developer ecosystem incentives and could be due to board profitability pressure. Clate counters by explaining the economics of SMB customers versus enterprise corporate expense accounts at conferences like Dreamforce.7:23–12:04 · Guest teaching 5/10 Transitioning to Profitability and Employee Liquidity Events Nathan inquires about Infusionsoft's transition to profitability and how early employees achieve liquidity without an IPO. Clate educates on how they structured secondary share sales during their Bain round for pre-VC employees.12:06–15:30 · Guest teaching 6/10 Mid-Roll Sponsor Segment: Hotjar Website Analytics After the mid-roll ad, Nathan challenges Clate on whether Infusionsoft has become a slow-growth lifestyle business under VC pressure since it has not raised capital or IPO'd in three years. Clate sharply dismisses the panic narrative, stating that profitability removes cash-burn timelines and gives the company full control over its destiny.15:31–19:40 · Guest teaching 6/10 Executive Leadership Division Between CEO and COO Nathan brings up insider rumors that Clate has been sidelined into a mere figurehead role while operating executives run the company, as well as raising questions about an interim CTO. Clate immediately corrects Nathan's executive details (COO vs. CRO) and explains the intentional bifurcation between external leadership and internal operations at scale.19:41–20:13 · Guest teaching 0/10 Interview Conclusion and Final Takeaways Nathan wraps up the episode by summarizing Clate's key explanations regarding the Icon cancellation, operational structure, and refusal of potential acquisition offers. Clate thanks Nathan for the chance to clear the air.0:49–7:22 · Guest disagreement 3/10 Welcoming Clate Mask and Context for the Interview Nathan presses Clate on why Infusionsoft canceled its flagship annual conference Icon, arguing it hurts developer ecosystem incentives and could be due to board profitability pressure. Clate counters by explaining the economics of SMB customers versus enterprise corporate expense accounts at conferences like Dreamforce.7:23–12:04 · Guest disagreement 2/10 Transitioning to Profitability and Employee Liquidity Events Nathan inquires about Infusionsoft's transition to profitability and how early employees achieve liquidity without an IPO. Clate educates on how they structured secondary share sales during their Bain round for pre-VC employees.12:06–15:30 · Guest disagreement 5/10 Mid-Roll Sponsor Segment: Hotjar Website Analytics After the mid-roll ad, Nathan challenges Clate on whether Infusionsoft has become a slow-growth lifestyle business under VC pressure since it has not raised capital or IPO'd in three years. Clate sharply dismisses the panic narrative, stating that profitability removes cash-burn timelines and gives the company full control over its destiny.15:31–19:40 · Guest disagreement 4/10 Executive Leadership Division Between CEO and COO Nathan brings up insider rumors that Clate has been sidelined into a mere figurehead role while operating executives run the company, as well as raising questions about an interim CTO. Clate immediately corrects Nathan's executive details (COO vs. CRO) and explains the intentional bifurcation between external leadership and internal operations at scale.19:41–20:13 · Guest disagreement 0/10 Interview Conclusion and Final Takeaways Nathan wraps up the episode by summarizing Clate's key explanations regarding the Icon cancellation, operational structure, and refusal of potential acquisition offers. Clate thanks Nathan for the chance to clear the air.0:49–7:22 · Nathan pushing back 6/10 Welcoming Clate Mask and Context for the Interview Nathan presses Clate on why Infusionsoft canceled its flagship annual conference Icon, arguing it hurts developer ecosystem incentives and could be due to board profitability pressure. Clate counters by explaining the economics of SMB customers versus enterprise corporate expense accounts at conferences like Dreamforce.7:23–12:04 · Nathan pushing back 4/10 Transitioning to Profitability and Employee Liquidity Events Nathan inquires about Infusionsoft's transition to profitability and how early employees achieve liquidity without an IPO. Clate educates on how they structured secondary share sales during their Bain round for pre-VC employees.12:06–15:30 · Nathan pushing back 7/10 Mid-Roll Sponsor Segment: Hotjar Website Analytics After the mid-roll ad, Nathan challenges Clate on whether Infusionsoft has become a slow-growth lifestyle business under VC pressure since it has not raised capital or IPO'd in three years. Clate sharply dismisses the panic narrative, stating that profitability removes cash-burn timelines and gives the company full control over its destiny.15:31–19:40 · Nathan pushing back 6/10 Executive Leadership Division Between CEO and COO Nathan brings up insider rumors that Clate has been sidelined into a mere figurehead role while operating executives run the company, as well as raising questions about an interim CTO. Clate immediately corrects Nathan's executive details (COO vs. CRO) and explains the intentional bifurcation between external leadership and internal operations at scale.19:41–20:13 · Nathan pushing back 0/10 Interview Conclusion and Final Takeaways Nathan wraps up the episode by summarizing Clate's key explanations regarding the Icon cancellation, operational structure, and refusal of potential acquisition offers. Clate thanks Nathan for the chance to clear the air.

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

0:00 · Nathan 52.6% · guest 47.4%0:00 · Nathan 52.6% · guest 47.4%3:00 · Nathan 26.6% · guest 73.4%3:00 · Nathan 26.6% · guest 73.4%6:00 · Nathan 28.8% · guest 71.2%6:00 · Nathan 28.8% · guest 71.2%9:00 · Nathan 27.4% · guest 72.6%9:00 · Nathan 27.4% · guest 72.6%12:00 · Nathan 71.1% · guest 28.9%12:00 · Nathan 71.1% · guest 28.9%15:00 · Nathan 21% · guest 79%15:00 · Nathan 21% · guest 79%18:00 · Nathan 30.5% · guest 69.5%18:00 · Nathan 30.5% · guest 69.5%
Sharpest disagreement ▶ 14:00 Rejection of the VC warning siren narrative

Clate rejects Nathan's framing that a 3-year gap without fundraising triggers warning sirens, countering that cash flow positivity renders timeline alarms irrelevant.

 Hardest push from Nathan ▶ 4:46 Nathan refuses board profitability rationale for canceling Icon

Nathan challenges Clate's reasoning for killing Icon, arguing that cutting the conference risks gutting the developer ecosystem that drives Infusionsoft's platform growth.

 Biggest teaching moment ▶ 15:54 Correcting insider rumors about executive division

Clate corrects Nathan's rumor regarding the CRO running the company, clarifying that the COO handles internal operations while he leads high-level strategy and external leadership.

 Nathan holds their own ▶ 4:46 Nathan cites prior metrics and Salesforce analogy

Nathan references specific quotes and ecosystem mechanics from their previous interview to drill Clate on the true motivations behind canceling the annual event.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Welcoming Clate Mask and Context for the Interview 6536 Nathan presses Clate on why Infusionsoft canceled its flagship annual conference Icon, arguing it hurts developer ecosystem incentives and could be due to board profitability pressure. Clate counters by explaining the economics of SMB customers versus enterprise corporate expense accounts at conferences like Dreamforce.
Transitioning to Profitability and Employee Liquidity Events 5524 Nathan inquires about Infusionsoft's transition to profitability and how early employees achieve liquidity without an IPO. Clate educates on how they structured secondary share sales during their Bain round for pre-VC employees.
Mid-Roll Sponsor Segment: Hotjar Website Analytics 6657 After the mid-roll ad, Nathan challenges Clate on whether Infusionsoft has become a slow-growth lifestyle business under VC pressure since it has not raised capital or IPO'd in three years. Clate sharply dismisses the panic narrative, stating that profitability removes cash-burn timelines and gives the company full control over its destiny.
Executive Leadership Division Between CEO and COO 5646 Nathan brings up insider rumors that Clate has been sidelined into a mere figurehead role while operating executives run the company, as well as raising questions about an interim CTO. Clate immediately corrects Nathan's executive details (COO vs. CRO) and explains the intentional bifurcation between external leadership and internal operations at scale.
Interview Conclusion and Final Takeaways 2000 Nathan wraps up the episode by summarizing Clate's key explanations regarding the Icon cancellation, operational structure, and refusal of potential acquisition offers. Clate thanks Nathan for the chance to clear the air.

Statements from this episode (6)

Disclosure
Clate Mask: Infusionsoft is profitable and no longer requires VC funding
“We've grown to a point where we're not dependent on venture capital. We're not dependent on outside revenues or outside funding sources. And we've built a profitable growing business that no longer requires that kind of funding.”
Clate Mask May 27, 2018 ▶ 2:00
Disclosure
Mask: Infusionsoft has 150k users, but only 3k attended ICON
“When you get to a point that you've got a 150,000 users and only 3000 of them can afford to leave their business for a week, come and put a lot of things on pause to invest in their growth.”
Clate Mask May 27, 2018 ▶ 2:49
Assertion Not checkable as stated
Mask: Infusionsoft has been cash-flow positive for about a year
“Correct. Have been for about a year.”
Clate Mask May 27, 2018 ▶ 9:42
Assertion Not checkable as stated
Mask: Infusionsoft let all pre-VC employees sell shares in Series D
“Yeah, we made it possible for everybody that was, that had options prior to raising venture capital. So for all those brave souls who took the leap before we had any financial backing whatsoever, At the Series D, we gave them an opportunity to sell some shares”
Clate Mask May 27, 2018 ▶ 10:54
Disclosure
Mask: Infusionsoft has no intention or ambition to sell
“Another way you can do it is if the company sells, that's not our ambition. That's not our intent.”
Clate Mask May 27, 2018 ▶ 11:39
Disclosure
Mask says he would reject a hypothetical $900M buyout offer
“I say no. We got a mission that's really exciting.”
Clate Mask May 27, 2018 ▶ 17:15
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