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Jan 22, 2018 · 20m · top-founders

912 SaaS: Internet Hacker Builds Bootstrapped Productivity Tool, Passes $2.4m in ARR

Rob Rawson · 10m spoken Nathan Latka · 8m spoken
0:00 / 0:00

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In this episode of The Top Entrepreneurs Podcast, host Nathan Latka interviews Time Doctor co-founder Rob Rawson, who details how he transitioned from practicing medicine to bootstrapping a remote workforce analytics platform to $210,000 MRR and $2.4M ARR. Rawson shares his unit economics, partner-driven organic customer acquisition channels, interactive onboarding funnels, and perspectives on SaaS company valuations.

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 44% of the talking time here. How this is scored →

Nathan as informed peer 4.8 Guest teaching 2.7 Guest disagreement 1.3 Nathan pushing back 3.0
05100:0010:0020:001:38–3:56 · Nathan as informed peer 7/10 Bootstrapping Time Doctor to $210K Monthly Recurring Revenue Nathan actively drills into Time Doctor's SaaS metrics and steps in to educate Rob on standard SaaS gross margin calculations when Rob admits he is unsure how COGS and hosting fees are defined.3:57–6:38 · Nathan as informed peer 4/10 Founding Origins and AI-Driven Remote Productivity Nathan draws comparisons between Time Doctor and Upwork's backend and probes why Rob does not sell off Staff.com to focus entirely on one product.6:39–10:10 · Nathan as informed peer 3/10 Leaving Medicine for High-Volume Affiliate Arbitrage Rob describes his background transitioning from medical school to high-volume marketing, explaining Google AdSense arbitrage to Nathan who is unfamiliar with the specific strategy.10:13–12:40 · Nathan as informed peer 6/10 Mid-Episode Sponsor Break: SignEasy Following the mid-roll ad, Nathan leverages SimilarWeb competitive intelligence to highlight specific integration documentation pages driving Time Doctor's organic inbound traffic.12:41–18:12 · Nathan as informed peer 7/10 Funnel Optimization and Hypothetical Acquisition Valuations Nathan live-audits the three-step onboarding quiz on Time Doctor's website to extract exact funnel conversion metrics, then aggressively pushes Rob on acquisition multiples.18:12–20:20 · Nathan as informed peer 2/10 The Famous Five and Episode Conclusion The interview concludes smoothly with Nathan running through the standard Famous Five rapid-fire questions and summarizing key company metrics.1:38–3:56 · Guest teaching 1/10 Bootstrapping Time Doctor to $210K Monthly Recurring Revenue Nathan actively drills into Time Doctor's SaaS metrics and steps in to educate Rob on standard SaaS gross margin calculations when Rob admits he is unsure how COGS and hosting fees are defined.3:57–6:38 · Guest teaching 3/10 Founding Origins and AI-Driven Remote Productivity Nathan draws comparisons between Time Doctor and Upwork's backend and probes why Rob does not sell off Staff.com to focus entirely on one product.6:39–10:10 · Guest teaching 5/10 Leaving Medicine for High-Volume Affiliate Arbitrage Rob describes his background transitioning from medical school to high-volume marketing, explaining Google AdSense arbitrage to Nathan who is unfamiliar with the specific strategy.10:13–12:40 · Guest teaching 3/10 Mid-Episode Sponsor Break: SignEasy Following the mid-roll ad, Nathan leverages SimilarWeb competitive intelligence to highlight specific integration documentation pages driving Time Doctor's organic inbound traffic.12:41–18:12 · Guest teaching 3/10 Funnel Optimization and Hypothetical Acquisition Valuations Nathan live-audits the three-step onboarding quiz on Time Doctor's website to extract exact funnel conversion metrics, then aggressively pushes Rob on acquisition multiples.18:12–20:20 · Guest teaching 1/10 The Famous Five and Episode Conclusion The interview concludes smoothly with Nathan running through the standard Famous Five rapid-fire questions and summarizing key company metrics.1:38–3:56 · Guest disagreement 1/10 Bootstrapping Time Doctor to $210K Monthly Recurring Revenue Nathan actively drills into Time Doctor's SaaS metrics and steps in to educate Rob on standard SaaS gross margin calculations when Rob admits he is unsure how COGS and hosting fees are defined.3:57–6:38 · Guest disagreement 2/10 Founding Origins and AI-Driven Remote Productivity Nathan draws comparisons between Time Doctor and Upwork's backend and probes why Rob does not sell off Staff.com to focus entirely on one product.6:39–10:10 · Guest disagreement 1/10 Leaving Medicine for High-Volume Affiliate Arbitrage Rob describes his background transitioning from medical school to high-volume marketing, explaining Google AdSense arbitrage to Nathan who is unfamiliar with the specific strategy.10:13–12:40 · Guest disagreement 1/10 Mid-Episode Sponsor Break: SignEasy Following the mid-roll ad, Nathan leverages SimilarWeb competitive intelligence to highlight specific integration documentation pages driving Time Doctor's organic inbound traffic.12:41–18:12 · Guest disagreement 3/10 Funnel Optimization and Hypothetical Acquisition Valuations Nathan live-audits the three-step onboarding quiz on Time Doctor's website to extract exact funnel conversion metrics, then aggressively pushes Rob on acquisition multiples.18:12–20:20 · Guest disagreement 0/10 The Famous Five and Episode Conclusion The interview concludes smoothly with Nathan running through the standard Famous Five rapid-fire questions and summarizing key company metrics.1:38–3:56 · Nathan pushing back 4/10 Bootstrapping Time Doctor to $210K Monthly Recurring Revenue Nathan actively drills into Time Doctor's SaaS metrics and steps in to educate Rob on standard SaaS gross margin calculations when Rob admits he is unsure how COGS and hosting fees are defined.3:57–6:38 · Nathan pushing back 3/10 Founding Origins and AI-Driven Remote Productivity Nathan draws comparisons between Time Doctor and Upwork's backend and probes why Rob does not sell off Staff.com to focus entirely on one product.6:39–10:10 · Nathan pushing back 2/10 Leaving Medicine for High-Volume Affiliate Arbitrage Rob describes his background transitioning from medical school to high-volume marketing, explaining Google AdSense arbitrage to Nathan who is unfamiliar with the specific strategy.10:13–12:40 · Nathan pushing back 2/10 Mid-Episode Sponsor Break: SignEasy Following the mid-roll ad, Nathan leverages SimilarWeb competitive intelligence to highlight specific integration documentation pages driving Time Doctor's organic inbound traffic.12:41–18:12 · Nathan pushing back 6/10 Funnel Optimization and Hypothetical Acquisition Valuations Nathan live-audits the three-step onboarding quiz on Time Doctor's website to extract exact funnel conversion metrics, then aggressively pushes Rob on acquisition multiples.18:12–20:20 · Nathan pushing back 1/10 The Famous Five and Episode Conclusion The interview concludes smoothly with Nathan running through the standard Famous Five rapid-fire questions and summarizing key company metrics.

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

0:00 · Nathan 70% · guest 30%0:00 · Nathan 70% · guest 30%3:00 · Nathan 33.1% · guest 66.9%3:00 · Nathan 33.1% · guest 66.9%6:00 · Nathan 31.1% · guest 68.9%6:00 · Nathan 31.1% · guest 68.9%9:00 · Nathan 44.2% · guest 55.8%9:00 · Nathan 44.2% · guest 55.8%12:00 · Nathan 47.8% · guest 52.2%12:00 · Nathan 47.8% · guest 52.2%15:00 · Nathan 44.6% · guest 55.4%15:00 · Nathan 44.6% · guest 55.4%18:00 · Nathan 35.2% · guest 64.8%18:00 · Nathan 35.2% · guest 64.8%
Sharpest disagreement ▶ 17:21 Pushing back on inflated valuation multiples

Rob checks Nathan's aggressive 10x multiple valuation assumption, directly pointing out that standard market price for their profile is closer to 5x revenue.

 Hardest push from Nathan ▶ 16:46 Demanding an offensive buyout valuation figure

Nathan refuses to let Rob dodge the question about selling the company, pressing him repeatedly to name an irrationally high number.

 Biggest teaching moment ▶ 9:06 Educating the host on historical AdSense arbitrage

Rob explains the high-volume Google AdSense arbitrage model after Nathan admits he had not heard of the tactic.

 Nathan holds their own ▶ 2:37 Instructing the guest on SaaS gross margin calculations

Nathan demonstrates domain expertise by detailing exactly what expenses belong above the line in COGS when Rob expresses confusion about his 95% margin calculation.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Bootstrapping Time Doctor to $210K Monthly Recurring Revenue 7114 Nathan actively drills into Time Doctor's SaaS metrics and steps in to educate Rob on standard SaaS gross margin calculations when Rob admits he is unsure how COGS and hosting fees are defined.
Founding Origins and AI-Driven Remote Productivity 4323 Nathan draws comparisons between Time Doctor and Upwork's backend and probes why Rob does not sell off Staff.com to focus entirely on one product.
Leaving Medicine for High-Volume Affiliate Arbitrage 3512 Rob describes his background transitioning from medical school to high-volume marketing, explaining Google AdSense arbitrage to Nathan who is unfamiliar with the specific strategy.
Mid-Episode Sponsor Break: SignEasy 6312 Following the mid-roll ad, Nathan leverages SimilarWeb competitive intelligence to highlight specific integration documentation pages driving Time Doctor's organic inbound traffic.
Funnel Optimization and Hypothetical Acquisition Valuations 7336 Nathan live-audits the three-step onboarding quiz on Time Doctor's website to extract exact funnel conversion metrics, then aggressively pushes Rob on acquisition multiples.
The Famous Five and Episode Conclusion 2101 The interview concludes smoothly with Nathan running through the standard Famous Five rapid-fire questions and summarizing key company metrics.

Statements from this episode (12)

Disclosure
Rawson: Time Doctor employs over 50 people across 28 countries remotely
“Yeah, we have over 50 people in 28 countries all working from home, so it's completely distributed.”
Rob Rawson Jan 22, 2018 ▶ 3:14
Disclosure
Rawson: Time Doctor has raised zero outside capital
“Well, zero, zero.”
Rob Rawson Jan 22, 2018 ▶ 3:30
Opinion
Rawson: Screenshot monitoring is not the future of remote productivity
“We do have a screenshot feature similar to Upwork and the, that's great. And but I don't actually feel like that's the future. Like I say, I think the artificial intelligence part is the future because you can more accurately determine what What's actually goi…”
Rob Rawson Jan 22, 2018 ▶ 5:06
Disclosure
Rawson: Time Doctor Operates at Mostly Breakeven to Reinvest Profits
“No, actually, Time Doctor, we've been running at mostly breakeven because I'm trying to reinvest.”
Rob Rawson Jan 22, 2018 ▶ 7:41
Disclosure
Rawson Spent Peak of $400K in One Month on Google AdWords
“400 grand.”
Rob Rawson Jan 22, 2018 ▶ 8:54
Assertion Supported
Rawson: Google AdSense Arbitrage Is No Longer Viable
“It, and it was, it's not really possible anymore because Google kind of doesn't like it.”
Rob Rawson Jan 22, 2018 ▶ 9:21
Assertion Not publicly verifiable
Latka: Todoist support article is Time Doctor's top referral traffic driver
“Your number one traffic driver, according to similar web, is actually Todoist. There's a support article on Todoist that says, how do I use Todoist with Time Doctor? And that's driving you a ton of traffic.”
Nathan Latka Jan 22, 2018 ▶ 10:55
Assertion Not checkable as stated
Rawson: 50% of Time Doctor Homepage Visitors Engage with Questionnaire
“Out of a thousand people that are hitting it, around 50% are actually clicking yes or no.”
Rob Rawson Jan 22, 2018 ▶ 13:42
Assertion Not checkable as stated
Rawson: 35% of Time Doctor Visitors Complete Funnel Requesting Demo
“If you count both the yes that I manage or don't manage people, then it's going right down only to about 35%. So 35% have said yes, that they want to do a demo.”
Rob Rawson Jan 22, 2018 ▶ 14:53
Insight
Rawson: Initial Micro-Commitments Dramatically Increase Lead Form Conversions
“Once you start clicking, you're actually engaging, and then you've done the first three clicks. It's easy to now enter your email address as the next thing, and we've tested it a few times. It does work.”
Rob Rawson Jan 22, 2018 ▶ 15:55
Opinion
Rawson: SaaS Market Acquisition Multiples Are Roughly 5x Revenue
“I mean, 10 X is probably not really market price. Market price is probably like five X revenues.”
Rob Rawson Jan 22, 2018 ▶ 17:22
Disclosure
Rawson holds majority equity over his co-founder for providing initial capital
“No, I'm, cause I started earlier and I initially invested money, like I've got a larger percentage.”
Rob Rawson Jan 22, 2018 ▶ 17:50
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