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Aug 10, 2022 · 18m · top-founders

Secret tool you should use to manage documenting systems to have contractors run

Trent Dyrsmid · 8m spoken Nathan Latka · 7m 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 interview, Flowster founder Trent Dyrsmid shares how he scaled a profitable, bootstrapped SaaS company by doubling average revenue per user, executing an organic SEO strategy, and building standard operating procedures to delegate work to global remote contractors.

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 46.1% of the talking time here. How this is scored →

Nathan as informed peer 4.9 Guest teaching 2.0 Guest disagreement 2.0 Nathan pushing back 2.6
05100:0010:000:47–3:51 · Nathan as informed peer 6/10 Introducing Trent Dyrsmid and the Flowster Mission Nathan opens with specific historical benchmarks from their previous conversation (500 customers at $20/month). Trent details how doubling pricing and changing plans helped boost ARPU without major churn.3:51–5:54 · Nathan as informed peer 5/10 Organic Inbound Marketing and SEO Strategy Nathan probes Flowster's organic inbound funnel and SEO strategy. Trent explains their implementation of Brian Dean's power pages framework while acknowledging his wife manages the day-to-day content operation.5:54–8:44 · Nathan as informed peer 4/10 Engineering Management and Remote Team Structure Trent outlines his hands-off engineering philosophy, giving his technical co-founder complete autonomy to hire offshore developers across India, Africa, and Eastern Europe. Nathan introduces his thesis on high-leverage lean organizations followed by a sponsor read.8:47–11:42 · Nathan as informed peer 6/10 Frameworks for SOP Creation and Contractor Hiring The two exchange practical playbooks for outsourcing and standard operating procedures. Trent shares his proprietary test for contractor honesty, while Nathan details his own Upwork hiring filtration method.11:42–14:03 · Nathan as informed peer 6/10 Financial Metrics, Bootstrapping, and Future M&A Goals Trent flatly refuses to disclose customer numbers, triggering direct pushback from Nathan who points out that Trent disclosed them in their previous interview. After Trent stands firm on privacy, they shift to discussing profitability and long-term M&A aspirations.14:03–18:01 · Nathan as informed peer 7/10 Organizational Scaling and Executive Recruitment Strategy Nathan presses on revenue before calculating an estimate using industry benchmarks. He leverages his knowledge of sales economics to deduce that Trent is moving upmarket into enterprise deals based on his reading of Mark Roberge, and later surprises Trent with historical Ahrefs domain rating volatility.18:01–18:30 · Nathan as informed peer 0/10 Episode Conclusion and Flowster Summary Host monologue closing out the episode, summarizing Flowster's business model, team size, and historical growth trajectory.0:47–3:51 · Guest teaching 2/10 Introducing Trent Dyrsmid and the Flowster Mission Nathan opens with specific historical benchmarks from their previous conversation (500 customers at $20/month). Trent details how doubling pricing and changing plans helped boost ARPU without major churn.3:51–5:54 · Guest teaching 2/10 Organic Inbound Marketing and SEO Strategy Nathan probes Flowster's organic inbound funnel and SEO strategy. Trent explains their implementation of Brian Dean's power pages framework while acknowledging his wife manages the day-to-day content operation.5:54–8:44 · Guest teaching 2/10 Engineering Management and Remote Team Structure Trent outlines his hands-off engineering philosophy, giving his technical co-founder complete autonomy to hire offshore developers across India, Africa, and Eastern Europe. Nathan introduces his thesis on high-leverage lean organizations followed by a sponsor read.8:47–11:42 · Guest teaching 4/10 Frameworks for SOP Creation and Contractor Hiring The two exchange practical playbooks for outsourcing and standard operating procedures. Trent shares his proprietary test for contractor honesty, while Nathan details his own Upwork hiring filtration method.11:42–14:03 · Guest teaching 2/10 Financial Metrics, Bootstrapping, and Future M&A Goals Trent flatly refuses to disclose customer numbers, triggering direct pushback from Nathan who points out that Trent disclosed them in their previous interview. After Trent stands firm on privacy, they shift to discussing profitability and long-term M&A aspirations.14:03–18:01 · Guest teaching 2/10 Organizational Scaling and Executive Recruitment Strategy Nathan presses on revenue before calculating an estimate using industry benchmarks. He leverages his knowledge of sales economics to deduce that Trent is moving upmarket into enterprise deals based on his reading of Mark Roberge, and later surprises Trent with historical Ahrefs domain rating volatility.18:01–18:30 · Guest teaching 0/10 Episode Conclusion and Flowster Summary Host monologue closing out the episode, summarizing Flowster's business model, team size, and historical growth trajectory.0:47–3:51 · Guest disagreement 1/10 Introducing Trent Dyrsmid and the Flowster Mission Nathan opens with specific historical benchmarks from their previous conversation (500 customers at $20/month). Trent details how doubling pricing and changing plans helped boost ARPU without major churn.3:51–5:54 · Guest disagreement 1/10 Organic Inbound Marketing and SEO Strategy Nathan probes Flowster's organic inbound funnel and SEO strategy. Trent explains their implementation of Brian Dean's power pages framework while acknowledging his wife manages the day-to-day content operation.5:54–8:44 · Guest disagreement 1/10 Engineering Management and Remote Team Structure Trent outlines his hands-off engineering philosophy, giving his technical co-founder complete autonomy to hire offshore developers across India, Africa, and Eastern Europe. Nathan introduces his thesis on high-leverage lean organizations followed by a sponsor read.8:47–11:42 · Guest disagreement 1/10 Frameworks for SOP Creation and Contractor Hiring The two exchange practical playbooks for outsourcing and standard operating procedures. Trent shares his proprietary test for contractor honesty, while Nathan details his own Upwork hiring filtration method.11:42–14:03 · Guest disagreement 6/10 Financial Metrics, Bootstrapping, and Future M&A Goals Trent flatly refuses to disclose customer numbers, triggering direct pushback from Nathan who points out that Trent disclosed them in their previous interview. After Trent stands firm on privacy, they shift to discussing profitability and long-term M&A aspirations.14:03–18:01 · Guest disagreement 4/10 Organizational Scaling and Executive Recruitment Strategy Nathan presses on revenue before calculating an estimate using industry benchmarks. He leverages his knowledge of sales economics to deduce that Trent is moving upmarket into enterprise deals based on his reading of Mark Roberge, and later surprises Trent with historical Ahrefs domain rating volatility.18:01–18:30 · Guest disagreement 0/10 Episode Conclusion and Flowster Summary Host monologue closing out the episode, summarizing Flowster's business model, team size, and historical growth trajectory.0:47–3:51 · Nathan pushing back 2/10 Introducing Trent Dyrsmid and the Flowster Mission Nathan opens with specific historical benchmarks from their previous conversation (500 customers at $20/month). Trent details how doubling pricing and changing plans helped boost ARPU without major churn.3:51–5:54 · Nathan pushing back 1/10 Organic Inbound Marketing and SEO Strategy Nathan probes Flowster's organic inbound funnel and SEO strategy. Trent explains their implementation of Brian Dean's power pages framework while acknowledging his wife manages the day-to-day content operation.5:54–8:44 · Nathan pushing back 1/10 Engineering Management and Remote Team Structure Trent outlines his hands-off engineering philosophy, giving his technical co-founder complete autonomy to hire offshore developers across India, Africa, and Eastern Europe. Nathan introduces his thesis on high-leverage lean organizations followed by a sponsor read.8:47–11:42 · Nathan pushing back 1/10 Frameworks for SOP Creation and Contractor Hiring The two exchange practical playbooks for outsourcing and standard operating procedures. Trent shares his proprietary test for contractor honesty, while Nathan details his own Upwork hiring filtration method.11:42–14:03 · Nathan pushing back 7/10 Financial Metrics, Bootstrapping, and Future M&A Goals Trent flatly refuses to disclose customer numbers, triggering direct pushback from Nathan who points out that Trent disclosed them in their previous interview. After Trent stands firm on privacy, they shift to discussing profitability and long-term M&A aspirations.14:03–18:01 · Nathan pushing back 6/10 Organizational Scaling and Executive Recruitment Strategy Nathan presses on revenue before calculating an estimate using industry benchmarks. He leverages his knowledge of sales economics to deduce that Trent is moving upmarket into enterprise deals based on his reading of Mark Roberge, and later surprises Trent with historical Ahrefs domain rating volatility.18:01–18:30 · Nathan pushing back 0/10 Episode Conclusion and Flowster Summary Host monologue closing out the episode, summarizing Flowster's business model, team size, and historical growth trajectory.

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

0:00 · Nathan 60.5% · guest 39.5%0:00 · Nathan 60.5% · guest 39.5%3:00 · Nathan 23.5% · guest 76.5%3:00 · Nathan 23.5% · guest 76.5%6:00 · Nathan 69.5% · guest 30.5%6:00 · Nathan 69.5% · guest 30.5%9:00 · Nathan 28.5% · guest 71.5%9:00 · Nathan 28.5% · guest 71.5%12:00 · Nathan 44.5% · guest 55.5%12:00 · Nathan 44.5% · guest 55.5%15:00 · Nathan 41.5% · guest 58.5%15:00 · Nathan 41.5% · guest 58.5%18:00 · Nathan 94.4% · guest 5.6%18:00 · Nathan 94.4% · guest 5.6%
Sharpest disagreement ▶ 11:45 Refusing metric disclosure

Trent stonewalls Nathan's inquiry into customer numbers, declaring that as a private company they will no longer disclose revenue or customer volume.

 Hardest push from Nathan ▶ 12:00 Challenging the refusal to share data

Nathan refuses to let Trent's deflection pass without challenge, highlighting that Trent had openly shared the exact metric in their previous conversation and asking what changed.

 Biggest teaching moment ▶ 11:06 Vetting freelancer honesty via task duration

Trent educates Nathan on his subtle hiring tactic: assigning a 15-minute task with an expected one-hour window to catch contractors billing extra time versus admitting it took far less.

 Nathan holds their own ▶ 15:32 Connecting sales literature to ACV math

Nathan demonstrates sharp domain expertise by pointing out that Mark Roberge's playbook requires an ACV of at least $5,000 to $10,000 to justify commission, correctly prompting Trent to reveal upcoming enterprise plans.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Introducing Trent Dyrsmid and the Flowster Mission 6212 Nathan opens with specific historical benchmarks from their previous conversation (500 customers at $20/month). Trent details how doubling pricing and changing plans helped boost ARPU without major churn.
Organic Inbound Marketing and SEO Strategy 5211 Nathan probes Flowster's organic inbound funnel and SEO strategy. Trent explains their implementation of Brian Dean's power pages framework while acknowledging his wife manages the day-to-day content operation.
Engineering Management and Remote Team Structure 4211 Trent outlines his hands-off engineering philosophy, giving his technical co-founder complete autonomy to hire offshore developers across India, Africa, and Eastern Europe. Nathan introduces his thesis on high-leverage lean organizations followed by a sponsor read.
Frameworks for SOP Creation and Contractor Hiring 6411 The two exchange practical playbooks for outsourcing and standard operating procedures. Trent shares his proprietary test for contractor honesty, while Nathan details his own Upwork hiring filtration method.
Financial Metrics, Bootstrapping, and Future M&A Goals 6267 Trent flatly refuses to disclose customer numbers, triggering direct pushback from Nathan who points out that Trent disclosed them in their previous interview. After Trent stands firm on privacy, they shift to discussing profitability and long-term M&A aspirations.
Organizational Scaling and Executive Recruitment Strategy 7246 Nathan presses on revenue before calculating an estimate using industry benchmarks. He leverages his knowledge of sales economics to deduce that Trent is moving upmarket into enterprise deals based on his reading of Mark Roberge, and later surprises Trent with historical Ahrefs domain rating volatility.
Episode Conclusion and Flowster Summary 0000 Host monologue closing out the episode, summarizing Flowster's business model, team size, and historical growth trajectory.

Statements from this episode (9)

Assertion Not checkable as stated
Flowster's average revenue per user has doubled to roughly $40
“ARPU is actually double that now.”
Trent Dyrsmid Aug 10, 2022 ▶ 2:31
Assertion Not checkable as stated
Flowster generates 30 to 50 inbound organic leads daily
“We, just because of the content marketing that we're doing and the Facebook groups and the YouTube channel and the stuff, we are adding around 30 to 50 leads a day into the funnel and they just keep coming every day, day after day.”
Trent Dyrsmid Aug 10, 2022 ▶ 4:11
Prediction Not checkable as stated
Latka: First $100M solopreneur will scale via contractor systems
“The first one person team to reach, you know, like a hundred million bucks in revenue. And it's going to be someone that can really build systems and rely on contractors at scale.”
Nathan Latka Aug 10, 2022 ▶ 6:57
Disclosure
Nathan Latka tests Upwork contractors by paying 10 simultaneously
“What I do is I put filtering in place and I click on the most expensive hourly rate. And I pay 10 people to do the same task. And then I look at the work quality and then I use the one ongoing, which would, who gave me the Best hourly rate for the best value o…”
Nathan Latka Aug 10, 2022 ▶ 10:48
Insight
Dyrsmid: Overstate task times to test remote contractor billing honesty
“If it's a 15 minute task, if we know it should take 15 minutes, we'll tell them that it takes an hour Because that way the person who comes back and says, yep, took the whole hour. I know that that person's going to milk me for extra labor dollars. Whereas if …”
Trent Dyrsmid Aug 10, 2022 ▶ 11:14
Assertion Not checkable as stated
Dyrsmid: Flowster now has more than 500 customers
“It's more.”
Trent Dyrsmid Aug 10, 2022 ▶ 11:54
Disclosure
Trent Dyrsmid plans to stop founding startups to exclusively acquire businesses
“Like, I've told my wife, this is the last startup I ever want to do. I just want to buy businesses going forward.”
Trent Dyrsmid Aug 10, 2022 ▶ 12:37
Assertion Not checkable as stated
Latka: Bootstrapped SaaS generates about $180k revenue per employee
“Most people at your stage are making about a bootstrapped or doing about 180,000 bucks in revenue per employee.”
Nathan Latka Aug 10, 2022 ▶ 14:11
Disclosure
Flowster plans to launch an enterprise tier charging $20,000 annually
“We are. Yes.”
Trent Dyrsmid Aug 10, 2022 ▶ 15:47
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