StarZero All shows Try the podcast clipper →

Feb 4, 2016 · 23m · top-founders

This is How Much Revenue Ontraport Does with Landon Ray

Landon Ray · 14m 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

Ontraport founder and CEO Landon Ray joins host Nathan Latka on 'The Top' to share how he bootstrapped a marketing automation and CRM platform into an eight-figure SaaS enterprise. Landon details his journey from day trading to software development, transparently breaking down Ontraport's revenue metrics, pricing evolution, and profit-driven business philosophy.

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 32.1% of the talking time here. How this is scored →

Nathan as informed peer 4.5 Guest teaching 3.1 Guest disagreement 2.3 Nathan pushing back 3.4
05100:0010:0020:001:13–3:58 · Nathan as informed peer 4/10 Introducing Ontraport Founder and CEO Landon Ray Nathan introduces Landon's colorful backstory and asks for his best sales pitch as a street flower vendor. Landon gently corrects the romanticized premise by noting it was at farmer's markets where flowers sold themselves.3:59–6:39 · Nathan as informed peer 4/10 Transitioning from Day Trading to Software Development Landon recounts transitioning from independent trading to SEO and eventually building internal software tools. Nathan tracks the timeline and clarifies details with light chronological check-ins.6:39–10:26 · Nathan as informed peer 6/10 Five Years of Struggle and Early Bootstrapping Landon immediately corrects Nathan's multi-year struggle timeline, clarifying it started in 2004 rather than 2006. Nathan drills aggressively into the cap table and executive equity grants, prompting Landon to draw a boundary on revealing exact percentages.10:26–14:06 · Nathan as informed peer 8/10 Ontraport Pricing Strategy and Annual Recurring Revenue Nathan actively dissects Ontraport's metrics, pushing past the headline user number to distinguish free users from the roughly 6,000 paying accounts. He demonstrates strong SaaS fluency by performing real-time math to estimate their ARR between 14 and 20 million dollars.14:07–16:31 · Nathan as informed peer 5/10 Bootstrapped Profitability and Operational Leadership Challenges Landon explains the practical discipline required to maintain bootstrapped profitability and the steep learning curve of engineering management. Nathan validates the operational maturity he witnessed firsthand at Ontraport's event.16:31–19:13 · Nathan as informed peer 6/10 Hypothetical Acquisition Offers and Silicon Valley Culture Nathan poses a hundred-million-dollar acquisition hypothetical and holds Landon accountable when he floats taking 50 million for a minority stake. Landon critiques Silicon Valley's VC mindset, arguing that losing money every month is not a winning strategy.19:14–23:17 · Nathan as informed peer 3/10 Podcast Giveaway Promotion and Entry Instructions Nathan runs through his standard Famous Five rapid-fire questions covering personal habits, work-life boundaries, and formative advice. Landon participates openly without friction.23:24–23:54 · Nathan as informed peer 0/10 Episode Conclusion and Upcoming Episode Preview Solo closing monologue featuring podcast promotion, giveaway details, and a preview of the upcoming episode.1:13–3:58 · Guest teaching 3/10 Introducing Ontraport Founder and CEO Landon Ray Nathan introduces Landon's colorful backstory and asks for his best sales pitch as a street flower vendor. Landon gently corrects the romanticized premise by noting it was at farmer's markets where flowers sold themselves.3:59–6:39 · Guest teaching 2/10 Transitioning from Day Trading to Software Development Landon recounts transitioning from independent trading to SEO and eventually building internal software tools. Nathan tracks the timeline and clarifies details with light chronological check-ins.6:39–10:26 · Guest teaching 4/10 Five Years of Struggle and Early Bootstrapping Landon immediately corrects Nathan's multi-year struggle timeline, clarifying it started in 2004 rather than 2006. Nathan drills aggressively into the cap table and executive equity grants, prompting Landon to draw a boundary on revealing exact percentages.10:26–14:06 · Guest teaching 4/10 Ontraport Pricing Strategy and Annual Recurring Revenue Nathan actively dissects Ontraport's metrics, pushing past the headline user number to distinguish free users from the roughly 6,000 paying accounts. He demonstrates strong SaaS fluency by performing real-time math to estimate their ARR between 14 and 20 million dollars.14:07–16:31 · Guest teaching 5/10 Bootstrapped Profitability and Operational Leadership Challenges Landon explains the practical discipline required to maintain bootstrapped profitability and the steep learning curve of engineering management. Nathan validates the operational maturity he witnessed firsthand at Ontraport's event.16:31–19:13 · Guest teaching 5/10 Hypothetical Acquisition Offers and Silicon Valley Culture Nathan poses a hundred-million-dollar acquisition hypothetical and holds Landon accountable when he floats taking 50 million for a minority stake. Landon critiques Silicon Valley's VC mindset, arguing that losing money every month is not a winning strategy.19:14–23:17 · Guest teaching 2/10 Podcast Giveaway Promotion and Entry Instructions Nathan runs through his standard Famous Five rapid-fire questions covering personal habits, work-life boundaries, and formative advice. Landon participates openly without friction.23:24–23:54 · Guest teaching 0/10 Episode Conclusion and Upcoming Episode Preview Solo closing monologue featuring podcast promotion, giveaway details, and a preview of the upcoming episode.1:13–3:58 · Guest disagreement 2/10 Introducing Ontraport Founder and CEO Landon Ray Nathan introduces Landon's colorful backstory and asks for his best sales pitch as a street flower vendor. Landon gently corrects the romanticized premise by noting it was at farmer's markets where flowers sold themselves.3:59–6:39 · Guest disagreement 1/10 Transitioning from Day Trading to Software Development Landon recounts transitioning from independent trading to SEO and eventually building internal software tools. Nathan tracks the timeline and clarifies details with light chronological check-ins.6:39–10:26 · Guest disagreement 4/10 Five Years of Struggle and Early Bootstrapping Landon immediately corrects Nathan's multi-year struggle timeline, clarifying it started in 2004 rather than 2006. Nathan drills aggressively into the cap table and executive equity grants, prompting Landon to draw a boundary on revealing exact percentages.10:26–14:06 · Guest disagreement 3/10 Ontraport Pricing Strategy and Annual Recurring Revenue Nathan actively dissects Ontraport's metrics, pushing past the headline user number to distinguish free users from the roughly 6,000 paying accounts. He demonstrates strong SaaS fluency by performing real-time math to estimate their ARR between 14 and 20 million dollars.14:07–16:31 · Guest disagreement 2/10 Bootstrapped Profitability and Operational Leadership Challenges Landon explains the practical discipline required to maintain bootstrapped profitability and the steep learning curve of engineering management. Nathan validates the operational maturity he witnessed firsthand at Ontraport's event.16:31–19:13 · Guest disagreement 5/10 Hypothetical Acquisition Offers and Silicon Valley Culture Nathan poses a hundred-million-dollar acquisition hypothetical and holds Landon accountable when he floats taking 50 million for a minority stake. Landon critiques Silicon Valley's VC mindset, arguing that losing money every month is not a winning strategy.19:14–23:17 · Guest disagreement 1/10 Podcast Giveaway Promotion and Entry Instructions Nathan runs through his standard Famous Five rapid-fire questions covering personal habits, work-life boundaries, and formative advice. Landon participates openly without friction.23:24–23:54 · Guest disagreement 0/10 Episode Conclusion and Upcoming Episode Preview Solo closing monologue featuring podcast promotion, giveaway details, and a preview of the upcoming episode.1:13–3:58 · Nathan pushing back 2/10 Introducing Ontraport Founder and CEO Landon Ray Nathan introduces Landon's colorful backstory and asks for his best sales pitch as a street flower vendor. Landon gently corrects the romanticized premise by noting it was at farmer's markets where flowers sold themselves.3:59–6:39 · Nathan pushing back 2/10 Transitioning from Day Trading to Software Development Landon recounts transitioning from independent trading to SEO and eventually building internal software tools. Nathan tracks the timeline and clarifies details with light chronological check-ins.6:39–10:26 · Nathan pushing back 6/10 Five Years of Struggle and Early Bootstrapping Landon immediately corrects Nathan's multi-year struggle timeline, clarifying it started in 2004 rather than 2006. Nathan drills aggressively into the cap table and executive equity grants, prompting Landon to draw a boundary on revealing exact percentages.10:26–14:06 · Nathan pushing back 7/10 Ontraport Pricing Strategy and Annual Recurring Revenue Nathan actively dissects Ontraport's metrics, pushing past the headline user number to distinguish free users from the roughly 6,000 paying accounts. He demonstrates strong SaaS fluency by performing real-time math to estimate their ARR between 14 and 20 million dollars.14:07–16:31 · Nathan pushing back 2/10 Bootstrapped Profitability and Operational Leadership Challenges Landon explains the practical discipline required to maintain bootstrapped profitability and the steep learning curve of engineering management. Nathan validates the operational maturity he witnessed firsthand at Ontraport's event.16:31–19:13 · Nathan pushing back 7/10 Hypothetical Acquisition Offers and Silicon Valley Culture Nathan poses a hundred-million-dollar acquisition hypothetical and holds Landon accountable when he floats taking 50 million for a minority stake. Landon critiques Silicon Valley's VC mindset, arguing that losing money every month is not a winning strategy.19:14–23:17 · Nathan pushing back 1/10 Podcast Giveaway Promotion and Entry Instructions Nathan runs through his standard Famous Five rapid-fire questions covering personal habits, work-life boundaries, and formative advice. Landon participates openly without friction.23:24–23:54 · Nathan pushing back 0/10 Episode Conclusion and Upcoming Episode Preview Solo closing monologue featuring podcast promotion, giveaway details, and a preview of the upcoming episode.

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

0:00 · Nathan 78.4% · guest 21.6%0:00 · Nathan 78.4% · guest 21.6%3:00 · Nathan 6.4% · guest 93.6%3:00 · Nathan 6.4% · guest 93.6%6:00 · Nathan 27.7% · guest 72.3%6:00 · Nathan 27.7% · guest 72.3%9:00 · Nathan 20% · guest 80%9:00 · Nathan 20% · guest 80%12:00 · Nathan 40.2% · guest 59.8%12:00 · Nathan 40.2% · guest 59.8%15:00 · Nathan 8.8% · guest 91.2%15:00 · Nathan 8.8% · guest 91.2%18:00 · Nathan 32.1% · guest 67.9%18:00 · Nathan 32.1% · guest 67.9%21:00 · Nathan 44.8% · guest 55.2%21:00 · Nathan 44.8% · guest 55.2%
Sharpest disagreement ▶ 18:36 Landon dismisses VC cash-burning mentality

Landon sharply rejects the conventional Silicon Valley VC mindset, asserting that losing money every month makes no sense as a path to winning.

 Hardest push from Nathan ▶ 18:01 Nathan presses on hypothetical equity sale percentage

When Landon hedges on an acquisition but suggests selling a piece for 50 million, Nathan refuses to let him dodge and repeatedly pushes him to name the exact equity chunk.

 Biggest teaching moment ▶ 6:48 Landon corrects the failure timeline

Landon firmly interrupts Nathan's summary to correct the record, pointing out the painful struggle lasted a full five years starting back in 2004.

 Nathan holds their own ▶ 12:49 Nathan extracts true ARR through live unit economics

Nathan cuts through vanity total user figures to isolate the 6,000 paying customers and runs instant calculations to peg true annual recurring revenue between 14 and 20 million dollars.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Introducing Ontraport Founder and CEO Landon Ray 4322 Nathan introduces Landon's colorful backstory and asks for his best sales pitch as a street flower vendor. Landon gently corrects the romanticized premise by noting it was at farmer's markets where flowers sold themselves.
Transitioning from Day Trading to Software Development 4212 Landon recounts transitioning from independent trading to SEO and eventually building internal software tools. Nathan tracks the timeline and clarifies details with light chronological check-ins.
Five Years of Struggle and Early Bootstrapping 6446 Landon immediately corrects Nathan's multi-year struggle timeline, clarifying it started in 2004 rather than 2006. Nathan drills aggressively into the cap table and executive equity grants, prompting Landon to draw a boundary on revealing exact percentages.
Ontraport Pricing Strategy and Annual Recurring Revenue 8437 Nathan actively dissects Ontraport's metrics, pushing past the headline user number to distinguish free users from the roughly 6,000 paying accounts. He demonstrates strong SaaS fluency by performing real-time math to estimate their ARR between 14 and 20 million dollars.
Bootstrapped Profitability and Operational Leadership Challenges 5522 Landon explains the practical discipline required to maintain bootstrapped profitability and the steep learning curve of engineering management. Nathan validates the operational maturity he witnessed firsthand at Ontraport's event.
Hypothetical Acquisition Offers and Silicon Valley Culture 6557 Nathan poses a hundred-million-dollar acquisition hypothetical and holds Landon accountable when he floats taking 50 million for a minority stake. Landon critiques Silicon Valley's VC mindset, arguing that losing money every month is not a winning strategy.
Podcast Giveaway Promotion and Entry Instructions 3211 Nathan runs through his standard Famous Five rapid-fire questions covering personal habits, work-life boundaries, and formative advice. Landon participates openly without friction.
Episode Conclusion and Upcoming Episode Preview 0000 Solo closing monologue featuring podcast promotion, giveaway details, and a preview of the upcoming episode.

Statements from this episode (10)

Disclosure
Ray's Day Trading Income Dropped From Millions in 2000 to $100K
“In 2000, I probably made a couple million dollars. And then in 2001, I probably made a hundred grand for more work.”
Landon Ray Feb 4, 2016 ▶ 4:38
Insight
Ray Abandoned SEO Business in 2005 Over Google Algorithm Risk
“About a year into it, I realized like being in the SEO business was not a good move because one day Google was probably going to take away all my results and I was getting up with my tail between my legs.”
Landon Ray Feb 4, 2016 ▶ 5:25
Disclosure
Ontraport Suffered Multiple Launch Failures Before Finding Traction in 2009
“2006. We moved and then it took us to 2007 to launch anything. And then we launched something and then that flopped and we launched something else in 2008 and that kind of like limped along. And then we launched another version in 2009 and that's when things e…”
Landon Ray Feb 4, 2016 ▶ 6:26
Disclosure
Ray Invested Hundreds of Thousands and Deferred Salary for Five Years
“Oh, hundreds of thousands of dollars. And that's it. And that's if you don't count the fact that I didn't take a salary for all those years. So, you know, because I had savings, so I was able to do that.”
Landon Ray Feb 4, 2016 ▶ 7:20
Assertion Partly supported
Ontraport Hits Mid-Teens Millions in Annual Revenue With 10,000 Customers
“Oh, we're, you know, 10,000 ish. And a hundred employees and, you know, in the mid teens in terms of revenue, And you know, we've, yeah, we've just exploded. We've made the Inc. 504 years in a row.”
Landon Ray Feb 4, 2016 ▶ 8:06
Disclosure
Ontraport Scaled Using Only $3 Million in Friends and Family Funding
“Three million bucks maybe altogether over, I mean, this is over 10 years.”
Landon Ray Feb 4, 2016 ▶ 8:43
Disclosure
Ontraport Originally Charged $1,600 Monthly Due to High Support Overhead
“When we first started selling this product, it was actually like 1600 dollars a month. And that's because we didn't have the wherewithal internally to support clients for less because we didn't have documentation and we didn't have support and we didn't have a…”
Landon Ray Feb 4, 2016 ▶ 11:24
Assertion Not checkable as stated
Ontraport Had 6,000 Paying Customers Out of 10,000 Total Users
“If you want to talk about paying customers, it's probably more in the order of like 6000.”
Landon Ray Feb 4, 2016 ▶ 13:03
Assertion Not checkable as stated
Ontraport Scaled to Mid-Teens Millions Without Paid Marketing Until 2015
“We've never done paid marketing in our lives until like a few months ago.”
Landon Ray Feb 4, 2016 ▶ 17:24
Disclosure
Ray Maintained a Strict 5:30 PM Cutoff Time While Building Ontraport
“One of the commitments I made at the very beginning of my business was that I was going to be home at 5:30 every night and not miss my kids growing up. And I've pretty much accomplished that.”
Landon Ray Feb 4, 2016 ▶ 21:43
Made with StarZero

Turn any episode into a week of clips.

This entire site, over 2,600 episodes transcribed, diarized, checked and made playable, runs on the StarZero media pipeline. Drop in your own episode and the podcast clipper finds the moments worth sharing, cuts them, captions them, and reframes them for every feed.

Try the podcast clipper Learn more